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Andrew Gazdecki is the founder and CEO of MicroAcquire, the world's most founder-friendly startup acquisition marketplace. MicroAcquire helps entrepreneurs buy and sell startups.After founding and later selling two successful startups, Andrew decided there needed to be a better way to connect buyers and sellers in the startup marketplace. He founded MicroAcquire to fill this void in the startup acquisition arena.In this episode, Andrew shares how he grew his Twitter audience from 30,000 to 70,000 followers in a few short months. He uses his connections with others, his partnerships, his brand, and savvy marketing techniques to boost engagement and attract followers. It's a fun and entertaining episode, and I think you're going to enjoy it.In this episode, you'll learn: The one thing you should spend at least half of your startup's budget on Proven strategies and tactics to grow your Twitter account How to bootstrap your business and retain your autonomy Links & Resources TechCrunch Cameo Effie Empire Flippers Flippa Bizness Apps Sam Parr Stripe Baremetrics ChartMogul Bumble Brandarrow Bootstrappers.com Y Combinator Salesforce Nick Huber David Cancel Josh Pigford Clearco AngelList Avaloq Naval Ravikant Dharmesh Shah The Ladders of Wealth Creation blog post Andrew Gazdecki's Links Follow Andrew on Twitter Follow MicroAcquire on Twitter Episode Transcript00:00:00 Andrew:I'm a big fan of stair-stepping and entrepreneurship. One of my favorite tweets that I've ever written is, “Start with an agency, get to cashflow positive, and then bootstrap an asset—whether that's a SaaS company or your e-commerce business—sell that asset, become financially secure, and then do whatever you want.”Along the way, you prepare yourself for the next stage of business. 00:00:35 Nathan:In this episode, I talked to Andrew Gazdecki, from MicroAcquire. Andrew started a couple other businesses and sold two of them. In that process, he decided there needed to be a better way to buy and sell businesses. So, that's where MicroAcquire came from. Their marketplace originally focused specifically on SaaS businesses, but they broadened to all of software.The reason I want to talk to him—he doesn't write a traditional newsletter or something like that—but he uses audience really well to grow MicroAcquire. He uses his personal brand connections with others, partnerships, a bunch of fun things.We get into how he grew his Twitter audience from 30,000 followers just a couple months ago, to over 70,000. His approach to Twitter, some of the arguments or beefs that he started with TechCrunch and others, and where he thinks those lines are.We also get into how he uses Cameo; he has these great ads announcing partnerships and others from Russ Hanneman on Silicon valley talking about this, and they're really entertaining.So, there's a lot of fun things in this episode, and I think you're going to like it.I'll get out of the way, and we'll dive in.Andrew, welcome to the show.00:01:41 Andrew:Thanks for having me, Nathan. Always a pleasure to be chatting with you. 00:01:44 Nathan:There are a lot of companies in the brokerage/help-me-sell-my-business space. I think of Effie International, Empire Flippers, Flippa, all of these. So, one, you're going into a really crowded market with MicroAcquire, and then, two, you're coming at it like you're a force of nature.Sam Parr and I we're actually talking about this, of how some people start a project and it's like, “Oh, I'm going to do this thing.” And then other people do effectively the same thing. I mean, it's different in a lot of ways, right? But the same category, and come in and just completely dominate, and grow so fast, and it feels like a fundamentally different thing.What's your take on that, of coming into a crowded space, and then the amount of momentum that you've come in with?00:02:34 Andrew:Yeah. I have a lot of respect for all those companies that you mentioned, and appreciate the compliment.The market that is specifically acquisitions hasn't seen a lot of innovation in a decade. Two of the businesses you mentioned are service businesses, Flippa being a marketplace. I looked at that, and I just thought, there's an angle here where sellers could benefit more than the buyers, and I felt buyers were benefiting. So, I took a left while everyone was going right.Then coming in from an entrepreneur's view instead of a buyer's view, or an investment bankers view, or an MNA advisor view, this was me saying, okay, I'm gone through two acquisitions, I think I have a few unique insights into what it would take to make me comfortable putting my business, generating millions of dollars, on a new marketplace. Then, what information and educational pieces would I need to feel comfortable to facilitate an acquisition.So, I just built what I felt acquisition should be. We still have a long way to go. We've done a really good job of connecting buyers and sellers, and all the acquisitions are facilitated off platform. We've been working on a lot of tooling to really add value to the acquisition, if that makes sense.So we're looking to innovate on things like due diligence or even simple items like writing a letter of intent or streamlining escrow, because everyone complains about escrow.com. so yeah, I mean, sometimes it just happens in markets. Like a new entrant comes in with a different angle towards the problem And different viewpoint. and I think my unique, insight there was just, I had been on. The side of the table that maybe the other, companies had not. but it's also, a giant market. So I, think, arising boat lifts all tides. So, you know, we're here to my require. I just made my group or to help entrepreneurs get acquired and, and, succeed.And so, I think also as, you know, Mike require pick steam and helps everyone else in the market as well. So, but, yeah, I don't have a good answer to that. I don't know. I think if I, if I, this, this will sound cheesy, but you know, I, I I'd like to say I built my group hire would love, like I launched it in the middle of the pandemic. I didn't have a business model. I had no idea how I was going to make money. I just knew I wanted to work with entrepreneurs and startups. And the rest is kind of history, you know, along the way, talking to customers, getting feedback from them, pretty much everything we do is basically feedback from customers.I'm not Steve jobs or anything like that. So I can't read people's minds. So I ask what, what ideas do you have? but yeah, it's been, it's been a fun journey so far. my group is about to turn two, which is pretty wild. 00:05:56 Nathan:That first version, that you launched, what did that look like? What, what was the very early stages of it? 00:06:02 Andrew:The first version was, it was just a simple marketplace with a couple of. Changes that I haven't seen in the market. One was privacy and anonymousy and then no fees or commissions for founders. So it was the first marketplace where you could meet buyers and sell your business without paying a 15% commission like you typically would with a broker or something like that.So I think that was kind of a change. And our business model today is we charge buyers for access to the platform to connect with sellers and, you know, having negotiations that lead towards negotiations. But yeah, the first version, required a lot of vetting of the buyers. Every buyer needed like a LinkedIn profile.Some people have complained about that, but I personally would never sell my business as someone, without a LinkedIn profile. I need to know where you worked, like you know, do you have anyone that's bad for you? not just like John 9, 9, 2, 4 5. You know, I need to know, who you are. and we're going to add other ways of verification, but I think that was a big one. and then also real-time metrics integration. So when we launched, you could connect like Stripe and chart, mobile and probable and bare metrics to get like a real, like a nice, pretty graph, like the revenue to help with due diligence. and then also founders and everything was private. So you didn't know what the business was.And as a founder, you had complete control over the process. So when you were with a broker, sometimes it could be kind of showing your business to a lot of peopleAnd you may not know who those people are. they could even be competitive to your business. And so I think what Mike required did that kind of, and I'm just guessing here because I haven't really liked. Taking a step back and then like, what did we do? Right. you know, I'm usually thinking about what can we be doing better? we really put the founder in control. You know, they were the ones able to choose which buyers to speak to. they were the ones able to share which information they wanted to and which information they did not want to share. And again, it was completely free. So it was very low friction to get onto the platform. And then I think just the, the high, the caliber of buyers and the caliber of listing. So we vet every listing. We vet every buyer. Now that registers as a micro require premium buyer, that's where you can contact sellers. so I think it was just kind of like, you know, going from let's just call it like a car dealership to like a Ferrari shop that makes sense where all the cars are, That it, and if you want to know who the owner is, you have to pay for that access, but it was a very specific towards startups, specifically SaaS.So I think that's another thing that I'm thinking of now is we, we went very narrow at the beginning, very narrow. So we were very specific on, specifically, bootstraps, SaaS companies.00:08:59 Nathan:Yeah. I think the approach in different marketplaces is always interesting when, you know, a marketplace is how businesses has like is a generic category, but then the twist on it, of, the seller not paying anything. And it being the buyer who pays, you know, a subscription for access. Why I think that that makes for an interesting twist, because then you're going to have this much higher pipeline of, you know, high quality businesses to look at.And so if a seller is paying for that, that makes sense. It reminds me of like, Bumble as a dating app being like, yep. So within the category of dating apps, but, women have to send the first message, you know, and, and like, that little bit of a twist makes it the marketplace feel, very different and changes the dynamics of. 00:09:40 Andrew:Yeah. I was going to say something, someone called micro fire shark tank, like if shark tank and dinner had a kid, I thought that was kind of an interesting analogy. but yeah, I'd say the, the key. The unique insights I had was again, like, from my perspective, if I'm going to list a business, I need to know who's seeing my information. I want to be in control of, you know, what information is being disclosed or being displayed publicly. and I don't want to commit until I really know, the quality of the buyers. And so that I think was very appealing to just being an entrepreneur. I think I. You know, understood the needs of other entrepreneurs and just kind of got it.Right. But I'm not gonna lie. When I, when I first launched it, I have this, I keep a journal that I update every month. It's not like a weird, you know, Hey dear diary thing. It's I do like, what's going really well. What are some things I'm worried about? and then things I'm grateful for, just to, you know, kind of keep it story log of my life. And before I launched my group wire, I actually, cause this idea had been attempted before, like a real startup acquisition marketplace. I think some of the other market places are more, geared towards, you know, content sites and domains and 00:11:07 Nathan:Yeah, 00:11:08 Andrew:Affiliate websites, but not real. Startups like SaaS companies, e-commerce companies, crypto companies, we've moved into a number of different categories.But, I wrote in my journal, I was like, I don't know if this is going to work, but at least it looks good. cause I, I just thought it needed to exist so bad for entrepreneurs that, we put a lot of thought into user experience and design. So it felt modern. You know, when you're working with startup founders, you kinda, you know, you want to really build trust, like yeah, if you're going to sell your business with us, your startup, you know, we also, we know how to build startups as well, and design them well and make them feel like something like this, this feels legitimate.And I think that's a, what I would call, you know, closing the credibility gap, you know, really, that first impression is so important. So we really kinda overdid the initial MVP. 00:12:06 Nathan:Yeah. I think that design is one of those things where you can go a long ways. And it's probably the first thing that people cut when it comes to the MPP. And that's just, I'm like, Nope, that's not an MVP. You have to cut features. You can't cut like the quality of, of the design. And if I have a limited budget, I'm for sure.Spending half of it, if not more on design. So I think you made the right move there.00:12:29 Andrew:Yeah, I think, I think today, I don't know if we're going to go off topic here, but I think a lot of startups today can legitimately have user experience in design as their competitive advantage. Just saving people, a Couple of clicks, making things easier to use, having a product where you don't have 50 tutorial videos, you've got to watch, or course you have to take. that's a huge advantage. and there's a lot of products that are very clunky and kind of feel like a car with, you know, like a jet ski engine added in. And I just kind of like a Jenga thing, you know, there's just so much technical debt to the product. I think though there's some products out there that I think could be rethought in terms of like the experience and the design they're delivering to the customers.But that's, that's probably a whole nother topic.00:13:22 Nathan:Yeah. Yeah. But we agree. And anyone who's listening to this show knows that I care deeply about design. one thing that I want to ask about and spend a lot of time on is content strategy. if I go to your website and go to the about page, it just lists your title or like your, your job description and your role as marketing. and so I'm imagining that's where you spent the majority of your time in, from the outside. It looks like content marketing is, either a very large or the largest portion of where you spend your time and how you're looking to grow MicroAcquire. Can you talk about how you think about content marketing and the growth of the business? 00:13:59 Andrew:Yeah, I think that was twofold. So number one, the first thing that happened to me when business apps was acquired, I had like five founder friends reach out and they said, how did you sell your business side is, is, were what, you know, so as entrepreneurs, we're not trained to sell businesses, we're not educated on what is due diligence, what are the legal steps of an acquisition?So I felt it was a twofold, the problem with the benefit. And when I say two folded, not right. Prom, but well point number one. Yeah. It's a phenomenal growth channel for us. we think heavily in terms of, you know, what is the content that, entrepreneurs will need when they're going through an acquisition, because the more we can educate them on acquisitions, the more we'll be able to facilitate.And I think that's been crucial, but then two there's just no content in the market that like there's books on fundraising, there's books on marketing there's books, on design there's books on there's a couple of books on, exits, but there just is such a disproportional amount of content available for everything, but a startup being acquired, that we felt, you know, there's an opportunity here to kind of be almost a, I don't want to say thought leader.00:15:20 Nathan:Yeah.00:15:21 Andrew:Kind of write the book, if you will, on, you know, this is, but also important to note is we write content for the seller, not for the buyer. we kinda think, you know, the buyers are set, you know, the buyers that we work with are, you know, private equity firms, corporate dev teams, other startups, people that, generally are sophisticated with, and also a lot of first-time buyers, but so the condoms still applies, but it gets you in the head of the entrepreneur, but we wanted to really empower the founder.So you'll notice every piece of content is angled towards the seller, not the buyer, if that makes sense. And I felt that was critical and just something cool to do for other founders, not like, Hey, this is an article on how to get like the cheapest SaaS acquisition possible. so we read articles on how to maximize your startups exit as.00:16:14 Nathan:Yeah. I mean, that, that perspective is in your, like your founding story for the company, But then it's interesting, like, all right, it makes sense that it carries through all of your content marketing as well, because in the same way that you have know who your customer is, which in the marketplace, you have a lot of different customers or you're, you know, you have both sides of it, but, 00:16:32 Andrew:That's that's something. Yeah, you're onto something. So that's something that, we determined, very, very early. So when we raised our, our seed round, I hired my former VP of product, VP of engineering. My former CFO, and my former head of marketing who's now gone. Cause he went, he was, he was, he was like one foot in he's started this, agency called brand arrow. so if anyone needs help with, Facebook ads or just any sort of SaaS marketing shadow, Tim brown now I told him like, Hey, you got to, I'm a big fan. I need like a micro mafia at one point. So I, I told him to dive in on that, but, we did an offsite and we, defined our culture, you know, our values, but really specifically, like you said, who was our customer?Cause it could be so many people, it could be okay, buyers, but there's so many different types of buyers. You know, which ones are we going to cater towards? And then there's sellers, you know, there's so many different types of sellers. There's people looking to sell comments. Again, domains, Amazon FBA businesses, SaaS founders.And so we really narrowed in, got super specific with our buyer And that really guides a lot of the decisions that we make all the way from the content to the product. I think that's really crucial in the early days, because you can always expand outwards. There's a theory. I don't know if you've heard of this, but the bowling ball theory, you've probably gone through this with your business where, you know, you start with one sorta audience and then I one customer segment, and there's just like these natural sort of like, you know, other segments that target for us, it was like e-commerce.And then we've been seeing a lot of just miscellaneous. You know, profitable software companies. So now we're a little bit more broad. So when I described my required of people, I say, it's a marketplace. So profitable software businesses, not just SaaS anymore, but yeah, we started really specific with SaaS founders being, our initial customer,00:18:37 Nathan:Yeah. Like narrowing it on. That is always a good thing. Okay. So content strategy, I'm seeing you do a lot of different things. one at let's just take Twitter, as a starting point. So I was looking back in August, you had 30,000 followers on Twitter. You have 73,000 followers today. You're tweeting five to 10 times a day.Often. Like you got a lot of, a lot of posts going out. It seems like they're resonating, obviously from the growth and all of that. you have a lot of these single posts are like single sentence. You know, here's an idea latch onto it, like positioning type things. So like one, one example is, instead of thinking of a hundred plus startup ideas, pick a customer you'd love to serve and solve their problems.That gets a thousand likes, 150 retweets or more. I want to know, two things, one, tell me about your Twitter strategy of how it fits into the broader business and what you're trying to do there. And then two, we'll just get into what's working. What's not working. 00:19:33 Andrew:Yeah, definitely. So Twitter strategy, there is absolutely none, aside from having fun. And I'm a firm believer of this, I think when people try to have a social media strategy where their goal is to grow followers. And so you start doing stuff like looking at other people's tweets, and then you take a tweet and this how I see this all the time with some content I put out like, oh, that looks very familiar, but I don't, I don't, you know, I don't care. but they're trying to grow their audience and they're not being authentic to who they are. And they're trying to be, you know, they're trying to, I guess what I'm trying to say is, Find a way to utilize, you know, social platforms in a way that you enjoy. So, one thing notice if you look at all my tweets, they're all from my iPhone.Like they're not from my web app. They're not from a scheduled Twitter thing. I just like that tweet. I remember writing that tweet. I was like, in my kitchen, I was just like, did it, you'll also see a tweet right before this podcast. That's just me. I was waiting for you to come on this podcast. I was like, so I think my point being, and I think this goes even broader is just, you know, if you want to be great at anything, and I'm not saying in any way, shape or form, I've created Twitter, but you just have to enjoy it.And then if you enjoy it, you're consistent at it. And then, I do have a few rules though. I don't usually comment on people's cause like you know, once you start getting to a certain point on Twitter, people, you can just post like Entrepreneurship is awesome. And then people have like a hundred questions and I just don't have the bandwidth to answer all those questions.So I usually will, I'm watching those questions and I'll usually, if some, if something's interesting, I'll, use that as a new tweet. and then you get tweeted out a lot, like, Hey, follow me. Like, Hey, we'd be on my podcast. So I kind of have a rule of like stay in my lane, if that makes sense. I've done a little bit of like beef marketing and stuff like that, you know, I'm sure you saw me like call out like tech, Raj, or maybe like throw a couple of shots at like, just joking, like VC sort of like, you know, shit posting type stuff. And that works. It definitely works. And there's some strategy behind that. That's probably one part of my social media strategy that was, strategic, it's effective, but it's not for the faint of heart. cause you do you make people pick sides, so you're going to upset some people and you're going to make some people really cheer you on.And so, I'm kind of done with that phase. that was fun. 00:22:20 Nathan:So if someone is in that phase or they're thinking about it, right. They, have a specific audience for their business or like a specific focus. They've chosen a niche and they have some strong opinions and they're not that kind of person who's like, you know, like let's not cause any conflict.They're like, no, I'm actually, I'd be, I'd be willing to get into a little bit of conflict. what would you say what's, what's your advice on going down that path of like, if you're thinking of oh, there's a TechCrunch in your space or someone else that you might want to pick a fight with? 00:22:49 Andrew:Did you just gotta really believe it? like, and I think it has to be factual, like what I said about, TechCrunch, as an example, just go on their website right now and see it. And tell me if you can find an article about a bootstrap startup. like, that's all I said is like, you guys are a publication that writes about just venture backed businesses. and you know, what kind of really struck a chord with me with that was my prior company business apps. You know, we were in TechCrunch, all the time. Like they loved writing about, you know, real business building storage partnerships, you know, version 2.0 launches, you know, international exp like, you know, stories that inspire entrepreneurs.And they moved towards, you know, this really venture backed sorta, you know, you're, you're either in it, or you're not in it. And I just blindly called them out on time and then some people. were like, yeah. And then I was like, huh, maybe there's something here. And then I just, and this is how I always think of or how I validate ideas as well as, so I have a publication now called, bootstrappers.com, which is just kind of like my.Like what I wanted, like just, you know, I want inspiring stories, like back in like 2010, you would read articles on TechCrunch about like, two people. They just launched a product, no funding. I remember some of the writers I used to work with, are they all left? They're all gone. It's like a new, it's a new company.It's, it's been acquired by four different companies. And you know, some of the older writers you're out, but, the older crew, would kind of joke and say, Hey, BC's like, I hope you banked me one day for writing about all the companies that I discovered. and then you find it later. now the opposite is entirely true. And so I, I wanted to bring that style. You know, journalism back where it's stories about companies making like 200,000 a year or 500,000 or 2 million. because you know what, I read an article about a company raising 200 million and then 500 million, like the next week. it doesn't really inspire me too much.And I think that celebrated so much today and, you know, the startup community that I think it's a little dangerous, I think, as a young entrepreneur, like if you think the path to being a successful founder is. Get into Y Combinator, raise a bunch of funding, get featured in, you know, these magazines, because that's what happens when you get fun.That's like the only way to get covered sometimes, is funding announcements. and even then it's hard cause there's so many. so I think that creates an environment where a lot of entrepreneurs are focused on raising capital rather than raising or generating revenue from customers.And that was just something that I lived through.I had a really good mentor. We're told, are we going off topic too far?00:26:04 Nathan:Well, I do want to take you back to, like the idea of like picking a fight. But finish the thought with a mentor. Who's everyone, everyone listening knows that ConvertKit is bootstrapped. I'm a huge fan of that and the same things, the same reason that you're picking a fight with TechCrunch or that you did, I would do the same because we experienced that, you know, we could have more revenue, more customers, all of that than, anyone else, but they're only going to write about the VC funded version.So, 00:26:28 Andrew:Yeah. So so long story, short business apps, my company prior, boot shove that business, and I just had a really good mentor Christian free Freeland. And he was always challenging me to think against the difficult soak on early pap. And we were based in San Francisco for five years, eventually moved to San Diego and that's where we exited the business. but, yeah, now that like I'm on my third, I took a little hiatus and went into crypto land for a little bit. So it got away from like SaaS and stuff like that, but now I'm back home. and yeah, just saw that and said, okay, and then actually TechCrunch did write a little bit about bootstrapping and then I've also seen a lot of other people start saying the same thing, like agreeing, which I think has been cool.It, which isn't like it's not a bad thing that TechCrunch or any publication, I don't want to just hone in on, on TechCrunch. because th they're, they've done so much for so many founders. but yeah, other people, I feel like the first shot was fired. Like, Hey, You know, we miss the old version of, you know, maybe mix it up a little bit.And they've taken some of that feedback and I've actually written about some bootstrap companies and then other people have kind of said the same thing. Like, you know, the startup ecosystem is really turning into this, you know, fundraise craze news cycle. And, you know, there's 99% of other startups that aren't going down that path.So that creates kind of like a movement. So that was like the benefit of, of beef marketing sometimes is you, again, make people pick sides. Some people agree with it, some people don't. yeah. So advice for anyone in terms of beef marketing, I, I, again, I, going back to my original point, it how you have to believe it, you have to believe what you're saying.It can't just be like, you know, one foot in, from my perspective, Most of the major tech publication should write about, you know, businesses that are profitable and sustainable and ones that are raising a bunch of capital and going public like a good mix would be amazing because then that gives you a true picture of, you know, all the different styles of entrepreneurship, you know, the ones that are at the top of the top and the ones that are taking a more sustainable practical approach, just giving a more realistic view into the world of entrepreneurship instead of just kind of, you know, putting this one style on a pedestal.Yeah, I mean, just get ready for, I mean, nothing bad happened. so I would just say also with beef marketing, it doesn't have to be just, an individual Oregon or, or an organization. Like good examples. So I've always had a, like, kind of an, a branding, an enemy, and all my businesses for business apps.It was a large businesses. Like our main sales pitch was, you know, Starbucks down the street, paid 2 million for their, mobile app, blah, blah, blah. You know, would you like to create that same customer experience for your customers and, you know, like David versus Goliath type story, you know, Mike group, we're kind of fighting for the founders.Then all the other stuff that I just talked about, but Salesforce had, their, their enemy was on-premise software. They essentially invented SaaS, you know, the company. Say a little chat thing. Yeah. They had a big campaign of just no forums. Like no one wants to download an ebook anymore, like forms go away, please. and I thought that was very clever, box.com had some beef with Microsoft, which was definitely fun to watch. I've I've been around long enough where I remember seeing in San Francisco, like, the billboard of like box, just basically saying Microsoft sucks. you know, Uber and Lyft were throne, had a food fight for awhile.That one probably went over over the line maybe. but yeah, my point is, is there's other examples it could be, for your business, it could be expensive. To like, I don't know, like it could be, it doesn't have to necessarily be like a organization or it definitely shouldn't be a person either.Like don't ever like just straight up call. That's just, that's not cool. Like if you have a problem with a person, call them and tell them your problems, like, that's it now. Like that's not, I don't, I don't support that at all. I think that's ticky-tacky and just a sign of just weak character, if you're just literally, you know, trying to tear someone down for your business's benefit,00:31:28 Nathan:One thing that's interesting, I think is you probably watch some, maybe beefs between individuals is just how many of them, maybe are planned or facilitated in some way. that is interesting. Like someone, messaged me today because, sort of like Nick Huber who's, has a popular Twitter profile under sway startup.Hopefully we'll have him on the show soon. He was, he posted something like controversial, which I know is one of his top of funnel tweets, right. To try to get as much attention. And so I purposely like aggressively disagreed with it, you know And then we're just separately texting, like, Oh, thanks for the engagement, you know Right. Because we know that by deceit, like if he strongly takes one stance and I strongly take the other stance, then like one, no one will think we're actually mad at each other, but then too, like, it'll get a lot more attention engagement. So a lot of people are doing. Some version of that. or if you see a happening usually between two individuals often, they're probably on really good terms behind the scenes. 00:32:26 Andrew:Yeah, I did not know that that's, that's me staying in my lane. I, I, I missed it. but yeah. I, mean that's business entertainment, you know, there's, there's nothing wrong with that, but I, think there's a line to be drawn, you know, like, If you do engage and stuff like that. number one, I think it's always great when, like, if it's real and then they like, like, Hey, we're cool now.Like, you know, we did this in pub and now like, okay, we're on 00:32:59 Nathan:Close that loop. 00:33:00 Andrew:Yeah. I think, I think that's really cool to see. but yeah, public food fights, not my thing. don't have appetite for that or any advice, but I will say, I will say Nick is coming hard on some, some of the stuff I've said, like, 00:33:16 Nathan:Whole angle. 00:33:17 Andrew:Yeah.The, the one thing I'll say about that though, that style like shit posting, you know, I was like some view of like VC funds just based on like shit posting and stuff like that. what I've noticed, ‘cause this, this actually, this is probably a good tidbit for, you know, if you're considering, beef marketing and what happens is you draw in a type of crowd that likes that negativity and it, and that can drain on you.And so if you should ship posts all the time, like a large amount of your followers are just going to be shipped posters, and they're going to be, then all your comments are like, use a blah, blah, blah. I mean, if you go on Nick's feed, you can just kind of look, just look at his comments. He has like a million people.Unfortunately insult, I kind of feel bad for him sometimes because I've also seen him comment how it affects him personally. I, I don't know him, so maybe it doesn't give a shit, but, that's why, again, I say, stay in my lane. Just keep it positive. Aye. Aye. Microfibers entire marketing strategy is literally just inspire or support encourage entrepreneurs.It did. not, I mean, not getting beefs with people and stuff like that.00:34:33 Nathan:Have you. like, there's the side that you're, you're taking of, using your personal brand for marketing, you know, growing a Twitter audience, all of that. You're very off the cuff of like, you know, just firing off, tweets or things that you, you think about. But at the same time, like you're a professional marketer and you tend to, from my new at you and other places, like you're very methodical, you tend to attract things really well.Do you track efforts that go into Twitter and Like how that translates into, you know, deals on MicroAcquire or new buyers or sellers, you know, like listing listing companies or any of that. 00:35:10 Andrew:So I'm a big believer in, so David can sell from drift said this really well where, I think I might've mentioned this to you the last time we talked, but, he, he broke it down into like three phases where, we've gone through three phases of SaaS. Like the first phase was invention murder. The first person to kind of build a tool one, the market.And then the second phase was the first company to really figure out the best, go to market strategy, like LTV to CAC, you know, AEs STR ratio who could, who could land grab the market fast enough. And then right now he says, he calls what we're in today, the Procter and gamble phase, which is your brand. So it's most defensible part about, your business is your brand. Your technology can be copied. it's easier than ever to raise capital to build a team to do that. There's also other things like your culture and your team's talent and just, you know, again, your unique insights into the market. People can copy chapter one, but not chapters two and three and four that you have planned. so I think a lot about that, a lot in terms of just brand and market reputation. But So, no, we don't, I don't measure it. when a tweet goes viral, like the one you just mentioned, I don't look at the comments because when a tweak gets like a thousand likes00:36:33 Nathan:Yeah,00:36:34 Andrew:Is gosh, like the questions and the people like disagree with you and just, you know, you start to enter, it's like, you're in a stadium of, you know, 200,000 people are reading this and then like 200 people have comments, not everyone's going to be like, yeah.Like half of them are going to be like negative stuff. So, yeah. So I, I push, I push away all negative energy. So if, if it's not positive, I'm over it. 00:37:05 Nathan:W what you're describing is interesting of the city of idea of, if you think about it, like maybe your immediate group of friends, you post something, the people who reply right away, you interacted with them a bunch, like that's who's on the field or whatever. And then the next group is like the coaches, the diehard fans, like the re the support staff, everyone else, like those are your Followers. And then you can tell every time that this tweet goes beyond that, because you start to get, like, I had one on company culture that, was like a thousand retweets and went really far. and you could just immediately tell when it had gone to like two levels beyond the people who follow me, cause it just, it went totally off the rails. And you're right. That the only thing you can do is like mute your own thread and move on. 00:37:50 Andrew:Yeah, I just, and you could tell, cause I usually will like everyone's tweets just cause I respect everyone's opinions, like bringing, Nick back up. He, I remember I had a tweet, just something about how entrepreneurs that have maybe struggled in their childhood, have an advantage. He came in with like a strong disagreement and kinda, but I respected it.But then I, we, we kind of close the loop with like, Hey Mike, I think you're taking this out of context. so I'll respect everyone's opinion, but once it goes, you know, I'll like all of, them. And then once it goes viral, that's when it's like all, everything is just nuts. Like, you know, I can't, I would never want, I can't keep up with it.And then too, I've probably already moved on to like three or four other tweets that, you know, I'm thinking of or something like that, but I think, I think that's another important side of, just social media in general is just understanding like everyone has a right to their opinions. So even if people do strongly like disagree, that's awesome.You know, everyone is entitled to their opinion. Everyone has, You know, unique view of life And how things work. and I respect all those opinions, but I think one. thing about social media that can get kind of crazy is when you're taken out of context, I've had that happen a couple of times. Like the one time with Nick, maybe, he took it as I think like, people with really great families, you know, like divorced dads make less than married men. and I, was like Nick, no, this isn't about diverse families. It's just about like entrepreneurs struggling with when they grew up. Like I were Joe, and then I had another one. This one was, this is a crazy one. I had one, I tweeted out. Hire people you'd be friends with. And that was, literally someone literally took that as far as saying, nice job describing why tech is sexist and racist in five words.And I, and I was like, what? And I was hanging out with my sons. I didn't have like enough, I didn't catch it in time. And so I come back, to my phone and I had to delete the tweet. And then I actually, you know, put more con like, Hey, I meant that as like, you know, hire people, you'd be friends with and you'd care for them personally and professionally, not just hire a bunch of white people or something like that.Like what? So sometimes you gotta be careful, when that kind of stuff goes down. And it's also just fascinating how people can, again, their, their perspectives, like their perspectives and their viewpoints. you know, you can say one thing and it means one thing to you and something completely different to someone 00:40:47 Nathan:Right.Yeah. I remember a time that Josh Pigford, for bare metrics, had a tweet about concerns in your, in a resume when someone, you know, has had 10 roles in 10 years or kind of thing, or like jumped between roles every 12 months. And that, I I'm not even fully sure why, but, but that one, like he got jumped on in a very similar way of people taking out of context and saying like, this is what's wrong with technology and 00:41:14 Andrew:Let's talk about that for a second. So when you're, when you're taken out of context, Just admit it, just say, Hey, that, that this is not what I meant. And then I recommend is deleted tweet, and just clarifying, just like, Hey, I wrote a tweet, this, this is what I actually did. I deleted the tweet. And then I said, Hey, I had a tweet taken out of context and it's obviously a little embarrassing, you know, but it's the right thing to do is like, Hey, like that's not what I meant.So also admitting, you know, that's not what you meant, but clarifying when people like, that's not that that was not my intention of those five words in any way, shape or form, even like, that, that, that experience was so far off. I still kind of scratch my head on it. But my point being is, you know, it, you know, take one back, like, Hey, listen, I, I said something, it was taken out of context.I apologize. this is what I really meant for further clarification. And it'll just make your life a lot easier instead of trying, to defend, because I know the thing is if Mrs. Also I don't really comment too much on social media. Number one, it's just exhausting because you can have so many, then you're like a, full-time like customers support person on Twitter. again, you know, once You kind of engage with someone who vehemently disagrees with what you're saying, or has taken you out of context, it's really hard to change their opinion, if not impossible. So even trying, once you, if you just try you lose. You just start throwing food and stuff like that.So that's just kinda some of the crazy stuff I've seen happen on, on Twitter as, you know, gone a little bit more active. cause I, I wasn't active on Twitter, so all this is like new to me too. I'm still learning like, oh shit posers. I didn't, I didn't know those existed or like, oh wow. You can get really taken out of context and it can go viral and people can say some mean things.So yeah, my, again, going back to just saying I stay in my lane and just talk about stuff that I liked it. Talk about.00:43:35 Nathan:I like it. something else that you've done that I hadn't seen other people to do before, but I get it as a strategy. so separate from like just sort of specific, but it's using cameo and using spokespeople on cameo. for your business specifically, you got Chris, demon topless from Silicon valley and all of that to do announcement videos for partnerships and one they're amazing. but like w where did that come from? And, how'd that turn into something that like, And, now if someone says like tres commas, like in relation to micro choir, everyone's like, oh yeah, that makes sense. 00:44:15 Andrew:So for the longest time, it was just me running Mike requir. I was a solo founder. and on the team page, we just like, as I was working on the design with, I initially use an agency to help with, the development. And, there was a team page and I was like, ah, just put Richard Hendrix, Gavin Belson, and Jen yang from Silicon valley.And it just kinda was, I just thought it was cool. And some people like, you know, called it out and was like, are these really your team members? And I'm like, yeah, they were super harder recruit. So I'm, I'm a huge fan of the show because it is shockingly accurate and just hilarious. and then, yeah, so I actually, you know, before, like right when I launched my crew choir, I.When on cameo saw Russ Hanneman Chris. I can't pronounce his last name off the top of my head, but, you know, he was available and he was like my favorite character. And I was like, yeah. W do you want to talk about my group choir? And since then we built, you know, a pretty good relationship in terms of, you know, just working with them.And he's a really great guy. Like he's a really, really, really nice person. but my point here is I'm always thinking about what's, I'm always learning and I'm always trying to think of what is changing in marketing today? For example, the marketing playbooks that worked five years ago don't work as effectively today because everyone adopts them and starts using them.And then it starts to, feel like marketing and the best marketing doesn't feel like marketing it's entertaining, or it, captures your attention in a way where you go, whoa, I haven't seen that before. So I'm always trying to think of unique ways to, capture or actually I should say, earn audience attention rather than buy it, or, you know, writes an ebook and engaged it and get your email and then send you 30 trip emails, which worked fantastically a decade ago, which killed a decade ago.But So that's kind of where the thought process and then candidly. I would say, I might laugh the hardest out of those videos. So it's like my like guilty, like pleasure. cause you know, they're not free. So like, you know, I, I probably am lapping the hardest, like when those go out.00:46:46 Nathan:I've I've laughed pretty hard at a lot of them, especially as like, they end up in a series where they like build on each other. The, he uses jokes that he first coined and, you know, first video. And,00:46:58 Andrew:Yeah. a little background on that too is, I didn't tell him to make up anything like he's made of like gas Decky style, micro Gaz, micro, and like, I don't tell, I just basically, cause you're only able to write in like two sentences and he he's just a hilarious person. So any startup looking to, you know, announce something, I highly recommend checking it. 00:47:21 Nathan:I guess how has the business side of it work? Right? Cause if you go on, on his page in particular, it says $349 for personal use or 909 plus for business use, which makes sense that there would be a split there because you've obviously gotten a lot of earned, earned, attention from those. how does it work actually on the payment side? 00:47:41 Andrew:In terms of like using Kamya.00:47:44 Nathan:Yeah. Using cameo, maybe using Russ specifically. Well, Chris, not Russ. But using him specifically or, you know what you've done, you've done with, other people on cameo. 00:47:56 Andrew:Yeah. So he's kind of the only we did a partnership with Clearco and I had like the game, the rapper, duke came here just because I kind of went on like a cameo binge, like I've been a fan of you forever.00:48:12 Nathan:Cards on file. You know, you're just like00:48:15 Andrew:Yeah. I was like, I'd love for you to just say micro choir. Like this is awesome. who else did we get?I can't remember off the top of my head, but, what's been interesting to see what Chris is. when I first booked him, he was $200. Now he's 5,000. So he, has definitely, you know, made some waves in the startup community. And So it's, it's cool to see him like, you know, making people laugh and helping startups get exposure and then raising his prices too, which is, I think something that, you know, most startups should do.So he's done a very good job of that. It, it went from like one K to two K to three K. Now it's at like, 5k, so he's expensive. 00:49:00 Nathan:So that's like when we see something like that, right. If the nine and nine plus, in the buying process, then later, does it tell you like, oh, here's like once you fill out, the initial form, it'll tell you what, what the price is or how's that work?00:49:13 Andrew:So there's, there's a personal use. So you can use his personal, I don't know his like personal cost, but let's say it's like 500 bucks and that would be for like a birthday wish or something like that, which can be a great way to motivate like your team, like, Hey team, great. You know, Q1 or Q4 that's ending, here's our goals for next year, you know, made, they want to me to give you all shout out, that'd be 500 bucks, but then a business use where you posted, externally, so on Twitter or social media, or, within some sort of piece of marketing content.The price for that is usually 10 X, you know, internal use. 00:49:55 Nathan:Did any of the other ones that you tried? Did you feel like they got attention or that kind of thing make you want to do it again? Or was it more just the ones with Chris that really resonated. 00:50:04 Andrew:I think probably you'll see less cameos, out of me, I think, you know? there, there, there gets to a point and we could, we could probably have another podcast about this, about like things with diminishing returns. And I think I've kind of, you know, used them so many times that, I mean, for the really big like, announcements that we have coming up, like maybe twice next year or something like, that but I think there's sort of a diminishing return, especially with the cost, you know? I think building in public kind of falls into that category a little bit. audience exhaustion in terms of like paid ad campaigns. you know, so I'm always thinking of that stuff too.I like, are we overdoing it? cause then it just kinda starts to get corny is when you're doing it over and over and over and over. and it's not really like, whoa, he's here. Like I didn't expect this. And when it starts to become expected, I think if there was just kind of a little bit of luster. 00:51:05 Nathan:Yeah. That makes a lot of sense. something else that you do a ton of is partnerships, whether it's with PYP or angel list or whoever, it feels like micro choirs coming out with a partnership. Every, I don't know what the actual cadences, I feel like it's every two weeks to a month. what's the, what's the strategy there. And is that like a very deliberate, marketing strategy or is it just like, look, this is a natural fit. And so we're just going to do a better job. It made sense to do the partnership and we're just going to do a better job promoting it than most people do. And when they come out with a partnership, 00:51:35 Andrew:Yeah. I mean, so the pipe Clearco Angeles partnerships all made total sense. They help startups get acquired, which is, you know, the purpose of our business. And, you know, our, our main metric of success is helping startups get acquired. So helping them get financed, increases the buyer pool, which then can lead to more acquisitions.So there's, those made a ton of sense. and then we also want to expand internationally. So we partnered with, essentially like the angel list of, Africa that serves 40 countries in Africa. And so I thought that was a really fun partnership in terms of, you know, helping, really underserved. areas of the world, or support underserved areas of the world with my group who are in terms of, you know, just our message and just our encouragement and we're going to continue those.So we're looking, actively speaking with, individuals that are, you know, accelerators or like, start a boot camps and like Turkey or Europe or the UK or Australia. I have a number of conversations, but we'll probably go a little lighter on those because I also feel like the partnership thing is it's like, okay, another part is another partnership might require really. but that's, I think partnerships are, what I would call a non-linear growth strategy. So it's basically, you know, what you're doing is you're leveraging, you know, number one, Another company's brand So you're, you're borrowing some of their brand equity saying like, Hey, we're partnering. So their capabilities are now part of our capabilities and vice versa. so there's benefits on both sides. And then you know, with products that, you know, pipe clear co and Angeles offers specifically, it adds value to our product. So it's like a win, win, win. It's a, it's a good marketing play, good brand play. And then it's good. Just, you know, product play without, a lot of, you know, engineering needed. 00:53:41 Nathan:Is there, like, do you have engineers internally just devoted to, you know, these integrations or, or did they tend to be more on the marketing? you know, our business ops side rather than on the product side, because then they can be expensive on the product side.00:53:55 Andrew:Yeah, they definitely can. I would say they're more. On the marketing side then on, like for example, the angel is partnership is just a landing page that so Avaloq, the CEO of Angeles is an investor in might require and then evolve in an investor in my rewire. And so I just asked, I pointed out this other company that was making an SPV product for private equity firms.And I just said, can you make me a landing page? I'll promote it. And so inside my group where there's like a drop down that says raise bonds, and then it takes you to a landing page. So minimal product integration there, but it's just kind of like us saying, Hey, if you, if you're looking to raise funds, this is where we recommend you doing it.We've done that with mercury bank as well, which is just, again, you know, you acquire a company, you probably want to transfer those assets and do a new entity. That new entity is going to need a bank account. So we're just kind of getting all the re they're almost like perks. If you will.00:54:54 Nathan:Yeah. That makes sense. And then it's not this big integration that you're having to maintain for years to come or.00:55:01 Andrew:Yeah, no, it's not like a, like a Facebook, like a, you know, SSO log-in or something like that. you know, it's a, it's a lot simpler. It's usually just like a lane kicking over to a landing page, you know, driving traffic to them and then we get some sort of kickback for whatever business we drive to them.00:55:20 Nathan:Is there anything in particular that's worked well on, like the partnerships that have been a, a, huge boost, right? Where either you've gotten a bunch more attention for Mike require built the brand. Like, are there things that you see in common on those ones where you're like, yes, that was a home run versus the ones where you're like, I think that was worth the time to put together.Maybe 00:55:40 Andrew:Yeah. I mean, I'd say, I'd say all of them, I'd say my favorite are definitely the Clearco and pipe partnerships. like. Hers is he, oh, he bought me this to kick off our partnership. It's assigned Mike Tyson glove and we've done a number of acquisitions together. I think their company's fantastic. I love working with our team.Clearco same thing. So pipe, I was finance all of our SaaS deals exclusively, and then Clearco all of our e-commerce deals exclusively and they're just great teams and it's a clear need. You know, some people want to finance these with, these companies and we make it extremely seamless to connect to those companies.And we even do like pre-financing. So if you're a founder looking to sell on Mike required and you want to give a line of, you know, potential financing in advance to a buyer, we can, pre-approve a seller. So it just makes kind of the, you know, when you're going to buy a home, it's like it's pre finance or something.I don't know if that's a good analogy, but, those are, those are partnerships that really add, like they were on the product roadmap and they just, you know, we just went to the best ones in the market with the most credibility, with the largest capital pools. but also with the engineering resources.So, you know, anytime a company is, you know, financed through pipe, we get a notification within slack. It says like, Hey, add preapproval number to this company. So we just, we, instead of working with like a ton of different financing partners, we just pick the best ones and then then integrated deeply with them.00:57:23 Nathan:That makes sense. One of the things that I wanted to ask about before we wrap up is, on the sort of the investor influencer side, you have a lot of people, like know, you mentioned Deval and, and others who, have invested in MicroAcquire. And is that, helping of like helping you you know, amplify some of these things on Twitter amplify, these partnerships, open doors in some way.Do you think you get something similar with like a influencer program or has the investor side really been a good, good angle for that? 00:57:54 Andrew:Yeah, that's a good question. So yes, there's definitely the group of investors that my career has is like all my, like idols, like, you know, founders of companies that, you know, I like, you know, Dharmesh from HubSpot, Neval like, From Angeles, like those are some of my favorite companies and I get to, interact with them on a, on a very limited basis. I don't reach out to them for advice, very often. So I think that also adds to just, you know, brand equity of just, being a marketplace, you know, and us wanting to build this with the startup community. That was kind of more of the thought process behind it. But now, I mean, you could even look at my likes.I, I ha I, was, has evolved over, liked something of, mine now has Dharmesh maybe once, like, so now I don't rely on them for like social media support or anything like that. but it, it is, a good way in terms of, you know, when you raise your entreprenuers, you get kind of, again, unique insights because most of them have been through MNA. so, so typical VCs, but, I, I really liked that, style of, of fundraising is when, obviously I'm a bigger advocate of bootstrapping because that's kind of, you know, where I've spent, or had the most success. But if you're gonna raise capital, I, I recommend entrepreneurs for us because they have experienced building a business.And then typically with, you know, acquisitions specifically in my case, which is you know, extremely helpful. 00:59:33 Nathan:Yeah, you and I are both known for bootstrapping. And we're also, I think, pretty well known for not being that dogmatic about it, of being like, here's what we did. Here's why it works well. Here's why the other path can be fine too. you know, rather than being super dogmatic in one camp or the00:59:49 Andrew:Yeah. That's one thing I've noticed since being vocal about bootstrapping that I think is a little toxic; if you're funded, it's like, I hate you. Then, if your bootstrapped, venture capital's just a tool. If you know how to use the tool correctly, it can be a great accelerant to your business. Everything comes with a cost. So, when you bootstrap, you have to kind of eat glass for much longer. I've lived that life, but at the end, the rewards can be epic.So, if your goal is to make money, you should probably bootstrap, because you can sell the business whenever You want. You have no approvals. You own the whole thing. Nathan, if you wanted to sell your business, you don't have any investment or approvals, or anyone saying, “No, you need to hit that billion dollar mark.” If you want to really disrupt the market, or change a market or, go a little bit bigger, faster, venture capital is just a tool to accelerate that. It all comes with a cost.The cost of bootstrapping is, sometimes you have to do customer support for longer. You have to do some of these roles where you can't bring in talent earlier. The cost of venture capital is, you give it back equity and control within your business. There's usually controls. You need approval to raise capital. You need approval to sell your business.So, everything comes with a cost, and it has pros and cons. I think bootstrapping makes sense for 99% of entrepreneurs, because the bar today is building a billion dollar business, and that's not easy to do. So, for many first-time founders, I'm a big fan of stair-stepping and entrepreneurship. One of my favorite tweets that I've ever written is, “Start with an agency, get to cashflow positive, and then bootstrap an asset—whether that's a SaaS company or your e-commerce business—sell that asset, become financially secure, and then do whatever you want.” Swing for the fences, go on a beach, whatever. Along the way, you prepare yourself for the next stage of business.01:02:24 Nathan:Yeah, I completely agree with that. I have an article titled “The Ladders of Wealth Creation” that touches on the similar idea of using the skills from one ladder to move up to the next, and go from there.Well this has been fun. I always enjoy watching the partnerships, what you're doing on Twitter, and everywhere else.I think that MicroAcquire is a great example of what you can build with an audience. Thanks for coming on and hanging out with me and, and we'll have to talk soon.01:02:52 Andrew:Yeah, Nathan, thanks for having me, man. I enjoyed the chat.01:02:55 Nathan:Alright. Catch you later.01:02:56 Andrew:See you, man.

