North Star Podcast

Rob Henderson is one of my favorite up-and-coming writers. I like him because he's one of those people who doesn't fit into a category. He's a Ph.D. candidate in psychology, but I met him in a book club about technological stagnation. He's spent years in the academy, first at Yale and now at Cambridge, but most of his influence comes from his online writing. Most of all, he's interested in human nature. In particular, psychology, status, and social class. Those interests come from his background. During his childhood, he bounced around between foster homes in California. After working as a busboy, a dishwasher, and a supermarket bagger, he joined the Air Force at the age of 17. After his enlistment, he ended up at Yale and now, Cambridge. Please enjoy my conversation with Rob Henderson.

This week, I have two guests. Both are affiliated with Synthesis, a new kind of online school where kids learn through games and simulations. One is Chrisman Frank, the CEO of Synthesis. The other is Ana Lorena Fabrega, who is their Chief Evangelist. Here's the backstory: A few years ago, Elon Musk asked the co-founder to start an experimental school with him at Space X. The goal was to develop students who are enthralled by complexity and solving for the unknown. Synthesis was the most innovative learning experience from that school and spun off into its own company. In full transparency, I'm an investor. This episode presents a vision for the future of childhood education, enabled by the Internet. Please enjoy my conversation with Ana Lorena Fabrega and Chrisman Frank.

Ash Fontana is an entrepreneur, investor, and author. As an entrepreneur, he was only of the early employees at an online investing platform called AngelList. From there, he became the Managing Director at Zetta, the first investment fund focused on artificial intelligence. Now, he's the author of the AI-First Company. This conversation is about that book. Ash says that AI-First companies are the only trillion-dollar companies, and soon they will dominate even more industries, more definitively than ever before. But we don't just talk about the book. We also talk about health, continental philosophy, and Ash's obsession with bicycling. Please enjoy my conversation with Ash Fontana.

My guest today is Li Jin, the founder and managing partner at an early-stage venture capital firm called Atelier. She's known for her extensive writings about the Passion Economy. Her essays explore how people can make a living from their passions and creative skills. All of her writing is filtered through the lens of consumer startups and the technology industry. In this episode, we explore Li's perspective on the future of the creator economy. We talk about what it'll take to build a middle class for creators and how platforms should enable creator monetization. But then we venture beyond the world of work and discuss the novels of Jane Austen, what Li learned by growing up in Pittsburgh, and why she thinks social media and content creation are valuable pursuits. Please enjoy my conversation with Li Jin. Show Notes: 2:37 - How do content creators get users to migrate platforms and engage in unfamiliar apps? 5:44 - Why is some digital content more consumable than others? 13:07 - What is the driving force behind Li’s background in English literature? 17:34 - Why Jane Austen is so incredibly important to the world of modern creatives 21:56 - What has contributed to the alienation of gig workers in modern economy? 24:57 - Where does Li Jin’s technological optimism stem from? 28:32 - What is an “Angel Investor”, and how do they influence the modern world of content creation? 32:55 - What is the difference between an artist and a creator? 37:44 - How has the modern market created space for content creators? 42:19 - What causes creative burnout in the world of content creators? 50:01 - What are the implications of viral fame in the modern world of content creators? 57:46 - Which aspects of traditional and non-traditional education were most impactful on Li Jin? 1:08:55 - What are some things that both successful and aspiring content creators often misunderstand about the industry 1:14:20 - What are some of the parallels between the worlds of writing and investing? 1:18:08 - How Li Jin embodies the spirit of a malleable fate

My guest today is Zena Hitz, a tutor at St John’s and the author of an excellent book called Lost in Thought: The Hidden Pleasures of an Intellectual Life. Her book explores the meaning and the value of learning for its own sake, through images and stories of bookworms, philosophers, scientists, and other learners, both fictional and historical. That’s the jumping-off point for this episode. We also talked about the relationship between religion and the Liberal Arts, why studying the Liberal Arts has become so unfashionable among average people, and how an essay about Oedipus Rex inspired her to become an intellectual. ____________________________ Show Notes 1:37 - What about Oedipus Rex grabbed Zena's attention and inspired her to pursue intellectualism. 7:05 - What Zena sees as a "good" question in an intellectual frame, and why good materials can get you to them more easily. 9:55 - Why the most profound questions won't show up at the beginning of your inquiry, and how the common person's depth of inquiry has seemed to dwindle since the past. 13:19 - How Zena maintains her attention reading books when it is so easy to be distracted. 17:00 - Why it is decadent, complacent, and undermining to ourselves and our community to pursue education only in what will get us work. 23:53 - How people pursued lifelong learning in the past and why it's even more viable of an option today. 28:07 - What Zena hopes to give to the world at large through her work. 33:51 - How the monumental shifts in wealth and inequality have hindered people's ability to contemplate ideas they deem important. 36:20 - The differences in solitary and communal efforts to contemplate intellectual topics. 39:40 - Why we shouldn't be consuming books, but rather engaging directly with them. 44:03 - Why Zena believes that the idea of a patriarchal or caucasian canon is a myth. 49:02 - How education is a means of training your mind while simultaneously freeing it. 53:04 - The affinity between the liberal arts and religion. 55:11 - Where Zena learned how to write and why she has trouble writing if she doesn't have an audience. 58:42 - How to use writing to improve your thinking. 1:01:30 - Why St. John's has deliberately set itself apart from research universities. 1:05:33 - The crisis in Zena's life that kicked off her political thinking and essays, and why she believes that our current institutions are becoming increasingly disconnected from our humanity. 1:13:23 - What brought Zena to religion when there is a historic amount of people leaving it.

I have two guests today: Tiago Forte and Will Mannon. Tiago is my business partner and the creator of an online course called Building a Second Brain. The two of us record a podcast like this every year to reflect on what we’ve learned about the online education industry. And this time, we invited our Director of Student Experience: Will Mannon. Will oversees all aspects of the student experience with the exception of curriculum design. He’s at the frontier of thinking about live online learning, from how assignments should be delivered to how live sessions should be structured. ____________________________ Show Notes 3:21 - Why hiring your first employee is one of the most important steps you'll take in your business. 5:38 - How sharing a workforce and resources with another business or entrepreneur can help fast-track personal and professional growth. 11:00 - How running an online course is like organizing a music tour. 13:30 - The role of the alumni mentors in Tiago's courses, and how they have changed from his first to his most recent cohort. 17:16 - What different mentors can bring to the table and why the differences between them all brings strength to the program. 21:03 - Why giving as many people as possible the ability to lead allows much more effective learning for everyone. 25:04 - The nature of burnout and why creatives are so prone to experiencing it. 31:04 - Discovering the right size for a cohort and how to scale effectively. 37:13 - How to help students find each other and make meaningful and lifelong connections with each other. 40:28 - The "beer mode" and "coffee mode" of productivity. 44:32 - How to increase your focus by never giving yourself enough time. 51:02 - Why David and Will organize Write of Passage to have attendees "come for the ideas and stay for the people". 56:23 - Why running a course should be about empowering leadership in students, not in building dependence on the teacher. 1:02:33 - Why the element of shock is so fundamental to deep learning. 1:06:43 - How friendship can come so readily out of hardship and pain. 1:11:33 - The unusual growth of David and Tiago's online brand this year and what sparked it. 1:14:45 - Why writing a book summary for Tiago is so integral in internalizing the information and the message contained within it. 1:24:22 - What hands-on education and perseverance in the face of extreme difficulty can teach us that traditional education never can. 1:32:30 - What we can learn about education from businesses and markets outside of the educational sphere. 1:36:33 - Why success in a new business should not be focusing on competition, but on radical differentiation. 1:39:23 - The importance of finding your community online and curating it to inspire and inform you.

My guest today is Gagan Biyani, the current CEO of an education startup (where I’m both an investor and an advisor) that helps teachers run Cohort-Based Courses on the Internet and has students from around the world. Gagan also founded a multi-billion dollar online education platform called Udemy. Afterward, he founded Sprig, a food delivery platform that grew to a nine-digit valuation but eventually failed. So today, he has the distinct pleasure of being both the founder of a unicorn and the founder of a massive failure. In this conversation, we talk about what he’s learned playing the Silicon Valley startup game. Then, we talk about our visions for the future of the online education industry, and how he's learned so much about cooking and restaurant operations. Please enjoy my conversation with Gagan Biyani. ____________________________ Show Notes 2:11 - How Gagan comes up with and develops his startup ideas. 7:38 - Why Gagan believes that the market is the best thing we have, but that it is still deeply random and flawed. 10:14 - The lessons we should be learning from Silicon Valley and what people in Silicon Valley need to learn themselves. 14:51 - The dogma and necessities of startups that Gagan has seen in Silicon Valley that are proven to be untrue. 21:17 - How the duality of total rationalization and going with your guy fits together. 25:18 - How the "soul" plays into optimizing our lives and why Gagan sees the future of human connection. 30:50 - What inspired Gagan to become fascinated and so knowledgeable about food. 35:58 - What changes when making food at scale and why recipes don't multiply easily. 43:01 - What Gagan looks for in determining whether a restaurant is worth going to. 47:41 - How lifelong learning changes the way you see the world. 52:22 - Why the way a company does one thing will show you how it does everything. 56:17 - Why knowledge should be something that is shared, not something that pushes people away. 1:02:54 - How the classical cohort-based learning model has evolved on the internet. 1:09:35 - How colleges and traditional institutions are adapting to the new learning paradigm. 1:11:03 - What Gagan envisions in an ideal future-thinking educational company. 1:22:45 - How cohort-based courses can be improved and where Gagan saw these flaws in his own and in other courses. 1:26:17 - What in Gagan's early life made him so driven and motivated to do what he wanted to do. 1:36:51 - Gagan's trip to the Amazon, and what he learned from the indigenous tribes that he visited. 1:43:01 - The infantilization of different ways of life, and why it is a more ethically dense topic than people realize.

My guest today is Trevor Bauer, who is arguably the very best pitcher in Major League Baseball. In 2020, he had the lowest Earned Run Average of any pitcher and won the National League Cy Young Award, which goes to the top pitcher in the game. I wanted to interview Trevor not only because he's an excellent pitcher, but because he takes a radical approach to the game. He's a physicist and a scientist. A scholar and an entrepreneur. And you don't find that combination very often. Furthermore, he might be the most polarizing figure in baseball. Some people love him; some people hate him. But every fan has an opinion on him. Off the field, he's the founder of Momentum, athlete-driven media company that uses storytelling to connect athletes and fans. To build it, he started a podcast and a YouTube vlog where he talks about pitching mechanics and what it's like to play professional baseball. Personally, this was one of the coolest episodes I've ever recorded. I grew up as an avid San Francisco Giants fan, and I still remember getting to the field early to get autographs and catch baseballs during batting practice. This interview would have made little 8-year old David proud, and I'm lucky to share it with you today. Please enjoy my conversation with Trevor Bauer. ____________________________ Show Notes 2:18 - How Trevor would change the way baseball is marketed and to whom it should be pitched. 5:45 - Why updating the game for a modern audience would be difficult, despite what Trevor believes would be a successful move. 11:23 - Why there aren't many unique fields like in San Francisco or Boston. 15:10 - How baseball is not being evangelized well by the people who could be doing it most easily. 19:51 - How general scientific literacy can and should be improved through sports. 23:28 - What it takes for Trevor to scientifically design his pitches and then implement them in a game. 31:00 - The business of baseball, and how Trevor has learned to maneuver its quirks and difficulties. 37:13 - If could choose anybody, who else in the sports world and beyond Trevor would want to talk to. 42:15 - How Trevor looks into the future to superpower his game. 48:07 - The dangers of getting too in-depth in analyzing your game, and how it can hurt you. 54:43 - Why you should practice analytically and perform intuitively. 56:13 - What breathing techniques Trevor employs in his game. 58:18 - The different aspects of building a business and how Trevor is handling each element differently. 1:07:30 - Why Trevor's actual goals in his work and his game aren't covered by the media. 1:10:44 - How his father helped Trevor succeed in baseball by giving him the tools he needed to work hard.

