Podcast appearances and mentions of lenny rachitsky

Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Sanket Kavishwar, Director of Product at Relyance AI. Sanket is one of the most active members in Supra's AI workflows Slack channel, and in this episode, we explore how he's transforming his company's product development process with AI prototyping tools like V0.We dive into how Relyance AI shifted from traditional PRDs to problem statements and interactive prototypes, dramatically accelerating iteration speed, improving customer feedback loops, and empowering PMs to communicate ideas visually without waiting on design resources. Sanket also shares practical advice for introducing AI prototyping into your company - no matter the size, and how it can unlock faster cross-functional collaboration across product, engineering, and go-to-market teams.If you're a PM, designer, or founder looking for ways to make your product development cycles faster, sharper, and more collaborative, this episode is packed with actionable insights you can apply today.All episodes of the podcast are also available on Spotify, Apple and YouTube.New to the pod? Subscribe below to get the next episode in your inbox

Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Will Newton, Principal Product Architect at Amplitude—and one of our most popular past guests—for a follow-up conversation on the fast-evolving world of AI tooling in product design and development.In just a few weeks since our last chat, Amplitude has gone from early AI experimentation to giving Bolt licenses to every designer. Will takes us inside this transition and breaks down how AI is changing design workflows, redefining prototyping, and collapsing traditional linear product development.We also get deep on the concept of taste—what it means to produce high-quality work in a world where the UI layer is increasingly commoditized. Plus, a live Bolt demo, the hidden risks of lazy thinking with AI, and why the future belongs to generalists with strong judgment and taste.If you're a PM, designer, or product leader trying to make sense of the new AI-powered stack, this one's for you.All episodes of the podcast are also available on Spotify, Apple and YouTube.New to the pod? Subscribe below to get the next episode in your inbox

Jonny Miller is the creator of Nervous System Mastery. It teaches evidence-backed protocols to cultivate calm, build resilience, and increase aliveness in 45 days. It's a five-week, cohort-based course that is just wrapping up its sixth cohort in the last three years. In those six cohorts, Jonny has served nearly 1,000 students and earned more than $800,000. Here's the best part – Jonny doesn't have a massive audience. When he launched Nervous System Mastery, he had a couple thousand followers on Twitter and a small email list. This is the magic of a well-designed Signature Product – and Jonny is the perfect example. In this episode, we get into the weeds about how he's grown NSM – what's worked well, what hasn't, and how he's found himself on large podcasts with people like Lenny Rachitsky, Ali Abdaal, Chris Williamson, and more. → Join Nervous System Mastery Full transcript and show notes Jonny's Website / Twitter / Instagram / LinkedIn *** RECOMMENDED NEXT EPISODE → #221: Ryan Hawk – Anatomy of a $12,500 membership earning $400,000+ per year *** ASK CREATOR SCIENCE → Submit your question here *** WHEN YOU'RE READY

Welcome to another episode of Supra Insider. This time, Ben and Marc sat down with Tal Raviv and Colin Matthews for a candid conversation about how AI is reshaping the work and mindset of modern product managers.They unpack insights from Tal's recent survey on AI prototyping adoption, common challenges for PMs using AI tools, and the importance of learning how to experiment effectively. Colin shares how his approach to evaluating side projects has shifted now that AI accelerates time to build—and why go-to-market remains the biggest bottleneck.They also explore why some companies still penalize failure, how team dynamics are evolving as PMs become more self-sufficient, and why embracing high-leverage work is more critical than ever. If you're a PM, solopreneur, or product leader trying to navigate the new AI era, this episode is packed with honest takes and practical advice.All episodes of the podcast are also available on Spotify, Apple and YouTube.New to the pod? Subscribe below to get the next episode in your inbox

Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with John Cutler and Joshua Herzig-Marx for a wide-ranging conversation about how AI is transforming the way product teams build, collaborate, and scale. John shares why he joined a new early-stage startup as Head of Product and how the team is breaking the traditional rules of product development—starting with a platform-first mindset.The conversation explores the rise of highly configurable tools, the new personas emerging in AI-native organizations, and how simulations, knowledge graphs, and organizational ontologies might shape the next generation of work. Whether you're a product leader, founder, or operator curious about the frontier of product ops and AI tooling, this episode offers tons of insight—and inspiration.All episodes of the podcast are also available on Spotify, Apple and YouTube.New to the pod? Subscribe below to get the next episode in your inbox

Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Steven Fabre, co-founder and CEO of Liveblocks, a company helping product teams seamlessly build collaborative experiences—now with AI copilots in the mix.In this conversation, Steven shares his journey from being a designer at InVision to leading a developer tools company that's rethinking collaboration in the AI era. They talk about how Liveblocks is evolving from enabling human-to-human collaboration to supporting humans and AI working together in real time—and what that means for interface design, trust, and product differentiation.Steven also shares how he's staying ahead of the curve by studying patterns across tools like Figma, Notion, Stripe, and Claude—and how building great developer tools today means thinking about developer experience and end-user UX at the same time.Whether you're a founder, product leader, or designer thinking about how AI might shape your product, this episode offers a grounded and inspiring look at what's coming next.All episodes of the podcast are also available on Spotify, Apple and YouTube.New to the pod? Subscribe below to get the next episode in your inbox

Welcome to another episode of Supra Insider. This time, Marc sat down with Phil Ou, founder of Blossomer and former product leader at Google, where he led teams across Google Photos, RCS, and YouTube Ads. Phil now helps early-stage B2B founders get their first 1,000 customers—without hiring a sales team.In this episode, they unpack what it really takes to build a repeatable go-to-market engine, the decision to bootstrap vs. raise VC, and the biggest mistakes founders make when thinking about growth. Phil also shares how he uses AI tools to save hours each week—from custom GPTs to automated sales prep—and why relevance beats personalization in modern outbound.If you're a product leader curious about starting your own business, or a founder looking to improve your GTM strategy and use AI more effectively, this episode is packed with practical insights.All episodes of the podcast are also available on Spotify, Apple and YouTube.New to the pod? Subscribe below to get the next episode in your inbox

Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Rodrigo Davies, the product leader shaping Asana's AI strategy. Rodrigo shares his journey leading AI adoption at Asana, from educating internal teams to building a culture of AI experimentation.We explore how Asana integrates AI into work management, balances AI innovation with enterprise needs, and develops features that deliver real value—not just hype. Rodrigo also talks about how AI is changing the product development process, the importance of hands-on tinkering, and why AI needs to earn trust before it can take over critical workflows.Whether you're a PM, designer, or engineer working on AI features—or just curious about how a large tech company approaches AI—this episode is packed with insights.All episodes of the podcast are also available on Spotify, Apple and YouTube.New to the pod? Subscribe below to get the next episode in your inbox

Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Randhir Vieira, Chief Product Officer at Omada Health and a Supra facilitator. Randhir has led product teams at companies like Headspace and brings a deep passion for leadership, communication, and the often-overlooked skill of listening.In this episode, we explore why listening is the foundation of strong leadership, how to give feedback that actually lands, and why the best product leaders focus on building psychological safety in their teams. Randhir also shares practical frameworks for improving team collaboration, handling difficult conversations, and fostering a culture of trust.If you're a product leader looking to sharpen your leadership skills, a founder building a team, or someone navigating tricky workplace dynamics, this conversation is packed with actionable takeaways.All episodes of the podcast are also available on Spotify, Apple and YouTube.New to the pod? Subscribe below to get the next episode in your inbox

La rapina di criptovalute del secolo. Pubblicità sul registro elettronico. Doppiaggio IA su Amazon Prime. Brother inscittifica le stampanti. Il ritorno di Digg. Queste e molte altre le notizie tech commentate nella puntata di questa settimana.Dallo studio distribuito di digitalia:Franco Solerio, Michele Di Maio, Francesco FacconiProduttori esecutivi:Federico Bruno, Giulio Gabrieli, Yoandi Herrera, Christian Masper, Simone Andreozzi, Giuliano Arcinotti, @Ppogo, Davide Tinti, Marco Caggianese, Corrado Bigliardi, Arzigogolo, Maurizio Verrone, Matteo Arrighi, Massimo Dalla Motta, Andrea Sinigaglia, Arnoud Van Der Giessen, Matteo De Lucia, Fabrizio Bianchi, @Akagrinta, Consultech Srl, Andrea Picotti, Christian Fabiani, @Jh4Ckal, Davide Capra, Simone Pignatti, @Lucatax, Alessio Conforto, Stefano Orso, Paolo Bernardini, Danilo Sia, Alessandro Lazzarini, Matteo Carpentieri, Roberto Barison, Alessio Tonioni, Manuel Zavatta, Edoardo Zini, Nicola Pedonese, Nicola Gabriele Del Popolo, Fiorenzo Pilla, Luca Barbetta, Massimiliano Casamento, Stefano Cutellè, Maurizio Galluzzo, Paolo Lucciola, Matteo Masconale, Massimiliano Saggia, Pasquale Maffei, Matteo Vivona (Indievault), ma7u, Francesco Paolo Sileno, Michele OlivieriSponsor:Links:How the Biggest Crypto Heist in History Went DownBybit ETH multisig cold wallet just made a transfer to our warm walletCrypto fans underwhelmed by Trump order creating US bitcoin reservePresident Donald J. Trump Establishes the Strategic Bitcoin ReserveYou knew it was coming: Google begins testing AI-only search resultsAmazon is reportedly developing its own AI 'reasoning' modelOpenAIs rumored $20000 agent plan explained.They're evolving - VideoGibberLink - AI-to-AI Sound ProtocolApple delays upgraded Siri: its taking longer than we thoughtMorto: l'ex superpoliziotto coinvolto nell'inchiesta sui dossieraggiL'altolà di Valditara sul registro elettronico. "No alle pubblicità"Prime Video lancia i primi contenuti doppiati con l'IAThe Last of Us season 2 gets an explosive new trailerHundreds of your Warner Bros DVDs probably dont work anymoreBrother denies using firmware updates to brick printers with 3rd-party inkBrother printers joins the Evil Empire, blocks third-party inkHow Google tracks Android device users before they've even opened an appMusic labels will regret coming for the Internet ArchiveThe Return of Digg, a Star of an Earlier Internet EraDigg Listens to DiggBar Complaints; Changes to ComeThe DiggBar Controversy | Ignite Social MediaTrailer - Torna la leggendaria Verdansk | Call of Duty: WarzoneAlmanacco Digitaliano 2024 su LedizioniAlmanacco Digitaliano su AmazonGingilli del giorno:Lenny Rachitsky intervista Matt Mullenweg di AutomatticPortmaster - gestisci i port direttamente dalla retro consoleiTerm 2 - terminal emulator for MacOS that does amazing thingsSupporta Digitalia, diventa produttore esecutivo.

Welcome to another episode of Supra Insider. This time, Ben and Marc sat down with Jacob Bank from Relay.app to dive into the rapidly evolving world of AI workflows, automation, and agent systems. Prior to founding Relay.app, Jacob was a Director of Product Management at Google, which he joined after Google acquired his former startup, Timeful.Jacob shares his firsthand experience building AI-driven workflows, what he's learned from experimenting with AI agents, and how PMs should be thinking about automation in their work. We explore the real-world challenges of implementing AI, why human-in-the-loop remains crucial, and how AI is transforming tasks like content creation, customer insights, and product management.We also discuss the role of AI in product strategy, how to evaluate what's possible today vs. what will be possible in the near future, and why PMs who don't actively experiment with AI risk falling behind. If you're trying to make sense of AI's impact on product work, this episode is for you.All episodes of the podcast are also available on Spotify, Apple and YouTube.New to the pod? Subscribe below to get the next episode in your inbox

Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Will Newton, Principal Product Architect at Amplitude. With years of experience at companies like Gusto and Feather, Will shares insights into how AI is transforming the design world—from prototyping workflows to the evolving roles within product teams. The conversation explores how AI tools are blurring roles between product managers, designers, and engineers while speeding up development cycles. If you're interested in AI's impact on product development, don't miss this episode!All episodes of the podcast are also available on Spotify, Apple and YouTube.New to the pod? Subscribe below to get the next episode in your inbox

Listen now on Apple, Spotify, and YouTube.This episode is brought to you by Amplitude — сheck new Guides and Surveys to deliver helpful, well-timed messages: https://amplitude.com/guides-and-surveys —Welcome to Growthmates with Kate Syuma — Growth Advisor, ex-Miro. This season, “In the Company of Women,” is about celebrating women who successfully balance work, family, and creative passions while building meaningful careers.Growthmates is a place to connect with inspiring leaders and help you grow—personally and professionally. Learn how companies like Dropbox, Adobe, Canva, Loom, and more build world-class products and growth cultures.In this episode, Kate Syuma and Elena Verna dive into a conversation about career evolution, growth strategies, and navigating transitions. With experience at SurveyMonkey, Miro, Dropbox, Reforge, and Malwarebytes, Elena shares her journey from leading growth at major companies to building a successful solopreneurship and transitioning back to a full-time role.They explore the non-linear career shifts, defining your "superpower zone," and setting boundaries for sustainable success. Elena also breaks down how companies can move from product-led growth to product-led sales, sharing insights on recognizing early signals and layering strategies for long-term growth.

Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Colin Matthews, instructor of two popular AI prototyping courses on Maven. Colin shared his insights on the evolving landscape of AI-powered prototyping tools and how product managers can leverage them to build and test more impactful features faster.The discussion explored different categories of AI prototyping tools, when to use them, and how they're changing the way teams collaborate. Colin also walked us through a live demo, showing how to prototype and test a new hypothetical AI LinkedIn feature in real time. If you're a PM looking to move faster and validate ideas more efficiently, this episode is for you.All episodes of the podcast are also available on Spotify, Apple and YouTube.New to the pod? Subscribe below to get the next episode in your inbox

Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Yue Zhao, a former product leader at Thumbtack, Instagram, Meta, and Fuzzy, who now thrives as an executive coach and author. Yue shares her story of moving to Barcelona, exploring new career paths, and writing a book that reshaped her outlook on work and leadership. They dive into key topics like navigating career pivots, staying energized through curiosity, and learning to reframe limiting beliefs.Whether you're a product leader considering new career paths or someone seeking actionable tips for personal growth, this conversation is packed with insights.All episodes of the podcast are also available on Spotify, Apple and YouTube.New to the pod? Subscribe below to get the next episode in your inbox

Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Irene Yu, founder and CEO of Skiplevel, professional training designed to teach PMs how to become more technical without learning to code. In this conversation, they explored Irene's journey from Amazon engineer to entrepreneur, the communication challenges between PMs and engineers, and how Skiplevel is helping mitigate those challenges. They also discussed the rise of AI features in product development, exploring how PMs can handle edge cases, learn critical AI concepts, and avoid the dreaded "demo trap." Irene also revealed how she used AI to build a personalized therapist and life coach. This episode is packed with valuable takeaways for PMs, engineers, and product leaders looking to level up their collaboration and technical skills.All episodes of the podcast are also available on Spotify, Apple and YouTube.New to the pod? Subscribe below to get the next episode in your inbox

Jonny Miller is the creator of Nervous System Mastery. It teaches evidence-backed protocols to cultivate calm, build resilience, and increase aliveness in 45 days. It's a five-week, cohort-based course that is just wrapping up its sixth cohort in the last three years. In those six cohorts, Jonny has served nearly 1,000 students and earned more than $800,000. Here's the best part – Jonny doesn't have a massive audience. When he launched Nervous System Mastery, he had a couple thousand followers on Twitter and a small email list. This is the magic of a well-designed Signature Product – and Jonny is the perfect example. In this episode, we get into the weeds about how he's grown NSM – what's worked well, what hasn't, and how he's found himself on large podcasts with people like Lenny Rachitsky, Ali Abdaal, Chris Williamson, and more. → Join Nervous System Mastery Full transcript and show notes Jonny's Website / Twitter / Instagram / LinkedIn *** RECOMMENDED NEXT EPISODE → #221: Ryan Hawk – Anatomy of a $12,500 membership earning $400,000+ per year *** ASK CREATOR SCIENCE → Submit your question here *** WHEN YOU'RE READY

My guest today is someone special to me: Bruce McCarthy.Bruce has probably seen and helped more companies with product roadmaps than anyone in the world.He's the author of the best-selling book "Product Roadmaps Relaunched" and has just launched his new book Aligned: Stakeholder Management for Product Leaders.Bruce and I met in Madrid a couple of years ago. Our first 1:1 was over breakfast, where we talked about different things - including the new book he was writing at the time.I knew immediately that it would be a very relevant book for many folks...  And as Lenny Rachitsky puts it now in his review, this book is "Your guide to building exceptional stakeholder relationships".This episode is a mini-masterclass on how to manage stakeholders and how to foster alignment in your organization.We discussed:* Why OKRs and Roadmaps are great tools to drive alignment - and how to do them well* Real case examples and lessons learned on how to align stakeholders* The importance of having collective outcomes and cross-functional collaboration* Practical tips and habits for succeeding with stakeholder management* Mental models, frameworks, and practices for effective decision making* Why org charts tell us very little about who makes decisions* And more! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit afonsofranco.substack.com

Ep. 238 Are you tired of spending your advertising budget on the same stale channels?  Kipp and Kieran dive into the untapped marketing channels that pro marketers are leveraging to gain a competitive edge. Learn more on the potential of working with creators, the overlooked benefits of YouTube ads, and the power of point-of-need advertising to reach your audience in high-engagement moments. Discover how these innovative strategies can amplify your brand's reach and skyrocket your ROI in this must-listen episode of Marketing Against the Grain. Mentions Grab HubSpot's free AI-Powered Customer Platform and watch your business grow https://clickhubspot.com/cmt FREENOW https://www.free-now.com/uk/ Lenny Rachitsky https://x.com/lennysan Grammarly https://www.grammarly.com/ A Clockwork Orange https://en.wikipedia.org/wiki/A_Clockwork_Orange_(film) Resource [Free] Steal our favorite AI Prompts featured on the show! Grab them here: https://clickhubspot.com/aip We're on Social Media! Follow us for everyday marketing wisdom straight to your feed YouTube: ​​https://www.youtube.com/channel/UCGtXqPiNV8YC0GMUzY-EUFg  Twitter: https://twitter.com/matgpod  TikTok: https://www.tiktok.com/@matgpod  Join our community https://landing.connect.com/matg Thank you for tuning into Marketing Against The Grain! Don't forget to hit subscribe and follow us on Apple Podcasts (so you never miss an episode)! https://podcasts.apple.com/us/podcast/marketing-against-the-grain/id1616700934   If you love this show, please leave us a 5-Star Review https://link.chtbl.com/h9_sjBKH and share your favorite episodes with friends. We really appreciate your support. Host Links: Kipp Bodnar, https://twitter.com/kippbodnar   Kieran Flanagan, https://twitter.com/searchbrat  ‘Marketing Against The Grain' is a HubSpot Original Podcast // Brought to you by The HubSpot Podcast Network // Produced by Darren Clarke.

Key Takeaways from H1 2024: Reflecting on Hardware, Unstructured Data, and the Future of Product Management In the season 2 finale of 'Unsolicited Feedback,' co-hosts Brian Balfour, Ravi Mehta, and Joff Redfern join Fareed Mosavat to reflect on the most compelling topics of the season. They start with discussions on how trends diverge between hardware and software markets, and the distinctions between luxury and premium products. The episode takes a deep dive into AI's role in revolutionizing unstructured data and its far-reaching effects on product management. Touching on methodology changes, the hosts contemplate how AI might transform the software development life cycle and what it means for the future roles of product managers, designers, and engineers, giving some Unsolicited Feedback to our friend Lenny Rachitsky along the way. Show Notes: Fareed mentioned that Reforge has just launched a brand new AI product, the Reforge Extension, now in public beta. Ever wish you could get expert feedback from leaders like Fareed, Brian Balfour, Andrew Chen, and Elena Verna while working on your documents? Now you can! He also mentioned our free AI festival, ref:AI, a full-day virtual conference delving into all things AI, featuring a special episode of Unsolicited Feedback with the legendary Andrew Chen. Secure your spot now as spaces are limited. Register here today. And, last but not least, Rupa Chaturvedi & Polly Allen (renowned industry experts with expertise in Generative AI from Amazon's Alexa, Google and Uber) are teaching Generative AI Products: How to get from Idea to MVP for the 3rd time starting on June 14. It's a 3-week course designed to get you started on your journey of leading AI initiatives and projects that involve Generative AI. Check out a full summary of the takeaways and lessons from this episode at ➡️ https://www.unsolicitedfeedback.co/ 00:00 Season Finale Introduction 03:50 Luxury in Software and Physical Goods 18:16 AI's Impact on Product Management 30:29 AI vs Human Intuition in Strategy 38:11 The Role of AI in Communication and Empathy 41:19 Revolutionizing the Software Development Life Cycle 52:25 The Rise of Full-Stack Product Leaders Check out a full summary of the takeaways and lessons from this episode at ➡️ https://www.unsolicitedfeedback.co/

A couple of months ago, Ben wrote a thought-provoking LinkedIn post about the potential damage Marty Cagan's advice on Lenny's podcast could cause to feature factory PMs. This sparked a conversation between Ben and Estee Goldschmidt on The Estee Show, which caught the attention of Lenny Rachitsky. Recognizing the importance of the topic, Lenny invited Ben to write a guest post for his newsletter, "In defense of feature team product managers," which went live today.New to the pod? Subscribe below to get the next episode in your inbox

Chenell is the writer of Growth In Reverse, a weekly newsletter where she reverse engineers how a top creator grew from 0 to 50k+ subscribers. Chenell has done deep dives on Justin Welsh, Codie Sanchez, Lenny Rachitsky, Harry Dry, and many more. I read it every week and think it's incredibly well-done. The premise is super clear, and as a result, Chenell has seen her OWN newsletter grow very quickly – nearing 10,000 subscribers in just about four months. In this episode, you'll learn: The common patterns between these newsletter operators Some of the most effective growth tactics she's uncovered And what's working for HER right now Full transcript and show notes Follow Chenell on Twitter / LinkedIn Subscribe to Growth In Reverse *** CONNECT

Emilie Gerber is the founder and CEO of Six Eastern, a top PR agency that's worked with over 100 tech companies, from stealth startups to publicly traded companies. Before starting her own firm, she worked at Uber, where she led PR for the business development team and B2B programs. Prior to that, she worked at Box on product communications, with a focus on product launches and partnership announcements. In our conversation, we discuss:• Why, and when, getting press is worth your time• Common misconceptions about the impact press can have• The second-order effects of press• Which areas each publication (TechCrunch, Axios, The Verge, etc.) cares most about• How to craft your pitch• How to find and reach reporters• How pitching press is different from pitching customers• The effectiveness of direct communication through social media versus traditional press—Brought to you by:• Sprig—Build a product people love• Eppo—Run reliable, impactful experiments• Vanta—Automate compliance. Simplify security.—Find the transcript for this episode and all past episodes at: https://www.lennyspodcast.com/episodes/. Today's transcript will be live by 8 a.m. PT.—Where to find Emilie Gerber:• Substack: http://onbackgroundintel.substack.com• LinkedIn: https://www.linkedin.com/in/emilie-gerber-59612230/• Website: https://sixeastern.com/• Email: hello@sixeastern.com—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Emilie's background(04:56) The value of press and second-order effects(13:00) When press is not worth your time(17:01) Different publications and their suitability(25:36) Avoiding negative stories(27:23) Finding aligned podcasts and awards(31:12) Advice for reaching out to reporters(37:23) Controversial pitches(41:16) Avoiding category creation(43:26) Examples of pitches that have worked well(53:32) Pitching to Lenny(55:46) Effective pitching strategies(57:45) Improving pitch announcements(01:03:01) Press releases(01:07:06) Crafting a compelling story(01:09:43) Traditional press vs. newsletters, podcasts, and social media(01:15:50) Building a social media presence(01:17:51) How to get a Morning Brew feature(01:19:32) Advice on choosing a PR agency(01:22:25) Timing and budget for PR(01:25:39) Lightning round—Referenced:• Perplexity: https://www.perplexity.ai/• Who is Lenny Rachitsky? And what does he know that you don't about making millions writing online?: https://www.fastcompany.com/90940453/lenny-rachitsky-newsletter-podcast-job-board-substack• 42-year-old brings in an average of $41,000 a month from his podcast and works on it just 5 hours a week: https://www.cnbc.com/2024/01/11/lenny-rachitsky-podcast-brings-in-more-than-500k-a-year-heres-how.html• How This Newsletter Writer Got More Than 300,000 Subscribers, and Now Makes “Significantly More” Than He Did at His Day Job: https://www.entrepreneur.com/starting-a-business/how-this-newsletter-writer-got-more-than-300000/447172• Business Insider: https://www.businessinsider.com/• Contraline: https://www.contraline.com/• Forbes: https://www.forbes.com/• TechCrunch: https://techcrunch.com/• Axios: https://www.axios.com/• Fortune: https://fortune.com/• Term Sheet: https://fortune.com/tag/term-sheet/• The Verge: https://www.theverge.com/• Wall Street Journal: https://www.wsj.com/• New York Times: https://www.nytimes.com/• Found podcast: https://techcrunch.com/tag/found/• Equity podcast: https://techcrunch.com/tag/equity-podcast/• VentureBeat: https://venturebeat.com/• Fast Company: https://www.fastcompany.com/• Clockwise: https://www.getclockwise.com• Shopify deleted 322,000 hours of meetings. Should the rest of us be jealous?: https://www.npr.org/2023/02/15/1156804295/shopify-delete-meetings-zoom-virtual-productivity• Shopify canceled all recurring meetings. Should you too?: https://www.getclockwise.com/blog/shopify-cancels-meetings• Shopify's new meeting cost calculator is well intentioned—but it's not addressing the issue: https://www.fastcompany.com/90930137/shopifys-new-meeting-cost-calculator-is-well-intentioned-but-its-not-addressing-the-issue• Matt Martin on LinkedIn: https://www.linkedin.com/in/voxmatt/• Ramp: https://ramp.com/welcome• Corporate card start-up Ramp targets Bill.com with free payments software: https://www.cnbc.com/2021/10/26/corporate-cards-ramp-targets-billcom-with-free-payments-software.html• Bill: https://www.bill.com/• Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennyspodcast.com/velocity-over-everything-how-ramp-became-the-fastest-growing-saas-startup-of-all-time-geoff-charl/• Column Tax: https://www.columntax.com/• Propel: https://www.joinpropel.com/• Gamma: https://gamma.app/• Gamma brings in $7M to bring the slide deck into the 21st century: https://techcrunch.com/2021/10/28/gamma-brings-in-7m-to-bring-the-slide-deck-into-the-21st-century/• NewBank: https://www.newbankusa.com/• Backed by a16z, Relay races to market with Zapier in its crosshairs: https://techcrunch.com/2023/10/11/relay-a16z-zapier-google/• Zapier: https://zapier.com/• Rajiv Ayyangar's thread on X about tag lines: https://twitter.com/rajivayyangar/status/1758179077629100482• Entropy: https://entropytechnologydesign.com/• Money 20/20: https://www.money2020.com/• Jim Bankoff on LinkedIn: https://www.linkedin.com/in/jimbankoff/• Ramping Up: https://www.notboring.co/p/ramping-up• Aaron Levie on LinkedIn: https://www.linkedin.com/in/boxaaron/• Aaron Levie on X: https://twitter.com/levie• Duolingo on TikTok: https://www.tiktok.com/@duolingo• Morning Brew: https://www.morningbrew.com/• Tech Brew: https://www.emergingtechbrew.com/• HR Brew: https://www.hr-brew.com/• Mark Zuckerberg on Morning Brew Daily: https://www.youtube.com/watch?v=xQqsvRHjas4&t=1309s• How to Change Your Mind: What the New Science of Psychedelics Teaches Us About Consciousness, Dying, Addiction, Depression, and Transcendence: https://www.amazon.com/Change-Your-Mind-Consciousness-Transcendence/dp/1594204225• The Walking Dead on Netflix: https://www.netflix.com/title/70177057• Yellowjackets on Paramount+: https://www.paramountplus.com/shows/yellowjackets/• The Last of Us on HBO: https://www.hbo.com/the-last-of-us• Apple Vision Pro: https://www.apple.com/apple-vision-pro• TNB Tech Minute: Startup Perplexity Challenges Google With AI Search: https://www.wsj.com/podcasts/tech-news-briefing/tnb-tech-minute-startup-perplexity-challenges-google-with-ai-search/984362d5-a8f0-48b4-8b55-ad7e570a74d2—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Noam Lovinsky has had a distinguished career in product, leaving an indelible mark at Facebook, YouTube, Thumbtack, and currently as the chief product officer at Grammarly. At Facebook, Noam helped establish the New Product Experimentation team; at Thumbtack, he was chief product officer; and at YouTube, he was one of the early product leaders overseeing the consumer experience. In our conversation, we discuss:• Challenges and lessons from reviving growth at YouTube and Thumbtack• Lessons from building Facebook's New Product Experimentation team• Insights into Grammarly's success• Knowing when it's time to kill your project• Why diversifying your growth channels is critical• The power of visioning and storytelling in shaping product strategy• How to create space for innovation at large companies• The resilience and motivation of Grammarly's team in Ukraine—Brought to you by:• Whimsical—The iterative product workspace• Vanta—Automate compliance. Simplify security.• LinkedIn Ads—Reach professionals and drive results for your business—Find the full transcript at: https://www.lennyspodcast.com/the-happiness-and-pain-of-product-management-noam-lovinsky-grammarly-facebook-youtube-thumbtac/—Where to find Noam Lovinsky:• X: https://twitter.com/noaml• LinkedIn: https://www.linkedin.com/in/noaml/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Noam's background(04:18) Noam's lack of online presence(08:06) Lessons from YouTube: advocating for what's best for yourself and the team(14:31) Prioritizing what's best for the business(19:37) Knowing when it's time to kill a project(21:47) Lessons from Thumbtack: diversifying growth channels and overcoming challenges(26:24) How Thumbtack turned growth around(31:44) Building Airbnb's instant booking feature(35:28) Lessons from Thumbtack: team collaboration and product strategy(38:38) Lessons from Facebook: building the New Product Experimentation team(40:43) The importance of starting small and building community density(46:07) Advice for building a startup within a startup(48:52) Having an incentive system(49:34) Lessons from Grammarly: adapting to changing user needs and building for the masses(54:20) The scrappiness and profitability of Grammarly(56:56) The resilience and motivation of the Grammarly team in Ukraine(59:08) General career advice(01:01:02) When to pull back(01:02:58) Closing thoughts(01:03:56) Lightning round—Referenced:• Substack: https://substack.com/• Hunter Walk on LinkedIn: https://www.linkedin.com/in/hunterwalk/• The rituals of great teams | Shishir Mehrotra of Coda, YouTube, Microsoft: https://www.lennyspodcast.com/the-rituals-of-great-teams-shishir-mehrotra-coda-youtube-microsoft/• Salar Kamangar on LinkedIn: https://www.linkedin.com/in/salar-kamangar-5a059712/• Grammarly: https://www.grammarly.com/• Thumbtack: https://www.thumbtack.com/• FRED on YouTube: https://www.youtube.com/FRED• How Airbnb Proved That Storytelling Is the Most Important Skill in Design: https://www.inc.com/yazin-akkawi/the-surprising-technique-airbnb-uses-to-better-sell-an-experience.html• Google+: https://en.wikipedia.org/wiki/Google%2B• Marco Zappacosta on LinkedIn: https://www.linkedin.com/in/marcozappacosta/• Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier/• Whitney Steele on LinkedIn: https://www.linkedin.com/in/whitneydsteele/• David Shein on LinkedIn: https://www.linkedin.com/in/davidshein/• The magic of thinking big, by Lenny Rachitsky: https://www.mindtheproduct.com/the-magic-of-thinking-big-by-lenny-rachitsky/• What Seven Years at Airbnb Taught Me About Building a Business: https://www.lennysnewsletter.com/p/what-seven-years-at-airbnb-taught• New apps, new experiences: NPE Team, from Facebook: https://tech.facebook.com/engineering/2019/7/npe-team-from-facebook/• The Origin Story of the BRC Trash Fence: https://journal.burningman.org/2016/05/black-rock-city/leaving-no-trace/the-origin-story-of-the-brc-trash-fence/• Nike opens high-tech research and innovation lab: https://www.just-style.com/news/nike-opens-high-tech-research-and-innovation-lab/• ChatGPT: https://chat.openai.com/• Microsoft Copilot: https://copilot.microsoft.com/• How to grow a subscription business | Yuriy Timen (Grammarly, Canva, Airtable): https://www.lennyspodcast.com/how-to-grow-a-subscription-business-yuriy-timen-grammarly-canva-airtable/• “The cave you fear to enter holds the treasure you seek”: https://gointothestory.blcklst.com/the-cave-you-fear-to-enter-holds-the-treasure-you-seek-d624e28c3848• Build: An Unorthodox Guide to Making Things Worth Making: https://www.amazon.com/Build-Unorthodox-Guide-Making-Things/dp/0063046067• For All Mankind on AppleTV+: https://tv.apple.com/us/show/for-all-mankind/umc.cmc.6wsi780sz5tdbqcf11k76mkp7• Fargo TV series on Hulu: https://www.fxnetworks.com/shows/fargo• Arc browser: https://arc.net/• Competing with giants: An inside look at how The Browser Company builds product | Josh Miller (CEO): https://www.lennyspodcast.com/competing-with-giants-an-inside-look-at-how-the-browser-company-builds-product-josh-miller-ceo/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Episode 113: Today's read is by one of my favorite startup creators, Lenny Rachitsky. The essay, How To Kickstart & Scale a Consumer Business, breaks down the seven proven strategies to acquire your first 1,000 users as a B2C startup. I'm going to read through each of the strategies, share some examples that Lenny provides, and provide some of my own thoughts on early growth. Original essay: https://www.lennysnewsletter.com/p/consumer-business-find-first-users Send us an email and let us know what you think of the idea! foundersjournal@morningbrew.com #FoundersJournal #Startups #Entrepreneur Listen to Founder's Journal here: https://link.chtbl.com/OV4W93_W Watch Founder's Journal here: https://www.youtube.com/@FoundersJournal/  Subscribe to Morning Brew! Sign up for free today: https://bit.ly/morningbrewyt Follow The Brew! Instagram - https://www.instagram.com/morningbrew/ Twitter - https://twitter.com/MorningBrew Tik Tok - https://www.tiktok.com/@morningbrew Follow Alex! Alex Lieberman (@businessbarista) Learn more about your ad choices. Visit megaphone.fm/adchoices

On this week's show, we explore a variety of topics. Ben wants to perform a mini retrospective on his desire to support the legacy platform at work. Carol is feeling isolated as the only engineer on her team - her dog is a good listener, but isn't very helpful when it comes to brainstorming. And, Adam wants to talk about the browser landscape; and see which browser(s) everyone is currently using.Also, Ben offers up some high praise for Lenny's Podcast - a show in which Lenny Rachitsky interviews top Product and Marketing leaders in our industry. This show is absolutely dripping in value!Follow the show and be sure to join the discussion on Discord! Our website is workingcode.dev and we're @WorkingCodePod on Twitter and Instagram. New episodes drop weekly on Wednesday.And, if you're feeling the love, support us on Patreon.With audio editing and engineering by ZCross Media.Full show notes and transcript here.