Andrew Warner has been part of the internet startup scene since 1997. Andrew and his brother built a $30 million per year online business, which they later sold. After taking an extended vacation and doing some traveling, Andrew started Mixergy. Mixergy helps ambitious upstarts learn from some of the most successful people in business.Andrew and I talk about his new book, Stop Asking Questions. It's a great read on leading dynamic interviews, and learning anything from anyone. We also talk about longevity and burnout as an entrepreneur. Andrew gives me feedback about my interviewing style, the direction I should take the podcast, and much more.In this episode, you'll learn: Why you need to understand and communicate your mission How to get your guest excited about being interviewed What to do instead of asking questions How to hook your audience and keep them engaged Links & Resources ConvertKit Gregg Spiridellis JibJab Ali Abdaal The Web App Challenge: From Zero to $5,000/month In 6 Months Groove Zendesk Help Scout Jordan Harbinger Noah Kagan Bob Hiler Seth Godin Morning Brew Alex Lieberman Keap (formerly Infusionsoft) Notion Sahil Bloom Ryan Holiday Brent Underwood Ghost Town Living Trust Me, I'm Lying: Confessions of a Media Manipulator Damn Gravity Paul Graham Y Combinator Nathan Barry: Authority Ira Glass NPR This American Life Barbara Walters Richard Nixon interview Oprah interview with Lance Armstrong Matt Mullenweg Chris Pearson Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue Peter Thiel Gawker Nick Denton The Wall Street Journal Rohit Sharma SanDisk Jason Calacanis Dickie Bush Sean McCabe Daily Content Machine Jordan Peterson Tribes Warren Buffet Sam Walton Ted Turner GothamChess LinkedIn Learning (formerly Lynda.com) Inc.com: Selling Your Company When You're Running on Fumes Chess.com Mark Cuban James Altucher Rod Drury Andrew Warner's Links Andrew Warner Stop Asking Questions Mixergy Episode Transcript[00:00:00] Andrew:The top 10 interviews of all time are news-based interviews. We, as podcasters, keep thinking, “How do I get enough in the can, so if I die tomorrow, there's enough interviews to last for a month, so I can be consistent, and the audience loves me.”That's great, but I think we should also be open to what's going on in the world today. Let's go talk to that person today. If there's an artist who's suddenly done something, we should go ask to do an interview with them.[00:00:32] Nathan:In this episode, I talk to my friend, Andrew Warner, who I've known for a long time. He actually played a really crucial role in the ConvertKit story in the early days, and provided some great encouragement along the way to help me continue the company, and get through some tough spots.We actually don't get into that in this episode, but it takes an interesting turn because we just dive right in.Andrew's got a book on interviewing. He runs Mixergy. He's been, running Mixergy for a long time. We talk about longevity and burnout, and a bunch of other things. He dives in and challenges me, and gives me feedback on my interviewing style. Where I should take the Podcast, and a bunch of other stuff. It's more of a casual conversation than the back-and-forth interview of how he grew his business. But I think you'll like it. It's a lot of what I'm going for on the show.So anyway, enjoy the episode.Andrew, welcome to the show.[00:01:25] Andrew:Thanks for having me on.[00:01:26] Nathan:There's all kinds of things we can talk about today, but I want to start with the new book that you got coming out.This is actually slightly intimidating; I am interviewing someone who has a book coming out about how to be good at interviewing. Where do we even go from here? You were saying that you have thoughts?[00:01:47] Andrew:I have feedback for you. I have a thoughts on your program.[00:01:51] Nathan:I'm now even more nervous.[00:01:52] Andrew:I've been listening, and I've been following, and I've been looking for questioning styles. Is there feedback I could give him? I mean, I've wrote a whole book on it. I should have tons of ideas on that.I don't. Here's the thing that stood out for me watching you. There's an ease and a comfort with these guests, but I'm trying to figure out what you're trying to do with the Podcast. What is connecting them? Are you trying to bring me, the listener, in and teach me how to become a better creator who's going to grow an audience and make a career out of it? Or are you trying to learn for yourself what to do?How to become closer to what Ali Abdaal doing, for example, or Sahil Bloom? Are you trying to do what they did, and grow your audience? Or is it a combination of the two?I think the lack of that focus makes me feel a little untethered, and I know that being untethered and going raw, and letting it go anywhere is fine, but I think it would be helpful if you gave me a mission.What's the mission that Nathan Barry's on with the Podcast. Why is he doing these interviews?[00:02:56] Nathan:Oh, that's interesting. Because it's probably different: my mission, versus the audience members' mission.[00:03:05] Andrew:I think you should have a boat together and, but go ahead.[00:03:08] Nathan:I was going to say mine is to meet interesting people. Like that's the thing I found that, podcasts are the pressure from two sides, one as a creator, as an individual online, like I'm not going to set aside the time to be like, you know what, I'm going to meet one interesting person a week and we're just going to have a conversation riff on something like that.Doesn't happen the times that, you know, the years that I didn't do this show, I didn't set aside like deliberate time to do that. And then the other thing is if I were to set aside that time and send out that email, I think a lot of people would be like, I kind of had to have a busy week. I don't know that I've, you know, like yeah, sure.Nathan, whoever you are. I did a Google search. You seem moderately interesting. I'm not sure that I want to get on that.Like a, get to know[00:03:58] Andrew:They wouldn't and it would be awkward. And you're right. The Podcast gives you an excuse. I think you should go higher level with it though. I think you should go deep to the point where you feel vulnerable. I think what you should do is say something like this, isn't it. You have to go into your own into your own mission and say, this is what it is.And just, so let me set the context for why this matters. I think it helps the audience know, but it also helps you get better guests to give better of themselves. I talk in the book about how I was interviewing Greg spirit, Dallas, the guy who created jib, jab, you know, those old viral video, it was a fire video factory that also created apps that allowed you to turn your yourself into like a viral meme that you could then send to your friends.Anyway, he didn't know me. He was incredibly successful. He was, I think, person of the year, a company of the year named by time. He was on the tonight show because he created these videos that had gone viral. And yes. He said yes, because a friend of a friend invited him, but I could see that he was just kind of slouching.He was wearing a baseball cap. It wasn't a good position. And then he said, why are we doing this? And I said, I want to do a story. That's so important. That tells the story of how you built your business. Yes. For my audience. So they see how new businesses are being built online, but let's make it so clear about what you did, that your great grandkids can listen to this.And then they will know how to great grandfather do this and put us in this situation. And that's what I wanted. I wanted for him to create that. And he told me that afterwards, if he had known that that was a mission, he wouldn't have put his hat on. He said that after that, he started thinking about the business in a more in depth way, visualizing his great grandchild.And then later on, he asked me for that recording so that he could have it in his family collection. So the reason I say that is I want us to have a mission. That's that important that yes. You could get somebody to sit in front of the camera because you're telling me you're doing a podcast, frankly.Right. You're with ConvertKit they're going to say yes, but how do you bring the best out of them? And that's it. And so that's why I'm doing this. And so one suggestion for you is to say something like.I'm Nathan, I've been a creator my whole life, but I'm starting from scratch right now with YouTube.I've got 435 people watching YouTube. It's not terrible, but it's clearly not where I want to end up. And so what I've decided to do is instead of saying, I've created the book authority, I wrote it. I'm the one who created software that all these creators are using a ConvertKit. Instead of, instead of allowing myself to have the comfort of all my past successes, I'm going to have the discomfort of saying, I don't know what it's like.And so I'm going to bring on all these people who, because maybe I've got credibility from ConvertKit are going to do interviews with me. And they're going to teach me like Alia doll and others are going to teach me how they became better creators, better business people. I'm going to use it to inform my, my, growth on YouTube.And by the way, You'll all get to follow along. And if you want to follow along and build along with me, this is going to come from an earnest place. Now I've obviously gone. Long-winded cause I'm kind of riffing here, but that's a mission. And now we're watching as you go from four to 500, now we care about your growth.Now there's someone giving you feedback and more importantly, there's someone who then can go back years later and see the breadcrumbs. Even if the whole thing fails and say, you know what?Nathan made it in virtual reality videos. And he's amazing. But look at what he did when YouTube was there. He clearly didn't do it, but he aspired right. I could aspire to, if I don't do it, I'll do it in the next level. That's that's what I'm going for with it. I talk too much sometimes and give people too much, too much feedback. How does that sit with you?[00:07:14] Nathan:I like the idea. I particularly love anytime a creator's going on a journey and inviting people along for it, right. When you're sitting there and giving advice or whatever else, it's just not that compelling to follow it unless there's a destination in mind. So I did that with ConvertKit in the early days of, I said, like I called it the web app challenge said, I'm trying to grow it from zero to 5,000 a month in recurring revenue.Within six months, I'm going to like live blog, the whole thing. people love that another example would be also in the SAS space, but, the company grew, they did a customer support software and they, I think. They were going from 25,000 a month to 500,000 a month was their goal. and they even have like, in their opt-in form, as they blogged and shared all the lessons, it had like a progress bar.You'd see, like MRR was at 40,000,[00:08:08] Andrew:Every time you read a blog post, you see the MRR and the reason that you don't remember what the number was is I believe that they changed it, you know, as they achieve the goal, they, they changed it to show the next goal on their list. And yeah, and you've got to follow along now. Why do I care? The groove, HQ or groove is, is growing a competitor to Zendesk and help scout.But now that I'm following along, I'm kind of invested now that I see how they're writing about their progress. I really do care. And by the way, what is this groove and why is it better than help scout and the others? Yeah. I agree with you. I think that makes a lot of sense. I think in conversations also, it makes a lot of sense.I think a lot of people will come to me and say, Andrew, can I just ask you for some feedback? I'm a student. Can I ask you for support? It's helpful for them to ask, but if they could ground me in the purpose, if you could say to somebody I'm coming to you with these questions, because this is where I'm trying to go, it changes the way that they react.It makes them also feel more on onboard with the mission. I have a sense that there is one, I'm just saying nail it, you know, who does it really good? who does a great job with it is a Jordan harbinger. He starts out his each episode is almost if you're a fan of his, it's almost like enough already. I get that.You're going to do an opt-in in the beginning of the Podcast. I get that. What you're trying to do is show us how to whatever network now and become better people. But it's fine. I'd much rather people say, I know too much about what this mission is. Then I don't.[00:09:26] Nathan:Do you who's afraid anyone else tuning in? What, what is Jordan's mission? What would he say is the mission that[00:09:32] Andrew:It's about, see, that's the other thing I can't actually, even though I've heard it a billion times, he's adjusted it. It's about, self-improvement making me a better person better, man. And so the earnestness of that makes me accept when he brings somebody on who's a little bit too academic who's, Jordan's interested in it or a little bit too practical to the point where it feels like I'm just getting too many tips on how to network and I don't need it, but I've got his sensibility.He's trying to make me a better person. And so I think with interviews, if you, if you give people the, the mission, they'll forgive more, they'll accommodate the largest and it does allow you to have a broader, a broader set of topics.[00:10:14] Nathan:Yeah. I'm thinking about the mission side of it. Like all of that resonates. and I love when an interview is questions are Like are the questions that they specifically want to know? It's not like I went through my list and this seems like a good question to ask instead. It's like, no, no, no, Andrew specifically, I want to know what should I do about, this?And I'll even call that out in a show and be like, look, I don't even care if there's an audience right now. Like this is my list, you know?[00:10:41] Andrew:Yes.[00:10:41] Nathan:But the, like if we dive into the mission, the one that you outlined doesn't quite resonate. And I think the reason. I think about, creators who have already made it in some way.And it starts to lose that earnestness. Like, honestly, I'm not that interested in, in growing a YouTube[00:11:00] Andrew:I don't think that that's I don't think that that's it for you. It's true. That's a little bit too. I don't know. It's it's a little, it's a little too early in the career. There is something there. I don't know what it is and it can't be enough. It can't be enough to say I need to meet interesting people because that's very youth centric and I'm not on a mission to watch you, unless you're really going to go for like the super right.And we're constantly aspiring, inspiring. the other thing it could be as you're running a company, you're trying to understand what's going on. No Kagan did that really well. I actually have the reason that I know this stuff is in order to write the book. I said, I have all my transcripts. I can study all the ways that I've questioned, but I also want to see what other people have done.And so Noah Kagan did this interview with an NPR producer. I had that transcribed to understand what he did and what he learned. One of the things that he did in that, that made that such a compelling interview is. He was a podcaster who wanted to improve his podcasting. And he, I think he even paid the producer to do an interview with him on his podcast so that he could learn from him.Right. And in the process, he's asking serious questions that he's really wondering. He's trying to figure out how to make a show more interesting for himself. Now. Clearly someone like me, who wants to make my Podcast more interesting. I'm like mentally scribbling notes as I'm running, listening to the podcasting.Oh yeah. The rule of three, like what are the three things you're going to show me?Well, yeah, at the end he did summarize it and he did edit. I don't like the edits at all because the edits take away some of the rawness of it and the discomfort which I personally enjoy, but I see now how he's editing it out.And it's, it's interesting to watch that progress.[00:12:32] Nathan:Yeah, I'm thinking through. The different angles that I could take with this. cause I like it and I feel like there's a, a thread that's not quite there. And I felt that on the show. Right. Cause people ask, oh, why are you having this guest on versus that guest? and it is that like, I, I find them interesting.There's also another angle of like probably half the guests maybe are on ConvertKit already. And so I want to highlight that. And then the other half of the guests aren't and I want them on ConvertKit and so that's an, you know, an incredibly easy, I can send you a cold email and be like, Andrew switched to ConvertKit.Right. Or I could be like, Hey, you know, have you on the show, we could talk. and we've gotten great people like in the music space and other areas from just having them on the show and then[00:13:18] Andrew:Can I give you, by the way, I know it's a sidetrack and I give you a great story of someone who did that. Okay. it's not someone that, you know, it's a guy who for years had helped me out. His name is Bob Highler every week he would get on a call with me and give me advice on how to improve the business.And then at one point he said, you know what? I need new clients. I want to start going after people who are, I want to start going after lawyers, helping them with their online ads, because lawyers aren't, aren't doing well enough.He started doing all these marketing campaigns because he's a marketer. And so one of the things he did was he got these cards printed up.He said, they look just like wedding invitations, beautiful. He, he mailed them out to lawyers. He got one, two responses. Like nobody would pay attention to a stranger, even if they were earnest and sending those out. And he goes, you know, and then he gets on a call. He doesn't even know what to say to people.If he just cold calling goes, I'm going to try to do that. And Andrew, I'm going to do an interview show for lawyers. He picked bankruptcy lawyers. He started asking them for interviews. They were all flattered because they also want another good Google hit. Right. And so they said yes to him and he asked them questions.Then I started learning the language. I forget all the different terms that he learned about how, about how they operate. But he said, inevitably at the end, they'll go after it was done. And say, by the way, what are you. And then he'd have a chance to tell them. And because he's built up this rapport and they trust him, they were much more likely to sign them.He signed up his customers, just like that, just like that. It's a, I think it's an, it's an unexplored way of doing it, of, of growing a business, taking an interest in someone, shining a light on them, helping them get that Google hit and helping them tell their story. And then by the way, will you pay attention to the fact that I've got a thing that if you like me, you might like also,[00:14:50] Nathan:So a few years ago, I was in New York and Seth Goden had come out to speak at our conference and he'd ever said, Hey, if you're in New York and want to make the pilgrimage up to Hastings on Hudson, you know, of outside the city, like come up and visit. And so I did that and it's so funny, cause it is like this pilgrimage to you, you like take the train up along the river. You know, I don't know what it is an hour and a half outside of the city. and I was asking Seth advice at his office, about like how to reach more authors. I think that was the question I asked him specifically and he just, he was like, well, what do authors want? And I was like, ah, I, some more books I guess.And he's like, yeah know. And so like we went through a series of questions, but he's basically what he came to was, find a way to get them attention so that they can grow their audience to sell more books. And he was suggesting a podcast is the way to do that. What's interesting is that's the side, like that's the other half of it, right.I want to meet interesting people. I want to, Like get more of those people that I find really interesting on ConvertKit pushed the limits of like, our customer base in, in those areas. And then the third thing is I want to do it in a way that's high leverage in my time. Write of, I want to do it.That creates something, for people watching and listening along so they can follow the journey. But I still don't see,I would say two thirds of that is about me, right?[00:16:18] Andrew:It's not only that, but all these things are byproducts more than they are the clear goal. You're going to get that. No matter what, if you just talk all day about what? No, not talk all day. If you do, what was it? I'm the founder of morning brew does nothing, but like a 15 minute, if that sometimes five minutes.[00:16:37] Nathan:Alex Lieberman.[00:16:38] Andrew:Yeah, just what, what goes on in his life now it's changed over the years or so that he's done it, but it's just, here's what we were thinking about today. Here's how I'm deciding to hire somebody BA done. He's just doing that. That's enough to get attention enough to also broaden his audience enough to bring us in and then so on.So I think if you just did nothing, but get on camera and talk for a bit, you'll get that. But I think a higher leverage thing is to tap into that personal mission and let all the others come through along the way and all the other benefits, meaning that you will get to meet people and change the way you think you will get to get people to switch to convert kit.And so on, by the way, that's such a, like an impressive thing for you to admit, to say, I want to have these guests on because I want to assign them up. I think a lot of people would have those ulterior motives and[00:17:23] Nathan:Oh, no, you got to just talk about, I mean, that's something you and I, for as long as we've known each other have been very, very transparent in both of our separate businesses and our conversations and it's just, everyone wants that. Right? Cause they're like, I think I know why Nathan is doing this, but he wants.And that would be weird, but if we go to the mission side of it, there's mission of like this, I'm going to improve the world side of mission, which definitely exists that can protect you. And I got my little plaque behind me. It says we exist to help creators are living. And so we can take that angle of it, thinking of like the, the goal journey side of things, since we're just riffing on ideas.One way that might be interesting is to make like a top 100 list of the top 100 creators we want on ConvertKit. And the whole podcast is about interviewing those people and reaching them. And, and so it could be like, this is what I'm trying to accomplish. And you're going to learn a whole bunch along the way as a listener, but you, you know, we check in on that.And then another angle that we could take that would be different is the, like we're going together. We're going to help the creator make the best version of their business. And so you make it more of a.We're both peers diving in on your business, riffing on it, you know, how would we improve it? that kind of thing.[00:18:43] Andrew:I think helping creators create a business, seems like something others have done, but not quite your approach, your style, the way that you will go and carve something is this is the thing that's over your head that says create. Is that something you carved in your wood shop? Then I saw on Instagram.Yeah, right. The sensibility of I've got to create it my way. Instead of that's a pain in the ass, I got a business to run who like, right. You're not going to see, for example, infusion soft, go, we need a plaque. Let's go to the wood shop. No, you're not. It's just not their sensibility. Right. Coming from a sensibility of someone who cares about the details, who every button matters in the software, everything behind your shoulder matters to you for yourself, even the stuff I imagine.If you look forward would have a meaning there, it wouldn't be random chaos. Is it random chaos in front of, on the[00:19:32] Nathan:The desk is random chaos, but there's a sign that says the future belongs to creators up there. And[00:19:38] Andrew:Okay. I think I might've even seen that online somewhere. So I think that coming, coming from the business point of view, With a sense of creator's taste, I think is something that would appeal to a lot of people. For whom seeing, for example, my take on business would be completely abhorring. All I care about is where the numbers are and what it's like.Right. Well, even allium doll's take on, it would not be, would not be right, because he's much more about every movement needs to matter. He can't just have a checkbox in notion it Ellis has to fire off five different other things that notion because otherwise you're wasting time. Why type five things when you could type one, right.It's a different sensibility. And I think you've always done really well drawing in that audience. I remember talking to a competitor of yours who started around the same time, also done really well about why you were, you were really growing tremendously faster. and they said he nailed it. He nailed who his audience is.It's the bloggers. It's these early creators who, who didn't have. Who didn't have anyone speaking for them. And you did that. And I think maybe that's an approach to saying, look, we are creators. And the business of creation is, or the business of being a creator is evolving and we want to learn about every part of it.And then it's interesting to hear how somebody growing their audience in an interesting way. How is somebody thinking about writing? I love that you asked Sahil bloom about how long it took him to write. I know he talks about it a bunch, but it's, it's interesting to hear him go with you about how it is like a five hour, seven hour writing job for him, right.To write fricking tweets. He's writing tweets, right? You've got people just firing off the tweet. He's spending five, seven hours on it. And, and he's also not a guy who's just like, right. It would be something if he was still in school playing baseball, and this is his intellectual, whatever. No, he's now running in investments.He's making decisions. He's helping promote his, his portfolio companies and he's spending five hours writing and he's doing it like one a week instead of one an hour. Right. It's all very interesting. And that approach, I think, ties completely well with ConvertKit.[00:21:41] Nathan:Okay. So where does that take us on like the mission or the hook for the show? Cause we're.[00:21:48] Andrew:Okay. Here's what I would do. I would, I would just keep riffing go. My name is Nathan Barry. You probably know me from convert kit. I'm doing this podcast because I like to meet interesting people. And here's the thing I'm trying to do or I'm I I'm doing it because I'm compelled to talk to these people who I admire.And I also want to learn from them about how they create and just riff on it. Like every week, even have every interview have a different one, until you feel like, oh, that's the one that feels just right. But if we just here, I want to have this person on, because I'm trying to learn this thing. I want to have this on because secretly I'm trying to see if I can get him to be at, see if I can get Ryan holiday to actually be on convert kit.Right. Boom. Now, now we're kind of following along as you're figuring it out. And that's also[00:22:29] Nathan:Yeah.[00:22:29] Andrew:The way, is Ryan holiday going to be on here or what?[00:22:31] Nathan:On the show,[00:22:33] Andrew:Yeah.[00:22:34] Nathan:Probably we were just talking the other day. We have a shared investment in a ghost town, So we, we often talk about that,[00:22:40] Andrew:Oh yeah. I've[00:22:42] Nathan:Other thing[00:22:43] Andrew:That ghost town. Oh, that's a whole other thing I've been watching that[00:22:45] Nathan:I need to have speaking of the ghost town, I didn't have Brent Underwood on because that Is an insane story of everything going on with town, but it's just been building this massive audience.[00:22:58] Andrew:Who's doing YouTube videos from there? He[00:23:00] Nathan:Yeah. And he's now got 1.2[00:23:01] Andrew:Yeah,[00:23:02] Nathan:Subscribers on YouTube, like 2 million on[00:23:04] Andrew:I had no idea. I watched him in the early days of the pandemic go into this place by himself. Almost get trapped, driving his car to get there. Right. I go, this is fun content. And usually when you watch someone like that and good morning, America go, and I'm going to jump out of this thing.And I've never jumped before, maybe whatever. I don't know.Yo, the producer's not going to let you die. It's fine. Here you go, dude. Who's just trying to get attention for this thing. Cause he has some investors who he wants to make sure get what they want. Yeah, you could die. What the hell is you doing?What? Like I'm going to, I'm going to go down this hole and see if there's anything over you yet. Dude, you could[00:23:41] Nathan:Yeah. It's, it's pretty wild. I actually, some of the weeks that he don't, he, that he didn't post the videos. I'd like, texted him, be like, Brett, you're still alive because you know, the video was the way that we knew every Friday, like, okay, Good Brent. Still alive, everything. Everything's good. Anyway, I got to have him[00:23:58] Andrew:All right. If you do talk to, if you talk to Ryan holiday, I feel like you totally nailed his writing style, where you, you said in one of your past episodes that he can take a whole historical story, sum it up in two sentences to help clarify the moment that he's writing about. And it's like a toss away thing, right? Just toss it away and then move on and go, dude. That's a whole freaking book. In fact, just turning the whole thing into just two sentences to fit in there would take silo, bloom five hours. You put it in a book with other, like there a bunch of other sentences. So that's good. But here's what I think you should talk to him about.Or here's my, my one suggestion. He has not talked about Marketing since he created, trust me. I'm a lot. Trust me. I'm lying, which was a phenomenal book that then I feel like he distanced himself from when he became more stoic and more intellectual. Fine. He is still a great, great marketer along your style, your tasty.And in fact, he's becoming the people who I can think of that are very, ConvertKit like philosophy in their creation plus promotion. He nails it, right? Art that takes so much pain that you've mentioned, and we've all seen it. He has boxes of index cards to create these sentences that most people would just throw away, not pay attention to, but are super meaningful.And at the same time, he knows how to promote. He knows how to get his ideas out there. He knows how to sell a coin that says you're going to die in Latin, that people put in their pockets that are more than just selling a coin. It's selling this transferable viral, real life thing. Right. So anyway. And is he should be on a ConvertKit too.[00:25:29] Nathan:He is, he is[00:25:30] Andrew:Okay. Good.[00:25:31] Nathan:Half of his list started in Berkeley. The other half are in the process of switching over. So, you know,[00:25:36] Andrew:Okay. Yeah, that's the hard part, dude. I I'm with infusion soft. I can't stand them. If you understand how much I do not like them. I do I ever talk negatively about anyone. No. Bring up politics, Joe Biden, Donald Trump. I got no strong opinion about anything you talked to me about, about infusions. Ah, but the problem is it's so hard to wean yourself off of these things because once you're in a system, that's it[00:25:56] Nathan:Well we'll make it happen. W w we'll figure out a way, but the new book landing page for it, I went on there and inspected element. It's definitely a ConvertKit for them. I was pretty happy about it.[00:26:06] Andrew:Oh yeah, yeah, yeah, yeah. So truthfully it was, I said, I'm not going to school around here. It would have probably been easier for me to go with, with infusion soft because then we all we'd have to do with tag people who were interested. And then I could, I don't want that. I don't want that nonsense because it comes with overhead.That becomes an obstacle to me, communicating with my audience by, by overhead. I mean, they've got historic legacy. Requirement's that mean I can't do anything right. You I'm on my iPad. I could just go in and send a message out. Or actually I haven't sent a message out. Someone else has sent a message out.Our publisher sent a message then from damn, ah, damn gravity. But I, but if someone says there's a problem, I can go in and see it.[00:26:44] Nathan:Right.[00:26:44] Andrew:And make adjustments. The whole thing just fricking works. Right?[00:26:47] Nathan:So I want to talk about the book more. Let's talk[00:26:49] Andrew:Sure.[00:26:50] Nathan:And now I have you here.[00:26:52] Andrew:Ben needs, us to talk about the book. He's the publisher.[00:26:54] Nathan:We'll get to that, then don't worry. Ben, we've got it covered. so you were giving unsolicited feedback, which by the way is my favorite kind of feedback. Okay.So as you've been listening to the show, what are some other things that maybe you recommended the book, maybe like as you set people up for interview questions, any of that advice that you would give beyond?We started with the men.[00:27:15] Andrew:I'm going to suggest that people who listen to you do pay attention to this. One thing that they should, I I'm interrupting you in a roadway now there's some good interruption that I write about in the book and I can tell you how to do it. Right. And I also have to say that there's some new Yorker that's built in, even though I've left New York a long time ago, that I, I always interrupt when we need to get into the bottom line.Okay. Here's one thing that I think people should pay attention with you. You don't just ask questions. You will, at times interject your own story, your own, take your own experience. And I find that a lot of times people either do it in a heavy handed way. It's like, look at me, I'm equal to you. I deserve to be in this conversation too.And that doesn't just happen on Mike. It happens at dinner parties or it's more like I have to be reverential. So I'm asking questions and it's me asking about them. And one of the things that I learned over the years, Getting to know someone interviewing someone, whether it's like you and I are doing in our podcasts and shows or doing it, in a, in a dinner conversation, it's not asking questions.It's not about saying here's my next thing. Here's my next question. It's overwhelming and draining to do that. You do need to say, well, here's me. You do need to sometimes just guide the person to say, now tell me how you wrote the book. Now tell me how long it takes to, to write a tweet, right? Whatever it is, you need to sometimes direct the person.And so I call the book, stop asking questions because that counter intuitive piece of knowledge is something that took me a fricking interview coach to help me accept that. It's true, but it helps. And you do it really well. And here's why you do it. Well, you interject something personal. Somehow you do it succinctly.You don't get rambling off. Maybe you edit that.No, no, because the videos are there. Yeah. It's, it's not edited. It's just you saying here's, here's my experience with this. And then when you come back and you ask something. It informs the guest about where you are and what they could contribute to that. It lets them also feel like this is a dialogue instead of them being pounded with demands of, in the forms of question.[00:29:15] Nathan:Yeah. Yeah. I think that for anyone listening and thinking about starting a podcast, it's really like, what's the kind of thing that you want to listen to. And I like it where the host is like a character in the, in the Podcast, in the episode where they're contributing content and it's not just like, oh, if I listened to Andrew on these 10 shows, I'm just going to get Andrew.Like, I want it where it's like, no, I'm getting the blend between these two people. And the unique things that come from that intersection rather than, you know, I've heard this[00:29:46] Andrew:Yes.[00:29:47] Nathan:I've heard about it.[00:29:48] Andrew:I think also it took me a long time years of, so I started doing this in 2007, give or take a year and I think. No one needs to talk about, I don't need to talk about myself. They don't care about me. They care about, you know, Paul Graham, who I'm interviewing about how he found a Y Combinator, someone.And I would get tons of emails from people saying, tell us who you are. Tell us a little bit about yourself. And I would argue with them and say, no, but I understand now on the outside, when I listen, I don't know who you are. And it feels very awkward to hear it. It feels very much like, I don't know why, where you're coming from.And so I don't know why I should listen. It's kinda, it's it's counterintuitive.[00:30:29] Nathan:Yeah. I think it just comes with comfort over time. Like, I, I don't know this for sure. If I bet if I listen back to my first podcast episodes, the ones that I did in like 2015. I have a different style because I bet I'm less comfortable or more worried about like, make sure that I shut up quickly so that the guests can talk more because people came here for the guest and then over time you just get more comfortable.[00:30:53] Andrew:So you wrote authority and I remember you, I remember buying it and I remember you bundled it with a bunch of stuff, right. And oh, by the way, it's so cool. I was listening to it on a run and I heard you mention my name in the, in the book I go, this is great and I'm running. but I remember you did interviews there.I don't remember whether the style matches up to today or what, but you did interviews in it. Right.[00:31:15] Nathan:I did.[00:31:16] Andrew:And what you had there that I think is always important to have with all, all interviews is you had a sense of like, well, the sense of mission, I knew what you were going for, because you were trying to say, here is this book that I've written on this topic.I'm want to bring these people in to bring their, their take on it. We were all kind of working together. And I feel like, when I look at my earlier interviews, I listened to them. The Mike sucks so badly. I was too ponderous. Cause I wanted to be like, IRA glass from, from NPR, from this American life.And you could hear the same rhythm, the same cadence, like I'm copying him. Like I'm his little brother trying to learn how to be like a real boy. but I had this real need. I was trying to figure out how these people were building companies that work to understand what holes I had in my understanding to see what was working for them that I didn't know before.And you could see that and it, it helps. It helped me continue. Even when I was nervous with the guest, it helped the guests know where to go. Even when I wasn't doing good job, guiding them and help the audience keep listening in, even when the audio stopped, because there's this thing that Andrew is trying to understand.And you almost feel like you're the sense of vulnerability. If it doesn't scare you away, then it makes you want to root.[00:32:40] Nathan:Yeah. And I personally love that style because I want to follow someone going on a journey and, and trying to accomplish something specific. But let's talk about the not just the book, but asking questions or in this case, stopping it, stop asking questions. What are the things that not even just specific to this job, what are the things that you listened to interview shows?And you're like, okay, here are the three things that I want to change or that I want to coach you on in the same way that I was coached on.[00:33:10] Andrew:Okay. So what I started to do is I go through my own transcripts. I mean, I had years of transcripts to see what worked and what didn't I already done that. So I said, I need to now add to it. And so I went back and looked at historical interviews, like when Barbara Walters interviewed Richard Nixon and got him so frustrated that he didn't want to ever talk to her again.Or when Oprah finally got to sit with Lance Armstrong, how did she do that? I think. You know, you know, let me pause on, on Oprah and Lance Armstrong. She got to interview him after he, he was basically caught cheating and he was about to come out and do it. Great. Get, I think the fact that she interviewed him, there's a lesson there for, for all of us who are interviewing, interviewing the top 10 interviews, I think of all time.And you go back to Wikipedia and look it up. You see art or interview podcast or interview, sorry, our news-based interviews. We as podcasters, keep thinking, how do I get enough in the can so that if I die tomorrow, there's enough interviews to last for a month or whatever, so that I can be consistent in the audience loved me.That's great. But I think we should also be open to what's going on in the world today. Let's go talk to that person today. If there's an artist who suddenly done something, we should go and ask to do an interview with them. If there's a creator, if there's someone. So for me, one of the top interviews that people still it's been years, people still come back and talk to me about is when Matt Mullenweg decided that he was gonna pull out Chris[00:34:35] Nathan:Pearson.[00:34:35] Andrew:Per Pearson.Pearson's, themes from WordPress. And I got to talk to both of them at the same time and I published it and it went all over the internet with all over the WordPress internet. So hundreds of different blog posts about it, eventually all the people in the WordPress world write a lot of blogs, but also it became news.And so we don't do enough of that.[00:34:57] Nathan:I remember that interview because I was in the WordPress community at that time. And I remember you saying like, wait, I'm in Skype and I have both of you in two different things and you pull it together and not to pull Ryan holiday into this too much, but that's where he ended up writing the book.Was it, he realized he was one of the only people who was talking to like both Peter teal and, who's the Gawker guy.Yeah. Anyway, people know, but, but being in the intersection of that, so you're saying find something that's relevant on the news[00:35:33] Andrew:Yeah. Nick Denton was the founder of Gawker. Yes. Find the things that are relevant right now. And when people are hot right now, and they know you and you have credibility in this space, they trust you more than they trust. Say the wall street journal, even right, where they don't know where's this going.I think that's, that's one thing. The other thing is I think we don't have enough of a story within interviews. If we're doing S if we're doing at Mixergy, my podcast and interview where we're telling someone's story, we want them to be somewhere where the audience is at the beginning and then to have done something or had something happen to them that sets them on their own little journey.And then we make this whole interview into this. Into this a hero's journey approach. So I think better when I have an actual company in mind, so, or a person in mind. So last week I was interviewing this guy, Rohit Rowan was a person who was working at SanDisk, had everything going right for him. His boss comes to him and says it, you're now a director, continue your work.But now more responsibilities he's elated. He goes back, home, comes back into the office. Things are good, does work. And then a couple of days later he's told, you know, we mean temporarily, right? And he goes, what do you mean? I thought I got, I got a promotion. No, this is temporary. While our director's out you're director of this department.And then you go back, he says, the very next day, he couldn't go back into the office. He sat in his car, just, he couldn't do it anymore. And so he decided at that point, he'd heard enough about entrepreneurship heard enough ideas. He had to go off on and do it himself. And so we did. And then through the successes and failures, we now have a story about someone who's doing something that we can relate to, that we aspire to be more.[00:37:13] Nathan:So, how do you, you, your researchers, how do you find that moment before you have someone on? Because so many people will be like, yes, let me tell you about my business today. And oh, you want to know about that? How'd, you know, you know, like, as you,[00:37:27] Andrew:Yeah,[00:37:28] Nathan:That hook in that moment? That actually is a catalyst in their own dream.[00:37:33] Andrew:It's tough. It's it takes hours of talking to the guest of, of looking online of hunting for that moment. And it takes a lot of acceptance when it doesn't happen. One of my interview coaches said, Andrew, be careful of not looking for the Batman moment. And I said, what do you mean? He goes, you're always looking for the one moment that changed everything in people's lives.Like when Batman's parents got shot. And from there, he went from being a regular boy to being a superhero. Who's going to cry, fight crime everywhere. His life doesn't really work that way. There aren't these one moments, usually the change, everything. So I try not to. Put too much pressure on any one moment, but there are these little moments that indicate a bigger thing that happened to us.And I look for those and I allow people to tell that without having it be the one and only thing that happened. So if Pharaoh, it, it wasn't that moment. It could've just been, you know what, every day I go into the office and things are boring. And I think I have to stop. What I look for is give me an example of a boring.Now he can tell me about a day, a day, where he's sitting at his desk and all he's doing is looking at his watch, looking at his watch and he has to take his watch, put it in his drawer so that he doesn't get too distracted by looking at his watch all day. Cause he hates it. Now was that the one moment that changed everything?It was one of many moments. It might've happened a year before he quit, but it's an indication. So when we're telling stories, we don't have to shove too much pressure into one moment, but I do think it helps to find that one moment that encapsulates their, why, why did they go on this journey? Why does someone who's in SanDisk decide he's going to be an entrepreneur?Why did someone who was a baseball player decide that he had to go and write a blog post? Why is it? What's the thing that then sends them off on this journey? It helps. And I would even say, if you can get that moment, it just helps to get the thing that they were doing before that we can relate to. So what's the thing that they did before.So anyway, we have two different types of interviews. One is the story-based interview where we tell a story of how someone achieved something great. And so that hero's journey is and approach. The other one is someone just wants to teach them. All you want to do is just pound into them for an hour. Give me another tip another tip another tip of how to do this.Like pound, pound, pound, pound pound. If you want the audience to listen. I think for there, it helps to have what I call the cult hook because I said, how do I, how do cults get people to listen to, to these people who are clearly whack jobs sometimes. And so studying one called I saw that what they did was they'd have a person up on stage who talked about how, you know, I used to really be a Boozer.If you came into my house, you would see that there'd be these empty six packs. I was so proud of leaving the empty six packs everywhere to show myself how much alcohol I can drink. My wife left me. And when she left me, she just told me that I hadn't amounted to anything in my life. And I was going nowhere.And I just said, get I here. Instead of appreciating that this was just like terrible. And I ran out of toilet paper and don't even get me started with what, what I did for that. And so you see someone who's worry worse off than you are on this path of life. And then something has. They discover whoever it is.That's the cult leader. And they say, now I've got this real estate firm I encouraged by, oh, by the way, all of you to come over and take a look at that at this, I couldn't believe it. My whole life. I wanted to buy a Tesla. I now have the Tesla S it's amazing. It's just so great. And I did it all because I changed the way I thought once I came in and I found this one book and the book told me, I mean, anyways, so what we try to do is we say, if you're going to have somebody come on to teach how they became a better blogger, let's not have them start over elevated where everything they do is so great that we can't relate, have them start off either relatable or worse.I couldn't write here's my grammar, mistakes. My teacher told. Right. And now what's the thing that they did. They pick them from where they were to where they are today. it's this real set of realizations. Now I want to go into that.Let's pound into them and see how many of those tips we can get. Let's learn that I want to go from where he was to where he is.