My guest today is Nik Sharma, the founder of Sharma Brands and an advisor to companies like Judy and Cha Cha Matcha. Nik is one of my very best friends and my go-to person for all things commerce. Since we first met, we've spent hours exploring the future of marketing and commerce together and recorded this podcast to give you a window into what our conversations are like. We started with Nik's philosophy of launching Direct-to-Consumer brands. I particularly liked Nik's idea of "The Brag Bar" on landing pages, where you can use social proof to sell your products. We also spoke about managing relationships with influencers and finding the supply and demand equilibrium at launch. Towards the end, Nik and I talked about our process for turning conversations into articles, and the time he cold emailed Mark Cuban. Please enjoy my conversation with Nik Sharma. ____________________________ Show Notes 2:21 - Why Nik has the "world's craziest fridge" and how it helps keep him in the know on DTC brands. 6:29 - What marketing strategies Nik has found most successful for DTC brands. 13:31 - How brands can differentiate themselves in a world of emerging brands in already burgeoning markets. 19:25 - Nik's approach to launching a successful DTC brand and when to concentrate your advertising versus diversify. 30:19 - The role of A/B testing in building a brand. 35:43 - How influencers play into the big picture of marketing and why the "shaky video" effect is so successful. 42:12 - The selection and audition process of influencers in Nik's campaigns and how he chooses those he sees as the best for his brands. 45:52 - The costs and benefits of starting your brand through heavy promotion via influencers. 49:56 - How the process of rebranding Hint Water's bottle was performed and the qualitative process that got them to the bottle you see today. 57:27 - The metrics and methods Nik uses in his development of marketing strategies with his brands. 1:05:19 - What Nik looks for in a great landing page, and why all landing pages should be easy to read for everybody from a 12-year-old to a drunk person. 1:10:07 - What UGC is and why Nik thinks it is so underrated by marketing teams. 1:13:31 - The different marketing funnels and when you should use each one. 1:17:09 - Why Nik creates landing pages for fake products and makes them live on the internet. 1:22:56 - The importance of having great merch for your brand. 1:26:22 - What about internet culture makes collaborations so successful and popular. 1:34:05 - How somebody can convert a large personal following into sponsorships and meaningful collaborations. 1:35:46 - How new brands should position themselves when huge players like Amazon are in the same space. 1:44:01 - What happened when Nik cold emailed Mark Cuban and how he got an almost instant response. 1:50:46 - How David and Nik collaborate to develop, write, and publish the articles they make. 1:56:14 - Why Nik doesn't sweat the details of his personal brand that much.

My guest today is Kevin Kelly, who co-founded Wired Magazine in 1993 and served as its Executive Editor for the first seven years. As one of the most important futurists of our generation, he's published a number of books including The Inevitable, What Technology Wants, and New Rules for the New Economy which is my favorite one. Coolest of all, he's also a founding member of the board of the Long Now Foundation, a non-profit devoted to encouraging long-term thinking. We discussed the Long Now Foundation at the end of this episode in a conversation about what it means to be a good ancestor for future generations. A couple of things stood out from this conversation. First, I like how Kevin focuses on clarity above all else whenever he writes. He sees himself as a great editor, and writing is the process by which he discovers what he's thinking. Second, we build off the ideas of Marshall McLuhan who was the founding saint of Wired Magazine. Through McLuhan, we explored Kevin's Christianity, how screens are shaping consciousness, and how our technologies have a gravitational life of their own. Please enjoy my conversation with Kevin Kelly. ____________________________ Show Notes 2:22 - Exotropic energy and how Kevin uses it to explain the negative entropy we see throughout the universe. 6:24 - Why California has become the world hub of extropy. 10:33 - The transition from the written word to text and screens and how it affects our psyche. 15:27 - What made Marshall McLuhan's writing so paradoxical and engaging. 18:34 - How science fiction has usurped religious teachings as the modern leader of theological thought. 24:06 - Why our limitation as seeing the future only "through the rearview mirror" is driven by a disease Kevin calls "thinkism". 31:25 - How the Amish have utilized an evidence-based method in their adoption of new technologies. 44:46 - Why technology that we create will always be weaponized in the end. 49:01 - Why Kevin believes that the evidence shows the increase of accessibility of and power in technology has not correlated with our ability to harm. 53:15 - How moral progress is a natural byproduct of technological progress. 57:26 - Why Kevin sees a fundamental transformation in how Maslow's Hierarchy of Needs is thought about and utilized in people's lives. 1:05:25 - Why Kevin's futurology is much closer to simply noticing the present that it is divination. 1:15:20 - How moving away from improving everything's efficiency is against the very things we desire as humans. 1:23:35 - Why writing for Kevin is nothing but a means to an end to discovering his thoughts. 1:29:43 - How thinking with 'the long now' can help us become better ancestors and leave a better world for the future.

Will Ahmed is the Founder and CEO of WHOOP, which has developed next-generation wearable technology for optimizing human performance and health. I found him through an excellent interview he hosted with Rory McIlroy, a winner of four major championships who was once the #1 golfer in the world. Then, once we started talking, he told me about the group chats he shares with other top golfers like Justin Thomas. The man is obsessed with health technology like nobody I’ve ever come across, so conversation topics range from the business of wearables, to the challenges of tracking accurate data. Then, he shared his philosophy for why sleep and recovery are a more important data point for an athlete than exercise and stress. My favorite part of the interview was hearing about Will’s philosophy of management, and why he tries to hire people who have high intensity and high humility. Please enjoy my conversation with WHOOP CEO Will Ahmed. ____________________________ Show Notes 2:15 - What data Will wishes he could magically track for his users and why it could drastically improve their health. 6:30 - How breathing exercises, mindfulness, and meditations help your heart rate. 11:05 - Why WHOOP has found so much success in helping golfers and baseball players over other sports. 13:20 - What Will remembers as his favorite conversations with athletes. 16:24 - Why it's so hard to capture accurate sleep cycle data. 20:43 - Why teams on average get less sleep at an away game than at a home game. 23:38 - The limits of what can or can't and what should or shouldn't be tracked. 26:38 - How WHOOP separates itself from the larger players in the health market. 31:08 - Why Will believes strongly that the branding of WHOOP products aids in developing a person's own brand. 34:30 - Why not developing your own hardware to go with your software can be detrimental to your overall design. 41:41 - The future of informed coaching using WHOOP and their membership services team. 43:19 - Why WHOOP started out as a brand-focused company, and why it was so important to go about it this way. 45:38 - What it was like playing Augusta National. 49:00 - How to know when to operate analytically versus intuitively. 56:43 - The key to being different, and why you should always be asking your customers what their problems are, not what their solutions are. 1:01:16 - What piece of advice that Will would give his younger self in the past.

My guest today is Seth Godin, the author of nineteen international bestsellers that have been translated into more than 35 languages. My all-time favorite is Purple Cow, which I discovered in college and became my nickname. This is my second interview with Seth, who has published an article every day now for more than a decade. If you want to be a prolific creator, Seth is one of the best teachers you can possibly find. This interview is all about his writing practice. Seth calls himself a “professional noticer” so we talked about how he finds and validates new ideas. On the topic of shipping creative work, we spoke about the root of imposter syndrome and why Seth likes writing on airplanes, and how his book The Practice was inspired by one of his workshops. We also discussed his tactics for effective public speaking, how to improve the education system, and what we've learned by running online schools — his AltMBA and my Write of Passage. ____________________________ Show Notes 2:32 - What inspired Seth to start his now 20+ year daily writing streak. 6:00 - The root of impostor syndrome and why Seth thinks it's not only normal but just true. 8:14 - The evolution of an idea or a blog post into a full book. 10:50 - Why it is important to ship as a creative worker and what it means to ship your content. 13:50 - Why certain conditions make it easier for people to create than others. 16:59 - What Seth learned about creating inspiration from hard science fiction writer Isaac Asimov. 20:22 - How Seth developed his unique video style and the unique way he utilizes his slides. 23:25 - What the best future of education looks like to Seth and why he believes in the dream of public schooling. 29:48 - Why the standard lecture model of the current education system is missing the point of education. 33:53 - The difference between online education and online learning and why Seth sees them as almost polar opposites. 39:35 - Why there must be space for surprises in online learning. 41:31 - How capitalism has caused certain schools to flourish less through their educational prowess and more as a pipeline to various jobs.

My guest today is Dave Nemetz, the Founder of Bleacher Report, which was one of my favorite media companies as a kid. During his time there, Dave oversaw video, business development, and business operations. He helped grow the audience to more than 40 million monthly unique visitors before selling the company to Turner Broadcasting in 2012. Today, he is the Founder of Inverse and the Executive Vice President of Bustle Digital Group where he leads growth and business strategy for Inverse, Input, and Mic. The conversation topics in this episode fall into three buckets: personal principles, business principles, and the state of the world. We spoke about what it's like to lead your company through a merger, why you can think of media businesses like a supply & demand equation, and one of Dave's favorite quotes from Hunter S. Thompson: “When the going gets weird, the weird turn pro.” My favorite part of the interview was hearing about a band called Phish, which Dave has seen in concert more than 200 times. That section kickstarted a whole conversation about the brand-building tradeoff between being welcoming to new fans and serving die-hard fans. ____________________________ Show Notes 2:31 - What inspired David to get started on the Bleacher Report and why he was drawn to it as a project. 6:24 - Why the desire for a different kind of sports coverage took so long to take off and why other companies didn't get into it earlier. 9:06 - Why sites like Bleacher Report find their niche, even with an abundance of content being created all of the time. 12:46 - The implicit versus the explicit side of finding your niche and exploiting it in the market. 15:14 - What David has learned about building a brand and serving your customers from his favorite band, Phish. 20:12 - How businesses can both serve their die-hard fans and not neglect their newcomers. 27:05 - The arrival fallacy and why selling Bleacher Report to Turner wasn't as exciting as it may have looked on the outside. 31:36 - Why David believes that a fervent drive and passion to achieve goals is a double-edged sword. 34:26 - What most people don't know about managing a business during a buyout or a merger and why it was so difficult for David to handle. 42:54 - How the world of advertising in the early 2000s hadn't seemed to change much from the era of "Mad Men". 52:38 - Why the "the geeks won" and why David is super happy about it. 57:13 - How David has oriented his recruitment and retention strategy in his media brands. 1:05:43 - What the "career elevator" is and why David was determined to create it for himself. 1:10:29 - Some of David's favorite quotes, and why one of his core philosophies is to "enjoy your sandwich".