Episode 100: On this episode, I'll be sharing the best moments from Lenny Rachitsky's recent interview with Brian Chesky, the co-founder & CEO of Airbnb. Airbnb is a $95bn company that under Brian's leadership has grown into a community of 4 million hosts welcoming over 1.5 billion guests across 220 countries. These moments range from how politics & bureaucracy are created in a company to surviving near-business death in 2020 to how Brian has grown as a CEO since day 1.  Send us an email and let us know what you think of the idea! foundersjournal@morningbrew.com #FoundersJournal #Startups #Entrepreneur Listen to Founder's Journal  here: https://link.chtbl.com/OV4W93_W Watch Founder's Journal here: https://www.youtube.com/@FoundersJournal/  Subscribe to Morning Brew! Sign up for free today:  https://bit.ly/morningbrewyt Follow The Brew! Instagram - https://www.instagram.com/morningbrew/ Twitter - https://twitter.com/MorningBrew Tik Tok - https://www.tiktok.com/@morningbrew Follow Alex! Alex Lieberman (@businessbarista) Learn more about your ad choices. Visit megaphone.fm/adchoices

On this episode of Christopher Lochhead: Follow Your Different, we are joined by one of my favorite people in the creator world, Lenny Rachitsky. A few episodes back, we posted the conversation we had on Lenny's Podcast were I also extended an invite to him for a dialogue at Follow Your Different. And now, here we are. Lenny Rachitsky specializes in deeply researched product growth and career advice, particularly for those in the startup/tech world. Lenny's newsletter on Substack is also the number one paid business Substack. Try as we might with Category Pirates, we've been unable to catch him, and I think that's great. There are some powerful learnings here for marketers, and creators, and really anybody who wants to design a legendary career, I think you're going to absolutely love this very special conversation with Lenny. You're listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let's go. Lenny Rachitsky on Product Management and Growth Strategies The conversation begins with Christopher praising Lenny's approach to product management and growth, hailing him as the "category King." They then discuss the value of staying broad versus niche in product management, with Lenny expressing admiration for specific experts like Emily Kramer in marketing. Christopher commends Lenny for his unique, non-egotistical approach in a field filled with "hustle porn stars." Lenny attributes his success to providing genuine value rather than chasing followers. Christopher perceives a cohesive through line in Lenny's work, suggesting a continuous quest to answer key questions for founders and product builders. Lenny elaborates on his goal of addressing a broad range of questions in product management and growth, emphasizing a core focus with intersecting adjacencies like career and leadership. Creating Valuable Content through Practical Application of Ideas Lenny continues to discuss his approach on content creation, emphasizing the importance of maintaining diverse interests to keep himself engaged. Christopher Lochhead praises Lenny for incorporating varied topics into his work, appealing to a broader audience beyond the core niche of product management. From there, they explore the concept of obvious and non-obvious content, with Lenny acknowledging the practical nature of his content. Christopher notes the challenge of balancing obviousness with depth, expressing his preference for content that goes beyond the blatantly evident. Despite categorizing Lenny's content as somewhat obvious, Christopher commends him for avoiding the realm of "stupid obvious," recognizing the valuable and practical applications within Lenny's work. Lenny Rachitsky on Creating Quality Content Following up on this, Christopher questions Lenny Rachitsky on creating smart, obvious, and practical content without it being overly simplistic. Lenny attributes his success to maintaining a high bar for quality, ensuring content is not overly obvious or uninteresting. He emphasizes spending extensive time on each post, sometimes up to 100 hours, and credits his ability to dedicate full time to content creation as a significant advantage. Lenny describes a flywheel effect where initial success allows more time for improvement, creating a cycle of growth. He suggests that anyone can follow this model if they find the time and opportunities to invest in their content. To hear more from Lenny and his ideas and thoughts on business content creation, download and listen to this episode. Bio Lenny Rachitsky (author of #1 business newsletter on Substack with 500k+ subscribers) interviews world-class product leaders and growth experts to uncover concrete, actionable, and tactical advice to help you build, launch, and grow your own product. Links Connect with Lenny Rachitsky! Lenny's Website | Lenny's Podcast | Twitter/X | LinkedIn

Sid Yadav is the Co-founder and CEO of Circle, the all-in-one community platform trusted by creators like Tiago Forte, David Perell, and Miles Snider. Sid started the tech blog Rev2 when he was a teenager in New Zealand, writing about the launch of YouTube and the iPhone. He was the founding engineer and designer of Teachable, which he helped scale to +25m+ in ARR before it was acquired in 2020. He started Circle in 2019 with co-founders Rudy Santino and Andrew Guttormsen, which they scaled to $16m in ARR by December of 2023. Circle has since raised $31m from Investors like Tiger Global, Notation Capital, Bungalow, Todd Goldberg, Rahul Vohra, Scott Belsky, Josh Buckley, Ankur Nagpal, Wade Foster, and Dharmesh Shah. Sid immigrated with his family from India to New Zealand as a teenager and to the US after college. His story is a perfect encapsulation of the American Dream, and I'm excited to share this conversation. — — — — Brought to you by Deel, the global HR + payroll platform used by 20,000+ teams. Deel's in-house immigration team gets you and your team worldwide visas without the legwork. Book a Demo: bit.ly/thepeelxdeel — — — — Topics discussed include: (03:53) Why the creator economy is booming despite negative sentiment (13:22) Writing a popular tech blog as a teen in the mid 00's (23:16) Joining Teachable as the 2nd employee (40:30) Why Teachable CEO Ankur Nagpal invested 90% of his liquid net worth in Circle's $1.7m Pre-seed round (48:44) Sid's inside view at the creator economy before, during, and after COVID (52:50) The magic of Lenny Rachitsky's creator flywheel (56:10) The reason Sid raised a Seed from lots of investors instead of one large check (01:14:30) Inside raising a Series A from Tiger Global in 2021 (01:22:19) Why Sid writes an investor update every month (01:25:15) Going from Zero to $16m ARR in four years (01:27:28) How Circle approaches its product roadmap (01:29:20) Building a community around your product (01:37:03) Advice for running a remote-first team (01:46:54) How Sid convinced the founder of Zapier to be his CEO coach (01:54:20) Why founders need to deal with reality Referenced: https://circle.so/ https://www.teachable.com “Cost of a meeting” tweet: https://twitter.com/0xgaut/status/1620815168921038850 Tiago Forte Building a Second Brain: https://www.buildingasecondbrain.com/foundation PARA Method: https://fortelabs.com/blog/para/ Lenny's interview with Brian Chesky: https://www.youtube.com/watch?v=4ef0juAMqoE Turner's interview with Wade Foster, Co-founder and CEO of Zapier:  https://youtu.be/NJMjuYt9jEc Myles Snyder: https://mylessnider.com/ Where to find Sid: Twitter: https://twitter.com/sidyadav LinkedIn: https://www.linkedin.com/in/sidyadav Where to find Turner: Newsletter: https://www.thespl.it Twitter: https://twitter.com/TurnerNovak Banana Capital: https://bananacapital.vc

This week on Christopher Lochhead: Follow Your Different, we're presenting to you Christopher's appearance on Lenny's Podcast, hosted by Lenny Rachitsky. Lenny Rachitsky runs the #1 Business Substack newsletter, Lenny's Newsletter. It is legendary especially for people in tech marketing, product marketing, and startups. It's so legendary that even Christopher pays for it. And now, he's in it. This is one of the more in-depth discussions Christopher has had with a very smart person about category design in a while. So settle in for a good listen and great lesson about category design. You're listening to Christopher Lochhead: Follow Your Different. We are the real dialogue podcast for people with a different mind. So get your mind in a different place, and hey ho, let's go. This episode originally aired on Lochhead on Marketing episode 187. If you want to hear more insights on marketing and category design from Christopher, feel free to check it out at Lochhead on Marketing and anywhere you listen to podcasts. On taking the Good with the Bad Lenny starts off the conversation by showing appreciation to Christopher's extensive work, and jokingly adds that it was challenging to prepare for their conversation due to his numerous podcasts, books, and other content. That said, Lenny noticed Christopher's website displayed negative reviews prominently. When asked about it, Christopher explained his approach with humor, calling his team Category Pirates and embracing criticism. He believed it was essential for innovators not to fear criticism, citing examples of famous artists and musicians who faced initial negativity. Christopher displayed the negative feedbacks to show the reality of creative work and to remind people not to take themselves too seriously. Lenny admired Christopher's ability to handle criticism and expressed the desire to adopt a similar mindset. Lenny Rachitsky on how Lenny's Newsletter came to be Christopher Lochhead expressed admiration for Lenny's branding choices, appreciating the simplicity of just being called “Lenny.” He found it endearing and highlighted that Lenny's authenticity stood out in a world where many influencers create an aura of superiority. Lenny shared that the name “Lenny's Newsletter” was a default suggestion from Substack, and he never intended it to be a long-term commitment. Similarly, he struggled to find a different name for his podcast, wanting to avoid a self-centered approach. But despite having his name in the branding, Christopher noted the content wasn't self-centered; instead, it reflected Lenny's genuine approach, unlike influencers who focus on creating envy. They both appreciated the authenticity in Lenny's approach. Lenny Rachitsky and Christopher Lochhead talk Category Creation Lenny asked Christopher about category creation, a concept Christopher has championed over competition in existing markets. Christopher explained how most people aim to compete by offering a better product or service in an existing category. However, legendary innovators don't follow this path. They create entirely new categories, defining unique problems and solutions. Christopher emphasized that a single company in a category usually captures two-thirds of the market value, making category creation a lucrative strategy. He cited Gojo Industries, creators of Purell, as an example. They didn't just invent hand sanitizer; they redefined the problem of hand cleanliness, leading to a new market category. Christopher stressed the importance of focusing on problem-solving rather than just product features, making one's brand irreplaceable in customers' minds. He contrasted this approach with typical marketing, where companies invite comparison, emphasizing the power of radical differentiation and being a category creator. To hear more about Christopher's conversation with Lenny Rachitsky on Category Creation, download and listen to this episode. If you want to learn more about Lenny Rachitsky...

This week, we're presenting to you Christopher Lochhead's appearance on Lenny's Podcast, hosted by Lenny Rachitsky. Lenny Rachitsky runs the #1 Business Substack newsletter, Lenny's Newsletter. It is legendary especially for people in tech marketing, product marketing, and startups. It's so legendary that even Christopher pays for it. And now, he's in it. This is one of the more in-depth discussions Christopher has had with a very smart person about category design in a while. So settle in for a good listen and great lesson about category design. Welcome to Lochhead on Marketing. The number one charting marketing podcast for marketers, category designers, and entrepreneurs with a different mind. On taking the Good with the Bad Lenny starts off the conversation by showing appreciation to Christopher's extensive work, and jokingly adds that it was challenging to prepare for their conversation due to his numerous podcasts, books, and other content. That said, Lenny noticed Christopher's website displayed negative reviews prominently. When asked about it, Christopher explained his approach with humor, calling his team Category Pirates and embracing criticism. He believed it was essential for innovators not to fear criticism, citing examples of famous artists and musicians who faced initial negativity. Christopher displayed negative feedback to show the reality of creative work and to remind people not to take themselves too seriously. Lenny admired Christopher's ability to handle criticism and expressed the desire to adopt a similar mindset. Lenny Rachitsky on how Lenny's Newsletter came to be Christopher Lochhead expressed admiration for Lenny's branding choices, appreciating the simplicity of just being called "Lenny." He found it endearing and highlighted that Lenny's authenticity stood out in a world where many influencers create an aura of superiority. Lenny shared that the name "Lenny's Newsletter" was a default suggestion from Substack, and he never intended it to be a long-term commitment. Similarly, he struggled to find a different name for his podcast, wanting to avoid a self-centered approach. But despite having his name in the branding, Christopher noted the content wasn't self-centered; instead, it reflected Lenny's genuine approach, unlike influencers who focus on creating envy. They both appreciated the authenticity in Lenny's approach. Lenny Rachitsky and Christopher Lochhead talk Category Creation Lenny asked Christopher about category creation, a concept Christopher has championed over competition in existing markets. Christopher explained how most people aim to compete by offering a better product or service in an existing category. However, legendary innovators don't follow this path. They create entirely new categories, defining unique problems and solutions. Christopher emphasized that a single company in a category usually captures two-thirds of the market value, making category creation a lucrative strategy. He cited Gojo Industries, creators of Purell, as an example. They didn't just invent hand sanitizer; they redefined the problem of hand cleanliness, leading to a new market category. Christopher stressed the importance of focusing on problem-solving rather than just product features, making one's brand irreplaceable in customers' minds. He contrasted this approach with typical marketing, where companies invite comparison, emphasizing the power of radical differentiation and being a category creator. To hear more about Christopher's conversation with Lenny Rachitsky on Category Creation, download and listen to this episode. If you want to learn more about Lenny Rachitsky, check out his Newsletter and Podcast at LennyRachitsky.com. Don't forget to grab a copy (or gift!) of one of our best-selling books:  Snow Leopard: How Legendary Writers Create A Category Of One  The Category Design Toolkit: Beyond Marketing: 15 Frameworks For Creating & Dominating Your Niche

Lenny writes one of the top five business newsletters on Substack — which has amassed over 500,000 subscribers. He hosts a podcast that makes him more money than he made in corporate America. And he's built a raving X audience of over 188,000. No training. No ego. And to top it all off, he writes in one of the most oversaturated markets on the Internet: product management. How does he do it? After his first Substack post went viral, “What Seven Years at Airbnb Taught Me About Building a Business”, Lenny saw the positive impact that his ideas had on his readers. He became obsessed with adding value. His motto? “There's always room for better content.” In an age of cheap, viral-hungry clickbait, Lenny's quality bar is through the stratosphere. He spends hours researching and revising. He takes ten, twenty, thirty passes on every piece he writes. He's hyper-focused on adding value. And his audience loves it. His commitment to quality catapults his content above the noise.  In this episode, you'll see inside Lenny's process. He opens up about creating high-signal content; following what energizes him; balancing storytelling with practicality; protecting his writing schedule; and above all, rising above the noise.  Twitter: https://twitter.com/lennysan Website: https://www.lennyrachitsky.com Newsletter: https://www.lennysnewsletter.com Podcast: https://www.lennyspodcast.com Want to learn more about the next course with Write of Passage? Click here: https://writeofpassage.school/hiw Want to learn more about How I Write? Website: https://writeofpassage.school/how-i-write/ YouTube: https://www.youtube.com/@DavidPerellChannel/videos Apple: https://podcasts.apple.com/us/podcast/how-i-write/id1700171470 Spotify: https://open.spotify.com/show/2DjMSboniFAeGA8v9NpoPv Learn more about your ad choices. Visit megaphone.fm/adchoices

Today we welcome Lenny Rachitsky to Making Media. Lenny has built the biggest business publication on Substack, "Lenny's Newsletter," with well over 500,000 readers. It started in 2019 as an advice column and since starting the newsletter, he has built a thriving podcast, community, and job board. Lenny's world has become the destination for product and growth people at companies big and small across the world. We explore his journey, the strategy behind his products or SKUs as he calls them, and we delve into his mindset which is particularly unique for someone who has been this successful at building an audience. I hope you enjoy our conversation with Lenny Rachitsky. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ----- Making Media is a property of Colossus, LLC. For more episodes of Making Media, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @ReustleMatt | @domcooke | @MakingMediaPod | @JoinColossus  Show Notes  (00:01:53) - (First question) - How Lenny tackles challenges through research, delivering actionable insights (00:05:04) - Juggling weekly and long-term posts, correlating effort to engagement (00:08:01) - How his varied experiences shaped his online content journey (00:11:54) - Maintaining relevance by advising companies & addressing problems (00:13:34) - How he aims to sustain his content creation without corporatizing (00:16:53) - Quantifying podcast success monetarily and by growth (00:19:43) - Evaluating post quality and striving for non-obvious, surprising connections while maintaining brevity (00:23:37) - Emphasizing stakes to underscore a topic's relevance (00:24:39) - Maintaining simplicity by avoiding empire-building, utilizing contractors, and focusing on core offerings (00:27:28) - Starting small and curating members while maintaining quality controls for community growth (00:29:47) - Engaging active supporters and notable individuals for a self-sustaining community (00:33:16) - Utilizing the 'Jobs to be Done' framework to better serve readers (00:38:37) - Why some topics resonate more than others (00:41:17) - How Lenny's Newsletter drives engagement and distribution across platforms (00:44:26) - Appreciating Substack's simplicity and audience growth (00:48:00) - Debrief Learn more about your ad choices. Visit megaphone.fm/adchoices

Today on the show, we dive into 4 validation strategies Lenny Rachitsky suggested in a recent newsletter. Nate & Josh lean into what's worked for them and which methods they think are the most effective. Lenny's article: https://www.lennysnewsletter.com/p/how-to-validate-your-b2b-startup This is episode 90

I'm thrilled to bring you a vibrant conversation with Alex Farmer, the founder of the Customer Success Excellence Awards and Chief Customer Officer at Nezasa. He brings a wealth of knowledge from the frontlines of various customer-facing role experience, particularly in the startup realm. Through our rich discussion, we explore how to personalize your customer success processes, streamline tech stack elements into a unified, customer-centric overlay, and much more.Join us as we take a deep dive into the art of enhancing customer experience and accessibility. With Alex's expertise, we unpack strategies to establish a single access point across multiple systems for your customers. We also shed light on empathizing with customers to better grasp their needs and confusion. We also explore the Customer Success Excellence Awards program founded by Alex, with a mission to honor those in the industry that are putting in the hard work to make customers successful.Enjoy! I know I sure did...Alex's LinkedIn: https://www.linkedin.com/in/alexanderfarmer/Customer Success Excellence Awards: http://customersuccessexcellence.com/Resources Mentioned In This Episode:Blogs:SaaStr Blog: https://www.saastr.com/blog/Kellblog: https://kellblog.com/Lenny Rachitsky: https://www.lennyrachitsky.com/Shoutouts:Angelika Marek @ Bazaarvoice: https://www.linkedin.com/in/angelika-m/Dickey Singh @ Cast.app: https://www.linkedin.com/in/dickey/Annie Dean @ Recast Success: https://www.linkedin.com/in/anniedean/Marcus Innocenti @ Zoom: https://www.linkedin.com/in/minnocenti/Jeff Beaumont @ GitLab (featured in previous episode): https://www.linkedin.com/in/jeffbeaumont/Dan Ennis @ Monday.com (featured in previous episode): https://www.linkedin.com/in/dan-ennis-cs/Chad Horenfeldt (featured in previous episode): https://www.linkedin.com/in/chadhorenfeldt/Support the show+++++++++++++++++Listener Submissions:If you'd like to call in with commentary or a question to be addressed in a future episode, call our submission line at +1 (512) 222-7381. Leave us a 2-3 minute message with your comment or question using either your real name or a pseudonym, and we'll feature your clip on the show!Like/Subscribe/Review:If you are getting value from the show, please follow/subscribe so that you don't miss an episode and consider leaving us a review. Website:For more information about the show or to get in touch, visit DigitalCustomerSuccess.com. Buy Alex a Cup of Coffee:This show runs exclusively on caffeine - and lots of it. If you like what we're, consider supporting our habit by buying us a cup of coffee: https://bmc.link/dcspThank you for all of your support!The Digital Customer Success Podcast is hosted by Alex Turkovic

Episode 472: Sam Parr (@TheSamParr) and Shaan Puri (@ShaanVP) unveil their list of the best companies making more than $1M annually with no full time employees. Want to see more MFM? Subscribe to the MFM YouTube channel here. ----- Check Out Sam's Stuff: * Hampton * Ideation Bootcamp * Copy That Check Out Shaan's Stuff: * Try Shepherd * Shaan's Personal Assistant System * Power Writing Course * Daily Newsletter ----- Show Notes: (00:00) - Introduction (03:50) - Biggest One-Person Business - Stardew Valley, Streamyard, and Plenty of Fish (15:45) - Highest Degree of Difficulty - TinyWow and Photopea (26:00) - Easiest to Recreate: GetCyberLeads, Lenny Rachitsky, and Marketing Examples (36:00) - Most Fun: Joe Rogan and Gym Streak (42:00) - Business You Would Most Want to Own: Milled and BuiltWith (46:30) - Rookie of the Year: Joseph Mambwe and Only Finder (55:30) - Worst of the Best: The Van Trump Report ------ Links: * Stardew Valley * Streamyard * Plenty of Fish * TinyWow * Photopea * GetCyberLeads * Lenny Rachitsky * Marketing Examples * Gym Streak * Milled * BuiltWith * Hampton Blog on Joseph Mambwe * OnlyFinder * Van Trump Report * Do you love MFM and want to see Sam and Shaan's smiling faces? Subscribe to our Youtube channel. ------ Past guests on My First Million include Rob Dyrdek, Hasan Minhaj, Balaji Srinivasan, Jake Paul, Dr. Andrew Huberman, Gary Vee, Lance Armstrong, Sophia Amoruso, Ariel Helwani, Ramit Sethi, Stanley Druckenmiller, Peter Diamandis, Dharmesh Shah, Brian Halligan, Marc Lore, Jason Calacanis, Andrew Wilkinson, Julian Shapiro, Kat Cole, Codie Sanchez, Nader Al-Naji, Steph Smith, Trung Phan, Nick Huber, Anthony Pompliano, Ben Askren, Ramon Van Meer, Brianne Kimmel, Andrew Gazdecki, Scott Belsky, Moiz Ali, Dan Held, Elaine Zelby, Michael Saylor, Ryan Begelman, Jack Butcher, Reed Duchscher, Tai Lopez, Harley Finkelstein, Alexa von Tobel, Noah Kagan, Nick Bare, Greg Isenberg, James Altucher, Randy Hetrick and more. ----- Additional episodes you might enjoy: • #224 Rob Dyrdek - How Tracking Every Second of His Life Took Rob Drydek from 0 to $405M in Exits • #209 Gary Vaynerchuk - Why NFTS Are the Future • #178 Balaji Srinivasan - Balaji on How to Fix the Media, Cloud Cities & Crypto * #169 - How One Man Started 5, Billion Dollar Companies, Dan Gilbert's Empire, & Talking With Warren Buffett • ​​​​#218 - Why You Should Take a Think Week Like Bill Gates • Dave Portnoy vs The World, Extreme Body Monitoring, The Future of Apparel Retail, "How Much is Anthony Pompliano Worth?", and More • How Mr Beast Got 100M Views in Less Than 4 Days, The $25M Chrome Extension, and More

EPISODE DESCRIPTION Chenell is the writer of Growth In Reverse, a weekly newsletter where she reverse engineers how a top creator grew from 0 to 50k+ subscribers. Chenell has done deep dives on Justin Welsh, Codie Sanchez, Lenny Rachitsky, Harry Dry, and many more. I read it every week and think it's incredibly well-done. The premise is super clear, and as a result, Chenell has seen her OWN newsletter grow very quickly – nearing 10,000 subscribers in just about four months. In this episode, you'll learn: The common patterns between these newsletter operators Some of the most effective growth tactics she's uncovered And what's working for HER right now Full transcript and show notes Follow Chenell on Twitter / LinkedIn Subscribe to Growth In Reverse *** CONNECT

Based in San Francisco, Lenny Rachitsky is a Product specialist with a strong focus on growth. He spent seven years at Airbnb, where he started as a Product Manager in 2012 and later became a Product lead for supply growth. Lenny now works as a writer, investor, and consultant for product growth. He creates content on Substack, YouTube, and other podcasting platforms.Subscribe to Lenny's newsletter: https://www.lennyrachitsky.com/

Episode 32 Founder's Journal: Alex Lieberman (@businessbarista) shares his experience and tips on how to acquire your first group of customers, whether that be 100 or 1000. First, he talks about the early stages of Morning Brew, going from classroom to classroom to sign people up for the newsletter. This approach is known as the hub & spoke model which he plans on using for The Plunge. Then, he'll talk about Lenny Rachitsky's essay that dives into 7 successful ways to obtain early customers.  Links: http://paulgraham.com/ds.html https://www.lennysnewsletter.com/p/how-the-biggest-consumer-apps-got https://viral-loops.com/blog/robinhood-referral-got-1-million-users/ #TheCrazyOnes #Startups #Entrepreneur Listen to The Crazy Ones here: https://link.chtbl.com/OV4W93_W Watch The Crazy Ones here: https://www.youtube.com/@TheCrazyOnesPod  Subscribe to Morning Brew! Sign up for free today:  https://bit.ly/morningbrewyt Follow The Brew! Instagram - https://www.instagram.com/morningbrew/ Twitter - https://twitter.com/MorningBrew Tik Tok - https://www.tiktok.com/@morningbrew Follow Our Hosts! Alex Lieberman (@businessbarista) Jesse Pujji (@jspujji)

Is a podcast easier than a newsletter? Lenny Rachitsky joins Kipp and Kieran as they dive deep into the content creation rabbit hole - tactics on how to grow and scale a newsletter, solving for a problem as your north star, how to validate your content, why being a ruthless editor is crucial, and more. About Lenny Rachitsky Lenny writes a popular newsletter at LennysNewsletter.com, hosts Lenny's Podcast, angel invests, and advises startups on product and growth. Previously, Lenny spent seven years at Airbnb leading initiatives in growth, quality, and community. Before Airbnb, Lenny was a founder (sold to Airbnb), and engineer. Connect with Lenny! Website https://lennysnewsletter.com  Twitter https://twitter.com/lennysan  Lenny's Favorite Newsletters Noah Smith's Noahpinion https://noahpinion.substack.com/  Emily Oster's ParentData https://www.parentdata.org/  Tyler Cohen's Marginal Revolution https://marginalrevolution.com/  We're on Social Media! Follow us for everyday marketing wisdom straight to your feed YouTube: ​​https://www.youtube.com/channel/UCGtXqPiNV8YC0GMUzY-EUFg  Twitter: https://twitter.com/matgpod  TikTok: https://www.tiktok.com/@matgpod  Thank you for tuning into Marketing Against The Grain! Don't forget to hit subscribe and follow us on Apple Podcasts (so you never miss an episode)! https://podcasts.apple.com/us/podcast/marketing-against-the-grain/id1616700934   If you love this show, please leave us a 5-Star Review https://link.chtbl.com/h9_sjBKH and share your favorite episodes with friends. We really appreciate your support. Host Links: Kipp Bodnar, https://twitter.com/kippbodnar   Kieran Flanagan, https://twitter.com/searchbrat  ‘Marketing Against The Grain' is a HubSpot Original Podcast // Brought to you by The HubSpot Podcast Network // Produced by Darren Clarke.

Lenny Rachitsky built a thriving newsletter about product development. Here's how he did it, step by step, and how he's now making more money from the newsletter than he did as a product lead at Airbnb.

Lenny Rachitsky built a thriving newsletter about product development. Here's how he did it, step by step, and how he's now making more money from the newsletter than he did as a product lead at Airbnb.

Lenny Rachitsky runs the #1 business newsletter on Substack, which is simply called lennysnewsletter.com.   Lenny has a REALLY interesting career path. He started off as an engineer, then decided to start his own business, which got acquired by Airbnb, where he stayed and worked for over 7 years until he quit to be his own boss again!   When Lenny left Airbnb to tinker with the different startup ideas, he was writing on the side to share his learnings. But then his writing started to gain a lot of traction online… and it became his MAIN hustle!   On an Indie Hackers post, he said the newsletter is making around $500k ARR, so I had to invite him over to hear about how he runs his one-person business.   P.S. Need help turning a business idea into reality? I reopened my course Monthly1K for just $10 (kinda limited time). Sign up at OkDork.com/Monthly1K.  

Today's guest is Jennifer Phan - co-founder of Passionfroot - a platform empowering creators to partner directly with brands and agencies to monetise their product and services, be it a podcast, a newsletter or YouTube channel.Born to immigrant parents, Jen started her career as VC investor before seeing a gap in the market for creators who are trying to earn money directly from their work. Passionfroot takes care of the admin and business side of earning a living from your work and helps to remove the barriers and gate keepers which have historically been in place and held many creators back.In this conversation, Jen and I discuss the wave of creators turned entrepreneurs, why she wants to empower creators anywhere in the world, what the next frontier for creator entrepreneurs looks like, as well as some of the platforms she recommends to help you grow your community.This is a great conversation with lots of fantastic lessons for founders and creators so I hope you get as much value out of it as I did.Please let us know what you think of this episode and please rate, review and share - it means the world to me and helps others to find it too.Jennifer on Twitter / Passionfroot website / Passionfroot Podcast, Creators on Air here / Newsletter hereDanielle on Twitter @daniellenewnham and  Instagram @daniellenewnham  / Newsletter here 

Annie Pearl is the CPO @ Calendly, the company that makes scheduling meetings simple and painless. Before Calendly, Annie led Glassdoor's product vision and user experience, managing a 70-person product and design org.  Shreyas Doshi is an investor, advisor, and all-around product OG. Most recently Shreyas spent over 5 years at Stripe where he was Stripe's first PM Manager and helped grow the PM function (from ~5 to more than 50 people). Before Stripe, Shreyas was a Director of Product Management @ Twitter. David Lieb is one of the product OGs of the last decade. As the founder of Bump David pioneered how over 150M users shared data, contacts and more before the company was acquired by Google. At Google, David took this one step further by creating Google Photos. Marty Cagan is one of the OGs of Product and Product Management as the Founder of Silicon Valley Product Group. Before founding SVPG, Marty served as an executive responsible for defining and building products for Hewlett-Packard, Netscape Communications, and eBay. Aparna Chennapragada is the former CPO @ Robinhood, revolutionizing consumer finance with commission-free investing. Prior to Robinhood, she spent an incredible 12 years at Google, most recently as VP and GM for Consumer Shopping and also as the lead AR and Visual Search products.  Lenny Rachitsky is one of the OGs of product, having spent over 7 years at Airbnb as a product lead he left to start his newsletter, find it here. This has scaled to thousands upon thousands of readers and one of the most popular newsletters on Substack.  For the last 7 years, Kayvon Beykpour has been at Twitter where he led all of the teams across Product, Engineering, Design, Research, and Customer Service & Operations. Kayvon came to Twitter through Periscope, the live broadcasting app he founded that was acquired by Twitter in 2015. Scott Belsky is an entrepreneur, author, investor, and currently serves as Adobe's Chief Product Officer. Scott oversees all of product and engineering for Creative Cloud, as well as design for Adobe. In 2006, Scott founded Behance, and served as CEO until Adobe acquired Behance in 2012. In Today's Episode on How to Hire a Product Manager, We Discuss: 1.) When to Hire Your First PM: What are the core signs that the founder must delegate and hire their first PM? What are the first things that are breaking when you do not have one but need one? How does the timing of the first PM differ when comparing B2B vs B2C? 2.) What is the Right Profile: What should founders look for in this first PM hire? What traits make the best? What are the biggest red flags in the personalities and styles of potential candidates? Should they have experience in the product domain they are entering? What are the single biggest mistakes founders make when analyzing the resumes of potential PM candidates? What should they look for in their resume? 3.) The Hiring Process: How To Hire a Product Manager How do we structure and run the hiring process for this person? What tests can we do to understand if they have the skill set we need for the role? How do we structure a hiring panel to make this process more effective? What are the biggest mistakes founders make in the hiring process for PMs?

The great disruptors of Silicon Valley are nearly all product led. In this episode, Chris and Yaniv dive deep on how a product-led organisation works, what is necessary for it to be successful, the various responsibilities of Product Managers and their counterparts, and most importantly: what it takes to transform any organisation into one that is truly product-led. It's not easy, but it is worth it! This episode helps guide the way. This is Part 2 of a 2-part series on transforming into a product-led organisation, designed to work as a companion to Chris's recent presentation on the same topic. We strongly recommend listening to Part 1 first. You can access the rest of Chris's “Scaling Startups” series at https://www.chrissaad.com/startupscale Article on the W Framework by Lenny Rachitsky and Nels Gilbreth: https://review.firstround.com/the-secret-to-a-great-planning-process-lessons-from-airbnb-and-eventbrite Turn the Ship Around! By L. David Marquet: https://www.amazon.com/Turn-Ship-Around-Building-Breaking/dp/1591846404 Our interview with Marty Cagan: https://spotifyanchor-web.app.link/e/v6ZD6YOHTwb Our episode on Alignment: https://spotifyanchor-web.app.link/e/oMrMJU2HTwb Follow the Startup Podcast on LinkedIn https://www.linkedin.com/company/the-startup-pod/ Follow us on Twitter Yaniv Bernstein @ybernstein Chris Saad @chrissaad Please rate and Review The Startup Podcast on your podcast app. Ask questions for future Listener Q&A episodes: https://forms.gle/NZzgNWVLiFmwvFA2A Listen on Apple: https://podcasts.apple.com/au/podcast/the-startup-podcast/id1612757016. Listen on Spotify: https://open.spotify.com/show/5C6oN1uFj29A4jHZn57lNO. Listen on Google: https://podcasts.google.com/feed/aHR0cHM6Ly9hbmNob3IuZm0vcy84NjhlNWEwNC9wb2RjYXN0L3Jzcw A bit about our hosts: Chris Saad: Independent Startup Advisor and Angel Investor, who helps startups and entrepreneurs fast-forward company's growth. Chris consults on developer platforms & ecosystems, future of media, data portability, on-demand economy, and the Silicon Valley ecosystem. Visit http://chrissaad.com/advisory/ or connect with Chris on LinkedIn https://www.linkedin.com/in/chrissaad/ Yaniv Bernstein: Founder and COO of Circular, a subscription e-commerce platform with sustainability at its heart. By focusing on customer experience while reducing waste and underutilization, Circular provides subscriptions to premium devices at affordable prices and with unmatched flexibility. Visit Circular https://www.nowcircular.com/ and connect with Yaniv on LinkedIn https://www.linkedin.com/in/ybernstein/

#90: Top podcast host, Lenny Rachitsky joins Chris to discuss work-related techniques for success. They talk about finding a job that aligns with your interests, ways to stand out and get noticed, nailing your interview, effectively negotiating your compensation, managing up, and strategies to getting promoted.Lenny Rachitsky (@lennysan), an engineer turned startup founder and former product manager at Airbnb is the creator of Lenny's Newsletter and the wildly popular podcast, Lenny's Podcast. Lenny is well-known as one of the top minds in the world when it comes to building product, driving growth, and helping people accelerate their careers.Full show notes at: https://allthehacks.com/work-lenny-rachitsky Partner Deals Daffy: Free $25 to give to the charity of your choicePacaso: Free early access to listings and $2,500+ in closing creditsRocket Money: Easily cancel your unused subscriptionsAthletic Greens: Free 1 year supply of Vitamin D and 5 free travel packs Selected Links From The EpisodeConnect with Lenny Rachitsky: Twitter | Website | Podcast | Newsletter | TikTokLenny's Job BoardLenny's NewsletterThe 10 Commandments of Salary NegotiationHow to Get PromotedProduct Management Career LaddersSaying NoMedium: What Seven Years at Airbnb Taught Me About Building a BusinessLenny's Talent CollectiveAirbnb Alumni Investing Syndicate: AirAngelsFocus App: CenteredLoom“State of Me” Email Template“Sprint” TemplatePodcasts:All the Hacks#37: The Surprising Habits of Backable People with Suneel Gupta#72: Increasing Productivity, Procrastinating Less and Living a Happier, Healthier Life with Ali Abdaal#63: Deep Work, Digital Minimalism and Becoming So Good They Can't Ignore You with Cal Newport#7: Managing Your Time to Get More Done with Laura VanderkamBooks:Backable: The Surprising Truth Behind What Makes People Take a Chance on YouMake Time: How to Focus on What Matters Every DayGetting Things Done: The Art of Stress-Free ProductivityLenny and Chris' California RecommendationsCavallo Point LodgeAndy Goldsworthy's Wood Line Fairfax Mount Tam Mountain BikingFishMill Valley LumberyardFlour Craft Bakery Full Show NotesIntroduction to Lenny Rachitsky  (00:00)Content that's applicable outside of product management (01:37)Lenny's Job Board (04:18)Reverse job search feature: “spotlight” (07:07)Four points to focus on when identifying your interests (07:42)Finding value in a variety of experiences  (15:53)How to stand out and get noticed (17:43)Advice on how to nail an interview (24:42)Negotiating your salary and compensation (27:28)What to optimize for when working for a company (33:28)Finding the way to make an impact (34:43)  How to get promoted effectively (35:48)Finding the right balance and value of saying “no” (42:10)Being effective with your output so you can make the most significant impact (48:24)Deciding when it's time to move on (52:11)Tips for structuring your free time (55:14)Experimenting with creation (56:53)Chris' next steps (1:00:19)Managing up: keeping your manager aware of what you're doing (1:00:52)Lenny and Chris' California recommendations (1:02:56)Where to find Lenny Rachitsky online (1:05:21) PartnersDaffyDaffy is a not-for-profit community built around a new modern way to give, and they are on a mission to help people be more generous, more often. We do all our giving through Daffy because they make it so easy to put money aside for any of the 1.5+ million nonprofits in the us. You can make a one-time contribution or you can set a little aside each week or month and all your contributions are tax deductible.To start giving today and get your free $25 to give to the charity of your choice, go to allthehacks.com/daffy PacasoPacaso is the modern way to buy and own a second home in over 40 world-class destinations. Each home is set up in an LLC, so you can buy as little as 1/8 of the property. And then Pacaso handles everything, from expert interior design to ongoing management, dedicated local support, and equitable, app-based scheduling – making ownership simple and turnkey.To get a free Pacaso Access account, which includes early access to new listings and up to $10,000 in credit towards closing costs, go to allthehacks.com/pacaso Rocket MoneyRocket Money is the new app that helps you identify and stop paying for subscriptions you don't need, want, or simply forgot about. You can see all your unwanted subscriptions in one place, keep the ones you want and cancel the ones you don't – right from the app. Your Rocket Money concierge is there to cancel your subscriptions, so you don't have to. No talking to humans. No difficult conversations.Join over 2 million users who've used Rocket Money to save over $100 million and start canceling your unused subscriptions today, by going to allthehacks.com/rocketmoney Athletic Greens Athletic Greens is a foundational nutrition drink designed to remove the friction from covering the daily nutritional needs of a modern diet. It combines more than 9 essential nutrition products into one convenient and great-tasting drink, giving you an easy and efficient way to get your daily multivitamin, multimineral, probiotic, prebiotic, functional greens blend, immune support complex and more. It contains no GMOs, no harmful ingredients and no artificial colors or sweeteners.Right now, Athletic Greens is going to give you a free 1 year supply of immune-supporting Vitamin D and 5  free travel packs with your first purchase at allthehacks.com/athleticgreens Connect with All the HacksAll the Hacks: Newsletter | Website | Facebook | EmailChris Hutchins: Twitter | Instagram | Website | LinkedIn

In this 35-minute convo, Lenny Rachitsky, creator and author of Lenny's Newsletter and the "Friends of Lenny's Newsletter" community, discusses the inspiration behind Lenny's Newsletter, how the community got started, the added value community can bring to its members as whole, and what responsibility hosts and companies have to their communities.Community and DevRel leaders perform incredible feats to grow, engage, and support their communities, empower their businesses, and build products and experiences people love. Each day, they bring their companies and communities closer together. These are the stories of their work. The Uncommon community is powered by Common Room, the intelligent community growth platform that enables you to unlock community insights so you can grow happier customers, measure outcomes, and drive business impact. Learn more about how you can help your community thrive with Common Room at commonroom.io, and join the Uncommon community at commonroom.io/uncommon.