[00:41:28] Nathan:Yeah, I liked that a lot. Cause my inclination would be like, okay, we're we're doing the, educational, tactical conversation. I'm going to facilitate it. Let's dive right in and let's get to the actionable stuff right away. So I like what you're saying of like, no, no, no. We need to, even though this is going to be 90% packed, full of actionable material, we need to dive in and set the stage first with the story and making it relatable.And I like it.[00:41:55] Andrew:Yeah,[00:41:55] Nathan:Oh, yeah. I was just, just in my own head for a second. Cause I say, ah, that makes sense a lot, so much so that I've had three different guests or listeners email me and say like, just don't say that makes sense as much would, now that I'm saying it on the show, I'll probably get more emails every time that I say it.Cause that's like my processing, like, oh, oh, that makes sense. As I'm thinking of the next question and all that, so[00:42:22] Andrew:I do something like that too. For me. It's IC,[00:42:25] Nathan:Everyone has to have something.[00:42:26] Andrew:I can't get rid of that and yeah.[00:42:28] Nathan:So what systems have you put in place on the research side so that you're getting this, are you doing pre-interviews forever? Yes. Are you having your[00:42:38] Andrew:Almost every single one, some of the best people in some of the best entrepreneurs on the planet, I'm surprised that they will spend an hour or do a pre-interview. And sometimes I'm too sheepish to say, I need an hour of your time and I need you to do a pre-interview. So instead of saying, I need you to do a pre-interview.I say, here's why people have done it. And I've paid for somebody to help make my guests better storytellers of their own stories. And truthfully people will go through that. Pre-interview even if they don't want to do an interview, they just need to get better at telling their story for their teams, their employees, their everyone.Right. and so I say that, and then they will take me up on the pre-interview and say, yes, I do want to do the pre-interview. and so what I try to do is I try to outline the story. Ahead of time in a set of questions. And then what we do is we scramble them up a little bit based on what we think people will tell us first and what will make them feel a little more comfortable.And then throughout the interview, I'll adjust it. So for example, no, one's going to care about the guest unless they have a challenge. No guest wants to come on and say, I'm going to tell you about what's what I really suck at or where I've really been challenged. If they do, they're going to give you a fake made up thing that they've told a million times to make themselves seem humble.So we don't ask that in the beginning. We don't even ask it in the middle. We save it till the very end. Now they've gotten some time with us. They've gotten some rapport, they trust us. Then we go into tell me about the challenges, what hasn't worked out for you. And we really let them know why tell people the higher purpose you want the audience to relate.You want them to believe you. You want them to see themselves in you, and to learn from you. We need. They tell us, and then I have it in my notes as the last section, but I use it throughout the interview. I sprinkle it. So the goal is to get the pieces that we want and in whatever order makes the most sense and then reshape it for the interview Day.[00:44:33] Nathan:So on the interview itself, you would, you would flip that and you know, okay, this is what I want to start with and, and dive in right[00:44:41] Andrew:Yup. Yup.[00:44:43] Nathan:Lose. They already told you about that. And so now, you[00:44:46] Andrew:Right,[00:44:46] Nathan:In and start with.[00:44:47] Andrew:Right. That helps. Now, if there's something I want to ask someone about that they're not comfortable with. One thing that I do is I, I tip them off. So Jason Calacanis invited me to go do, interviews with, with investors at one of his conferences. It was just a bunch of, investors. And I looked at this one guy, Jonathan tryst, and he looked really great.But he, what am I supposed to do? Ask him about what startups should do to run their businesses. He's never run a startup. His, he hadn't at that time had a successful exit. As far as I knew, like mega successful exit. He's just a really nice guy. You can tell he was going places, but that's it. And the money that he was investing came from his parents.So what is this rich parents giving their kids some money. Now he's going to tell everyone in the VC, in the startup and VC audience, how to live their lives. So I said, I'm either not going to address it, which I think most people are, or I have to find a way to address it where I'm not going to piss them off and have them just clam up on me and then go to Jason and go.This guy just is a terrible interviewer, which is not true. So what I decided to do was tip him off. I said, look, Jonathan, before we do this, before we start talking to the audience, I have to tell you, I saw it, that you don't have much of a track record as an investor. Your money came from your parents and you're not like a tech startup, like people here.If we don't talk about it, people who know it are going to think, oh, this guy, Jonathan, look, who's trying to pass him soft self off. I don't have to force it in here, but if you allow me to, I'd like to bring it up and let's talk about, and it goes, yeah, absolutely. If it's out there, I want to make sure that we address it and sure enough, we talked about it and he had a great answer.He said, no, this came from my parents. It's not my own money. I don't have as much experience as other people, but I took my parents' money. I invested it, fat parents and family and so on. We've had a good track record with it. And now have raised the second Fallon fund from outsiders who saw what I was able to do with the first one.And by the way, I may not have this mega exit as a startup investor, as a startup entrepreneur. But I did have this company that did okay. Not great. Here's what it did Here's what I learned And that's all informing me. And that's where I come from now. You've got someone talking about the, the, the thing that matters without pissing them off so much that they don't say anything else.And you feel like you feel superior as an interviewer. I got them. But in reality, you got nothing[00:46:57] Nathan:Right.[00:46:57] Andrew:Cares.[00:46:58] Nathan:I think that's a really hard line of talking about the things that are difficult and like the actual, maybe things that someone did wrong or lessons that they learned without just like barely dipping into it for a second. And I liked the format of tipping them off in like full transparency.So on this show, I had someone on who I really, really respect his name's Dickie Bush. He's one of the earlier episodes in this series and in it, he, okay. Yeah. So in that interview, one thing that I knew is that his, the first version of his course plagiarized text from another friend, Sean McCabe, actually Shaun's company edits is Podcast and all that.And I've known both of them for, for quite a while. I've known Sean for like, I dunno, six, seven years or something. And I was like, struggling with how to bring that up. And I wanted from the like founder, transparent journey, that sort of thing I wanted it brought up because I, I actually like, I'm happy to talk about like some pretty major things that I've screwed up and what I've learned from it.And I just think it makes a better conversation. And then from the interview side, I don't feel good, like doing an interview and not touching on that, but I didn't tip Dickey off to it. And I, that was one of the things that I've regretted that he gave a great answer. He talked about the lessons that he learned from it.It was really, really good, but I felt bad that I didn't set him up for the most success in like in setting up. And part of that, part of it is because even at the start of the interview, I was still wrestling with now, I'm not going to bring that up that, ah, maybe I should, it wouldn't be an authentic interview if I didn't like wrestling with that, I hadn't figured out my own, like made my own decision until we were in the middle of it.And so I didn't, I didn't set anybody up for success. And so it's an interesting line.[00:48:52] Andrew:It happens. And it seems like I'm now in the point of your transcript, where you, where you ask him, it's a 31 minutes into the interview. I think his response is great. He came in and he took responsibility for it. He says, yeah, that, that, that was a dramatic mistake, or a drastic mistake on my side and caught up in it.He wasn't the most articulate here and he'd repeated words. Like I, I, a couple of times, so I could see that he probably was uncomfortable with it. but I think his answer was great. I think, I believe that we all are broadcasting out, whether we know it or not, our intentions and where we're coming from, as some people are really good at faking it.And so I'm not going to talk about the outliers and some people are so uncomfortable that they're messing up the transmission, but for the most part almost. broadcasting our intentions. If you walk into that, Nathan, with the, I got to get him because he, he got one of my friends and I need him to finally get his comeuppance.He's going to pick up on that. And truthfully, it's such a small thing for a person like you who's, who's already a likable person. You have a lot to offer people, right? As far as like promotion and everything else, it will be forgiven, but it'll be picked up on, it's also something that people could pick up on, which is Nathan really want to know this thing.It's been bothering him for a while. And if you could, just, before you asked the question, say, where am I coming from with this? And know that the audience will mostly pick up on it. And obviously people are gonna like read in whatever they feel like, but trust that the vast majority of us understand, I think it'll work[00:50:21] Nathan:Yeah,[00:50:22] Andrew:You don't have to even tip. You don't have to tip off, but it does help. It, it definitely helps.[00:50:26] Nathan:It's interesting. I was watching an interview with, Jordan Peterson who wrote 12 rules for life. He's like a very controversial figure. And I was just often these controversies pass by, on Twitter and other places. And I realized like, oh, I don't understand them. And rather than jumping on one side or the other, at least try to like dive in a little bit and understand it.So watching this interview, and I can't remember, I think it was some major Canadian TV show or something, and that you would tell the interview was just trying to nail him it every possible chance, like whatever he said, just like dive in. And, so I think you're right, that you see the intention, like in that case, you would see the, the interview, his intention was specifically to try to trip him up in his words.And then in other cases where it's like, This is something that, you know, if you take the other approach, this is something that's been bothering me, or I want to talk about it. Like I genuinely want, you know, to ask or learn from this. It's a very different thing.[00:51:20] Andrew:I think people pick up on it. I remember you, you mentioned Seth Godin. I remember interviewing him when he wrote the book tribes back before people had online communities. And I didn't just say, okay. All our heroes, all the best entrepreneurs just run their businesses. Then don't run a tribe. I brought out books.I said, here's a book about Warren buffet. Here's the book by Sam Walton. The Walmart here's a book by Ted Turner became a multi-billionaire to creating all these, these media empires didn't have communities. They don't have tribes. And now you're telling me that in addition to my job, I also have to go and build out a tribe.It feels like, you know, an extra job. That just seems right for the social first. This just sounds right on social media and you could actually see. He's watching me as I'm saying it, and he's smiling, he's watching it because he's trying to read me, is this like what I get wrapped up? Is this going to be some kind of thing where some guy's going to try to be in the next Gawker media?Or is, is this a safe place? We're all doing that constantly. And then he also saw, okay, this is someone who really wants to understand this. And he's challenging me. I like a challenge. And you could see him smile with like, this is what I'm here for. And so I think when you come at it from a good point of view, people can see it and then you can go there and you can go there and you can go there and it will be shocking to you and them and the audience, how far you go. But when you're coming from that genuine place, they get, they get it.They want it.[00:52:44] Nathan:Yeah, that's good.I want to talk about longevity in like the online world. I think that so many people that I started following in say 2007, 2008, nine, and then I didn't start creating myself until 2011. most of them aren't around anymore. Like a lot of the big blogs, Yeah, just so many that I can think of.They're not around anymore. They're not doing this. You're at a point where like you started messaging in some form in what? 20, sorry, 2004 to somewhere in there and then interviews.[00:53:17] Andrew:Yeah, I keep saying 16. It's like, yeah. 2004 is when I started the interview started 2007 ish somewhere there. Give or take a year. yeah, long. I, I will say that there are parts of my work that I am burned out on right now. This year has been that, but I'm not on the interview. And the reason I'm not is because I do enjoy conversations.I hated them for a long time in my life because I just didn't know how to have them, how to have it make sense. I also didn't give myself permission to take the conversation where I wanted it to go. And it helps now to say, I can talk to anyone about anything. That's an opportunity that, that feels fun because I know how to do it.It's an opportunity to, it feels like, like, you know how everyone's so happy. You can go to YouTube and you could get the answer to anything. Well, I could go to anybody and I could get the answer to anything and talk about how they didn't have a customized to me, YouTube, not customized thing to me, I'm watching Gotham chess on YouTube.He's teaching me how to play chess, but he will not customize to the fact that every time I get into a car con defense, all the pieces like bunched over to my side. But if he and I did an interview, or if I do an interview with an tomorrow's entrepreneur, it's going to be about, here's the thing I'm trying to deal with.How did you get past that? Talk to me about what you're up to there.[00:54:31] Nathan:Yeah, that's definitely energizing. Okay. But what are the things that you're burnt out on? Because I think a lot of people are seeing that burnout. And so I guess first, what are you burned out on? And then second, we can go from there into like, what are you changing and how are you managing.[00:54:46] Andrew:I'm burned out on parts of the business behind, behind Mixergy I'm burned out on. I was aspiring to like unbelievable greatness with the, with the course part of it, with the courses, it didn't get there and I'm tired of trying to make it into this thing. That's going to be super big. I'm tired of that.[00:55:10] Nathan:His greatness there, like linda.com? Like what, what was that?[00:55:15] Andrew:Yeah, yeah, yeah. Yes. Yeah. She was one of my first interviewees and, and so yeah, I saw the model there and I am frustrated that I didn't get to that and I, I don't have a beat myself up type a perso

Kimberly Brooks is a contemporary American artist and author. Kimberly integrates landscape, figuration and abstraction to address subjects of history, memory and identity. Her work has been exhibited and featured internationality.Kimberly received her bachelor's degree in literature from U.C. Berkeley, and was Valedictorian. She has taught art as a lecturer and adjunct faculty instructor, and was a featured speaker at TEDx Fullerton.In this episode, I talk with Kimberly about her work as an artist, author, and editor. We talk about how she uses ConvertKit to reach and grow her audience. We talk about what people can learn from fine art, and apply it to their newsletters. We also cover the path to becoming a successful creator, and much more.In this episode, you'll learn: The secret to achieving your breakthrough moment A job most creators should charge for, but rarely do What you should be doing instead of blogging Should you be posting on Instagram? Links & Resources Huffington Post ConvertKit Craft and Commerce Steve Jobs John Baldessari Adobe Photoshop Adobe Leonard Shlain Milton Glaser Macworld Walt Disney's Imagineering Warner Music Group Seth Godin Leonardo da Vinci Arianna Huffington Huffington Post: Fine Art Later Anderson Ranch Arts Center Otis College of Art and Design Kimberly Brooks's Links Find Kimberly on Instagram Kimberly's website Kimberly's Ted Talk Huffington Post article, “The Gap Logo, New Coke and the Legendary Walter Landor” Kimberly's book, The New Oil Painting Episode Transcript[00:00:00] Kimberly:The fundamental way to learn is, you imitate, assimilate, and then you can improvise with anything. You're going to be thwarted in the beginning many times, and you can't give up. You have to say, “Okay, well, I don't care if it sucks. I don't care if I'm going to fail. If I'm gonna fail, I'm gonna fail big. Let's just go on.”[00:00:29] Nathan:In this episode I talk to Kimberly Brooks. She is a fine artist. So, painting, she has all of her art in galleries, that whole world, which is super fascinating to me. She also plays in the creative world. Newsletters, podcasts, and interviews.She built the whole art editorial section of the Huffington Post. She built that to millions of readers. She's done all kinds of things in the design community from the early days. So, we riff on that; Mad Men-style ad agencies in the ‘80s and ‘90s. Some great stuff.Then she brings it all the way through to talking about what she does with ConvertKit. How she sets up her sequences, and everything else, and things that people can learn from fine art, and apply to their email newsletters and sequences.So, it's a fun episode. We have to do a part two, because we filled up all the time we had, and I think I only got through half my questions.So, anyway, I'm going to get out of the way and dive in. So, here we go.Kimberly, welcome to the show.[00:01:37] Kimberly:Thank you for having me, Nathan.[00:01:39] Nathan:There's so many things I to talk about, because you come to the creator world from a different perspective than I do, though we both share a love for Photoshop.[00:01:50] Kimberly:Oh, yeah.[00:01:51] Nathan:We'll start with where we met. It was at Craft and Commerce, some number of years ago.I can't even think. Three years ago? Four?[00:02:01] Kimberly:I think it was three years ago, and it was such a random whim. I don't even know how I ended up finding it. I fell in rabbit hole. And then I came upon ConvertKit.I was actively looking for a better way to send art show announcements. Because I'm a painter, I'm an artist.I just felt after my previous experiences, I knew how important having a subscriber-based service was. I don't want to get too nerdy, but I didn't really like the competitor who shall remain unnamed. But, I found you guys, and I started getting the advertisement for the conference, and it was in Boise, Idaho.And so I thought, I'll just go. It was like a Ted conference for really creative nerdy people like me, but it was exactly what I was wanting. It was about marketing, which is really such a weird word because it's really about sharing, and I loved the title.I loved everything about it. I met some of the people that I'm really, really close with now. Then the next year it was canceled because of the pandemic, but it was amazing, and I met you, actually.[00:03:28] Nathan:And, and we had a really fun conversation. one thing that I want to talk about, for you is the intersection between fine art, right. And painting and that world. And then now you're also in this world of being a writer and a creator in the sense, right. You you've been a writer and creative for a long time, but, but it's, it's like a different world of the selling things to your audience.And. Earning money directly in that way. And so I want, like, I want to hear that as you like weave in and out of these two worlds and then just your experience there.[00:04:02] Kimberly:Yeah, it's interesting. I, when I was in elementary school, we had a really competitive game of tetherball constantly going on on the playground. And it was just sort of that pole with a ball attached to a rope we would, people would line up and we would get it, and it was, see how many times, and it was just sort of like, it was very intense and I always felt like being an artist.Being an art to me was it was the pole, you know? So like my pole is art is making art and everything about what I do. I write about it. I interview people about it. I interview other artists about their work. I make paintings 90% of the time in my studio. Like, it's all about art, you know? So that's like the beginning.So I do see myself sashaying between different worlds. And I think everybody kind of does that. And then as the bicycle of technology was being built to use kind of like a vague reference to like Steve jobs is, you know, what happens if you put a man on a bicycle and you know, like how fast can he, as the bicycle was kind of entering our world, I thought, what if you kind of mixed art with the bicycle?You know, what, what happens if you, you know, Make an artist's website. So I was like one of the first people I knew that made an artist's website. And I remember, it was, I had, was having lunch with my mentor. Who's, the late John Baldessari. He was a great, great, great artist. And, he's famous for, you know, he burned all this stuff and graduate school and then became a conceptual painter, you know, very, you know, Howard work in, you know, conceptual anyway.So I brought my laptop to this Mexican restaurant in Venice, and I said, I wanted to show you something. I made a website and our studios were really near each other. And he said, Oh, I, I don't know if I would do that. If I were you, I was like, why not? He said, because you're, you'll piss off the dealers, the galleries, the galleries, you shouldn't be selling directly.It's going to take away from what their job is. You know, when you hang a show and you have art in the gallery, the gallery is selling the artist and it's their job, you know, and artists are supposed to be kind of this, you know, semi mute, black turtleneck wearing, you know, mysterious, mystical ShawMan goddess.I call it goddess on the hill. Like you're not supposed to really get in the way of what your artists about. And so I thought, oh gosh, you know, this is, and I had put the paintings for a show was about to have. And so I started making, so my postcard for that show had the name of the show and it had the name of the website, cause no galleries had website.Then this is in like the two thousands, you know, this is a long time ago. And I remember meeting people when I handed them a postcard. If like I felt comfortable with them, I would like secretly write a password so that they could see the website,[00:07:20] Nathan:Oh was you were, you had the website, but it was[00:07:24] Kimberly:Yeah. So I password protected it. I password protected it because John Baldessari told me that it's probably not a good idea to have a website.This is again, no artists ad website.[00:07:35] Nathan:How did the galleries and the community[00:07:37] Kimberly:The galleries didn't have websites either. And the galleries, I remember. They started it. Like some of them had websites, but it was super janky. It was like sometimes most of the time they did an, and it was just sort of this mysterious world that 99.9, nine, 9% of the public didn't understand.Doesn't understand it's better now. And you'd have to be walking down the street or you'd have to know somebody who knows somebody, you know, it's, it was just a different world then.[00:08:08] Nathan:But did any of those negative things come about? Like, did anyone look down on you on it for having a website and for[00:08:14] Kimberly:No, no, no. Eventually I just said, screw it. And I took the password off.And, interestingly, I don't want to date myself, but I think I already have, but the at the time flash was very. sexy. And it was like, and so artists would have, if they did have website, firstly, they would be horribly designed and they would have like a flash animation of a curtain opening and a door.And it was very like CD rom mentality. Like, you know, it was pre-internet thinking, you know, anyway, like I said, the big nerd here.[00:08:48] Nathan:Flash was big until 2000, like the iPhone 2007.[00:08:52] Kimberly:Until Steve jobs killed it, just took a knife. He took a sword and he just, during a keynote, just, you know,[00:09:01] Nathan:Yeah. Oh, and the two biggest reasons were, that the bandwidth of the phones couldn't handle it. And then also the battery life on the phones couldn't handle it.[00:09:10] Kimberly:Wasn't there another reason there was another technical reason that had to do with plays well with others. I can't remember exactly what it was,[00:09:20] Nathan:Yeah. I mean, it was a restricted technology. Like it was owned Macromedia. And so probably that apple was trying to do to get to play. And Adobe was playing hardball and apple was probably like, okay,[00:09:31] Kimberly:Yeah,[00:09:32] Nathan:You know, we'll play this[00:09:33] Kimberly:Yeah. It was, was, it was, it was just the evolution of, you know, of Photoshop and Adobe products. And so I grew up with Adobe. I learned I was an early adopter, always, you know, I just sort of like analogy. Yeah.[00:09:49] Nathan:I want to dive into all kinds of things. I want to talk about, more in the financial world and the business of that and everything else. But back and maybe start earlier in your career.[00:10:01] Kimberly:Than elementary school.[00:10:04] Nathan:I guess we didn't go to elementary school a little bit after elementary school. What what did the early days of your career look like[00:10:12] Kimberly:I was a, you know, I'm a first, or I guess I'm a second generation American, so, and I'm Jewish. So of course I was supposed to be a doctor. So my, we used to get, you can be anything you want just as long as you're a surgeon first. So I got the makings of a woman's surgeon and, you know, it was just like, as a book that was a book that I received many times in my middle school years.And then, you know, it was like, that's great, you're so talented. But you know, you really, you know, after you get out of medical school, you can, it was just sort of what you did in my family. And, and my father he was a well-known surgeon and he became an, I don't want to say artist. He became a writer, so he's a well-known writer.And he started writing. So he kind of became an artist before my eyes, you know, so as I was getting out, as I was graduating college, he published his first bestselling. That was just, and I would like sit at the book, you know, when he gave a lecture at an art gallery, because it was called art and physics.His name is Leonard Shlain so I would like sell, watch him, sell the books, you know, like give a lecture and then I would check out and I would get, take people's cash and then give them a book, you know, at the end of the lecture. And he used to tell me, he used to say, honey, you have to be shameless.You have to be willing to just talk in front of four people. It doesn't matter. You just need to do it. If it's just, it was just a big, it did. It made an imprint on me because I was watching him grow out of his own discomfort zone, which I still struggle with of talking to people like instead of through your paintings or, you know, talking to an audience saying being on video, it took me six months to figure out how to be on video, but I'm getting ahead of it.So you asked me like my CR about my career. So I was an English major. I went to an English, major architecture, minor at UC Berkeley. And at the time that I was graduating, painting was considered dead. And I know that that for artists today, they don't quite appreciate that. But after abstract expressionism, there was sort of this mood in the art world that everything had been done and like, forget about figuration was the last thing people wanted to see, you know, and I wanted to paint people.So I just figured, okay, I'm going to just do that on my own, but I'm going to, I love reading. I love writing. So I became an English major and I was valedictorian of, of the UC Berkeley English department. And so my first job, I wanted to combine my love for art and literature. So my first job was.Design. So my, so I, was mentored by a gentleman named Walter Lander, who is the founder of landlord associates. And he was sort of the west coast, Milton Glaser, Milton Glaser from a design point of view, like he was, he just recently passed in the last five or so years, but he like did the, I love New York, you know, like he's this famous, famous graphic designer because the field of graphic design is, is relatively new.It's relatively, it's like a century old, you know, like th the serious field of it. And Walter was a pioneer in it. And he did, you know, my first job was like working cause I, cause I minored in architecture was, helping design the shell oil, gas station, you know,So I was doing like architecture design, and then he asked me to write speeches.And so they had, their company was kind of designed like a brain. So they had like a language division and they had like the design division, like they did the loose soon milk and they were so famous then such leaders. They had 1800 people in offices all over the world and it was like a big deal. And they had an office on a ferry boat.So that was my first job out of college. I was a speech writer for Walter and I was in the, I was in the word department. Like I think I designed, I helped name, a cigarette, you know, like was just a weird, but it was fascinating, you know? And it was meeting fascinating people. The grateful dead would like come over on the boat after it was, it was, it was a wild time at, in San Francisco in the late eighties, early nineties.Totally wild. So, So I was like, so all the designers are starting to learn Photoshop. So there was this thing called Photoshop because they were doing everything by hand, you know? And then I was like, oh, so I got Photoshop 1.0, you know, and then I had th there was no layers. So you had to do everything in alpha channels.And it's interesting just to be a big nerd. Cause you're a designer too, right? I mean that's yeah. Yeah. So if you can try to imagine there was Photoshop without layers, it meant that you had to do everything inside the masking tool that's built in that nobody really uses or knows about now called alpha channels.So I had to create everything using masks, but it was very oddly more similar to what you did with your Exacto knife and ruler, know, I still think one of the biggest, the saddest things about Photoshop. I mean, I think everybody should know it, but it has some feature bloat, but I think it kind of buries the power of alpha channels.And I think that if people knew how to use it, it would like, it's like a little thing to know that would hugely leap them out of the more artificial aspects of doing those filters on things.[00:16:00] Nathan:Right.[00:16:01] Kimberly:Anyway, like I you have to be careful with me because I can go into real. I can crawl real deep into these nerdy things.But anyway,[00:16:08] Nathan:Are there other things from those early days of, of the graphic design art agency, like that kind of world, that you still take with you today[00:16:19] Kimberly:Thousands of Gillian percent. One of them is the four DS that every project is discover, design develop, deploy. And I know I lost that. I also saw that, like, if you could name it, you could charge it.[00:16:32] Nathan:Is there a story behind that? If you could name it, you could charge for it.[00:16:35] Kimberly:You know, you'd see these hundreds of thousands of million dollar contracts going out to these major people. And I used to have to help write the proposals and I would see how they would divide they'd phase out, like a lot of designers. Again, I don't, I hope we're so not too off topic, but a lot of designers will not charge for discovery.You know what I mean? Because they haven't named it. They didn't name it They'd Just be like, oh, let me Research all about your company. And then you're going to pay me to give you some designs, and then I'll give you the designs and then hopefully they're smarter. Anyway, like I said, big, big topic.[00:17:10] Nathan:Yeah. But think there are a lot of people listening who are in the either freelance or agency space and they, provide services to newsletters or creators or they're growing their own on the side. And I think it's a really important point that, if you're if you're structuring your proposals and all your interactions with clients around the deliverable, then you're failing to talk about a substantial portion of the work And probably the part of the work that differentiates you from the other freelancers who are just like, oh, you need a logo. And they dive like right into Photoshop or whatever tool. Whereas if you're good at what you do, you're probably taking a step back and looking at the whole landscape and spending probably more than half of your time in that Research discovery and learning stage rather than the deliverable stage.[00:17:56] Kimberly:It's actually the most important time intensive stage of any project. And so not just design. I mean, I think you saw my Ted talk, the creative process in eight stages. And I think I talked about how as an artist, I don't want to give anybody whiplash, but like you, as an artist, you have, a period of time where it's like a rest in music where you don't, you're not making work.It doesn't look like you're doing anything on the outside, but that's the most important part. And it's when. Gathering, but you're doing it in a subconscious, like in many different ways when I'm, when I'm making a painting, I'm having to listen a lot, you know, you have to listen and look and just inhale before you can exhale.So anyway, that, but I mean, we could, I think, I think we could do a whole hour on Landour. Cause that was just a, such an interesting, you know? And, and I was actually, I was actually there, I dunno. Well, you're, you probably weren't born, but there was a, Coke released a new design and they, they, and Landour was the leader of this new design.And I was like in the boardroom, in my. In pantyhose. Cause that's what we that's what, like you had aware that it was very far, it was like mad men. It was like mad men where like everybody smoked and the women were gorgeous and the men would like have these glass offices on the side of the boat. And they would like go in and light up a cigarette and call London, you know, like they were like, or Japan and, and they had, it was just extreme, chic, crazy environment, very male dominated.And I was like, I'll often the lone woman in a room, you know, but anyway, that's a separate side conversation and they were introducing the new Coke and it was a flop. It was like, it was like, there was a backlash against the new design because it had like big fat. It was like, whereas the old Coke kind of has that Victorian, which they still use now that, that very Sarah fee or Nate almost like your create above your head, but more, you know, whereas.Where the new version they were doing was super kind of chunky. It was like new Coke, you know, anyway. But, it was a wild experience. I wrote an essay about it and I'll, I'll give it to you if you, if[00:20:35] Nathan:Yeah, we'll put it the Shona[00:20:36] Kimberly:Yeah,[00:20:38] Nathan:On time on that.[00:20:39] Kimberly:Yeah, no, the whole, here's the thing. I wanted to be an artist, and a lot of times I believe a lot of, and I believe there's a lot of people who have an artist inside them and a lot of times they will, work in a field that brings them near art decisions to make themselves feel better.That they're not being an actual artist. And I was one of those people.[00:21:08] Nathan:Okay. So how did that play out for you of your you're close to the design and that sort of[00:21:14] Kimberly:I was like, yeah, it was, I couldn't be closer. I was like, I was like in, I was behind the curtain of Oz doing the, with the, with the best people and everything. Again, this is so long ago, but, but I felt like technology at the time, again, Photoshop was just starting. There was no whatever. I was like, you know, I needed, I need a break.I need to like push the table over. So I quit. I moved to Paris to paint for a year. I played piano in bars at night. That was like a whole other wild. We could do a whole show on that, but, you know, then I was like, well, I can't, I'm not going to be able to make a living doing this. Like I was painting, I was sitting at the sore bone and I was like, I had this little gig in this bar, but it was a couple of Franks and I wasn't legal in Paris.And I just had this big because of my literature background I have does such a, you know, I love you. I was so somewhat of afraid.[00:22:11] Nathan:So how old were you when you[00:22:14] Kimberly:I was in my early twenties.[00:22:16] Nathan:Okay. When you, quit and said it's time to do painting.[00:22:20] Kimberly:Yeah. I was like, it wasn't a straight line. And that's another thing. Like most artists don't like some artists grow up and everybody goes, oh, you're so talented.Which by the way, like hate that expression. I must like tell people, like don't ever tell people they're talented. Say you have great raw material, you know, just say, you know, just like great mom material, but like, you have to like do it for eight hours a day in order to like express something. Great. And then, then we'll talk about talent, but in any case, so some people have parents that say, you're honey, you're so talented.I want to send you to art school. I want to spend a couple hundred grand and I'm going to send you to art school. Undergrad, let's say a good, let's say a typical artist, a college education is this amount. And then I want you to get an MFA from Yale or the best school and have that checked off. And then I want you to go get in galleries and be an artist there's 0.01% of artists have that route.They have parents that say, we support this. This is good. This is a good plan. I would say that's like a very rarefied small group. Cause you have to have, well, there's so many things that need to happen in order to have that setup. Most people, most artists, even artists that I know, like one of my good friends Enrique he was a PA getting his PhD in physics read my dad's book, art and physics and decided he wanted to be a painter[00:23:49] Nathan:Okay,[00:23:50] Kimberly:So like, there's a whole bunch of artists that were doctors that were lawyer, you know, that, that, that they, they were catching the train of you know, the I'm a good student, I'm a diligent worker and they, they, you get routed onto a track and then you're on that track. And then suddenly you wake up at at 30 or whatever, and you say, you know, I'm here and I'm super successful, but this isn't necessarily really how I want to be spending my time.You know? I mean, th this is the conversation, right? You know, how do you, how do you decide and what you can want changes in your life? You know, but if you know what you're pull, the tether poll is like, if you know what, your deep inner core desires. are And, you know, and you, you have, you're remotely in touch with that and you, you need to go, you need to go towards that light.You need to go towards that center then everything will radiate out from you afterwards.[00:24:58] Nathan:Was there a catalyst that pushed you, you know, you were thinking about it, you're feeling this, but what was the thing that made you go like, all right, I'm[00:25:06] Kimberly:Well, okay. Like I said, we don't have enough time to get into all of this, but there were, I made three huge dramatic, you know what? I don't know. Maybe it's a Monty Python movie, I don't know. But like when you push the table over and you throw all the plates and you break everything, like you just come, it's not a reboot, it's way more violent than that.Just kind of like you take the tablecloth out and you just say I'm out of here. You know, I think I did that three times before I got closer to. You know what it is. And one of them was moving to LA after moving to Paris, I moved to New York and then, then I moved to LA and I was like, okay, this time is going to be it I'm being artist.Like, and you know, it's a couple of years later, it's after Paris. Like, you know, cause you have to get, you have to, I had to make money. You know, I had to make a, I had to have a job. And so I had to kind of like do, do design work and stuff like that. So when I moved to LA, my first, I went to a Mac conference, like it was like 60 booths.It was so small, like Mac was seen a teeny little thing and, and Microsoft was the big thing windows and,[00:26:18] Nathan:Yeah.[00:26:19] Kimberly:And I made a business cards and I said, it said artist. And then when I, I walked, went to this conference and I was practically like often the only woman, you know, and I would say, yeah, I'm an artist.And I know. And so the first job I got was making the first CD rom for apple computer that they said distributed to every single apple. So they distributed over 2 million copies worldwide, and my name was on it. And that kind of, that was a huge breakthrough because suddenly I was being offered insane jobs.And next thing you know, I was anyway, like, I don't want to dwell on this because we haven't talked about newsletters yet.[00:27:01] Nathan:That is okay. that is okay. So you just made a leap from, I went to this conference to,[00:27:08] Kimberly:Yeah, by the way speaking, we started with going to a conference.Yeah.[00:27:12] Nathan:A big deal. We are we talking about that as well, but this leap from going to the conference to your work, being on the CD,[00:27:19] Kimberly:Well, so they were, it was like, again, I was on the bleeding edge. I could not explain to my father Who would come down and visit me. In the warehouse. I, it was, it was an artist and a coder who, but they had both met in art school and they brought me on to be the creative director.And it was like, it was almost no money at first. And then it became like a bigger thing and apple, the more that apple saw it, the more they were like, wow, this is really good. so then the next conference I went to was in San Francisco was Macworld and my art was everywhere, everywhere, and I got job offers from Imagineering. They wanted me to design why the Disney, they wanted to be the head. Of Warner music was doing a new interactive division and digital don't digital.I can't remember the names, but it was very, it was a very heady time. It was very, it was very fun. I felt like, wow, I found this place that has it's the intersection of art design, narrative and technology. And it was exactly where I want it to be. And that was just, that was sort of, and I set up an easel in my office, I had a lot of people working for me and it was just, it got very, it got very fancy, you know, and I, and I took a lot of, I took a lot of like what I knew at Landour to attach in this before email this before the internet.[00:28:45] Nathan:You're talking early nineties at this point,[00:28:48] Kimberly:Yeah. Like you no, like a mid yeah. Mid nineties, you know, 96, maybe. So, yeah. So I took a lot of my, knowledge that I gleaned from working at land or like the discover design develop, deploy to whip these engineers and designers into shape, you know? And anyway, I was still stalking what I really wanted to do, you know?[00:29:10] Nathan:Okay. So tell me more about the difference between what you wanted to do and what you were doing, because you just described your art being on everything.[00:29:17] Kimberly:No, no, no, actually, honestly, honestly like I would listen to like Liz fairs, exile in Guyville, as I drove downtown by the toy factory in downtown Los Angeles back and forth, like every day, like at these, I was a big album listener.And when I was designing, I would listen to full albums and I was just like, wow, this is it. I am so excited and energized and everything. then I started studying painting again. So I started so like I had taken a hiatus. And then I got into the, Otis, which is the art school here, You know, when you get professional, when you become a professional in anything, even being an artist, there's a, single-minded rigor focus and clarity. one brings their whole self to what they're doing, you know? And if you know that if If you've been successful in anything else or anything like that, you can, if you bring that to your art, there's literally nothing that can stop.You. You become a wire cutter. It's like, you're going to munch through like, I, you know, really understanding, painting in the deepest way possible. Like I was thinking if I can understand alpha channels, I can figure out how to tone a canvas. You know, just like I just, because painting is a technology, honestly.I took everything in my being to it. And that was like a third moment. Like that was like another moment I skipped some moments, but there was like where I was knocking at the door, knocking at the door. And then I knew that in my art would become the, that I had when I started painting in full force.Like not just having it in my office, but saying this is what I'm going to do. And I'm going to do it as so ferociously, like stand back, everybody, nothing is going to get in my way.[00:31:13] Nathan:So you were painting, I mean, you had is this like painting a few hours a week, a few hours a day, and then you dove into doing that, just like.[00:31:22] Kimberly:This is like 40 hours. I mean, I basically gave myself an assignment and my assignment was I was going to paint a hundred new. Because that's the hardest thing to do as a body. Cause you have to deal with the translucency of skin. And I could literally talk about painting all day, but you have to deal with light form and shadow and thinking in three dimensions and it creates it's.I don't want to knock marketing and technology and the stuff that you do, but painting is that most people do, but painting is a true, like you have to really, it's a very intellectual as well as mindful and spiritual, but it's a very, it's a very deep, deep, deep way to approach the world. And when you become a painter or you actually like listen to the little voice inside you that says that they want to learn this.It's a skill, it's a skill. And when you do that, your brain expands and your world expands and you see things differently. So it's a very transformative thing and it takes years. It takes years and years. So my assignment was I'm going to paint a hundred nudes and, and if I have like 10 good ones, I can have a show.