Newsweek Magazine once called Rabbi Wolpe the most influential rabbi in America. He is the Senior Rabbi at Sinai Temple in Los Angeles and he's the author of eight books including one about King David and another gem called Why Be Jewish? I don't remember the last time I enjoyed preparing for an interview so much. I'm named after King David, but until this interview, I hadn't explored the history of my name in more than a decade. This interview touches on various parts of Judaism including how rabbis should interpret the Bible, what we can learn from King David, and how Judaism anchors us when a loved one dies. There were two parts that I'll always remember. The first was a discussion about the concept of aloneness in Judaism. On one hand, the book of Deuteronomy says: “It is not because you are the most numerous of peoples that I have set my heart upon you and treasured you—indeed, you are the fewest.” On the other, community is everywhere in Jewish life and the first thing God called not good in the Bible is loneliness — “It is not good for the man to be alone (Gen 2:18).” Secondly, I enjoyed our conversation about repentance in the Jewish faith and how you must repent after a loved one dies but also have to stop after 11 months. If this conversation interests you, I recommend his sermons on YouTube and the book I mentioned before called: Why Be Jewish? ____________________________ Show Notes 3:15 - How Jews have uniquely struggled with their identity and the way they present themselves. 5:56 - How the heroes of the Jewish culture have changed over time and what makes them heroic. 8:26 - What makes Judaism different from Christianity. 11:39 - The interpretation of the Bible and how Judaism reconciles its eternal nature with the changing interpretations over time. 14:43 - The most meaningful traditions in Jewish people's lives and why Rabbi Wolpe sees the Jewish mourning rituals as some of the most powerful. 19:24 - Why many Jewish people converted to Buddhism in the Modern era. 22:11 - Why the decline of religious people throughout the world may indicate a decline in art being created. 25:52 - The power of a culture of togetherness and why Rabbi Wolpe believes that Judaism was unique in being welcomed to America with open arms. 29:02 - Yom Kippur and why Judaism uniquely holds a ritual of confession not only for each person's sin but also from the sins of the Jewish people. 31:01 - One of the biggest differences between classical Christianity and Judaism. 34:35 - What separated Maimonides from other prominent Jewish philosophers. 36:39 - What Heschel meant in that the collapsing of space is seen as the collapsing of time. 38:45 - Why we should always take care of our "big rocks" first before anything else. 44:56 - Why modern life and technology can cause people to lose touch with the transcendent and the world around us. 49:09 - Why Rabbi Wolpe feels that introducing children to religion at an early age is important to their understanding of it. 54:20 - The origin of the Jewish style of dry humor. 1:00:05 - What about King David drew Rabbi Wolpe to study him so deeply. 1:04:34 - Why it's impossible to change the age of a boy's transition into a man through a bar mitzvah. 1:07:01 - What it means to Rabbi Wolpe to be a Rabbi.

My guest today is Joseph Henrich, a professor at Harvard and an expert on the evolution of human cooperation and culture. I am a big fan of his book, "The Secret of Our Success" and he just published a new one called the Weirdest People in the World about people who fall under the acronym WEIRD: Western, Educated, Industrialized, Rich, and Democratic. Through his research, he explains culture's role in evolution. He shows how evolutionary theory can help us learn, innovate, and share knowledge. We begin this episode by talking about the role big Gods play in cultural evolution. Then we talk about the time Joe spent living with small-scale societies in rural Peru and Fiji. He talks about how he learns the language, plans the trips, and assimilates into societies so he can study them. Towards the end of the podcast, we talk about what economists can learn from anthropologists and the evolution of attraction. My favorite part of the conversation was learning about the tradeoffs between having an open or closed society, and how those factors contribute to innovation. Please enjoy my conversation with Joseph Henrich. ____________________________ Show Notes 2:06 - How the role of God has evolved over time and why bigger and bigger Gods have become the norm. 4:50 - Why acting as a third party for people made Gods culturally and socially so much more important. 8:36 - Marriage across cultures and religions and why they diverge sometimes wildly from what Western culture considers "normal". 13:44 - Why many religious restrictions that created the Western norm of a nuclear family also set up the stage for heightened individualism. 16:58 - How and why social safety nets transitioned from kin-based institutions to the states and governments. 18:46 - What surprising similarities and differences Joe saw between Americans and the Machiguenga of the Peruvian Amazon. 22:22 - The role of humor in enforcing social norms, why Joe thinks it is absolutely universal, and the other universal ways trust is built-in communities. 28:35 - How narcotics and psychedelics are utilized in different cultures and the way their roles differ. 31:20 - Why cultural imitation does not always yield positive outcomes. 33:11 - How the introduction of agriculture changed family relationships and culture. 39:36 - The biggest takeaways Joe got from Guns, Germs, and Steel. 43:28 - Why Joe believes that religion is innate in human beings. 50:31 - The possible implications of losing rituals that for millennia have brought families and clans closer together. 52:24 - What the clock and a universal time have done to human psychology. 1:01:16 - What the collective brain is and why it is so prevalent throughout creative booms in history. 1:04:55 - How the proliferation of information helps and hurts creativity, and why the internet hasn't had the impact people thought it would. 1:08:26 - How information is affected by biases and manipulation and why humans are so susceptible to them. 1:11:39 - How the technology, institutions, and tools we use affect the way that we think. 1:15:12 - Why learning disabilities should not be looked at as purely negative and the benefits that cognitive diversity brings to humanity. 1:19:00 - The way gossip in a society helps define the collective philosophy of its people. 1:21:07 - How imitative education is currently at its peak and what doors it opens for people around the world. 1:24:36 - Why rituals and multiple gods were so common in the past and are so uncommon now. 1:28:40 - How Jon would alter the current research practices in the social sciences on "WEIRD" people and why. 1:31:39 - Why certain assumptions about humans are actually specific to a region or population, and why they don't represent humanity as a whole. 1:35:10 - Why the top-down lecture model is not serving education as well as it should, and why it shouldn't be replaced completely by Youtube. 1:39:20 - The selective physical and cultural evolution of certain populations and why it happens the way it does. 1:42:12 - What Jon finds to be the most interesting elements of culture to study and why. 1:45:33 - Why Jon's aerospace engineering degree is so valuable in his anthropology career. 1:47:41 - The problem with focusing solely on models in research and studies. 1:53:20 - Why humanity seems to be stagnating in intelligence but rocketing upward in cultural development.

My guest today is Grant Sanderson, the man behind one of the world's largest math-focused YouTube channels: 3blue1brown. He has more than 3 million subscribers and his videos have been watched more than 150 million times. Before making videos he studied math and computer science at Stanford before working at Kahn academy. On YouTube, he brings a visuals-first approach to math. Every video starts with a narrative or storyline. Then it revolves around imagery that illuminates the beauty of mathematics. Topics for his videos include linear algebra, neural networks, calculus, the math of Bitcoin, and quantum mechanics. This episode begins with a conversation about the culture of mathematics. We talk about ideas like prime numbers, the Twin Primes conjecture, and pop culture's role in advancing mathematics. Later in the episode, we talk about mathematical constants and the rate of progress in mathematics. Then, we close by talking about Grant's process for writing scripts, note-taking, and researching ideas for each episode. ____________________________ Show Notes 2:14 - Why everybody loves prime numbers so much and what makes them so special. 4:56 - What was initially so interesting about math for Grant and why he didn't end up going into a more formal researching role. 8:23 - Why Grant is getting increasingly more fed up with math that doesn't even try to be associated to reality. 11:36 - The usefulness of "useless" knowledge and why spending an afternoon solving a math puzzle is so satisfying. 18:42 - What is driving the accelerating progress of the entire field of math. 22:19 - How Gödel's famous theorem attacked the fundamental structure of math and changed the way mathematicians think about it. 27:31 - The unappreciated universality of math and why knowledge and interest in math by the public is higher than ever before. 31:49 - Why Grant believes that attention spans aren't getting shorter and why the evidence is so strong. 35:43 - The importance of the principles of symmetry and creating meaningful names in math. 40:58 - Why Grant believes that distraction is key to creative work. 44:33 - Brand-building and why Grant believes it is important for anybody looking to build trust in their products. 47:40 - What videos are the hardest for Grant to produce and why. 49:31 - Building the intuition of teaching through a non-interactive medium. 54:42 - What was most unexpected to Grant about working in the field of mathematics. 1:00:19 - Where Grant gets his video ideas and how his script-writing differs from video to video. 1:05:31 - How an idea evolves from sketches and drawings into a logical coherent video. 1:07:35 - How college education in math can be improved and why it can be unnecessarily hard for students in that program. 1:11:42 - The possible implications of the collision of mathematics and computing in pure math research. 1:14:32 - The story behind some of David's favorite quotes in Grant's videos.

My guest today is Eric Jorgenson, a Product Strategist at Zaarly and the author of the Almanack of Naval Ravikant: a guide to wealth and happiness. The book collects and curates Naval's wisdom from Twitter, podcasts, and essays over the past decade. Naval is the founder of Angel List, an angel investor who has invested in companies like Twitter and Uber, and the man behind one of the most popular Twitter accounts in the world. He's known for his thoughts on startups, investing, crypto, wealth, and happiness. This is a conversation about that book. We began the conversation talking about Multiply by Zero Effects, which comes from a short e-book Eric wrote called Career Advice for Uniquely Ambitious People. Then, we moved onto the Almanac. We talked about the differences between Charlie Munger and Naval Ravikant, building specific knowledge, and how operating companies influenced Naval's philosophy of life. At the end, we also jammed on what Naval would say to the owners of Joe's Bar-B-Que, Eric's favorite restaurant in Kansas City. ____________________________ Show Notes 2:28 - Why Eric wrote his new book, and what he regrets not putting in it. 6:15 - What Eric thinks Charlie Munger and Naval Ravikant would disagree on most. 9:34 - Why people like Naval and Munger often give advice as the "Iron Prescription" to solve a problem or learn in a field. 12:13 - Why so many Silicon Valley entrepreneurs were on track to be an academic but then split off. 13:20 - What entrepreneurs can learn from how comedians develop their voice and leverage their following. 15:57 - What knowledge Naval has that is unique only to him in his field. 19:36 - How to maximize leverage and value as an entrepreneur and in your career. 23:26 - What defines a startup, and what Eric has learned from Nivi through his writings on VentureHacks. 25:37 - How Naval uses Twitter as a repository for his ideas and findings and as a forge to test them out. 31:22 - Naval's view of hard work and how it has changed over time. 34:40 - Why it took multiple rereadings of his book and years of observation and experience for Eric to start fully understanding Naval's idea of "productize yourself". 36:11 - What about Eric's own book did he start to resent by the end of creating it. 40:01 - How the message of the book changed as Eric was compressing and cutting the source material down. 43:10 - Why Eric could not have done this book without loving Naval's work as much as he does. 46:19 - What advice Naval would give to Eric's favorite restaurant, Joe's Barbecue. 48:45 - Why David has never forgotten Eric's comment on how "owning a home is a never-ending battle against water" and what he means when he says that. 50:20 - How writing this book gave Eric "more clarity, confidence, and peace through all aspects of life."

Morgan Housel is a partner at The Collaborative Fund and a former columnist at The Motley Fool and The Wall Street Journal. He's the author of The Psychology of Money, where he shares 19 stories about the strange ways people think about money and teaches you how to manage it. I revere Morgan's writing, and this episode was my chance to finally ask him about how he writes so well. We talk about why listening to loud music helps Morgan think, lessons from his favorite non-fiction writer, and why you should start stories at the moment when you're being eaten by a bear. We also talk about the rise of intangible assets in the economy, why the American economy shifted in the 1970s, and how investment strategies have changed over time. ____________________________ Show Notes 2:00 - How the economy is changing, and why the edge in technology is going up while the edge in finance is going down. 6:38 - How the rise of intangible assets is distorting our view of the economy. 9:58 - The benefit of being slightly underemployed and why perceived "leisure" is so important in Morgan's career. 14:12 - What differed between what Morgan thought he would do as a parent and what he actually does. 15:35 - How the 1970s and 1980s fundamentally shifted the economy and culture of America. 20:22 - The three most important factors in really understanding the economy and whether truth or coherence is more important for social stability. 24:35 - How Morgan gets away with almost no collection or organization in creating his work. 29:58 - Why writing for yourself as a way to better understand your gut feelings will always pay off. 31:46 - How and why Morgan searches for the obvious things nobody pays attention to. 34:00 - Why some colleges are here to stay and others are not going to last according to Morgan. 40:11 - The most important things about writing that Morgan has learned from former and current workplaces. 42:24 - The two articles that Morgan is most proud of writing. 45:46 - What it means that people spend more money on the lottery than movies, music, video games, sporting events, and books combined. 49:06 - Why there aren't enough good books about how to write well. 52:15 - A writer that Morgan wishes more people would read their work. 54:32 - How the Ben Affleck speech in Boiler Room inspired Morgan to work in finance. 56:10 - The most difficult part about writing his most recent book.