Scott Belsky is an entrepreneur, master of product reviews, author, investor, and currently serves as Adobe's Chief Product Officer and Executive Vice President, Creative Cloud. Tony Fadell, often referred to as the father of the iPod is one of the leading product thinkers of the last 30 years as one of the makers of some of the most game-changing products in society from the iPhone and iPod to more recently founding Nest. Lenny Rachitsky is one of the OGs of product, having spent over 7 years at Airbnb as a product lead he left to start his newsletter, find it here. Kayvon Beykpour is one of the most prominent product leaders of the last decade. For the last 7 years, Kayvon has been at Twitter where he led all of the teams across Product, Engineering, Design, Research and Customer Service & Operations. Aparna Chennapragada is Chief Product Officer @ Robinhood, the company revolutionising consumer finance with commission-free investing. In Today's Episode Breaking Down Product Reviews We Discuss: 1.) What makes a truly great product review? 2.) What are the biggest mistakes that product leaders make when leading product reviews? 3.) Who should be invited to the product review? How does this change with scale? How does this change in a world of remote work and Zoom? 4.) Who should set the agenda for the product review? 5.) How can leaders assign accountability and ensure that the follow-ups from product reviews are executed on? 6.) How can leaders ensure that they do not dominate product reviews with the weight of their words? How can they give designers and devs the space to share their thoughts without being judged?

Today on the Product Thinking Podcast, Melissa Perri is joined by Lenny Rachitsky, author of the popular product advice column Lenny's Newsletter. Melissa and Lenny compare notes on what it's like to move from working directly in product to creating product content and courses, and Lenny explains how his newsletter was born and its growth trajectory since, what he's learned about how to create valuable content, what success means to him, and how to keep your energy focused on the things that light you up. Here are some of the key points you'll hear Lenny and Melissa talk about: How Lenny got into product management originally. He started his career in computer science and initially worked in coding before deciding to try and build his own company, which he did in Montreal, before joining AirBNB where he moved into product management. [02:20] Melissa talks about how, not that long ago, there wasn't really a career path for product management and her realization that you can be involved in management without building it yourself. [05:15] By writing Medium post called What Seven Years at AirBNB Taught me about building that did incredibly well, Lenny realize there was an audience out there hungry for content about product management and development. Eventually, this led to his newsletter, job board, and course. [09:55] Lenny shares how much of his work is research-based – determining the information he wants to share, and reaching out to the experts who have the best answers, then consolidating them into actionable, valuable materials for people. [14:55] Where do we get energy from things we do? Not every type of work or every type of content is a home run for the person creating it. Melissa and Lenny talk about how a Product mindset can be helpful with this. [18:25] Melissa talks about how even when you're running your own company, it's still work, and you can still burn out. There is nothing wrong with building a lifestyle business–not everything has to be a major, venture-funded enterprise. [21:15] Many people want to start lifestyle-type businesses. Lenny shares his advice for building something that brings you a lot of joy. One of the keys is having people to support you, and building in time for experimentation. [25:20] Melissa shares her own philosophy on building a business that fits your lifestyle instead of changing your life to fit your business, and how to tell when it's not working. [29:45] There are two phases to growth–how it starts and how it grows. Lenny talks about how growth has worked in his ventures. Quality of content is paramount.[34:40] Lenny talks about what is currently interesting and inspiring to him in Product management. [40:55]   Resources:  Lenny on the web | Twitter | LinkedIn Lenny's Newsletter 28 Ways to Grow Supply in a Marketplace

Today on the Product Thinking Podcast, Melissa Perri is joined by Lenny Rachitsky, author of the popular product advice column Lenny's Newsletter. Melissa and Lenny compare notes on what it's like to move from working directly in product to creating product content and courses, and Lenny explains how his newsletter was born and its growth trajectory since, what he's learned about how to create valuable content, what success means to him, and how to keep your energy focused on the things that light you up. Here are some of the key points you'll hear Lenny and Melissa talk about: How Lenny got into product management originally. He started his career in computer science and initially worked in coding before deciding to try and build his own company, which he did in Montreal, before joining AirBNB where he moved into product management. [02:20] Melissa talks about how, not that long ago, there wasn't really a career path for product management and her realization that you can be involved in management without building it yourself. [05:15] By writing Medium post called What Seven Years at AirBNB Taught me about building that did incredibly well, Lenny realize there was an audience out there hungry for content about product management and development. Eventually, this led to his newsletter, job board, and course. [09:55] Lenny shares how much of his work is research-based – determining the information he wants to share, and reaching out to the experts who have the best answers, then consolidating them into actionable, valuable materials for people. [14:55] Where do we get energy from things we do? Not every type of work or every type of content is a home run for the person creating it. Melissa and Lenny talk about how a Product mindset can be helpful with this. [18:25] Melissa talks about how even when you're running your own company, it's still work, and you can still burn out. There is nothing wrong with building a lifestyle business–not everything has to be a major, venture-funded enterprise. [21:15] Many people want to start lifestyle-type businesses. Lenny shares his advice for building something that brings you a lot of joy. One of the keys is having people to support you, and building in time for experimentation. [25:20] Melissa shares her own philosophy on building a business that fits your lifestyle instead of changing your life to fit your business, and how to tell when it's not working. [29:45] There are two phases to growth–how it starts and how it grows. Lenny talks about how growth has worked in his ventures. Quality of content is paramount.[34:40] Lenny talks about what is currently interesting and inspiring to him in Product management. [40:55]   Resources:  Lenny on the web | Twitter | LinkedIn Lenny's Newsletter 28 Ways to Grow Supply in a Marketplace

Welcome to the very first episode of Lenny’s Podcast!Every week, Lenny Rachitsky will interview world-class product leaders and growth experts to uncover concrete, actionable, and tactical advice to help you build, launch, and grow your own product. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Lenny Rachitsky is one of the OGs of product, having spent over 7 years at Airbnb as a product lead he left to start his newsletter, find it here. This has scaled to thousands upon thousands of readers and is one of the most popular newsletters on Substack. Lenny is also an extremely active angel investor with a portfolio including Figma, Sorare, Clubhouse, Vanta, WhatNot and many more incredible companies. If that was not enough, Lenny also has the best course on product management, check it out here. In Today's Episode with Lenny Rachitsky You Will Learn: 1.) Origins in Product: How did Lenny make his way iunto the world of product management at Airbnb? What were some of his biggest takeaways from his time at Airbnb on product? What mistakes did he make on product at Airbnb? How did it impact his product thinking? 2.) Product Management: 101 How does Lenny define product management today? How is the role of PM changing? When is the right time to hire your first PM as a startup? What is the difference between Head of Product and CPO? When do you hire each? What are the biggest mistakes founders make when hiring their first product hires? 3.) The Hiring Process: How should founders breakdown the process of hiring for their first in product? What does the interview process look like? How should founders structure it? What core questions should teams ask of prospective candidates? What are red flags when interviewing potential product hires? 4.) The Onboarding Process: How should founders structure the onboarding process for new product hires? What can founders do to make PMs successful in their first 30 days? Where do many product hires make the biggest mistakes in the first 30 days? What can product hires do to build trust with their new team? Items Mentioned in Today's Episode with Lenny Rachitsky Lenny's Fave Book: The Mom Test

Levels CEO, Sam Corcos, sat down with Lenny Rachitsky, an early team member of Airbnb and one of our Levels investors. Sam and Lenny deconstructed the idea of a PM, Product Manager, as well as what it means and what are some of the implications of having PMs across a company. Become a Levels Member – levelshealth.com Learn about Metabolic Health – levelshealth.com/blog Follow Levels on Social – @Levels on Instagram and Twitter

Listen to the Creator Lab: https://www.listennotes.com/podcasts/creator-lab/lenny-rachitsky-lennys-bUBLKO_NIG4/Growth Loops are the New Funnels: https://www.reforge.com/blog/growth-loopsThe Racecar Growth Gramework: https://www.reforge.com/blog/racecar-growth-frameworkTranscripttoday for the sake of focus we're going to start with this growth framework called the race car growth framework which i thought was really incredible um so let's just kick it off man from what i could see from the outside from reading your work there's four components to this product growth which is - the first one was the growth engine- the second one is called turbo boosts- third is lubricants - the fourth is fuel we're going to explain what all of those are in a second um but before we even go into the details could you just share like a bit of context around what who who is this for and who is it not for yeah because absolutely this isn't for every single company in the world and um you know you've probably applied this in many different contexts but yeah curious what what stands out to you there so maybe zooming out even further i spent a lot of my time with this newsletter looking into growth stories and how growth strategies and essentially understanding how all the most successful companies grew and i've spent a lot of time on the early days of how they got their first say a thousand users and then i've also spent a lot of time on the longer term down the road strategy of how do they grow long-term what can what needs to work for a company to continue growing and so now there's kind of these two ends of the spectrum that are coming into focus for me of how do i get your early users and then how to long term grow your business so this race car framework is focused on the long term how do you grow eventually and long term and then we can even talk about how to get your first users and then i'm slowly filling in these puzzle pieces through more and more of my research of how companies go from zero to say a million and it turns out it's it's not as mysterious as people think there's not actually that many options it's more of a question of which of the options do you choose and then how do you become the best at that or do something remarkable within that option so so we could start at the end and then we can come back to the beginning days so the end is this race car framework and i this is uh based on work that i did with a buddy of mine dan haukenmeyer so this post is something we both put together and what we found is there's a really cool mental model of thinking about how businesses grow long-term and it turns out you can think of your company like a race car which includes these four components that you're talking about there's the engine there's uh turbo boosts lubricants and then fuel and the engine is the most important part because that's what drives your business and it turns out there's essentially four engines you can choose from as a company and uh and these engines are self-sustaining loops that keep your business growing and there's kind of like a fuel that goes into it and then the output is growth so should we dive into those yeah yeah so i love that so i'll repeat kind of what i heard and understood and then you can clarify if i heard it wrong so the growth the growth engine is the most important part is self-sustaining the turbo boosts from what i understand are more like these one-off events or big hero moments maybe events a super bowl ad and they can maybe make a big splash but they're not self-sustainable the way a growth engine is and we'll go into the details of what that means and then the lubricants are more about running efficiently exactly things that make everything run better exactly and then the fuel is what's actually needed to make the car run so the input that's needed that's that's awesome so maybe yeah we can start off by going into the growth engine itself so i've heard you talk about loops and engines and i have a visual of this thing going around and people talk about flywheels i found like a lot of the jargon sometimes is like overly used but in this case i think it actually is really helpful to see it visually um because i think if you think of like a growth engine in a traditional business you think of a marketing funnel which is not exactly the same thing but a lot of the time when you're getting new users and getting them to convert and become paying users and then spread and share something like in business school you might learn it like a funnel and i think what i like about this is it's not necessarily like a linear thing that just goes from top to bottom it's more something that keeps feeding itself is that accurate before we move on from there yeah that's exactly accurate and there's this uh group called reforge who was one of the first uh i guess um groups that kind of figured out that this is the thing that matters more than funnels so they kind of have this famous blog post that loops for the new funnels and in reality they're both important like funnels are a part of these loops and so they both uh are worth thinking about but when you're starting out it's a lot more important to think about the flywheel slash engine slash loop they're all kind of the same idea and it's just your point there are these things that kind of feed themselves and keep going yeah and so what we're going to do is we're going to be talking about a lot of theory but what we're going to try to do is layer on examples wherever possible so if we're talking about a funnel or a sorry not a funnel a a uh flywheel is there one that we could just explain to people yeah like airbnb's flywheel or a company that people know about## ENGINESlet me share the four engines first and then we can talk about yeah that sounds great leverage each one so essentially the way to think about this is if you think about like all the things you can do to grow your business there's like pr there's events there's paid ads there's seo there's this like whole collection of options and what this concept tries to help you with is which ones should you focus on deeply and which are just kind of these one-off things or just micro-optimizations so the engines are the there's only four ways your business is really going to grow long term and the four ways are - performance marketing and the way that loop works is you spend money to run an ad the ad drives customers the customers generate revenue and you can feed that into more ads so that's a pretty straightforward one - the next is virality which is what we all know and love when we think about viral growth essentially users draw new users and those users join and invite their friends and their friends join and it goes on and on and they'll give examples but maybe an example that one is like yeah snapchat or telegram whatsapp facebook things where you're kind of encouraged in by your friends and we can talk about like how to know which of these your business is most naturally suited for because it's not like choose any it's usually based on the type of product that you have one is going to fit best and there's actually this kind of growing meme of first time founders focus on product and second time founders focus on distribution and a lot of that is that's actually very true i find and knowing these engines is how you think about that is almost working backwards from i have a unique way of being really good at one of these things what product can i build to take advantage of that that's that's in it that's a mental model that i find useful so anyway let me go through the four and then we can talk in more depth - content is the third one and that includes seo as one and usually the the most popular one but also includes like viral videos and content people share with each other so an example of a company that grew primarily through content is like glassdoor or uh trulia or quora and reddit where you just think of like looking for a thing and then shows up in your google results and then you go find it yeah - and then the fourth is just sales where you hire a salesperson they generate they find customers customers generator revenue hire more sales people that's usually the most common engine for enterprise businesses b2b businesses like a force i think it's probably a good example of yeah salesforce is a classic example the king that's right yes all right that's awesome and i i know that you've mentioned those are the four the four main ones in the blog post you also mentioned that there's some others people think about but like partnerships physical space um so like physical space could be retail stores uh like a showrooming thing that casper done for example came to mind for me um shelf placement casper is a good example where they they're almost exclusively performance marketing driven and then they started expanding into other engines like retail where like the loop of a physical location in physical placement is you pay money for a location either on a shelf or a on a block people walk by you know for those people buy stuff generate revenue and keep the business going sometimes it's just like a brand building thing where it's not meant to make money but that's i think directly yeah yeah and then the other one was partnerships which we'll just touch on briefly because even though it's not part of those those four components i think increasingly we're seeing really interesting examples of this even in the creator world um that both of us semi-playing well you're definitely playing and i'm partially playing in now you're definitely playing it yeah yeah i'm definitely kind of in there nowadays um but yeah so i think it's an interesting one as well because a lot of people don't always think of this and maybe it's not the primary way to start but for some people it can be a huge growth driver i mean even at google when i was there and that's a really obviously huge established business channel sales was uh channel partners were a huge uh driver for us um even on a smaller scale affiliates for other companies i've worked with as well and even on a smaller scale if you're an independent creator i would think about partnerships too because um you know the way i'd see it like i did something with the hustle newsletter that wasn't like i didn't pay for anything but we both like i brought something to the table and they wanted to feature it so there was a way for me to be featured in their their newsletter where there's distribution so um i think it's probably worth mentioning those two as well but for the sake of this conversation we'll we'll start with those four ## WRINKLESan important wrinkle to think about when we talk about this stuff uh the kind of the core idea of an engine is that it continues to grow your business and sometimes partnerships do that where they continue to draw traffic sometimes it's kind of like a one-off event and it doesn't mean you shouldn't do that like other those other parts of the car are great it's just they're not going to continue driving growth and that's the core is you need to find a way that continues that growth otherwise you're just going to flatten out it again um another really important point of this concept is it's not that you just pick one and you'll win it's to actually do well you have to become one of the best in the world at that engine in order to have a chance and the way i think about it is you kind of find the cross-section of your market and one of these engines where you could be in a huge company if you're the best at say content for travel and another business can be amazing at performance marketing for travel so as an example airbnb is incredibly successful as a virality driven travel company but booking.com very large successful business is also really big but they become really good at performance marketing and and then there's like tripadvisor which became really big through content so the way to think about this is you just need to find a way to become the best at your market in one of these engines to have a really good chance and the main thing the main issue companies have is they don't realize how they have to become incredibly good at one of these things they think they can just do all these things in some small way and have a chance and it turns out that's really really hard 

Remote work has increased overall interest and reliance on digital tools that enhance collaborative and individual productivity however, not all of them are created equally. In this episode, founder and CEO of new mindfulness and productivity app Centered, Ulf Schwekendiek speaks with engineer, founder and author of popular business advice newsletter, Lenny Rachitsky to discuss his new holistic approach to productivity, the reason why his app proudly stands at the intersection of productivity and mindfulness, the ever-evasive idea of flow state and the widely untapped power behind the combination of mindfulness, productivity and tech.