[00:32:41] Nathan:So I want to tie that to maybe the experience that other creators listening would have, or anyone who's on the fence about getting started. Right. It might not be painting that they're trying to do, but they've had these fits and starts of like, I'm going to, learn to code, start a podcast, start a newsletter, any of these things, you know, learning to play an instrument, whatever it is.And then like start and it goes, maybe it goes well for a week or a month, or like what, what advice would you[00:33:11] Kimberly:Isn't there, isn't there like a guru isn't there like a guru in the subject that calls it, the. Who's that guy. Do you know what I'm talking about? Yeah. Somebody told me that, cause I was saying this to somebody and they were like, oh yeah, that's somebody's Seth, Godin's the dip. But yes. You know, when I was younger and all through all through my, you know, middle school and high school and college, I played piano quite seriously.I was a classical pianist and whenever I would learn a difficult piece, I would play it over and over and over again. And I would have to, like, I would start to suck. I would get better, but then I would start to suck and I'd have to walk away and then come back at it the next day before I would be able to play it perfectly.Like, I mean, you know,[00:34:01] Nathan:Yeah.[00:34:04] Kimberly:Learning an instrument actually teaches you this better than anything, because if you make a painting at first and it sucks, you can be easily thwarted, like a, you know, a drawing or whatever. But, but in order to like worry the bone of like how to get that legato, right. And that Greek piano concerto or something like you got to just sort of do it again and again, and again and again, you know, like it's, the fundamental way to learn is you, you imitate, assimilate, and then you can improvise.So you have to like, you play these pieces. And so with anything, you're going to be thwarted in the beginning many times and you can't give up, you have to say, okay, well, I don't care if it even sucks. I don't care if I'm going to fail. If I'm gonna fail, I'm gonna fail big. Like I'm[00:34:52] Nathan:Right[00:34:52] Kimberly:Go all out.Let's just go on.[00:34:54] Nathan:But that specific assignment that you gave yourself of painting 100 nudes, do you think that an assignment like that is a good way to go as a creator of saying this is the commitment that I'm going to make, I'm going to get to a hundred podcast episodes or I'm going to, I don't know, write a hundred blog posts, and then I can decide if this is something I actually want to pursue.[00:35:13] Kimberly:Absolutely. I think that when you make a commitment like that, to devote your energy into building a body of work of any kind in any media, you, your life will change everything. You are going to gain skills that involve every facet of that media. So like, if you're a podcaster and let's say you record in iMovie you're going to learn iMovie or whatever they, whatever they edit podcasts.In And, and I think if, you know, if Leonardo DaVinci were alive today, trusts me. He would know Photoshop He would know he would be all over this stuff, you know, he would love, he would love it in this nether world space, because there's, I'm, I'm going off topic a little bit because there's a little bit of a prejudice in the art world where people were thinking they were resisting the newer technological versions of artwork.But back to process, what you were saying is that if you do something in a committed way and you basically measure it and say, I'm going to do it until I get to this point, I think a hundred might be excessive, but you're going to get the hang of it.[00:36:28] Nathan:Yeah[00:36:28] Kimberly:I mean, I haven't mixed feelings though, about blogging cause I started a blog again, when I was, really getting into.Consuming. I mean, consuming isn't the right word. When I was throwing my entire body into the art world, one of the things that I did to expand my own knowledge was to write about other artists. And I think that's also something that's super unspoken, especially in the art world, because a lot of artists are just saying Me me me I want attention.I want to get people to focus on my show and my work, and I want a gallery and I want this and that. And I think one of the most important, aspects of breaking through to any next level of anything is generosity. Generosity of your attention to other people who are doing the same thing. And that for me, that general, I mean, I didn't think of this.This is red, this is a in retrospect, but at the time when I look back on it, I was airlifting artists that nobody had heard of and writing about them along with other big art, you know? And so I had a successful weekly column where I was keeping a blog again, this was before social media and that's how, and then the Huffington post came along and then I started publishing it, the, having a post.And that's how I said, I was asked by Arianna Huffington to be the, to found an art section. And so I was like, I was perfectly positioned because I was, I was a big nerd. I had had these other experiences. I was a full-on painter. I was having shows galleries the whole thing. And then she was building this incredible Site to celebrate bloggers. And I was one of the bloggers So I had to build an audience from zero to 10 million people within two years. I didn't have to that's what happened.[00:38:26] Nathan:Right.I have so many things that I want to ask about in this, one thing that I want to highlight that you talked about is as you're doing the painting, there's the side of it, of, Research where you're researching other painters, learning from them and all that. Most people keep that Research to themselves, right?That is not a public thing that happens. And I think a lot of the most successful creators that I see are the ones who do that recent. And, and share their notes and share that and work in public and do the interviews and all of that that you were doing. because it does a couple things. One people follow you, not only for your own work, but then also for your notes on other people.And then too, it's incredible for meeting people. Like when you do a profile, either if they're a, say an upcoming artist or someone who's established either way, they're going to be like, when you, you know, when you send them an email, they'll like respond and be interested and engaged. And, you know, I mean, that's a reason that I do this podcast is so that I can meet and hang out with people that I want to more aboutIt's amazing for network.[00:39:30] Kimberly:Yes. I think you're exactly spot on. This is no different than what I did with artists, this, except for I wasn't involving video, I was writing about it and interviewing them. You're right. You're absolutely right. I also think that you can get too carried away with that though. Like you have to be careful, you have to make sure that you're, you know, I can become easily like Clydesdale the horse.I'm like, well, that's another month and I have to do another,[00:39:57] Nathan:It becomes more important than the art, which was the[00:40:00] Kimberly:Well, yeah,[00:40:01] Nathan:It feels more time than[00:40:02] Kimberly:Yeah, yeah. Like, so eventually I had to leave, because it was just sort of eclipsing. It became so much bigger than everything else I was doing that I had to like go, okay, this isn't, you know, I've got a show coming up. I can't devote all this time and energy. And then of course, social media kind of made it all really different.[00:40:24] Nathan:Like in what way?[00:40:25] Kimberly:Well, because not only we could, you know, writing a really thoughtful piece about an artist and looking at their work and, you know, relating it with art history. And I also found that if I could relate it to like a contemporary event, like there was this one painter who painted battle scenes and we were just going to war with Iraq, I think, anyway, we were going to war somewhere.You know, it was a horrible time, but like, I would talk about going, you know, this contemporary news event. And I would link it with the artist who was painting these battle scenes. And then seeing that it went, go.[00:41:04] Nathan:Right.[00:41:04] Kimberly:Was another, that was another big learning lesson is like, if you put a number in a headline, like 10 things, you, you should tell, you know, 10 rules for your kids and screens, you know, then people would read that more.So I could see the analytics of what people clicked on. You know, that was like a interesting learning experience. But when social media happened, then suddenly you also had to tweet it. You had to post it on Facebook and then you had to tweet about it and then it just got to be social media. here's my take, if I could just say one thing, because I want to get it out there.I think social media is great for first impressions so that when people see you for the first time they're going to go that person's like a real artist or they're a real whatever, and they're legit. And they don't just have like three things that they've said about the subject. They've actually like, I trust that they've done some deep things.Like me painting a hundred nudes, you know, like this person knows how to paint.So I think social media, it's just so easy to get carried away. I hope one day it goes away. Is that terrible to say? I think emails should be everything. It should just go away.[00:42:14] Nathan:I don't think it's terrible to say at all. You have something in your Ted talk. you talked about like the compulsion to paint being taken away by your smartphone and these distractions, And I'd love for you to talk about that because I think there's so many things of like, if I'm on Twitter or checking my email, or even interacting with the ConvertKit team 2,700 times a day, you know, it makes it so much harder as a creator.And so I like, I just want to hear more of your experience there.[00:42:45] Kimberly:Well, I mean, in order to even get into my zone mentally to paint, I have to like have at least 90 minutes where I haven't spoken with anybody. Like I just need to kind of like clear it. Like I need to, I mean, I can be in it and I've got all these, you know, because people everybody's different. Some people like beginnings, some people like middles, other people's like ends.So you have to get in touch with which person you are, you know? So I, I love middles and beginning. I actually like all of them, but like, I'm better at certain things. So whenever I go into the studio, I have to start in paintings that are in the middle, that many going on at once. so you have to get in touch with like what time of day you're best at.And I always begin things at the end of the day when I'm already like nice and a well-oiled machine, well-oiled creating Machine.I never begin things in the morning. I always begin. at the end of the day, I never begin paintings in the morning. I was beginning, you know, I mean, I, I'm not, I know I'm not answering your question.Your question is, compartmentalizing your time to protect it away from social media. I teach a master class and I teach a Masterclass with artists who are building their first body of work, or they, they want to build a body of work in the masterclass.I make them take an oath an Instagram oath Instagram is it's so draining psychologically, emotionally, mentally, and the effort that you put into it that you really have to like commit and, and, and artists feel pressure to post their progress and post once a day and stuff like that.And the truth is, that algorithm, the algorithm is so fraught right now because you really only see the last 20 people that you liked more often than not. And you're not, it it's just, it's not healthy. It's not healthy for a visual artist Because you'll be on it. You check it like a diabetic checking their insulin level.It's just like, oh, did it get enough? Likes all that. It's like, Ugh. So I use, later to post once a week because I don't really want to deal with it. So I'll do like four months at a time. But if like I have a museum show opening up on Saturday, so I have to make a post this week. And so that that's like in my brain, oh God, I got to make a post this week.And when my book was coming out, like that's a whole other topic about promote, you know, how to tell people and that a book is coming out. yeah. So I just kind of look at it like, you know, kind of like a creative sinkhole,[00:45:15] Nathan:Yeah. And so it[00:45:15] Kimberly:So it[00:45:15] Nathan:Makes sense to avoid it. I think we hear that advice from a lot of talented creators and it's easy to be like, yeah. Yeah. But I can, I'm the person who can sit down and write with a moment's notice, you know? And then you you get totally stuck on writer's block or whatever thing, because you're like, you actually didn't create that space.And, like you talked about in the Ted talk of that time to like daydream and to actually be there, present with yourself and your thoughts.[00:45:42] Kimberly:Yeah, it's true. I mean, there's this thing in neuroscience called empathetic mirroring. Do you know about[00:45:48] Nathan:I don't know.[00:45:49] Kimberly:It's this, it's like when you see somebody, for example, write on a chalkboard, the neurons in your brain, I'm not going to say this. Right? So if a neuroscientist says I'm like slightly wrong, but like, it, it, it has this effect where you feel like you're doing it, you know, like, and it's, that's why people love to watch people write things.That's why a chalkboard is an excellent device for, I actually have a chalkboard in my office because I started to. Take videos of me make with my talking points of me writing it on a chalkboard, because even though it's considered like, you know, yesteryear technology, it actually helps people receive the information better to see it written[00:46:34] Nathan:Rather than being next[00:46:36] Kimberly:Rather than just show a PowerPoint slide.Yeah. And so this, the act of seeing it rhythm, but so if, if you think about the power of empathetic mirroring, that's going on in your brain, when you look at something happening, think about how much it can pollute your brain. If you're watching a stream of all these things happening in your Instagram feed or your Facebook feed, it's like dangerous.Like you have to be protective of what is going inside your mind. It's that they say like garbage in, garbage out, you know,[00:47:04] Nathan:I want to hear about you getting into the world of, of like teaching classes and that side of it, and then you have a book as well. There's a lot.[00:47:12] Kimberly:Oh yes. So I have this book,[00:47:15] Nathan:There[00:47:15] Kimberly:So, you know, around a decade into, you know, being a serious painter, I started to feel bad from the fumes because painting isn't really taught the way other things are taught. Painting is sort of like, there's, there's been this somewhat mystical, you know, here's a bunch of art supplies go to the art store and then let's see what you come up with.And then the, the, the classes tend to be more about critiques, about what you've done versus about,[00:47:45] Nathan:How do something.[00:47:46] Kimberly:About the, the true, true granular house, you know, the, how, like the basics, like things that you should know. And, so I started to get sick and I happened to be the arts editor at the time of the Huffington post.And I reached out to, and blogging was a very interesting, it was around 2004 or five, I think. Maybe, maybe it was a little bit later, but it was an interesting time because other people were thinking what I was thinking and I could see it in search for it. Whereas I couldn't, I couldn't have done that a decade earlier.And so I would reach out to leaders in the field, scientists, whatnot, to write about this topic of safety, you know, like that. And, but then when I read and I had, by the way, been consuming, Disneyland books, everything about painting, and I just saw this huge gaping hole of knowledge of how. Communicated. So I started writing this book all about painting and the book that I ended up publishing with Chronicle books is just one small piece of it because it was kind of too big.It was like James Joyce's Ulysses, you know, it was like a tone. It was like a Magnum Opus. and it's one of the key things that people don't realize is that you don't need to use solvent's P many people believe that you need to have like an open can of turpentine or some kind of solvent to dip your brush and defend the oil paint.So it's like super basic and most people when they go to the art store, and this is just my short, my short, skinny on the book. As most people, when they go to the art store, it would be like only buying canned or prepackaged. They don't know what's in it, you know, they don't know like that you don't need all those things.Like, but if you were like learning how to cook, you would know the difference between a garlic and a shallot and when to use canola oil or olive oil extra-virgin, you know, so I wanted to create, to start a book called the Y that was like Strunk and White's elements of style, but for oil paintings. So that's like the famous book that most writers use and just sort of shows you.And it's funny, actually, it's like a great book. So I wrote that book and that's called the new oil painting and it's published by Chronicle and it came out in June and it's like staying at the top, like five books of oil painting, which is great, you know? So I'm very excited about that. But in any way, in that journey of writing the book, the book, the book deal I got was two years ago.It was like a while ago. And so Susan. Did that I thought, you know, I would be a fool to not have a class that went with the book. So to the summer of 2019, I had, I had like four solo exhibitions in a row and I thought, okay, I'm going to devote six months and I'm going to record videos and I'm going to do that.You know? So I created this class that I wish that I had, and it was way bigger than the book. It was like everything I've ever thought about oil painting and that's called oil painting, fluency and flow. And, so yeah, so I launched a class, so the classes are out there[00:50:52] Nathan:Are the classes something that, you know, you're teaching in an online course? Are you there in person or through a partnership with.[00:50:58] Kimberly:So once I, once I learned about. That you can oil paint anywhere like you, Nathan tomorrow could decide, you know what? I w I've got an artist in me. I want to, I want to learn how to paint and you could set it up next year, you know, like in a little side table next to your computer, and there would be no fumes, no nothing.And it's much better for the environment it's not made out of plastic. It's like, you know, you could do it. So I wanted to get the word out. And, so my first class is, and so I was started teaching at major institutions. So the Anderson ranch in Colorado and the Otis where I actually took lessons, I taught there.And then, I just thought to myself, you know, this is highly inefficient because I have to like schlep over there and go there for, you know, hours at a time. And I could reach so many more people if I recorded. Instruction. And so I made these recordings, that's a hybrid of recordings and live sessions and critiques.And I have, you know, I have about 78 students right now. They're from all over the world and it's like the boast enriching wonderful, fabulous thing I've ever done[00:52:08] Nathan:Yeah.[00:52:09] Kimberly:To being an artist, you know,[00:52:11] Nathan:And so how does that interact with the newsletter that you have?[00:52:14] Kimberly:Well, I mean, so all of my experience, just as an artist has taught me that you, your value that you bring to any situation is the people that you can tell about what you do. It's like a tree falls in the forest. Nobody knows you're having a show. You know, you can't just rely on your art dealer.And the The dynamic has changed where. People don't have one, rarely do people have one gallery that represents them. And then they've got a bunch of satellite galleries. So you kind of have to be a little bit more entrepreneurial as an artist. And so you need to gather an email list. And so I stopped blogging and instead I have a newsletter because I want, you know, and I I have a narrative of stories that I tell about creativity about, about like I'll crawl deeply inside the making of a single painting of mine, or maybe another one.And I, and each email I send out, I spend a lot of time on, and it's like a work of art by itself because it's, again, it may be a different thing. a newsletter may be slightly different than a blog, but it's still words and image and it's just how. It's like another work of art, it's another work of art.And I love, using ConvertKit. I mean, I really, really do I tell people about it. I tell people about it all the time, because I think it's, it's the first software I've encountered that, allows you to very easily create a sequence. And, you know, you can I tell people, I say like, if you want to think about it, you could unspool Tolstoy's war and peace.If you wanted, like you could, every week you could give like a little section and you can start at the beginning and it takes the pressure off needing to constantly have every email be a first impression. So you can really get, let people to get, to know you in a much deeper, more personal way, because you create a sequence of letters to them that[00:54:23] Nathan:Right[00:54:24] Kimberly:Over time.[00:54:24] Nathan:Well, I think that's a really important point about starting at the beginning, because when you're sending these one-off emails to your newsletter, you don't know where people are joining. Some people for years and other people that is the very first thing. And so every time I find myself adding these caveats are like, Hey, if you're new here, you know, any of those things and with a, an email sequence, you know, the automated series, it starts at the beginning every time and it works people through it.And so I've had that. I've had so much fun creating those because you can chip away at them. Like I have one that I'm kind of writing now on, I guess it's on personal finance, you know? And it's just things that I wish that I had known as like, Moderately successful creator. Like, Hey, you're now earning a full-time living, what what's next?And so I can just write about that when I feel like it and add to this, that's now like 10 or 12 emails long.[00:55:20] Kimberly:And what's your frequent.[00:55:22] Nathan:That one I said to every week, but if I don't write for it, everyone just kind of pulls up at the end and weights, you know, for the next email. So it's 10 emails And then I add to it. And so like last week I didn't add a new one. And so now there's like a hundred people that are all the way at the end and they didn't get an email last week,[00:55:41] Kimberly:Yeah, no, I have that situation. I have a two year sequence[00:55:45] Nathan:Oh, wow.[00:55:45] Kimberly:I mean, I know like I sound, I probably seem super extroverted and voluble and everything like that, but like, I, I, it's very difficult for me to sell. It's very, it's very not. It's not cool for an artist to be. So like, I mean, it's just hard.It's also just hard for me. It's my personality. Like I even posting on Instagram is like a stressful thing for me. It's like, did I get everything that, you know, like I just, it's just not, I'm not one of those people that just casually throw stuff out there. I just, I'm very thoughtful and I want it, you know, it to be meaningful.And, but anyway, I was having trouble announcing that a workshop was over. Like serious trouble. Like I would put it off and I'd say, I can't do it. I can't press the send button. Like I just, even though you have the schedule feature on the broadcast, I was like, I can't do it. I can't do it. And you know, I, I can't remember the name of the marketing guru who was, have the five day sequence or, you know, basically a launch sequence is a series of emails where you first email is all about it.The second email might address one's reservations about it. The third Emile email might be testimonials. And then the fourth and fifth email are like last chance to get it. Like that to me is like, I would rather have needle eyes surgery than do that, you know, so I built it in, so I basically have the sequence where every quarter there's a launch sequence.Is that crazy[00:57:13] Nathan:No, it's fantastic[00:57:14] Kimberly:Because then, so, so that way, like I can just set it and forget it, like back to the Crock-Pot thinking like, you know, like, you know, just set it and forget it. You're going to sign up. You're going to get an announcement for a walk shop, a workshop a couple months after you've gotten to know me.[00:57:30] Nathan:Do you think that, well actually I guess really quick, the thing that I love about that is you can be completely immersed in your painting, right? And there you are selling a workshop and you're like, you don't, you have to think about it or know about it. Cause you did that work once and now you've finished a whole day of, of painting.Start something new at the end of the day. Cause that's the way that you roll. And then also you can say like finish up and check those sales and check that engagement. See, oh, people.[00:57:58] Kimberly:Yyeah, yeah. I mean, it's, it's just, it's I think people before they're going to buy anything, need to feel. Most people need to feel, you know, a level of comfort about what that person is about. so, you know, I haven't touched you tube. I haven't really, I honestly, I haven't made, I haven't made a huge effort because I've had the book coming out and I F I ha I had a big exhibition in June because, I designed a series of, excuse me.I designed, I painted a series of abstract paintings, for the cover of the book, because I wanted the cover, the book to be stellar and represent like a specified stroke, like hanging in air, like, to just convey the idea of painting and not be like a landscape, because for some crazy reason, if you, if you look up oil, painting, all the books, About oil painting are so poorly designed.It's like, it's strange because you would think people who are artists would care about design, but it's like pink pallet, Tino, bold 14 point font over like a green sunset. it's[00:59:07] Nathan:Yeah, well, design and painting are not necessarily the same thing you happen to come from a world where you have a lot of this. Even those two worlds have intertwined for you a lot over your career. So it makes sense to[00:59:18] Kimberly:Yes, but, but when, when, but if you get, but the painting books, like if you see a PA a painting book that has like a landscape on it, what if you don't like the landscape or they all have a landscape, or it has like the, the, you know, a face that's loosely drawn with, you know, painted with turbine, you know, Alla prima anyway.I've had so many exhibitions and like, I have a, I have a show coming up on Saturday and I've got to tell people about it. So like, I have to be, I'm already out there as an artist. So I have two different sequences and newsletters. I've got like a workshops for people who express interest in a workshop within the main newsletter.Like if, if, like, I'll say like I have this one great newsletter where the subject line is, who is this gorgeous woman? And then I show a picture cause they used to paint these beautiful renditions of the faces of the Egyptian mummies inside the sarcophagus, like beyond gorgeous. Like if you looked it up, you'd say, oh my God, this most beautiful painting I've ever seen.And it looks a lot like Francesco Clemente, which is an artist that like paint uses the same aspect ratio. It's like, you sort of go, oh, that's where that guy got that idea, you know? But. I'll talk about the pigments and that they used to, like, they used to burn mummies and then take the ashes and make a pigment called mummy brown.I know that sounds really kind of gross, but like, but, but they that's what they did. And I I'll say like, if this interests you, you might be interested in like a workshop. then if they say yes, then they'll go into my workshop sequence and they'll get notified when I open them.[01:01:00] Nathan:Are there other things that you do with email and with your newsletter[01:01:04] Kimberly:Yeah. Like I, like, I really want, I really want people to easily update their preferences. So I created a jot form like that simple select, you know, check box check if you're no longer interested in, workshops. No problem. Let me know. And I don't get enough work. Ominous, but hopefully, hopefully you'll put that feature in soon.[01:01:30] Nathan:We're actually working on building that feature now. So,[01:01:33] Kimberly:Are you kidding? When does it come out[01:01:34] Nathan:It's one of those asking where the paintings are done. It'll be done when it's done.[01:01:40] Kimberly:The other thing that I do is I really think gifts are important. And I think the marketer, the marketing community is really cheesy about it. Like they always do like outtakes from friends for reaction shots.And it's just so horrible, but I mean, it's just corny and you know who I'm talking about, but, you know, anyway, a gift is a beautiful thing because it's a movie that plays automatically and it doesn't have sound and. it can be so beautiful and subtle, you know, so every time I make a news that I usually have like an, it's like a work of art to me, you know?And sometimes if I want to emphasize a word, I'll paint a picture of that word and I'll integrate it in it. So like I really spend, I really love making them special. Yeah. I have one about the creative process and about not, not the Ted talk that you saw, but like I have one that's on the lead up to talking about the masterclass.Where it's called the curse of perfection. And I show, I talk about how, when I was a kid, my mother used to always like, she would sometimes wear like super smudge makeup and it was psych, it was called the smoky eye. I mean, they still do it now, but now the beauty people make it super specific, but then it was not that it was a little bit more like, woo.And I found a beautiful GIF of like a smokey eye, like slowly opening and closing. And I then go off on this whole subject about how, you know, it's as a painter, you have to let go of that, of the chains of perfection. You have to let it go in order to.[01:03:22] Nathan:Yeah. Well, I love that you're taking a medium that you know, of email or gifts or any of these things that a lot of people use in one way. And you're bringing those styles in that like class and sophistication and really just the level of effort. I think a lot of people are like hearing. Oh, I'm supposed to have, images or gifts.I'm supposed to be funny. And so they just look for something and slap it in there. And there's a level of effort that's not happening there, but because you're doing these automated sequences and you know that if you put this effort into it, it will last and work for you for years, then it's worth it.You can do a custom painted, you know, word or something like that to illustrate a point.[01:04:04] Kimberly:I mean, I have the luxury of having hundreds of paintings, and pieces of paintings, and video of—there's nothing sexier and more beautiful than watching somebody mix paint. There's literally nothing more gorgeous than that—So, I'm lucky.And I understand that other creators have to find other things, but there's a way to do things that have like a metaphorical—I here's what I would say. I would recommend that people seek to enhance their ability to think in metaphor when they write.So if they're gonna talk about a subject, and they're talking about a roadblock, instead of drawing a boulder on a road, find some other image or GIF. I use a lot of GIFs from ballet. You can find beautiful GIFs just by searching “Swan Lake” GIF, and it implies a physical movement.It goes back into that empathetic mirroring, where you feel that your own body is doing these movements that are surrounding this idea. It's not directly about what you're talking about, but it's like a little bit to the left, or it's just kind of a metaphorical version of it. It creates the space in between what you're literally saying, and what you're actually seeing that ignites the imagination and the view.[01:05:35] Nathan:Yeah. I love that. Just putting that extra bit of effort into defining the thing that's adjacent, rather than blatantly the first thing that came to mind. I think that makes a huge difference.[01:05:46] Kimberly:Yeah,[01:05:46] Nathan:We need to do a part two, because I have like 25 more questions to ask you, and we're out of time.[01:05:52] Kimberly:I'm in. I'm in.[01:05:54] Nathan:This has been amazing. Where should people go to subscribe to the newsletter?[01:05:58] Kimberly:They should go to KimberlyBrooks.com. The newsletter's right there in the footer and on the top. I really love communicating this way, and it's been an honor to be on this podcast, because I really love the product you've created. I really couldn't do it without you—without ConvertKit.So, I just, I'm such a fan, and I'm an evangelist, so kudos to you.[01:06:19] Nathan:Wow, thank you.Well, we're exci

Dave Pell has been writing online for almost as long as the internet has existed. His popular newsletter, NextDraft, has over 140,000 subscribers. NextDraft covers the day's ten most fascinating news stories, delivered with a fast and pithy wit.Dave has been a syndicated writer on NPR, Gizmodo, Forbes, and Huffington Post. He earned his bachelor's degree in English from U.C. Berkeley, and his master's in education from Harvard.Besides being a prolific writer, Dave is also the Managing Partner at Arba, LLC. For more than a decade, Arba has been angel investing in companies like Open Table, GrubHub, Marin Software, Hotel Tonight, Joyus, and Liftopia.In this episode, you'll learn: How Dave merged his two writing passions into a successful product The key to building a strong relationship with your audience How Dave dramatically increased signups to NextDraft Links & Resources Flicker Unsplash Fareed Zakaria Jim Rome The Skimm Morning Brew The Hustle Spark Loop Sam Spratt Dave Pell's Links Dave Pell on Twitter NextDraft newsletter Dave's new book: Please Scream Inside Your Heart NextDraft app PleaseScream.com Episode Transcript[00:00:00] Dave:If you have something to say in one way or another, the internet is a great place for people to figure out a way to receive it. So, that's pretty powerful and still excites me. I still press publish with the same enthusiasm now than I did when the internet first launched.[00:00:23] Nathan:In this episode I talk to Dave Pell, who has been writing for basically as long as the internet has been around. He's been an investor since the early days. He's been writing since the.com bust, and even before then. He writes his popular newsletter with 140,000 subscribers called Next Draft.We have this really fun conversation about writing. His writing process. How he grew the newsletter. Bunch of other things that he cares about. Even a few things that I was interested in, like he doesn't have his face in photos on the internet very much. He has his avatar instead. So, just getting into why that is.He also has a book coming out soon. It's called Scream Inside Your Heart, which is a fun reference to some memes from 2020. So, enjoy the episode. There's a lot in there.Dave. Welcome to the show.[00:01:12] Dave:Thanks a lot for having me on.[00:01:14] Nathan:Okay. So you've been doing this for a long time. You've been writing on the internet since the .com era. So, I'm curious maybe just to kick things off, what have you seen—I realize this is a giant question.What have you seen change? What are some of those trends that you've seen, that you either really miss from the early days, or some of those things that you've held onto from the early days of the internet, that you're really still enjoying?[00:01:46] Dave:Yeah, that is a pretty huge question, but I'll give it a shot. The thing I miss from the early days of the internet is that our democracy was not being destroyed by the internet in the early days of the internet. So, everything we thought we were building, basically it turned out to be the opposite of what actually happened.The part about the internet that I still feel is there, although a little bit less so because of the big companies have sort of taken over all the platforms and stuff, is just the idea that someone can have a passion or a creative output that they want to share with the world, and they can mold internet tools to fit their skills, and then use the internet to broadcast that out, and still become sort of pretty popular withour the “OK” of some gatekeeper at a publication, or at a television studio, or whatever.The indie spirit of the internet still lives on. It ebbs and flows, and has a lot of different iterations. But that was the thing that excited me the most when I first played with the internet. And that's the thing that continues to excite me the most now.[00:02:57] Nathan:I always think of the newsletter, and your newsletter in particular, is that indie spirit. Is that what you see most commonly in newsletters? Or are you seeing it in other places as well?[00:03:10] Dave:I see it in podcasts. I see it in newsletters. I see it in people sharing their art, sharing their photography on Flicker, and up through the more modern tools. I go to a site called Unsplash all the time to look at images, and it's just basically regular people sharing their images.Some of them are professional photographers, some aren't, and they're getting their work out there, and then some of them probably get jobs out of it and stuff like that. So, just the idea that you can have some kind of creative output and have a place to share it. And try to get an audience for that is really inspiring.It's a lot harder than it used to be because there's a few billion more people trying to get attention also, and because there are more gatekeepers now. So, you have to, hope that your app meets Apple's guidelines, or that different products you might want to share on the internet have to meet certain classifications now, whereas they might not have in the very early days of the internet. But in general, if you have something to say in one way or another, the internet is a great place for people to figure out a way to receive it.So, that's pretty powerful, and, still excites me. I still press published with the same enthusiasm now that I did when the internet first launched.[00:04:32] Nathan:Yeah. So let's talk about the main project that you have right now, which is Next Draft. Give listeners the 30-second pitch on Next Draft, of what it is.[00:04:46] Dave:Sure. Basically I call myself the managing editor of the internet. What I basically do is a personality-driven news newsletter where I cover the day's most fascinating news. I cover 10 stories. A lot of times in each section there's more than one link. I give my take on the day's news, each individual story, and then I link off to the source for the full story.When I first launched it, I called it Dinner Party Prep. I provided enough information for you to sort of get the gist of the story. And if there's topics you want to dig deeper, you just click and, you know, go get the story yourself. So that's sort of the overview of it.[00:05:27] Nathan:Nice. And you said that you're obsessed with the news maybe in a somewhat, even unhealthy way. why, where did that come from?[00:05:36] Dave:Yeah. Well, nothing, nothing about my relationship with the internet is only somewhat unhealthy. it's all extremely unhealthy, but, both my parents are Holocaust survivors and, when I was growing up, news was just a very big part of our daily lives, especially when my three older sisters moved out and it was just the three of us, that was sort of our mode of communication.We talked about the news. We watched the news together. Fareed Zakaria is basically the sun my parents always wanted. but so I got really into the news and being able to connect the news to, our everyday lives, which of course my parents had experienced as children and teens and Europe during world war II.And also reading between the lines about why certain politicians might be saying something, why stories are getting published a certain way. So I just got really into that and I've always been into a and college, you know, I, I majored in English, but if we had minors at Berkeley, I would have minored in journalism.I took a bunch of journalism courses. I've always been really into the media, but not so much as quite an insider where I go to work for a newspaper, but more observing, the news and providing sort of a lit review of what's happening and what has momentum in the news. So I sorta got addicted to it and, Also as a writer.My favorite thing to do is counter punch. I like to have somebody give me a topic and then I like to be able to quickly share my take, or make a joke or create a funny headline about that content. So I sorta took those two passions of the way I like to write. I like to write on deadline. I like to write fast and I like to counter punch and the content that I like, which is news, and I sort of merged those two things and created a product, and a pretty cool suite of internet tools to support that.[00:07:35] Nathan:Yeah. So that makes sense that you've identified the constraints that match your style and made something exactly that fits it. the deadline, like having, he, you know, coming out with something on a daily basis, is more than a lot of creators want to do. so what's your process there?[00:07:55] Dave:Yeah. I mean, I should emphasize that I do it every day. Not because I think it's some incredible draw for readers to get Daily Content. I do it every day because I'm addicted to it. If my newsletter had five stories in it, instead of 10, it would do better. If my newsletter came out three days a week instead of five days a week, I'm sure it would do better.If it came out once a week, it would do even better then you know, also if I had a more marketable or not marketable, but a more, business-oriented topic that was more narrow, it would do better. I used to write a newsletter that was just on tech and it was. Really popular in the internet professional community back in the first boom, I had about 50,000 subscribers and there were probably about 52,000 internet professionals.So I just like writing about what I want to write about and I'm addicted to pressing the publish button and I'm just addicted to the process. So I do it because of that. I'm not sure that would be my general advice to somebody trying to market or promote a newsletter.[00:09:01] Nathan:Yep. Are there other iterations, either ever before or things that you tried that you realized like, oh, that's not a fit for your personality, your writing style?[00:09:09] Dave:Yeah. When I first started it, I actually, I'm an angel investor also and have been since, probably right after Google and Yahoo launched. so a while, and I used to, my passion has always been writing, so I wanted to mix writing into that, process. So I would send out 10. Daily stories, but they were all tech news related to the CEOs of the companies I worked with and a few of their employees, so that they wouldn't have to spend their time reading the news or worrying about competitors or worry about what the latest trends in tech, where I would give it to them.And they could focus on doing their jobs and that sorta got shared and got out. so I did that for a few years. really, that was my iteration. I should've kept the brand. It was called David Netflix. not that it was a great name, but I've shifted brands about 40 times in my life. Cause I love branding and naming.I that's another, maybe this is more of a cautionary tale than a lesson and newsletter marketing. I would stick with a brand if anybody has the possibility of doing that, that was a big mistake I've made over the years is having multiple brands. But when the bus came, the first internet bust, I basically was writing an obituary column every day and about companies that had failed.So I just decided, I wanted to expand it and I knew I was interested in much broader topics than just tech news. So I expanded it to all news, a critical point that, really changed Next Draft and got it to catch on and become more popular was when I decided to focus on making it more personality driven and less, less overwhelmingly, providing an overwhelming level of coverage.I used to think that I had to provide all the news in the day because people would sort of, depend on me to provide their news. I was sort of selling myself as your trusted news source. So I would include a lot of stories that I didn't have anything to say about because they were huge news, you know, an embassy closed in Iran or whatever.That was huge international news, but I didn't necessarily have anything to say about that that day. So after a while I decided, no, I'm not going to do that. I'm just going to limit it to 10 items. And I'm going to focus that on what I think is the most fascinating and think of it less like a curation tool and more like, a, modern day column.I think if the column newspaper column were invented today, it would look a lot like Next Draft people would sort of share their takes and then provide links off for more information. once I did that, it was a big change. People started signing up much more readily and, once I stopped trying to be exhaustive.[00:11:56] Nathan:That makes a lot of sense to me. I think that that's something you see from a lot of creators is that they're, they're trying to find some model. That's like, this is my idea of what people should want, you know, rather than what they end up doing, eventually it's coming to, it's like, okay, forget all of that.This is what I want. And I'm going to make that. And then people like me can find and follow it. And people who don't can, you know, do their thing. Can you go find one of the other million sources on the internet?[00:12:21] Dave:Yeah. When I think of the people that I like to follow or have followed forever on the internet, all of them are that ladder. They just do it their way. They have a design, they want, they stick to their guns. They say what they feel like saying. they decide. what the personality of the product is.And, they move within that. I always find that to be the most interesting thing, especially when it comes to something like newsletters. I really think newsletters are more like a radio talk shows than they are like other internet content, podcasts to a certain degree as well. But I always feel like I listened to are used to listen a lot to this radio, sports caster named Jim Rome.And whenever he would have a new city that he was launching and he would always give the same speech on the Monday that they launched saying, just give me a week. You might not.Get the vibe of what we're doing today. You might think it's okay, but not great, but just give it a week and listen, and then decide if you like it or not.And I sort of feel like that's how newsletters are your relationship with your readers sort of creates this, sort of insider-y voice and communication that, you, it takes a little while to get into the rhythm of getting it. But once you do, then it's like this familiar voice or this familiar friend that you feel like, even if you didn't read it for a few weeks, you can start a conversation with that person right away easily.That's how I think the voice of a newsletter is most effective. So that's why I've always thought of it. More of what I do is sort of a textual talk radio, more so than a blog or some other format[00:14:01] Nathan:What do you think, or what would you say to someone who maybe had 10 or 20,000 subscribers and felt like their newsletter had gone a bit stale and maybe their relationship to it had gotten a bit stale or they're in this, this position of writing things that no longer have their voice, how would you coach them through like bringing their voice and personality back into it?