My guest today is Claire Lehmann, the founder and editor-in-chief of Quillette, a for-profit online magazine that publishes essays on topics like politics, science, and academia. We started our conversation talking about Quilette's business model and the niche it occupies on the Internet. Then, we moved on to societal topics like the longevity of bureaucracies, the pros and cons of standardized tests, and what Claire would change about childhood education. ____________________________ Show Notes 1:31 - Why Claire believes being a for-profit instead of a non-profit gives her and her company more freedom. 5:32 - What Quillette has learned through publishing so many submitted articles over the years. 10:15 - The relationship between free speech and innovation. 13:12 - What we can learn from how Russia handled scientific experimentation and their lack of freedom to critique it. 15:08 - Why one of the biggest flaws Claire sees with higher education is that it seems necessary for people to go. 20:17 - How higher education is only creating academics and not lifelong students. 23:32 - Why organizations may have a lifecycle and how it plays into the problems that come with their extended growth. 29:45 - Why Claire believes literacy in subjects like psychology and statistics is massively underrated. 34:55 - What Enlightenment-era values are justly held in high regard, and which we may need to reconsider in the modern age. 40:54 - The historical reasons why intellectualism is not a strong value in Australia. 43:46 - What Claire has learned about childhood education through her time at Quillette, and why she believes younger children need to spend most of their time learning facts. 51:04 - Why standardized testing is beneficial for children from underprivileged families. 55:37 - What Claire believes to be her strengths in both her personal and business life. 58:12 - What about the book "The Custom And The Country" makes Claire love it so much. 1:01:42 - What it may mean for our brains as we possibly move into a "post-literate" society. 1:05:03 - Claire's favorite articles she's ever hosted on Quillette.

My guest today is Balaji Srinivasan, an angel investor and entrepreneur. When it comes to the future, he's the single most creative person I know because he's so technical, innovative, and polymathic. Talking to him is an experience unlike talking to anybody else, which I tried to replicate in this conversation. A little bit about Balaji. He's worked as the Chief Technology Officer at Coinbase and a General Partner at Andreessen Horowitz. In the world of academia, he holds a BS/MS/PhD in Electrical Engineering and an MS in Chemical Engineering, all from Stanford University. He's also taught at Stanford, where his online course has reached 250,000 students worldwide. This episode is a whirlwind through Balaji's interests. We started by talking about his production function. We talked about what holding all those degrees from Stanford taught him about learning, how he identifies talent, and what building and selling two companies for more than $100 million taught him about management. We also talked about his interests in genomics, how to reverse aging, and why living forever is the ultimate goal of technology. At the end, we built off the ideas I talk about in my online writing school called Write of Passage to talk about his plan to fund online writers with a project called MediaFund. ____________________________ Show Notes 2:42 - What Balaji learned about how to learn from his extended time in academia and why he doesn't read the instructions until he has to. 4:21 - Why knowing philosophy and history is so integral to starting a successful company. 6:54 - Why Balaji thinks we are severely underutilizing the collaborative potential of the internet. 12:45 - How remembering references to knowledge instead of the knowledge itself gives Balaji a better way to argue his points. 13:47 - Why searching for people who are "hungry and can teach us something" serves everybody who is involved very well. 19:39 - The "tour of duty" and how to create a great strategy for developing and managing yourself and your team. 24:25 - The movement from a centralized century to a decentralized century and why Balaji feels the future is moving more towards his lifestyle. 31:19 - How technology hyper-deflates the market of everything it touches. 38:23 - How the past is wrapping back around to the future and how the evolution of education is leading the way. 44:49 - Why abstraction means progress as a culture up to a certain point and can become harmful beyond that. 48:57 - How to optimize your information diet to make you smarter, more effective, and more honest about where you spend your energy. 54:07 - The future of online education and why it doesn't end with Wikipedia. 59:32 - New ways to look at incentive structures for writing and how it inspires technological and social growth. 1:04:27 - How to bridge the gap between Hollywood, big data, and education. 1:12:43 - The future of the internet and why the pseudonymous economy seems likely to Balaji. 1:15:04 - How we can use a "crypto oracle" to create an unfalsifiable history of our digital information. 1:21:31 - Why a worldwide ledger of record is the future we need in an information-driven world. 1:26:59 - Why Balaji believes that the pinnacle and goal of technology is to help humans live forever. 1:32:50 - How to build a digital country through writing. 1:39:34 - Why genomics needs more attention from the general population and technology. 1:44:42 - Why writers will be the future of millionaires and billionaires.

My guest today is Nadia Eghbal, an independent researcher and the author of Working in Public: The Making and Maintenance of Open Source Software. She currently works on the writer experience team at Substack. She did a lot of her research at Protocol Labs where she studied the production and economics of open source. Before that, she worked on the open source team at GitHub. One of the core theses of her work is that open-source software projects don't have zero marginal cost. Maintenance can be expensive, even if the code itself is free to distribute. In this episode, we spoke about how sharing ideas on different platforms helps you express different sides of your personality, why GitHub is the center of the open source community, and what she learned running a grant program. Please enjoy my conversation with Nadia Eghbal. ____________________________ Shownotes 2:07 - Why the personal projects of a coder can unexpectedly turn into a massive public responsibility. 4:36 - The temporal nature of creating code aside from any other art form. 8:24 - How creators can become enslaved by their own systems. 12:37 - How Github differs from social media platforms, and why it might be that way on purpose. 14:54 - The similarities and differences of open source code and organized religion. 20:48 - How to efficiently externalize information to make more open source type projects possible. 24:29 - Why Nadia feels compelled to write everything down, even though to her it sometimes feels like a problem. 31:00 - How the bystander effect comes into play in the world of open source software development. 35:17 - Why Nadia believes that the way open source was started made it "set up to fail." 38:46 - The importance of granularity and modularity in maintenance, throughout people's personal and professional lives. 43:54 - What the consequences are to accepting code that causes problems downstream. 46:22 - Why Nadia chose to write and publish this book instead of going through the process of getting a PhD. 49:05 - What microgrants are, and how their different aspects play into research and development. 54:06 - How creative people can share their knowledge with each other better through story sharing. 57:28 - How Nadia focuses the scope of her projects from being too overly broad. 1:00:40 - The danger of thinking you ever know enough about any field that's not your own.

My guest today is Matthew Kobach, the Director of Content Marketing at Fast and the former Manager of Digital and Social Media at the New York Stock Exchange. Matthew and I met on Twitter, where he shares actionable strategies for building brands on Twitter, Instagram, and Facebook, and YouTube. He does it with a level of humor and honesty I’ve never seen in the social media industry. This episode is a deep dive into Matt’s philosophy of social media. We started by talking about his all-time favorite television commercials and how they inform his social media strategy today. Then we spoke about how paid and organic social media should influence each other and why Cash App’s cash giveaways are such a smart social media strategy. Please enjoy my conversation with Matthew Kobach. ____________________________ Show Notes 1:39 - Who has surprised Matthew the most with the success of their social media strategy. 4:22 - Why social media is undervalued by the majority of marketing agencies. 8:32 - Why marketing to the "wrong" audience is still effective advertising. 13:08 - Matthew's favorite TV commercial of all time and why remembering the product may not be super important. 19:39 - How good advertising realizes things about yourself you haven't yet discovered. 24:03 - What social media post has been most successful for Matthew. 29:37 - How Matthew leveraged social media to land his current marketing job. 35:49 - Why focusing on organic long-term social media marketing instead of short-term paid became Matthew's niche. 39:07 - The convergence of organic and paid advertising and why Matthew thinks it's so effective. 45:10 - How having a long time horizon on your marketing strategy can help increase organic growth. 49:40 - Why giveaways have been and will always be successful. 54:49 - The greatest marketing lesson Matthew learned from his dad. 56:53 - Matthew's greatest takeaways from Peter Thiel's "From Zero To One." 59:09 - Why a fundamental change of social media seems completely unlikely without one particular element. 1:02:34 - How writing has become Matthew's "one weird trick" as a social media marketer. 1:06:20 - Why Matthew believes that at the opposite of a good idea is another good idea and why the inverse is also true.

David Brittain is the CEO of Concepts, my favorite iPad app. It's marketed as a "flexible sketching" app and geared towards people in the early stages of the thinking process. I use it to visualize my ideas, many of which I share on Twitter and in long-form essays. People use the app for mind-maps, mood boards, sketch plans, designs, and illustrations. I particularly enjoy the screenshots of architects using the app to design buildings. On this episode, David and I talked about the business, marketing, and engineering aspects of designing an app. David talked about Concepts' position in the design world, and how it compares to ProCreate and Figma. He spoke about how changes to the App Store have influenced Concept's download numbers and finally, he talked about why trust is particularly important in remote work as compared to in-person collaboration. I'm a fan-boy of the Internet because of how it enables apps like this to thrive. Concepts has been profitable for years. Whenever I pick up the app, I feel like I have a professional-grade design app for the cost of a latte every month. Please enjoy my conversation with David Britton. ____________________________ Show Notes 2:20 - How the landscape of designing apps has and hasn't changed drastically over the years 4:19 - What and who David thinks about in his design process 7:32 - How remote work management is different from in-person 11:52 - The key to a well-functioning and efficient remote engineering team 13:26 - How David spends his days at work as a CEO 16:36 - What vector design is and their pros and cons in comparison to raster design 21:20 - David's view of the market, the design world, and his competition 24:34 - How Formula 1 driver Lewis Hamilton has inspired David and what he could learn from Lewis about marketing 27:37 - Why paid marketing is not something that David and his team have spent much time nor effort on 32:08 - What David sees as the biggest pain-points from a user perspective of his app and the solutions they've tried 35:46 - What makes a good beta tester or user to get feedback from, and David finds them 37:47 - Why David doesn't consider himself the right person for his position and why that has been an advantage for his company 40:05 - The death of the computer mouse and why sketching and drawing isn't going anywhere 44:48 - How the Concepts team approached the development of their app on different platforms 46:43 - The future of apps and why certain apps have taken off while others lag behind 53:13 - How a feature moves from an idea into development and into the hands of the end-user 56:54 - Why architects flocked to using Concepts when it came out and what makes it still popular today

  Tyler Cowen is an economics professor at George Mason University. He runs the Mercatus Center, which bridges the gap between academic ideas and real-world problems. He’s published a new post every day for the past 17 years on his blog called Marginal Revolution, where he writes about economics, arts, culture, food, and globalization. Beyond that, he also writes for Bloomberg and hosts his own podcast called Conversations with Tyler. Tyler ends every episode of his podcast asking about other people’s production function. How do you get so much done? What’s the secret sauce of all that you’ve accomplished? This episode is entirely devoted to that question. But this time, I’m asking Tyler. We started by talking about why there aren’t more Tyler Cowens in the world. Then, we moved to Tyler’s process for writing, such as choosing article topics and editing his work. Later in the podcast, we discussed Tyler’s process for choosing friends, why he would travel across the world to visit a new country for just ten hours, and what he’s learned from high-powered people like Peter Thiel and Patrick Collison.   ____________________________ Show Notes 2:40 - What Tyler considers his compounding advantage and where he got it from 5:56 - Why being born as an intelligent person is not as important as developing knowledge 8:23 - How Tyler maximizes the value of his consumption and minimizes the drawbacks 9:19 - What draws Tyler to the people he likes spending time with, and what he likes best about their friendship 12:33 - Why Tyler feels that the way he has lived his life has meant has not given anything up 15:35 - How the fundamentals of productivity came intuitively to Tyler 17:41 - Why Tyler writes in his particular style not by choice, but by necessity 22:19 - Why the things in Tyler's life that bind his output aren't what you think 24:06 - How to develop new ideas while staying focused on the subject and not getting tangled 27:36 - Why Tyler sees art as one of the most important and beneficial things you can spend your time and money on 32:41 - What writers can learn about inspiration and consistency from musicians and visual artists 37:16 - Why Peter Thiel has impacted Tyler so deeply and why Tyler believes he's one of the greatest thinkers of our time 40:30 - How Tyler is able to extract more from his reading than other people do 45:44 - How understanding most other people's intelligence is higher than his in most fields gave Tyler an edge over other thinkers 49:00 - Why Tyler sees a new visibility of talent in people and how he is using this visibility 55:24 - How Tyler constructs his interviews to maximize the freedom of his guests to speak freely on what they love 1:00:03 - How to develop skills as a teacher and where Tyler believes the strengths of a good teacher lie 1:03:34 - Why the novelty and beauty of visiting other cultures excites Tyler so much 1:07:18 - How Tyler makes the most out of his travels 1:13:32 - Why sitting in a suboptimal seat at a concert may give you worse sound but a better understanding of the music 1:16:55 - Why knowledge workers are often not motivated to improve their skills 1:20:48 - Why Tyler still responds to every email and loves it