Alex Lieberman is the co-founder and chairman of Morning Brew. Morning Brew is a media company bringing informative and digestible business news to your inbox every morning. They educate nearly 3,000,000 daily readers on the latest news from Wall Street to Silicon Valley.Alex also hosts The Founder's Journal Podcast where he gives listeners a “backstage pass” into building Morning Brew, and in turn, helps them build a better business or career.Morning Brew is considered to be the largest email newsletter on the web. Business Insider recently acquired a major stake in Morning Brew at a rumored valuation of over 75 million dollars. In this episode, you'll learn: The foundations for building a great media brand What methods and metrics work best for rapid subscriber growth How to optimize a referral program to gain explosive growth How to be the leader your employees need as you scale Links & Resources Business Insider Kara Goldin's LinkedIn page Hint Water Pat Flynn Pat Flynn: Why I Switched from AWeber to Infusionsoft to ConvertKit KickoffLabs Viral Loops Robinhood Tim Ferriss Harry's Razors Lenny Rachitsky Packy McCormick Guest's Links Alex's LinkedIn page Morning Brew Founder's Journal podcast Morning Brew Accelerator (MB/A) Alex's Twitter: @businessbarista Episode TranscriptAlex: [00:00:00]That's the beautiful thing about just business in general, this diversity of what brings people joy. People who love building process and planning who have a foundation and building on top of that foundation. You have people who have zero foundation. They want to prove to the world and prove to themselves that the crazy thing that's been in their head that they think is valuable, there's no proof of yet, that the actually people will love it.Nathan: [00:00:30]In today's episode, I talked to Alex Lieberman, who is the co-founder, and now chairman—formerly CEO—and now chairman of Morning Brew. They grew the newsletter to over 3 million subscribers, which is insane. Making it the largest email newsletter on the web. So if we're talking about newsletters on this podcast who better to talk to than Alex.We get into why he transitioned from CEO to chairman. We talk about the exit: they sold a majority of the company to Business Insider rumored at over a $75 million valuation, which is really, really impressive. One of the things we talk about the channels that drove growth, their affiliate program, the referral program that so many people talk about and reference, what works, what doesn't.We get his take on sponsorships versus paid content, details on the type of ads that they used in their paid acquisition when they were growing Morning Brew, so much.Anyway, there's a lot of good stuff. I'll get out of the way. Let's dive in.Alex, thanks for joining me.Alex: [00:01:32]Thanks so much for having me, pumped to do this.Nathan: [00:01:34]All right. So I want to start with, your role has shifted. You just moved from CEO of Morning Brew to chairman. And tell me a little bit about that.What, what instigated it. What made it time for that move? I know a lot of people who have run companies for years consider a move like that.Alex: [00:01:52]There's many months in the making. and I think in a lot of ways, the last year has kind of been like a unspoken transition, based on just the things that I was spending my time on and the things my co-founder Austin was spending his time on. You know, I think the, the way that I think about it is I loved—I've loved every part of Morning Brew, but like the things that have really given me energy is when I am building things from scratch, I love building things from scratch.And that's what I was able to do in, in the early days of the Brew, you know, our original newsletter, our B2B newsletters, our podcasts, like really creating the foundation for something that could obviously become a large media brand. As we've scaled, obviously like, you know, you've, I'm sure experienced this in your role, the roles of a CEO change 50 different times.And so the way, you know, the way I think about it is the first role that I had at Morning Brew was every role Austin. And I had every role. I always tended to lean more towards sales, marketing, and content, like more the creative and people facing side of the business. Austin always, spend more time on growth product, and like the finance, the finances of the business.And so I wore many different hats and I loved doing those things. And then as we started to grow, as we got the flywheel going of creating great newsletter content, attracting audience and monetizing our audience through advertising. My role shifted. And I went from a hundred percent doing to what I would say is like 50% doing, and 50% managing.And I really enjoyed managing, like I loved, I loved coaching people, supporting people, but what I also learned pretty early on in Morning Brew is that managing there, there were aspects of managing that I loved, and there are many aspects of managing that I didn't love. The way I think about managing is I think there's two aspects to managing there's call it like leadership and there's operational management, operational management, really being about.Like goal setting, metric checking, and making sure that you're holding someone accountable to continuing to do the job they're supposed to do really important job for a manager. Then on the flip side, I would say the leadership side of managing is kind of the empathetic management part, which is how do you support someone in their career growth?How do you talk to someone about the things that are impacting them in their job performance, whether it's things within their career or things in their personal life that are coming into their career, because that inevitably obviously happens as well. And what I realized is I really loved the second thing.I didn't necessarily really loved the first thing. The reason I bring that up is because as we've scaled as Morning Brew, let's say got to 50 people and. And at 50 people, we really, that was the point in time when we had to go from being reactive to proactive, where we no longer had one product we had at that point in time, we had two or three products.We were truly talking about this transition from newsletter company to media brand. And that was the point in time where it became very clear that proactive scaling process, senior leadership, what was, what was needed to build a brand, to transition from newsletter company to brand. And the reason I bring up what I was saying before about like operational management is because.In many ways. That is what Austin, my co-founder has always loved. And it, and as COO of the business, that is what he, oh, he did always did. And I think as we made that transition to needing more process going from let's call it a one to two layer business to a two or three layer business. as we needed to set one-year three-year five-year plans, as we needed to hire senior leaders, I think it, it was that operational management muscle that became far more of the time necessary to run the business.And so over the last year, what I found myself gravitating towards is this stuff that I always gravitated towards, which is like, Building new stuff. it was more of like the culture and leadership side of management and it was being like a creator myself. Right. And, and so for example, like building new stuff, what does that look like?Well, most recently Morning Brew launched our paid product. It's a, it's called MBA. It's an accelerator for business professionals. Like that is something that I spent a lot of my time on. And so all of that to say, like, this was a transition that was really difficult for me from, I think, an ego perspective.And I think this speaks to how even now, like a lot of the work I'm doing is reframing why I love building and really reframing it of like, you know, we talk about how it's really important to build for the sake of like loving what you're doing, like loving the building you're doing and loving that you're helping to serve people.But I think there's always an aspect of people that's. Ego-driven that's driven by like what the outside, how the outside world responds to the things that you're doing. And I think in a lot of ways, what, what this transition has allowed me to realize is that for the longest time I was spending time building for other people, and I'm making this transition to really getting to a place where I'm grounded and whatever.However, I spend my time moving forward, it's doing it for myself, for what gives me energy. It gives me purpose and what gives me fulfillment. And so most recently with this transition, It was really hard because my ego was still latching on to, the role because the role had been my identity for the last six years.Morning Brew's been a hundred percent of my identity since I graduated from college. And so to me, it was a really anxiety provoking thing to think about once you strip me of that title, once you strip me of as close of connectivity with the company who am I, and I think it's a, it's a really valuable thing for me to realize the really valuable thing for me to work through.But from a practical standpoint, I think it made all the sense in the world for this transition to happen. Because today, at this point in time, maybe I'll like the things I'm talking about, like operational management, planning, process, all these things, maybe I'll like that later in life or in a few years more.But at this point in time, I don't love those things. if I don't love those things, I'm not going to be the best at those things. Those are the things that my co-founder Austin does love, and he's really good at. And I want to see the company succeed. I'm incentivized to see the company succeed. So why wouldn't I put the person who is, who loves and is best at those things in the position to do those things.Nathan: [00:09:19]Yeah, that, that makes a lot of sense. There's things that you said in there that really resonated with me. One is focusing on the early days of like, are you likely to start things? I like to start things. I don't like to start things from scratch, you know? And so the idea of now starting something new and having an audience and having like the leverage that you have now, like, it's like, oh, that's compelling, you know, doing ConvertKit over again from scratch and doing Morning Brew over again.Like that. To me, there's nothing compelling about it. Cause I'm like, oh God, so hard and painful, but I totally understand it. We were like, wait, if I, as who I am today with the networking connections and audience, everything that I have, oh, we want to spin up a new paid product. Yes. I'll dive all the way in and great that.Alex: [00:10:03]Yeah, totally. And I think that's like, that's kind of the beautiful thing about just business in general is you do have like this diversity of what brings people joy, right? Like you have, you have people who loves, who love building process and planning. You love having people who, who have a foundation and building on top of that foundation. You, you, you have people who have zero foundation. They want to just prove to the world and prove to themselves that the crazy thing that's been in their head that they think is valuable, but they there's no proof of yet that there's actually like people will love it. And so the fact that there's all these different brains is an amazing thing.Nathan: [00:10:44]What do you spend your time on now? You know, you're talking about we're before we hit record, you're talking about like open space and like, try not to make too many commitments for all the things.Alex: [00:10:55]The, the stuff that I'm spending my time on now, so how I describe it as for Morning Brew,I'm spending my time on basically three things. It is helping to ensure that the culture of the business scales as the company scales, you know, Morning Brew by the end of this year will be probably around 140 people.By the end of next year, let's call it 200. Plus what's been really special about this business is our culture. having people who are. Hardworking purposeful empathetic, who have a little bit of a chip on their shoulder to build something great. And the question is, is as you scale, how do you maintain that?Right? It's like every scaling companies challenge, I get excited by that challenge. So, that's one of the ways that I'm helping, the business still is to work with, Austin and with our head of people to think about ways that we scale this. This second is, is it's interesting. Right? I was telling you before how I went from being super in the weeds or in the mud to being out of the mud in the clouds.And it's like, I'm in a lot of ways back in the mud now, because now, like one of the things I spend a lot of my time on is as a creator myself. So building my brand on social building, my podcast founders journal, which I love doing. and the reason I love doing it is. I know that I would be doing it if I was involved in Morning Brew or not.And like, that's a great mental model. My mind is like, if I would do something on my own time, not within the walls of Morning Brew and I just have the opportunity to do it within it. It's a re it's a good sign. So spending time creating content. So hosting founders, journal, creating content at the intersection of like, it's almost like the, the w who I think about my audience being is like the mindful business leader.So like the person who's looking to elevate themselves as a business thinker, as a manager, as a leader, but also just like, as a person, because they understand it's all very intertwined. How you think in your life. Impacts the way you work as a professional, but also understanding business is really important to understand, to, to be a successful professional.So being a creator is a lot of my time. and then the third is honestly just acting as a top of funnel for opportunity by being a creator. It gives me leverage to have relationships by having those relationships. I can act as a top of funnel to funnel into the business in my kind of two major ways.One is on the advertising side. So as we scale Mortimer's business, both with advertising and non-advertising having relationships with big brands and agencies is really important. That's one side. The other side is actually on the creator side as morning, Bruce scales as a brand. And we start actually bringing in creators to Morning Brew's platform to, to launch shows and products within the Morning Brew, ecosystem in kind of like our music amusement park, the, the, the house of Brew, Getting B building relationships with creators will be, I think, a really big asset to bring in people to the Brew in a way they get really excited about our brand, but also we can launch great shows with them.Nathan: [00:14:10]Yeah. That makes sense. There's a lot of different directions I want to go. maybe before we dive into this, the scale and everything that you're going into now, maybe just give us like the high-level timelines of founding one in Brew, and then through a couple of those key stages with like subscriber counts and, and some of those things.Alex: [00:14:32]Newsletter, not called Morning Brew called market corner was a PDF attached to an email newsletter was sent out in, December, December 6th of 2014. It's when I was a senior at the university of Michigan. Austin was a sophomore, I didn't know, Austin at this time. First Morning Brew went out March of 2015.So my second semester, senior year, this was after I saw some traction with market corner. I wanted to bring on someone to help me. Austin raised his hand. He joined me as a co-founder of this non not really business, but project first Morning Brew in email form launch in March of 2015,Nathan: [00:15:13]What made you pick a newsletter as the thing to launch? Were there people also doing it? You know, you're in the finance space and all of that.Alex: [00:15:22]Yeah. It actually had nothing to do with other people doing it. It was really a function of, we asked ourselves two questions, one, what is inexpensive? Cause we didn't have a lot of money to spend on whatever content we created, that there was no, you know, there weren't easy, low cost ways to create content at the time.And then the second was. What is a medium that the college business student is already consuming, that we don't have to reprogram their behavior. So, like for example, an app app was interesting, cost a shit ton of money. We didn't want to, or have the money to spend on it. Website, website, not costly, but like how many websites are there that a person actually types in the URL, obviously, very few.And so the question was like, how are people going to find us then? Especially if we know nothing about like SEO or anything. So that's what led us to newsletters cheap and doesn't require behavioral change from the college of business student. So that was that, I ended up graduating from Michigan, worked in finance for about a year until there was a, to me just like a clear fork in the road had to do finance full-time or had to do a Morning Brew full-time.But doing both of them, wasn't a viable option. I quit my job September of 2016, right. Austin graduated from Michigan in June of 2017 and joined me full-time. So we're both full-time by middle of 2017. And I would say, yeah. So when I, when I quit, we were at, I think 70,000 subscribers,Nathan: [00:17:04]Okay. So it's a lot.Alex: [00:17:05]We're at 77,000 subscribers.We hadn't made a dollar yet. we, so other other important dates, we from 2018 to 2019, we went from a hundred thousand subscribers. So just to give you context, it took from September of 2016 to 2018, it took that long to gain another 30,000 subscribers. And then from 2018 to the beginning of 2019, we went from a hundred thousand subscribers to a million subscribers.So that was like a big inflection point for the business. What caused that? That was honestly getting the flywheel going of paid acquisition. it was the way we always come conceptualized. Our business was when we had our first newsletter. If our newsletter was the business.It was step one, create great content to get that great content in front of a great audience.And step three, get that great audience in front of the right advertisers. Once we had that process going, we were getting money from advertisers. Then we could say that cashflow from advertisers, we can either invest in people to assign to one of these three steps to get the flywheel spinning faster, or assign it to paid marketing, which we had never done before.And so by ramping up, paid mark marketing and doing it in a smart way where we were trying to acquire high quality subscribers, which at the time we defined as someone who opens at least five of their first 10 newsletters, that's really what got us to grow quickly between 2018 and 2019. And then 2019, starting in 2019 is really when we tried to go from newsletter, like, a newsletter as the company.To a newsletter company where it was a portfolio of newsletters, not just one newsletter. And then it was call it like 2020 when it was really thinking about newsletter company to true media brand outside of just newsletter as the medium. And those were kind of like the key dates in the company's history.Nathan: [00:19:08]Yeah, that, that makes sense. and then when just verbose context was the, the sale to the SunSetter. It doesn't require a majority stakeAlex: [00:19:17]Yeah. Yeah. So we closed on the insider deal in October of 2020. so however many months ago that was, you know, seven, eight months ago.Nathan: [00:19:28]I want to talk about the data acquisition side of it, because so many people are building newsletters through free content. you know, any of the original blogging crew, right? It's been running, newsletters are transitioned. That would say like search is one of their biggest channels, you know, organic search for driving newsletter subscribers.But I think a lot of newsletters, especially like single author newsletters,really aren't focusing on paid marketing nearly as much. So I'm curious, what are some of the things that worked? why did it work for you? When a lot of people get into paid marketing and, and they really struggle,Alex: [00:20:02]Yeah. So on the paid acquisition side, basically the idea is we wanted to accelerate growth. and we couldn't try like newsletters aren't inherently viral. Our referral program was doing well. And our referral program is what gave us the confidence to do paid marketing because every subscriber would be worth a little bit more than one subscriber since we could count on many of our subscribers to get referrals, but that wasn't what was going to be like truly create hockey, stick growth in our business.And, and so in a lot of ways, that's why, like, I think it's so important to emphasize if Morning Brew did not spend on PA like people talk about the downfalls of paid acquisition and you obviously have to be careful in your relationship with paid acquisition. But if we never did paid marketing, like Morning Brew has 3 million subscribers today, we would maybe be sniffing a million right now, like maybe.And so it just was so important for our growth and it was important to do it in a, in a way where we were at least trying to be smart about acquiring the right subscribers and understanding what channels, did well for us. And so, for example, like. Email newsletters was one of the best other email newsletters was one of the best channels for acquiring other subscribers.And so, but if you looked at it just on a acquisition cost basis, and that was the only way you looked at it, you would have never kept, advertising on email newsletters because it was very costly because let's just use the example that the average subscriber that we got from advertising and other emails was like eight bucks.And the average subscriber from Facebook was let's just say like two bucks. If you only looked at, in that way, you'd only keep pouring money in Facebook, but the quality of subscriber, the, the number of opens of an email newsletter driven subscriber versus a Facebook subscriber was completely different.And so that's why looking at acquisition cost of a high quality subscriber in the early days was like the number one metric we looked at for paid marketing.Nathan: [00:22:00]Yeah, so you have to have that longer term view. And that's interesting that you're saying of, you know, five open five out of the first 10 emails get opened because you have to have some kind of quality metric. Otherwise it's just, if quality is defined as a record in the database, then, then you're right.Like some random channel like Facebook or something else is going to be the cheapest, but not the best in the long term.Alex: [00:22:21]Yeah. And then again, like you're just running the R the arbitrage that so many websites have been built on is if you just acquire cheap subscribers, but they're not actually quality. At some point what's going to happen is like the cost of you acquiring those subscribers and how much a brand is willing to pay you to get in front of them.Once they realize they're not quality subscribers, it's going to invert and your business model is going to be broken.Nathan: [00:22:44]Yeah, that makes sense. Were there other things so beyond sponsoring other newsletters, were there other paid channels that worked really well?Alex: [00:22:51]There was, there was, an Instagram creative that did very well for us for a while, which was basically, a fake, a fake text conversation between two people where it was like one person was like, did you see an X so-and-so or something? And something happened in the news. The person responds no.How to hear about that, that the person responds, oh, it was in Morning Brew. and then like, whatever, it was a fake conversation, but it was one of the first, I would say examples of fake conversations as ad creative that did extremely well, because I think it felt, even though it wasn't authentic, truly, it felt way more native than a lot of different forms of ad creative.It wasn't overproduced. It was just an experience that a lot of people felt like they could share because everyone texts. So that did very well. YouTube advertising has continued to do really well for us. So buying a direct. Ads from YouTube influencers where they do like their own reads of them reading and re video, recording them, scrolling through the Brew while drinking a coffee at their, at their table that has done very well for us as well.Nathan: [00:24:03]Is that a lot of, well, so the first thing that I liked about that is that the money is going from wanting through to the creator, you know, rather than like, that's something that we run into that I can work at is like, do you really want to hand over all this money to Facebook and Google and everybody else when we could just give it straight to the creator?And so, I liked that approach.Alex: [00:24:23]It's true. And, and to that point, yeah, to that point, it's like, ideally yes. The, the, the biggest question just become scalability. Right? How do you scale that? Like, that was the biggest thing we saw with email newsletters is. How do you scale it for two reasons? fragmentation and, audience size. Like there are a lot of email newsletters that we burned through their audiences because we advertised in them so many times.So you just burn through audiences faster when you're working with let's just call like any form of micro influence or smaller influence than a platform that has multiple billion people on it. And the second is fragmentation, right? When you're advertising on Facebook, Facebook is the one place. and then obviously, like they can decide whether to put it on mobile, in what format on Instagram, et cetera, with like email newsletters or YouTube creators.You like you, it's a massive job. It's a super time consuming job in itself. If you want to scale a channel to say spending. $250,000 a month in email newsletter ad spend, like you end up having to either have someone in your company that spends all of their time on it, or you're hiring like an agency to be effectively the glue that takes the fragmentation of the email newsletter space and brings it together.Same thing for YouTube influence.Nathan: [00:25:43]Did you end up hiring someone in-house to do all that? Or did you first do it with an agency?Alex: [00:25:49]So we first did it with an agency. it was actually, one of the bruise investors in our, friends and family round. and then. So for newsletters, we were using agency for YouTube. We were, we were it's interesting. So it went from agency to person in the business that was managing the agency because like, it was a job in itself.It, it sounds crazy, but it's like a job in itself to manage the agency to make sure like they are optimizing the creators the right way. Or maybe some of these agencies, like don't have all of the creator relationships. And if we come across a creator that we think is a good fit, like that is a job in itself to recommend it to the agency, the agency to vet to then decide if they want to allocate part of the budget to it.So we have generally gone where we use agencies, but there was a person on the marketing team tagged to working with the agency partner.Nathan: [00:26:48]Yeah, I was smiling then. Cause we can work. I have done the same thing. We're like, oh yeah, there's an that with a person on the internal team, running the agency, you know?Alex: [00:26:58]Exactly and an agency. I think the assumption should be much to say you have T you have 10 hours of work on something for a person in the company. If you go use an agency it's not 10 to zero. It's like 10 to four.Nathan: [00:27:12]Yeah, that makes sense. I like the idea of, or everything you're saying makes sense about, managing the ads and the relationships. Cause then you're like, yeah, let's sponsor this. And it's easy to fork over five, 10, $25,000 for the sponsorship, but then there's like, what's the copy? What's the ad read winch, this all be timed.How did you handle tracking? That's probably the biggest thing that I could have run into of like, you know, Facebook rolls up your ad buckets and all you're tracking and you're like, there's your cost per lead? And in this case, right, someone doing their anger, you know, a pre-roll on their YouTube channel, it kind of sucks.Alex: [00:27:50]Yeah, they said that is, that is a, that is part of the four hours that, that like someone internally still spends on it. you know, it is literally managing a sheet of all of our growth partnerships. You know, it is working with our tech and product team to make sure we're generating unique links for every new influencer or marketing channel we're working with.Or we're AB testing copy. We're creating two links that have unique tracking and it's literally our marketing team is, managing a full effectively like database of all of these unique tracking links. And over a period of time, I don't know the exact period right now. They're going in and looking at what the performance is.And for YouTube specifically, like YouTube is different than like email newsletters, right? Because for, for email newsletters, you can assume, I don't know. In the first two days you're getting. 90% of the subscribers you'll drive from that advertisement, for the life of it. And then you'll get 10%.That's like the long tail for something like YouTube. My guess is it's closer to like, you know, 70, 30 or 60 40, because YouTube is effectively just, you know, a Google video. It you're going to con view like view count is going to constantly grow for the creator. Not just as more people are searching, but also if you're kind of taking a bet on the, the growth of the creator, if say a creator we work with today who has a million subscribers has 3 million next year, you're going to find a ton of growth on that video that you had this native promotion on, simply from them just growing as a creator.You don't experience that same thing with email newsletters because obviously it's scent and it's kind of in the past, irrespective of the growth of the email newsletter,Nathan: [00:29:35]So, yeah, that's true because the email has the upside of it's clickable. There was a UTM parameter on that link, all of that. But it's a moment in time promotion. Whereas the YouTube video is it's tied to that video or that series of videos and it lives there forever, which is the same thing that podcastsAlex: [00:29:54]Yeah,Nathan: [00:29:54]The same ups and downs.Alex: [00:29:56]I think I'll also say that I know was a really successful strategy for a few newsletters back in the day. I don't know if anyone's still does. This is, is like advertorials. so I remember, I think it was the hustle did an advertorial with hint water, where they wrote up like a, basically what felt like an editorialized piece on just the story of hint water, the story of their founder and CEO, Kara golden, and kind of like how they've revolutionized the flavored water business.And then what ended up happening was it lived on the hustles site. It had links out to hint, hint. Basically, they did all type shit ton of paid promotion to that piece on the hustle site. And they just kept putting money in it. As long as the return on ad spend made sense from however much money they were putting into Facebook and all these other social platforms versus how much people were actually buying hint water on the back of this article.And just from them spending so much money because they continue to see strong Roaz. I I'm pretty sure like hundreds of thousands of email subscribers came through that one advertorial,Nathan: [00:31:09]Email subscribers for the hustle.Alex: [00:31:10]Correct.Nathan: [00:31:12]So it's even more,Alex: [00:31:13]The advertorial piece lived on the website and pop up for the newsletter, came up as you're reading that advertorial.Nathan: [00:31:19]Oh, interesting. Right. Cause it makes sense. Like there's a version of that, that we did in the early days of ConvertKit. And honestly, there are these things that I don't know why we didn't do more of when you think that word. Why, why did we only do that once?Alex: [00:31:30]Totally.Nathan: [00:31:31]But there's like pat Flynn, who is Joe blogger podcast or he wrote this article titled why I switched from a Weber to Infusionsoft, to convert kit in like 2015, I think. And, it had his converted affiliate links in there. He presented to his audience that did really well. And then we went, that's a nice headline. What if we like to have to tells a nice story?And so we started running that as a paid ad to his, you know, he was even, he was even getting likes off and everything and it just, it converted so well.Alex: [00:32:05]In that scenario. You were, you were, you were Hintwater and PatFlynn was the hustle.Nathan: [00:32:09]Right. But I hadn't thought about that from the hustles perspective of they're like, yeah, you fit the bill, we'll write the editorial and lens the brand and the, you know, the website real estate.Alex: [00:32:23]Yep.Nathan: [00:32:24]Well,Alex: [00:32:25]I think part of the reason was that I think at some point Facebook started cracking down on it as they saw individual brands spending like. Millions of dollars on these advertorial pieces, which I'm interested in, why, you know, why, Facebook really cared. But yeah, I th I think that's the only reason, but it definitely was something that worked, for a number of brands.Nathan: [00:32:48]Yeah, you have like a whole thing. The morning group is very known for, if we were to mention referral programs related to email, in relation to email, someone would be like, oh, like Morning Brew. so I guess two sides of it. One, what were the things that worked for them for our program? And tell us a little more about that.And then I'm always curious when two concepts get so closely associated, I feel like then there's all these misconceptions that come from it and they're like, oh yeah, good morning. Where did this? And it's like, well, maybe they didn't or did some aspects of it.Alex: [00:33:20]We, we definitely, we definitely did not create the referral that is for sure. we, you know, okay. So the way it worked was.It was just a very linear process of thinking about how we could scale. Right? So step one was we had market corner that original newsletter, the way I got people to sign up for market quarter, because there was no website.You literally had to tell me, email your email address, and I would sign you up manually. So I told my early subscribers, I was like, if you know people who are interested in this and give you permission, let me know their email addresses and I'll type them in for them. and then I start getting email messages from random people saying, Hey, I heard about your, your Roundup called market quarter.Can you add me to your list? Serve? That was step one. Then step two was we launched Morning Brew. And we were like, how do we grow this thing? And Austin and I were still on Michigan's campus. And basically we were like, We, we need to, we have to think about it as like a hub and spoke model where you have these hubs, which are people, classes, organizations that have access to all of these spokes spokes, being the right audience you want to get in front of.And the way you save time is you get in front of hubs. So you don't have to go to every single spoke. And for us on Michigan's campus, the hubs were business classes, business clubs. And so we spent, I don't know, probably three or four weeks going to every single business class and every single business club on campus.And it was super successful. We'd go into a class. We would give the Brew spiel for two, two or three minutes. We'd say, Hey, if you're interested in it, we're going to pass around a sheet of paper, write down your email address and you can sign up. And that's what we did in every club in class. It was a great, like early bootcamp and just like.Doing things that aren't comfortable, like convincing a professor, why you should be able to sell something in their class. It was great for early selling and storytelling. And it was really good in thinking about just like an early exercise in conversion, because getting people to write on a sheet of paper, rather than asking them to take out their laptops and type Morning Brew into the URL, the old school more antiquated way did far better because you were just putting the utensil in the hand of someone and asking them to write it versus go through all of the steps.So that's what happened. And then we were like, we've cleared out Michigan. We have a strong hold on, Michigan. How do we do this in other colleges? Because Michigan is not the only college where students are going to care about better business news. So we were like, how do we find the Austin's? And Alex's in other places, that's what led to our ambassador program.So we had our ambassador program running and we were getting, you know, let's call five to 10,000 new subscribers a semester by working with ambassadors. And there's a whole story about the learnings of the ambassador program in the early days. But. Take the ambassador program, then we were like, okay. But we're seeing that they're actually people that aren't ambassadors there that aren't college students that really love Morning Brew because it's just quick, it's conversational.They feel like they're not talking to a robot. And so we're like, how do we make everyone an ambassador? That's what led to the referral program? The way we start our referral program is we first found out about kickoff labs. That was the website we used at the time. I think there's another one called viral loops, that we were looking at at the time.And we, we use kickoff labs and it was fine. And the reason we found out about kickoff labs I believe was because I think when Robin hood launched, I, if I'm not mistaken, they did their launch with kickoff labs to build up like a, the wait list for Robin Hood's launch. And so we started using kickoff labs.It was good, but a law allowed for no flexibility in our website. And so we couldn't do anything with our website. So we're like, this kind of sucks. We have no flexibility. So we're like, we need to, how do we build our own? We looked up how to build your own referral program. And of course there was, there was an article on Tim Ferriss's blog about Harry's razors and how Harry's razors use their user referral program.When they launched the company to build up an email list of a couple hundred thousand people. And in that was like this, this, the actual code for building out your referral program. Then we were like, okay, let's we want to do this. We went on Upwork. We found a developer in Ohio who we paid $500 to build effectively the Harry's razors landing page.Like it was the same exact thing, just different referral rewards and a different background rather than the wooly mammoth that they had. And, And the developer we found on Upwork had said that he had built this referral program like three or four times prior. So he probably literally didn't have to do anything.And it was just $500 in his pocket. And so we did that and then we ended up, as we brought developers onto the team to get it to scale, they rebuilt it in like a totally custom way. All that to say that we did not create the referral program referrals at their core, literally are just bringing scale to a friend, telling another friend about something they enjoy and being rewarded for it.That is exactly that is as old as time. And the technology is pretty old. Also like people think it's like, like wizardry and it is really the simplest tech. but we've found it to be so valuable. The reason we find it to be valuable is we found rewards that incentivize our power users, and we feel really confident about a product that gets our readers really excited to share with their networks.If either of those two things didn't work like the rewards weren't good. And it was a friction lit, it was a high friction process or the newsletter and our content wasn't good. The referral program would never work. And I think a lot of people say they want to do a referral program and they're either not thoughtful about the rewards or they're not thoughtful about why a referral program does or does not make sense for what their product is.Nathan: [00:39:17]What are some of those examples of rewards either in general that, you know, do, don't work, or more specifically from what you learned in boarding group that worked?Alex: [00:39:25]So what I will say is a lot of people try adding a referral program to a, what I would say is more of a marketing driven newsletter. So people who have like a weekly newsletter that is a Roundup of links from their website, they strapper a referral program to it. And they're like, we're not growing really fast.It's not doing anything. And I guess the question is one, do people actually give a shit about your newsletter? Why should they give a shit about your newsletter? If your newsletter is just content marketing for your website, you want people to give a shit about your website and your newsletters, just a vehicle to take them there.So why do you think people are going to share the newsletter and ultimately they end up on your website and the content they like is on your website. So that's the first, the second is it's always about like referral prize reader fit. And what I mean by that is like really thinking about. Who are the people who are going to want to refer your product and what is going to be the thing that gets them over the edge that takes them from mentally being like, okay, I'm on the subway.I like have five things I could do. And the thing I'm going to choose to do now is refer like what's going to get them to that mental state. What is going to be the thing you give them that gets them to that mental state. And so it's about knowing, like who are the people that are most likely to refer it's most likely going to be your power users.So then it's a question of like, who are your power users? And for Morning Brew, the power users are people who consider themselves to be a part of the Morning Brew community who feels so grateful that Morning Brew has become a tool for them to be a smarter, better professional. And for people who like really feel like they believe the Morning Brew brand, because they feel a part of the community.And so the question always was what are the rewards that make someone be able to either get more of the content. That makes them feel smarter and better in their career or what are rewards that allow them to show off their status in a community that they really feel a part of. And so that's why like everything from morning routine shirts to Morning Brew mugs to Morning Brew, crew necks, those were a combination of things that accomplish two things.One. Give social status to someone who really identifies with the Morning Brew community, but also turns them into walking billboards because they're products that you don't just have in the comfort of your bedroom. They're things you generally have either in an office on your desk that people see that like, that are seen in high traffic areas.The other was doing things like a Morning Brew, Facebook community, or our Sunday edition, the light roast, which up until very recently, you would only get access to if you got three referrals, like putting content before behind the referral world wall made people not only feel special, but felt like they were getting more of the content that they love Morning Brew for.And so it was that balance of understanding who would share, giving them a reason to share, and also doing so in a low cost way where we were really purposeful with picking rewards that were effective but efficient. So the acquisition costs from generating referrals, wasn't super high, for example, like.Our Sunday edition, the Facebook community. Those are cost. If you want to add a cost it's whatever the time cost is of the employee who has to moderate the Facebook community or write the Sunday edition for something like mugs, mugs are one of the cheapest forms of paraphernalia. It's like 23 cents a ceramic mug.So the, the referral cost of a mug after getting it bought and shipped is super low.Nathan: [00:42:56]Yeah, that makes sense. Because a lot of people will default to these really expensive, you know, items or something like that. And I liked the connection that you're talking about. It's because it's not the value of the reward or like the monetary value of the reward. It's incentivizing more of those behaviors.Like the t-shirt isn't like, oh, you gave me this thing that maybe I would have bought for 15 or $20. It's like, no, no, no. I have this Morning Brew. T-shirt. That I can only get by, you know? Yeah.Alex: [00:43:25]We're sending you your Jersey.Nathan: [00:43:27]Yeah. Oh, that's good. Okay. I want to talk about monetization because you've been heavy on sponsorships and advertising, for a long time.Curious if you've done other things, but you're also now into paid products. and so we take this in two sides. One, the like warning Brews are committed. We start there and then I'd love to also with go into newsletters as a whole paid newsletters versus, you know, all of that. Yeah. Give me your take.Alex: [00:43:59]So, okay. Well, I guess I'll just give my thoughts onhow, like, how we made money with the Brew. So in the early days of the newsletter, first of all, we didn't know the size at which we would be able to make. Money. I actually think in retrospect, we could have started monetizing earlier. And it's funny in retrospect, because we were really worried about like the sanctity sanctity of the brand, which is why I think what delayed us spent, getting advertisers to spend with us in that, you know, now hindsight, like I think as long as you, as long as you're doing native advertising with partners, you align with in a way where you don't have too much ad load, it really should not be a concern.And if that's a way you monetize your business, you need to do it in order to run a viable business or, or you should just think about other business models of you're really against advertising. and so we, I think we got our first advertiser around 75,000 subscribers. I've seen certain sub stackers.Get advertisers with way fewer subscribers. probably at 25,000. I think the earliest I've seen a newsletter monetize itself, through advertising is probably 10 to 15,000. And again, you're not making big money, but what you are doing is you're learning whether your audience actually responds to advertisers.And you're also building up a list of testimonials as you get bigger and bigger, that will be super helpful in selling advertisers, as you do scale, the, the initial advertisers. So the first advertiser morning, wherever worked with was a completely just through a relationship of one of our investors.One of our investors worked at an ad agency. He literally at the time referred to it as giving us some beer money. He got wa it was the first advertiser ever Morning Brew was, am Lockhart. And it was. College rings like college rings and like graduation stuff. They bought three ads in the Brew for 800 a piece, I believe.So $2,400 ad buy. And again, didn't, it wasn't a lot of money, but he got the process going about learning how to sell ads. And so basically from that point on, then the process was okay, how, what is going to be the lowest hanging fruit in order to monetize our newsletter? And what we said it was going to be is who are the brands that are most likely to advertise in the Brew?And what we came to the conclusion of is it will be smaller performance driven brands that could truly measure the ROI. or cared about the ROI of their ad. And so what that means is if they really cared about the ROI of their ad, they really don't care where they're spending, because it's not about just getting their brand out in the world.It's really about driving actual revenue. And so, you know, if they could advertise in a gas station TV, but that drives revenue, they're going to do it. And so our view is like focused on more performance driven advertisers versus brand marketing, driven advertisers and to let's start with what we consider like the chronic newsletter buyer let's see.And what we literally did is we created, And email address of newsletters@morningBrew.com or something like that. And we signed up for 50 different newsletters and we would track every day in a spreadsheet who are the companies advertising in those newsletters? Because our view is, is if you see a bunch of companies advertising those newsletters or, companies that are advertising those newsletters, many times clearly they're bought into newsletter as a marketing channel, which in the early days was a big point of friction because people, either thought newsletters were dead.They bucketed them in a certain place in their mind. And it was really hard to get people over the mental hump of should they advertise it a newsletter. So we went after performance driven brands that already had advertised in newsletters. That's where we started our, our focus. We also, in the early days, worked with an agency that focused specifically on working with CA call it these like chronic newsletter brands to place them into newsletters then as T and the way that we scaled this was, we basically just said, Well, the content has to continue to be great.We have to continue to great get engaged readers so that we're driving ROI for these advertisers. It also validated for us that we had really a really strong and, a really strong and just loyal audience in the early days, because it's one of those things. When you work with performance brands, if your audience isn't loyal and isn't engaged with the brand, like you can't fake it, it's just like, you're not going to drive revenue for these brands.So I think it was a really good early proof point for the value of the audience we were building and the way we scaled revenues, we literally just said, okay, let's say we were charging a thousand in ad. Let's just keep raising it. And we just kept raising it every single time. We talked to a new advertiser until the point in time at which.Advertisers said, Hey, like consistently said, Hey, we're no longer hitting our return on ad spend targets. we need to like, we, we, we have to cut you guys off at it as a channel. Then once we got big enough and I would say big enough was really at like 200,000 subscribers. That's what we were considered.I would say at scale enough. To work with big brands. I'll also say that having the testimonial or like the case study of working with a big brand before that 200,000 point, also helps in getting bigger brands. So we worked with the biggest, the first big brand we worked with was discover card. The only reason we worked with them or were able to work with them is because we had a relationship with the CFO of discover card because the CMO of discover card was a reader who found out from their kid who found out through the ambassador program that we were running at their child's school.And so this, we, we didn't, it kind of like was the hack to, to not have to convince a brand marketer why they should advertise it a small newsletter because the CMOs saw the value of the audience. They were the audience and they didn't care about that. They just said, allocate some budget to this Morning Brew thing.And so that case study not only created a mental confidence, that we could talk to big brands, but it also was something that we could show to big brands to convince them, like you're not going to be the first one who has to take a risk on this small newsletter.Nathan: [00:50:33]Yeah. Having that, that proof point is so important. And like, we had the same thing with ConvertKit where like Tim Ferris would be a great example. Like so many people would come to us and say, can you actually handle this? Like the handle, the scale and all that. And then once we had Tim's list on there that he goes, oh, Oh, Tim uses Yanga and like the whole list of like due diligence questions or whatever.They just like scrap all that. And, you know, and once you get that, it's so important and your rights, and a lot of those initial things can come through like a backdoor aspect of it.Alex: [00:51:05]A hundred percentNathan: [00:51:06]What about like, what's your take on, on the, paid products and paid newsletters versus sponsorship, like, in the sub stacked newsletter world, we take two examples would be like Lenny Rachitsky and, and Packy McCormick, right? So Lenny has his paid newsletter pack is like, forget that I'm going sponsorship. It needs a better model. And I always love people showing those, those two sides of it because you can do it a ton of different ways.Alex: [00:51:31]I don't think there's one way that works better. I think, hook, I think what sits at the core of this is are you building an audience or not? If you're building an audience like a true audience, like a trusted audience, you can make either work, like I guess said differently. Do I think Paki could have a great livelihood right now?With a subscription based newsletter. Absolutely. Like I think people pay for package subscription. I think you'd be making as much as he made in his last job. Would his subscription business be as big as his advertising business right now? I don't know, but to be honest, to be totally honest with you, I don't know that it matters because I think once you get to a big enough size, you'll end up having many revenue streams, not just a single one.And so I think it's like many paths that lead to a similar place and same thing with Lenny. Like could Lenny be making a great livelihood with his more product focused newsletter? Yeah, absolutely. I don't know how it would be doing relative to his paid version, but what I would say is it's more about trade-offs right.So. I think by having a paid community by going paid first, it gives you the confidence and it gives you the relationship with your subscribers to do other paid things with a level of confidence. Like if you're Lenny and you go and do. Courses, which he's done. It gives you confidence to do that because you already have an audience that you know, is willing to pay for your stuff.And to me, this is just an, a, an LTV driver for a portion of the people who are willing to pay for your newsletter. You know, for Packy, maybe the trade off is harder because Packy won't necessarily have the confidence day one to go launch a cohort based course, because he has no idea of the audience has the affinity to take out their wallet and pay for it.That said on the other side of the trade off is. Paki is going to have the ability to drive a larger audience because his content is able to like, you know, his content is able to maintain its vitality because it is open to everyone. And so, I'm kind of going to be Switzerland here, but it's like what I truly believe, which is, I kind of don't think it matters.I think it ends up converging where you monetize yourself in multiple ways. If you asking me, what would I choose to do? I would choose to CRE to keep stuff free for as long as possible to open up my audience as much as possible. But I don't think there's like a clear time in which I would close it off.I really do think it is based on field.Nathan: [00:54:11]One point that I hear in that is that the connection with the audience matters a ton.Alex: [00:54:15]It's everything. You either have a real audience or you have no audience.Nathan: [00:54:20]I like it. cause that's where all the monetization methods, everything else can, can get sorted out from there depending on what you do. So, I think that's good. last question that I wanted to ask you about. And this is more like a, a meta business question and projects. And all of that is I see people like two different types of ventures that people start.One is the, like, I'm going to start a newsletter letter. I'm going to start a blog, any of that. And they build it up. It has like side hustle, the full-time vibes to it. I don't know how else to describe it. And there's other people who start something and you're like, it's a force of nature. And it like turns into something like one number where it's millions of subscribers.You see it, even, you see it, startups agencies, like one person starts an agency. And like years later it's like five people and someone else starts an agency and it's the same business model and all that. And years later it's like, I don't know, VaynerMedia, or something on that scale. And so I'm curious when you see, how do you think about those things?As one of those people who's taken like a newsletter, which is typically a small business and grown it into something massive.Alex: [00:55:31]When I, when I reflect on this, I really think it's about ambition, right? Like, I think it's based on ambition and risk tolerance.On one side you could say morning bruise, massive on another side, you could say, Morning Brew actually potentially could be bigger right now, if we raised more money, we are aggressive, more aggressive in our growth strategy.And for the people, like you say that their thing is less of a force of nature. It's interesting because maybe their goal is if it turns into a force of nature, that's great, but maybe they don't want a force of nature. Maybe they just want something that literally opens up their time to do anything else in life.So, I don't know. My answer would be that while to have the opportunity for something to be forced, to be a force of nature. I think it really has to be something that serves a specific audience in a really exceptional way. And it's an even better case if it's a growing niche. Like I think people think about niches as small.And obviously like now people talk about all the time about niches and small. It's just focused the ideal scenarios where it is focused and scaling. So like, what is a trend you're latching onto that say has a hundred thousand people possible audience today, but like 5 million people, five years from now.So, I think that is one piece of the pie where you have to have that to have the chance of being a force of nature. But then I think you have people who have not become forces of nature, maybe early making 150K with their product, but. Maybe the reason they don't have that ambition is because ambition requires time.And that time they actually think there's an opportunity cost too in spending that time elsewhere in other aspects of their life. And so, like, that's kind of how I think about it is, it's it's ambition, you hear the word ambition and you're like, oh, that means someone really wants it, or they don't really want it, but maybe there's actually more nuance to it where it's like, Not that perse someone really wants or not really want something in life, but it's actually the reason they really, maybe they really want something.Maybe they really want to make their thing, a force of nature because that's what they're super passionate about. And that's where they would love to give their 70 hours a week. Or maybe you have someone who is not a force of nature. It actually is a great product market fit and it's a scaling niche, but what they really want is giving 30 hours a week and the other 60 hours a week, they're spending with their kids.And that's not to say people spend 70 hours a week. Don't want to spend time with their kids, but I think there's a spectrum. And that's how I think about it.Nathan: [00:58:08]Yeah, that makes a lot of sense. And I think we see people scale up any of these opportunities when they have leveraged coming in that they're able to, to either scale something crazy, or they're able to use that leverage and redirect it to something else.Thanks so much for talking today.Where should people go to listen to your podcasts, follow all the new stuff you're creating and then yeah, everything else?Alex: [00:58:32]Yeah. you want to follow me on Twitter? It's @businessbarista. And then podcasts just on any of the players. It's called Founder's Journal and, three days a week, eight minute to 12 minute episodes. And the whole idea is like accelerating your career as a, as a monitor business leader.Nathan: [00:58:50]I like it. Well, thanks so much for coming on and we'll have to chat soon.Alex: [00:58:53]Yeah. Thanks so much for having me.