[00:14:22] Dave:I mean, it's definitely hard. it's hard doing something that you do alone and, something that is often hard to really get off the ground or get to grow, especially when you're on a platform like the internet, where every day, somebody does something and 10 seconds later, they're like internet famous and you're trying day after day.So, I mean, the first thing. Is that you really have to be interested in what you you're passionate about. and focus in on that, because that will alleviate a lot of that stress. Like, do I feel like sending it today? I'm a too burnt out. What's the point? I mean, not that those feelings don't happen. I had those feelings as recently as an hour ago, when I press publish, I have those feelings and disappointments constantly, you know, that's part of being a creator of any kind.Maybe that word is sort of, sort of goofy, but anybody who's putting themselves out there and putting content out, you know, you have that feeling all the time. If you're an indie, and you're doing it all day in front of the computer by yourself, then that's even more powerful because, you know, if you work at a big company or everybody's working on the same goal, or even in a small group, you can sort of support each other and, maybe even bullshit each other at some cases where, oh, no, this really matters.You know, where, if you're by yourself, that has to be pretty self-sustaining or self-sustaining. I do have a friend or two that I always share blurbs with who, one of my friends Rob's, he proves almost all of my blurbs, so it's nice to have that virtual office mate. He's not really officially part of Next Draft, but you know, I don't think I would do it as easily or as, for as long if it weren't for him because he's like my virtual friend on the internet that says, oh, come on, let's get it out today or whatever.So I think that's helpful to have a support team or a couple people you can count on to sort of give you a boost when you need it. But the key really is, is that it's gotta be something that you are passionate about, both in terms of the product and in terms of what you're focusing on, because if you feel strongly about it, then it really.I don't want to say it doesn't matter if people enjoy it, you should take cues from your readers. What are they clicking on? What are they reading? What are they responding to? But at the core, it's gotta be you because that's what gets you through those down points? you know, I had a weird thing because I write about news.The general news, world basically benefited dramatically from the Trump era because everybody was habitually turning on their news, 24, 7, and refreshing and Whitey and Washington post and checking Twitter every two seconds to see what crazy thing happened next. And we're all poor sorta,[00:17:01] Nathan:Wreck to watch.[00:17:02] Dave:So everybody was really into it and it created.Unbelievable platform for people to become media stars. You know, Trump was bad for democracy, but he was great for media. Great for creating new voices out there. whether we like it or not. for me, it was different because I wrote about all news. I wouldn't say I was apolitical, but I wasn't heavily political.The Next Draft had plenty of readers from both sides of the aisle. when Trump came around, it was like one story every day, basically. So it really limited. I would get emails from longtime readers all the time that said, Hey, can't you cover something other than Trump every day?And I say, Hey, if you can find the story for me, I'll cover it. This is what every journalist is on. Now, the people who used to cover the secret service around Trump, the people who used to cover sports are not talking about Trump because of a pandemic relation ship to it. The people who aren't entertainment are talking about Trump because they can't believe that anybody voted for him, whatever the issue was, every dinner party was about Trump.So it was really a bummer for my brand and my product. Actually, it became boring in some ways to me to have the same story every day. And it became, I think frustrating to my readers.But during that era, when it was happening, I had to make a decision. Do I become more political and go full on with this?Or do I sort of try to. Do what I would call a falsely unbiased view or a, you know, false equivalence view that we saw in the media where there's both sides to every story. And you have to pretend they're both accurate, including one guy saying to put disinfectant into your veins. And the other person's saying to wear a mask and take a vaccine, but those things get treated as equal somehow because the president said it.And I really decided, you know, more important than keeping readers is that I'm true to my own sort of ethical standards. In a moment that called for it, at least for me. So I became more political. went into it and I said, what I believe and still believe is the truth, you know, about what was happening with Trump and Trumpism and our slide towards authoritarianism.And I know that this is a podcast more about newsletterish than it is about politics or news, but I'm just sharing that because that's the kind of thing that kept me going. and the people who really cared about what I was writing, appreciated it and would email me and say they got something out of that.And most importantly, my mom would say, yeah, you made the right call. Or my dad would say, yeah, you got that. Right. And ultimately, When it became a sort of a bummer period for me, which I would say 2020 was because of all the horrible news. And, I was writing a book about the year. So I was like living, July of 20, 20, well writing about March of 2020, which I don't recommend for anybody's emotional health.And I just had to think like, what's really important to me. Yes. I want to be funny, which I try to be in my newsletter every day. I want to be read my narcissism is as strong as ever, but ultimately I want to be able to look myself in the reflection of the, darken screen on the rare times that it is dark and say like, yeah, you told the truth and that kept me going there.So I think whatever your brand is, you know, it can be a newsletter about guitars, but if you have that sort of passion, And you have something you want to say, and you think is important to say it sort of gets you through those levels and your motivation. And if it's not getting you through the lows and the motivation, there's nothing wrong with saying, Hey man, this is not worth it.I'm going to go try to make something else. You know, it doesn't have to be, you don't have to beat a dead horse.[00:20:51] Nathan:On the political side. Are there specific things that you felt like it costs you opportunities that it lost you? Because I think a lot of creators, whether they talk about, you know, finance or photography or whatever, I'll see these things. And they're like this either directly relates to me and my audience and I feel like I should take a stand on it.Or it's like a broader macro issue that I feel like we should talk about. And when you do, then there's immediately, you know, somewhere between three and 300 responses of like, we didn't follow you for the politics, you know, or like something like that. And your Instagram, DMS, or newsletter replies or whatever.[00:21:24] Dave:Yeah. it costs me a lot. Definitely it costs me readers or subscribers. It costs me, psychic pain because I was locked into a story that was just overwhelmingly, emotionally painful, really, and shocking and difficult to understand all the things that cause you sort of emotional exhaustion. We're in the Trump story, especially in 2020, when it became a story about our own health and our kids' health.And the frustration level just went through the roof. for me, professionalizing that content actually helps create a bit of a barrier to the feelings about it. Some of my good friends were probably more bummed during 2020 than I was because when the latest crazy story or depressing story would happen, I felt I had to. Ingest that content and then come up with, something cogent to say about it. And maybe hopefully funny to make it a little bit of sugar to take the medicine and then get it out to people. So I've always felt that being able to do that, sorta created a barrier between myself and actually feeling something.So that's another thing I like about the newsletter probably at least unconsciously. but yeah, there was a lot of costs in terms of readers, for sure. Hate mail. but there always is, you know, Today. I would say I get much more hate mail from the far left. If that's what you want to call them. People who feel like every joke is like an incredible triggering a front to their existence or any hint that you mentioned somebody as attractive.I've gotten hate mail because I implied that Beyonce is appearance was part of her brand. I mean, it's totally crazy, but, It's those extremes. You have to be able to turn off. You know, a friend of mine used to work at a major, be the editor of a major American newspaper. And he said every Friday they would get together and they would play the craziest, calls to the editor.They had a call line. In addition to, you could send a letter or you could call, leave a voicemail about something you were upset about in the coverage. And they would just gather around and have drinks on Friday. Listen to this because of course the people who are calling this line are almost self-selecting themselves as a little bit wacko and their takes were usually pretty extreme.The internet, Twitter, social media, Provides, greases the wheels for those people to be more prevalent in our lives. But I think it's really important to know that that's a real minority of people, somebody who sent you a hate mail, that your joke was so offensive, or they can't believe you mentioned that people ever watch pornography on the internet or any of these other things, it's this tiny minority of people.And then it's one step crazier that they felt like they had to contact you. So that's a really hard thing. I think about being split, particularly the newsletter game, because anybody can hit reply and you're going to get many more replies from people with crazy complaints, than you are from people with really thoughtful responses.Not that those don't come and those are valuable and I love getting those, but you get many more from people that just have really bizarre. I mean I could list probably for hours to crazy things that people send me that they're mad about, you know,[00:24:50] Nathan:Is there something specific that you do? Like one thing when I get those replies, if they're just like completely off the wall or abusive or something like that, I just scroll down and then click their unsubscribe link because, you know, they're never going to know, and then I just have to show up in their inbox[00:25:07] Dave:Right.[00:25:08] Nathan:There's something that you do.[00:25:09] Dave:That's not a bad strategy. I like that. I do do that occasionally for sure. occasionally I'll just go to Gmail and just, create a filter for that email to automatically go to my trash. if it's like a hardcore right-winger, that's telling me how stupid I am about ivermectin and that, you know, people should be taking horse dewormer and I'm just not getting the truth.And that Trump is awesome and that, Whatever. I usually just delete, honestly, because I don't see a big benefit to replying to somebody, especially if it's like a rabbit email, you know, they're looking for a reply, they want the conflict. A lot of people sleep easy with conflict. That's one of the lessons of the internet that I learned when I was first starting on the internet, you know, David edix sort sorta became popular because somebody that had a blog with a similar name, that I hadn't heard of, complained that I sort of stole his name because his name was also Dave.And I had got like, probably about three or 400 emails saying, you know, with expletive saying what a horrible person I was. And I also got about 3000 subscribers and at the time I had about 30, so. I didn't know how to respond. I felt like, wow. Number one, I didn't know that guys had the product with the same name.Number two. My name was different enough. Number two or three were both named Dave. I mean, who cares? You know, and plus I don't want to be attacked by anybody. So your first reaction is to respond and a slightly older, although not noticeably these days with my gray beard, slightly older friend of mine who had been in tech a little longer, said, don't respond.This guy lives for conflict. You guys are going to fight. There's going to be this public thing. You're going to be up all night and he's going to never sleep so easy. So, I took that to heart and didn't respond. And I, I think about that a lot when I get rabid emails from people, Mike exception, actually probably my weak point really is from, more my side of the political spectrum, where people who are generally liberal, but are just so extreme for me.In terms of being triggered or having a joke, be every joke, be inappropriate. That those people, I actually do feel like I want to respond to because, I, I don't think I can really motivate or move, somebody who was on the opposite end of the spectrum and is sending me hate aggressive, hate mail, but maybe I can move somebody who's just a little bit different than me, or a little bit more extreme.I will respond to those, although I'm usually sorry. The one other thing I always respond to is if people have been reading, they say, oh, I've been reading you for years. And, I wanted to ask you a couple of questions about this book that you wrote before ordering it. And I'm like, just order the damn book. that's probably my most common email to people these days. It's actually remarkable how many people says, wow, I I've been reading you for years. I share you with all my friends. something, when my sons come home from college where it's always talking about, Dave said this, Dave said that, before I buy your book, I just wanted to ask you a couple of questions to make sure it's going to be for me.I'm like I worked on something for an hour and it's like, your family is talking about it. What, just by the thing I worked on for a year, you know? So those kind of things, personal frustration, I respond.[00:28:37] Nathan:Yeah, that makes sense. okay. I'd love to talk about the book some more, but before we get into that, there's two things I want to talk about. The first one is like, how do you measure success for the newsletter? What's the thing that you'd like to, cause I don't think it's, you're pursuing the monetary side for this.It sounds like the monetary side comes from investing and, and then what's success for the newsletter.[00:28:59] Dave:I mean, I have had right now, I I'm just marketing my, my own stuff. And during the pandemic I marketed non-profits, but, that had to do with either the pandemic or, the democracy issues that we were facing. but I have made decent money from selling straight sponsorships. Year-long sponsorships to people, which I highly recommend.I think some of the ads that people put into his letters that go by clicks or whatever, unless you have a massive audience, it's hard to make much money, but if you pitch to some company that is a like-minded brand, Hey, you're going to be my only brand for a year. And anytime you have special events, I'm going to mention it.Then you can say, okay, you have like, you know, 20,000 readers or a hundred thousand readers that can make a difference to a brand to say, yeah, it's like a rounding air show. We'll give you 20 grand or a hundred grand or wherever it comes in there that you can actually make a decent. Living in terms of writing.So that always worked better for me, but no, my, my internet life is really all about narcissism and, clicks, you know, the dopamine, I just want reads. I'd rather you subscribe to my newsletter than pitch me your startup company. I just, that's what I want the most. So more numbers, more opens, more reads, more subscribers.And unfortunately that's probably the hardest thing to get also, especially in a product that is sort of viral. I think newsletters are sort of viral, but it's better if you have a team and some tools to really get it going. That's, you know, sites like the Skimm morning brew and the hustle. They have teams that are really growth hacking and focusing on that and having rewards programs and ambassador programs.The reason you see that is because.Newsletters themselves are not really inherently that viral. Yes. Somebody can forward it to one person or whatever, but it's not as viral as a lot of other forms of content where you can click a button and share it with all of your followers, like a Facebook post or a tweet.So yeah, the thing that matters to me most is probably the hardest to get in the newsletter game, but that's the truth[00:31:10] Nathan:Yeah. Well, I think the, the point on like newsletters don't have a distribution engine. There's no Facebook newsfeed, YouTube algorithm equivalent for newsletters. And so it really relies on either you posting your content somewhere else, whether it's Twitter or YouTube or medium or something that has an algorithm or your readers saying like, oh, I read Next Draft.You should too. There's not really something else in there. Have you looked at, or I guess if you have thoughts on that, you comments on it, but then also have you looked at launching an ambassador program or, or an actual referral program?[00:31:44] Dave:Yeah, I've thought about him. And now over the last year, there's been a few tools that have come out a few. I think X people from sites like morning view Ru, and some other sites that have sort of perfected some of these marketing programs have, sort of come out with these tools. I've messed around with them a little bit.Some of them still require I find, some technical ones. so I, I have like an engineer who works with me on Next Draft, like as a freelance basis every now and then, but it's not always easy for me to launch stuff that requires a lot of a moment to moment technical support, and management, because it's just me using a lot of, they're customized, but they're over the counter tools.So I've thought about a lot of them, but I really haven't tried it that much.I want to though I do want to do that. I would like to do one of those programs, especially where you get credit for referrals. I think that's the best kind of model. So there's one called spark loop.[00:32:51] Nathan:Yeah, we actually, I invested in spark loops, so we[00:32:54] Dave:Okay.[00:32:55] Nathan:Decent portion of that business, so good.[00:32:58] Dave:Oh, nice. Yeah. That one, if it was just slightly easier, I know that it's probably difficult to make it easier because, there's so many pieces. They have to have your subscribers. I have to have my subscribers, but that is, does seem like a good product. And especially if they can, I think expand into like letting a person sell a product or whatever, get credited for sharing products that can be even bigger.But yeah, that kind of stuff is really powerful for sure. And I, I do want to get into that. it's more just inertia that I it's just a matter of sitting there for the, an amount of hours that it requires to get it going.But I do think that's a great thing for newsletter writers to do, and I'm pretty surprised that more newsletter platforms don't build it right in.I think that'll probably change over time too. Maybe you guys will get acquired by.[00:33:48] Nathan:Yep. No, that makes sense. I know for convert kit, we wanted to build it in, it looks at the amount of time that it would take and then said like let's invest in a , you know, and then roll it into our offering.[00:33:59] Dave:Yeah, it's hard. It's hard not to take that stuff personally, too, you know, for people that do newsletters, you think you're going to put a thing on there and say, Hey, you know, it's just me here and you always read my newsletter and click. I know you love me so much. Can you just do this to get a free whatever?And it's, you know, sometimes not that many people click, you know, or other times like they click just as long as there's the free item. So there's a lot of ways to get depressed. Like I had things where I say, Hey, the first a hundred people who do this, get a free t-shirt or whatever next strap t-shirt.And those hundred people will literally do what I asked them to do in like 34 seconds, you know? And then it like stops after that. The next time you ask them, if there's not a t-shirt. But it's not you, you know, if you go to a baseball game or a lawyer game or whatever, you know, people sit there, they don't even cheer as much for the team as they cheer when the guy comes out with the t-shirt gun.So it's like, people love t-shirts more than they're ever going to love you. And you have to go into these things with that in mind. there's no way, even if it's, even if you're XX large and the t-shirt is, you know, petite, it's still worth more than you are. And the average mind of the average person.So you have to go into all of these things thinking, I hope this works like crazy, but if it doesn't tomorrow, I open up the browser and start writing.[00:35:19] Nathan:Yeah. That's very true. I want to talk about the growth of the newsletter. I was reading something, which I realized later was back in 2014, that you were at around 160,000 subscribers. I imagine it's quite a bit larger than that now. And then I'd love to hear some of the inflection points of growth.[00:35:35] Dave:Yeah, I'm not, I'm not sure. I might've, I don't know if I lied in 2014, but now I have about,[00:35:41] Nathan:Quoted it wrong.[00:35:42] Dave:No, you might've got it right. I might've exaggerated. Maybe that was a including app downloads and a few other things. Yeah. I have about 140,000 or so now, so that would be making that a pretty horrible seven years now.You're depressing me.Your listeners should just stop, stop writing newsletters. It's not worth the depression[00:36:02] Nathan:Just give up now[00:36:03] Dave:Yeah. And by all means if Nathan goals do not pick up. no, yeah, I probably have it 140,000 on newsletter. Made my newsletter. It's hard to believe in this era of newsletters actually, but when I first launched Next Draft, I noticed that even people who would send in testimonials or that I would ask for testimonials would say, basically something to the extent that even though email is horrible, this is the one newsletter I I'd sign up for whatever.And I kept thinking, man, that's a bummer that I'm starting out at this deficit, that people have a negative feeling about the medium. So I, since then I've always made it my goal to. Have the content available wherever people are. So the newsletter is certainly the main way that people get next job, but there's an app for the iPhone and the iPad there.That's the first thing I launched because I wanted to have an alternative for people who just hate email too much. So now you go to the landing page, it's like, Hey, if you don't like email, here's another version. I have a blog version. I have an apple news version. I have an RSS version. I'm lucky enough to have a really good, WordPress custom WordPress install that I just push one button and it pushes it out to all of those things.But I am, I'm a big proponent of just meeting people where they are. even, as an example, I recently launched a sort of a substance. Version of my newsletter under the radar. but when I redo my site, I'm going to make that more clear because if people already subscribed to like 10 sub stacks and they're using their aggregator and they already have their email saved and they can just click a button, it's like, I don't care.You know, it takes me five extra minutes to paste my content into sub stack. So I just want the reads. I don't really care about how they read it or whether they read it.[00:37:55] Nathan:Yeah. That's fascinating. So then let's shift gears a little bit. I want to hear about the book. first I wanna hear about the title. Would you have it on your shirt?[00:38:03] Dave:Yeah. That's pretty embarrassing. I swear. I didn't know it was video today, but I do have a shirt[00:38:06] Nathan:You're good.[00:38:07] Dave:Otherwise I wouldn't have worn. This would have worn my Nathan Barry's shirt.[00:38:12] Nathan:That's right. It's in the mail actually. It's[00:38:15] Dave:Oh, good, good.[00:38:16] Nathan:Big photo of my face.[00:38:17] Dave:Yeah. Convert kit. My wife converted to Judaism before we got married. So I have my own convert kit.[00:38:23] Nathan:There you go. Exactly. so I want to hear like what the book is about and then particularly where the title came from,[00:38:30] Dave:Sure.[00:38:31] Nathan:It made me laugh a lot when I heard it.[00:38:33] Dave:Oh, cool. That's good. That's a good start then. yeah, the title comes from, in July of the, of 2020 when the pandemic was really setting in and becoming a reality for everybody. this amusement park outside of Tokyo in the shadow of Mount Fuji called the Fuji queue. amusement park reopened.And they found that even though everybody w everybody was wearing masks, people were screaming so much on some of the rides, especially the Fujiyama roller coaster, which was their scariest ride, that they were worried about germs spread. So they sort of put signs around the amusement park saying, no screaming, you can come, you can ride and have fun, but keep your mask on adults scream.And it sort of became a little minor social media thing in Japan, where people were sort of making fun of them like, oh, they're telling us not to scream. How can anybody not scream on the Fujiyama roller coaster? So in response, the, park management had to have their executives with perfectly quaffed hair and tie and colored shirts and masks on ride the roller coaster with a webcam facing them the whole time without moving a muscle.Cracking a smile or grimacing or screaming. And then at the end of the ride, when the rollercoaster stops, it says, please Scream Inside Your Heart.And that was always my favorite meme of, 2020. It went really viral. There was like t-shirts. aside from mine, there were posters memes. It sort of went crazy for about a week or two, which by 2020 standards is a pretty long time for a meme to last.And I just thought that made sense as a title for the book, because that's sort of how we felt, all year that I dunno if we were screaming in our heart, but we were certainly screaming into a void. Like no matter what we sat or yelled on social media or complained to our family members or friends, it just kept getting worse.The year just kept getting worse. And, so the idea is that this book sort of, now you're free to sort of let out the scream. And the book is it's about 2020, certainly, but it's really about the issues that led us to 2020. There's a ton about our relationship to media and including my own relationship to media and how that got us into trouble.Some of the stuff we're talking about today, how, technology has impacted our lives stuff. I've been sort of thinking about it, writing about for the last few decades, and a lot of the political hate that emerged. and, but it's all within this time capsule of the craziest year.[00:41:12] Nathan:Yeah. Yeah. And so that's coming out early in November, November 2nd. so you're, it looks like you're just starting the, you know, mentioning the promotion tour and all of that. is there a big, big push that comes with it or are you kind of, I, I'm always curious with people's book launches, what strategy they take.[00:41:30] Dave:Yeah. I mean, I'm a newbie, so it's, the whole process has been interesting to me working with a publisher, working with others, is not my forte. so I got used to that or I'm getting used to that and they're probably getting used to it also because working with grouchy 50 something in these is probably not ideal, but, yeah, I've just been promoting it so far in Next Draft, but I've been doing, I have a PR company that's helping me and I've been doing a ton of podcasts and I'm marketing it to my own readers.And then as it gets a little bit closer to the November 2nd date, I have a lot more stuff planned rut, a lot of influencers have early copies of the book, and hopefully they'll promote it. And, I'll call out a few favors from bloggers and hopefully newsletter writers. I feel like that should be my in theory.That should be my secret weapon because, in addition to being fun and creative, nothing moves traffic, except maybe Facebook, nothing moves traffic more than newsletters. I know a lot of people who run e-commerce companies and newsletters are always second, if not first, in terms of traffic drivers.So, I really think that, if some of my friends out there at morning brew in the hustle and the scam and all these other sites that sort of, have surpassed my size by quite a bit, put the word out that, one of their fellow warriors is, has a book out. That'll probably move the needle even more. The media, I'm hoping to get stuff like that, but I really don't know. I'm trying not to get my hopes up too much because, unlike a newsletter, it's not just one day's work, you know, you like worry about one word or one sentence in a book for like three weeks and then you put it out there and people are like, oh yeah, I'll check it out sometime.Thanks. So, you know, that's, you know, whatever that's life as a, you put yourself out there, that's how it goes. So I'm hoping it sells well. And, the more people that get it, I think some people, their first reaction is, oh my God, 2020. I don't want to relive that again. But, hopefully people who know my brand and those that they share it with, know that it's, you know, there's a lot of humor and there's, it's probably 30 pages before we even get into the first event of 2020.So it's, there's a lot more to it and it's sort of fun and crazy and tries to have the pace of a roller coaster. that was the other thing I took from the Fujiyama roller coaster.[00:43:59] Nathan:Yeah. So one thing that I'm always curious about with people who have like a prolific newsletter, you know, in your case of writing every day, and then like, for a lot of people, that would be a lot to handle of staying on top of a daily newsletter. And then you're writing a book on top of that. How did you schedule your time?Were you blocking off like, oh, these afternoons are specifically for book, book writing. Cause you turned it around relatively fast.[00:44:24] Dave:Yeah. the newsletter is sort of like a full-time job. People always ask me, you know, when do you work on, or how many hours do you spend on it? I mean, I'm, I'm always looking for news, whether it's on Twitter or friends, emailing me stuff or texting me stories, or just in conversations with people to see what they're into or what stories are interesting them or what I'm missing.In terms of actual time spent like where I'm dedicating time. I probably do like about an hour every night, because the story has changed so quick. So I'll do an hour of looking for stories every night. And then the next day I sort of lock in from about nine to one, usually, or nine to 12, where I'm finding stories, saving those stories, choosing what stories I want to go with and then actually writing the newsletter.All of that takes about anywhere from like two and a half to four hours, depending on the day I go pretty fast. When it came to the book, that was tricky. It was actually more emotionally tricky because like I said before, I was like, had to go back and write about, you know, Briana Taylor while I'm living another horrible act, you know, or even more so the Trump, you know, one crazy Trump thing and another crazy Trump thing and seeing the pandemic getting worse and worse.So that was stressful. But I found at the beginning I would try to write a lot at night and that was okay. But I found actually if I just kept going, in the day when I was already rolling and had written the newsletter and I was already in the group just to add on an hour or two to that was actually easier and more effective for me than trying to get going.But that's just me. I mean, I just go by my it's almost like my circadian rhythm or something like that, I almost never eat or consume anything before I'm done with next job except for coffee. I would keep that going, you know, once I would like, sort of have a sandwich or whatever, then it's like, oh, let me just take a quick nap and then whatever.So, yeah, I tried to just keep it going. I always find the more consistently busy I am, the less I procrastinate. And if I take a day off or I take a few hours off, even then, between writing, it just, it takes me longer to get going.[00:46:37] Nathan:Yep. That makes sense. The habit that I'm in right now is starting the day with 45 minutes to an hour of writing and that's working much better for me than like slotting it in somewhere else. So I think like w what I hear you saying is like, experiment and find the thing that works well for you.[00:46:54] Dave:Yeah. I mean, if you're going to start experimenting almost every writer, I know not like newsletter writers, but just general writers, all do what you just described. They sort of pick a time in the morning and they get their output done. then the rest of the day, if ideas come to them or whatever, they jot it down, but they're sort of powering in that morning hours.[00:47:13] Nathan:Yeah.[00:47:14] Dave:That's probably a good one to try. Although, you know, some people just do it better at different hours. I'm sure.[00:47:19] Nathan:Yeah. another thing I realized, I've always you for years, and until we got on this video call, I had no idea what you looked like. and which is kind of an interesting,[00:47:28] Dave:Well, I'm sorry.It's by design. I have a face for Panda.[00:47:32] Nathan:Tell me more about, well, I guess two sides, one, has there ever been an interesting interaction? You know, because you're like, Hey, I'm, I'm Dave and people are like, I wouldn't have ever recognized you. Or has there been any other benefits and thought behind, you know, why it have an avatar?[00:47:49] Dave:If by interesting you mean horrible? Yes. There's been many interesting interactions with people. I mean, before, before I had my current, avatar, which is, pretty awesome, actually, a guy named Brian Molko designed it. I had this incredible drawing of a character that looked like me that, had sort of ether net, Machinery and cord going into his head and it was like me, but my head was actually lifted.The top of my head was lifted off and you could see all this machinery and it was an incredible graphic, by this guy named Sam Spratt. Who's now done, album covers and book covers. He's like a super talent. If you want to follow somebody fun on Instagram, he's just incredible. And it was a drawing, even though it looked photo realistic.And I used that for a while and then I would go places and people would be like, you are so much fatter and grayer than I imagined. And so instead of having Sam sort of ruin his artwork, I went back with the more, cartoonish or animated, avatar. So since then I don't get too much of that, but, that was a good move.Although that's the best thing about avatars and the internet is that your avatar never ages. It always looks the same. It stays the same weight. My avatar never overeats he exercises right here. Angie really gets along well with others and doesn't have any kind of social anxiety either. So he's pretty cool.Yeah, it goes a little downhill with me in person. So[00:49:21] Nathan:Yeah. So is it, that's something that like, it gives you some distance between you and readers, or it gives you some anonymity that, you know, you don't want to be recognized in the streets?[00:49:32] Dave:No, no, it's, it's, basically just what I described. It's like, I literally prefer the, the attractiveness of my avatar versus me, but also actually my avatar is really awesome. my logo, so it's also iconic and scalable. so it looks awesome on t-shirts even people who don't know what Next Draft is when they see, by son wearing his t-shirt, whatever, it just looks awesome.So that that's that's as much of it as anything. I thought your response was going to be mad. You seem perfectly attractive to me. I don't know what the issue is, but no, you went with, am I doing that for some other reason? Yeah. So, I get this all the time.Cause my wife is a very attractive person also. So when people meet me, they're always like, whoa, we were once a very famous celebrity came up to me and I said, oh, I'm Gina's husband. And she was like, wow, you did well. Oh, you know? So I'm like, thanks a lot. That helps. So just gave her a picture of my, my icon and walked away.[00:50:31] Nathan:Then that worked. I'm sure that she has it framed in her office, from now on. it's just interesting to me. You're you're sort of at this intersection between personal brand and, like media brand. And I think the avatar helps push you over into the media brand side. and I don't have any real commentary on it other than I find it interesting.[00:50:53] Dave:Yeah, no, I think there probably is some of that. I I've never really been a fan of using my actual face, or my actual person as a logo. I love the process of designing or working with people to design logos and taglines and all that. But yeah, probably at some point there was a, a goal with Next Draft to make it seem bigger than it is.I know a lot of people that are solo operators. They regularly say we, when they're talking about their brand to make it seem bigger, I actually think that's sort of been flipped on its head though. in the last few years where so many people are coming into the space, it's very clear that what they're doing is leaving a big brand, leaving a we and going to an eye.And I think it's actually a selling point in a lot of ways. So, I mean, I, I still get a lot of emails that say, I don't know if anybody at Next Draft is going to read this email, you know, or if you do, can you get this message to Dave? He's an asshole or whatever. And it's like, I'm the only one here, you know, or the other one I always get is when I email back to people that go, oh, I can't believe you actually emailed back.I didn't think this would get to anybody. It's like, you hit reply. And it had my email, like where else would it go? Exactly. You know? But I think actually having people thinking of you as a person, instead of a brand, Is a benefit today. Whereas if you would ask me when I was younger, I probably would have said, make it seem like you have a big company behind you.[00:52:24] Nathan:Yeah. And I think that that indie shift overall, like people are looking for that.[00:52:29] Dave:Yeah,[00:52:29] Nathan:Want to ask about the intersection between your investing and the newsletter. like, are you still actively investing today and doing author.[00:52:38] Dave:Yeah, yeah, no, I, I still invest a ton. I usually follow along with people who are a little more in tune with today's companies than I am. I don't really go out there and brand myself as an investor much, but I've been really lucky. I have very little intersection actually, if any, with my newsletter and my investing and I definitely want people to. To think of me as a writer first, for sure. Not as an investor who has this hobby, because that's definitely not in terms of time or passion, the reality. but I've been really lucky over the years that, I've invested with people or co-invested with them that were cool with me. branding myself as a writer first, but still looking at deals that came through their brands because they were branded as BCS or investors or angels.That's probably a bigger deal now than when I first started. There were like five angel investors, basically. Nobody really did small, early stage seed deals. you know, I mean, we all knew each other that did it and now there's like thousands of them. So you really have to be either a really pretty well-known entrepreneur or you have to. Sort of attach yourself to our organization or two who are really branding themselves well, getting out there and building a stable of companies,[00:53:58] Nathan:Yeah.[00:53:59] Dave:It's pretty different, more, much more has changed about that than the newsletter game, actually, which is pretty much the same as it was the day I started actually.[00:54:07] Nathan:Are there a few of those I'm curious who are a few of those, people that you would tag along with, you know, when they're investing where like, oh, this person puts money into something I'd like to be right there with them.[00:54:19] Dave:I mean, I have some people that are like entrepreneurs and former entrepreneurs that do it, and if they like it I'll do it. but generally I co-invest with, at any given time, a different group of people, used to be a larger group. When I first started out, my whole investing career, I've co-invested with this guy named Bob zip who's much smarter and much wiser than I am about all things business and.Startup world. So that was really great. And he used to work at a company called venture law group in the first boom, and they represented Google, Hotmail. eGroups all the big, huge, early internet companies, and so he really knew the space well. And when he became, I used to get deals from him.That's how you used to get deals actually was by a couple of law firms that focused on startups. I've been co-investing with him all along and he's been generous enough to, he left the law firm a long, long time ago and became an investor primarily. And he had a fund and was well-known guy and well-respected guy.So I got to sit in when he would hear pitches. and we sort of, we weren't investing together out of the same fund, but we would sort of make our decisions together. And we still do that a lot. these days, I almost always follow along with a guy named run-on barn Cohen and a really good friend of mine.He was for many years at WordPress, basically, most of the things that make money at WordPress, he did. and now he's a investor at a VC called resolute. If anybody's looking for a good VC, he's like incredible, like Bob zip much, much smarter than I am about this stuff. Unbelievably ethical, great business sense.Great technical sense. so I mostly just follow him. So if he does something that's usually good enough for me. And if I see something that I think it's good, I'll pass it along to him, but it's mostly that, but I've been really fortunate. I can't express that enough, that I've been able to invest in companies without having to spend all of my time, branding myself as an investor.That's just been unbelievably lucky. So, I've been able to focus a ton of my energy on my six.[00:56:31] Nathan:That's right. I'm writing a newsletter about the news. I guess, as you're looking to grow and continue on, right? Like the next phase of readers and, and all of that, since we can just say directly that we're all narcissists and we do this for the attention. what's what's sort of that next thing that you're looking for, it's going from 140,000 subscribers to say 200,000 and beyond.[00:56:54] Dave:Yeah, well, I'm, I'm hoping that, I'm not just trying to sell my book here. I'm hoping that the book and the newsletter will sort of have, a coexistence with them because the new the book is really an extension of the brand and the brand is that icon to Next Draft. So I'm hoping that the tricky part about writing about marketing a newsletter, like we discussed earlier, there's not really a natural virality to them.So. You Have this piecemeal growth from people telling each other or their friends or forwarding it to somebody or maybe occasionally tweeting or sharing a Facebook link. Oh, you should check this out. But it's all sort of small little blips. If you get a news story or a big blog story about it, or another newsletter recommending you, that's probably the fastest way people grow these days is by, co-sponsoring each other's newsletters or co-promoting them.Those big hits are more rare and they usually require like, I've had a ton of stories written about Next Draft, but most of them a long time ago, because it's basically a similar product to what it was when they wrote about it the first time. So they're like, Hey, I'd love to write about it, but what's the hook.What's the new thing, you know? so I'm hoping that the book provides that emphasis. It's like, we're doing now a ton of people who may by either been on a podcast in the past, or they've wanted to do a podcast with me say, okay, now's a great time. I'd probably want to move your book and, we can set something up.So it's sort of as an impetus. So I'm hoping that that will be the next big newsletter thing that most, most people who write about the book will also write about the newsletter and the two things can sort of grow together.[00:58:35] Nathan:I think that's spot on.[00:58:36] Dave:That's in terms of, you know, marketing and promotion, otherwise, I do want to try, one of these referral programs because people definitely do like products.And, I am lucky that my icon looks really good on shirts so that people actually really want them. And I have a great designer named Brian Bell who makes all of my shirts.[00:58:58] Nathan:There's something like when creators thinking about products, often if you spread yourself too thin, you're like into the newsletter, the book, the podcast, and like the 14 other things that you could make all at once you sort of hinder the growth of each thing, but then if you really build one of them up to a significant level, then at that point it can start to stall out and by shifting to another medium or have it like launching another product in this case, the newsletter to a book, then that book can have a bunch more momentum that feeds back into it.And so there's just sort of this interesting balance of like, no, When to like, keep pushing on the thing that you have versus when to add the next thing that like, then they feed off of each other and go from there. So I think you're doing it with good timing.[00:59:45] Dave:Hopefully it'll work. All that kind of stuff is the tricky part of doing this stuff. Especially stuff like podcasts and newsletters that are—it's really a ton of word of mouth, unless you get lucky and get some press, and word of mouth is just slow.There's some point where you're going to hit a tipping point where you're going to go from five or 10,000 to like 50,000 much quicker, more quickly because instead of three people going home and saying, “Hey, did you ever hear of this newsletter?” there's like 30 people going home and saying that. But, even with that they hit a plateau, and then you figure out what's the next thing. That's why doing something you're into is so important.And I don't think it's bad to try those other mediums or stretch yourself out, because you never know you might've been writing a newsletter three years, and then you do a podcast and it catches on. For some reason, you're like awesome. Less typing, more talking, let's go. So, but it's tricky. I wish I was better and had better advice for people on promotion and marketing.I'm not awesome at it, and it's not in my nature. So, begging for favors or telling people, even in my own newsletter, to buy my own book is very painful for me. I'm very sensitive to criticism about it. So, if people just all bought it and then made everybody else buy it, that would be a huge relief for me.[01:01:13] Nathan:That would be great. Well, along those lines, where should people go to subscribe to the newsletter, and then follow you on your preferred channel, and then ultimately buy the book?[01:01:24] Dave:I don't want like two or 300,000 people taking my site down. So let's go with if your last name starts between A and M you can start by going to NextDraft.com and sign up for the newsletter there. Or, you can also just go to the App Store and search for Next Draft. If you're N through Z, you can start with the book, and that's at: PleaseScream.com.It has links to all the various audio, and Kindle, and hardcover versions.[01:01:50] Nathan:That's good. I liked how you split the traffic, that way there's no hug of death, and we'll do well there.[01:01:57] Dave:I don't want to get fireballed.[01:01:58] Nathan:That's right.Dave. Thanks for coming on. This was really fun.[01:02:01] Dave:Yeah, thanks a lot for having me.