My guest today is marketer and software engineer Patrick McKenzie, who writes mostly about software-as-a-service businesses. He currently works for Stripe as a writer and an overall software business expert. I remember when I signed up for Stripe's Atlas program to incorporate my LLC, almost all of the documentation that wasn't legal documentation was written by Patrick. Patrick has also started multiple software businesses such as a bingo card creator for teachers, an automated appointment system that sent automated reminders to clients, a gaming company for teaching programming called Starfighter, and a software consultancy called Kalezumeus Software. I have devoured Patrick's work. He is one of my favorite online writers. Before we begin, here's my attempt to summarize what I've learned from him in three sentences. First, charge more for your services and products. Second, the economy is much bigger than you thing. Three, create for unique people, not average ones. ____________________________ Show Notes 3:07- What surprised Patrick about writing online. Why writing online takes you from someone who is illegible to someone who is legible. Why blogging has a lower value for business people. 13:40- The benefits of owned platforms vs self-published. What people are missing about writing long-form. How to make the illegible structures legible in your online audience. 24:18- Where all the great bloggers went. Patrick's writing process. Why you should grow an email list. 36:43- How to identify which ideas are worth publishing. How care for the craft has influenced Stripe's culture. 46:55- What writing regularly does for a company. Why write the book before the software. 1:00:01 How "Patio11's law" explains the amount and wealth of niche software companies. How to develop a love for your craft. 1:12:36 How to increase your optimism and ambition. Why self-promotion is like cooking.

My guest today is Will Mannon, the student manager for my online writing school called Write of Passage. Will oversees all aspects of the student experience with the exception of curriculum design. He’s at the frontier of thinking about live online learning, from how assignments should be delivered to how live sessions should be structured. This conversation is a deep-dive into our work together. We start by talking about the difference between Type 1 and Type 2 online courses. Then, we move towards psychological topics like how to hold students accountable to helping them navigate the fear of publishing online. Please enjoy this window into Write of Passage and the future of online learning.    _____________________________________ Show Notes 1:50- David and Will’s focus on customer happiness. Type one and type two online courses. What online educators can learn from the Navy Seals. 13:45- How fear is a part of transformational experiences. What held Will back from starting writing. What music can teach us about great writing. 19:27- Why we fear achieving our vision. Write of Passage guilt. How Write of Passage prioritizes helping people make friends.  27:23- Striking the balance between creating community and letting it grow naturally. How interest groups allow students to create their own communities. The structure of Will’s job as course manager. 35:58- Forte Lab’s yearly planning process. The three phases of Will’s course management. How Will and David are thinking about data collection. 49:14- How Will and David met. How Will’s course feedback led to working with David. Why classical education theory doesn’t really apply to online education. 59:11- Why Will and David create “type 2” courses. Why David learns from his students. How Write of Passages integrates feedback. 1:07:20- What feedback David listens to. The future of Write of Passage. Why David tries to solve very specific problems using software. 1:12:10- How the Internet makes attention a commodity. Why WOP can thrive with zero cold traffic marketing. How the Internet will help make creators money in the future.

My guest today is Sara Dietschy, a YouTuber with more than 620,000 YouTube subscribers. This is the fourth interview I’ve recorded with her. It’s her second appearance on the North Star Podcast, and I’ve been interviewed twice on her podcast called That Creative Life.  Sara makes a couple of videos every week focused on creativity, technology, and entrepreneurship. Most of her revenue comes from paid partnerships, and she’s teamed up with brands like Intel, AT&T, Visa, Squarespace, and BestBuy, and Adobe.  This episode begins with a discussion of what it means to be a YouTuber, so Sara shares lessons about hiring and monetizing a channel. Then, she talks about her creative process with ideas like her “one for them, one for me” model of creating content. We also talk about the future of influencer culture, homeschooling, the Despacito music video, and what we’ve learned about delegation. ___________________________________________ Links to Sara: Sara’s Youtube Channel Sara’s Website   Other Links: Linus Tech Tips Paul Graham’s Maker Schedule, Manager Schedule David’s Obsession Tweet Eric Weinstein- What Should We Be Worried About Epidemic Sound ___________________________________________ SHOW NOTES: 2:02- This isolation of creative hiring. What it means to be a YouTuber. How Sara learns about new technologies. 12:36- What Sara is most opinionated about. How quantification affects Sara’s creative process. 19:30- How Sara creates her content using the “one for me, one for them” model. David and Sara’s creative process. Sara’s relationship to Twitter and YouTube. The future of influencer culture.   31:01- What is good and bad about obsessive personalities. The future of public school and the positives and negatives of homeschooling. The difference between excellence and genius and how school only trains for excellence.  48:02 The gift of truly hating something. The art of video editing and what makes it difficult to delegate. How YouTube has changed over the past ten years. 1:00:55- What Epidemic Sound is doing well. Why Despacito was so popular on YouTube.  1:06:17- Who has done well with delegation. What is so difficult about hiring for creative roles. Why Sara hired a meme creator. 1:18:42- Why differentiation is free marketing on the Internet. Love languages for hiring. David and Sara’s brand dissection podcast plan.  

I have two guests this week: Austin Rief and Alex Lieberman, the founders of Morning Brew. Their business-focused daily email newsletter now has more than 2 million readers. These two gentlemen started the company in college while studying at the University of Michigan. It began as a simple idea — to make business news more interesting for young people. While helping his college classmates prepare for job interviews, Alex noticed they failed to connect with traditional business news. They wanted something better to keep them informed, so he created a daily newsletter that later became Morning Brew.  I will never forget the first time we met. We were introduced by a mutual friend and agreed to coffee at the Beekman Hotel in New York City. We spoke for two-hours about the future of media, then raced to Morning Brew headquarters where we immediately wrote an article called The Pivot to Owned Commerce. One year later, Austin and I recorded a podcast about the secrets of email marketing and the story of Morning Brew.  In this episode, we spoke about the benefits of showing how you run your company, what a Cross-Fit-for-Writing community could look like, and Morning Brew’s secret sauce for hiring writers. Please enjoy my conversation with Austin Rief and Alex Lieberman.  Links: Morning Brew Business Casual Podcast Austin's Twitter Alex's Linkedin

My guest today is Tiago Forte. He runs an online course called Building a Second Brain, which I took in August of 2017. I went from being overwhelmed by information to being in control of it. My writer’s block disappeared and my productivity skyrocketed. Tiago changed the way I thought about work and my relationship with information. Fast forward to today, and Tiago and I are business partners. He helped me create my online writing course, Write of Passage and together, we’re building the infrastructure required to scale an online education business. Tiago is one of my closest friends and the person who shaped my career more than anybody else. In what’s becoming a tradition, Tiago and I used this podcast to reflect on our work together. First, we talked about what we’ve learned about email marketing. Then, we moved onto ideas like leadership, working in small packets, and personal growth. Please enjoy this window into our work and friendship. __________________________________ Links: ConvertKit MindValley  Great Assistant No code  Things  The Decadent Society  David Allen- Getting Things Done  Venkatesh Rao  Teachable  Tyler Cowen- Emergent Ventures  ________________________________________ SHOWNOTES 1:54 Being a Citizen of the Internet. The role that ConvertKit provides for Tiago’s team. How thinking systematically changes how we work for the better. 14:05 The difference between training and teaching through SOP’s. Why David and Tiago hired expensive personal assistants. Why David and Tiago have the goal of only doing something once before finding an automation solution.  27:07 What David and Tiago have learned about running online courses. How online teaching has changed since Tiago and David began their school. What role entertainment and community have in the structure of their courses. 35:05 The dangers of only formulating for ease. The psychology of pricing. The benefits of small, self-motivated teams when you work remotely. 45:05 How “reusable packets” are the backbone of David and Tiago’s work. The “lego block” technique of creating content. How Tiago orients using objects, not humans as linchpins in his business. How David writes first and researches second.  56:33 How the “beginner’s mind” aids David and Tiago write well. How David takes 5 observations a day to create deep and insightful content.  1:04:00 Why books are a mark of legitimacy. The illogicality of fashion. Why publishers want a sure bet. 01:11:40 The next chapter of online education. How scarcity can make time important again. Tiago’s theory about how you to be your full self online now. How instinct works online. 1:23:40 The hero’s journey of sharing your authentic self online. How Tyler Cowen’s mentorship changed David’s life. How Venkatesh Rao changed Tiago’s life. 1:33:22 The shift from interchangeable courses to interesting and specific courses. Why Forte labs is creator-focused, not curriculum-focused. Why building a business is an act of discovery at Forte Labs. 1:42:16 Why David and Tiago are looking for people who have vision combined with passion. Why innovation is directly related to intuition. How to learn faster. 1:53:43 How growth is paying attention to what you are not capable of doing. The skill of knowing the difference between a challenging situation and a fundamentally incompatible one. How the internet can help people create their own definition of success.

My guest today is Michael Mayer, the co-founder and CEO of Bottomless. This episode explores business from a variety of angles. Michael talks about how he thinks about marketing at bottomless, and the accumulating advantages that drive the company. He also talks about what he learned at YCombinator, why startups that move fast have such an advantage, and how to think about execution in a fast-growing company. Five years ago, Michael was a dish washer. Then he worked at Nike before receiving funding from YCombinator and starting Bottomless. Please enjoy my conversation with Michael Mayer. _____________________________________ Links Bottomless https://www.bottomless.com/ Lateral Thinking with Withered Technology https://en.wikipedia.org/wiki/Gunpei_Yokoi#Lateral_Thinking_with_Withered_Technology Y Combinator https://www.ycombinator.com/ Paul Graham http://www.paulgraham.com/ Satoshi Nakamoto’s Bitcoin Whitepaper https://bitcoin.org/bitcoin.pdf Sam Altman- https://blog.samaltman.com/ Wyden and Kennedy https://www.wk.com/ David Ogilvy https://en.wikipedia.org/wiki/David_Ogilvy_(businessman _____________________________________ Show Notes 2:05 The inspiration behind Bottomless. How Michael reformulated coffee supply and demand as an information problem.  How advances in computing and the internet are really advances in legibility. 08:18 The original vision Michael brought to Y Combinator. Bottomless’ marketing plan. Why to buy fresh coffee and grind yourself. 15:50- How Michael’s tech and coffee journey are connected. How to find luxury in inexpensive packages. How many luxuries are just resource intensive. 22:23- What surprised Michael about working with Y Combinator. How the thinking needed in a company gets baked in with the first vector, but extreme execution is what makes success. 26:57- How execution informs Michael’s strategy. Why Bottomless and David strategize on Sunday and execute the rest of the week. How making more decisions more quickly is better than making perfect decisions slowly. 30:30 Michael’s 10-minute interview to get into Y Combinator. When to think, and when to act in your business. Why mistakes are penalized in school, but some of the best things that can happen in life. 37:09 Why to write pseudonymously. What Michael has learned from Paul Graham. Why Bottomless has outsourced a lot of marketing recently. Michael’s experience watching product development while working at Nike. 46:35 Why Michael believes the best people to be doing product development are also doing the operations and customer support. Why status and hierarchy get in the way of running a good business. Why market research should be satisfied by your customer service.  