On this week's episode of Inside Outside Innovation, we sit down with Alistair Croll and Emily Ross, co-authors of the upcoming book Just Evil Enough. We talk about the changing role of marketing and how companies can subvert systems, undermine industry norms, and get platforms to behave in unexpected ways that tilt the scales to generate attention and demand. Let's get started.Inside Outside Innovation is the podcast to help you rethink, reset, and remix yourself and your organization. Each week, we'll bring you the latest innovators, entrepreneurs, and pioneering businesses, as well as the tools, tactics, and trends you'll need to thrive as a new innovator.Interview Transcript with Alistair Croll and Emily Ross, Co-authors of Just Evil EnoughBrian Ardinger: Welcome to another episode of Inside Outside Innovation. I'm your host, Brian Ardinger, and as always, we have some amazing guests. Today we have Alistair Croll and Emily Ross authors of the new book, Just Evil Enough, which is a book about getting noticed in this noisy environment and subversive go-to market strategies. Welcome to the show guys. Alistair Croll: Thanks for having us. Emily Ross: Thanks a million. Brian Ardinger: Well, I'm super excited to have you on this call to give our audience a little bit of a sneak preview of the upcoming book. But first let me give a little bit of background. So, Emily Ross, you are a founder of a tech marketing consultancy company called Ink Vine based in Ireland. So we appreciate you coming across the pond to give us some insights on what's going on. And Alistair and I go back a long time back in the days of Lean Startup. And he's the coauthor of Lean Analytics. We brought him back to Nebraska about six or seven years ago, I guess it was, when I was working with Nmotion to help with our startup teams in that. So thank you for both being on the show. The title of the book, Just Evil Enough. How'd  you come up with that  and what's it all about? Alistair Croll: So I'll tell you a quick story. We ran an accelerator in Montreal called Year One Labs. And one of the companies in Year One Labs was a company called Local Mind. And Local Mind was a platform for asking people questions, asking strangers questions about an area.It was later acquired by Airbnb and Lenny Rachitsky,  the CEO ran supply-side growth there. And he's now the author of one of the most prominent newsletters for startup growth marketing, Lenny's Newsletter. And in the early days they were doing what every startup does, which is building lots of stuff. But because we were very Lean Startup focused, we have them ask what the biggest risk was.And it turns out the biggest risk was that whether people would answer questions from strangers. So they ran a very quick study, which we talk about in Lean Analytics. And they found that 94% of people on Twitter would answer a question from a stranger. But this happened because I had been asking Lenny, are you being evil enough?And they were like, we're not evil. And I said, yeah, but just a little evil, because it turns out that people answer questions, but people on the platform won't ask questions. The real risk is the supply of questions. And so they actually built a system that would ask fake questions of new users. So they get in the habit of asking questions. Now you can debate the means versus the end, but what we have found ever since that time is that almost every startup that's successful has some little dirty secret in their background, where they were able to take advantage of an emerging technology or subvert the way a platform is supposed to work and turn it to their advantage.And so the basic idea behind Just Evil Enough is that almost all the time, the problem isn't whether or not you can build something it's whether anyone will care. So your job should be creating attention you can turn into profitable demand. Emily Ross: I think the subversive word is really, really important because we want to clearly differentiate between nefarious, which is downright evil and subversive, which allows you to think a little bit differently.And it's very hard for people who've been conditioned to think a certain way, to try and think differently.  So the book is about trying to teach people how to think subversively, and to show examples and frameworks in order to do that. And I remember working at a platform years ago and one of the engineers said, right, I'm going to put this button on the website to test if people will click it.And my instant reaction was, but it doesn't go anywhere. That's a terrible idea. They're going to have an awful experience and that's bad for them. And he's like, no, but I don't want to build something unless I know they're going to need it. So I'm just going to put that button there and yeah, I'm going to burn a few thousand clicks and they're gonna have a terrible experience. I don't care. I'll learn something. And he was prepared to be disagreeable in order to learn something different and to save an awful lot of time and money. And it was funny. It was like, okay. I need to think a little bit differently about how we're treating users sometimes. Alistair Croll: Yeah, we did a similar thing at Gradient. We had a reporting feature. Gradient was a startup that I launched in 2001. Eventually got acquired by BMC, their TrueSight product line. And we were about to launch reports in the product. And so we created our reports tab, and the reports tab went to a survey page. It says, we're going to do reports soon, what would you like to see?And people put in their email address and the report they'd like to see. And of course we were building a generic reporting tool. So what we did is we then generated like the top 20 requested reports. Made them defaults and then mailed those people saying we loved your feedback. Thank you so much. We've built the report you're looking for. Forget about the fact that 40 other people ask for the same report. Every one of them felt like they were a unique and special snowflake. And so we were exploiting the asymmetry between what we knew, which was 20 people asked for it and what they knew, which was, Hey, look at this, I'm special. You listened to me. And the customers loved it. Right? Is that evil? Well, it meant that we were able to build the default reports people wanted, which made the product better, but it's a little subversive. Brian Ardinger: Well, I think part of that learning is the fact that I think a lot of people think that they need to build the entire thing, because that's what shows the value. But, you know, again, you have to incrementally de-risk some of these new startup ideas. And so how do you do that with building just enough to get the learning that you need so that you can move it to the next level and build it out if you need to? Alistair Croll: Well, I would say that the problem's not minimum viable product, it's minimum viable attention.Emily Ross: Yeah. And actually, if you think about, and this is the one thing that the book, I suppose, hammers home, is that getting your go-to market strategy right, is as important, if not more important than getting your product right. Because if you can't capture attention and turn it into profitable demand, then no one's going to know about your product. And it's all about various different approaches that you can use to figure out how to do that. And  asymmetry being just one of about 10, I think that we cover. Brian Ardinger: So, is it a form of customer discovery almost so rather than the traditional customer discovery interviews there, you're looking for different ways to engage with a marketplace, engage with a customer to get that understanding of what their demand is and where they want to go from there?Emily Ross: Well, it's really interesting. Some of the examples in the book are not business examples. There's a lot of historical stuff in there, right back from Machiavelli,  all the way through to The Godfather. There's businesses, oh, tell the Genghis Khan story. I love that one. Alistair Croll: So I mean, the idea behind a lot of this is that if you know something to be true, that other people discount, you can take advantage of that. And there are many times where people knew they could do something better, but didn't Genghis Kahn, for example, knew that women could be very effective rulers. This was something that was not widely held. And so he would conquer a city, marry one of his many, many daughters off to the leader of that city. Send that leader off to war, he'd promptly get killed. Now you have a blood relative in charge of that city. Was that evil? Well, Genghis Khan did a lot of nasty things, but he did have a decent amount of respect for women's ability to run cities, which was something nobody else was factoring in. And this was an unfair advantage. Right. And I think, I mean, we're getting a little ahead of it. One of the things that Emily talks about a lot, is the idea that you need to know the norms of your system in order to subvert them. So do you want to talk a little about the water stuff? Emily? Emily Ross: Yeah so normative versus formative is like super interesting. So there's a story of by two fish and they're swimming along, and a much older fish is swimming the opposite direction. And this is from... Alistair Croll: it's a commencement address, right?Emily Ross: That's it, the older fish says, Oh how's the water? And the fish swim on a little bit and they turned to each other and go, what the hell is water? So, you have to be able to recognize the fact that you're swimming in the medium. And the best way to do that is to use external viewpoints to help recognize what you're swimming in or downing  in.I also use a log jam metaphor, which works as well. And this is a one I use all the time for teaching for problem solving, but it's really, really applicable as well too, to recognizing the difference between normative and formative. So when these to say a logs down the river, to ship them to the log yard, And they would occasionally get tangled up and a team of river pigs used to have to surround the problem really quickly because it's obviously getting worse and worse all the time, and figure out which was the one key log that you could extract to unlock the whole problem.And the only way they could do it really, really well, was through diversity of thought, opinion, and perspective. By surrounding the problem, by sharing ideas, by looking at it from lots of different perspectives. And that's why diversity in your teams, that's why diversity of perspectives is so important so that you can actually recognize what you're swimming in, whether it's water or something, a little bit stinkier. And also getting the sense of looking at it from outside, what you're used to. So ideas from different verticals, from different walks of life. That's going to help you think subversively. Alistair Croll: And that's kind of the supervillain stuff. I mean, Brian, I'll give you an example, that's a concrete example from when I came to visit you .One of your startups was making a rotary sprinkler solution.So to recap, rotary sprinklers, when they're lateral to a strong wind, get blown over and this costs a lot of money to fix. And so they built a thing that could measure the weather and the incoming winds and rotate the sprinkler downwind kind of like a wind sock, so it wouldn't fall over. And they're having a hard time selling. And what the startup revealed to me at the time when we were meeting, was that there's this weird existing system between farmers, farm subsidies, insurance, salespeople, and the makers of those sprinklers.They don't really mind when it gets knocked over because everyone makes some money and then they use that money to go on a fishing trip. If you don't know that you're in that water, all your efforts to sell are going to fail. You've got to recognize that and then go, huh? Maybe this is something I can sell through the maker of the sprinklers, or like maybe I can, you can subvert that system.Maybe you have to create an awareness campaign that farm subsidies being wasted and they could be spent on something else. But if you don't know that strategy, you can't subvert it. And that word subvert just means find another version. By definition, the hardest problems we face are the ones for which we don't have an obvious solution, because the normal approaches don't work.Which means you've got to find an unusual approach and that's normally called hacking, right? Hacking is getting something to work in a way it wasn't intended. Whether you're using a Pringle can to focus wifi signals, or you're getting a computer system to throw an error, so you can own a system. The problem with hacking is that in startups, hacking has a horrible polar reputation. Growth hacking is a bag of cheap tricks.Brian Ardinger: Talk about some of the examples in the book that maybe some people have heard of or can get a visual around. I know you've mentioned in past talks and that I've seen around this is like things like Peloton or Burger King.  Can you give examples from that? Emily Ross: I would quite like to talk about one of the ones that I had the hardest time with is about being disagreeable. And we talked about it slightly there in terms of doing things that you wouldn't necessarily think of as being quite right. But as a woman, I have been raised to be polite, to be agreeable. And actually, if you look at some of the most innovative, interesting entrepreneurs in history, quite a lot of them have been profoundly disagreeable.They've been prepared to be unliked or unloved. And this is something, a behavior that you can adopt or think about as a means to finding new ideas, or it means of finding new ways of doing things. One of the examples that we talked sports a little bit earlier, but Wilt Chamberlain was arguably one of the best basketball players of all time. He has on more than one occasion scored over a hundred points in a single game. But he had a problem. He couldn't shoot free throws to save his life. Back in college, he had a really high score, but over his career, it went down and down and down and he had a career low of like, I think 26% success rate.He was a star player. He got fouled a lot. So this was a really big problem for him. So he went to see Rick Barry. Rick Barry was the guy who could not miss. He actually had a career average of 89.3% and he got better and better as his career progressed in the last two years of his career, he had a 94% success rate from free throws. But he actually threw in a really interesting way. He threw underhand, which is actually kind of a cool word for the, Just Evil Enough book, because he shot underhand. But he was the best at shooting. But this was called the Granny Style. This is, you know, if you throw like a girl, you throw under hand. He didn't care. His father had drummed it into him from a very young age, how to shoot underhand, overhand, underhand, overhand, and he could just nail it every single time.So Chamberlain went to see Barry learned to shoot underhand and his performance doubled. He went from a career low, to a career high, in that same game where he scored a hundred points. So it turns out it's a much better approach. However, Chamberlain didn't have the guts to keep shooting underhand because he cared too much about what people thought. His career best was 61% from the line in 1961, he sank 28 of 32 free throws against the New York Knicks.So after a while, though, he reverted to shooting the way he knew, and his percentages  plunged. And he admitted that he felt like a sissy. He worried too much about what other people thought. And unlike Barry who was rational, Chamberlain was being agreeable and wrong. Barry meanwhile said he could be as selfish as he wanted to without hurting his team. So being a little bit disagreeable or asking yourself what you're prepared to do is a really good first start. Alistair Croll: Just to chime in quickly, we've all heard of growth hacking right? Growth hacking is these little tricks that get people to click a button or move down a funnel or whatever. The problem with any of these known tricks is that they're known.  Andrew Chen talks about the law of shitty click-through rates, which is simply the idea that as you find a vulnerability, if you will, a way to change the market, it becomes widely known immediately.So the first click-through ad on Hot Wired had an average of 44% click-through rate. Some people say it was as high as 70% for a banner ad. What's that at now? Emily? Brian Ardinger: Well, industry averages will tell you, or they'll tell you it's 0.1%. But in my opinion, it's closer to 0.02%, if you're lucky. Alistair Croll: So that's a huge decline. Same thing happened with email and so on. And so there are these known hacks that are the sort of marketing equivalent of a script kitty, who's running an attack on WordPress. And if you haven't patched your site, you'll be selling Viagra off your website. What you should be doing is trying to find the marketing equivalent of a zero day exploit.So in security a zero day, is an attack that nobody knows about yet. And they're incredibly valuable. Two of them were used to retard the Iranian nuclear program and damaged centrifuges. The marketing equivalent of a zero day exploit, we call this zero day marketing, is finding a new way to get a platform to behave in an unintended manner, with which you can create attention you can turn into profitable demand. And there's some amazing examples of like Farmville, for example. When Farmville's app would send you a message saying, Hey, Brian, Alistair's cows need some grain. And you'd click on it. Now you're a user. Well, they got to 30 million users before Facebook went, Whoa, we maybe don't want apps posting to people's friend feeds.There are so many examples of this, and we can tell you those examples. But the point is you can't use those examples because they've already been done. Right? What you have to do is devote much more of your time to inventing your own zero day marketing exploits. Brian Ardinger: So from that perspective, is it a series of experiments that you just have to run? You, you come up with some ideas and you run them like that, or is this, talk me through the process of how you get better at it? Emily Ross: One of the examples that I like to share, if you see it often enough, you begin to understand how you can apply the thinking. It's a model and you just try and apply it to your own environment. So if we take the information asymmetry, and example, the idea of subverting, one thing for another. Or a bait and switch. The idea of you're selling one thing, but actually getting another and Tupperware parties did this, you know, you think you're going for dinner and you end up getting guilt ridden into buying a load of plastic.But when I was working in a comparison platform, we subverted the PR channel for the generation of white hat backlinks. So PR is generally around building brand and brand awareness. But one of the side effects of PR was the generation of backlinks. So this is back in like maybe 2013. So what we did was we mined data. We attached big data trends to celebrities, pushed out, press releases to high value domains, and pretty much one in five hit would generate a backlink. When we started. We had about 1400 high quality backlinks. And we were generating about 60,000 non-brand organic visits to site per day. And after three years of pushing out two releases a month, month in, month out, we had over four and a half thousand unique domain backlinks and almost 200,000 non-brand organic visits per day.And this was a platform that turned traffic into money. I won't tell you how, but what we did for example, was we mined hair transplant trends and prices. And one example of the many, many crazy pushes we did was the Jude Law index of baldness. So here's a scale up from Colin Farrell all the way up to Dr. Evil,  of how bald are you? And you find yourself on the index and you see, Oh, this is how much it would cost for me to have hair transplants. It was a price comparison website for private health clinics. And this was a fun, interesting way to attract attention and turn it into traffic to the sites. But actually it wasn't really about traffic. It was always about the backlinks. So one in five hits generate a backlink, but again, it was channel burnout. It was a zero day exploit because you know, over the course of the three years, the number of backlinks that were being generated, went from maybe one in five to one in 10, because the platforms themselves started to recognize the value that they were accidentally giving away.So naturally you get published in a paper. If there's an online version of it, they print it online and they put a backlink out. It was a side effect of the real, a pure PR. And channel burn happened, those backlinks are no longer as readily available as they were. But it worked for about three years, four years. It was a fun time. Brian Ardinger:  You have to have a continuous funnel  yourself of new things that you need to explore it. Emily Ross: Exactly.  Exactly. So that was a, we had a good run, but it's about thinking about, well, what is the channel? What is the platform? So PR was the channel and we used it in a way. It wasn't intended to be used for our benefits. And so what are your channels? How can you use them differently? And that's a really great question to ask of yourself, no matter what you're doing. Alistair Croll: One of the things we often do is. What has changed in a technology platform. So for example, Travis Kalanick has this new startup Cloud Kitchens. What has changed in restaurants? Well, first of all, there's a huge abundance of restaurants that I could order from. Far more than I would know about. So I'm already overwhelmed with selection when I go to order food, because we're all at home, in a pandemic, ordering food. And second of all, The fact that the storefront is virtual, it means one kitchen can have many restaurant front ends. And so Cloud Kitchens will set you up with brands and their brands have games like Fucking Good Pizza, My Pasta, Dirty Little Vegan Bitch, Don't Grill My Cheese. None of these tell you about food, but when you're overwhelmed, and you have that sort of paradox of choice, you go, no, I'll just order it from that one. That sounds fine. Right? That's only possible because that brand is part of an experiment. You're ordering from an experiment. And they're constantly testing, which ones get more attention and then the restaurant can deliver all of those things that might be the same kitchen. And so Cloud Kitchens has taken advantage of an exploit within the traditional model of food ordering. So it's looking at, you know, what technology changes or combinations of technology, makes something possible that wasn't possible before that you can then subvert to your ends. Brian Ardinger: How do you go from not just creating a gimmick or how do you, I guess also approach being wrong, like trying these things and, and being wrong?Emily Ross: Growth hacking is gimmicks. Growth Hacking is doing something that maybe it's a publicity stunt or, I mean, one of the examples that we use in the book is pairing two things unexpectedly together. That's a great way to draw attention and Heineken did this really well in the UK just last week, where they put out a mobile hairdressing units and bar, so you could get a free haircut and a pint together.So this generated publicity and it's nice, but it's gimmicky, right? Is that really going to move their needle? You know, for the year? Possibly not. It's a nice story. So, but if you look at governments have been doing this for years and they've done it so well, there's a really good example in the book, which I won't go into now about how the government shamed people into stopping spitting in the twenties, as they tried to fight TB. Instead of just saying it's bad to spit, they actually made people feel bad, and socially, and vulgar  by spitting because before that it was perfectly normal.And if you look at the Chinese government, they use Fapiao.  Fapiao  are receipts. And they use Fapiao  as a lottery to fight corruption. So this is really interesting. In China, corruption can be rampant. Merchants will give their customers a discount, if the customer doesn't ask for a receipt.So the merchant doesn't have to report the income and like just pockets to the savings. The government used an incentive to combat this called Fapiao, which is a receipt  from the merchant. And there's a couple of hacks in here that are super clever. So the merchants have to buy the receipts beforehand and then hand them out to customers in return for payment.So the first one is the merchant has to pay tax before the transaction. That's really smart. And then customers demand their Fapiao, because there's a scratch and win lottery element. And then the government runs the lottery and customers can scratch off the panel to see if they've won anything. And so the second hack there is create demand for a receipt by making it a game.And then of course the government can also adjust the prize amount of each lottery to create just the right amount of incentive. So they're literally able to alter the rewards of the game to like tilt the Nash equilibrium, which is just like super smart. So you can do this at a macro level and absolutely get away with it.Alistair Croll: I want to just make sure we address your question about gimmicks. One of the big differences between a Zero Day Exploit and traditional Growth Hacking is that it's not known. But another is that it is intrinsic to your business model. The haircuts aren't intrinsic to Heineken's beer, but when Dropbox launched, they were the first to pioneer this, both of us get something. I invite you, we both get storage. That's built into the product, right. That's intrinsic to the system itself. And I think what it means is that you're factoring in Zero Day Exploits, marketing exploits, to your business model and your product roadmap. Not just to your marketing campaigns. I mean, Genghis Khan's  a good example, right?It wasn't just a tactic. It was a fundamental change in how he thought that societies could be ruled. So the real lesson here is, I'll give you one more example. There's a company that makes software called Energage  and they make workplace surveys. So they would sell to an enterprise and the enterprise would survey their employees and do  360 stuff. And so on. But the way they go to market is they launched this thing called the top workplaces project in concert with the Washington Post, the Denver Post, the Dallas Morning News and so on. And they run this survey and they say to these newspapers, Hey everybody, here's the survey. We'll take care of it.So now you go do it. And like, Whoa, isn't this great. My company is one of the best workplaces. I'll buy an ad in the newspaper. Everything's wonderful. And then Energage can go back and go, Hey, congratulations on being the third best workplace in Nebraska. Too bad about the other results. And you go what other results? Well, you know, we got more data than that, would you like to see it? Okay. And now you have a new customer, right? It's intrinsic to the business model, right. Rather than just being a little trick or hack. Brian Ardinger: That's an interesting point. And it also goes to the point where you see a lot of these examples in startups, because you can build it early on into the business model and that. How does this play out for a large existing company that wants to try to use some of these tactics?Emily Ross: So big companies really need to think about reframing and they also need to give themselves permission to think in ways they're not used to. One of the exercises I like to recommend is called a pre-mortem. And you basically give them permission to imagine the worst possible outcome. You invite them to invent the worst, worst, worst thing that could possibly happen and then work backwards from there.And it's amazing what happens in an environment like that, because that group think is real. That tribal behaviors of wanting to be agreeable and wanting everyone to pull together is very much a systematic thing that you see in large organizations. So giving them permission to think disagreeably.  Giving them methods to reframe where they are, what they do. These are all great frameworks for them to try and think subversively. Alistair Croll: First of all, I think that it's really important. I mean, I would consider a marketing department, have a Red Team. Have a second group, hmm, that has the same product and resources, but their job is to put the first group out of business. What do you do? Right. That's just hypothetical. You're going to think better. We Red Team on security. We Red Team on PR. Why don't we read team on go-to-market strategies.  And the second thing is, if you look at great brands that changed how people discussed a product or a service, they found a frame of reference that favored them. For decades we used to talk about electric cars. We would talk about sustainability and range. Pretty boring stuff, right? Lots of hippies sitting around going let's save the planet and look at my Prius. Elon Musk put one of them on a race track against supercar and beat it. And all of a sudden the conversation on electric cars was performance. He'd reframed the discussion about electric vehicles to performance, right?When Gmail first launched, your inbox on Hotmail or Yahoo mail had 10 mgs. That's like one photo, right? We don't remember that. My daughter doesn't believe this. When Gmail came along, Google knew that they did not have strength in folders and archiving and hierarchy and export, but they were good at with search and storage.So they said, Hey, email's not about your ability to manage your folders and your inbox and organization and management. It's about abundance storage. And they reinforced that so much that they actually had a counter showing you how much storage you get. Salesforce, when it first launched, was a web based CRM, but web-based CRMs had very few features compared to Siebel and Vantive and Clarify, companies that you don't see anymore.So they said no CRM is about not needing IT. In fact, their logo was no software. They had us the word software with a slash through it, despite the fact that they own their own programming language called Apex. Right? And so each of these companies found a way to reframe things, even like Listerine. Listerine was this clinical health thing. And then along comes scope and says, Hey, you know what? Mouthwash is actually about being attractive and sexy, not about clinical health. One action that a lot of big brands should take is to step back and say, what is a new frame that favors us and disadvantages our competition. And then what is it about that frame of reference that we can do to prove it that will then allow the customer to find a different way of valuing the product?Emily Ross: I would also chime in there and talk about generally large marketing teams will have, they'll have done their marketing degrees and their MBAs or masters on they'll turn out the four P's from, you know, the 1960s or the seven P's of service. And like there's too much P. Just stop peeing. Guys just stopped doing it.Right. Chuck, all of that in the bin and start thinking about creating attention. And it's as simple and as complicated as that. We talk about human motivation and Alistair  I think coined laid, made, paid, afraid. I tidy that up a bit to the piratey AARG. Which is appeal, authority, risk, and greed. So think about your customers. Think about your competitors. Think about the marketplace through the lens of human behavior and whether you're selling radiator bits or cars or Cola, people have all those very basic triggers. They want to be liked that's appeal. They want power that's authority. They want to feel safe. That's the risk lens.And then greed, you know, people want the things that they want. So. We're just human meat bags, right? We're just walking bags of meat with emotions. We have very simple motivations at the end of the day. And in a B2B setting for a big organization, the AARG framework is a really useful function. Like, so throw out the P. Think about AARG.And if you're trying to convince people to act, you need to appeal to base emotions more than you do plain reason, because most people really aren't very rational. There's also really a good examples of the seven deadly sins. If you look at the big, big enterprises, I think Chris Pack said this on Twitter.I thought it was really, really good. Uber and Amazon are slough. Instagram and Tik Tok are pride. Door Dash is gluttony. Tinder is lust. Pinterest is envy. Twitter is rath. And Bitcoin is greed. So think about the fundamentals. Just think about the basics. We haven't changed all that much. Alistair Croll: But I think the biggest thing here is that big brands haven't realized that the biggest risk they face is that someone else will subvert attention that they could otherwise be getting and turned into their profitable demand. And so if you don't do that, you're going to get eaten alive. If we can get the world to realize that the biggest risk is not whether you will build something, but whether anyone will care, we've already given people a huge headstart.Brian Ardinger: Well, and the fact that the world is changing so fast on the fact that you can go from company like Airbnb in 12 years to being, you know, one of the most recognizable brands, you know, overnight effectively from what used to be to build a business. New technologies, new marketplaces, new access to talent. All of that is just accelerating the opportunities to be disrupted. Alistair Croll: We used to have a new platform come along. You know, we had writing that took a few thousand years. Then we got to radio. It took a few hundred years. And then we got to television that took a decade, the rate of introduction of new platforms. And therefore, if you're thinking like a hacker new attack surfaces, Is incredible, right? The Cloud Kitchens example happened because of the pandemic and the rise of Uber Eats and Door Dash, and so on. The pace at which new exploit opportunities appear is very, very fast. And as a result, there are far more opportunities to subvert the status quo or the norms of your industry with one of these new platforms.So we're trying to get people to be much more opportunistic. And part of what we do, like I said I can't tell you do this thing, because if I tell you, then it's already been done. What we can do is we can say, here are some ways to think about it. You know, is there an innovation that happens? Can you reframe things? Can you do a substitution where people think they're getting one thing and they're actually getting another. Can you appeal to the foibles of human psychology? Emily Ross: Don't be afraid to be disagreeable. Alistair Croll: It's weird because in the past I've written books that are very technical. There is a right answer. And Emily's written lots of articles on like how to do stuff. This is a more subjective thing and candidly more uncomfortable for us as writers, because we want to make sure that there are applicable lessons, but it's almost like, you know, teaching someone Zen. I can tell you what it is, but you're going to have to go sit on a rock and figure it out for yourself.But once you start thinking this way, everything becomes a subversive opportunity. And once you have that subversive lens, you're not being evil, you're just being just evil enough. Opportunities are everywhere. Emily Ross: And actually, if you think about it, just coming back to your very first question, which is a nice cyclicity.  The title of the book is exactly what we set out to do, which is we got your attention and we're turning it into demand. So the book title is a really, really simple and effective way to showcase the thinking. And I think if you take one thing away from it, it's change what you spend your time on. So building a subversive go-to market strategy is just as important as thinking about your product. And if you get the balance, right, you're going to be unstoppable. Brian Ardinger: Well, and you've also from the book perspective, the book's not out yet, but you're doing things to grab attention differently than a lot of, I mean, I get pitched every other day by a book author trying to get their book noticed and that. But I know that you've been doing some things as far as live online course that's leading up to the book. And you have a interesting little survey. I don't, if we got to talking about any of the things that you're doing from a attention perspective to, about the book. Emily Ross: Well one of the things I love, this was so much fun, is that you can't just order the book. You can't just pre-order it. You have to take a quiz so that we can decide if you're evil enough. So you take the quiz and if you're not evil enough, we think, you know, you're not going to be able to handle the book. And if you're too evil, then this book could just perhaps be too powerful. So we have gamified the experience of the pre-order function, which was a lot of fun. And we've done a ton of tons of things, just mostly because we'd like to mess around, but that's just one of the things we've done so far. Alistair Croll: It's also great that Emily has like a whole team of web developers that stand up.  Emily's business is actually, she's like the SWAT team or the MI6 for some very advanced tech brands, who can't really explain what they do well. And Emily figures out how to do that. So she has a team of people to build stuff. So a good example of that is we wanted to do a survey to see whether people would take our cohort based course, which we're going to be running with Maven, the founders of  Alt MBA and UDemy,   set up this new, online cohort based course program. But we wanted to get people to take the survey. So we told them one lucky winner will get a free workshop or talk from us for their organization, which is usually something we charged a lot of money for. But we also wanted to make sure they shared the survey, which is a paradox because I want the greatest odds of winning. So I'm not going to tell my friends, right?So we made two surveys. One was Team Orange, one was Team Black. And we say, we'll choose the winner from the survey that has the most responses. That's a bit subversive. Right. And we found some funny things about people getting kind of tribal and like I'm Team Black and so on. We even did things to tweak the survey questions a little bit between the two.So we ran like six or seven social experiments in the survey. But would you buy a book from people who weren't thinking subversively? I mean, I wouldn't buy a book on subversiveness for someone who went through normal tactics. For More InformationBrian Ardinger: Absolutely. Well, I appreciate you both coming on Inside Outside Innovation to share some of this subversiveness and hopefully get more folks to be Just Evil Enough. People want to find out more about yourself or the book itself, what's the best way to do that. Emily Ross: Just Evil Enough.com and I'll actually, I landed Alistair in it on a talk we did last week because we were live Tweeting. They wouldn't let us take live questions. So we just got everyone to jump on Twitter and ask us questions there.And I promised everyone lives that if they hashtag Just Evil Enough that Alistair would read out whatever they wrote. And they all said smart, intelligent things. And I was like, I can't believe none of you are like trying to flog a course or a book or promote something. Like he will have to say anything you like. So people should...Alistair Croll: I think one guy had me mention his podcast, but there's a good example where like, Oh, you think you're getting free promotion in this thing we're recording, but you're actually following the Just Evil Enough account. Emily Ross: But yes, Just Evil Enough.com is where you can take the quiz. You can hear about the cohort class. You can, pre-order the book and there's an Evil Enough Twitter account too. You can check that out. Brian Ardinger: Well Emily, it was great to meet you for the first time here and Alistair. Always good to catch up with what's going on in your world. So appreciate you both for being on here and looking forward to the conversation in the future.Alistair Croll: Thanks so much for having us. Emily Ross: Thanks Brian.Brian Ardinger: That's it for another episode of Inside Outside Innovation. If you want to learn more about our team, our content, our services, check out InsideOutside.io or follow us on Twitter @theIOpodcast or @Ardinger. Until next time, go out and innovate.FREE INNOVATION NEWSLETTER & TOOLSGet the latest episodes of the Inside Outside Innovation podcast, in addition to thought leadership in the form of blogs, innovation resources, videos, and invitations to exclusive events. 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On this week's episode of Inside Outside Innovation, we sit down with Alistair Croll and Emily Ross, co-authors of the upcoming book Just Evil Enough. We talk about the changing role of marketing and how companies can subvert systems, undermine industry norms, and get platforms to behave in unexpected ways that tilt the scales to generate attention and demand. Let's get started.Inside Outside Innovation is the podcast to help you rethink, reset, and remix yourself and your organization. Each week, we'll bring you the latest innovators, entrepreneurs, and pioneering businesses, as well as the tools, tactics, and trends you'll need to thrive as a new innovator.Interview Transcript with Alistair Croll and Emily Ross, Co-authors of Just Evil EnoughBrian Ardinger: Welcome to another episode of Inside Outside Innovation. I'm your host, Brian Ardinger, and as always, we have some amazing guests. Today we have Alistair Croll and Emily Ross authors of the new book, Just Evil Enough, which is a book about getting noticed in this noisy environment and subversive go-to market strategies. Welcome to the show guys. Alistair Croll: Thanks for having us. Emily Ross: Thanks a million. Brian Ardinger: Well, I'm super excited to have you on this call to give our audience a little bit of a sneak preview of the upcoming book. But first let me give a little bit of background. So, Emily Ross, you are a founder of a tech marketing consultancy company called Ink Vine based in Ireland. So we appreciate you coming across the pond to give us some insights on what's going on. And Alistair and I go back a long time back in the days of Lean Startup. And he's the coauthor of Lean Analytics. We brought him back to Nebraska about six or seven years ago, I guess it was, when I was working with Nmotion to help with our startup teams in that. So thank you for both being on the show. The title of the book, Just Evil Enough. How'd  you come up with that  and what's it all about? Alistair Croll: So I'll tell you a quick story. We ran an accelerator in Montreal called Year One Labs. And one of the companies in Year One Labs was a company called Local Mind. And Local Mind was a platform for asking people questions, asking strangers questions about an area.It was later acquired by Airbnb and Lenny Rachitsky,  the CEO ran supply-side growth there. And he's now the author of one of the most prominent newsletters for startup growth marketing, Lenny's Newsletter. And in the early days they were doing what every startup does, which is building lots of stuff. But because we were very Lean Startup focused, we have them ask what the biggest risk was.And it turns out the biggest risk was that whether people would answer questions from strangers. So they ran a very quick study, which we talk about in Lean Analytics. And they found that 94% of people on Twitter would answer a question from a stranger. But this happened because I had been asking Lenny, are you being evil enough?And they were like, we're not evil. And I said, yeah, but just a little evil, because it turns out that people answer questions, but people on the platform won't ask questions. The real risk is the supply of questions. And so they actually built a system that would ask fake questions of new users. So they get in the habit of asking questions. Now you can debate the means versus the end, but what we have found ever since that time is that almost every startup that's successful has some little dirty secret in their background, where they were able to take advantage of an emerging technology or subvert the way a platform is supposed to work and turn it to their advantage.And so the basic idea behind Just Evil Enough is that almost all the time, the problem isn't whether or not you can build something it's whether anyone will care. So your job should be creating attention you can turn into profitable demand. Emily Ross: I think the subversive word is really, really important because we want to clearly differentiate between nefarious, which is downright evil and subversive, which allows you to think a little bit differently.And it's very hard for people who've been conditioned to think a certain way, to try and think differently.  So the book is about trying to teach people how to think subversively, and to show examples and frameworks in order to do that. And I remember working at a platform years ago and one of the engineers said, right, I'm going to put this button on the website to test if people will click it.And my instant reaction was, but it doesn't go anywhere. That's a terrible idea. They're going to have an awful experience and that's bad for them. And he's like, no, but I don't want to build something unless I know they're going to need it. So I'm just going to put that button there and yeah, I'm going to burn a few thousand clicks and they're gonna have a terrible experience. I don't care. I'll learn something. And he was prepared to be disagreeable in order to learn something different and to save an awful lot of time and money. And it was funny. It was like, okay. I need to think a little bit differently about how we're treating users sometimes. Alistair Croll: Yeah, we did a similar thing at Gradient. We had a reporting feature. Gradient was a startup that I launched in 2001. Eventually got acquired by BMC, their TrueSight product line. And we were about to launch reports in the product. And so we created our reports tab, and the reports tab went to a survey page. It says, we're going to do reports soon, what would you like to see?And people put in their email address and the report they'd like to see. And of course we were building a generic reporting tool. So what we did is we then generated like the top 20 requested reports. Made them defaults and then mailed those people saying we loved your feedback. Thank you so much. We've built the report you're looking for. Forget about the fact that 40 other people ask for the same report. Every one of them felt like they were a unique and special snowflake. And so we were exploiting the asymmetry between what we knew, which was 20 people asked for it and what they knew, which was, Hey, look at this, I'm special. You listened to me. And the customers loved it. Right? Is that evil? Well, it meant that we were able to build the default reports people wanted, which made the product better, but it's a little subversive. Brian Ardinger: Well, I think part of that learning is the fact that I think a lot of people think that they need to build the entire thing, because that's what shows the value. But, you know, again, you have to incrementally de-risk some of these new startup ideas. And so how do you do that with building just enough to get the learning that you need so that you can move it to the next level and build it out if you need to? Alistair Croll: Well, I would say that the problem's not minimum viable product, it's minimum viable attention.Emily Ross: Yeah. And actually, if you think about, and this is the one thing that the book, I suppose, hammers home, is that getting your go-to market strategy right, is as important, if not more important than getting your product right. Because if you can't capture attention and turn it into profitable demand, then no one's going to know about your product. And it's all about various different approaches that you can use to figure out how to do that. And  asymmetry being just one of about 10, I think that we cover. Brian Ardinger: So, is it a form of customer discovery almost so rather than the traditional customer discovery interviews there, you're looking for different ways to engage with a marketplace, engage with a customer to get that understanding of what their demand is and where they want to go from there?Emily Ross: Well, it's really interesting. Some of the examples in the book are not business examples. There's a lot of historical stuff in there, right back from Machiavelli,  all the way through to The Godfather. There's businesses, oh, tell the Genghis Khan story. I love that one. Alistair Croll: So I mean, the idea behind a lot of this is that if you know something to be true, that other people discount, you can take advantage of that. And there are many times where people knew they could do something better, but didn't Genghis Kahn, for example, knew that women could be very effective rulers. This was something that was not widely held. And so he would conquer a city, marry one of his many, many daughters off to the leader of that city. Send that leader off to war, he'd promptly get killed. Now you have a blood relative in charge of that city. Was that evil? Well, Genghis Khan did a lot of nasty things, but he did have a decent amount of respect for women's ability to run cities, which was something nobody else was factoring in. And this was an unfair advantage. Right. And I think, I mean, we're getting a little ahead of it. One of the things that Emily talks about a lot, is the idea that you need to know the norms of your system in order to subvert them. So do you want to talk a little about the water stuff? Emily? Emily Ross: Yeah so normative versus formative is like super interesting. So there's a story of by two fish and they're swimming along, and a much older fish is swimming the opposite direction. And this is from... Alistair Croll: it's a commencement address, right?Emily Ross: That's it, the older fish says, Oh how's the water? And the fish swim on a little bit and they turned to each other and go, what the hell is water? So, you have to be able to recognize the fact that you're swimming in the medium. And the best way to do that is to use external viewpoints to help recognize what you're swimming in or downing  in.I also use a log jam metaphor, which works as well. And this is a one I use all the time for teaching for problem solving, but it's really, really applicable as well too, to recognizing the difference between normative and formative. So when these to say a logs down the river, to ship them to the log yard, And they would occasionally get tangled up and a team of river pigs used to have to surround the problem really quickly because it's obviously getting worse and worse all the time, and figure out which was the one key log that you could extract to unlock the whole problem.And the only way they could do it really, really well, was through diversity of thought, opinion, and perspective. By surrounding the problem, by sharing ideas, by looking at it from lots of different perspectives. And that's why diversity in your teams, that's why diversity of perspectives is so important so that you can actually recognize what you're swimming in, whether it's water or something, a little bit stinkier. And also getting the sense of looking at it from outside, what you're used to. So ideas from different verticals, from different walks of life. That's going to help you think subversively. Alistair Croll: And that's kind of the supervillain stuff. I mean, Brian, I'll give you an example, that's a concrete example from when I came to visit you .One of your startups was making a rotary sprinkler solution.So to recap, rotary sprinklers, when they're lateral to a strong wind, get blown over and this costs a lot of money to fix. And so they built a thing that could measure the weather and the incoming winds and rotate the sprinkler downwind kind of like a wind sock, so it wouldn't fall over. And they're having a hard time selling. And what the startup revealed to me at the time when we were meeting, was that there's this weird existing system between farmers, farm subsidies, insurance, salespeople, and the makers of those sprinklers.They don't really mind when it gets knocked over because everyone makes some money and then they use that money to go on a fishing trip. If you don't know that you're in that water, all your efforts to sell are going to fail. You've got to recognize that and then go, huh? Maybe this is something I can sell through the maker of the sprinklers, or like maybe I can, you can subvert that system.Maybe you have to create an awareness campaign that farm subsidies being wasted and they could be spent on something else. But if you don't know that strategy, you can't subvert it. And that word subvert just means find another version. By definition, the hardest problems we face are the ones for which we don't have an obvious solution, because the normal approaches don't work.Which means you've got to find an unusual approach and that's normally called hacking, right? Hacking is getting something to work in a way it wasn't intended. Whether you're using a Pringle can to focus wifi signals, or you're getting a computer system to throw an error, so you can own a system. The problem with hacking is that in startups, hacking has a horrible polar reputation. Growth hacking is a bag of cheap tricks.Brian Ardinger: Talk about some of the examples in the book that maybe some people have heard of or can get a visual around. I know you've mentioned in past talks and that I've seen around this is like things like Peloton or Burger King.  Can you give examples from that? Emily Ross: I would quite like to talk about one of the ones that I had the hardest time with is about being disagreeable. And we talked about it slightly there in terms of doing things that you wouldn't necessarily think of as being quite right. But as a woman, I have been raised to be polite, to be agreeable. And actually, if you look at some of the most innovative, interesting entrepreneurs in history, quite a lot of them have been profoundly disagreeable.They've been prepared to be unliked or unloved. And this is something, a behavior that you can adopt or think about as a means to finding new ideas, or it means of finding new ways of doing things. One of the examples that we talked sports a little bit earlier, but Wilt Chamberlain was arguably one of the best basketball players of all time. He has on more than one occasion scored over a hundred points in a single game. But he had a problem. He couldn't shoot free throws to save his life. Back in college, he had a really high score, but over his career, it went down and down and down and he had a career low of like, I think 26% success rate.He was a star player. He got fouled a lot. So this was a really big problem for him. So he went to see Rick Barry. Rick Barry was the guy who could not miss. He actually had a career average of 89.3% and he got better and better as his career progressed in the last two years of his career, he had a 94% success rate from free throws. But he actually threw in a really interesting way. He threw underhand, which is actually kind of a cool word for the, Just Evil Enough book, because he shot underhand. But he was the best at shooting. But this was called the Granny Style. This is, you know, if you throw like a girl, you throw under hand. He didn't care. His father had drummed it into him from a very young age, how to shoot underhand, overhand, underhand, overhand, and he could just nail it every single time.So Chamberlain went to see Barry learned to shoot underhand and his performance doubled. He went from a career low, to a career high, in that same game where he scored a hundred points. So it turns out it's a much better approach. However, Chamberlain didn't have the guts to keep shooting underhand because he cared too much about what people thought. His career best was 61% from the line in 1961, he sank 28 of 32 free throws against the New York Knicks.So after a while, though, he reverted to shooting the way he knew, and his percentages  plunged. And he admitted that he felt like a sissy. He worried too much about what other people thought. And unlike Barry who was rational, Chamberlain was being agreeable and wrong. Barry meanwhile said he could be as selfish as he wanted to without hurting his team. So being a little bit disagreeable or asking yourself what you're prepared to do is a really good first start. Alistair Croll: Just to chime in quickly, we've all heard of growth hacking right? Growth hacking is these little tricks that get people to click a button or move down a funnel or whatever. The problem with any of these known tricks is that they're known.  Andrew Chen talks about the law of shitty click-through rates, which is simply the idea that as you find a vulnerability, if you will, a way to change the market, it becomes widely known immediately.So the first click-through ad on Hot Wired had an average of 44% click-through rate. Some people say it was as high as 70% for a banner ad. What's that at now? Emily? Brian Ardinger: Well, industry averages will tell you, or they'll tell you it's 0.1%. But in my opinion, it's closer to 0.02%, if you're lucky. Alistair Croll: So that's a huge decline. Same thing happened with email and so on. And so there are these known hacks that are the sort of marketing equivalent of a script kitty, who's running an attack on WordPress. And if you haven't patched your site, you'll be selling Viagra off your website. What you should be doing is trying to find the marketing equivalent of a zero day exploit.So in security a zero day, is an attack that nobody knows about yet. And they're incredibly valuable. Two of them were used to retard the Iranian nuclear program and damaged centrifuges. The marketing equivalent of a zero day exploit, we call this zero day marketing, is finding a new way to get a platform to behave in an unintended manner, with which you can create attention you can turn into profitable demand. And there's some amazing examples of like Farmville, for example. When Farmville's app would send you a message saying, Hey, Brian, Alistair's cows need some grain. And you'd click on it. Now you're a user. Well, they got to 30 million users before Facebook went, Whoa, we maybe don't want apps posting to people's friend feeds.There are so many examples of this, and we can tell you those examples. But the point is you can't use those examples because they've already been done. Right? What you have to do is devote much more of your time to inventing your own zero day marketing exploits. Brian Ardinger: So from that perspective, is it a series of experiments that you just have to run? You, you come up with some ideas and you run them like that, or is this, talk me through the process of how you get better at it? Emily Ross: One of the examples that I like to share, if you see it often enough, you begin to understand how you can apply the thinking. It's a model and you just try and apply it to your own environment. So if we take the information asymmetry, and example, the idea of subverting, one thing for another. Or a bait and switch. The idea of you're selling one thing, but actually getting another and Tupperware parties did this, you know, you think you're going for dinner and you end up getting guilt ridden into buying a load of plastic.But when I was working in a comparison platform, we subverted the PR channel for the generation of white hat backlinks. So PR is generally around building brand and brand awareness. But one of the side effects of PR was the generation of backlinks. So this is back in like maybe 2013. So what we did was we mined data. We attached big data trends to celebrities, pushed out, press releases to high value domains, and pretty much one in five hit would generate a backlink. When we started. We had about 1400 high quality backlinks. And we were generating about 60,000 non-brand organic visits to site per day. And after three years of pushing out two releases a month, month in, month out, we had over four and a half thousand unique domain backlinks and almost 200,000 non-brand organic visits per day.And this was a platform that turned traffic into money. I won't tell you how, but what we did for example, was we mined hair transplant trends and prices. And one example of the many, many crazy pushes we did was the Jude Law index of baldness. So here's a scale up from Colin Farrell all the way up to Dr. Evil,  of how bald are you? And you find yourself on the index and you see, Oh, this is how much it would cost for me to have hair transplants. It was a price comparison website for private health clinics. And this was a fun, interesting way to attract attention and turn it into traffic to the sites. But actually it wasn't really about traffic. It was always about the backlinks. So one in five hits generate a backlink, but again, it was channel burnout. It was a zero day exploit because you know, over the course of the three years, the number of backlinks that were being generated, went from maybe one in five to one in 10, because the platforms themselves started to recognize the value that they were accidentally giving away.So naturally you get published in a paper. If there's an online version of it, they print it online and they put a backlink out. It was a side effect of the real, a pure PR. And channel burn happened, those backlinks are no longer as readily available as they were. But it worked for about three years, four years. It was a fun time. Brian Ardinger:  You have to have a continuous funnel  yourself of new things that you need to explore it. Emily Ross: Exactly.  Exactly. So that was a, we had a good run, but it's about thinking about, well, what is the channel? What is the platform? So PR was the channel and we used it in a way. It wasn't intended to be used for our benefits. And so what are your channels? How can you use them differently? And that's a really great question to ask of yourself, no matter what you're doing. Alistair Croll: One of the things we often do is. What has changed in a technology platform. So for example, Travis Kalanick has this new startup Cloud Kitchens. What has changed in restaurants? Well, first of all, there's a huge abundance of restaurants that I could order from. Far more than I would know about. So I'm already overwhelmed with selection when I go to order food, because we're all at home, in a pandemic, ordering food. And second of all, The fact that the storefront is virtual, it means one kitchen can have many restaurant front ends. And so Cloud Kitchens will set you up with brands and their brands have games like Fucking Good Pizza, My Pasta, Dirty Little Vegan Bitch, Don't Grill My Cheese. None of these tell you about food, but when you're overwhelmed, and you have that sort of paradox of choice, you go, no, I'll just order it from that one. That sounds fine. Right? That's only possible because that brand is part of an experiment. You're ordering from an experiment. And they're constantly testing, which ones get more attention and then the restaurant can deliver all of those things that might be the same kitchen. And so Cloud Kitchens has taken advantage of an exploit within the traditional model of food ordering. So it's looking at, you know, what technology changes or combinations of technology, makes something possible that wasn't possible before that you can then subvert to your ends. Brian Ardinger: How do you go from not just creating a gimmick or how do you, I guess also approach being wrong, like trying these things and, and being wrong?Emily Ross: Growth hacking is gimmicks. Growth Hacking is doing something that maybe it's a publicity stunt or, I mean, one of the examples that we use in the book is pairing two things unexpectedly together. That's a great way to draw attention and Heineken did this really well in the UK just last week, where they put out a mobile hairdressing units and bar, so you could get a free haircut and a pint together.So this generated publicity and it's nice, but it's gimmicky, right? Is that really going to move their needle? You know, for the year? Possibly not. It's a nice story. So, but if you look at governments have been doing this for years and they've done it so well, there's a really good example in the book, which I won't go into now about how the government shamed people into stopping spitting in the twenties, as they tried to fight TB. Instead of just saying it's bad to spit, they actually made people feel bad, and socially, and vulgar  by spitting because before that it was perfectly normal.And if you look at the Chinese government, they use Fapiao.  Fapiao  are receipts. And they use Fapiao  as a lottery to fight corruption. So this is really interesting. In China, corruption can be rampant. Merchants will give their customers a discount, if the customer doesn't ask for a receipt.So the merchant doesn't have to report the income and like just pockets to the savings. The government used an incentive to combat this called Fapiao, which is a receipt  from the merchant. And there's a couple of hacks in here that are super clever. So the merchants have to buy the receipts beforehand and then hand them out to customers in return for payment.So the first one is the merchant has to pay tax before the transaction. That's really smart. And then customers demand their Fapiao, because there's a scratch and win lottery element. And then the government runs the lottery and customers can scratch off the panel to see if they've won anything. And so the second hack there is create demand for a receipt by making it a game.And then of course the government can also adjust the prize amount of each lottery to create just the right amount of incentive. So they're literally able to alter the rewards of the game to like tilt the Nash equilibrium, which is just like super smart. So you can do this at a macro level and absolutely get away with it.Alistair Croll: I want to just make sure we address your question about gimmicks. One of the big differences between a Zero Day Exploit and traditional Growth Hacking is that it's not known. But another is that it is intrinsic to your business model. The haircuts aren't intrinsic to Heineken's beer, but when Dropbox launched, they were the first to pioneer this, both of us get something. I invite you, we both get storage. That's built into the product, right. That's intrinsic to the system itself. And I think what it means is that you're factoring in Zero Day Exploits, marketing exploits, to your business model and your product roadmap. Not just to your marketing campaigns. I mean, Genghis Khan's  a good example, right?It wasn't just a tactic. It was a fundamental change in how he thought that societies could be ruled. So the real lesson here is, I'll give you one more example. There's a company that makes software called Energage  and they make workplace surveys. So they would sell to an enterprise and the enterprise would survey their employees and do  360 stuff. And so on. But the way they go to market is they launched this thing called the top workplaces project in concert with the Washington Post, the Denver Post, the Dallas Morning News and so on. And they run this survey and they say to these newspapers, Hey everybody, here's the survey. We'll take care of it.So now you go do it. And like, Whoa, isn't this great. My company is one of the best workplaces. I'll buy an ad in the newspaper. Everything's wonderful. And then Energage can go back and go, Hey, congratulations on being the third best workplace in Nebraska. Too bad about the other results. And you go what other results? Well, you know, we got more data than that, would you like to see it? Okay. And now you have a new customer, right? It's intrinsic to the business model, right. Rather than just being a little trick or hack. Brian Ardinger: That's an interesting point. And it also goes to the point where you see a lot of these examples in startups, because you can build it early on into the business model and that. How does this play out for a large existing company that wants to try to use some of these tactics?Emily Ross: So big companies really need to think about reframing and they also need to give themselves permission to think in ways they're not used to. One of the exercises I like to recommend is called a pre-mortem. And you basically give them permission to imagine the worst possible outcome. You invite them to invent the worst, worst, worst thing that could possibly happen and then work backwards from there.And it's amazing what happens in an environment like that, because that group think is real. That tribal behaviors of wanting to be agreeable and wanting everyone to pull together is very much a systematic thing that you see in large organizations. So giving them permission to think disagreeably.  Giving them methods to reframe where they are, what they do. These are all great frameworks for them to try and think subversively. Alistair Croll: First of all, I think that it's really important. I mean, I would consider a marketing department, have a Red Team. Have a second group, hmm, that has the same product and resources, but their job is to put the first group out of business. What do you do? Right. That's just hypothetical. You're going to think better. We Red Team on security. We Red Team on PR. Why don't we read team on go-to-market strategies.  And the second thing is, if you look at great brands that changed how people discussed a product or a service, they found a frame of reference that favored them. For decades we used to talk about electric cars. We would talk about sustainability and range. Pretty boring stuff, right? Lots of hippies sitting around going let's save the planet and look at my Prius. Elon Musk put one of them on a race track against supercar and beat it. And all of a sudden the conversation on electric cars was performance. He'd reframed the discussion about electric vehicles to performance, right?When Gmail first launched, your inbox on Hotmail or Yahoo mail had 10 mgs. That's like one photo, right? We don't remember that. My daughter doesn't believe this. When Gmail came along, Google knew that they did not have strength in folders and archiving and hierarchy and export, but they were good at with search and storage.So they said, Hey, email's not about your ability to manage your folders and your inbox and organization and management. It's about abundance storage. And they reinforced that so much that they actually had a counter showing you how much storage you get. Salesforce, when it first launched, was a web based CRM, but web-based CRMs had very few features compared to Siebel and Vantive and Clarify, companies that you don't see anymore.So they said no CRM is about not needing IT. In fact, their logo was no software. They had us the word software with a slash through it, despite the fact that they own their own programming language called Apex. Right? And so each of these companies found a way to reframe things, even like Listerine. Listerine was this clinical health thing. And then along comes scope and says, Hey, you know what? Mouthwash is actually about being attractive and sexy, not about clinical health. One action that a lot of big brands should take is to step back and say, what is a new frame that favors us and disadvantages our competition. And then what is it about that frame of reference that we can do to prove it that will then allow the customer to find a different way of valuing the product?Emily Ross: I would also chime in there and talk about generally large marketing teams will have, they'll have done their marketing degrees and their MBAs or masters on they'll turn out the four P's from, you know, the 1960s or the seven P's of service. And like there's too much P. Just stop peeing. Guys just stopped doing it.Right. Chuck, all of that in the bin and start thinking about creating attention. And it's as simple and as complicated as that. We talk about human motivation and Alistair  I think coined laid, made, paid, afraid. I tidy that up a bit to the piratey AARG. Which is appeal, authority, risk, and greed. So think about your customers. Think about your competitors. Think about the marketplace through the lens of human behavior and whether you're selling radiator bits or cars or Cola, people have all those very basic triggers. They want to be liked that's appeal. They want power that's authority. They want to feel safe. That's the risk lens.And then greed, you know, people want the things that they want. So. We're just human meat bags, right? We're just walking bags of meat with emotions. We have very simple motivations at the end of the day. And in a B2B setting for a big organization, the AARG framework is a really useful function. Like, so throw out the P. Think about AARG.And if you're trying to convince people to act, you need to appeal to base emotions more than you do plain reason, because most people really aren't very rational. There's also really a good examples of the seven deadly sins. If you look at the big, big enterprises, I think Chris Pack said this on Twitter.I thought it was really, really good. Uber and Amazon are slough. Instagram and Tik Tok are pride. Door Dash is gluttony. Tinder is lust. Pinterest is envy. Twitter is rath. And Bitcoin is greed. So think about the fundamentals. Just think about the basics. We haven't changed all that much. Alistair Croll: But I think the biggest thing here is that big brands haven't realized that the biggest risk they face is that someone else will subvert attention that they could otherwise be getting and turned into their profitable demand. And so if you don't do that, you're going to get eaten alive. If we can get the world to realize that the biggest risk is not whether you will build something, but whether anyone will care, we've already given people a huge headstart.Brian Ardinger: Well, and the fact that the world is changing so fast on the fact that you can go from company like Airbnb in 12 years to being, you know, one of the most recognizable brands, you know, overnight effectively from what used to be to build a business. New technologies, new marketplaces, new access to talent. All of that is just accelerating the opportunities to be disrupted. Alistair Croll: We used to have a new platform come along. You know, we had writing that took a few thousand years. Then we got to radio. It took a few hundred years. And then we got to television that took a decade, the rate of introduction of new platforms. And therefore, if you're thinking like a hacker new attack surfaces, Is incredible, right? The Cloud Kitchens example happened because of the pandemic and the rise of Uber Eats and Door Dash, and so on. The pace at which new exploit opportunities appear is very, very fast. And as a result, there are far more opportunities to subvert the status quo or the norms of your industry with one of these new platforms.So we're trying to get people to be much more opportunistic. And part of what we do, like I said I can't tell you do this thing, because if I tell you, then it's already been done. What we can do is we can say, here are some ways to think about it. You know, is there an innovation that happens? Can you reframe things? Can you do a substitution where people think they're getting one thing and they're actually getting another. Can you appeal to the foibles of human psychology? Emily Ross: Don't be afraid to be disagreeable. Alistair Croll: It's weird because in the past I've written books that are very technical. There is a right answer. And Emily's written lots of articles on like how to do stuff. This is a more subjective thing and candidly more uncomfortable for us as writers, because we want to make sure that there are applicable lessons, but it's almost like, you know, teaching someone Zen. I can tell you what it is, but you're going to have to go sit on a rock and figure it out for yourself.But once you start thinking this way, everything becomes a subversive opportunity. And once you have that subversive lens, you're not being evil, you're just being just evil enough. Opportunities are everywhere. Emily Ross: And actually, if you think about it, just coming back to your very first question, which is a nice cyclicity.  The title of the book is exactly what we set out to do, which is we got your attention and we're turning it into demand. So the book title is a really, really simple and effective way to showcase the thinking. And I think if you take one thing away from it, it's change what you spend your time on. So building a subversive go-to market strategy is just as important as thinking about your product. And if you get the balance, right, you're going to be unstoppable. Brian Ardinger: Well, and you've also from the book perspective, the book's not out yet, but you're doing things to grab attention differently than a lot of, I mean, I get pitched every other day by a book author trying to get their book noticed and that. But I know that you've been doing some things as far as live online course that's leading up to the book. And you have a interesting little survey. I don't, if we got to talking about any of the things that you're doing from a attention perspective to, about the book. Emily Ross: Well one of the things I love, this was so much fun, is that you can't just order the book. You can't just pre-order it. You have to take a quiz so that we can decide if you're evil enough. So you take the quiz and if you're not evil enough, we think, you know, you're not going to be able to handle the book. And if you're too evil, then this book could just perhaps be too powerful. So we have gamified the experience of the pre-order function, which was a lot of fun. And we've done a ton of tons of things, just mostly because we'd like to mess around, but that's just one of the things we've done so far. Alistair Croll: It's also great that Emily has like a whole team of web developers that stand up.  Emily's business is actually, she's like the SWAT team or the MI6 for some very advanced tech brands, who can't really explain what they do well. And Emily figures out how to do that. So she has a team of people to build stuff. So a good example of that is we wanted to do a survey to see whether people would take our cohort based course, which we're going to be running with Maven, the founders of  Alt MBA and UDemy,   set up this new, online cohort based course program. But we wanted to get people to take the survey. So we told them one lucky winner will get a free workshop or talk from us for their organization, which is usually something we charged a lot of money for. But we also wanted to make sure they shared the survey, which is a paradox because I want the greatest odds of winning. So I'm not going to tell my friends, right?So we made two surveys. One was Team Orange, one was Team Black. And we say, we'll choose the winner from the survey that has the most responses. That's a bit subversive. Right. And we found some funny things about people getting kind of tribal and like I'm Team Black and so on. We even did things to tweak the survey questions a little bit between the two.So we ran like six or seven social experiments in the survey. But would you buy a book from people who weren't thinking subversively? I mean, I wouldn't buy a book on subversiveness for someone who went through normal tactics. For More InformationBrian Ardinger: Absolutely. Well, I appreciate you both coming on Inside Outside Innovation to share some of this subversiveness and hopefully get more folks to be Just Evil Enough. People want to find out more about yourself or the book itself, what's the best way to do that. Emily Ross: Just Evil Enough.com and I'll actually, I landed Alistair in it on a talk we did last week because we were live Tweeting. They wouldn't let us take live questions. So we just got everyone to jump on Twitter and ask us questions there.And I promised everyone lives that if they hashtag Just Evil Enough that Alistair would read out whatever they wrote. And they all said smart, intelligent things. And I was like, I can't believe none of you are like trying to flog a course or a book or promote something. Like he will have to say anything you like. So people should...Alistair Croll: I think one guy had me mention his podcast, but there's a good example where like, Oh, you think you're getting free promotion in this thing we're recording, but you're actually following the Just Evil Enough account. Emily Ross: But yes, Just Evil Enough.com is where you can take the quiz. You can hear about the cohort class. You can, pre-order the book and there's an Evil Enough Twitter account too. You can check that out. Brian Ardinger: Well Emily, it was great to meet you for the first time here and Alistair. Always good to catch up with what's going on in your world. So appreciate you both for being on here and looking forward to the conversation in the future.Alistair Croll: Thanks so much for having us. Emily Ross: Thanks Brian.Brian Ardinger: That's it for another episode of Inside Outside Innovation. If you want to learn more about our team, our content, our services, check out InsideOutside.io or follow us on Twitter @theIOpodcast or @Ardinger. Until next time, go out and innovate.FREE INNOVATION NEWSLETTER & TOOLSGet the latest episodes of the Inside Outside Innovation podcast, in addition to thought leadership in the form of blogs, innovation resources, videos, and invitations to exclusive events. 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Lenny writes the #1 business newsletter on Substack (Lenny's Newsletter) and previously sold his company, Localmind, to Airbnb. He then spent 7yrs at Airbnb leading product + growth teams and now angel invests + works as a full-time creator. Watch + subscribe on YouTube: https://youtu.be/aogsYWWnq60 Get every episode + giveaways sent to your inbox: https://www.creatorlab.fm/subscribe/ Let us know what you think on Twitter: https://twitter.com/bzaidi​ https://twitter.com/lennysan In this conversation you'll learn about: – the racecar growth framework: growth engines, turbo boosts, lubricants + fuel – core growth engines: performance marketing, virality, content + sales – examples from Airbnb, Zapier, Superhuman, Wish, Casper + others – benchmarks for user retention + types of virality  – 3 steps to getting early users – growing a newsletter + the differences in approach for creators vs companies   Timestamps: 0:00:00 - Snippet + What We Cover 0:01:28 - Sponsor Break 0:02:17 - Lenny Intro + Background 0:07:38 - Scale of Newsletter 0:09:17 - Questions To Ask Yourself When Figuring Out Your Next Step 0:12:18 - Energy + The Struggle Of The Content Treadmill 0:13:31 - Early Days Of Airbnb 0:15:09 - Creating Something Remarkable 0:17:22 - Racecar Growth Framework - Who Is This For? 0:18:20 - Early vs Late Stage Growth 0:19:48 - Engine, Turbo Boosts, Lubricants + Fuel 0:20:05 - Growth Engines - virality, performance marketing, content, sales + bonus examples 0:24:11 - “1st time founders focus on product, 2nd time founders focus on distribution” 0:28:09 - Becoming The Best In The World At 1 or 2 0:28:38 - Airbnb vs Booking 0:29:16 - Performance Marketing 0:30:51 - Wish + Casper - Built On Performance Marketing 0:31:42 - Feasibility When Bootstrapping 0:32:31 - If You Should Be Performance Marketing Driven: 1) Generating Revenue From Users 2) Not Something Users Are Looking For 0:34:01 - Growth vs Brand Marketing 0:35:37 - When To Expand To The Next Engine + S Curve 0:36:56 - Examples Of Virality - Word-of-mouth, referrals, inviting friends, etc 0:40:22 - Bottoms Up vs Top Down Virality 0:41:31 - Knowing When You’re Going Viral - K Factor vs % of people who came in thru referral 0:42:33 - % Benchmark To Aim For 0:43:24 - Companies Who Are Suited To Viral Growth 0:43:48 - Clubhouse + FOMO 0:45:17 - User Generated Content Loop 0:47:29 - Data Driven SEO - Zapier + Thumbtack 0:49:11 - Editorial SEO + Figuring Out Content Strategy 0:50:31 - Superhuman Example 0:51:13 - Desired Outcomes, Primary + Secondary KPIs 0:52:43 - Sales Channel 0:55:19 - Turbo Boosts + Lubricants 0:56:52 - Power Of Events 0:58:37 - Retention + Conversion 1:00:41 - Activation: Using Product For Its Core Purpose 1:02:03 - Superhuman , Creators + The Customers Who Care 1:05:38 - User Retention Benchmarks 1:07:44 - Common Pitfalls 1:09:36 - Getting First 1000 newsletter subscribers 1:11:20 - 3 steps to getting early users 1:14:45 - Creators vs Companies - Finding Core Users 1:19:27 - Would You Still Be Doing This With 1000 Subs? 1:20:55 - 5 “Jobs To Be Done” Of Content 1:21:49 - Newsletter Discoverability 1:23:42 - What Gives You Energy 1:25:23 - Airbnb Job vs Creator Life 1:26:22 - Tim Urban on Content That Spreads 1:27:18 - Creators: Value vs Support 1:29:22 - Decision To Stay On Substack 1:31:31 - Knowing What To Write About 1:35:57 - Longer-Term Plan   Thank you to our sponsors: AppSump - the marketplace entrepreneurs trust to buy and sell the products that grow small businesses into name brands: https://www.appsumo.com Space - the easiest way to engage your team over audio: http://www.JoinSpace.co  