Jessica DeFino is a freelance beauty journalist living in Los Angeles, California. For the past seven years Jessica has been writing, researching, editing, and publishing about the beauty and wellness industry. Her work has appeared in Vogue, The Cut, Fashionista.com, Cosmopolitan, Marie Claire, Business Insider, SELF, HelloGiggles, Harper's Bazaar, and more.Before starting her career as a freelance journalist, Jessica worked as a beauty writer for The Zoe Report. She was Director of Communications at Fame and Partners, and worked as a ghostwriter for Khloé Kardashian and Kendall Jenner.Jessica earned her bachelor's degree in Music/Business Songwriting from the Berklee College of Music. Jessica's music degree brings a unique perspective to her writing. It infuses each piece with lyrical qualities of storytelling, flow, and connection to her audience.Jessica also publishes a bi-monthly beauty newsletter called The Unpublishable, where she shares “What the beauty industry won't tell you — from a reporter on a mission to reform it.”In this episode, you'll learn about: Making lasting connections with your audience Why understanding music and rhythm makes your writing better Capturing and keeping your readers' attention right from the outset The dangers of cross-posting your content across social media Links & Resources Vogue Magazine Allure Harper's Bazaar Ursula K. Le Guin RhymeZone Ali Abdaal Jessica DeFino's Links Follow Jessica on Twitter The Unpublishable Jessica's Instagram Episode Transcript[00:00:00] Jessica:I started writing as a songwriter. The musicality of something is very important to me. So I'll read my own stuff out loud sometimes. I feel when people can read something and there's a clear flow and rhythm to it, and the words melt into each other sound nice next to each other, it locks them into the content early on. You want to keep reading because if you stop reading it's like you're breaking this rhythm that you've started.[00:00:34] Nathan:In this episode I talk to Jessica DeFino. She's a journalist covering the beauty industry, but she tends to take an approach that's not as popular with sponsors and publishers, because she's anti a lot of their products and a lot of the nonsense that is put into the products and the marketing behind it.She's taking a critical angle and she's well loved by her readers because of it, but maybe not so loved by the big brands. We talk about how that came about. We talk about her writing style, her approach of using her background in song writing and going to school for songwriting to have a better, more interesting writing style.She gives some tips along that angle, talking about how she launched a newsletter last year and growing that to 9,000 subscribers. How that is a backbone for the rest of her work she does in journalism.It's a great conversation. So, let's dive in.Jessica, welcome to the show.[00:01:28] Jessica:Thank you so much for having me.[00:01:29] Nathan:We'll jump around a whole bunch, but I want to start on the launching of your newsletter. What was the moment when you started to think, okay, I want to actually run a newsletter and start to control my own audience?[00:01:44] Jessica:I had been toying with the idea for a while, and then I think it was, April, 2020, right after the pandemic, where I had gotten into a situation where—I'm a freelance reporter—I had four freelance stories out when March happened, and Coronavirus lockdowns happened and everything was up in the air.The company severed ties with all of their freelancers and basically gave these four unpublished stories back to me, and gave me a kill fee. So it was like I had reported out these whole stories. I had spent months on them, and now I had nowhere to put them, and I gave it about a month of pitching it out to other alums.There weren't any takers because media was in such a precarious position at the time. Finally I was like, maybe this is the opportunity I've been waiting for to launch a newsletter. and I decided to call it The Unpublishable because I couldn't get anyone to publish this. And yeah, it's been going, almost like every other week.[00:02:50] Nathan:Nice. Yeah. It's interesting how these unfortunate moments result in something that's like, okay, this is actually either a good thing now, or hopefully going to be a good thing soon, but it starts with difficult times.[00:03:05] Jessica:Yeah, exactly. I wanted these pieces to be big. They were stories that I thought were important to tell, and I really wanted them to be in a major outlet. Sometimes with media, you can't sit on things for very long. It was like, I maybe have two more weeks before they stopped becoming relevant.[00:03:23] Nathan:Yeah. So for context, for anyone listening, what were some of those stories as an example?[00:03:27] Jessica:The first story I published with a piece called “Where are All the Brown Hands?” It was a look into the overwhelming whiteness of the top nailcare companies in beauty. If you would look at their Instagrams or if you would look at their websites, everything was modeled on white hands.As a beauty reporter, when I have to source images for the stories, I don't want to just be showing white hands. If I'm writing about nail trends or whatever, and it would take me hours every week to comb through places and try to find the trend I was speaking to on a person of color. At one point, I was like, why is this happening and how come it's so hard?This should not be hard. So, I wanted to do an investigation into it, and just like that the whole process had already taken six months. I was like, you don't know what's going to happen in this story. It might be scooped. It might be written by somebody else. It might be irrelevant in another month or so.So, I really wanted to get that out there, and that started it.[00:04:31] Nathan:When you publish a story like that, and you're used to publishing for a major beauty publication, but you're publishing it for yourself. What did that look like? What was the process of saying, I have this story that I've worked on for a long time, and I have a brand new newsletter and all at once.How did you bring that to life and pull the audience together?[00:04:52] Jessica:Well, luckily at that point I had a mask, a little bit of a social media following just from my work on work, like major publications. Like I had been writing for Vogue and allure. Harper's bizarre. And I had been pretty diligent about building up a social media audience. So I had a pretty sizable, amount of readers just from Instagram.And a couple of years prior, I had like tried starting my own beauty content platform, but I never really had the time to dedicate to it. But I had a small email list from that, from when I was still doing it. So I kind of like funneled all of that together under this new umbrella of this is going to be like my personal reporting newsletter and I kind of got the word out on Instagram.So it ended up reaching like a surprisingly large audience for something that was like a first-time newsletter.[00:05:44] Nathan:Yeah. So if you don't mind sharing how many subscribers were like to that first article?[00:05:49] Jessica:I think that first article probably went out to like 1500 subscribers[00:05:53] Nathan:Okay. Yeah, but that's you're right. That, that is a surprisingly of like, here's the first thing that we're doing.And I guess it goes to show from right. Spending a whole career being known and, and building it in this space. And then, you know, you're not starting from scratch when you funnel entity.[00:06:10] Jessica:Yeah, it, it had always been important to me to, not as important, but it was something I thought about to collect email addresses and to get social media followers, because my goal had always been to write a book. And I know that when publishers are looking at whether to buy a book from you, it matters what kind of audience you have and how many people you have on an email list.So even though I wasn't sending things out prior to finally launching the newsletter, Collecting emails here and there. Just, just to have for the, for the book pitch one day.[00:06:42] Nathan:Yes. That's something that I've always heard is, you know, from agents and friends who are authors and all of that, as they talked about the, the email as being the thing that the publisher is looking for, they're like, Yeah, that sounds good. First question.[00:06:57] Jessica:Yeah.[00:06:57] Nathan:I mean, they use it as a proxy for how many copies can you sell?[00:07:01] Jessica:Exactly. Yeah. When I was pitching out my book, it was all about, Instagram. I, this was probably like two years ago now. and I couldn't get an agent to talk to me until I had 10,000 Instagram followers. So that's like, all I cared about for maybe a year, I was like, I don't care. I'm not going to put effort into anything else.I just need these Instagram followers.[00:07:23] Nathan:Yeah. So you have 35,000 followers on Instagram now. what were the things that worked for you as far as growing that, that audience on it?[00:07:32] Jessica:Honestly, in the beginning, when I was like, I need to get to 10,000 followers, I was a little scammy about it. I did a lot of the like follow unfollow. So I followed a ton of people who were following accounts that were similar to mine.And kind of, and what you do with that is like, they see that you followed them, they check out your page.Hopefully they follow you back. If they don't follow you back, you can like unfollow that person to keep your ratio looking good.[00:08:00] Nathan:So is that like going through and following like 50 people a day kind of thing or hundreds[00:08:05] Jessica:Yeah. I mean probably 50 to 200 people. Like I would spend probably an hour or two hours a day just doing. Stupid stuff like that, but I didn't really care about, but I was like, I'll do anything to get a book deal. If it's following 200 people a day, that doesn't bother me. And if at the end of the day, they're looking at my profile and saying, Hey, this is somebody whose content I care about.I'm going to follow them. It doesn't feel like bad or wrong to me. So I just did a lot of that[00:08:34] Nathan:Yeah, it's a very small way, like small and non-intrusive way to be like, Hey. Do you want to pay? Like, you're just sort of raising your hand and people either go like no, or they go, oh yeah, I'll look at that for a second.What's interesting is I think that a lot of creators started in that way, but probably now when they tell their story, they're like, yeah. You know, I just, I just put out good content and then the content itself. And before you know it, I was, you know, internet famous, you know,[00:09:01] Jessica:I think that worked, it worked like 10 years ago, maybe even five years ago, but right now there's just so much content out there on every platform. And I don't think it's fair to say that if you have great content, you will be successful on that alone. Like, I think you need more than that today.[00:09:18] Nathan:Yeah. So, so the following, people in the space, which we'd recommend, you know, regardless, what are some of the other things, on that quest to 10, that will.[00:09:27] Jessica:Yeah, I was falling up a storm.I was liking a ton of stuff cause that's kind of the same strategy. Like sometimes Instagram too will phrase your account. If you like too many things or you. follow too many people. So I was getting into that. I did a ton of hashtagging at the time. luckily the, the area that I write to to beauty has like a very big and dedicated community on Instagram.So there are a ton of like beauty community hashtags out there that I was following and getting involved in and commenting and just really making my presence known in this community while at the same time posting my own content. That I thought had a very different point of view that would be intriguing to people.So once they saw that I was engaged, they were like, who is this person? And there was, you know, a lot of content there for them to, to delve into.[00:10:18] Nathan:Yeah, that's good. In the last, episode of this show, I had a YouTuber on his name's Ali doll and he's got, you know, he's built up to 2 million subscribers on YouTube, but he talked about that like back catalog that you have of when someone comes across your work for the first time, like seeing the back catalog and seeing it have a unique point of view.And I feel like. That would be the experience, you know, when you pop up in some little way. Okay. Another, you know, beauty, Instagram account, and then you come in like, oh, this is actually different. Has a unique point of view. So, I'd love for you to share. I don't know what the, the short version of like the different perspective that you're bringing to the beauty industry and what someone would notice when they come to your Instagram or your, newsletter.And they're like, this is different. This is a, you know,[00:11:08] Jessica:Yeah.[00:11:09] Nathan:Challenging.[00:11:10] Jessica:I think the easiest way to put it that most beauty content out there is very fluffy. and very positive and very product heavy. and my stance is very beauty industry critical. and I, I say that I'm pro skin anti product. So I'm much more interested in how beauty applies to like your actual skin and your actual body and like the human itself, rather than this external product, you can apply some very focused on the science of how human beings work rather than the science of like a skincare and.[00:11:44] Nathan:Right. Okay. Is there an example that comes to mind of something where you're like, do this? Not that.[00:11:50] Jessica:Yeah. I mean, probably the biggest example is just, I mostly tell people to stop using skincare, you know, period. End of story. Just, you don't have to, our skin does all of that for us. You know, humans have survived millennia without pre bottled products, and there's no reason why. In the past 30 years, our skin has suddenly evolved to need a 10 step routine.It doesn't so, yeah, I just tell people, stop using it. And they're shocked at the results all the time.[00:12:20] Nathan:I like that. I could see a conflict in. Message and business model in the industry. and your interaction in this. there's a lot of money in the industry of obviously selling, I mean, any product, but especially a product that you need to buy every month or every three months or something like that.Like that's a very good business. So have you had any, any conflict of publications not wanting to pick up your stories or any of those things as the publication is. You tell your people to not buy our sponsor's products, you know, or something like that.[00:12:55] Jessica:Oh yeah. I mean, there's been a ton of pushback and depending on what platform I'm writing for, I. See my work being edited in a certain way or softened in a certain way or a brand name being taken out. I've had articles be published and then the platform takes them down almost immediately because an advertiser has complained.I've had legal action threatened against me while I'm reporting for a story just for asking questions. yeah. Yeah. It's that kind of stuff happens all the time because in beauty journalism, there is a huge. Conflict between what you're supposed to be writing about and who's footing the bill for that content, which is products and advertisers.And I think in the beauty industry in particular, there's this extreme lack of objectivity where, you know, editors and journalists and influencers are all gifted product or taken on press trips. And. And given money to review products in a way that in any other industry, you wouldn't be able to call that journalism.You know, there's always gotta be some sort of separation there. Like a typical journalist is not allowed to accept gifts in the beauty industry. It's the complete opposite. It's like, well, how can you write about our product if we don't gift it to you? So it's, it's a very weird space that is very reliant on gifts and money and advertising.[00:14:18] Nathan:So how has that changed as well as you've launched your own newsletter? I imagine you're still doing plenty of freelance writing. Is that.[00:14:27] Jessica:Yeah. Yeah. I'm still, my, my thing is, is I try if I have a story I want to tell, I obviously want to tell it to the biggest platform possible. And then if I can't get the story placed somewhere else, I will, I will tackle it for the news.[00:14:43] Nathan:Okay. So yeah. How has like, has the news that are helped? Like, for example, you're trying to get us started placed and they're like, sure, we'll place it. But could we do this version of it instead? And, and you know, maybe you're saying that like, no that's okay. Whereas before the paycheck might've mattered more or how's That. relationship?[00:15:01] Jessica:Yeah, that's pretty much spot on. I, I didn't really push back too much before, but now that I have. platform that like actually brings in, okay. Money for me. It's not like if I say no, I don't want that story published this way. It's really not like I'm losing out on a paycheck anymore because I will make that up from my own subscribers.So, I think since I've launched the newsletter, there have been two instances of that where I've written a story for a platform have been uncomfortable with the edits and actually. And was like, no, I don't, I don't want to publish it this way. And that feels really good to have a little bit more control over, over what I want to say and the information I want to put out there.[00:15:45] Nathan:Yeah. I mean, you have even more, I mean, you, you always had agency, right. But now it's like, you have an alternative instead of like, I'll keep pitching it to someone else who might have the same objections or, or that kind of thing. On the business side what's well, actually, maybe if we dive into the newsletter today, right?So that we talked about where I was at a year ago when we launched to, I just said, we, when you launched, I had nothing to do with my launch. There's no Royal we in that are taking credit later. when you launched, you know, a year and a half ago, there was at 1500 subscribers. where's it at today,[00:16:24] Jessica:I'm at 9,000 subscribers now.[00:16:26] Nathan:Right?[00:16:28] Jessica:But, I mean, I have a model where some of it is free and some of it is paid, so there are like different cohorts within the subscriber-based too. But like, I'm, I'm pretty happy with how it's grown on the free side so far.[00:16:41] Nathan:Yeah. And so on the paid side, you're charging $7 a month, or 77 a year. What was the thinking on the pricing there? Was that something that you like agonized over a lot or was that a, like, we'll just go with something and see how it works.[00:16:54] Jessica:Yeah, I didn't agonize over it too much. I started out at $5 a month and, after I got maybe my first hundred or 200 paid subscribers and I felt really good about like, wow, that feels like a lot. That's like a good chunk of change I didn't have before. And then when I was looking into the fees that were taken from like Stripe processing, from sub staff, I was taking home like closer to $3 per subscriber.And I was like for the time and attention that I want to give this project, I'm just not going to be making it. At $5 a month until I hit a certain number of paid subscribers. so I decided to bump it up to seven, just to sort of motivate myself to put the time and attention into it that I wanted to give it because if I wasn't going to be bringing in like, actually $5 to me, it didn't feel worth it.So by pricing it at seven, I get more like $5, which felt like a, okay, I'm happy with that number. now that I do have more paid subscribers, I am toying with the idea of, of lowering it because I feel like I feel like from, at least from my perspective, when I am subscribing to a newsletter,I subscribe to a ton of them.I'm much more interested to click. I'm much more likely to click pay and subscribe if it's $5.And if it's like six or seven or eight,[00:18:21] Nathan:You think about[00:18:22] Jessica:Eh, that's kind of a lot. Do I care enough about this content to pay that much? But personally for me, $5 is like a whatever I'll I'll subscribe kind of thing. So I, I think I'm getting closer to the point where I feel like I have enough of a base that I can do that and hopefully reach more people.[00:18:42] Nathan:Right. Okay. I have so many questions here, but diving into the psychology side of when you're deciding to subscribe to something, right? Cause everyone listening is Ryan newsletter and asking these same questions. Like, should it be $5? Should it be $20? Should it be free? Shouldn't be $2. You know, like any of these things.And then they're analyzing their own buying habits. And they're like, but what if it's a business versus a fitness versus, you know, any of these, like what category I'm in and what are those other things that you notice beyond price? When you as a newsletter consumer, I go to like instant subscribe versus like, well, think about this.How many articles have I enjoyed from the recent layer? Like that, tips it over to the other side.[00:19:25] Jessica:Right. Oh, I don't know that there are that, like my personal revelations will be. relevant to people. I personally, just because I run a newsletter, I love to support. So if it's anything that I'm like vaguely interested in and it's like $5 a month or less, I don't know why $5 is my cutoff, but also subscribe.And I'll just see what it's like for a couple of months. And if I don't like it, Whatever I can always unsubscribe, but I just really love the idea of putting that abundance out there into the universe and just being like, I'm a little bit interested in this and I want to support this creator because I know what a, like a hustle it is.I'm sure the average, like newsletter consumer doesn't really doesn't really think that way. but for me, I don't know. I love a good headline if it's like a good quippy, funny headline, like I want to be reading. fun, critical content. There's a lot of like heavy, critical content out there. and I love something that's like fun and critical, so that'll get my[00:20:27] Nathan:Yeah. There are things wrong with the world and we could get depressed about them, but that doesn't[00:20:32] Jessica:Yeah,[00:20:34] Nathan:About fixing the things that are wrong with the world,[00:20:36] Jessica:yeah, exactly. Like turn it into a little bit of a, like the state of the world I feel is so bizarre.[00:20:43] Nathan:Right.[00:20:44] Jessica:Just so wild that we have set up the world the way we've set it up. Like everything that, that exists is just something that like some guy made up one day and we were like, okay, we're going to go along with it.And I feel like there is a lot of humor in that. so yeah, I, I love looking at the depressing state of the world for like a bit of a jokey lens. So if I find anything like that, I'm like immediate.[00:21:09] Nathan:Yeah, that makes sense. And I think that's where for anyone writing their content, like having that voice really matters. So it's not just, you know, this is what you're teaching or this is, the educational side. Or present the entertaining side. It's like, okay. But how can you, how are you gonna make me feel as I read and consume this.[00:21:29] Jessica:That's a great way to think about it. I think the difference, when I'm consuming like a newsletter versus the news is I don't really know. I don't concern myself with like tone or voice when I'm reading an article from like the New York times or the Washington post. but a newsletter is so much more personal.It's like you're getting into people's personal inbox, it's more of a one-on-one relationship. and I think it's a great opportunity to play with your voice in a way that you really sometimes can not when you're writing for a media plan.[00:22:04] Nathan:Yeah. So what are the things that you've done to practice that obviously you've had a whole career as a writer. And so, you know, as you've found your voice and the things that you play with, are there yeah. Little exercises or things that you play with or try on, or anything like that? Any, any tips for someone who's also looking to like craft their own way?[00:22:26] Jessica:It's as much of a tip, but I started writing as a songwriter. I went to school for songwriting. So I feel like a lot of my writing takes that into account. Like that's the musicality of something is very important to me. So I'll like read my own stuff out loud. Sometimes like flow of a sentence is very important to me, the rhythm of a sentence, the like intonation, the, Continence and assonance and all of that alliteration, I, I feel like when people can read something and there's a clear flow and rhythm to it, and the words like melt into each other sound nice next to each other.I personally feel like it locks them into the content early on. Like you want to keep reading because if you stop reading, it's like you're breaking this rhythm that you've started. So, yeah, I would say rhythm is very important to me and reading things out loud helps me make sure that what I've written is what I'd like envisioned and felt[00:23:35] Nathan:Yeah.[00:23:36] Jessica:Mind and my heart when I was conceptualizing the thing.[00:23:39] Nathan:Yeah, reading out loud is a really good tip because there's so many things where I'll find myself starting to read what I wrote and then like finishing it in a much more like in my head in a much more conversational way, and then realizing the sentences or the following sentences that I had. We're not conversational.They were like stilted. The version that I wanted to auto finish in my head is like, oh, that's better. Let's let's say that instead.[00:24:05] Jessica:I love that. And I think, I think newsletter subscribers are like ready for more. Conversational writing. Like I don't, I think you can be like professional and say something that has weight and has merit and has value and still be kind of, you know, casual about it.[00:24:23] Nathan:Yeah.[00:24:23] Jessica:As a strategy to connect with people.[00:24:26] Nathan:Is there a poster or a piece that you've written that you felt like. Maybe you struggled to find that balance of like, it was a, maybe a weighty piece or something like that. And you're like, oh, maybe this one I shouldn't be playful with or, you know, finding[00:24:41] Jessica:Yeah, there are definitely times when I take a break from the jokey conversationality I think the last big piece that I wrote, was about, anti-Asian racism when like all the news came out that like anti-Asian hate crimes were at an all time high. there's a lot of the beauty industry tends to take a lot of its concepts from Eastern culture, from Asian cultures.So, there was a lot to say there about racism within the beauty industry that, you know, happens in ways that you may not even realize. So for a piece like that, I think there were some moments of, of humor within it, like a dark humor within it, but for the most part, for, for things like that, I take that very seriously.I think my readers take that very seriously and I. It's less conversational then, because it's like, no, I have something that's like very important and clear that I want to get through to you. And I don't want it to be muddled with any sort of, uh jokingness.[00:25:46] Nathan:Yeah, that makes sense. So let's say you were a writing coach, coaching someone,Ryan newsletter, that sort of thing. You don't have to become a writing coach after this. Just.[00:25:59] Jessica:Thank God.[00:26:00] Nathan:But like, you know, you have a friend, maybe they're writing the newsletter, they've got a couple of thousand subscribers they're getting going in.And they're saying like, you know, they, they hear what you're talking about of the, the musicality and the, the flow of, of writing. And they're like, okay. Short of going to songwriting school, like, what's the, what, you know, is there, a book or another thing that you would recommend of where to start to, to sort of dive into the flow of what you write?[00:26:29] Jessica:There is a great essay, by Ursula K Le, is that how you say her last name?[00:26:37] Nathan:I'm not sure.[00:26:37] Jessica:Read it and I've never said it out loud before.[00:26:41] Nathan:Yep. I have so many things like that in my life where I'm like, I don't know how to pronounce this word.[00:26:46] Jessica:It's so embarrassing writing about skincare, because there are these huge, like long skincare ingredients that I write all the time. I can spell them for you off the top of my head, but then I tried to like say them out loud on a podcast, for example. And I'm like, I don't know how to say this at all. I'm looking for this, this essay it's from her book.No, no time to spare[00:27:10] Nathan:Okay.[00:27:10] Jessica:And there's this. And she writes a lot about right. but she has this beautiful essay about rhythm, and how it's different in poetry and how it's different in pros and how to kind of like sort out the rhythm of your piece. and I would say that was hugely helpful to me when I, when I first read it.So I would recommend doing that and. Yeah, I don't know. I use things like, I mean, I, I use it the sores all the time, but I use rhyme zone a lot for like fun phrasing and plays on words. It's just rhyme zone.com and you type in the word that you're you're playing with. And it'll kind of like, you know,[00:27:50] Nathan:Oh, interesting. Yeah.That's exactly the kind of, kind of that's good. Yeah. A lot of people, you know, they come to newsletters from kind of two different sides, either from the journalist, professional writer side or the, you know, hobbyist, maybe even, I never thought I'd be a writer, but I have this skill or something to teach or behind the scenes in this industry.And like writing maybe as a slog or a chore. And so it was always interesting when these two worlds meet and either, you know, one group might be really good at marketing because they knew they came from that world and another group.[00:28:27] Jessica:Yeah.[00:28:27] Nathan:Really good at writing and they each hate the other's job, but[00:28:31] Jessica:Yeah,[00:28:31] Nathan:Like they pick the job.That's the intersection of both of those worlds.[00:28:35] Jessica:Yeah, no, you're so right. I think there is this like sort of misconception in the journalism and reporting space that any reporter who is on sub stack has decided to go in all in on the newsletter. Because there have been some very high profile journalists who are no longer writing for like the times or the posts and they're just doing their newsletter.But I think for the large majority of, of reporters and journalists who have, who have started newsletters as well, it's like a both and kind of thing.[00:29:06] Nathan:Yeah.[00:29:06] Jessica:Sill freelancing and we have this, this sort of personal platform.[00:29:11] Nathan:Yeah. So how do you think about your career developing over the next couple of years? Is it, is there a specific milestone in mind, where you're trying to grow the newsletter to, to do that full-time or is it always trying to place a piece to the biggest possible audience?What's that like?[00:29:29] Jessica:Yeah, I would say my goal, like I very much, this is kind of earnest and nerdy, but like, I very much want to change the beauty industry. I see so much that is wrong with it and I see how it like emotionally impacts people. in terms of anxiety, depression, mental disorders, eating disorders, like there's a lot of heavy stuff that comes out of the beauty industry.And I like, I'm very passionate about actually measurably changing it. So for me, the number one thing is always, I want to reach the largest audience possible with an unadulterated message. So if I can do that in a place like the New York times, of course, I'd rather place it there than my own news. if I can do that through a book, of course, I'd rather write it in a book then in my own newsletter.So the newsletter has been sort of like a nice foundation for me to have and a nice fallback for me to have. And I, I truly love fostering it as its own little separate entity, but I would, I would say I almost try harder to place things elsewhere because I wantAs many people as possible to be able to, to read the things that I'm writing. the newsletter I'm I am writing my first book right now, and it's definitely been hard to juggle book writing with like reporting for other platforms and deadlines. So I will say like juggling a book and my own personal newsletter has been much easier than trying to juggle a book and reporting. So I think, I think there will be times in my writing career while I'll lean a little bit more heavily on the newsletter.And times where I'll lighten up on the newsletter. I'm always seeing it as sort of like a supplemental tool to my like greater mission.[00:31:13] Nathan:I think, I don't know what publication they were writing for. but someone was telling me about, was that in each of these publications, they're watching the view counts, you know, for every story. And they had gotten the newsletter. I think they were maybe at 20, 25,000 subscribers. And they would, when they placed a piece with a fairly major publication, they would email it out.And they, it was enough direct traffic to that individual piece that they could get it to move on. Some of these internally watched leaderboards and stuff like that. And so editors were paying attention to that of like, they didn't necessarily know like making things up that, you know, Jessica was the one who drove a bunch of traffic to this, but they're just like, wow, Jessica's stories are consistently resonating.And so they were wanting to pick up more pieces in that. and so I was always wondering about that, of how you can, it's not gaming an algorithm or anything like that.[00:32:08] Jessica:Hmm.[00:32:08] Nathan:Just saying like, look, here's my story. And I bring an audiences.[00:32:12] Jessica:Oh, I love that. I might try to do that. I always do. Like I do these little roundups every other week for my paid subscribers.And if I have something that comes out, I'll always put, drop the link in there, but I've never done like a strategized push like[00:32:28] Nathan:Right.[00:32:29] Jessica:Be interesting to experiment for sure.[00:32:31] Nathan:Well, cause it's like, if someone is following you that they're following you for. Your content and your ideas and your perspective. And they probably don't really care if it's, you know, in your sub stack, you know, on your Instagram or, you know,[00:32:48] Jessica:Right.[00:32:48] Nathan:Major publication, there's like, look, I want to read your, your content.And you're like, oh, today's article is[00:32:54] Jessica:Yeah.[00:32:55] Nathan:Here on Vogue. Or, you know,[00:32:57] Jessica:Kind of nice to hear, because I think that's something that I do worry about pretty often with my newsletter is I feel like a ton of my newsletter readership has come from social media. And so I'm like very conscious of cross posting. Like I don't, I don't want someone to get my newsletter and say, I already saw this on your Instagram, so I don't need to subscribe.I don't need another email in my inbox because I'm seeing it on Insta, you know? And I don't know if that's like a legitimate concern or how much people see when they subscribe to you on different platforms. but that has been. You know, something that I'm very mindful of, where if it's like a meme that I'm posting on social media, or just like a one-off Instagram post, I'm probably not going to repeat that content, even if I think it's good or important on the newsletter. Just because I don't know, I'm aware of like how precious it is to allow someone into your email inbox, because at least for me, like email is very annoying. The worst part of my day is trying to like go through my inbox and file it away into folders. And I never want my newsletter to be like, oh, I've seen this already. I've seen something very similar from her already.[00:34:09] Nathan:Right. Yeah. I don't know that I have a perspective on that. I'm just thinking about it. I don't have the same concern. but I don't know that. You know whether I should or not. I think probably my approach would be that if you've already seen something, let's say there's five or six things in the newsletter and I've already seen one of them on Instagram, but I just skipped past that one.[00:34:30] Jessica:Yeah.[00:34:31] Nathan:And so my focus would be on making sure that everything is high quality, more than making sure that everything is, completely a unique[00:34:40] Jessica:Yeah. That's I mean, that's encouraging to hear, and I think that that might, change how I approach my like every other week[00:34:49] Nathan:Yeah,[00:34:49] Jessica:Maybe I'll experiment and I'll see, I'll see if people are like, Hey,I saw that.[00:34:54] Nathan:The other thing that I would do is I would ask, one of my favorite things to do is to ask for replies to my newsletter, which has a downside of that you get a whole bunch of emails, but they can often be really fun cause they're, No, the people who are reading every day and like they're following your stuff.And, and so they're usually not pitching you things. They're just saying, like, here's the thing that I, and so in that case, just say, Hey, you know, if I share something on Instagram, would you also like it here? Or do you feel like, keep those worlds more separate? Like don't I want everything to be unique.And then I would just like, say hit reply and let me know.[00:35:34] Jessica:Yeah.[00:35:34] Nathan:And it's. Yeah, but you know, out of 9,000 subscribers, I'd bet you'd get at least, I dunno, 20, 30, 40 replies or something.[00:35:42] Jessica:Yeah, that's a good point. Okay. Oh, you're inspiring me. I have so many ideas now.[00:35:48] Nathan:Perfect. I love it. okay. One thing that I want to know more about is growing that. That newsletter from the pieces that you're, I assume subscribers are coming from Instagram. And then also from the pieces that you're publishing,[00:36:04] Jessica:Yeah.[00:36:04] Nathan:Seen like spikes? when it came from an Instagram post that did really well or some other promotion to drive subscribers,[00:36:13] Jessica:I mean, I definitely get new subscribers every time I post about it on Instagram or Instagram stories. So I would say that's been like a main driver for me, but my two biggest, like surges of subscribers came from, All of the newsletter press that's been happening lately. Cause you know, like the newsletter revolution is here.So, I got a little write up in New York magazine and then one in the UK Sunday style magazine and both of those were amazing and totally unexpected. I had no idea they were coming. so now I'm like, damn, how do I, how do I facilitate some more press for myself? Because this is where that.[00:36:55] Nathan:Like what would a spike like that look like? Cause that a couple of hundred subscribers, 500 a thousand from one of those[00:37:01] Jessica:I would say from New York magazine, it was probably close to a thousand. And then from the UK, Sunday times was probably between like 500, 600.[00:37:11] Nathan:Yeah. That that's substantial.[00:37:14] Jessica:Yeah. It was, it was really exciting. and it definitely goes to show like the power that these publications have. It's interesting to see that power as applied to like inherently, anti large publication platform, like a personal newsletter, you know?[00:37:35] Nathan:Yeah. So how do you, how do you think about it when it's like. More press would be nice. You're like, Hey, this, this is a big boost, you know? I'd 10% lift in total subscribers or something from a single thing. And then knowing what you know about journalism and being in the space, like, is that something that you craft a strategy around and say, okay, I'm going to intentionally pursue, placements in these publication.[00:38:02] Jessica:No, in terms of just the newsletter, I, I don't think I'll ever like strategize and try to do that. I think, I mean, the, the reason that I got those two placements is just because I. In the beauty space, my newsletter does offer something that's really different that you're not getting anywhere else. and so it becomes inherently interesting to write about or call out because this is the only place you can get that kind of thing if that's what you're looking for.So I think it's just more of like striving to figure out, like, how can I create more, very original content that actually. Gives value to the reader in a way that's going to create that kind of buzz. I don't want to like manufacture the buzz so much as I want. Like my condoms would be good enough for people to actually talk about it.But that being said, when my book comes out eventually like, hell yes, I plan to like strategize and try to get the shit written about me everywhere, which will hopefully we get to the newsletter as well. But yeah, I feel like I'm going to save all of that, like smarmy, you know, networking for book launch.[00:39:14] Nathan:Yeah, that makes sense to me. I want to push back on it a little bit, because so much of the success of the book is going to be dependent on a lot on a lot of things, but a big factor is going to be the size of your platform. When that book comes out.[00:39:29] Jessica:Yeah.[00:39:29] Nathan:And so if you wait to be self promotional until the book comes out, then like, that'll get this far, but let's say you were self promotional in a tasteful way.We're going to be tasteful about all of this. you know, but along the way, and that 9,000 subscribers turned into 25,000.Right. And it's that much bigger of a platform to launch from. So I'll say that with the caveat that I think the same thing.[00:39:51] Jessica:Yeah.[00:39:52] Nathan:We have, I've lots of friends who have big platforms and I'm like, oh, I could guest post on them.You know, with them, or like ask, Hey, can I come on your podcast or something like that? And I'm like 90% sure that they would say yes, but then I think, oh, I should save that for when my book comes out. Right.Cause you know, you have that, maybe that, just that one ask.So I think it's something that a lot of creators struggle with of like when to promote.And so intellectually I'm like promote early enough.[00:40:21] Jessica:Yeah.[00:40:22] Nathan:And then emotionally, what I'm actually doing is I think exactly what you're doing, but I'll save that for when I really need it.[00:40:28] Jessica:Yeah, I think for me, there's also this, this sort of inherent struggle with what I write about and getting press, because I am pretty critical of beauty media coverage. and I'm aware that I have made some enemies in the beauty media space. Like I'm not the most well-liked person, in some of these circles.So I do feel like I only have like a certain amount of rope that I can, use up like a certain amount of leeway in these spaces. and then also I, yeah, I don't know. I think it's something I have not sat down to really work out my feelings about. But there is some sort of ethical dilemma there where if I'm critiquing the way a certain platform has covered this beauty trend or whatever it is, I'm critiquing.And then I'm sort of like asking for press at the same time, like ethically, what does that say about me and my participation in these systems?You[00:41:30] Nathan:Right.[00:41:31] Jessica:Which is a big question and not one that I'm going to be able to answer here.[00:41:36] Nathan:Yeah. Are there publications outside of the beauty space that would have less of the, maybe sponsored ties or other, you know, issues[00:41:47] Jessica:Yeah,[00:41:48] Nathan:The main publications might have, but that would find your story.[00:41:52] Jessica:I think so. I think the path that I am trying to follow in beauty coverage right now. the path of sustainable fashion coverage, like I feel like fashion and beauty have been so intertwined in their coverage and they're, they're both sort of seen as these like less serious pursuits. They're both seen as like inherently female interests.And they've struggled to be taken seriously, I think. but with like the push towards sustainability content and, you know, the inevitability of climate change, I think. Sustainability and fashion is getting a ton of like serious quality coverage all over the place, even from platforms that wouldn't normally touch fashion.And I see beauty as being very behind that. Like there are still these huge global issues in the beauty industry and beauty production and just the way that we consume and beauty, that hasn't been touched. But I see it starting to be touched by these larger, serious. News organizations. And I feel like there's such an opportunity there.And that those are topics that I'm super passionate about and super interested in. So I'm, I'm trying to carve out a space for myself there to say, look, we're taking fashion seriously for the impact that it has culturally societaly environmentally. Like we have to start taking beauty justice seriously because it's just as big of a person.[00:43:17] Nathan:I like, I like that angle on that. That makes a lot of sense. And just seeing trends in a neighboring industry. I think you're right. I hope that I hope that you're right in, that plays out in there.[00:43:28] Jessica:Me too.[00:43:29] Nathan:One of the things that I'm curious about is kind of the rise of newsletters in the journalism space.I don't come from that world. I very much come from the newsletter world. And so seeing, you know, so many people either make the switch full-time, or get to the point where they're like, Hey, I've been writing these pieces everywhere. And like, my byline has just directed people back to Twitter or Instagram or.And now it's directing people back to my own audience. What are you seeing in like in your friends and colleagues and all of that is, are a lot of people starting newsletters or is there this overwhelming trend of some are starting it, and maybe it's getting hyped more than is actually happening.[00:44:12] Jessica:Yeah, I think that's what I've noticed. I don't think as many people within my like, sort of direct. Community of journalists and reporters are starting newsletters. And I think it's gotten so hyped. Like we're in such a moment of coverage right now that it almost like, seems like a little lame to start a newsletter now.Cause like everyone's doing.But the reality of the situation is that everyone is not doing it. And I think there's still a lot of opportunity and a lot of room to grow and to move into and to create your own kind of thing. like I mentioned, I think there is a big misconception that if you're starting your newsletter, that means you're done with journalism and you're just doing this now.It's like, no, you can very much do both. And you can do your newsletter once a month. You can do it, you know, once a week you can do it. However, often you have time for it. Like you said you could use it as a tool just to send out your journalism, pursuits to a wider audience. but yeah, I think sort of the hype around newsletters has sort of, created this little, Ooh, I don't know if I want to do a newsletter too.Cause I might get to see them. Like, I'm just doing what everybody else is doing.[00:45:23] Nathan:Right. Yeah. The, the newsletter hipster trend is sort of passed and it's gone mainstream. I can't do it[00:45:31] Jessica:Exactly. I mean, for the record, I don't believe that that's true, I think that's how people are perceiving.[00:45:38] Nathan:Well, it's so funny to me because, I've been doing E you know, email and email newsletters and that kind of thing since I guess, 2013. and you know, very excited. They got into all of that. And I was telling people like, email is amazing and friends that have me, who've been doing it since like 2001 were like, yeah, like good job, discovering it.Do you want to go and start? Like what a pat on the back, what are you hoping for here? And watching is, you know, these trends as they come, if you had a friend who, you know, is in the space who comes to you and says like, oh, I'm going to start a new. You know, what are the things, I don't know, the three or four things that you would tell them right away of here's what they should watch out for is strategies that they should employ any of those things.[00:46:25] Jessica:I mean, my number one piece of advice that seems really obvious. Isn't always is just to find your niche. Like I would say hone in on something as specific as you possibly can, within your space so that people have a reason to subscribe. I would say to have, like, especially if you're doing sub stack or a place where you can view past newsletters, like have a healthy backlog before you actually start soliciting people to sign up so that they can see what your content is like.And then this is a big thing that I think is missing from a lot of the journalism to newsletter side, because like he said, there are people who are coming from marketing and people who have never done marketing in their life. something that I do is that when I'm sending something out to my paid subscribers, I send a shorter version out of it to my free subscribers.Click to continue. And then it brings them to the paid subscriber thing. And I convert between 30 and 50 people every time.And when I sign up for free newsletters, which I sign up for a ton of them, I have never once got in that. I've never once gotten an email. That's like the intro of the article. And then it, you know, sort of leads me into that paid funnel.And I used to work in marketing. I used to work in fashion marketing. That was just like a no, duh of course I would do that sort of thing. but I've never seen any other like journalists to newsletter convert, use that very easy tool. so I would say, take advantage of that for sure.[00:48:07] Nathan:Yeah, that's interesting of the things that in one industry, like you're right in the marketing industry, everyone's like, obviously, you know, of course you would do that. And then you get into another space and it is this exciting, new thing. I started in, in design and, like user experience and interface design.And so I brought a lot of design ideas to marketing and then a lot of like direct response marketing ideas into the design world. And it needs to circle. Everyone was like, whoa, this is amazing and new.[00:48:35] Jessica:Yeah,[00:48:36] Nathan:You did it in the original circle, people are just like, obviously there's nothing novel about it.[00:48:41] Jessica:Exactly. I think people really, underestimate. The skills they learn on the way to get to where they've, they've gotten to. Like, I never would have thought the job that I hated in fashion marketing would have served me in, in, any way. Cause I sort of wanted to get away from all of that. Like marketing bullshit, lack of a better word, because at least at the company that I was at, it mostly felt like lying and just like squeezing money out of people.I think you can use those tools for good as well, which is what I'm trying to do.[00:49:15] Nathan:Yeah. So a lot of creators struggle with that transition where they feel like either from a past experience or something that they've seen where they're like, oh, I can never ask for money for this or charge for it or, that kind of thing. Or they're very, very hesitant to sell in any, anything. what would you say to them?Or what's your journey been like in saying like, no, this is what it costs. This is why you should subscribe.[00:49:40] Jessica:Yeah. I mean, I think it's important to have, to have a reason, you know, make it very clear that it's reader funded or user funded. for me, all of my content is very clear that I blame the media advertisement model for so much of the misinformation and bullshit that's out there in beauty. So me saying that my newsletter and this content is completely user funded, so that I'm loyal to you.The reader rather than an advertiser, is very like, you know, quote unquote on brand for me. And I think people who are interested in my content are more than happy to pay for it. It's solving a problem that I am pointing out in my reporting, you know? and then I would just say also like allow yourself to be surprised at how much people want to support you.I have been so pleasantly surprised by people who are just, they just liked my content and they're happy to pay for it. And I think one of the, the biggest, the biggest ways that I've seen that happen is that, on substance. They let you do like the page, so you can do monthly or a yearly rate, or you can do something called a founding member, which is just somebody who pays a little bit more to support and they don't really get any extra benefits at all.And I am shocked at the amount of people who give me 50 more dollars than they need to, just to support, And that's like, every time I get that email, that's like someone signed up for the founding member level. It's heartwarming because it's like, there are a lot of people out there who want to support great creator, led content.[00:51:23] Nathan:Do you have a percentage or numbers on that? Like I'm curious, every time I see that I'm like how many people select that[00:51:29] Jessica:Yeah.[00:51:29] Nathan:Know from doing multiple prices or packages, that it's one of the best ways to increase revenue is to just have a higher price option available.[00:51:38] Jessica:Yeah.[00:51:38] Nathan:confirming that, but I want to know any[00:51:40] Jessica:Yeah. I have not like crunched the numbers on anything, but just from, so I sent out a paid newsletter, on Thursday. So between Thursday and today from like my conversions of free[00:51:55] Nathan:Yep.[00:51:56] Jessica:Sign up, I've gotten, I think 56, new signups. I would say maybe 10 of them were the yearly membership and maybe five of them were the founding member.[00:52:08] Nathan:Okay. Wow. So half of the year, the ones being the like yeah. I'll pay you $50 more just to support your work. Even[00:52:17] Jessica:Yeah,[00:52:18] Nathan:Because the yearly membership is supporting your work, but even just[00:52:21] Jessica:Yeah,[00:52:21] Nathan:Above and beyond.[00:52:23] Jessica:Yeah, exactly. I mean, that's just what, roughly, from what I remember from the email. I'm not like super concerned with, with stats and strategizing right now. I'm just like ecstatic. Every time I get the ding on my phone that says somebody new signed up.[00:52:39] Nathan:Yeah. That's super fun. So, what are the things that you're thinking about next for the newsletter? Is it slow, steady, growth, and maintaining that while working on the book? Is there a big milestone that you're working towards any of those things?[00:52:52] Jessica:There is not a huge milestone, but I think when I first started it, and this is, I think maybe just a personal hangup, but I was very conscious of not bothering people too much, like not being in their inbox constantly. So, it was like one big story a month, and then every other week for paid. Now I'm toying with the idea of doing more, short form content and where weekly content.I'm going to be launching a new feature for paid subscribers that's gonna be, like an advice column, but more like, how do I navigate the industry? How do I divest from these marketing tactics? How do I like stay smart and know what's alive and what's not?So, I'm going to be launching that within the next month.Then, for everybody, I'm going to be launching weekly or even twice a week, just like little, like a little tip newsletter. Because what I do in my newsletter a lot is critique the beauty, and point out what's wrong with it.People are always like, okay, sure, but how do I apply that to my own life? Like how do I get over the fact that I know it's marketing, that I don't need to have big lips to be beautiful, but how do I stop feeling that way?So, it's going to be more practical tips for, I guess, sort of healing from all of the beauty industry shit that they put us through, but it's going to be very short, quick hits, like, you know, five sentences, a paragraph tops. So, I'm going to experiment with a couple of different, forms of writing and a couple of different frequencies and see, see what people.[00:54:38] Nathan:Yeah, that sounds good. Well, if anyone wants to go subscribe to that and follow you on Instagram and other things around the web, where should they go?[00:54:46] Jessica:My sub stack is JessicaDefino.substack.com, and you can sign up for The Unpublishable there. And then on Instagram, I'm @JessicaDeFino_.[00:54:56] Nathan:Sounds good. Well, thanks so much for coming on. This has been fun to[00:54:59] Jessica:Yeah.[00:54:59] Nathan:learn about a whole side of the newsletter industry that I'm less familiar with, and just hear your story, and your writing tips, and everything else.[00:55:08] Jessica:Yeah, thank you so much. I feel inspired. I'm going to go send more newsletters.[00:55:13] Nathan:Sounds good.