My guest today is Matt Cooper, the CEO of Skillshare — a subscription-based online learning platform where people can take classes on-demand. The main categories are creative arts, design, entrepreneurship, lifestyle, and technology. Before joining Skillshare, Matt was the CEO of Visually, an online marketing place for creative work. And before that, he was the VP of Operations for oDesk, the world’s largest marketplace for online work now known as UpWork.  Matt and I spoke about the future of education, online and offline. We discussed different business models for online creators, such as Skillshare’s subscription model and the a-la-carte model that I use with Write of Passage. We also talk about what it takes to be successful running an online course, from creating a curriculum to entertaining your students to building an online audience. Please enjoy my conversation with Matt Cooper. ———— 1:55- Skillshare’s model of education. The accessibility of a subscription model. How Skillshare uses behavior to build their algorithms. 11:11- Skillshare's success and failures moving into business education. The benefits of using Skillshare for teachers. Skillshare's revenue model and why they are leaning towards shorter lessons. 15:08-How teachers should tailor their courses for online learning. The production style and schedule of a Skillshare Original class. Why the best teachers are not always the best experts.  22:17 How teachers should consider personality when creating their online materials. Matt's career creating businesses that help freelancers- from unemployment to Skillshare. Why the human element drives Matt's business sense. 30:04- What Matt loves about the open marketplace model. Supply and demand in open market learning. International pricing as an opportunity to build markets. How bundling may be the future of growing certain international markets. 40:28- Matt's experience with education and why there are so many companies based in Plano, TX. Why Skillshare is the new community college. What Matt would do if he was the president of an Ivy League School. Matt's vision for a more efficient model of higher education.  51:30- The value and the cost of a liberal arts education. 59:46- How remote work can both change the quality of life of employees and give companies access to talent they aren't competing with locals for. Why David and Matt bike in New York. Tik tok and the future of production.  1:07:40- Why completion rate is not the most important metric for Skillshare. The challenge of determining user intent. Who is doing the best on search and browse. How Skillshare manages feedback and the social aspects of learning.

My guest today is Hollywood actress, producer and director Jennifer Morrison. She’s known for her roles as Dr. Allison Cameron in the medical-drama series House and Emma Swan in an adventure-fantasy series called Once Upon a Time. She also appeared in movies like Star Trek and TV shows like This is Us and How I Met Your Mother.  We got connected through a workshop I hosted called “How to Crush it on Twitter,” which is exactly the kind of wonderful serendipity I talk about when I talk about why you should share your ideas online. We begin this conversation talking about Jennifer’s time playing clarinet in a marching band. Then, we spoke about how she finds inspiration for stories, chooses what to work on, and how she takes on the role of a character. But the best part comes at the end when we talk about imagination and a movie called “Field of Dreams." Please enjoy my conversation with Jennifer Morrison.  ———— Shownotes 1:36- How Jennifer Morrison began playing clarinet and what separates a world-class marching band from a mediocre one. How Jennifer uses a coach to hone her craft. How Jennifer keeps focus in the high-distraction environment of a live shoot. 13:25- Why Jennifer’s bottom line for judging an acting performance is “do I believe you” and “do I care about you?” How directing has changed Jennifer’s acting. How trust, research, and imagination are Jennifer’s keys to great performance. 25:25- Why Jennifer asks, “what is the ecosystem I am about to join” before signing on a project. How conflict can drive creativity. Posturing versus collaborative problem-solving in Hollywood.  35:15- The cogs of the Hollywood “machine,” and the huge financial bet a studio makes when they hire a new actor. Jennifer’s take on the downsides of celebrity, and the baffling art of being “known for being known.” 48:30- Why coming home after being present with thousands of people is one of the most dangerous moments for an actor. How Jennifer reestablishes her own identity after working. How digital streaming and the internet are like quantum physics. 58:35- How Jennifer and David navigate growing and evolving as individuals while having a backlog of performances and writing available to the public. How Jennifer deals with uncertainty and criticism while still moving forward as an actor. 1:08:12- How reestablishing trust in the world will come from individuals reconnecting to their own truth rather than from the media. Why Jennifer only works on projects that she feels strongly driven to.  2:13:27- How Jennifer thinks the current COVID-19 crisis might influence international film making and consumption.  2:18:25- Why Jennifer thinks that Field of Dreams is a perfect movie.

Today’s guest is Alex Danco, one of my favorite writers in the world. Back when I was in college and before I started writing, Alex was one of the first people who made me say “Wow I want to write like this for a living.” For years, he worked on the Discover team at Social Capital where he wrote a weekly newsletter called Snippets. Now, he’s joining the Shopify Money team, where he’s building the future of financing merchants and entrepreneurs with everything they do. This episode begins with a conversation about a book called Technological Revolutions and Financial Capital. It’s a favorite of investors like Fred Wilson and Marc Andreessen and Alex breaks it all down for us. Then, we talk about cities and the growth of suburbs in North America. And finally, we talk about the mechanics of writing online. ____________________________ Shownotes 2:10- How Alex found Carlotta Perez and her book Technological Revolutions and Financial Capital through the work of Bill Janeway. Why, if you are creating an unknown truly new product, you cannot know the value of your equity. How the venture capital community uses tested milestones to show potential value to investors. 10:20- An overview of the two main ways that risky business ventures were funded before VC. How financial capital and production capital exist fundamentally in tension with each other. Carlotta Perez’s theory on the life cycle of financial bubbles. 17:15- Is entrepreneurship across the US growing or shrinking today? Why the current VC and tech industry is a great example of "we shape our tools and then they shape us." Why founders are increasingly interested in funding that prioritizes optionality. 27:00- Why venture capital values opposite indicators of success than the general economy. Why so much education for innovators is focused on venture capitalism. Why Alex believes that financial Twitter will help fill the role of intellectual stimulation for people managing boring businesses.  34:30- Why Alex writes 5,000 words a week. How writing in public can help in ways that just thinking does not.  39:10- How to find "the villain" in your writing. How Alex believes urbanization and intellectual migration to cities will change in the US in the future. Jane Jacobs and the idea of complete communities versus gentrification. 48:18- Why complete communities are now found in the suburbs. The growing pains of Toronto. Why so many world-class musicians have come out of Toronto. How do highways create local culture? 59:10- What the organic, long-lived nature of cities means for how they change. How autonomous vehicles will change cities. How the pricing power and efficiency of large companies distorts the true cost of shipping, healthcare, and education. 1:08:10- How audio changes our brains. How the feed-forward system works in our sensory perception and motor function. Alex explains Claude Shannon's information theory and Marshal McLuhan quote "the medium is the message." 1:21:42- Why audio is the most information-heavy medium. Why great writing is not written the way that the author speaks. How Alex interprets the classic Nixon/Kennedy debate story.  1:27:22- What the rise of podcasts means for media consumption and mental processing in the US. Why Donald Trump thrives in an audio environment.  1:32:07- How Alex uses summarizing to improve his writing. How publishing every week informs Alex's content. Why the background information in your writing is some of the most important material in your post. 1:37:14 How Alex crafted his piece Social Status in Silicon Valley. How to create new ideas and work using an anchor in what you know.

My guest today is Ryan Singer, the head of Project Strategy at Basecamp. Ryan recently published a book called Shape Up where he describes his process for planning, designing, and executing projects at Basecamp. In this interview, instead of talking about Shape Up and the principles in the book directly, we danced around those topics and applied them to ideas like consciousness, architecture, and product management. We talked about the interaction between design and consciousness and how Ryan’s love of architecture lead him to Christopher Alexander. We talk about relationships between top-down and bottom-up perspectives on the world and how you can synthesize the two. Our conversation begins by applying Shape Up to the writing process. At times this conversation is practical and at times it gets spiritual. ____________________________ Shownotes 2:02- How Ryan used the core principles of Shape Up to structure, focus, and ultimately write his book, using workshops to refine how you present your ideas and the necessity of using time constraints and process clarification to move through the different processes of writing. 8:29- Ryan’s transition from being a designer to a designing programmer and the successful elements of teamwork that Ryan has identified over his 16 years at Basecamp. 15:13- How impact and team satisfaction drives productivity and focus for Ryan’s team and how the 6-week schedule at Basecamp facilitates this satisfaction. The balance you can find by asking, “How far can you push in one push?” 19:57- How enthusiasm paired with timeboxing helps a team feel energetic but still healthy, the nuance of using a firm 6-week time boundary for a project, and how hard walls with a soft middle are key to the Shape Up method.  26:44- How a team can be committed to the end goal without being attached to how to get there, why Ryan uses the deeply matured truth of architecture to inform his work in the newer field of interaction design and his appreciation of Christopher Alexander’s design principles. 35:18- How only a deep understanding of a problem can inform the comparison methods for the potential solutions, the multiscale principle as relates to Modernist buildings and design, and the playout of human scale and architecture in Minecraft and tourist destinations. Ryan asks the question, “how do we specify the large scale and allow the people living there to design the small scale?” 49:44- Why Ryan chose “Felt Presence” as the name of his website, how consciousness and the mind inform Ryan’s design work, how Bob Moesta’s work to understand why people reach for a Snickers bar informed a redesign of the candy. 55:52- How understanding the underlying causes of a situation can help you design a useful solution.

My guest today is software engineer, designer, and researcher Andy Matuschak. He’s focused on Tools for Thought — which is a fancy way of saying that he works on technologies that expand what people can think and do. Before working as a researcher, he helped build iOS at Apple, focusing on foundations like multitouch, animation, and inter-app coordination. Then, he worked at Khan Academy where he led and co-founded the Research & Development group. In this conversation, we talk about the structure of online education, how to take notes, strategies for developing new ideas over time, secrets of creative partnerships, and what it means to do creative work. This conversation begins with a discussion of my online writing course, Write of Passage. I hope you enjoy this conversation.

My guest today is Chris Zarou, the CEO of Visionary Music Group and the behind-the-scenes mastermind behind the success of Logic and Jon Bellion. I’ve been a fan of both his artists since my early days of college, so I’ve watched them both blow up with my own eyes. The episode begins with Chris’ time playing Division 1 soccer before transitioning to artist management. From there, he talks about how he met Logic and what he’s learned from Jon Bellion about the creative process. And finally, we dive into all facets of the Hip-Hop industry from his method of finding new artists, to the economics of concerts and music festivals. I hope you enjoy this episode.

My guest today is Robert Cottrell, the founder of The Browser, which has become my go-to source for articles. Here’s how it works. Every day, he recommends five articles and includes a short summary for each one. They’re wild and random — but that’s what makes his work so exciting. For example, today’s issue has an articles about how bees argue, the battle of ideas in China, how Americans should think about nuclear weapons, the circus arts, and the future of machine-created art. In this episode, we talk about why journalism is one of the most under-valued crafts in the world, what we should know about Latvia, and the cutting edge of language translation software. Please enjoy my conversation with Robert Cottrell. 

My guest today is Andy McCune, an entrepreneur and creative who co-founded Unfold, a mobile design tool kit for storytellers that was acquired by Squarespace. He also runs an Instagram account called Earth (@earth on Instagram) with 1.1 million followers. Andy is one of the very most talented people I know. And he has a more intuitive, make-it-and-test-it way of working than most of the people on this podcast. I’ve built a friendship with him as he’s flown under the radar for years. I remember talking to Andy about Unfold back when it was just a small side project, and it’s been a joy to watch Andy grow and scale the business. Please enjoy my conversation with Andy McCune.