Venture capitalist Li Jin left Andreessen Horowitz to start her own firm, Atelier Ventures. She started Atelier to fund a specific vision of the world: a world in which people are able to do what they love for a living and to have a more fulfilling and purposeful life.In addition to being an investor, Li is a prolific writer and podcaster, producing not only a newsletter but also writing articles for major publications.Find out whether you should really be writing content every week, or whether your effort is better spent on longer-form, epic articles. Should you be publishing in your newsletter, or in publications like Harvard Business Review?Li and Nathan don't just talk about content, they also get deep into business models for your newsletter business, with Li sharing her perspective as the founder of a venture fund. Don't miss Li's unique combination of deep investment knowledge and artistic creativity!Links & Resources Andreessen Horowitz - Software Is Eating the World LiveJournal: Discover global communities of bloggers who share your unique passions and interests. Myspace Zynga The Nathan Barry Show 028: Packy McCormick – How Much Are 30,000 Subscribers Worth? Evernote Harvard Business Review - Ideas and Advice for Leaders The Nathan Barry Show 023: Tiago Forte – Building a Second Brain & Lessons From a $1M/yr Newsletter The Nathan Barry Show 017: David Perell – Mastering Twitter to Grow Your Newsletter and Make Money Li Jin's Links Newsletter: Li's Newsletter Website: Atelier Ventures Podcast: Means of Creation Twitter: @ljin18 LinkedIn: Li Jin Episode TranscriptLi Jin: [00:00:00] What are your goals and what is the content that you're creating and why are people subscribed and reading it? The business model needs to fit what your content is, who the audience is, who the creator is, what the platform is. All of those things need to be aligned. Direct user monetization is totally in vogue in the form of donations, ad hoc payments, subscription payments.It's always charging the user for something. Nathan: [00:00:28] Today's episode is with venture capitalist Li Jin. So Li was at Andreessen Horowitz, and then she recently left to start her own firm, Atelier Ventures. We talked about a lot of things that I find interesting, like business models for your newsletter, for example, should you monetize through a paid newsletter sponsorships or what she does through running a venture fund?We get into whether you should write content, you know, consistently every week, or should you publish it once a quarter and put out these incredible long form posts we get into writing about, or excuse me, writing for publications like Harvard Business Review versus your own newsletter. There's so much good stuff in here.So I'll just get out of the way and we'll dive right in.Li, welcome to the show.Li Jin: [00:01:14] Thank you. Thanks so much for having me, Nathan.Nathan: [00:01:17] Okay. So I want to dive in and just immediately talk about revenue models, all of that, because you have this tweet that I just loved, that it was like dying, laughing when I saw it. And the gist of it is I have a paid newsletter. It's my monthly LP update. You were talking about how either those business models is everything else.And I imagine saying like me, why don't you launch a paid newsletter? So could you talk through how you think about, you know, your business and what you meant with that week?Li Jin: [00:01:50] Yes. So I joke that my LP update, which I send out quarterly as a email is basically my paid newsletter. And I think it's, it's basically a riff on the joke that we used to make about a16z, which is the firm that I used to work at the VC firm that I used to work at. We used to joke that it was a media company that monetized through venture capital because a 16, Z as a firm is so prolific in creating content.They have a podcast, actually, a network of podcasts, the blog. they have a series of different clubhouse shows now as well. they just do a ton of different media and content creation activities. And so people used to joke like, Oh, this is actually a media company that happens to monetize through venture capital.And I think of myself now as kind of a miniature version of that, where I'm a solo. Content creator. and I monetize through venture capital. Like that is my revenue model. I have a venture capital fund that I raised last year, called . And that is, you know, my day job. That's where I spend the majority of my time.And then the content that I put out into the world, It's free. It's, it's mostly free for founders to consume. It's really designed to help them build companies, and to guide them and their strategies. And I don't monetize the content at all. And the way that I monetize the content is through investing in the best companies that come as a result of the content creation.So, yeah, that was, that was the Genesis behind, the tweet. And so the LV newsletter, I mean, the LPs are like the investors in the fund and that's how I monetize it.Nathan: [00:03:33] Yep. That makes sense. And I think once you have this attention, Then there's so many ways that you can monetize it. I was talking with Trey, remember who wasn't a past episode. we were talking about how people have alluded to Nike being like they're just an ad agency who happens to realize that the best model to monetize is through, you know, shoe and apparel sales, but really their core strength is advertising and marketing.And so I think there's plenty of examples of people who have, like, the. Have this audience and then an unconventional way of earning a living.Li Jin: [00:04:09] Yeah, precisely. And I think to build on that. Like there's a lot of examples of newsletter writers who do a similar thing where they're operating a syndicate. Like I think Packy who you've had on the show has a syndicate that he invests in deals through. there's other newsletter writers. I know that angel and fast Lenny Rachitsky is a very active angel investor too.So yeah, a lot of them are sort of blending different business models because newsletters are such a great vehicle to, to build an audience. To get reader attention, to communicate your thoughts into the world and kind of mind-meld with a lot of really interesting folks. And then the best way to monetize that might not be through a straight up subscription or pay.Well, it might be having upside in the businesses that they built. and I think. Content creators are having that realization too in the broader content creation ecosystem beyond just newsletters. So now I'm seeing content creators from the Tech-Talk Instagram, YouTube worlds, getting into investing angel, investing into startups, because that is a way that they can monetize the brands and the attention that they've built and also diversify themselves beyond just being a single content creator.Nathan: [00:05:28] Yeah. I mean, it's, it's wild when you see it. Like, I think. You know, a lot of people in the, the acting movie world have, are doing it now, but like Ashton Kutcher was pretty early with startup investing and, you know, he's taking this money and fame and attention that he has and putting it into to startups.And you know, now it feels like everyone's got, you know, some sort of started that they're involved in or a liquor brand or something else where they're basically saying, saying like, yes, in addition to. Getting paid millions of dollars to show up in this movie or to sponsor this brand on TED talk or, you know, like do a sponsored spot for the brand new talk.You know, why don't I have equity? And I'm curious where you see that going. Do you think that trend is just going to continue?Li Jin: [00:06:15] Yeah, I think in any crowded market with a plethora of different options that folks can choose from brand is going to matter brand as a differentiator matters. and so. Like venture capital is no different from that. There's so much capital available right now for founders. Founders probably get like a ton of inbound offers to give them capital.And so founders are now in a position of being able to choose, like who do I actually want to accept capital from? and I think I first heard this from first round capital. one of the partners there said like something like. venture capital is a product that you buy with your company's equity.And so yes, as a founder, you're choosing which product to buy with your equity, your equity is worth something you can purchase like a venture capital investor to work with through that equity. And so, the implication for VCs is like, how do I, how do we make our product the most attractive product and how do we distinguish ourselves and be the, the venture capital provider of choice for founders. And this was actually one of the driving factors behind me announcing my fund a couple of weeks ago on product hunt was tapping into this ethos of actually investors are products. We are building products. We have to provide differentiated value to founders just as they are trying to build differentiated startups, to compete in a crowded landscape of different software.So I think content creators, getting into investing is just another it's emblematic of this. It's like, how do, how do we differentiate our capital from all the other capital that's available out there? And especially in the consumer world when consumer attention is now so scarce and spread so thin across so many different options, having.Captive consumer attention and having distribution into consumers, it's such a huge leg-up for any consumer company and content creators represent that they represent so much built-in distribution power into, tons of different consumers. And so I hear from founders all the time, like they want to bring in content creators into the round, and they sometimes have specific criteria of like content creators who have a big following among, you know, Gen Z on TikTok or, um, moms on TikTok if they're selling some sort of children's education products.So they're identifying like who are the end consumers I'm trying to reach and what are the con who are the content creators that can help me reach those, those people.Nathan: [00:08:58] And are they in those cases they're taking, It's not a straight advisor deal in that case. Right. It's there, it's still taking investment from the influencer or from the fine and then saying, but really the money is just the table stakes. Now it's like to differentiate, what else are you going to provide as far as access to the audience or whatever else is that right?Li Jin: [00:09:21] Yeah, the way that it's structured is, it, it, there's no like, one single way that it's structured. It can be sometimes just an advisory agreement, that we're all used to, or it could be a combination of advisory. Plus like investment to the company and with dollars. or sometimes it's just, you know, a normal equity investment into the company.I think founders usually for, that the Creek is an investor into the business because then they have more skin in the game. but you're right. That like, it's more about having access to their distribution and their brand than the actual dollar amount itself.Nathan: [00:10:01] That makes sense. Were you always thinking about, like as you left a16z starting your own fund, or as you started a new newsletter and all of those things, did you pursue kind of all that rate, like the whole range of options for how you could monetize.Li Jin: [00:10:16] the, the plan was always to start a fund. So I knew that going in. I mean, again, I guess, going out that was always the plan and, Aye. But in tandem to that, I also kept creating content, which was an activity that I had been doing when I was at a16z. And even before, like I I've always been very active in writing online and writing publicly.A lot of people don't know this, but I kept a food blog throughout college, where I would Chronicle like all of the meals and things that I would cook. and before that I was blogging about like my everyday life. Very boring, in high school and in middle school. So I've always been a very prolific writer.And so, as I've been on this journey of, building my own fund and, and getting started investing, I've just continued to create content and primarily written content because that is the format that I feel most comfortable in.Nathan: [00:11:23] Yeah, that makes sense. I think a lot of people, you know, you have this like overnight success type of story, and then you dig back and it's like, yes, but I've been creating content consistently for. I don't know, a decade or two.Li Jin: [00:11:39] Yeah, I I've been writing Daily. Like I first started writing Daily. I remember this moment. Very clearly. I moved to the US when I was six years old from Beijing. And before that, I didn't know English. So I learned English in first grade through ESL classes, and I happened to win a diary, a physical diary.It was a Lisa Frank diary, like multicolored, rainbows, plus dolphins on the cover. I won that at an afterschool bingo game in the first grade at the same time that I was learning English. And I started writing in this diary every single day. as a six year old and throughout my childhood, I just went through so many different physical diaries, like I wrote consistently every day and then the internet happened and I went onto the blogging platforms.But yeah, writing has like been a consistent daily habit for over 20 years.Nathan: [00:12:38] Yeah, that's wild. What was the first blogging platform that you went on to was that LiveJournal or my space?Li Jin: [00:12:43] I think it was Zynga.Nathan: [00:12:45] Yeah, I didn't, I published on LiveJournal, butLi Jin: [00:12:49] I was on LiveJournal to you. LiveJournal was great. LiveJournal was what I used in high school. It was where all the cool kids were.Nathan: [00:12:56] yeah. I'm trying to think what happened to LiveJournal. I actually hadn't thought about LiveJournal before this moment. Didn't.Li Jin: [00:13:03] I, you know, I tried to dig up my old LiveJournal and all of my old things, and I think it's been deleted like after some period of inactivity, I think they just deleted everything. So it can't find it so that like, it represents years of memories, which I'm quite sad about. So I think there's still value in keeping a physical diary.If you want to remember your life.Nathan: [00:13:27] I think there's things that on one hand like that I've published on LiveJournal that I would love to have. But I'm also very thankful that the broader internet isLi Jin: [00:13:37] Right. Yes. It, it was very like it's, it's doc's proof basically because they deleted everything on our behalf.Nathan: [00:13:45] Well, maybe taking a step back. I think there's a lot of people who have built a newsletter in are trying to decide. The best way to monetize it. and haven't thought about investing, or maybe they're thinking about like, Oh, maybe they like me right now. Right? Because of my Content, I get asked to invest in a few things.And so I do a little bit of angel investing, but I'm curious what advice you have for someone who is now going, Oh, I have 10, 20, 30,000 people on an email list. they're starting to be this deal flow. You know, is starting a syndicate or maybe even becoming a full-time investor of direction with resilience.Li Jin: [00:14:32] so I think you really have to consider, like, what are, what are your goals and what is the content that you're creating and why are people subscribed and reading it? Like, I think the business model needs to fit all of those things. So I talk about the concept of like, business model fit, like the business model needs to fit, like what your content is, who the audience is, who the creator is, what the platform is, all of those things need to be aligned.So I think right now is a moment in which like, Direct user monetization is totally in vogue and every platform is introducing new direct user monetization features, typically in the form of like donations, ad hoc payments, subscription payments. but it's always charging the user for something. And I, I actually don't think that that fits every writer.There are actually lots of different business models that you could play with and experiment depending on who your audience is and what the content type is. like I think Packy is very successful doing sponsorships and like if he moved to subscriptions like that would block access for a lot of people that he's able to reach.Right now through sponsorships. I think there can even be like new business models that get invented that we haven't even seen yet. That could be really well aligned with writers. so for instance, there's a platform called mirror, mirror.xyz. Is the name like a reflection mirror. and it's a crypto blogging platform.So they're built on crypto rails and you, so you can program all sorts of different new business models that previously hadn't existed. So recently there was a really interesting experiment that a blogger, named John Palmer ran where he actually crowdfunded his, his essay, his upcoming essay. And so, people were able to.Place bids and crowdfund his essay. And he ended up raising $13,000, but the people who were crowdfunding it didn't just do it. So out of altruism, they did. So in exchange for tokens that they could then trade and that represented ownership in the essay itself. Which is really interesting. so that's like a new business model that gets unlocked by crypto, which previously hadn't existed.So, so I'm interested to see more of these experiments happen in the future that aren't, you know, one size fits all because I think the subscription business model is really great for writers who are writing consistently, who are delivering consistent kind of constant value to their audience, but it doesn't work for everyone.Nathan: [00:17:11] Yeah, that that makes sense. And like, in this case, if you were to. Not publish for a few weeks. That would be entirely. That would be totally fine because your business model isn't dependent on that extent or like continuous value.Li Jin: [00:17:24] Exactly. Yeah. I think the issue right now is like, For writers who write a really high quality piece, maybe two or three times a year. There's no good viable way for them to monetize that. Like, they can't really justify a subscription. Maybe they couldn't collect donations, but like that just depends on people feeling very generous and charitable.And so the only good way to monetize that kind of cadence of writing right now is like through investing, I think, through being a venture investor, But yeah, like I think that type of writing also deserves a good business model.Nathan: [00:18:03] Makes sense. I think the biggest point for someone listening in is that there's the business models that you see at face value of like sponsorships, or, you know, paid subscription access probably are the two most common. And then it's also like, and there's so many more possibilities and I'm always the most fascinated by the businesses where you're like, wait, I know they make money, but how do they make money?And when you really think about it often there's some other, you know, side thing, like for example, I know the people over at link fire and they provide these like little landing pages when for artists, you know, so Taylor Swift comes out with her new single here's a single page that has all of the links right.To. iTunes, Spotify, et cetera. You know, they're used by all the major labels and you go to their site and they make money through subscriptions. You've paid 15, $20 a month to use their service, but they actually make a lot of money through the affiliate revenue from iTunes and Spotify, and for all that for driving the traffic.And so, you know, just really encouraging people to dig under the surface a little bit and, and at least consider some of the less obvious business models.Li Jin: [00:19:15] Yeah, absolutely.Nathan: [00:19:19] I think that, well, I want to shift gears a little bit. There's, an article that you wrote, titled the creator economy needs a middle-class I'm curious one, let's start on the research side. That is like a, a there's like quick blog posts that you can write. You know, you have an idea, you write it out, you fire it off.And sometimes they really resonate. Other times they don't, And, you know, maybe it's like three hours or five or 10 hours that goes into that. this post is the opposite of that. And I'm curious, what is your research process look like? How do you go about writing a substantial piece like that?Li Jin: [00:19:56] Yeah, I would definitely say like, all of the writing that I have published is not of that sort it's of the like a hundred hours went into this, or like, that's why I only published like four times a year. it's because I work on each piece for like two, three months. So, yeah, a lot of research goes into these things.There's a lot of time I speak to a ton of people. I have a ton of people read them, critique them, offer different angles and perspectives. and so, yeah, I, it takes a really long time. It's like writing a thesis in school. how this one came together was. So I had written a piece like a year and a half ago called the passion economy and the future of work when I was still working at Andreessen Horowitz.It's a blog post that was. I think pretty widely read and a lot of founders, were really positive about it. But one of the critiques that I got in the aftermath of the publishing that piece was, this is great. And like so optimistic and like very positive. And we really want to have this come true, but it feels like, it feels like this is only a viable, viable path for so few people like.There's only so few people who can even make a living this way and who can participate and be successful in the passion economy. like, is this too optimistic? Was there feedback? And that question has been like in my mind ever since then, like, because as an investor, I want to back things that touch millions of people like that can, you know, transform society and how we work, not just enable a thousand people or 10,000 people in order.To to monetize. so I've always been really interested in like, how do we actually unlock the ability for many, many more people, like tens of millions, hundreds of millions, of people to be able to participate in the passionate economy and to be able to do what they love for a living. So the piece was inspired by that.And, in order to write this, I had to go very broad initially and like study, how did the middle-class come about in the real world? Like I looked at. The history of this country and like how, we got started in the trends around inequality in the middle class, in all developing countries and, and.Developed countries, Europe, the US et cetera. I looked at like policies. I researched specific policies that we had passed in order to encourage the growth of the middle class. And that contributed to like rising wages in the middle of the 20th century. I looked at unionization, deregulation, the trends like since the 1970s and the shareholder revolution, like so much research went into this.And it was very like concisely summarized in the end piece and piece really focused on the crater economy. And how does the crater economy, support and middle, but yeah, there was, there was a ton of background research that went into it and it was informed by stuff in the broader world as well.Nathan: [00:23:09] Lot of questions about that, the first one is what's the reason. That you take the approach of say like for flagship pieces of content a year versus maybe some of the more traditional advice of like publish super consistently, you know, every Monday at 10:00 AM or something like that.Li Jin: [00:23:28] I mean, I kind of do that because I use Twitter. And so Twitter is like my kind of ongoing, I Write tweet storms. And like, these are just my quick thoughts. It's nothing like super groundbreaking, but it's like interesting and thought provoking. And like, I'll just publish that on Twitter. for my long form pieces.I don't know, that's just kind of the bar that I hold myself to. And like, I think things are more evergreen when they go really deep and when they are extremely cohesive and pull in so many different strings and like just give rise to so many more questions and lines of thinking. and that's the type of style that I think.I, I prefer to write in, and I feel good about my content when I publish it. there's a lot of like stuff that I don't publish that never sees the light of day. That is perhaps of the sort that like I could quickly publish if I wanted to be more frequent in my writing. But I just don't think that they're groundbreaking enough.Like my bar is kind of like, does this get people to see the world in a completely different way? You can't do that so often, like it's hard to do that regularly, every single all week. but that's kind of just the bar that I've given myself as a writer, because I want my pieces to have longevity. I want it to be like, every time I'm in someone's inbox, they feel like they must like clear their calendar and feed this thing.And in order to. Maintain that relationship with my audience. Everything has to be really good.Nathan: [00:25:06] Yeah. I definitely, I have a few pieces that I've written that. Are sort of that those flagship pieces of content, like for me, it'd be the ladders of wealth creation and then the billion dollar creator where, you know, they really, they come together over a long period of time. It's usually like it started 18 months ago with a conversation with a friend that kind of sparked something and then it sort of iterates from there.But I can't get any consistency towards those ideas, you know, it's definitely when they come in and they, you know, I shaped them for a long time. So I'm curious. Do you maintain a list of like these ideas that might turn into something or what's, what's sort of the notes process on that side?Li Jin: [00:25:50] I do the notes process is really disorganized. So it exists like in my brain, I have a list in my brain of things that I'd like to write. Sometimes that list gets dumped into Evernote, but not really consistently. sometimes I'll think of something like really late at night when I'm not in front of my computer.I'll just like, jot it down in my phone or like text myself. so the ideas are kind of scattered around, but they're there, they're there somewhere. And. Sometimes I catalyzed by either like an external thing or something internal that I read. and that just inspires me so much. I feel like, okay, now is the time to take that idea into like, actually.Build a piece around it and, and, and write it out, that there's like way more ideas that I have that never turned into one of those flagship pieces and only a small percentage of them actually get written out. I actually think like for everyone, who's saying like there's too much writing in the world, like there's too many newsletters.I actually think there's like way more ideas that should be written out that currently aren't just because writers don't really have the time to do it.Nathan: [00:27:02] What I love that of the. The bar that you're setting for one of these flagship pieces being like you should finish reading it and your worldview should be different, or you should at least have all of these questions about your current worldview.Li Jin: [00:27:15] Yeah, it changes someone's life.Nathan: [00:27:24] What do you think about, you know, where are you published these pieces? Right. Because a lot of people would say has to be on my site. I need the, The search rankings, the backlinks and all of that. And you're going like, no, I'm going to publish it on the Harvard Business Review.Li Jin: [00:27:41] Yeah. I, I, I've been sort of like, I've evolved in my thinking around this. well, so firstly, like when I was still working at Andreessen, everything had to go on their blog. So, I published on their blog and so a lot of my older pieces are still at dot com. since then I've been utilizing my own newsletter, my Substack newsletter as mine primary channel. and I like that because I think the ethos of having like access to your readership and being able to reach them directly without any sort of intermediary, I think that's great. especially since like the way that I typically reach people is through Twitter and through this algorithm, like that feels a little shaky and unsteady.And so if I can collect people's emails, that's awesome. and then. HBR HBR came about in like the most random of ways, honestly. I hadn't been intending to publish it at HBR. I was intending to just go through my newsletter as normal. And then at the last minute, basically when the piece was already done, I sent it to an HBR editor that I knew, and I was like, Hey, what do you think of this?And, and his response was, this is great. I would love to publish it. So can you hold your newsletter? and, and I, I basically, I was like, okay, like, let's test this out. Cause I think HBR, like HBR is one of those publications that I would be willing to bend on my, like, Collect user emails rule. Like they have huge distribution, they have way more page views than my newsletter gets.And so I thought it was, it was a worthwhile experiment to run. And so, yeah, I gave them that piece. I also publish it in my newsletter that same day as well. but I I've been driving traffic to the HBR version and, you know, the response to, to that has been so interesting, because. When people read the piece in HBR, I think they just immediately viewed it as more legitimate than when I published in my own newsletter.People were like, Yeah. People were like, Oh, this piece must be so good. It's an HBR. And I was like, have you read any of my past writing? Are you saying it's not good? Like, cause it's, it's the same bar as I always have had for myself. It's just that this one happened to get picked up by HBR. It's like, my, all of my writing is like best, but like for some reason, because it's an HBR, I think a lot of people just viewed it differently, which has been absolutely fascinating.And it kind of throws a wrench in the whole creator economy, narrative, right? Because we're all about institutions over individuals and how like a personal brand is so much more powerful than like an institutional brand. But I firsthand experience that when I'm affiliated with this like powerful institution of Harvard Business Review people to take me more seriously, or at least there is a segment of people who took me more seriously.Nathan: [00:30:47] Well, I think it's what you're talking. I think about brand being the most important thing. And, you know, HBR has this brand, you even, you walked through the airport and it's like, HBR has top reads all of this stuff. And so we know that the content is going to be really high quality and, and the packaging does matter, right?The packaging of the being an HBR versus, being on your blog or a newsletter Substack, like. And you're just immediately in that of that caliber. And so it's interesting. I'm curious if you think more authors are going to be pushing them to publish their content, you know, there, the Atlantic, you know, some of these other like publications that sort of have an increased amount of credibilityLi Jin: [00:31:32] I think they should. I think they should. Just as we kind of diversify our different revenue, streams and business models as creators, I think we should also diversify where we publish content. in order to expand our reach. It's, it's sort of like the idea of, Content collabs that we do with other creators.Like how do we leverage each other's audiences in order to grow? I think, writers can accomplish the same by. Distributing elsewhere and tapping into an established publications audience. so I think if there is a publication that writers really admire that they think. Could be, harnessed for audience growth, where that publication probably has a large base of users who would also be interested in your writing.I think it's definitely worthwhile to do that. I don't think it needs to be done constantly and like exclusively. I don't really believe in doing anything like all like the same all the time. but I think here and there, like writers can choose to leverage other platforms for growth.Nathan: [00:32:42] What were some of the results that you got from it? Was there anything unexpected or, Li Jin: [00:32:46] So the one unexpected thing was like people who I thought already really liked my writing were like, wow, this is so good. Like.That was one thing. like my brand, although I thought it was like already a legitimate, it was clearly not as legit as HBR's Franz. I, yeah, I did get incremental new subscribers from it because my, my publication was linked at the bottom. I think it also, it, it was an interesting experiment for them.Cause I think their reader base is not as Silicon Valley centric as probably our information diet. Like we are reading all these blogs and like all of these sub stocks constantly and thinking about like the creator economy, I think a lot of their readers probably saw it and thought like, what is a creator?Like what is, what is the CR what is the greater economy? so I'm not entirely sure if like, My target audience mapped to theirs. there were definitely some comments of like, this is so abstract and like out there, and like first we need to define what a creator is. so that was really interesting.Cause I think. I think HBR is one of those publications that has such a broad reach across the planet. Like there's middle managers in Europe and in the middle East who are reading HBR and might not be as like deep in this particular particular topic. Whereas our motion as newsletter writers is to go really deep and to be really aligned with this particular niche and not write for the public audience, but to write for like our specific single target audience.So going to, A more general readership target, targeted publication. it kind of taught me that I am kind of like inhabiting this little bubble.Nathan: [00:34:44] Well, one thing I was just thinking about is that you kind of have two different, demographics that you're serving right. On one hand, you have the, the companies that you want to invest in, right? So if they're reading your newsletter and someone's thinking about, okay, I'm ready to raise then.They're already a fan of you. And so your, your capital to come in has a significant advantage over any other VC fund, but then you have the other side of, you need to go raise from LPs. And so I'm wondering if being in a place like the Harvard Business Review or something else, or other places you might put your Content might actually help attract, new LPs.Li Jin: [00:35:24] What's really interesting is that I've found that to not be true, like LPs don't go on Twitter by and large, and they don't read some stock newsletters that are written by practitioners by and large. And so. It was, it was really interesting, honestly, in a ton of my conversations with traditional LPs, they didn't know where to create our whys.They didn't know what the passionate economy was. They like never visited, you know, the blog, the a16z blog, like all of these concepts they had never heard of. And like, they. Never saw my Twitter. Like they, they might not even have a Twitter account. and so they're, they're kind of like inhabiting their own ecosystem and I'm not entirely sure, like what I need to write or like what topics I need to cover to reach them.I would say like among founders, like the stuff that I write does have an audience and like is widely read, but the LP stuff, like the Content has given me no advance.Nathan: [00:36:25] That's interesting. Cause like I have this ideal that maybe it would give an advantage, butLi Jin: [00:36:32] I would love that, but that's not the case.Nathan: [00:36:36] And raised from LPs, is it, you know, just a lot of introductions and meetings and that's the whole thing,Li Jin: [00:36:43] It's a lot of relationships, introductions, warm instructions, getting your LPs to introduce each more LPs. It's such a, yeah, it's a really fascinating like opaque worlds. None of them publicize themselves. You don't know who they are, how much they invest, what they're interested in. They're not like on Twitter broadcasting that they're actively investing.They're very private about it a lot of times. so it's yeah, it, it, it's, it's a whole separate universe. It's actually really, really fascinating.Nathan: [00:37:13] Yeah, well, I've been at, this is going back to the side of running a venture fund, but what have been some of the hardest aspects of it?Li Jin: [00:37:21] Everything.Nathan: [00:37:25] It's not, you know, VCs, don't just kick back and, you know, like Write random pieces and live an easy life. It's actually challenging.Li Jin: [00:37:34] Yeah, the, the thing pieces are definitely part of, but that is done like middle of the nights and weekends and on Christmas day, like that's when I do my writing. And then during the day, it's like a ton of pitch meetings, founders meeting with portfolio companies. It's, it's just this constant onslaught of like everything that you need to do constantly.No everything about it, husband. Like a really interesting exercise and I've, I've been going through it for the first time of year, because this is my first fund. Like I used to work at a firm that had 200 people. And so I didn't have exposure to all of the different elements of running a VC fund. I didn't, I didn't use to have to fundraise.I never had to talk to LPs. I never had to, there were like teams internally that. Supported portfolio companies after the investment team decided to invest. And so that was also less a part of my job before and now I have to do literally everything. so yeah, everything has been challenging. Like fundraising was challenging.Keeping on top of all of the deal flow has, is, is like immensely. This huge, it's a huge time commitment. then making time to support your portfolio companies. Is this other big, like. Pocket of, where we spend our time and then, and then just like a company as well. We never stopped thinking about fundraising and like the future fundraises, I thought it was like, you raised the fund.You could just like, go deploy the fund. And then someday in the future, distantly, like you you're like, Oh, I have to raise another fund. I'll go do that. But it never ends actually. It's just like having a startup, like we it's like you close fund one. Then at that time, a ton of people are like, Oh, you have a fund.Like, let me invest in you. And then you have to like, keep them warm. So the second fund, and then like you close that. And then the third fund, like you never stopped thinking about that side, which is, yeah, it takes up a ton of like mental resources. In addition to like the core Day job of deciding where to put capital.Nathan: [00:39:43] Yeah. So for anyone listening in who is currently a founder has been considering being a VC regresses. In fact, not greener.Li Jin: [00:39:53] Well, I think the grass, I don't know, the grass may be a little bit greener because if you're able to raise the fund, you have like this built in revenue stream for the next 10 years, which is nice. and you don't have to deal with like, All of the, like the scale of the people issues that you have to deal with is not the same as like scaling a huge organization.But it's definitely not a walk in the park.Nathan: [00:40:19] Yeah. I believe that, I mean, just a little bit of, we were talking a little bit before we started recording a little bit of angel investing that I've done thinking about like eight or nine, investments. And even then I've been like mediating things between founders and stuff like that. And there's just wherever you turn in, in the wonderful world of business there's issues to deal.Li Jin: [00:40:41] Yeah, exactly. There's, there's no easy jobs unless you've like inherited something. I think.Nathan: [00:40:48] Another interesting thing that you've been doing, that I'd love to talk about is your course on building for the creator economy. what, what sparks, why to create the course and, and hasn't been going so far.Li Jin: [00:41:00] Yeah, absolutely. So the backstory is. Well, two things. One is like, I've been asked to write a book, create a course, like do more Content by basically everyone. Everyone is constantly asking me to like, write more, publish more like synthesize my thoughts more. And I've always been kind of pushing back on that, like, I don't have the time to write a book right now or teach a course or like, you know, build more content.But like I knew that the demand was there. And then coupled with that, I invested, end of last year into a new platform that Goggin Biani and West cow co-founded it still does not yet have a name named TBD, so we shall call it. And what's this new company. So I invested in going in with this new company, which is a platform to help experts.Builds and offer cohort-based courses. And so, when I was chatting with them about the company and the idea and the fundraise and everything, we were brainstorming about how it could be really good for me to be one of their initial instructors. And, you know, there's this initial instructor batch on their platform actually has all sorts from their cap table.Like me, Lenny saw hell pump, we're all investors in this company. And so. It's kind of like where we're, co-creating the platform with them and, you know, flagging issues as they come and really, helping them to realize like here are the opportunities to build better products. and so that was how the course came about.It was the combination of both, this platform making it much easier for me and taking a lot of work off my plate in terms of the logistics and everything behind the scenes of. Creating this course. plus the fact that like I knew that there was market pool for it, and the creator economy is such a huge area of interest right now.But I felt like there wasn't a really good cohesive, sequenced, like package of information that was all like very carefully curated and packaged together into something really useful for founders. So I decided to build it myself.Nathan: [00:43:14] It's, it's been fun to see all the cohort based courses come together and, and, you know, Yeah, it was basically on his name is terrible. He's been on the podcast before Tiago Forte, Tiago done with, Building a Second Brain. And, it's just amazing to see in David Perell as well, right. With the two of them together with Write of Passage. it's been amazing to see the different business model and it'd be like, So much more effective than even everyone was doing three years ago or five years ago of like, here's all the videos you go through it, you know, maybe it's a $300 price point, but most people drop off or something.And so in this case, you're seeing a thousand dollar price point or 2000, or I think I just have one that somebody launched it, you know, it's a $5,000 for the course and it's starting to really feel like, Oh, this is an in-depth. Uh, it's like a serious college class, you know, whereLi Jin: [00:44:17] Yeah.Nathan: [00:44:18] Everybody else and, and everything.Li Jin: [00:44:20] And I think people are, it's really interesting. The variation in prices, right? Because a newsletter is basically priced at. A hundred dollars per year, roughly that's probably the average price point of a newsletter, like $10 a month, a hundred per year. The typical CBC is priced at like a thousand dollars.So 10 times the yearly revenue that you're getting from a newsletter subscriber. And so over the course of a year, are you communicating just as much content as the course provides? Probably. And so what does that Delta, what does that 10 X Delta representing? I think it's representing. Accountability, like accountability of actually getting through the content rather than just getting access to the content and not going through it.I think it's community, of like light like-minded peers who are going through the content in the course with you, who also enhance the learning experience. And then I think it's the direct line of access to the expert, the course instructor who's. Whose brain that you're tapping into in a very direct way, versus like having, like reading a newsletter by them, it just feels a little bit more, impersonal and less direct. And so I think that's what the GAP in prices represent, but it is really interesting to see. Especially firsthand now that I have this course, and I've also been, co-writing a paid newsletter with the guys at the, everything, every bundle, just to see like the huge chasm in price points, like there's.Just huge variance in price points and how profitable each activity is. And, yeah, I think we'll see more people start to have our cohort based courses. And I, I hope that like more creators realize that this is an option. I would caveat that it is like a ton of work to create a cohort based course.Like I've probably put. A hundred hours into the content development for this thing. Like, I didn't have a Christmas last year because I was building out slides and doing research for this. so it, it is a lot of work, but it's pretty high ROI.Nathan: [00:46:34] Yeah. Well, I like what you said about. Making 10 X the, I guess it'd be the ARPU, the average revenue per user, you know, a thousand dollar course versus a a hundred dollars a year subscription because one of them, you have to show up 52 times a year with high quality Content. And then the other one, you have to do a whole ton of prep work.But you can. You know, you can reuse that you can run the course multiple times a year or multiple years. and then you probably like, as you're in the middle of this now, you know, you're, you're dedicated. It probably is your primary life. in addition to it's your other full-time job as youLi Jin: [00:47:15] Yeah. Yeah. When you run the course, that basically is all consuming of your life and in the weeks leading up to it, it's pretty intense as well. Whereas I think writing a piece of content, you kind of do it on your own schedule. If you get busy, it's like, Oh, I'll just do it next weekend. I'll write it next weekend.You can't like delay the chorus because it's on everyone's calendar and there's a start date to it. And that. You know, you've accepted student's payment, you have to deliver the course. And so there, there's also accountability for the instructor to, to create all of the content in a way that doesn't really exist for a passive subscription.Nathan: [00:47:54] right. How'd you think about the price point on it? What did you debate price that you settled on?Li Jin: [00:47:58] 1250. Yes. It's 1250. I, it was determined in conjunction with, Gargan and Wess company team. They should really find a name. And I think, it was, I mean, it felt premium. Cause I think all of the other courses that they've run so far were less than that. but like it felt fair because, For a few reasons. One is like, there's a ton of original content that I haven't talked about written about. Like it's, it's brand new from my brain.Like these are students who are accessing it for the first time out of like any people on earth. So that's pretty special. secondly I think it has real business value to people like it, it, the Content has the ability to really shape company strategies and to like inform the products that they're working on at the time.And that they're building. And so what is the ROI, if you're able to make a better business decision than you were before, like that's really high ROI. so the price point ultimately felt fair to us. I was a little bit nervous about it. Like, are people willing to pay this much, especially since I'm already pretty prolific in terms of, podcasting and writing and to my surprise, it was like wildly, wildly oversubscribed. And honestly, I think we could have probably charged more, but I don't, you know, I don't want to go too high, especially for the founders that I'm targeting. I think there's also opportunity to like better price discriminate in the course world. Like for founders, I would love to offer a discount or have them be sponsored or something versus for investors and VCs who want to take my course, like I want to Jack up the price because they could probably pay anything.Nathan: [00:49:48] That's interesting. If, if, if you said, you know, the price for the course is $2,500. but if you're an early stage founder, you know, apply here, we want to make sure that you're serious. You're all of that. but apply here and you can take it for a thousand dollars or something like that.Li Jin: [00:50:04] And that's what schools do. That's what universities do through financial aid, through need-based financial aid is they perfectly price discriminate every single student based on their capacity to pay. We just don't think of it that way.Nathan: [00:50:16] Right. Oh, that's fascinating. How does the course fit into the rest of your business model of, you know, how do you think about how it intersects with the investing and everything else?Li Jin: [00:50:28] Yeah. I think if it has like, hopefully a really great way for me to build relationships at scale, with a bunch of really high quality founders and to tangibly provide value to them, such that I become their investor of choice. So it definitely has that intersection with my day job. but beyond that at a broader level, beyond just the relationships that I'm forming with my students who represent a ton of early stage founders, I think it also has been this amazing opportunity for me to crystallize my thinking and to put down a lot of thoughts that have been swirling in my mind, but like we're kind of disorganized honestly, and, and weren't structured in any sort of cohesive way and it helps me.Crystallize and sharpen my own thinking such that I'm able to better like guide my existing portfolio companies or better able to offer value to the companies that pitch me.Nathan: [00:51:18] I like that. Okay. Last question. On the, on the course side, you had the application side, right? When someone, they can't just come and buy it, you have to goLi Jin: [00:51:27] Correct. There was an application process.Nathan: [00:51:29] How did that play out? And what was the reasoning behind it?Li Jin: [00:51:31] So the application process was because we wanted to cap the course. We want it to cap the course at a number that felt kind of still intimate and it wouldn't be like, 10,000 students in the course live learning from me. so it ended up, so right now the course is 150 students. So we reached like the hard cap, and we got way more than 150 applications.And so we had to unfortunately turn people away and. You know, tell them to stay tuned for the second cohort. timing TVG. So the reason why there was an application is because for a cohort based course, you need to have constraints on capacity because like people are paying for your attention and your time and access to you.And that access can't be scaled, infinitely.Nathan: [00:52:23] That makes sense. I imagine it would also play a role in conversion rates as well, because as someone fills out an application, they're probably getting more invested and then there's, there's next between that. And when they actually have to pay, and then there's also this feeling of like, Oh, you got accepted in.Okay, now I shouldLi Jin: [00:52:41] Yeah.Nathan: [00:52:42] Pay and right. There's the accountability side of it. Okay. Now I should follow it through and actually make it happen.Li Jin: [00:52:47] It was, yeah, there was such interesting things that happened that I learned throughout this application process. One is, well, the application was actually kind of involved. Like they had to put in a lot of information. And so I thought like, Okay, well, we'll probably get really high conversion off the application.Like if you went through this form, this type form, like you're probably in, but that wasn't the case. Not everyone actually confirmed after the application. So there was a bit of drop-off like, I think every time you add a step there's drop-off, and then, what was the other thing I was going to say?The other thing was like, every time there was a milestone or a checkpoint to get through, like the application from application to like. Conversion or acceptance to conversion. Like people shared those moments on social people, screenshotted their emails. And they were like, I got accepted into this course and I was like, this is mind-boggling that like, you're basically tweeting about like paying a content creator.And like, and, and like celebrating that, like usually people don't celebrate giving a content creator money for something like that's pretty rare, or like it's even rare that people tweet about like buying a product. But like for this course, I don't know. It, it it's like college admissions people. It is a milestone.And so it became a milestone. Like we created a milestone for people and it continues to this day because the course is happening right now. People are tweeting about like just finished workshop one. And it was, you know, it was awesome here. All of the things that I learned, like everything has become like a milestone and it's, it's honestly incredible to see.Nathan: [00:54:29] Yeah, that's amazing. Well, we should leave it there. I love the chat for a long time, but where should people go to follow you and learn more about the fund and subscribe to your newsletter?Li Jin: [00:54:39] Yeah. So the fund website is atelierventures.co. My personal newsletter is li.substack.com. People can also follow me on Twitter, that's probably my most active content sharing channel. I'm @ljin18 on Twitter and yeah, I think that's about it. Thanks so much for doing this.Nathan: [00:54:59] All right, thanks. I'll see you later.Li Jin: [00:55:01] All right. Take care.