Ali Abdaal is a Doctor, writer, podcaster, entrepreneur, and YouTube sensation. Ali has grown his YouTube subscriber base to over 2 million, and writes a weekly newsletter titled Sunday Snippets. Sunday Snippets covers productivity tips, practical life advice, and the best insights from across the web.Ali studied medicine at Cambridge University. He worked as a Doctor in the United Kingdom before taking time off to explore his other interests. His YouTube channel covers medicine, tech, lifestyle, and productivity. Ali also co-hosts a weekly podcast with his brother, called Not Overthinking.After learning to code at age 12, Ali started doing freelance web design and development. He enjoys playing piano, guitar, and singing covers of mainstream pop songs. You can find occasional videos of Ali's music prowess on his Instagram page.In this episode, you'll learn: Ali's savvy insights for growing your YouTube subscriber base A proven formula for writing content titles that get clicks Ali's playbook for taking your podcast to a whole new level Links & Resources The Nathan Barry Show on Apple Podcasts The Nathan Barry Show on Spotify Sean McCabe Pat Flynn ConvertKit Ibz Mo Casey Neistat Sara Dietschy Chris Guillebeau Tim Ferriss Derek Sivers School of Greatness podcast Lewis Howes Dave Ramsey Michael Hyatt Cal Newport Crash Course John Green Hank Green Daily Content Machine Andrew D. Huberman Reboot Dan Putt Tiago Forte David Perell Jim Collins The Flywheel Effect Impact Theory podcast The Tim Ferriss show Seth Godin Scrivener James Clear Ali Abdaal's Links Follow Ali on Twitter Watch Ali on YouTube Check out Ali on Instagram Ali's newsletter Ali's website Episode Transcript[00:00:00] Ali:YouTube can change your life, but you have to put out a video every single week for the next two years. If you do that, I guarantee you it'll change your life. I can't put any numbers on it. I can't tell you how many subscribers you'll have, or how much revenue you have, like a hundred percent guarantee.You will change your life at the very least in terms of skills or connections or friends, or opportunities that will come your way as a result of posting consistently.[00:00:30] Nathan:In this episode, I talk to Ali Abdaal. Over the last four and a half years he's built his YouTube channel from zero to 2 million subscribers.He's who all of my friends who are into YouTube turn to for advice. He's got a paid course. He's got a substantial email newsletter. He started out as a doctor and then has made the switch into a full-time YouTuber. So anyway, I'll get out of the way, but, before we dive into the show, if you could do me a favor after the show: if you could go and subscribe on Spotify, iTunes, wherever you listen.That helps with downloads. If you could also write a review, I really appreciate it.Now it's on to the show, with Ali.Ali, welcome to the show.[00:01:17] Ali:Thanks for having me. This is really cool. I've been following you on the internet in a non-weird way since 2016. I remember once in, I think it was 2018, I discovered your 2015 podcast series all about launching an ebook, and pricing plans, and all this stuff.It was so good. Now we're looking to do eBooks and things like that. Thank you for all the inspiration on that front.[00:01:46] Nathan:Yeah, for sure. Well, it's fun to have you on, it's been fun to watch you grow. I was actually on a hike with our mutual friend, Sean McCabe after he moved to Boise, my hometown. He was talking about you, and I hadn't come across your stuff yet. And I was like, oh, I gotta check it out.And now I'm watching a whole bunch of videos. And then of course we've been internet friends for, for awhile now.[00:02:08] Ali:I'm now a customer of ConvertKit as well, for the last few months.[00:02:11] Nathan:Yeah. Let's see. Okay. So I want to dive into your story and get some context because you have an interesting path of finishing school, like a substantial amount of schooling, and then diving into the world of being a doctor, and then transitioning out of it.What was the plan? Let's start.[00:02:36] Ali:Yeah. for a bit of context, I spent six years in medical school, and then two years working full-time as a doctor in the UK national health service before deciding to take a break. In that break I intended to travel the world, but then the pandemic happened and I ended up becoming a full-time creator on the internet by virtue of the fact that I didn't have a job when it was a pandemic.When I first decided to apply to med school, I'd been into the whole entrepreneurship thing since the age of 12. I learned to code. I started doing freelance web design and freelance web developer from age 13 onwards. So, in school, in high school, middle school, like we call it secondary school in the UK, I'd rush back home from school when I finished off my homework in record time, and then just be plugging away at like PHP or some HTML or some like jenky Java script. I used to make $5 here and there, and be like, yes, I'm, I'm making magical internet money. Every year when, when I was in, in high school, my friends and I would come up with a new business idea.So, we started this multi-level marketing thing and some other random pyramid schemes, and random paid surveys, and whatever we could do to make money circa 2006 to 2010. So, I always had this interest in entrepreneurship, but then when it came to figuring out what to do with my life, I was getting decent grades in school and because I'm Asian, and everyone in the UK who is Asian, their parents are doctors. So, it was like a default path for me to just like, oh, you know, why, why don't I become a doctor? And I kind of reasoned at the time that if I could be a doctor, and also be a coder on the side, that's like a more interesting combination than if I were just a coder or just a doctor.Not that there's anything wrong with either, but I felt the combination would be more interesting because of the synergy. And so I ended up going to med school, which is a weird, a weird reason for going to,[00:04:24] Nathan:Interesting to him, interesting to you, or interesting to[00:04:27] Ali:Yeah.[00:04:28] Nathan:Family friends.[00:04:30] Ali:Oh no, not family and friends, interesting to me, because it would make life more fun and interesting to me because it unlocks opportunities for creating a tech startup or whatever, further down the line. I think at the time I was drinking the zero to one Kool-Aid[00:04:45] Nathan:Well, Peter Thiel[00:04:46] Ali:Yeah, like that, where I first came across the idea that like, innovation happens at the intersection of multiple fields.And so, you know, the printing press was invented by the guy who really understood, I dunno, looms and how spinning yarn worked, but also understood like something else about something else, and combined these ideas to create something cool. So, I always found it in my head that, Hey, why don't I get really good at the medical stuff and be a really good doctor?And then on the side, if I know how to code, then I can like combine those to spin off some, fit some something interesting further down the line.[00:05:14] Nathan:I think that resonates with me of like,I think that people, especially like online creators who go and do one thing very specifically, maybe don't have as much of an interesting angle, to put into it. Like I think that some of what made me more interested.This is like, they're just hypothesizing, teaching like online business and, and marketing is having a design background, even though those are much more overlapping than say, like a big a doctor and, and, you know, a web developer, you know, as you were starting into it. But, but I think having those skills in another area makes you more interesting as a person and it gives you better stories to tell, and then it gives you a better perspective.And you're not like just pulling from the same industry over and over again.[00:05:58] Ali:Yeah, no, exactly. I, I often find that the, the YouTubers that I seem to kind of, and the, and the, and the bloggers as well, who I follow more of are the ones who seem to have multiple interests. And it kind of gets to that question of like, you know, the, the thing that holds everyone back around, like, what's my niche, like, oh, but I have to pick one thing and get really good at that.And yes, that does have some merit to it, but I often also think that, yeah, but you know, how, how can you carve out a niche for yourself? That's a combination of the other, other stuff that you're interested in, And so instead of trying to be the best, I don't know, productivity YouTuber, it's like, you're the only productivity YouTuber.Who's also a doctor who also runs a business that that's kind of how I think about it.[00:06:37] Nathan:Yeah, that makes sense. Okay. So, when you're in med school, when you started your YouTube channel or you're wrapping up med school, right.[00:06:45] Ali:That's right. Yeah. So, I started the YouTube channel in my penultimate year, so I, I, I, I done five years of med school at this point. I'd set up a few businesses. I had like two SAS products that I was using to side hustle, income, most my, my way through med school. And then in 2017, when I was in my final year, the YouTube channel actually started out as a content marketing strategy for my, my business, that business was helping other people get into med school.It was like that standard thing. Once you do something, you then teach other people how to do the thing. and it was like, you know, the creative economy before it was really called that where[00:07:20] Nathan:Yeah,[00:07:20] Ali:You kind of follow that model. And so the YouTube channel started.[00:07:23] Nathan:Because you were you teaching people like test prep[00:07:25] Ali:Exactly. Yeah. And it's so similar to pet Flynn story as well.You know, he, he started off teaching people how to do some architecture exam. I started up teaching people how to do the med school admissions exams, and that's kind of transitioned into a coaching business, which then transitioned into the YouTube channel.[00:07:40] Nathan:Okay. And so as the YouTube channel started to grow, like, what were some of those first milestones, you know, as you're getting to, how long did it take for you to a thousand subscribers and then maybe, you know, 5,000 or 10,000? Like what milestones stand out.[00:07:52] Ali:Yeah, so I started in the summer of 2017 and it took me six months and 52 videos to get to the first thousand subscribers, six months in 52 videos. I was putting out two videos every week while preparing for med school finals and kind of neglecting my exams for the sake of YouTube, because I could see the YouTube thing was like, oh, I really want to do this.I think the ROI on being a YouTube or is going to be higher than the ROI and getting an extra 2% in my med school finals. that was, that was the theory. Anyway, So, yeah, it took six months of the channel to get a thousand subscribers, another like four or five months for it to get up to 5,000 subscribers.And at the point where I was at around 4,005,000 subscribers, there were two like really good things that happened. Number one was a collab with a much bigger utuber. his name is Ibz Mo. So he and I got to know each other through university and he had 60 K at the time. And so he and I did a collab which took off and helped the channel get exposure.But also there was a video that I made my, my very first video that actually went viral, which was a video about how to study for exams. now this video is a bit weird because like I'd actually planned for it to happen like a whole year before I made it. So when I started YouTube, I, I sort of consumed the hell out of everything on the internet, around how to be a YouTuber and, Sara Dietschy and Casey Neistat had this thing whereby Casey Neistat, enormous YouTuber, Sarah DG would take YouTube who was smaller at the time.She went from 40 cases. Over to like one through over a hundred, a hundred thousand, basically overnight because Casey Neistat shouted her out. and the way that she described that, and I, that I found in some random interview, like on the YouTube grapevine, was that you, you benefit from a collaboration with a bigger utuber, but you only benefit from it.If there is already a backlog of really high quality content on your channel. And so I took that to heart and I knew that, okay, at some point I want to do a collab with a bigger utuber. And at some point I want to try and make specifically a video on how to study for exams, but I knew number one, I needed to have a backlog of hot, cold, high quality content because otherwise no one would care.And secondly, I knew that it would take me about a hundred videos to get good enough at making videos to actually be able to make a decent video about exams. And so that was like my 82nd or something video, which I, I, I I'd had in the back of my mind for so long since, because since getting started button, you know, I need to get my skills up.I need to put in the quantity so that I can actually make videos that are hopefully.[00:10:06] Nathan:Okay. That's interesting. Yeah, because coming, doing a collab and coming to a channel and it's like, okay, they have four videos. And the one that I saw in the collab is actually the best one they've ever done. Like it's sort of, it doesn't have the same ring to it as if you come in and be like, wow, this is incredible.Like, one of my favorite bloggers, you know, it's separate from the YouTube space, but I got him, Chris Guillebeau was an author and blogger and I followed him in the early days. And I had the experience of, he had written a guest post for Tim Ferris and I was reading Tim versus blogging. This was probably 2011, maybe.And I was like, oh, this is really good. I love it. I think it was on actually on travel, hacking, you know, credit card points and all of that. And so I clicked over to his site and I think. Over the next, like two days, I just read the entire website, you know, Nate, it was like years worth of blog posts and all that, but that was the experience.Right. The guest posts is a collab of some kind and then coming over and you're like, you're just deep dive and consume everything rather than the experience of coming over and be like, oh, okay. That's interesting. You know, and like moving along and the back catalog is what, what, drives that?[00:11:09] Ali:Yeah. Yeah. I had, I had that exact experience with Derek Sivers who I discovered through the Tim Ferriss show and Mr. Money mustache, but it's coming through a temporary. I was like, all right, I'm spending the next week of my life. Just binge reading all of your blog posts that you've ever written for the last 20 years.And now it's like, I've got this information downloaded into my brain.[00:11:24] Nathan:Yeah. I love it. Okay. So one thing that I wondered about is as you spend all this time, you know, on med school and, and then, you know, becoming a doctor, it's a big investment. then you also have this love for YouTube and the channels growing. Like the channel now has 2 million subscribers and, and, this is wild success.How do you think about. Like when you made that switch to YouTube, as your full-time thing and leaving behind, at least for now your career as a doctor, how did you make that decision? How did sunk cost play into it? You know, all that,[00:11:59] Ali:Yeah. So this is, it's still something I think about to this day. It's like, there's this balance between how much do I want to be a doctor? And how much do I want to be a YouTuber? when I made the decision at the time, it was, so it was about actually this time, last year, where I took a break from medicine intending to travel the world, but then pandemic happened and ended up being a full-time YouTuber.And then like back then, what I was thinking was I'm, I'm only going to do this for a little while. Cause this YouTube thing is going well right now, the problem with YouTube and like the creative stuff in general is that there's not a lot of like longevity to it necessarily. Like there are so few YouTubers who are big today that were also big 10 years ago.And so that's the thing that I constantly keeps me up at night. Like how will I continue to stay relevant? You know, X number of years from now. And to me, the medicine thing always seemed like a great, you know, my main hustle is being a doctor and my side hustle is being a YouTuber so that no matter what happens, you know, at least I'll have a, a full back career to kind of fall back on.[00:12:53] Nathan:Pretty sure doctors have irrelevant 10 years now.[00:12:55] Ali:Yeah, I'm pretty sure doctors will be relevant. So I wouldn't, I wouldn't have to worry in that context. in the UK, the way the medical system works, there's also like, after you're a doctor for two years, at that point, there's a very natural gap and a lot of people will take some time out to, to go traveling or whatever.And just so happened that COVID happened to that exact point just as I just, as I left to take a break. But I was, I was on the, the school of greatness podcast with Louis hose, last, last week. And he, he was calling me out on this. He was saying that basically I was bullshitting myself because I think the reason why I was holding onto the medicine thing was a profound sense of risk aversion.It was number one. The what if I, what if I lose everything at least then I'll still be able to be a doctor. And number two, it was a case of like, oh, but. I, you know, my brand was built up of the back of being a doctor. And if I lose that, then you know, who am I, why does anyone listen to what I have to say?Who will care what I have to think anymore? Because now I'm just a YouTuber rather than a doctor, which has like prestige and it has like clout. And he basically just called me out and dismantled, like all of my BS on all of those funds. And that really, really got me thinking. Cause like, you know, ultimately the thing that I care about is teaching and inspiring people.And if I think about, if I could only do one thing for the rest of my life, it would not be saving lives as a doctor. It would be teaching people. And that's the thing that YouTube lets you do and lets you do it at scale. And that's the thing, the internet that today. And so now right now I'm going through this phase of having to really think about like, am I only holding onto the doctor thing because of because of fear. And am I holding onto fear and sunk costs, which is obviously like a stupid thing. do I really want to go all in, on the YouTube stuff and then the business stuff, because my real passion is teaching. I don't know any, any thoughts on that balancing, like the fear and like the sensible decision would like following your passion.And it sounds so cliche, but yeah.[00:14:48] Nathan:Yeah. No, it all makes sense to me. The place that I would go is, you know, as you, cause there's, there's fear on both sides, right? I've given up the, being a doctor and then there's fear of what does this career as a, as a creator, as a YouTuber look like in five years, in 10 years. And I would lean in on that side and try to figure that out.Like who are the people, questions I would ask, who are the people who. You admire, who have had longevity in their careers. Right. Cause in the, in the blogging world that I've been a part of the last I want to spend, I guess, almost exactly 10 years now. There's a lot of people who are not around anymore, you know, like they're still alive.I'm sure they're living wonderful lives, but they don't live internet, you know, internet visible lives anymore. and then also seeing like what, what does your business look like in that? It's how you do dependent? Is it, what does that look like? So as you look five years ahead, this something I want to ask later, but, but I'm curious for now, like five years, 10 years ahead, like what are you doing?What's the, what does your, your audience look like? And what role does YouTube or other things play in[00:15:50] Ali:Yeah. Yeah. I think if, if, if I think about people who have longevity, I think you're one of the examples that comes to mind where you started off as a blogger, and then you did the ebook thing, and then you went into the SAS thing, which is now like, absolutely like, you know, exploded. so that's really cool.The other people who I look to are, you know, people like Tim Ferris, who. Has gotten bigger every year, since before I work, we came out and it wasn't a one hit wonder. We started off with the books and then he did a great job of transitioning into the podcast where now it's less about him and more about kind of spotlighting other people and building this almost the institution of his, his personal brand, which is built off of teaching people.Cool, cool things. yeah, I think about it, like in that context, like the thing that you and Tim have in common is that you've both gone, moved away from being very personal brand heavy and more towards being somewhat institutionalized in your case and convert kit in his case, through his podcast.And that's kind of how I see it for myself in a dream world, whereby let's say five years from now, I'm still like doing YouTube videos and teaching people and I'm learning things. And then teaching people, the things that I've been learning. Cause I, I enjoy that kind of stuff, but it's become, becomes less about me personally and more about kind of showcasing other experts.Building a team and building a brand that can be dissociated from my personal name, if need be.[00:17:09] Nathan:Is there a blueprint that comes to mind? So I think about this, a lot of where, where this goes with the highest leverage point to direct an audience to, I —-wrote an article called the billion Abdaalar creator, that is about like this exactly of, you know, if you have an audience of 10,000 or a hundred thousand or a million people, like, what is the thing that you would point that to long-term.And so I'm always looking for these blueprints that other people have created, right? Like I think, Dave Ramsey would be an example of someone who has taken this.Podcasting a radio show is basically a podcast. you know, and taking it to this extreme of, I don't know what they have, I'm making up numbers, but in the ballpark of like 500 to a thousand employees, they've got like this franchise thing, they've got courses that they're, you know, you can sign up for everywhere.Like it's this massive media empire that I can draw a pretty consistent line from, you know, blogger with 10,000 subscribers or 10,000 podcast downloads consistently to that of like continually working away at it. Not to guarantee you that, that you'll hit that, but you know, there'll be other people on Michael Hyatt or, anything else or there's the software direction that I went.So are there like specific blueprints that you look at and be like, okay, that, but[00:18:30] Ali:Yeah.[00:18:31] Nathan:Of it.[00:18:32] Ali:Yeah. I think for me, the playbook that I'm currently following is trying to be a cross between Tim Ferris and Cal Newport.In that Tim, Tim Ferriss in the context of starting a podcast, interviewing experts on stuff. And I need me to, I probably add someone to that. Tim Ferriss, Cal Newport, and the crash course, the YouTube channel, which is run by Hank and John Green, whereas also taking the Tim Ferriss model of podcast, interviewing other people.And then, then that becomes its own kind of content, which helps people, the Cal Newport model of actually I think he he's done a great job of straddling the two worlds of old world prestige of being a professor at Stanford or wherever he's a professor at a part-time and also being a part-time writer and blogger and internet personality type person.And then like taking elements of those and combining it with like the YouTube airy type thing, whereby I think, I think what's missing from the world of podcasts these days is that there are so many podcasts and there is so much incredible wisdom, which back in the day used to be locked up inside either textbooks or in scientific journals.Now, the people who write those scientific journal review papers are being interviewed on all the podcasts. but they're being interviewed in the context of a three hour long discussion. And yes, you could listen to the three hour long discussion. Yes. You could listen to the podcast clips that they've got, that they've been posting through Daily Content Machine on Twitter or whatever, but it's just not as actionable as someone actually creating a compelling YouTube video.So, you know, you could listen to Andrew Huberman interview, the world's expert on longevity about all the eight different things you should do to increase your life. And very few people would follow that advice because there's no in a digestible format. And so if I'm thinking like what I'm, what I'm thinking is that if we can do the podcast thing, we can do the kind of Cal Newport thing of combining old world prestige with new world, kind of content, and also do it in the format of like YouTube videos that are accessible to the mass market and, you know, a lay person audience that is kind of the combination that I see myself doing over the next like five years.And that feels quite exciting.[00:20:32] Nathan:Yeah. So that target of like the 10 to 15 minute YouTube video, that's really well crafted and architected to have the table of contents and even skip to the sections. And it's like, look, this is what you need. And it's not just what was covered in an hour long interview, but also like, and then we pulled in this and when they referenced this thing, like, this is what they're talking about.We can illustrate it with visuals and everything else.[00:20:55] Ali:Absolutely. Yeah. And that's the thing that I'm hooked. So in the process of building a team around, which is something I wanted to talk to you about because you've built a big team over time, I was speaking to Derek, you're a director of marketing as well about building a team and he had, so he had loads of advice to share.So that's, that's a challenge for me right now. It's like, you know, two years ago, it was just me last year, this time, last year, there were three, three of us full-time well, two full-time. It was me working as a doctor and a part-time assistant, and now there's 12 of us, but now we're hiring another 10 people.So by next month it's going to be maybe like 20, 20 of us a hundred. It's all those problems associated with scaling a team and leadership and management. And that's the kind of stuff that, I've been really as sort of very much on the steep learning curve of, and that I'm very excited about getting better at,[00:21:44] Nathan:Yeah. what's the reason that you're growing the team so quickly.[00:21:48] Ali:Well, let's see, because we just have a lot of money. once, once we launched our, yeah, it's a, it's a, it's a good problem to have. We're just like very cash rich and expertise poor as someone described as, We launched our cohort based course part time, YouTube academy this time, last year, it did phenomenally well, I'd been doing classes on Skillshare, which started off as making like a few hundred to a few thousand a month and is now compounded to the point where we make some way between 60 and $80,000 every month, just passive income of Skillshare classes.That means that every month we're just making more and more money. And I see the, I see the numbers going up and I see them go up and I, I see basically like, well, why, why are, why aren't we doing anything with that money other than just[00:22:30] Nathan:Right.[00:22:31] Ali:every year.[00:22:32] Nathan:Okay. So really quick, since you mentioned, are you okay sharing some of the numbers, like the numbers from part-time YouTube academy?[00:22:38] Ali:Yeah. so we launched the first cohort in November last year. I think this year we're on track to do maybe like $2 million revenue and like 1.1 0.5 million profit, 1.6 million profits, something like that. next year we're hoping to take that up to like 5 million revenue. Which again, all of these feel like, like dumb numbers, I'm just plucking out of thin air.Cause it's like, I I've, I'm, I'm really bad at like projecting, protecting financials. Like it's all, it's all just a guess. Anyway, like if we could do four cohorts and sell 600 places, that would be 5.5 0.1 million revenue. It's like, that's actually, that's actually doable, but it's just such a fricking ridiculous numbers.It's like, how on earth can that be doable? It's just like, how, how does it even work?[00:23:23] Nathan:Yeah. Welcome to the internet. And, when you have substantial leverage, like things that were possible, like seemed insane before you're like, oh yeah, I know that math checks out, you know?[00:23:34] Ali:Yeah, exactly. I suppose if somebody, to you for ConvertKit was I think last I checked, you were on 20 million annual recurring.[00:23:41] Nathan:Yeah. We're at 20, 28 and a half. Now[00:23:44] Ali:Well the hell that's going to quickly compounding.[00:23:48] Nathan:The magic of compounding, This is fascinating to me because a lot of, I feel like a lot of content creators are, you know, get to your stage and they're like, okay, what, you know, what Lamborghini should I buy right now?Have you thought about putting the line beginning in your YouTube videos? I'm kidding, please.Don't[00:24:05] Ali:I mean, I've got a Tesla model three, so that was my, a splurge.[00:24:08] Nathan:That was your splurge. Yeah, exactly. you know, so interesting to me that you're hiring at the rate that you are, which is to be totally clear is the rate that we hired at ConvertKit like slow at first of like two or three, four, and then it started to, like started to really take off. And I think in, let me think how long eight months we went from four people to 21 people.And, and that worked really well for us. And we were growing really, really quickly. And, and, like in that time, I think we 10 X revenue, like going. 30,000 a month in revenue to 300,000 a month and revenue. and so that that's absolutely a wild ride. And then we kind of paused there for a second and we like methodically about, okay, what are the roles that we need?How do we build the team culture within the group that we have? How can we invest in those relationships? We also had our first team, like in-person team retreat at that time. and so I think it's really important as you grow a team that quickly to make sure you're really, really, yeah. Intentional about, the team culture, which like, that's one of the things like, what does that even mean?How do you, how do you do that? And the way that I do it is being clear about the mission of what you're building and why. and then investing deeply in the relationships with each person.[00:25:32] Ali:Okay. And what does, what does that mean?[00:25:34] Nathan:Was, so you're hiring all these people, right? And let's say you're hiring from you're very much the face of the.And so if someone's applying to like, oh, I want to work with Ali, right? Like, let's do that. And so they have this relationship with you and what you don't want is this, you'd end up with this hub and spoke model where you're the hub and everyone has a relationship with you and they don't have it with each other.And that's just the, it's a natural way that things are joining, right. Or the way it comes about. I, the same thing when people wanted to start working at ConvertKit, they wanted to work at convergent, but they a lot wanted to work with me. And so you have to invest deeply in turning that hub and spoke into like a spiderwebs where if you're not at the core of it, they all are riffing on ideas.They, you know, understand each other's, families and like individual values and everything else. and that matters more. And so you have to know that the natural state of things is not ideal and you need to like aggressively work, to change that. So that you're less important than your own.[00:26:39] Ali:Oh, interesting. Yeah. That's exactly the challenge that we're having right now where. Still all of the things kind of flow through me, but it's, I think over the last few months, as I've gotten like business coaches and working with, with our mutual friend, Sean, as a coach, as well, and reading sort of dozens of books about like leadership and management and like org chart structure and all that jazz, we're starting to get to a point where I actually do feel like stuff is happening without me.And it's like the best feeling in the world when they're just doing stuff. And I'm like, whoa, wow. That's actually a great idea. It was so well done. And you've actually done this better, better than I would have done this. Whoa. Okay. This is really cool. so hopefully as the team expands, yeah, the, the, the culture thing is interesting.I think so far, I haven't given any thought to culture in the slightest as just sort of happened organically slash accidentally. but one of the exercises that Sean, Sean took me through was the thing of like, imagine, you know, a year from now or three years from now, what is the sort of business that you want to have?Like you go into work in the morning, like what, what do you want to say. It was only after that. I kind of thought about that, that I realized that for me, what that dream looks like, it's actually having an in-person team having like a studio, maybe, maybe in a place like London that we can invite people over to for podcasts and focus for collabs having an in-person team.Or maybe once a once a week, I have brainstorm meetings with, you know, our writers and researchers and stuff, and we figure out what we're doing. Maybe once a week, I filmed stuff for the YouTube channels. And maybe once a week, I sit down to record a podcast with someone cool. And the rest of the time I spend like chilling, or, you know, writing or reading or doing other, working on the businessy type stuff.And we have like a COO or general manager or whatever you want to call it, who runs the day-to-day operations without needing my input. and it was only really when I kind of said that out loud, I'm just going to ask, so, okay, well when you just make that happen and I was like, oh yeah, you're right.I could just make that happen. And then, because I think before I just, I, I drank the remote work Kool-Aid so, so much that I just sort of assumed that you had to hire remotely. Then I realized, hang on, given that this is the sort of business I want to be in where we're all actually in person, because it's more fun.I can just hire people who are only London. And so when we're not doing that, hiring people who are only in London, which feels weird, but it means we also have, you know, a few dozen applications rather than a few thousand to, to deal with, which is, which is kinda nice.[00:28:59] Nathan:Yeah. And that's something that when you get clear on that, and that's why so many people want, besides journaling or whatever, other journaling coaching, any, any form of getting that clarity, it's you realize that you're like following this meandering path and like, and then we can do this and then that, and then you realize like, oh, I can just draw a straight line from point a to point B and just do that now.And it's, it's so powerful and you'll save yourself a lot of trouble because then you won't be at a point, right. Where you say we've built a 25 person team. That's like, maybe there's six in London. And then, everyone else is spread throughout the world and people are loving aspects of that, but then they're feeling like the people in London are getting more time with you and right.And you go and create this major culture problems because you had an intention like, or an internal desire that you never expressed, explicitly. And then once you express that and then everyone's like, oh, okay. So I know that it's them working for you remotely right now. I know that I either long-term need to switch to being a contractor of like, just providing a service, you know, or I need to move to London or I need to fully transition out.Like, and there's like a beautiful clarity in that, that when you just keep it inside, you like no one will, no one will experience.[00:30:17] Ali:Hmm. Have you, have you got any like prompts that you find helpful in this sort of journaling thing and figuring out what you want from the business and from life?[00:30:25] Nathan:So, you and I both share a passion for coaching and I hire a coach as well as name's Dan, from an organization called reboot. so he asks all kinds of questions. one, I was navigating a scenario recently that was just really frustrating. And, he said, okay, I want you to picture when you're 40.So I'm 31 right now. So nine years from now, how would your 40 year old self looking back, you know, basically 10 years be proud of how the situation was handled. And that was a version. So basically the prompt would be like stepping forward, not just, what do you want 10 years from now, but like stepping forward and trying to really imagine that scenario.You know, what's pushing you to do, and then looking like looking back on it as a memory of how you handle this next period of difficult transition or any of that. So that'd be one version. Another is like really pushing on like the five why's and really digging in of why do you want that thing? What do you, what are you actually trying to accomplish?I'm sure there's more, butYeah. Are there others that you use.[00:31:38] Ali:Yeah, that question of why did I come across this? I can't remember where I was like to cite my sources, but, the thing of when, when making a decision, think about what decision your like 10 year older self would have wanted you to make, to be like the best version of yourself.And I've been thinking about that recently in the context of this thing of do I go all in on the YouTube thing or do I just kind of do Hoff medicine off YouTube? And I do think out of 10 years from now, I would have wanted myself to make the decision of actually just going all in on the passion project and just seeing what happens with that.If it doesn't work, it didn't work, but at least having a go rather than feeling kind of pulled in two directions, which are sort of incompatible because of the amount of time commitment that a physical career like medicine takes.[00:32:25] Nathan:Yeah. And it's hard when you're like, if you have a 10 person team and you're, you're the only one that's part-time right. Like that, that will result in, you wish you could spend more time with the team. You, you know, you being the bottleneck and things, you shouldn't be it made me think of like the, on the team side of things.There's a movie called the intern, Robert DeNiro and Hathaway.[00:32:44] Ali:No, yeah. I really enjoyed that. It[00:32:46] Nathan:It's a fun movie.And there's a scene in it. So Anne Hathaway runs this, like a fashion tech startup, but th but there's a scene early on when she's like rushing from thing to thing and everything is going to her for approval and all of this stuff.Right. And I remember watching the, how she's so important. It'd be nice to be that important. And then the second one, you stepped back and you're like, that is a terribly run business. Like, what is she doing? You know, like the whole thing, if she wasn't there, the whole thing would fall apart. Cause no one would have our approval for like the homepage designs or, or whatever else.And so, going back to the hub and spoke thing, that's the, you know, you'd like watch that little clip of the movie and then go, okay. That, but the opposite, like that's[00:33:30] Ali:Yeah,[00:33:30] Nathan:To go.[00:33:30] Ali:Yeah. There's one. So, often, you know, someone in my team will message me being like, Hey, you know, we, we need to discuss item X. can you, me and Angus hop on a call and discuss item X. And these days are reply with, can you and Angus discuss item X? Like, do I absolutely have to be on this call?And they're often like, oh no, I guess you don't. Yeah. You know, I mean, I'm just gonna take care of it. I'm like great, wonderful. and I'm always surprised when that works. it's like, oh yeah, this doesn't work. I actually don't need to be involved in everything. but I guess it's, it is that balance of, and I think sometimes the team does feel frustrated that I I'm involved in too many things.I've heard and they feel like maybe I don't necessarily trust all of their decisions. it's like, you know, my name that is going on all this stuff and I trust, but I want to, I want to be able to verify, like if I ask why was something done? Like why, why that pricing plan, rather than that pricing plan,[00:34:22] Nathan:Right.[00:34:22] Ali:Like a reason behind it beyond, oh, it's just, we just sort of plucked numbers out of thin air.[00:34:26] Nathan:Yeah. So two things that makes me think of is one, creating a culture where asking questions is encouraged and not just, Like asking questions of like, Hey, could you explain this to me? I truly don't understand it, but, but also like asking for, is there a reason behind this? You know, why did you do that?And then the other side, when people come to you and say like, Hey, what do you think we should do? Then you ask them, what do you think we should do?And then going like, oh, well I think X, Y, and Z. And you're like, okay, why do you think that because of this great, let's do that. You know, you have more and more conversations where like people come to you and then they make the decision and[00:35:05] Ali:Yeah,[00:35:05] Nathan:Place.[00:35:06] Ali:Yeah, yeah. I'd love to get to that point. I think I need to do a better job of, of doing that. the most, the most obvious example is like when we're brainstorming video content ideas and we're coming up with titles. so we had a meeting earlier today and, you know, the team came up with a few concepts and like 20 titles for each one.And then I made the final decision. I was like, oh, I kind of liked the sound of like title number five. but what I probably should do in that context is, okay, Gareth, if you were making this video, what title would you go for? And then kind of seeing what happens. And I guess there is an element of like, you know, I, I trust my gut on what makes a good title more than I trust anyone else's in the team Scott's or what makes a good title.But I'd like to be able to either train someone it's hard to train someone for this, like find someone who's got like trust more. And so who, who I can just fully outsource the responsibility of coming up with a decent title for, because it is such a huge part of what makes a successful YouTube video[00:36:00] Nathan:Yeah. Okay. On those lines. When you make a video, do you know how often do you know when it's going to be like a video that really hits?[00:36:09] Ali:Think about 20% of the time.I can, I have a gut feeling that, okay, this could be a banger. and th the way I think about it in my head is sort of in terms of Banga potential. So a video called I dunno, nine passive income idea is how I make $27,000 a week that has high bang of potential, a video call.The power of positive thinking the potential, like that's not going to be back. It's like, okay, can we increase the bang of potential by making the title more clickbait? and so for example, you know, I've been working with a life coach for the last few months. I want to make a video about it. I've been thinking, you know, how, like really the thing I worked with them on was how to figure out what I want from life.But a video called how I'm, how to figure out what you want from life. You know, maybe two out of five bang of potential, a video called I hired a life coach for $3,000. Here's what I learned. That's got bag of potential. And so often it's just like a tweaking of the title where it's like the more click baity and sensationalized the title that is annoyingly often.The thing that chorus that correlates most strongly with how much of a banger is this city you're going to be. And the formula that I try and use is sensational click baity title combined with like very deep nuanced. So that someone clicks on the video thinking, huh? And then they're very, very impressed by the production value by the structure, by the academic newness of it, by how awful it is.I think it's crossed the Pepsi, at least that's the intention.[00:37:32] Nathan:Okay. That's interesting to me. I have this like running fantasy as I teach. People how to build wealth and make money. Like, those are some of my favorite topics. I can talk about them all day. And so I was joking with someone that I was going to do, like these real estate seminars, you know, that you see advertised where it's really scammy or you're really just paying for that person's private jet.You know, or it's like, it's the, the MLM equivalent, multilevel marketing equivalent of whatever. Like I'm going to use the same tactics, but then like actually deliver real value. And like the ticket that I charged would just be like 50 bucks and it all go to, I don't know, clean water, charity water, or something like that, you know, basically saying like, I'm going to hook people in with the same thing, clickbait and then deliver, like substantial value that will actually be life-changing.Yeah. And so[00:38:23] Ali:Yeah.[00:38:23] Nathan:The same thing. I like it.[00:38:25] Ali:Yeah. I think it's a great idea because you kind of need to use the clickbait. Like there's literally no way someone's going to click on something. there's a channel, V very, to cm, which made an amazing video, like a few days ago, about the difference about the importance of clickbait and how, and how much it works.And his overall point was that like click, click bait is kind of the wrong word. There is sort of, I think, I think the two terms where there's this sort of like intrigue Bates, which is that, you know, oh, this is interesting. I want to, I want to click on this. And then there is, I can't remember what he said, but it's like, sort of trashed bait, which is that I'm going to stick a bikini model on a thumbnail and has nothing to do with that.But, and so there's those two, two different ones where like, in a way, the way that you title something or the title of your book or the cover of some. It's so, so important for getting the message across. And we shouldn't see that as being a bad thing. Whereas the word clickbait, it includes, you know, things like what is what what's a good headline designer.What's good marketing coffee, but it really shouldn't because clickbait has, it is a dirty word, but it, it shouldn't be because the cover of something is so important to how that thing is perceived and whether people are going to see it or not.