My guest today is Samo Burja, the founder of Bismarck Analysis, a firm that analyzes institutions, governments, and companies for high net worth individuals. Samo is known for an idea called Great Founder Theory, and his research focuses on the causes of societal decay and flourishing.    This is my second time having Samo on the podcast. In this episode, we spoke about high vs. low trust societies, the difference between writing styles in New York and San Francisco, the economics of building an online audience, and how the Internet is raising the value of being a good photographer. But first, we begin talking about how-to videos on YouTube, and their influence on culture. I hope you enjoy this episode.  

My guest today is Tiago Forte, who runs an online course called Building a Second Brain.   This episode is different than most of my podcasts. It’s less of an interview and more of a conversation.   Tiago and I have collaborated closely for the past year. In February, we worked together to film and produce my online writing course called Write of Passage. And throughout the year, we’ve teamed up to improve every aspect of the student experience.   We recorded this episode from Arizona where we were hosting our Creative Process Workshop, which offers a radical new approach to writing in the Information Age, just like Write of Passage.    In this conversation, we reflect on the time we’ve spent working together, explore the key trends in online education, and talk about what we’ve learned by teaching more than 1,000 students combined.   Please enjoy my conversation with Tiago Forte.     -- --    2:15 – the shifting bottleneck of online education   10:53 – discovering how much our own identities/how we perceive ourselves impact our actions   13:30 – changing identity on scale through online schooling   25:04 – the audio revolution and returning to Marshall McLuhan   28:20 – origin story of Write of Passage   35:23 – how feedback loops exponentially increases your output   41:50 – it’s easier than ever to create, so what has gotten harder   48:20 – the evolution of note taking   54:38 – C.R.I.B.S.   58:55 – to create takes courage OR the internet just magnifies humanity   1:04:49 – if you can easily describe what you are doing it’s probably not ambitious enough   1:13:05 – everything is “figureoutable”   1:19:20 – reaching quality through quantity   1:28:19 – Michigan and Ford factory visit   1:35:41 – the power of a weakness   1:41:40 – you cannot change your own identity without growth   1:44:52 – importance of constraints   1:50:40 – what’s the experience of playing with constraints and an example of an outcome?   1:56:32 – writing as thinking and re-writing as re-thinking   2:00:52 – “freedom to make a bad painting”   2:04:32 – the paradox of specificity: the more specific what you are known for is, the more opportunities you’ll attract

My guest today is Ryan Holiday. He’s a writer, media strategist, and the author of ten books. He dropped out of college at 19 years old to apprentice under Ryan Greene, author of Mastery and The 48 Laws of Power. He worked at American Apparel and founded an agency called Brass Check. We begin this episode talking about two stories from Ryan’s book, Stillness is the Key. One is about Michael Jordan and the other is about Winston Churchill. Then we transition into new topics. We talk about the philosophy of stoicism, the benefits and drawbacks of anger, and what Ryan has learned from Peter Thiel. Please enjoy my conversation with Ryan Holiday. -- --  1:32 Winston Churchill – the busiest man in the 20th century: saw the last British Calvary charge, writes 10 million words, holds office for 65 years, elected Prime Minister twice, painted 500 paintings etc. 7:06 Can a change of location effect your relationship to time?   12:37 Writing as zero-to-one and the importance of getting something down in order to gain momentum. 17:02 Michael Jordan’s Hall-of-Fame Speech where we learned how importance anger as fuel and making a career of hanging onto slights was to him. Could Michael Jordan have been Michael Jordan without these characteristics? 20:30 How widespread is anger as fuel to success? Is it the best method and how much correlation is there to someone’s success? 27:20 Anger as a “purity” in our current political landscape. 29:08 Taking a look at the history of change and how the News may not be the best way to stay informed. Is the current understanding of “being informed” is a vice rather than a virtue?   36:20 To be “informed” need to have basis of understanding before interacting with News sources in order to contextualize and not come at news with hubris. Problem of the twitter approach to news: a profession, reporting, that was once about thoughtfulness, nuance, and the long-form has been boiled down to 280 characters.   41:19 Stillness is the Key as part of a trilogy involving Ego is the Key and The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph. This trilogy was what Ryan had always intended to write but had to go through his other books to get where he is now. 46:35 Truly integrating stoicism into his everyday life.   53:18 Peter Thiel’s brain is in a perpetual Mexican standoff where two competing ideas are constantly in opposition. Thiel seems to have a great ability to frame subjects correctly. Eric Weinstein's idea that Thiel is the world's wealthiest applied philosopher. 58:00 Extending Thiel’s First Principles Movement by simply reading different things than what everyone else is reading, gathering different materials. 1:00:02 Is there a danger where reading history becomes the same thing as watching the news? Ryan’s interest in reading personalized experiences of history wherein you can learn through other people’s unique experiences, and more importantly, mistakes.   1:02:25 Ryan’s writing success is owed to him taking the words of smarter people them him, re-arraigning them and repackaging them into a unique system. Does writing always have to be original?    1:05:19 What is it about daily things that is so important to Ryan?   1:10:42 The idea of looking at data that shows what artists believe is their best work and what others believe to be their best work.   1:16:11 How do you know when something is interesting?    1:20:32 How is Ryan such a prolific writer?       

My guest today is Cameron Porter, an investor and former professional soccer player.  We begin the conversation talking about AlleyCorp, an investment firm in New York where Cameron is responsible for new company research and development and due diligence on seed investment. Then we move to Cameron’s experience playing professional soccer in Montreal and Kansas City, and leading the NCAA in goal scoring during his senior year at Princeton. Since Cameron is a true generalist, we explore neural networks and brainstorm ways to increase technological progress beyond the smartphone. We end the podcast with a deep and unbounded discussion about community and loneliness. In it, we explore the societal and personal impact of social media, social clubs, and the decline of religion in the West. Please enjoy my conversation with Cameron Porter.   2:19 – Idiation at Alleycorp and what is AlleyCorp? 6:17 – P-Type and S-Type Innovations 11:49 – The story of AlleyCorp 19:36 – Business Insider capitalized on being the first to use the internet to publish news during the day 26:22 – Cameron’s incredible origin story 32:05 – As Cameron’s College soccer pedigree grows he decides to go to Asia for the Summer instead of training for a potential MLS career 35:58 - After leading the country in goals Cameron is drafted by Montreal 41:52 – Cameron is traded to Kansas City after blowing out his knee but soon suffers another debilitating injury 46:12 – During your MLS time you are given the opportunity to do nothing except play soccer 52:07 – What advantages at Alleycorp do you have over large venture capitalist firms? 1:01:43 – What is something exciting happening at Alleycorp? 1:09:41 - The stagnation of innovation 1:15:43 – Emergence driven by the individual 1:20:17 – We are not pushing forward innovation with re: to the atoms of the world 1:25:38 - Kenneth Stanley’s “Greatness Can’t be Planned” vs. Peter Thiel’s “Definite Optimism” 1:33:27 – Artists and soldiers 1:42:40 - Television and Airpods have increased social isolation and our ability to avoid risk 1:51:44 – Baboons in Africa have figured out how to live better than human beings 1:59:33 – The curious case of San Sebastian 2:06:10 – Real community is a place where they miss you when you’re gone and they have a mechanism for bringing you back 2:18:37 – “Wake up excited and go to bed tired”

Emmett pioneered the Direct-to-Consumer aesthetic. The bright colors, the flat design, and the sans serif fonts are a direct result of his work. At Gin Lane, he worked with brands like Bonobos, SweetGreen, Harry’s, Smile Direct Club, and Recess. Now, he’s switching gears. Emmett and his team launched Pattern, a family of brands with products and guidance that inspire people to live a more present life.   Emmett isn’t a Luddite, but he’s skeptical of the effects of modern technology and our obsession with efficiency.     I admire Emmett’s ability to match the intuitive and the intellectual, the quantitative and the qualitative. He loves to read but doesn’t get bogged down by the dogma and precedent. He loves to be creative but isn’t trapped by the myth of the messy artist whose life is in shambles. He’s a sharp critic, a careful observer, and a prolific designer. And in this episode, Emmett reveals his true colors. But I’ll warn you, there are some curse words in this episode due to the passion of the conversation. Enjoy my conversation with Emmett Shine. 

In December, I went to a live taping of the Tim Ferriss Podcast at the famous 92nd Street Y in New York City. There was a surprise guest at the event named Adam Robinson, and after hearing him speak, I tapped my friend on the shoulder and told him I’d find a way to get him on the podcast.  Adam Robinson cracked the SAT before co-founding the Princeton Review. He also wrote the only test preparation book to ever become a New York Times bestseller. He attended The Wharton School at the University of Pennsylvania as an undergrad before studying law at Oxford University in England.  He’s a rated chess master with a Life Title and as a teenager was personally mentored by Bobby Fischer—considered by many experts to be the greatest chess player of all time—as he prepared for the world championship.  Today, he applies his unique philosophy and methodology as an independent global investment advisor to the heads of some of the world's largest hedge funds.  After this conversation, I can confidently say that nobody thinks like Adam Robinson.

My guest today is Renée DiResta, who spends her time investigating the spread of malign narratives across social networks. She has advised Congress, the State Department, and policymakers in understanding and responding to the problem of misinformation. In this episode, we talk about the history of misinformation and propaganda. We go back to the roots of media theory and explore the ideas of people like Edward Bernays, Walter Lippmann, and Marshall McLuhan. I found Renée through an excellent essay called The Digital Maginot Line, which we discuss at the end of today’s podcast. I hope you enjoy this episode.

My guest today is Tren Griffin, a Senior Director at Microsoft and the man behind an excellent blog called 25IQ. Tren is one of the most prolific writers I know. He’s written books about negotiation, entrepreneurship, and Charlie Munger. He published an article every week for almost six years, and because of all that hard work, he’s now posted more than 1.3 million words online. We start the conversation by talking about his writing process. Then, we talk about distribution in the cellular business, Software-as-a-Service business models, and lessons from his legendary entrepreneur Craig McCaw. After an afternoon with Tren, I feel like he gets more excited about ideas than anybody I’ve ever met. Tren loves life, loves people, and in this conversation, you’ll see just how much he loves ideas.   SUBSCRIBE TO MY “MONDAY MUSINGS” NEWSLETTER TO KEEP UP WITH THE PODCAST. LINKS: Find Tren online: Twitter 25iq Other links: Bill Gurley  Benchmark Capital Craig McCaw Santa Fe Institute Patrick Collison Richard Zeckhauser Charlie Munger Ed Thorpe Lil Wayne Nassim Taleb John Malone SHOW NOTES 1:46 How did Tren get started with writing, why he is so disciplined about the writing process, and   9:44 What Tren told data scientists during his talk on complex adaptive systems, how to calibrate yourself to business cycles, and trusting the process 21:21 Acquiring judgment through seeing smart people make decisions and what Tren learned from Craig McCaw 33:25 The genesis of the software in the box business model, what the future of the book is going to look like, and the importance of curated marketplaces 41:02 The influence of the Santa Fe Institute, why distribution is so hard, and the key elements of defensibility of companies 54:03 Patrick Collison on raising the intellectual bar at Stripe, what Tren has learned from Richard Zeckhauser, and the importance of first party stories 1:05:02 Demand side economies of sale and what Tren has learn from Charlie Munger, Ed Thorpe, and Lil Wayne 1:17:48 How Tren got into hip hop, Nassim Taleb, and John Malone 1:29:53 What Tren has learned from Bill Gurley