Lenny Rachitsky sold his company to Airbnb years ago and he spent a bunch of time there as a product manager, working on growth.Now Lenny's full-time job is his simply-titled “Lenny's Newsletter”, where he shares everything he's learned about building products and teams. With over 3,200 paying subscribers, Lenny's Newsletter brings him a larger income than he had at his tech job!In this fun interview, Lenny shares his journey—how he went from wanting to found another startup to being a one-man newsletter business, and the lessons he's learned along the way.You'll learn the “value-add” for a paid newsletter that's been a great success for Lenny, and how he's avoiding the trap of workaholism as he builds his business.Lenny also shares how he never runs out of topics, and how he stays interested and curious so he can enjoy running his newsletter for years to come.Plus, as popular as paid newsletters are, they come with some important downsides! Lenny reports from the trenches on what they are and how to deal with them.Links & Resources Airbnb Coda - A new doc for teams. Why a Paid Newsletter Won't Be Enough Money for Most Writers (And That's Fine): The Multi-SKU Creator - Hunter Walk Lenny Rachitsky's Links Sign up for Lenny's Newsletter Twitter: @LennySan LinkedIn: Lenny Rachitsky Episode TranscriptLenny: [00:00:00] I find there's any time not spent creating high quality content is not time well spent over the long run. It's all about just valuable content. You know, if you provide value to people, they're going to want it and they're going to subscribe and follow and pay.Nathan: [00:00:18] Today's interview is with Lenny Rachitsky. Lenny's company was acquired by Airbnb more than seven years ago. He spent a bunch of time at Airbnb as a product manager, working on growth, where he became fascinated with things like, how do you manage a team? How do you grow a company? What are the product management best practices?All of these things after leaving Airbnb, he started a newsletter just called Lenny's Newsletter, and it now has over 3,200 paying subscribers. he's now earning more from his newsletter than he was at his tech job. Quite a bit more actually. And we get into so many things, but how to keep writing newsletter really fun, how to grow and scale your audience using guest posts to get those first subscribers so much good stuff.Let's dive in. Lenny. Thanks for joining me today. Thanks for having me. So you actually kicked off our call and kind of a fun spot. So I want to start the interview there. And that was, you just said, so did you read the New Yorker article, you know, and, the New Yorker just did another article about newsletters.Why don't you give us a high level? Cause it kind of takes us into the state of newsletters, you know, on the web right now. Lenny: [00:01:28] Oh, so I find, I generally try to avoid pontificating on the state of media and newsletters, because I feel like that's not my depth. There's a lot of newsletter writers that like come from media, I've thought about, you know, this whole space of newsletters for a long time.And it's fun to think about it and talk about, and, and tweet about sometimes. But yeah, I don't have the most thorough opinions of the whole industry, but. What I find is when people do this kind of like overview of what's happening, it's always this interesting combination of like, Oh, here's all the good elements.People can write whatever they want. And they have freedom. They're running their own business and creating their own kind of life. And then there's like, Oh, but all these dangers, what are they, what's going to happen? They need health insurance. And how do we moderate all these folks? And who's going to win.And how do you, how do you not create this? Just like 1% that does well. And so, so the post is kind of essentially going through a bunch of stories of all those things happening. And I think the conclusion as always, as it's complicated and there's good and bad end, we'll see where it all goes. Nathan: [00:02:32] Yeah.It's been fascinating to watch how the landscape has changed over the last, you know, seven or eight years since I've been working in this space. But you know, particularly the last say 18 months as Substack has gained a ton of traction. I think a lot of people, this is kinda what I want to talk about next.Who maybe in the past would look at newsletters and go, that's an interesting business. Like that's a thing. Maybe that's your lifestyle business. I don't know I'm going to go do a startup, you know? that was all the mindset. And now Lenny: [00:03:05] that's exactly what I did. That was my whole plan is start a company.And then I started this newsletter on the side just to like play around with something and magically, it turned around and the newsletter became the main thing that I do. Nathan: [00:03:16] Yeah. So let's talk about that more. Cause you spent what? Seven, eight years at Airbnb working on, on growth and product management. and so I'd love to hear, well, let's see, let's talk about just the transition out of Airbnb and then what was next?Lenny: [00:03:34] Yeah, so I left Airbnb about a year and a half ago. Last March. I was there for seven years, sold my company to them and. My plan a, when I left, first of all, I had no real plan. I was just like, I need to, I need to do something different. I need to move on to some new, and so plan a was, likely start a company again.Plan B was maybe do some advising consulting plan C was maybe join a startup plan. D was maybe join a big company. And now are on those lists of plans that I have make a living off writing a newsletter. But what started happening is I first started collecting my thoughts of what I learned at Airbnb and things I've done in the past, just so that I don't have to relearn them.When I start a company is I put out medi posts and that did shockingly well, and then I put out a few more medi posts and those did well. And then somebody suggested I switched to sub stack to, you know, to the classic reasons to have your newsletter it's own your audience, to not give all the benefits and medi and those kinds of things, which we can talk about.And that just kept going well. And it was always a side project that everyone around me was like, okay, stop this writing thing you're doing. And you really want to do a startup. You should really focus on that. And just spending so much time writing, what are you doing? But I just kept doing it cause it was interesting and fun and people seem to value it.And I had a good conversation with a friend, maybe six months into it. And his advice was okay, this seems to be working well. People seem to value it. You seem to enjoy it. Maybe just try that for a little while longer. And don't put all this pressure on yourself to start a company now. And so I did that and it just kept growing.And eventually, this year actually around COVID beginnings of COVID, it was like a year since I left my job. I had no income. I didn't know what I was going to do. All my stock is down. I didn't know how I was going to make money again. And so I decided, let me try this pate version of the newsletter and.And that kind of took things to the next level. And now we're here where I'm making a lot more than I made it Airbnb. And I don't have any future plans beyond this. Nathan: [00:05:38] Yeah. So did you, figure out what the start-up was going to be, or was it still, you were playing around with ideas and the newsletter was a playground to try out or to like think through some of the things you were considering.Lenny: [00:05:51] Newsletter is more of a playground of collecting things that I've learned that I wanted to crystallize, you know, as they say, I don't know what I think until I've written it down. And I was, it was an excuse to crystallize things that I've learned over the past. but in terms of the startup, I had, I had a spreadsheet of 50 ideas that I was working through one by one prototyping, asking friends, trying to research them.So as, as, as I went through like 10 of them, by the time I stopped. And, none of them, none of them really stuck. That was part of it is I didn't find anything that was, “Oh shit! I really need to stop everything and do this thing.” if I, maybe if I had it, it would have been some different, but startups are hard.It's like a hard life to pursue. And so I'm happy not to do that right now. Nathan: [00:06:33] They are. They're very hard. And especially that, I don't know those first two years or three years, you know, before it gets a team in moment it. It just it's really hard. So, so at that initial traction, that point where you're like, Hey, this is working.What were those signs that you look for? How was it a nber of subscribers or was it just moment a rate of growth? What was it? Lenny: [00:06:58] I'd say early on, it was very qualitative. I just kept getting these really nice messages from people about how valuable some of the stuff I'd written had been. So is that plus continued growth.People just continue to subscribe and come back and not unsubscribe. That was a good sign. and then, yeah, I guess it was those two things, qualitative feedback and just growth continue to happen, even when I wasn't doing anything. And also the feedback was coming from really smart, successful people that I really respected, so that added to it.Nathan: [00:07:33] So those things, I think what's interesting about that is that. It has you focusing on the quality of the content rather than the results.Lenny: [00:07:41] Absolutely. That's what I find over and over again. Anything that I do, that's not just create high quality content does very little for the success of the newsletter.I find there's any time not spent creating high quality content is not time well spent. I just keep finding it over and over. I tried like Twitter ads. I tried a referral program. I tried, cross-promotion across newsletters and none of that really did anything. Although initially there were some things that, that I did that were really impactful to help jpstart it, which we could talk about.But, but over the long run, it's all about just valuable content. And, you know, it's like if you provide value to people, they're going to want it and they're gonna subscribe and follow and pay. So the more you could just provide value, the more successful you'll be. And that's what I keep finding. Nathan: [00:08:28] When I think another thing in that is.The type of people that you're writing to. So you're looking at a lot of that qualitative feedback was from people that you really respected, you know, whether it's industry peers or others. And I find that when I'm writing to someone, who's one of my peers, the quality of my writing is so much better. If I even have this in mind of like, okay, this didn't happen, but let's say this person asked me for advice on how to get your startup to your first 5 million ARR.You know, then if I write to them, it's just better. Right. And then I think like reading a lot of your early stuff and even the way that you write today, I get that feeling from it of like, Oh, this feels like it's written to Lenny's peers and his friends rather than from the place on high, where Lenny that, you know, Yeah, the startup expert is writing to the masses because it just, it comes through in your writing in a different way.Yeah. Lenny: [00:09:26] Yeah. And I think a lot of that comes from, I don't know if insecurity is the right word, but I just, I don't feel like I have the answers and I'm not the smartest, most successful person. And so my lens is how do I just give you on arguably correct advice that either comes from successful, smart people or a bunch of analysis over what's worked or.Or something like that. So, so the lens I use isn't I know a lot of people and I like your framework of just like pick a person and a specific person in my end, right. To them. I use it more like a broad lens of if I'm like a founder reading, this is this like actually useful to me or is this just like a bunch of fluffy stuff?That sounds nice that I can, I'm going to just forget immediately. And so I always come back to you as, as concretely. Actionably valuable immediately to somebody. And if it's not, then I refine it further and cut out stuff. That's not actually useful. Nathan: [00:10:17] Yep. That makes sense. What were some of those things that worked for the early on that you were talking about to get the initial growth?Lenny: [00:10:24] So, so I started, I started at zero is everyone starts with, and what I, the way I first launched the newsletter was actually on Twitter and kind of like, it kind of created this interesting back and forth between medi and Twitter and sub stack. So I wrote that first piece on medi and it got like featured by medi.The, it was about Airbnb. What I learned at Airbnb, the CEO of Airbnb sent it out to the entire company and it got into this collection. So it just got a ton of use. And that led to some Twitter following. Somehow, they kind of found me on Twitter. And then as I was reading, you have much of a Twitter following.Not really. I had, I had like a few thousand followers, something like that, which is not from Nathan: [00:11:06] being on Twitter for Lenny: [00:11:07] years and yeah, exactly. Yeah. Yep. Which is, you know, some people have less than a thousand, so that's a different place to start. And I'll also add, I've never like focused on Twitter followers.I was just like, how do I share valuable things with people? Cause I just want to get it out of my head. And so that was, as I was writing these medi posts, I was also tweeting little nuggets of things that either were in that post or just couldn't make it into a whole post. So I started just kind of doing both things, tweeting and medi posting and that built up the Twitter audience just because some of the stuff was proved to be really valuable.And then when I launched the sub stack, I basically just tweeted out, Hey, I'm launching a sub stack newsletter. You should subscribe. I don't know what it's going to be at, but it don't miss it. And so that got me to my first few hundred subscribers, just like tweeting about it. And I had maybe like 10,000 followers at that point, something like that.And then, and then I did a couple of guest posts, one on Andrew Chen's blog and one on the first round review. And that it's a tweet Twitter. Plus those two got me to the first thousand, essentially. Plus in that time, maybe like 20 actual posts that were valuable enough for people, right? Nathan: [00:12:22] Yeah. Is guest posting something that you would recommend for someone I'd Lenny: [00:12:26] say?Yeah, I'd say initially when it's early, for sure. Because if you think about just marketing anything, you just want to go to where your audience is. And if you can write something that in a place somebody already has that whole audience and. Show how awesome you are. They're going to come follow you wherever you are.So I find it, I found it to be super valuable, but you have to just pick the right blogs and newsletters and do a great job. Nathan: [00:12:54] Yeah. That's I mean, in the early days of my newsletter, maybe after I had it with 2000 subscribers, a thousand, 2000, somewhere in there, I started doing guest posting pretty heavily.And it's exactly what you said. Like some people think about guest posting as like, Oh yeah. Here's this thing that. I wouldn't put it on my blog, but sure. I'll try to see if you want to run it. It's not an effective strategy instead of you're like, here's the best content that I wrote, like, et cetera, writing one, an article versus specialty magazine, which is a web design Lenny: [00:13:24] and development.My wife's been in that. Oh, Nathan: [00:13:26] nice. Yeah, she's a designer. Yup. and I read them a lot and so I wrote a post on product launches. That was 4,000 words, long, all kinds of detail, everything, you know, I tried to put as many real nbers in there as possible. And just try and be like, this is everything I've got, you know, and that post, I think got me, well, had a great call to action for like sign up for a free email course at the end that I had, like, here's a ton of great value.And then if you want even more like in the weeds, nerdy stuff, he, you know, he here's even more. And that picked up like 2000 email subscribers from a single post, which at the time, you know, we're like, 50% ground, you know, it's, it's pretty amazing to thousands of them a lot. Yeah. But even if at that stage, if you're getting a hundred or, or 300, like that's totally worth it.Lenny: [00:14:15] Yeah. Similarly to the one I did with Andrew, I worked on it for like months. It was a 28 ways to grow supply in the marketplace. And I had like all these examples and, and quotes and all these things and I showed it to him cause we got to know each other a little bit on Twitter and he's just like, and I republish this on my blog.I'm like, Well, can I also publish it of mine? It's like, let's do a 24 hour exclusive. And it was a really tough call cause I was really proud of it as the best thing I'd written up to that point. But again, it, I think that's why it worked because it was high quality. Nathan: [00:14:47] Th the exclusive is interesting because it still gets out to your audience, but it leads over there.Lenny: [00:14:53] yeah, they're not, they're not as into that. They don't want you to republish it at any point. Nathan: [00:14:59] Yeah. And the, I mean, they've got quite a content strategy and Lenny: [00:15:02] yeah, they're amazing. I'll give you an editor. It's amazing. Nathan: [00:15:05] Yeah. So it's guest posting something that you've continued to do, or is that more for initial traction and then just focus on your own property?I've done Lenny: [00:15:14] that a couple of times. I did a couple more first round pieces actually, now that I think about it, but it was more just, it felt good. It wasn't. It didn't really do much honestly directly, but you know, all these things add up. But what I find now is that now that I have a meaningful audience, I can promote other people through guest posts, which one people come to me to try to do that, which is really funny.And then on the other hand, it saves me work because I get this amazing content from someone. Great. for a week because with a paid newsletter after right every week forever, and the more amazing pieces of content I can create that I don't have to write myself the better. So, Oh, it was a balance obviously, but what I try to do is collect just like the best people in each field and have them write and definitive answer on a topic that people are asking me about.And so it's kind of flipped now, which is kind of interesting Nathan: [00:16:06] when I think having the. Well, you, you basically set the bar for the content and then you've said, If anyone in the industry who's really experienced can meet that bar or exceed that bar. Then I would love to have you. And then it's, it's not a like, Oh man, this article is not from lending this week.It's from some random person it's instead like, Whoa, I can't believe Lenny got this person to come on and share this level of detail. Lenny: [00:16:31] Yeah. And here's a rule of thb I'll share is if someone reaches out to me to try to do a guest post. That automatically means they're not going to do a guest post. I have to go reach out to them because I find that the people that I want to do the guest poster, often the ones that aren't interested in doing one.Nathan: [00:16:49] Right. Have you ever had, I had someone who reached out to you do a guest post that like met the bar for quality and was really good? Lenny: [00:16:56] Not yet. Okay. I'm sure it'll happen, but I wonder. Nathan: [00:17:01] So I'm just spit balling here. I wonder, like I'm saying, if I were to pitch you on a guest post, like if I was listening to this and heard like Lenny doesn't take outside pitches, if I were to be like, yes, but he hasn't seen my content.What I would do is I would pitch you with the entire article pre-written and I would say, okay, but. You know, what about this? Do you think that Lenny: [00:17:23] would work? Oh, that would definitely work better because I find that once I get started with someone, it's hard to just, if I find that it's not great, it's hard to be like, no, nevermind.So yeah, the more I can see where you're going to land, the more likely it is to work out. And what I find is often with even the most amazing people, there's a bunch of back and forth, right. Push them to make it more concrete and more actionable. And more tactical. So, so I, I love seeing the draft cause then I can see how far it is from something that's going to be amazing.Nathan: [00:17:53] Right. And you can see immediately if, if this is an idea that's been played out and done plenty of times before, or if you're like, it's not good yet, but I bet if you change it. Exactly. Lenny: [00:18:03] Yeah. It could be. Yeah. There you go. There's a, there's a good Nathan: [00:18:06] trick. And so, I mean, we can carry that forward, right. If even someone who, doesn't often take guest, I mean, it's, it's basically.It's similar to what you did with, Andrew of you didn't pitch him, but you said, Hey, I'm working on this. I don't know. I don't know exactly what you said, but I'm working on this. Can you give me feedback? Can you give me ideas? and then he's like, not only that, but can I run it on my, on my site?Lenny: [00:18:32] That's exactly right. And actually the first round, it was the same way I had kind of the outline in a lot of the posts and I showed it to them and that got them excited. Nathan: [00:18:40] Somebody who did this really well, And I feel bad that I'm spacing on his name right now, but who runs groove, groove, hq.com. they built a really, really popular blog on their journey going to 500 K.now I'm trying to think of 500. I'm trying to think what the nber is anyway. It's a lot of subscribers. no, sorry. It was on the, for their software product. Maybe they're trying to get to 5 million, 5 million ARR or something like that. They had some. It's was probably 500 K of MRR is what, the nber they're turning.Cause I remember looking up to it being like convert your wasn't at that level. And I was like, Oh, that would be cool to get there. You know? and something that he did really well is have a content like a sort of an advisor group. Where he basically reached out to a bunch of smart people and said, Hey, I'm going to write stuff on these topics.Would you mind if I sent you a draft of it from time to time for you to look over it? If I think it's particularly relevant to you? and I think that can work well because, so he looked me in on that and I was like, yeah, you're writing great stuff. I'd love to see it before it's published. And maybe you share some tips or insights.yet he'd been shot plenty of other people. And then what happens is when he would then publish the piece, he would email the same group and it was probably 20 people or something and say, Hey, thanks for your help on this adhere to his life. And then I'd see all those people tweeting about it and sharing about it because they had like a, an emotional, or they had an investment in him and his success.Lenny: [00:20:13] That's actually something I forgot to mention that I found really effective when I launched, when I launched the paid plan is I did exactly that with my launch announcement and ran it by folks like Andrew Chan and, and a bunch of other people with a large Twitter following, like generally to get their feedback on how to frame the announcement.Cause there were supporters along the way and then also led to them, tweeting about it. And that helped a lot. Yeah, that Nathan: [00:20:39] makes sense. Well, let's turn to page. What made you choose a paid newsletter as the business model compared to, you know, many of the other ways that you could earn a living in, in startups or from a newsletter Lenny: [00:20:51] first?I'll say that it there's a lot of downsides to going pay that I didn't think about until I went paid one being you're, like I said, you're stuck writing every week. Some people do it daily. I don't know how they do that. It's blows my mind. but you're basically stuck doing it for I in theory, forever because people are paying you these annual plans and I don't, I stop unless you just shut it all down and just refund everybody their money, which is hard to do psychologically.So that's one is you just kind of have to be ready to do this for a long time. You know, maybe if it's like a few years and you can just move on, that's probably fine, but you can't stop. You know, in a few months. So for me, it took nine months to get from starting the free newsletter to switching, to paid.And a lot of that was building confidence that I could keep this up. And I had a topic every week that I could write about that I was excited about. So that's the reason that it's, it's something to think about the other is before I wrote every week and it was totally free to everyone. And then once I flipped the switch, I'm doing the same amount of work, but almost all of it is not hidden behind a paywall.And it just feels really bad. Like just like man doing all this work and no one's going to see it. Cause initially you have very few paying subscribers and it's just like, feels like it goes into a black hole. And if, kind of get used to that of just like, well, I'm getting paid, people are paying for it.That's the benefit. And that's the, that's the cost of writing this and doing all that work. So, but that like, I dunno, like, like it feels like an obvious thing, but feel the feeling of it. It doesn't feel good, but it all, it all works out. Nathan: [00:22:24] Yeah. Digging in on that. How have you found, like your writing process and like that showing up really consistently and the pressure of needing to publish could feel like a hamster wheel.It could also be turned into a system. And so one of I'd love to hear anything that you've done to establish your process, to bring it from like hamster wheel to a reliable, you know, productive system or if that's even happened. Yeah, Lenny: [00:22:53] totally. And if we want, we can come back to the paid, the launching of paid.so, so in terms of my process very much the way I describe it, as it feels like a, Boulder's always chasing me in, as soon as I'm done with one week, there's just like the next one's coming. And I have to always plan ahead and it's a real thing and it's used to be stressful, but now that I've done it long enough, I, I, it's, again, kind of the confidence where I'm like, okay, I've done this for like a year and a half now.I'm not worried. I'm not going to find something great this week. But what I've done now is, I basically have three months of ideas mapped out. So I have a Coda doc where I have every topic kind of on its own page, kind of mapped out for the next three months, roughly just like the topic is the headline.And then for the more eminent posts, I've I basically go in there and just flush out with bullet points initially, just like the things I want to say and thoughts that I have as I think about it. And then as it, and then for the next like month, I go deeper. So it's kind of this like spectr of depth the next few months, the what's cool about the format that I happened upon is, is it's an advice coln.And so that means people send me questions that they're tackling in real life. And so I have this large backlog of. Really great questions from founders and product managers and growth people. So I'm finding, I'm never going to run out of things to write about at this point. And if I do, I could just go back and do better on things that have already written up.So the topics don't seem to be a problem, but then actually delivering high quality stuff every week for sure is a challenge. What helps one is just thinking a little bit ahead. So. So I'm trying to, I always try to be like a few weeks ahead of like done content, but I never actually get there. So it's usually like the next post is like 80% done a week ahead of time.And then the rest are like 20 to 10% done. And then the rest are just headlines. and otherwise it's just making time to write. I block out my morning site. I have no meetings until 3:00 PM. That's my new rule that helps a lot. And it's hard to do if you have a day job and. That just always comes back to, no, you can't do this.If you have a day job, I don't know how people have a newsletter. That's good with a job. And that's the secret is I have time to do this stuff. And most people don't like, I don't know how you do it. Newsletter having running a company. Nathan: [00:25:13] Well, I mean, I do a lot of what you're talking about of like, yeah, this will totally be done for this week.And then you were like, wait, I said my newsletter every Tuesday and, yeah, I don't know with Tuesdays, but it sounded good. Someone Lenny: [00:25:25] said it, it was the best data send for open rates and Nathan: [00:25:28] now it's stuck. I think it's that I don't want to be in the Monday morning inbox. and so that, but I don't also want to be at Friday end of the week.And so I'm like Tuesday, you Lenny: [00:25:39] guys, you guys must have data on which day of the week is the highest open rates. It's Nathan: [00:25:42] Tuesday.not so much definitive, like it, it's not like wildly, you know? but, but Tuesdays are good and Lenny: [00:25:55] shout every, every percentage Nathan: [00:25:56] we can get. Yes, exactly. And that's, you know, we send a little over a billion emails a month, so we have a good amount of it can amount of data that Lenny: [00:26:04] we, you heard it here first Tuesdays.Yeah, Nathan: [00:26:06] exactly. So on, let's see, Oh, with the content coming out, that's something that I always run into. Like I was actually going to send a year in review posts tomorrow Lenny: [00:26:17] and that's what I'm doing. Nathan: [00:26:19] Yeah. But it's not done, you know? And I was like, Oh, it's end of the day, Monday. And that's not going to happen between now and then.And so I have basically the same process that you do of like, this is what's coming. And then here's the ideas. And, and dripped out from there. something else that you mentioned that I thought is a really good point is the asking. It's not well asking your audience questions and then asking them to submit your questions.So one is the generic, like, Hey, if you have any questions about these three topics, like ask why, or even if you said something like, Hey, I'm going to write about freemi a freemi business models in a couple of weeks, like submit your stories, or like you can solicit that kind of thing. Especially once you get past.Maybe two or 3000 engaged subscribers, then you start to get a good nber of things there. But then the other thing that I love is to ask, Hey, what's your biggest frustration related to life as a product manager, you know, running a freelance business, like whatever the topic is for your newsletter.and that can get a lot of good things where, you know, people will come in and say like, You know, here's my frustration. And you're like, Oh, let me tell you how to solve that. And that's the writing prompt that you were looking for to take an idea actually all the way through? Lenny: [00:27:36] Yeah. I think that I kind of made my newsletter, like I leaned into that even more and it's just like, this is purely an advice coln.Same your questions, anything you're dealing with that, that stresses you out at the office or around product or growth or managing hans. And so at least a lot of really good questions because they're very, they always end up being very real, like stuff they're actually dealing with. And I wish I could answer them all, but it just piles up.And so I have to pick one. And the other thing I have to think about, cause my newsletter has this broad spectr of product management and growth and startup stuff. And people management people join me with different, hopes and dreams for what the newsletter's going to be. So I have to balance out all these different types of content every week.So it's a weekly newsletter, so I kind of have to do. A nice balance. I can't have like three product posts in a row. Cause then all the growth people are going to leave. And so that's something I have to think about. Yeah. Do Nathan: [00:28:28] you see, is that a fear that you have, or is that, does that actually manifest in the nbers as well?Lenny: [00:28:33] It's hard to see the nbers. I definitely find people on subscribe, but they're just like, nah, not what I thought it was going to be I'm out, but I don't know what the root causes and it's all anecdotal, but I do. It just feels like that's probably what's happening is they're just like, I don't care about growth, stop talking about growth, Nathan: [00:28:52] right?Yeah. And you get both sides of it where someone comes in from the greatest article they've ever read on growth. They're like, Oh man, this is all he ever talks about. It's incredible. And then other person comes in from the same side on a product management. Or people management or whatever. And they each think that you talk about something.Lenny: [00:29:09] Yeah. And that reminds me of something I've realized about this whole, newsletter game is that it's really important that you stick to what you enjoy and are curious about yourself and are interested in writing about versus what people want you to focus on and write about, because coming back to your question about how to keep it up, I find that you're just not going to keep it up.Well, if you're writing for. What people want you to write versus like stuff you really actually are curious about and want, wanna write about. So I try to do like a 80%, what do I actually care about this week? And I'm excited to write about with a 20% of like, well, people care about it this week. And is this a topic that's top of mind for anyone?Because otherwise you just, you just like created a job for yourself. You don't like, and why did you even do that? Right? Nathan: [00:29:55] Yep. That's good. And especially because it gives you permission as your interests change over time, right? For me, I started writing about designing iOS apps. Like that's all I cared about.And then it was like, what's the marketing and more general design. And I haven't designed an iOS app in seven, eight years. I don't know if those subscribers Lenny: [00:30:14] are still around Nathan: [00:30:16] there. There are some of them, you know, and, but if it's around what you're interested in, then it's much easier to let go of those subscribers.Whereas if you're like, no, I have to keep everybody on the list. Then you're going to. You're trying to force yourself to be interested in things that you're just Lenny: [00:30:32] not. Yeah. And it's just, you're not going to enjoy it. It's not going to be good if aren't going to be like, Oh, this is, this is what I'm here for.Yeah. And so, so the key is just like just right. Yeah. So I mean, back to your question of process, I have this like list of what I'm going to write about over the next three months, but then I rearrange it constantly based on what I'm drawn to as much as I can. And that, that really helps. Otherwise you just, you just burn out.Yep. That makes sense. Nathan: [00:30:56] Okay. Now let's talk, writing, switching to a paid newsletter. what are some nbers now? As far as how many subscribers you have on the free version and the paid version? Lenny: [00:31:06] So, so I'm going to share this publicly, in parallel. And so you can see the charts. If you're curious, by the time this probably comes out, I have to have about 45,000 free subscribers around now.I have just over 3000 paid subscribers, and then I give a bunch of like comps to various groups. So it's larger than that in reality, and make it about over 600 years, more and more than I made in my. Nancy tech job, which blows my mind. Like my entire goal in the beginning of this whole endeavor was once I make more than I made it, Airbnb I'm done.I don't need anything more. I'm just going to stop thinking about growth. I'm just going to write, but it just keeps going on its own. I'm not doing anything and it's pretty bonkers. Nathan: [00:31:56] Yeah. So what was, first that's incredible. Like once you build that flywheel, it just. It Lenny: [00:32:03] keeps working. It's all, it's all word of mouth.Nathan: [00:32:07] I L I love seeing that. What, when you make the switch to pay, did you have a nber in mind of like, this is what I'm, I'm launching this paid version. We'll say, you know, I don't know how confident you were going into it. I'm always the one, like, this will probably never work, but here it goes anyway. but I always have a nber of like, okay, if I get a hundred people to pay for this, then it's working.Like, what was that first nber for you? Lenny: [00:32:32] I had like getting, getting a thousand subscribers, I'd say paid subscribers. Cause that roughly equated to about a hundred K after all the fees and. And discounts and things like that. So initially it was a thousand, which is, I think it was Kevin Kelly. You talked about and true fans.And it was very real. It was like exactly. When I get to a thousand subscribers, I was making a hundred K a year, which is very livable wage in San Francisco, you know, borderline San Francisco. Right. And so that was, that was the goal. Initially it was like, you know, 500 and then wow. It's thousand. That'd be amazing.Cause if you do the math, that's up pretty quickly with, The subscription newsletter, right? Nathan: [00:33:13] Yeah. So what have you seen on free to paid conversion rates? you know, any in particular driving, more paid subscribers? Lenny: [00:33:22] So, so if you do the math of about 45,000 free and about 3000 pays, so it's less than 10% convert, which is an interesting stat.Initially it was like 2% when I first launched. So I had like 10,000. Three subscribers when I went to pay it. And, and I had about 200 to 300 initially paid subscribers. So it was a very low percentage initially. And then over time it grows, was what was the other question? Nathan: [00:33:52] So, well, I guess, digging in on that, did you put more content behind the paywall?or did it just take take time, but what actually drove that conversion rate up? Cause you're, you know, you're pushing the eight, 9% now. Lenny: [00:34:04] So the way, the way I do it is I, I send an email once a week. If you pay you, get it every week, if you don't pay it, you get it once a month. And so that monthly email basically has to be really, really good because that's your yoursel.And sometimes I do these, like here's a peak at this week's paid post and give them a glimpse of what they're missing. And then in the fridge post I share, here's the three things you missed. So essentially it's that free posts convert it to people, less Twitter. Just kind of sharing what's going on in the pave land, but otherwise it's all hidden behind a paywall.Nathan: [00:34:37] Yeah. So about having more of those more time for those, here's what you missed. Here's the free post to kick it. Lenny: [00:34:45] It just comes back to just providing value to people and they either find out about it or they want to access it and then they end up subscribing and stick around or leaving. How do you think Nathan: [00:34:55] about pricing of what price point you set and then how do you think about that changing over time or not?Lenny: [00:35:01] I definitely spend a lot of time thinking about it. I don't know if my price is the right price at all. I experimented with various price points, but where I landed is advice I got is priced higher than you think you should. Everybody always wants to start at five bucks a month because that's the lowest you can go.And no one ever thinks their stuff is worth it. So they're just like, Oh, five bucks a month. That's that's so much money already. So, so I looked at the leaderboard. And if you think there's like these various categories of newsletters, there's news, there's entertainment. And then there's broadly just like analysis and make me smarter and better at what I do category and those charged like 20 bucks a month.So I just picked the middle and went with it. And initially when I launched, I did it, you had a display, there was a big discount. It was 10 bucks a month for a year. And then I increased or lowered the discount. It's 12 bucks a month or 120 a year. And then I went to the. 15 bucks a month for 150 a year.And I still don't know if it's the right price. There's probably some curve someone could do for me. That's like the ideal place. Although I will say when I ran a deal, it's like interesting learning. I ran a holiday deal and that drove the most subscribers I've ever had. And on one day when I discounted it by 25%, so that's probably the right answers price, a little higher, and then discounted on occasion.Yeah, run Nathan: [00:36:20] a run a black Friday or, Lenny: [00:36:21] yeah, that's what it was. It was, it was a cyber Monday holiday newsletter. Nathan: [00:36:26] Yeah. And I think that's interesting. What are you thinking about bping up to the $20 a month or going off from there? You think it's at the Lenny: [00:36:32] right? It feels so expensive. And I have this interesting.Too much pressure. Yeah. And, and I find that I have this interesting combination of people working at a tech company that it can, can expense it and the price doesn't really matter. And then there's like a lot of product managers in like India that email me and students in India. That's like the most common source of emails that I get of just like, this is a crazy price for someone in my shoes.Is there any like alternative price for folks in India, for example, and I don't know how to deal with that because. I want to devalue it, but it's also a crazy expensive price. So that's a struggle I have. I don't know. It'd be interesting. Nathan: [00:37:12] I'm trying to think who said this or a bunch of people probably have, but of being like full price or free.And they always have that sort of methodology of like, yeah. I, I think it was someone doing agency work, honestly, of like, no, there's no friends and family discount. There's no, there's nothing like that. I like these are my rates. Except for the times where I think it would really benefit you or like I'm going to do this for free.And it's very clear that this is what I'm giving you. And there's none of that. Like you're paying for it. So you feel like you deserve things, but you're paying half of the list price or a quarter of it. And so I feel like you can't be demanding, you know, and there's sort of that weird demographic. And so you could say like, look, I do full price and then I do full scholarships under.These criteria and I give out a hundred scholarships a month or 10 scholarships a month or whatever. Lenny: [00:38:02] I don't, I don't know we'll do that, but that's an interesting strategy. I do discounts of various amounts and I don't know if that's a good idea or not, but yeah, I do. I ended up doing like a 50% discount for students.and, and then I just give occasional steep discounts for folks that just feel like they, they, they would value it highly and they just can't afford Nathan: [00:38:22] it. I do like the, the students angle. Cause then it's just like, Hey, this is what it is. And people are paying for it. Right? The nber of people that are saying like, Oh, this will totally change everything.Can you give it to me for free? And then, you know, they're not invested who knows if they're going to read it or whatever else. Yeah, Lenny: [00:38:39] exactly. The other thing I've been trying to do really hard is to offer the content to folks that are just like, and afforded, or don't even know it exists. I've been giving out a bunch of free subscriptions to like, women in product and like the black product managers group and, Latin X VC and things like that.And that's been really helpful. Right? Nathan: [00:38:58] Yeah. That's great. And it, it spreads the, you know, grows the community and everything else as well. Yeah, exactly. when you're looking to, what are you looking to now for growth as far as is it just continually writing or, do you have specific goals in mind and, specific things as you look to, you know, to pass the 50,000 subscriber Mark or go from there?Lenny: [00:39:20] I, I try really hard not to. I think I mentioned this anytime we do anything, that's not just create high quality content that creates value for people. It doesn't do much. So 90% of my thought is always, how do I write great stuff, ongoing and sustainably. And it's really easy to do more work and find more work for myself like in a podcast and write a book and create a course and all the things.And so I'm trying really hard to avoid as much of this as I can so I can stay and create just a really good newsletter. That's hard enough. But the thing. So a couple of things have happened since I started it. One is, as I was launching the paid plan, I was like, man, 15 bucks a month is so much money to ask.What else can I offer people? And I suggested I was going to have a private community that you have access to as a paid member. And eventually I had to do it because I promised it. And that's proven to be the most amazing thing that I've done maybe this year beyond the newsletter, because it's turned into this amazing place of.peer support and help where people are just helping each other all day. And there's about 2,500 people in there and just asking questions, answering questions. And I turned that into its own newsletter with the best conversations from the community each week. And so that ended up providing a lot of people.That's the reason they subscribe. They don't even hear about the newsletter. They just want to access to the community. And so that's proving to be really interesting and valuable. And I will say I'm working on a product management course next year. That's something I've decided to do to see where that goes.Nathan: [00:40:55] But I could see that there being a lot of demand for that. And one thing that's interesting, there is a lot of people talk about a newsletter or like a paid newsletter as the business model, right. Or you can choose to do courses or books or sponsorships or a paid newsletter. And there. separate things and really, I mean, exactly what you're pointing is like, they can, they can, co-exist just fine.You can do a paid newsletter and then do a course for this Lenny: [00:41:23] direction. Yeah. Yeah. Hunter Walker had this great post about how a lot of creators are. They have this one skew, which initially is the newsletter. And then over time you can add more skews, like of course, and I don't know a book or something like that.And so. That makes sense, but it's, yeah, again, it's really easy to do more work and I'm trying really hard, not to just add more work to my plate, but this course felt like just, it felt like the right thing to do next. And so I'm going to experiment with that. Yeah, that makes sense. Nathan: [00:41:52] and I'm, I'll just say I'm a huge fan of it because who I've seen, I've been doing that kind of thing for a long time of selling multiple products, multiple courses, and just seeing how one section of the audience really gravitates towards.Buying one thing. And another section is like, Oh, but we'll happily pay you in aggregate $50,000 or a hundred thousand dollars for content on this, this specific area. And so being the, the multiple skew creator, really lets your audience choose how they want to support you and what they want to learn from you.Lenny: [00:42:23] I'm happy to hear this. Nathan: [00:42:24] Yeah, I think it's a great direction. so let's talk platforms for a little bit. Obviously sub stack is, are you started on medi moved to sub stack, sub stack is growing like crazy. They're getting all kinds of press in the new Yorker, New York times, et cetera. I'd love your thoughts on just where the market is going, you know, and we're, we're kind of back on this topic, but, so I guess where the market's going and then, what are the decisions for you on, you know, When to start on sub stack versus could consider something like a MailChimp or I'd ghost or convert kit.Lenny: [00:43:01] So what's interesting about setup stack is I never would have been doing this with my life, if not for something like a sub stack existing, because I had no intention of ever one charging for a newsletter to even doing like a regular newsletter. I just started with a few posts and. The kind of the, the, the chemistry, that stuff stuck kind of discovered, I think, and went all in on was, let's just make it, it's really easy to create a newsletter and a blog, and then eventually it could charge for it if you want.And so I just followed the, I feel like I was exactly there, like in-store user journey that they mapped out in their initial pitch of like, I just play around, sign up, create a sub stack. Do if you posts it's going well. Okay. Maybe I shouldn't bet on this. Yeah. Maybe I should charge. And so, so we never would have been doing this if not for a platform like that, but in the end, it's not a complicated set of features.And so there's going to be more and more competition. and as, as you will know, and so I don't know what's going to happen there longterm. I will say the fees at scale are very painful and, and so the bet is that they provide. Enough services and benefits and maybe customers that make it worth it.But, and for now I'm just super loyal to them and just really enjoy that the platform is just because it allowed for me to live this life. so, so I'm happy. Nathan: [00:44:24] Yeah. I think from a, you know, both you and I working in product management and growth, and all of that, it's fascinating to look at it from a case study of this is something that plenty of people have tried many times before.Lenny: [00:44:38] Great. Nathan: [00:44:40] Yeah. And I'm configured. We've been working on it for, in, in various farms and for a different market and for a long time and I study it and I'm like, okay, what, what did they get? Right. And it really is that they just made it effortless to go from, I have this one post, this thing that I want to write about to like, Oh, there's a place for it.Oh yeah, of course you can subscribe. Whereas the industry for so long was, Oh, you want to start a newsletter? Like. Let's glue together. 12 different things. Oh, you paid, Oh God paid. Oh man. Okay. You gotta, you gotta set to have so much stuff, you know, Lenny: [00:45:16] even like that first step of like, you want to start a newsletter.Like I wasn't even in that mindset, I was just like, Oh, this is a better place to do a blog because I can capture email addresses. So yeah. So they just made it like a trick, almost that like, Oh, okay. I see where this could go. Nathan: [00:45:29] And it guided you into a six figure business. So I think that's. I mean, that's something that's so important to have like finding a place to start because none of this matters, like people get so obsessed over platform or, you know, any of this, like what's the fees.Exactly. And like, if you never get past a thousand subscribers, which a thousand subscribers is hard, like that is a meaningful bar, you get to that point, you have moment. but if you never get past that, like the platform that you choose. Does not matter. And so we're exactly, you know, as newsletter creators, we often obsess over the wrong decision to start.Whereas the correct decision is, am I going to do this every day for a year to see if I'm, if I like it? Lenny: [00:46:16] Yeah, yeah, exactly. How do I, how do I figure that out as soon as possible and as easily as possible before I overthink all the different variables that come into play. And I totally agree, like in the end, it just, again, comes to, can I create value for people consistently?And then do I enjoy it? That's, that's a really important piece because. Cause like, you're not gonna, you're not gonna last if you're not enjoying it enough, at least, you know, writing is hard. also, so there's not going to be fully enjoying it. Nathan: [00:46:42] Yes. Yep. That makes sense. Okay. So something that I want to talk about a little bit more, is this idea of keeping the newsletters simple.So being in the online marketing space for a long time, I've seen people scale a newsletter or a content business, and they get to the point where it's a little, you know, maybe they're making 200,000 a year and they're like, I should hire an assistant. I should hire an editor. You know, you get some of that help.and then it starts to go from there, right? Maybe they're 500,000 a year, maybe a million a year, and they're starting to be a team. I'd love your thoughts on that because. That's a path that you could take. You could turn this into the definitive, like the definitive forget newsletter, the definitive news source for product management.You know, this could be something, in that way. What, what are your thinking about your approach and keeping it, keeping it simple? Lenny: [00:47:36] Well, I've worked really hard for many years and I know what that's like. And. I feel like I have this opportunity to create a pretty balanced lifestyle where I don't need to work 80 hours a week.And, and you quickly get there by just doing more and trying to add to it and accelerated and build more. And so I'm trying really hard not to do that. And I feel like there's like, I could just do exactly this for a long time. And when it feels like it will keep growing, even if I do nothing. And I feel like I could make more just keeping it on my own thing.Not hiring anyone. Full-time not trying to, you know, add more business units to it. Maybe it's wrong. But yeah, most of it comes from just like a, I could easily become a workaholic again and do a lot more work. And I'm trying hard to avoid that as much as I can while delivering consistent value. Nathan: [00:48:31] Yeah. I think that's really important that you touched on of.But just a little bit of the actual take home of, you can keep driving that top line revenue nber, but this isn't a, in this right now, a traditional startup. You're not trying to make it that. And so actually the profit is what really matters. And so if we fast forward and we're like, okay, this business is going to be.At $3 million a year, X nber of years from now. And it's going to have in order to hit that revenue nber and provide that value for that many people, it's going to need a team of 10 people. It's going to, you know, it has all of these needs and before you know it, you're managing payroll again and yeah.All this stuff. and that's like, I think a lot of people get to that position, chasing the growth and then look back and say like, Oh man, I liked it when it was simple, when it was recurring revenue, serving a single audience in just showing up in a consistent way. Lenny: [00:49:34] Yeah, that's, that's my current philosophy, but I will say I'm, I have like a designer I'm contracting with, to like kind of level up that feel.I have a, a PM. I work with that, like hourly, where she helps curate this weekly newsletter. So there's a few folks that are helping out and there's a community events friend that's helping out run events and things like that. So I think what I'm trying to do is yeah, just keep it really simple. Maybe that's the philosophy.Just keep it simple. And you ended up making more and being happier. And so far it's working out, we'll see where it all goes. Nathan: [00:50:08] Yeah. I have a good friend, Josh Kaufman, who wrote the book, the personal MBA, and he's done this really well of sticking to a really simple business. He's gotten to the point.He's always looked for channels where someone else is handling customer support. So like he likes to sell on Amazon audible and stuff like that. So he's as the author, he's one step removed. And that's just one example. If he's said, no, I want a simple business. and he, you know, that doesn't mean you can't work with a lot of freelancers, and have a team he loves to employ editors because they make his writing so much better.And that's actually something that I'd recommend for anyone writing a newsletter where you want the content really good. Having someone that you pay to go. Yeah, I see where you're going with this. What is going on in this section, like, you know, rework that yeah. Lenny: [00:50:59] If you have anyone you can recommend, that would be awesome.but I will say there's like, I, maybe I'm just like, I don't, I'm not in the, like the ambitious phase of my life. I feel like it's totally cool to be super ambitious and try to make something huge also. And maybe there's a venture scale return somewhere in this space, as a creator. And I think it's totally fine to try.I just, I think for me personally, I'm just, I'm happy just making a meaningful income and not trying to turn this into like a billion dollar enterprise. Nathan: [00:51:31] One other thing on that is wherever, let's say at some point down the road two years from now, three years from now that in that list of the 50 startup ideas, right.Maybe one of them does start to stand out and then you're like, I think I want to pursue this. then you have this list of. 30 40, a hundred thousand, maybe it's 200,000 people by then who you're like you have your own audience and your own platform to launch to as well as all of these connections.Lenny: [00:52:01] Super true. Yeah. I could always turn in some new and I could just, okay. Newsletter is done moving off. Nathan: [00:52:07] Well, you don't even have to necessarily give up the newsletter. Yeah, Lenny: [00:52:10] that's true. If I can find a more efficient way of doing it every week while running a company, maybe. Right. Nathan: [00:52:15] what are some. Yeah.What are some interesting doors that have opened from writing the newsletter or opportunities that have come up where people that you've met that came about purely because you're Twitter famous now, certain circle, Lenny: [00:52:31] speaking of Twitter, like there's this amazing, super power that gets unlocked. Once you have enough followers, where any question you have, you could just ask it and you get all these amazing answers from people that are just.You know, very curious to see what everyone else says and they share their insight. So I find that whenever I focus on a topic and I want to get a more complete picture of how people are thinking about it, I just ask the question on Twitter and it turns into this really amazing resource. So I try to leverage that more and more because I find it it's like helpful to everybody else.Also. It's not just, Oh, here's a bunch of answers I'm going to, I'm going to take it all from you. It's like now this public thread of all these interesting. answers to a really interesting question. That's one amazing thing that I didn't see coming. And then two, I also angel invest and I find like 80% of founders are subscribed to the newsletter or have heard of it.And. As, as we know in investing, it's it, it's on the investor to get into great deals now because there's so many VCs and angels out there. And so the more you people can see the value you can provide the easier it is for you to get into the deal. And now they can see, Oh, he's smart about these things.We should let them invest. And so it's been really helpful letting me get into it early. Interesting startup deals. Nathan: [00:53:45] Yeah. That makes sense. On the note of Twitter, what are some of the things that have worked as specifically grow your Twitter Lenny: [00:53:51] following. It's exactly the same thing. Just providing value for people.Anytime I think of something either from a post that I've done or just that isn't enough for posts. I just find a way to share it very succinctly on Twitter. Like, you know, how to do performance reviews or, or even just like smarizing a post that's long into a Twitter thread. it's just always that just provide value to people and the vole will retweet it.They'll like it and all those things, and it just kinda builds on itself. Nathan: [00:54:20] That makes sense. And I mean, it just goes back to an everything that you're doing of there aren't, even though we work in growth and startups, There aren't really growth hacks in the same way. It's like, it's show up consistently.That's the hack show consistently and high quality. Lenny: [00:54:36] Yeah. Consistent quality. Exactly. Just provide consistent value to people. I know for like morning brew, a referrals program worked really well and there's like, you know, cases where something like that's not pure content helped significantly, but I find in the end, if your newsletter just isn't growing significantly, I would just think about how do I provide more value to the readers.Again, and again and again, and it's not going to happen overnight. And that seems to work. Nathan: [00:55:01] Yeah. Okay. Last question I realized, I was thinking about on the pricing side, you have this, this split that you talked about between individuals paying for it and companies paying for it. And I think that's relatively new in the newsletter space of a company like a B2B newsletter.Yeah, exactly. And so if someone was starting out and they're trying to hone in on their topic and maybe there's an option for them to write. Something that could be expensed. how would you think about that? Do you think that's happening a lot? Is that important or does it matter? Lenny: [00:55:33] I don't actually know what percentage of my newsletter is expensed.If I had to guess it's like 20% expensive, something like that. And so that's not like a game changer and it's hard to like, if, if you listened to my advice of stick to things you're interested in, it's hard to like Frankenstein on. Oh, I'm also going to have this thing that just happens to be interesting for companies.But, but it's, it's a helpful thing. And I've tried to do a little bit of proactive B2B kind of sales, and it doesn't really do much. I find that it just, I have to wait for people to come to me and ask for like both discounts for their company. And that works well. I also find VCs are offering it as a perk to their portfolio companies occasionally, but all that just comes to me anytime I pitched them on it, doesn't give anywhere.So, but it's an interesting new trend and, I don't know where it's going to go. I don't know if it'll ever be like 50% of, of my readers. but yeah, if obviously, if you can create value for a company, they have more money. Right. And so you'll have some sales there. Yeah. Nathan: [00:56:34] On that note, it just made me think of advice I've given in the past.when people are trying to hone in on a topic and it's like, well, if you're trying to make money yourself through, through teaching, right. Which the newsletter, of course, any of that. W we're teaching in one form or another. If you're trying to make money yourself, then teach a skill that makes money to people who have money.And so we're not talking about, you know, knitting to teenagers, right? We're talking about product management, growth strategies to startup founders, PMs companies who have money. And so it's probably not like canvas be expensed or not that you're thinking about. It's. Okay. Am I delivering value, a level of value that people can, are now living with, you know, and it, and it will level up their career.Lenny: [00:57:22] Yeah. Those are definitely the easiest newsletters to monetize. There's also just like helping make money directly. Like there's like Bitcoin newsletters and, there's one around like a distressed asset investing that does it really well. But then there's also just like, if you look at the subset leader board, like the first two are all just news, like politics analysis, like a really unique perspective on politics.So you can definitely make money just through news and analysis. And also just like entertainment, like the browser is this awesome newsletter. It's just beautiful pieces of writing everyday and people pay for that. So there's a lot of different approaches. Nathan: [00:57:57] Do you have any newsletters beyond what you've just mentioned that you particularly love?Lenny: [00:58:02] I always worried about answering this question cause I have so many newsletter friends in that one. I always worry. They're going to get upset at me. You single somebody out. Exactly. So how about, I'm going to tweet my favorites and then go follow, go. Find me on Twitter. Nathan: [00:58:17] That sounds good. Well, that's a good place to wrap up.So on that note, where should people follow you on Twitter and then subscribe to the newsletter? Lenny: [00:58:23] LennysNewsletter.com, which just redirects to my Substack and then just Lenny-san, S-A-N, @lennysan on Twitter. Nathan: [00:58:32] Perfect. Well, thanks so much for joining me. This is a really funny conversation and, we'll, we'll talk soon.Lenny: [00:58:37] Thanks for having me.