[00:39:33] Nathan:Yeah. Yeah. That makes sense. How do you think about the thumbnails and then like the, say the first 30 seconds of the video, those are two separate questions, but as both of those in, in driving engagement,[00:39:44] Ali:Yeah. So thumbnail is really, really important. I think on our channel, we were bad at thumbnails. I'm not a fan of our thumbnail style. we're trying to evolve and iterate on it over time whereby the, you know, and so w w whenever someone's an early stage, utuber, it's like, you're, you're uploading the video.And then you think about the title. And then you think, okay, let me find a, still from the video that I can use with someone else, and then maybe you downloaded it, ramp up the contrast saturation, blah, blah, blah, sticker, clarity, filter on it, and maybe put some text on it in Canada. That's like the, the new YouTube, YouTube way of doing it.When you become a little bit more pro you start thinking of the title in advance anything, okay, what's the title of this video going to be, and then you make the video and you've got the title already. but the thumbnail is still a bit of an afterthought because it's, it's quite hard to think about something else.And that's the point where we're at. and the gold standard is where you have full about the title. And you have literally made the thumbnail before you even think about writing the script for the video. And that is a place where we would like to get to. so we're looking to hire like a graphic designer and, you know, a YouTube channel producer whose job it's going to be to work with a graphic designer at any time, because we, we we've got hundreds of ideas at the top of our pipeline, but at the moment, our bottleneck is in developing those ideas, crucially with a decent title of decent thumbnail and a rough talk, rough amount of talking points.And so, yeah, we're doing everything we can to make the thumbnail more of a first-class citizen, because it's just so stupidly important on YouTube. And in fact, often, you know, if, when I've heard YouTubers would like 10 million plus subscribers speak about thumbnails, they view the thumbnail as being even more important than the title, because the thumbnail is the first thing that really catches the viewer's eye.And the first thing that they see. so yeah, I think we do vaginal thumbnails. Well, relatively speaking, and we're trying to improve at it. I think equally the first 30 seconds is just ridiculously important where everyone's attention is so like all over the place, but if you don't hook the viewer within the first like five seconds, you see that huge drop off in engagement.And again, other other YouTubers that I look up to really, really obsess over the first 30 seconds to one minute of the video and when we teach our YouTube, of course, and we analyze like, what makes a good, like what do these sort of 5 million plus view videos happen? It's like often there's like a cut every single second in the first 30 seconds, like some new piece of gear or something happening on screen.It's just like so rapid and fast and really holds your attention. Whereas for the rest of the video, you can kind of switch to a car every five seconds or something happening every 10 seconds, the ten second rule. but certainly the first 30 seconds, like Panama, it's gotta be like really, really, really sharp and on points.Otherwise people just don't watch.[00:42:16] Nathan:Yeah, that's fascinating. I'm realizing that it's true for a lot of channels I've seen grow really quickly are employing the same things. that's something that's I wanted to ask you about on the monetization side is you're selling a high value course, to like a big audience, you know, 2 million subscribers on YouTube.You also have a what? Lower a hundred thousand subscribers on, on email.All right.[00:42:38] Ali:Yeah.130 or something.[00:42:41] Nathan:Nice. What's the, like, how does your approach differ when in promoting that, you know, a new course, like the part-time YouTube academy on YouTube versus on email.[00:42:50] Ali:I think I'm still scared of selling. It's really bad. I need to get over it. I was, so I was really, really scared of selling like a year ago. And when I had the idea for the part-time YouTube academy, it was on like the 16th of August, 2020, where I wrote the notion page about it for the first time I was thinking, okay, you know, this, this is either going to be a Skillshare class.I eat free, or it's going to be like maybe a 50 to $200 kind of self-paced course. And you know, I can really, really over-deliver on content. Cause I know what I'm talking about here. And so $200 is an absolute steal for this. No one's ever going to complain that this is not worth it. And then I spoke to, I think people that you probably know Tiago Forte and David Perell who run their own like cohort based courses.And they challenged me. You know, what if you had to do this live? What if you had to charge a thousand Abdaalars for it, how would it change your approach to the course? And starting to think in those terms made me really changed the way that we did a personal course and it became a high, second thing. It made me realize that actually what the world needed was not, or what needed to be grandiose, like what the internet needed.It was not, another YouTube or making a self-paced course on how to be a YouTuber. The thing that's actually holding people back is the accountability and the community. And these are things that you get in a live cohort. but getting back to your point about how, like the difference in, in setting it.So we actually only advertised it on Twitter and on the meeting list. initially I didn't even mention it on YouTube because I was so scared of mentioning the course on YouTube. And I think the reason I was so scared of mentioning the course on YouTube is a problem with YouTube that I've spoken to a bunch of other creators about, which is that the people who comment on the videos do not reflect the audience at all.[00:44:29] Nathan:Right.[00:44:30] Ali:Like, if you think about who comments on a YouTube video, it's generally kids, it's generally kids with with enough time on their hands to comment on to comment on videos. And so I was always scared. Like, my audience is not going to appreciate the fact that I'm selling a high ticket course. They're going to think I'm a snake oil salesman or something like that.And my audience mental model was the people who comment on my videos. And it took me a little bit of like an epiphany to realize, hang on, the people who I'm targeting are people with jobs. People would like, you know, six figure incomes, people who want to do the creative side hustle and take it seriously.They are not the 14 to 17 year old kids commenting on my videos. And that was such a major like revelation of like, I can actually completely ignore the comments and I can just go by the analytics that tells me like 40% of my audience is age like 24 to 36 in the U S fantastic. Those are the people I want.Whereas on email, you don't really see that as so, so clearly. And so I think, and especially because I've read your stuff. Read a lot around email marketing, but so little around YouTube marketing. I'm much more comfortable selling on email than I am selling on YouTube, but it's, it's something I'm trying to get better on.So,[00:45:31] Nathan:Are you able to track attribution for signups or that kind of thing of what's coming from YouTube versus email now, right? You're doing at least some promotion of it on YouTube.[00:45:40] Ali:Yeah. we actually, so in the first cohort where we did, we didn't promote on YouTube at all. So it was like 50% Twitter, 50% email, I think for the most recent cohort, even now we don't really promote on YouTube very much. It's less just like a very, very subtle casual plug at the start of a video.I think about 30% came in through YouTube and the rest came in through again, Twitter or email.And so, but you know, one of the things that we're hiring for is a marketing marketing manager to basically just lead marketing for the YouTube academy. And that was some of the stuff that, that your pal Derek was was, was helping us with.[00:46:13] Nathan:Yeah, they're good at all of that kind of stuff of taking, I mean, all the things that I did over the years of like, oh, there's, one-off push here, they're entering into like, okay, that was great. Look at the results we got from it. Also, we're going to do it as a system now, and it's going to work like this and it's going to drive consistent results over time, rather than like these spikes or that sort of thing, which I'm good. okay. Something else like in that journey, we kind of left off as you were, you know, I guess the last we're talking about YouTube numbers was, you know, like five, 10,000 subscribers. I want to hear a little bit more about going from that 10,000 to 100,000 and then like, I think it's a huge jump, but a hundred thousand to 2 million.[00:46:54] Ali:I think it is absolutely fancy. It's just the law of compounding and consistency and, you know, the results happen very, very slowly and then very, very fast. And before you know it, you know, Jim Collins, I thing has that model of the flywheel that it takes. It takes a hell of a lot of energy to get going, but once it starts to go, then it, it becomes unstoppable.I think it's, it's the case for any interesting kind of compounding could growth projectory, you know, YouTube channels, convert kits, any software platform that's growing. and so in year one, I think we hit maybe like 20,000 subscribers by the end of it. Then year two was probably the next few hundred thousand year three was the next like million in year four.It's just wrapped up wait, where we just hit the 2 million mark. And then at the end of year four, so it was just, you know, perfectly matches it maps onto one of those exponential growth curves. The scary thing about that is that like, if you extrapolate it further, that means we're going to be on like 4 million subscribers by next year.And that's just completely unfathomable to me because it's like, okay, that's just never gonna happen. And there is a point at which the, the compounding growth curve stops, That's the thing that I worry about. I don't really worry about it. That's the thing that I'm trying to build more and more like pillars of support around the business, a diversification, more into courses, more into books, more into stuff that is dissociated from my personal brand and also from my personal YouTube channel specifically.Yeah, it's, it's, it's weird. It's one of those things we look back on and you kind of forget like, oh yeah. When, when I started, like, I remember like when I started working as a doctor, I had, I hit 50,000 subscribers like that, that, month. And then a year later when I was having my first like appraisal, where they, your supervisor looks at how good a doctor you were.The first thing he said to me was there were 263,000 people following a YouTube channel. How the hell did that happen? And so I have that number in my head is like, oh yeah. Once I, at the, at the end of 2019, when I, when I finished my first year, I was Dr.. That was what. And then it was like my it's my second year of working as a doctor when the pandemic struck and the pandemic, me and my channel really take off because all of a sudden people were sitting home and watching YouTube videos.I think that was when we had and subscribers. and now a year on from that point, we've just had 2 million and it's just been just insane, insane growth. but obviously consistency compounding the thing I always tell my students is that, you know, YouTube can change your life. but you have to put out a video every single week for the next two years.And if you do that, I guarantee it'll change your life. I can't put any numbers. I can't tell you how many subscribers you'll have or how much revenue you have, like a hundred percent guarantee. You will change your life at the very least in terms of skills or connections or friends, or, you know, just opportunities that will come your way as a result of posting consistently on YouTube.And everyone here is that advice. And like, you know, so few people actually follow that,[00:49:43] Nathan:Yeah.[00:49:44] Ali:With me. You know, I've been trying, I've been trying to hit the gym for the last like eight years. Never done it consistently until I got a personal trainer and now I'm actually seeing gains, Yeah, compounding and consistency, which is some of the stuff that you talk about as well.[00:49:55] Nathan:Yeah, for sure. Is there a point in there where you saw things plateau at all? Like right. There was the, a flat part and an S-curve where you started to think, okay, I need to change something or push through this or anything like that, or has it always just been consistent?[00:50:10] Ali:Yeah. So I don't really look at the numbers very much. the way that's, you know, my, my theory of numbers has always been that like the, the numbers were, were always outside of my control. And the only thing that I could personally control were the number of videos I was putting out and how, how good I felt about the quality of those videos.That second one I got rid of very quickly, because I realized that what I feel about the quality of my own videos does not match at all what the audience feels about the quality of my videos. And therefore I'm not even gonna think about that. So the only metric I care about is just putting out two videos a week.The thing that I, I think of more. When it comes to, okay, these are, this is a bottleneck. We have to like push through. It is when the channel starts to feel like it's a bit stale. And there's been a few times, boy for four and a bit years now, or I felt like, okay, we've kind of been doing the same thing for awhile and it worked to get us here, but maybe what necessarily got us there.So most, you know, initially it was like medical school stuff or it's that Kevin doing medical school stuff for a whole year. I need to kind of branch out from this. And it was like student stuff in general. And it was like, okay, I, I'm not, I'm not graduated to the student. There's only so long. I can keep on just peddling the same stuff around how to be an effective student.It's all kind of, of it. I mean, it's, it's obvious, but it's, you know, there are a finite number of things. There's like a few techniques that work really well and you make videos about them over and over again. So it, it feel stale now more, more recently, the productivity hustle lead type stuff has started to feel a bit stuck.And so now we're now thinking, okay, what's the next level? And that was what prompted the idea to start any podcasts that we're what doing, trying to mimic basically the Tim Ferriss show or impact theory or school of greatness, or these other sorts of broadly in-person interview podcasts interviewing like entrepreneurs, CEOs, creators, and other inspiring people about how they find fulfillment in work and in life that's like the spiel for it.And I, I, I hope that will be like the next level, and be able to expand our content beyond just me talking about productivity or me talking about tech.[00:52:06] Nathan:Right.[00:52:07] Ali:Mostly based on that gut feeling of stillness that I feel okay. The writing on the wall is that this is going to decline unless we change something rather than about the numbers.[00:52:15] Nathan:Yeah. That makes sense of figuring out. I mean, it's in the quality of the product that you're delivering, you know, and making sure that you're continuing to innovate their innovative buzzword, but you know what I mean? so one other thing that I see you doing throughout all of this is making sure that it's fun.And so I'm curious for your[00:52:33] Ali:Yep.[00:52:33] Nathan:On like, what's your philosophy around making this fund? why is that important instead of just like, or in addition to the like rigorous discipline?[00:52:43] Ali:This is literally the thing that I'm writing a book about right now, which is that, you know, people have been asking me for it for years, how you said productive. Even when I was in like high school and university people would be like, oh my God, you do so much stuff. Like how, how are you so productive?How do you, how do you will have it? And it always felt a bit like, you know, people, people had this weird image of me that I was some kind of productivity guru. And now the comments on my videos, like, oh my God, he must be some sort of absolute machine. But you know, I, I, I, I line until like 11 o'clock in the morning this morning, the only thing that got me out of bed was a zoom meeting with the team.And I scroll Twitter for a solid, like 45 minutes today. And I wasted, you know, I, I finished up with a call about half an hour before we were meant to start recording. And I was like, ah, How much work are you ready to get done in half an hour at school, Twitter, often Ariba. So I'm just like genuinely really lazy.And all of the people who actually know me know that I'm really lazy and are completely baffled that the internet thinks I'm a productivity group. I think the, if there is one secret that secret is that I just make everything that I do really fun. and so I think that's got kind of two components.The first component is finding things that you already find fun and then doing them. and that's fine. it's, it's, it's quite hard to do that because often the things we find fun are the things that are not really suitable for a career. Like, you know, I enjoy playing the guitar and do I ha I enjoy playing board games.I enjoy watching Netflix. Like it's very hot. It's hard to make a kind of sustainable career out of that probabilistically. Yes, I could become the next ninja, but it's pretty unlikely I could become the next John Mayer was pretty fricking unlikely. and so the, the lever that I try and pull is figuring out ways to make the thing that I'm already doing, figuring out ways to make that more fun. And I think I've just sort of been subconsciously doing this for my whole life, because I don't like doing stuff that's boring. I only like doing stuff that's fun. And I figured out like a few different, different things I can do that. Basically it tricks my brain into having more fun, which makes me more productive, but it also makes my life more happy.And it also means I don't really need discipline because it's like fun. Like, you know, when

Today I talk with Heather and Nathan Thurgood and discuss their advocacy In the Huntington's Disease community. Nathan Is living with HD and Heather Is his biggest supporter, cheerleader, and advocate. Together they have been able to raise awareness and Impact so many lives through participating In clinical trials, speaking at events, and sharing their journey with HD anywhere and everywhere they can. They truly are champions for Huntington's Disease and are changing the world one day at a time. They gave me so much hope and happiness In our conversation together. I hope you enjoy It as much as I did. Follow Champions:https://www.championsforhd.org/https://www.instagram.com/championsforhd/https://www.facebook.com/championsforhd/Follow Shelby:https://www.instagram.com/shelby_lentz/https://www.shelbylentz.com/https://www.facebook.com/shelbylentzmusic/?ref=bookmarksSupport the show (https://www.championsforhd.org/donate)Support the show (https://www.championsforhd.org/donate)

更多英语知识，请关注微信公众号: VOA英语每日一听 Julia: Hi, my name's Julia and I am talking to Nathan about his wedding experience. Nathan, tell me how was your wedding day.Nathan: My wedding day was, I guess, mixed. I think the build-up to my wedding was quite funny. I didn't feel in control of my wedding so we went to several different, I don't know what to call them, wedding shops or wedding planning companies and they asked us how much money we could spend first and the first thing that comes out is how much money do you think you're going to spend on your wedding and I felt that was kind of like a real personal, a kind of an embarrassing question as well because...Julia: You're British.Nathan: We didn't really have much money. Well, yeah, cos I'm British maybe.Julia: Can I ask you how much did you spend on your wedding?Nathan: Oooh, it was I guess about, in pounds it would have come out at a guess about fifteen thousand pounds.Julia: I've heard that's the average, I think, for a wedding. I don't know but...Nathan: So I wasn't doing my wedding in England, I was doing it overseas and there were a few things I had to get to used to. And one of those things was the wedding company that we chose offered us some, some different priests to do the ceremony for us but they're not real priests.Julia: Like a priests menu?Nathan: Yeah, it's like a priests menu and you've got these like different guys who are playing the role of the priest for the wedding so I happened to know all of the guys in this menu and they said to me, they said to me ah so this guy's really, really popular. Barry priest is like the most popular priest, we really recommend him and I was looking at the picture thinking I know Barry priest and last night I went drinking with Barry priest and he, he didn't look like a very good priest last night.Julia: You got married by your drinking buddy.Nathan: But we didn't in the end. We avoided that but, yeah, all these different choices on a menu, I felt like a McDonald's menu rather than like, it was like do you want a large priest or a small priest or like do you want extra large candles or like small candles in your wedding ceremony lunch and different things so it was kind of, yeah, it was kind of McDonaldized kind of wedding where you had to choose this option or this option and it didn't feel very personal to me at the beginning.Julia: Was it romantic, do you think it was romantic in the end?Nathan: Is a wedding supposed to be romantic or is it supposed to be a party?Julia: I'm a woman and I think it's supposed to be romantic.Nathan: Yeah, maybe I let my wife down a bit.Julia: Ceremonial, maybe ceremonial, was it ceremonial?Nathan: Very, very.Julia: What did you wear? Did you wear some special clothes?Nathan: Like a morning suit, you know like in England you have a grey morning suit, top and tails, but we, mine was black and I felt like I was...Julia: That sounds cool.Nathan: And I felt like I was like kind of Reeves in the Matrix going in with this like black suit and long black tails and...Julia: Did you wear shades?Nathan: If I could have got away with it, I would have.Julia: What was your wife wearing? Was she in black as well?Nathan: She did two different dresses.Julia: Oh, nice.Nathan: And so she had this white wedding dress for the fake church ceremony and then afterward during the lunch she got changed into a dress and it was made from, it was made from an old Japanese kimono.Julia: Like silk?Nathan: So it was all made of silk and it was bright pink with peacocks and flowers and things.Julia: Sounds gorgeous.Nathan: And she'd taken it to a shop and they'd converted it for her.Julia: Sounds beautiful. Does she still have that then? Did she keep that?Nathan: Yep.Julia: Does she still wear it?Nathan: Does she still wear it? If she had an occasion, there's never going to be an occasion where you can wear that dress but it's a pretty amazing dress to look at.Julia: So I guess it's about the memory though, it's certainly, it's certainly a memorable occasion.Nathan: Yeah, well, we've got videos, we've got albums, we've got all sorts of stuff.Julia: Was it stressful? Was it a stressful experience?

Nathan Dass Is A Boise Local and a long time friend. Nathan Is an essential laborer In Boise and is doing his part of Social Distancing. Nathan has spent time in a few other states such as Texas. In this podcast we talk about Tiger king, Other podcasts we like to listen to and a few other fun shenanigans. Enjoy. Apple Podcasts YoungBloodPodcast Spotify YoungBloodPodcast @YB.Podcast Inastgram

Now that we're a few weeks into the new year it's time to evaluate our progress. Are we still on target with our goals? Are we busy or are we moving the needle? Join today's discussion and share your bad habits below. Episode Transcript RTRE_Ep_47  Audio length 22:49 RTRE 47 – Are You Busy or Productive? [music] [Chris] Welcome to re:Think Real Estate, your educational and hopefully entertaining source for all things real estate, business, news and tech.  [Christian]: I am Christian Harris in Seattle, Washington. [Nathan]: Hi, I am Nathan White in Columbus, Ohio. [Chris]: And I am Chris Lazarus in Atlanta, Georgia. Thanks for tuning in.  [music] [Chris]: Everybody and welcome back to re:Think Real Estate. I am Chris Lazarus here with my faithful hosts Nathan White and Christian Harris out of Columbus, Ohio and Seattle, Washington respectively. Thank you so much for tuning in. It is a still relatively early in 2019 and we were just talking about you know this is right around the time some people start dropping off their new years' resolution. So I hope…I know it's not anybody in our audience [laughter] but now we start to get in the busy time of year and it's that definition of busy.  What is busy? Is it…Is it necessarily productive or is busy making us money or is busy just the thing that we have to be doing? Because I don't know about you all but picking up my thumb that's like my thing. If I am not doing something right now I start to itch. Like I find myself sitting down sometimes and maybe I will be waiting on somebody for a business meeting and I have to cognitively think like actively think and just saying “You know what I should learn to comfortable just sitting and waiting” and it's something that is really weird. But when I am in that mode I can actually think about what needs to be done and I think that sometimes when we're busy we don't always do that.  So today we're gonna be talking about what the difference is between being busy and being productive. Christian? You're a broker owner, you're starting up a new company. You're back into selling. What…like how are you challenged with being busy versus how productive is your busy time? [Christian]: So you know the funny thing is and I don't think this is an experience unique to me but when I am talking with other agents or just people in general you know the small talk is you know “How are things going? How are you doing?” And the response 95% of the time is “I am so busy, so busy so much going on”. You know, and I think subconsciously we kind of wear that as a badge of honor like “I am so important that I am busy all the time”. At least in real estate. You know “I am just scrambling around because I got so much work”.  But the question really is “Is busyness a badge of honor or is that more a sign of no you're just ineffective in what you do and how you spend your time?” Which is why I find this conversation so interesting because being productive is way different than just being, busy you know. I can be busy and feel like I am getting stuff done by checking off my 2000 emails but you're not actually moving the ball forward. You're not actually accomplishing goals versus “I've got my dedicated time to do this one task and I am focused on, that's the only thing I am doing”.  You know, you can elude to the distractive nature of technology and things these days and make a whole episode on that. But you know I feel that same pull. I am older so and I like to say I am bilingual you know I grew up in a day before the internet and so I remember doing book reports with books you know and card catalogs as the research tools and that sort of stuff you know. [Chris]: You're not that old. I still had that. [Christian]: Yeah I am just saying you know. I remember a day before that and then in my 20s you know adopted technology as in internet and tan smartphones came online and what now.  [Nathan]: I was using an Atticus. [Christian]: And so I remember the times of… [Chris]: Hang on Nate did you just say you were using an Atticus? [Nathan]: Yeah Atticus. I am the old one out of the group [laughter]. [Christian]: Only by a couple of years. But the point is I feel that pull too to like never have down time. To always be doing something, always be stimulated with input. And usually that's in the form of I am sitting there like you said in the doctor's office and I feel the draw. Uncontrolled, my hand reaching my pocket pull out my phone and just mindlessly check Facebook or Instagram or emails like we can allow yourself some time to like reflect and think and ponder which we don't do a lot so we tend to live our lives in a stimulated anxious responsive posture. Instead of proactive duffle posture. [Chris]: Definitely. [Christian]: You know there is a lot in that but I think the business plays into that. [Chris]: So Nate obviously you've shared with the audience that you suffer from ADHD. So is busyness a good thing for you or does that impede your productivity? Like what's the difference between being busy and being productive for you? [Nathan]: Yeah I mean that is the million-dollar question right. I can be busy all the time. But I am not producing results.  [Chris]: Yeah you're good at that. [Nathan]: Yeah. So for me it's about…For me personally again it's about having a very regimented schedule. I mean those that are friends with me on Facebook whatever they're like…I actually had someone the other day saying “I don't know how you do it day in and day out like you check into the gym at 5 a.m.” Like I live and die by a schedule.  For me to get a result or to have production right productivity instead of me spinning my wheels getting around on Facebook and [censored] around and all that [censored] I have to be very regimented, right. Which means when I get to the offices one if it's quiet and the first thing I don't do is I don't get on Facebook right. I have an order to the way I do things because once I get into those realms if you would than I would squirrel.  [Chris]: Rabbit hole. [Nathan]: Yeah squirrel I am all over the place. So I have to be very regimented in what I do. And I will tell you like if I get out of that rhythm it sucks. But when I am in it I am in it. And man I tell you what, I feel great. And so I think you can tell as an agent broker whatever you are you don't have to have ADHD but you can follow…just have…I don't know kind of a purpose drill in life. Have a purpose to what you're doing. You see a lot of the people they get in and then they get on Facebook and then they're looking at their messages and they're here and they're there but they're busy but they're not producing any results.  So I…the way you quantify that to me is did…You know I set a goal list. I have to have a check list. And once I check things off it feels great. I perpetually add to that list. But, you know, in our world how do we judge our productivity? Dollars and sales right? I mean in the restaurant industry they used to say “Sales cure all”. And in our industry I think that's applicable right.  How productive are you? You know you have the agent that says “Oh I was such a great year I did a million dollars”. For them maybe it's great. You have the other ones that say “Hey I did 42 sides or 8 million dollars”. You know I think there's a big difference of who is productive and who is not. And I am giving to each his own. I am not trying to say that if you did a million dollars in 3 sides or whatever you weren't productive but let's be honest you probably weren't. [laughter] So… [Chris]: Well I mean you're right you probably weren't because the average full time realtors are doing 11 sides a year. [Nathan]: Is it 11? [Chris]: I think last I heard. [Nathan]: That is so many. [Christian]: That sounds high. [Nathan]: That sounds high. I thought it was like 6.6 full time. [Chris]: I think the average full time relator not the average realtor. [Nathan]: Oh yeah the average full time I get it.  [Chris]: The average person who makes a career out of it is doing about 11 sides. Not 11 transactions but 11 sides.  [Nathan]: Remember too we are realtors so what do we like to be about? All about being a realtor right. I mean God Almighty you know Facebook all watch it “#realtorlife #showingthistoday”. [Chris]: “#blast” [Nathan]: Yeah like it's like…Like it's all about you know last episode, right, we were talking about being client centric. I mean hell that's all about just being a realtor right. It drives me [censored] crazy. Like #realtor I am like listen our life isn't that bad right. What we do… [Chris]: I think what Christian just said a few moments ago is just spot on. It's about feeling important. People like feeling important and a lot of people in real estate are like “I am a real estate agent. I can help you with the biggest financial transaction of your life. I am so important”. And rather than focusing on going out and getting business and building a business they're focusing on being a realtor.  I had an agent that worked with me for a little while. It was a young kid just starting out. And we quickly realized that he was in love with the idea of being successful more that he was willing to work at being successful. And that is a big difference because you can be really busy and be in love with the idea of being successful. You know go to a show room and take picture with a Bentley and you know have your girlfriend modelling in your Instagram account. It really…But if it doesn't come down to you actually making money it doesn't really exist.  So I think that a big thing is feeling important and Christian hit the nail in the head with that. And people can be busy to feel important. That doesn't mean they're productive. That doesn't mean they're working on their business. So… [Nathan]: Yeah it takes me about the time one time I…another agent we were talking We did not know each other. We had met and I said “Oh you're a real estate agent?” she said “Sure I sure am?”. And I said “How did it go last year?” She said “It was great, I closed 4 houses.” [laughter] And I laughed and I said “You're not really an agent.” She got really mad. [Christian]: Can't imagine why. [Nathan]: [laughter] But again I go back to what you said about what Christian just said. It wasn't about…I don't know, I didn't feel any passion to what she was doing. You know I think those of us who really enjoy what we do we do it because we are passionate about it. Not because we love houses or watch HDTV or anything of that [censored]. Like we love what we do. We love…you know there is that narcissistic side again of you know part of it. But there's also the feeling of just helping somebody buy their home that is very rewarding. And so I don't know I could go preach on a lot of different angles on it.  [Chris]: I couldn't agree more. Now I think we kind of got the understanding for the audience of what is the difference between being busy and productive. So how do we focus on being productive with our time? How do we focus on not dealing with the busy work? Because there is about 20% of our daily activities that are gonna result in about 80% of our business. The parietal principal works in that way. So how do we take that 20% and be extremely productive in that? So that it is not really blowing out of proportion or taken away from the other aspects of our business? [Nathan]: How do we…? Are you asking how we measure like…our productivity? [Chris]: How do we focus? How do we not deal with the busy work? [Christian]: There's also all sorts of tactics on focusing. We've had several opportunities on it but I think it is good to kind of go over some of the basic stuff because you know even maybe in super organizing systems like think you know “I am efficient with my time” I get distracted you know in real estate you've got your phone blowing up in fires. You have that put out and you know  ”I am trying to time block to get this project done and the phone won't stop ringing”. And you know… So it could be very challenging but I think kind of like you know quote “new year's resolution” you just gotta if you follow the horse you gotta make it on keep going. Remind yourself “OK I need to turn off the technology and just be self-aware of like the things that are drawing your attention away from actually being on a state to focus on one thing at a time.” You know don't buy into this like “I can multitask and I can have my social media up while I am into MLS and while I am drafting an email and working onto the project”. You're not gonna get anything done and you're gonna be super stressed out.  [Nathan]: Multitasking is [censored] people. Multitasking is for people that can't focus on one thing at a time and complete it. So don't multitask. Get it done. Sorry I get really weird about that. [Christian]: Alright there you go. [Nathan]: Yes.  [Christian]: You said it.  [Chris]: You have no compassion for it. [Nathan]: Yes I can't stand people saying “I am multitasking”. No you have the inability to focus on one item specifically that's what that is. That is 100% what that is. [Christian]: That's a lack of discipline. [Nathan]: Yes. There are a million things to…that you can use in tools and resources. Again just daily habits, you know, goals. Writing goals and not looking at them a year later but looking at them daily. Periodically or whatever it is. I mean. Or you can be really anal like me and have a check list.  [Christian]: Nathan you're making me feel bad because you know that's illuminous stuff but I don't do it all the time. You're hurting my inner child. [Chris]: Yeah but…Nate how is that CRM going? [Nathan]: [laughter] My CRM is going horrible. Why? Because I didn't put a date on it. I know it. I own it. [Christian]: What's your date? Give me a date now.  [Nathan]: I have not…I don't have one yet. [Christian]: What's your calendar? Do it now. [Nathan]: I don't have one yet. I probably…I am actually. [Chris]: There's a couple…OK getting back on track I think there is a couple of things that work for me in trying to aim and being more productive. One is, I don't take on more than I can handle at any given time. [Christian]: How do you know what you can handle? [Chris]: Huh? [Christian]: How do you know what you can handle? [Chris]: Trial and error.  [Christian]: OK. [Chris]: When I realize that I am not spending enough time with the family and some of the projects that I am doing I don't see a future to, whether that be it doesn't improve the bottom line, it doesn't like it's not gonna be used, the reaction to the agent is not exactly the reaction that I thought it would have. I'll cut a project.  I don't take on too many volunteer roles. Like if I take on a new one I give one up. But when I do something I…when I changing a habit, when I am adding something into my routine, I do it one step at a time. I don't go and change my entire routine overnight. And for…you can go back over the last 3-4 months and I will talk about how I changed my entire morning routine off of what Nate did after what Obi said after Obi's show. But start small. Don't change the whole routine all at once.  If you're gonna start using a CRM you dedicate that is what you're gonna do and you just do that for you know 30 minutes a day every single day and then once you're used to doing that every single day than you add something on. But you don't say “It's 2019 I am not gonna use a CRM I am gonna call everyday, I am gonna follow up with this marketing, I am gonna do this that and the other and I am all gonna start it on January 1 and guess what it's now a few weeks in and I have dropped off the map”.  Well you dropped off the map because you have added too much to your plate. Start small than you slowly add on. And then the other thing that helps me be productive is a to-do list. Like what Nathan said. Put a checklist down. I aim for the top 3-5 things that I want to accomplish in a day. I write it down and then those are the first things I work on. So at the end of the day whatever has happened, whatever has gotten done I know that I made at least 3-5 different things that are moving the needle forward in the business every single day.  So that helps with the busy work. Because busy work comes. I got on 100 agents and it's all email all the time. Lots of administrative, lots of busy work. But I always get the productive stuff done. [Christian]: I would love to touch on what you just said because I couldn't agree more on the…because I was just the king of it for the longest time, taking on or challenging myself to something that was too big instead of thinking about it logically. So I look at it from a new agent perspective. I mean you meet a new agent. New agent says “Yeah I wanna do 7 million in sales next year” [laughter]. “OK right. Yeah right”.  We laugh now right and I would love to see it. But how about instead of saying 7 million in sales lets focus on just the first one. Right. And I think it's our human nature to set these lofty goals and then we fall short. We get discouraged and then we just quit at it right? It's OK to have a goal that is somewhat ambitious. But don't…we all know that if it's not within reach it's not worth doing. I mean myself I got a …I got a running partner, Jason Perkins here in town and we both thought about signing up for something called the Moab, 240, it's a 240 mile single loop run through in Moab, Utah, Arches national part of that whole area. 5…5 days around this thing.  I really want to do it. I like…It's on my list. And he said “Do we want to do it this year?” And I had to think through that for about 3 weeks. And as much as I wanted to say “Yes let's do it this year” I said “Eh I need another year to prepare”. You don't know how its gonna be but than it's a little more realistic. To say “I can go on and achieve that”. Maybe I could have done it this year. Maybe not. I think it probably wouldn't have happened but I rather give myself time to prepare to do some other thing. So coming from me, the guy who loves the big things, stepping back and really taking that hard look in the mirror, evaluating what your goals are I think it's huge. Don't bite off more than you can chew. [Chris]: Absolutely. That's been something major. And you to your point Nate with a new agent that's coming in saying “Oh I want to do 7 million” in even taking it a step back. Not even saying “Oh I just want to focus on that first transaction” break it down smaller. “I am gonna focus on getting 7 clients on this year”. Because if you're focusing on just getting the clients the transaction will come. But if you focus on the client you're focusing on the habits and the action items that need to be done to generate business. If you say “I want…I am gonna focus on getting a deal over the next month”. It's not specific enough. “Oh what am I gonna do to do it?” “Well if I am gonna get a deal I need…I need clients right? So why don't I just focus on getting clients and I am gonna aim from 5-7 clients this year. Then I know what my job is. And my job is to build those relationships and get in that position where somebody wants me to represent them”. The transaction will come. Whether that comes in the first 6 months or the second 6 months or the third 6 months it will come if you focus on doing the right things. That's what I got. [Nathan]: Yeah good.  [Chris]: Anything else on being productive? Guys final thoughts?  [Christian]: I don't know. What you said. I have realistic goals. Don't make them crazy. A to-do list is real easy tool and cheap. You don't need…You don't need…paper and a pen. [Chris]: Not even that. Notes apps.  [Christian]: [laughter] Yeah right. [Nathan]: I just say take it day by day. If you know you get distracted and your day goes to [censored] hey you got tomorrow. Start over. [Chris]: Absolutely start over. Don't wait. Don't set…Don't get half way through the year and say “You know what I didn't…I faltered, I am gonna wait until January 1”. Just start the next day. [Christian]: Don't wait until life is perfect and everything lines up just right because it never will. [Chris]: It's never perfect. It's never gonna be the right time. Just make little strives all the time. There's a great book. The compound effect by Darren Hardy, who talks about how making incremental efforts every day is the key to building a successful business. And I like in it to brushing your teeth. You brush your teeth once for 2 minutes, it doesn't do anything for you. But one of my good friend is a dentist. You brush your teeth twice a day everyday it's gonna prevent cavities. It's all about consistency. It's all about the small actions adding up to produce spectacular results if you stick with it. Go.  [Nathan]: So go brush your teeth people. [Chris]: Brush your teeth. [Christian]: That's how the world is conquered. A little goal at a time. [Chris]: That's how it is. Brush your teeth. Your colleagues will thank you and if you haven't already please go to re:Think Real Estate, our website which is rtrepodcast.com. Subscribe to the newsletter and you will get notified every time an episode hits the air. Go to iTunes, Google play, Spotify, leave us a great rate review even if you haven't really listened to the whole episode just give us 5 stars.  [Christian]: Yeah just do it. [Chris]: Just do it. Alright. Thank you so much for tuning in everybody. We will see you next Monday.  [music] [Chris]: Thanks for tuning in this week's episode of the re:Think Real Estate Podcast. We would love to hear your feedback so please leave us a review on iTunes. Our music is curtesy of Dan Koch K-O-C-H, whose music can be explored and licensed for use at dankoch.net. Thank you Dan. Please like, share and follow. You can find us on Facebook at Facebook.com/rethinkpodcast. Thank you so much for tuning in everyone and have a great week.  [music]  

On this special edition episode the KickinShitCrew breakdown episode 6 of season 3 of Insecure. Join us has we recap and discuss this episode and follow us to stay up to date with the show on all social media IG/Twitter @kickinshitpod IG/Twitter @juk3boxjohnny IG/Twitter @missnewbourgie IG/Twitter @soletrsincompany/soletrainco and if you like the show we ask that you.... TELL A FRIEND TO TELL A FRIEND Join the conversation... What now for Molly? Will Issa find Nathan? Is the Lawerence saga over now? tell us your predictions write us kickinshitpod@gmail Or visit Kickinshitpod.com and click “contact KSP”

This week the Nerds trudge on without the help of their fearless leader Nathan. You get a big ole helping of NerdOns this week as they talk about the comics they are working their way through, the games they are playing, and the tv shows they are watching. We answer an interesting question sent in from a listener on the Mailbag segment, and we talk about all the new trailers and Nerd news that has come out over the last week. Will they be able to hold it toghether without Nathan? Is it going to all fall apart? Is it going to suck? Is it going to be funny? Tune in to find out! In the News War for the Planet of the Apes Baywatch Trailer Transformers The Last Knight Trailer The Mummy Trailer Spider-Man Homecoming Trailer Spectral Trailer Southpark The Fractured But Whole Legion Trailer Lemony Snicket's a Series of Unfortunate Events Trailer Ducktales Teaser Peter Vaughan Passes away at 93 (And now his watch is ended) ___________________________________________________________     Have a question for the NWGLS guys? Shoot us over an email at nerdswhogetlaid@gmail.com Follow us on Twitter Like us on Facebook  Subscribe on iTunes | Android | Google Play Music | Stitcher | YouTube | RSS Feed | Also check us out on Florida Geek Scene and We Be Geeks Network  You can catch us on Tuesday and Thursdays on Undiscovered Rock Radio! You can also check out Nathan's website Theme Park Bound