My guest today is Mason Hartman. For years, I’ve admired Mason's perspectives on the culture, childhood, and the education system. I teach an online writing course called Write of Passage. So education –  and especially writing education – is a subject that's close to my heart. We recorded this episode in Los Angeles, where Mason works at a school for gifted children and does most of her research. In this episode, we chat about all things education early childhood development, the road to college, and why childhood has become a full time job. Then we close the episode with lessons from two of Mason's favorite people, David Deutsch and Patrick Collison. I hope you enjoy this episode. SUBSCRIBE TO MY “MONDAY MUSINGS” NEWSLETTER TO KEEP UP WITH THE PODCAST. LINKS: Find Mason online: Twitter Other links: The Coddling of the American Mind by Jonathan Heidt and Greg Lukianoff How Schools Work by Arne Duncan   Michael Nielsen Patrick Collison David Deutsch SHOW NOTES 1:17 How to move away from the Overton window, why David’s most creative podcast guests grew up in rural environments, and why it’s important to let kids take a few bruises in a relatively safe environment 5:15 The Coddling of the American Mind, how to design schools that don’t coddle kids, and why teenage sleep deprivation leads to more accidents than drunk driving 14:05 Why standardized testing are antithetical to the underlying skills they are trying to measure, how to evaluate people when real stakes are involved, and Mason’s thoughts on the recent college admissions scandal 21:26 The binding thread that ties together Mason’s intellectual interests, how gifted kids identify each other’s strengths, and why is obsession so important to develop mastery  30:36 How obsession can equate to imagination and resilience, Masons’ thoughts on the professionalization of young kids, and the standardized expectations for kindergartners 39:44 Unbounded and bounded learning environments, how to use remixing as a way to deal with blank page syndrome, and what Mason thinks about homeschooling 52:44 What Mason thinks are the best ways to raising other’s expectations of themselves, how middle class kids are forced to pursue uncreative paths, and how exclusive colleges exploit low acceptance rates 1:01:37 The commodification of kids, the balance between rationality and intuition, and how to raise the status of obsession 1:11:47 Why you shouldn’t work on projects that you can get a grant for, how risk taking leads to progress, and what Mason learned from David Deutsch 1:23:31 Why is Mason inspired by Patrick Collison, how to ask a poignant and precise question, and why the most curious people are good at listening SUBSCRIBE TO MY “MONDAY MUSINGS” NEWSLETTER TO KEEP UP WITH THE PODCAST.

My guest today is Jeff Morris Jr., the Director of Revenue at Tinder. We begin this episode talking about the future of education. Jeff recently completed an MBA at UCLA and wrote his thesis on the future of Lambda School, the San Francisco based education startup. We talked about the transition from marketing funnels to marketing loops and how Tinder is growing its average revenue per user. We also explore Hollywood's transition from movies to television, and the letter Jeff received from legendary UCLA college basketball coach John Wooden. We also explore some career strategies for sparking serendipity. I hope you enjoy our conversation. SUBSCRIBE TO MY “MONDAY MUSINGS” NEWSLETTER TO KEEP UP WITH THE PODCAST. Where to find Jeff online: Twitter Website Tinder Other links: Ryan Holdaway Lambda School K-factor by Andrew Chen  Modern Romance by Aziz Ansari RigUp Brian Nogard Show Notes: 1:18 What Jeff learned from working with Lambda school on their Outcomes team, why the incentive structure for traditional colleges is broken, and why Jeff got an MBA despite believing in the future of education looking like Lambda school? 7:43 How Jeff had to scale himself up by becoming a lot more quantitative as the Director of Revenue at Twitter, how marketing at startups has changed from funnels to loops, and the cultural power of the Tinder swipe. 12:54 How average revenue per use has come up at Tinder over the last two years, how to build a successful social product that is low in the Maslow’s hierarchy of needs, and how Tinder balances perceived coolness and utility. 18:11 The historic geographical limitations of dating, the evergreen trends in dating, and what has Jeff learned about compatibility between people through his time at Tinder 23:17 How Jeff thinks about inequality in the Tinder ecosystem, how movies and TV have set up a false idea of how people meet, and what Jeff learned about romance from film school. 30:08 The switch from Hollywood to TV for film school graduates, why TV is uniquely suited to the subscription model, and why David thinks that exporting cool is LA’s core competency 44:34 Retraining in the Lambda school era, high growth jobs that are easy to retrain for, and dynamics of proving competence and expertise 52:26 Why Jeff sent a letter to John Wooden and other celebrities, what he learned about outbound emails, and how to find the ‘underpriced assets’ when it comes to talent 1:00:55 How Jeff got a job at Zaarly ahead of hundreds of other candidates, how that experience expanded his worldview, and what you can do to set yourself apart in the job search process 1:04:47 David and Jeff give the listeners a challenge, what Jeff learned from Brian Norgard about products, and how Jeff thinks about disruption 1:17:17 The verticalization of LinkedIn and other incumbents, and why Jeff thinks being on Twitter is the reason for his high growth career SUBSCRIBE TO MY “MONDAY MUSINGS” NEWSLETTER TO KEEP UP WITH THE PODCAST.

My guest today is Steve Cheney, the cofounder of Estimote. Before founding Estimote, Steve was the head of business and platform at GroupMe, which was acquired by Skype. I’ve been reading Steve's writing for more than half a decade, but this year, he picked up the pace of his publishing and now I’m hooked. This episode begins with the discussion of startup dynamics. We talked about fundraising, capital efficiency, and why Steve believes that every dollar from a customer is five times more valuable than a one dollar from an investor. Then we explore the world of frontier technologies. We talked about augmented reality, self driving cars, and image recognition software. Then at the end of the episode, Steve talks about why he's been so successful writing online. Steve talks about his journey of sharing his ideas, how he started writing for Techcrunch, and why writing online is the best way to get discovered right now. This was without question, my favorite part of the episode because it ties right into my work. I teach an online course called Write of Passage where students learn to accelerate their career by writing online and by building an audience. i hope you enjoy my conversation with Steve Cheney. SUBSCRIBE TO MY “MONDAY MUSINGS” NEWSLETTER TO KEEP UP WITH THE PODCAST. SHOW TOPICS LINKS: Find Matt online: Twitter Website Estimote Other mentions: Ben Thompson Write of Passage On How to be Discovered Knowledge and Power by George Gilder SHOW NOTES 1:53 What startups get wrong about capital efficiency, trap door decisions, and how fundraising cycles for startups work  11:35 Why Steve changed his perspective on capital efficiency, why is every dollar from a customer is five times more valuable than a one dollar from an investor, and the importance of employee retention in startups 20:09 The importance of avoiding competition for talent, why Steve’s Electrical Engineering background was very good training for startups, and the future of image recognition 33:16 Tesla and why image recognition is the next act of the internet, why frontier technologies are driven by cost curves, and the latest improvements in eyesight  43:53 The physical limits to wireless and how they are being pushed, what the future of authenticity will look like, and the defining experiences in Steve’s childhood 57:37 Steve’s core beliefs, how he has changed his views on them, and what Steve believes are his core skills 1:01:57 Why you want to work at a product-driven organization, creating something in a new area of technology, and zero sum games 1:09:40 Why Steve got back to writing online, how writing helps him learn, why writing online is the best way to get discovered 1:12:46 The switch from public to private conversations when you write online, how to crank out blog posts and get your ideas on the page, why inspiration is perishable and the importance of taking notes on things that inspire you 1:19:12 How to not get discouraged by an initial slow pace of writing, the importance of reading a lot to be a good writer, and how to become good at curation SUBSCRIBE TO MY “MONDAY MUSINGS” NEWSLETTER TO KEEP UP WITH THE PODCAST.  

My guest today is Matt Mullenweg, the founder and CEO of Automattic. Automattic is known for Wordpress, which powers a third of the internet. Matt and I talk about the democratization of the web, the early days of Wordpress, and how he makes sense of the incredible scale of the company. We dive into the benefits of writing online, talk about inbound vs. outbound opportunities and the open web. Then we discuss why Automattic bought Longreads, the content triangle, and the Caro books. Finally, we talk about his love for sci-fi, why writing is the ultimate long-now activity, and what’s next for Wordpress. I hope you enjoy this episode. SUBSCRIBE TO MY “MONDAY MUSINGS” NEWSLETTER TO KEEP UP WITH THE PODCAST. SHOW TOPICS LINKS: Find Matt online: Twitter Website Automattic Other mentions: Ben Thompson Write of Passage Longreads The Content Triangle The Years of LBJ by Robert Caro SHOW NOTES 1:56 Democratizing the web, building an operating system for the open web, how Matt thinks about everything in terms of communication, and the tradeoff between powerful and intuitive 9:33 How Matt makes sense of the incredible scale of Wordpress, commodification in the age of social media, and building communities 18:57 The difference between inbound and outbound opportunities, how to reverse engineer your goals, and what Matt thinks about Ben Thompson’s Stratechery 26:26 The democratization of the means of distribution, what Matt was writing about at age 19, and the acceleration of evolution through the internet 35:23 Why Matt and Automattic bought Longreads, Robert Caro’s The Years of LBJ, and the feeling of not having anything important to say when you’re starting out 43:54 What Matt thinks about the content triangle, the good and bad ways of collaborating, and why iteration is the way to improve your writing 49:50 How a healthy comment section is like a good dinner party, why default settings are important, why Matt likes reading sci-fi, and why writing is the ultimate long-now activity SUBSCRIBE TO MY “MONDAY MUSINGS” NEWSLETTER TO KEEP UP WITH THE PODCAST.

My guest today is Jason Zweig, a personal finance columnist for The Wall Street Journal. He's also the author of the revised edition of Benjamin Graham's The Intelligent Investor, which Warren Buffett has described as "by far the best book about investing ever written." We begin the episode by discussing the evening Jason spent with Charlie Munger at his home in Southern California. Then we talked about Jason's collaboration with Daniel Kahneman, the Nobel Prize winning behavioral economist. We discuss Jason's time growing up on a small farm in upstate New York, and why Jason's Wall Street Journal columns are intended to save investors from themselves. Then we had a conversation talking about the power of small details and communication, and why writing demands fresh language. And nearly every single part of this conversation applies to my online writing course called Write of Passage, where I teach students to launch a personal website, build their writing habits, and attract an online audience. SUBSCRIBE TO MY “MONDAY MUSINGS” NEWSLETTER TO KEEP UP WITH THE PODCAST. SHOW TOPICS LINKS: Find Jason online: Twitter Website WSJ’s The Intelligent Investor Other mentions: Charlie Munger, Unplugged by Jason Zweig (Paywall) The Intelligent Investor by Benjamin Graham Thinking, Fast and Slow by Daniel Kahneman Look Homeward Angel by Thomas Wolf The Years of LBJ by Robert Caro SHOW NOTES 1:38 What Jason learned from his six-hour long conversation with Charlie Munger, delivering the same information in different and entertaining ways, why you should bet on regression to the mean instead of being procyclical when it comes investing. 8:00 What are the similarities between Charlie Munger and Daniel Kahneman, why you have to be ready to kill your darlings when it comes to writing, and what does Jason’s information diet looks like. 24:10 How Jason thinks about the idea of “saving investors from themselves”, the role of entertainment in Jason’s writings, why clichés are a symptom of lazy thinking, and inflection points in Jason’s career 42:10 How growing up in rural New York fueled Jason’s intellectual curiosity, how Jason would approach building a writing career if he was just starting out, and why you should treat words like 45 pound dumbbells. 55:44 Pivotal moments that influenced Jason’s writing process, the importance of being able to take criticism well, and how Jason uses collective intelligence to improve his thinking 1:08:17 The dangers of learning too narrow a lesson, how Jason was as a young college student, and why overconfidence might a positive influence for young writers SUBSCRIBE TO MY “MONDAY MUSINGS” NEWSLETTER TO KEEP UP WITH THE PODCAST.