In 2019, Lenny Rachitsky left his job at one of the planet's most promising startups.Shortly after leaving Airbnb, he started to write down everything he had learned about product, growth, and management.A few of his essays nearly broke the internet and he quickly built up an enthusiastic reader base of people excited to learn from his experience and expertise. His newsletter now consistently ranks as a top-20 Substack publication with tens of thousands of loyal readers.On this private call for Foster members, Lenny revealed the lessons he's learned writing long-form essays on the stuff he knows best. He shared advice for anybody thinking about turning their expertise into timeless writing that lives on the internet.

Adi Zief-Balteriski is a behavioral science expert in the field of community, technology and consumer behavior. She is a researcher in the field of well-being and holds a Ph.D. in clinical psychology, L.L.B in Law and B.A in Business and IT. Adi states that making a positive impact on people's lives has been her life-long passion. She spent the past few years building products to increase people's well-being and positive experiences. She has been advising startups in well-being sphere and recently founded her first startup MyKumbaya. During the episode, we mentioned these: Adi's start up with Chen Levanon - www.mykumbaya.com Adi's email for further questions - Adi@mykumbaya.com Megagon Labs - megagon.ai Adi recommends following Lenny Rachitsky on LinkedIn: linkedin.com/in/lennyrachitsky ; medium.com/@lennysan Adi also recommends following Nir Eyal and reading his book, 'Hooked': linkedin.com/in/nireyal Book: https://www.amazon.com/Hooked-How-Build-Habit-Forming-Products-ebook/dp/B00LMGLXTS EPISODE IS IN ENGLISH Episode music: "Dream Catcher",  Kevin MacLeod (incompetech.com). Licensed under Creative Commons: By Attribution 3.0. http://creativecommons.org/licenses/by/3.0/ --- Send in a voice message: https://anchor.fm/macademia/message