In Episode #102, we explore the super angel on speed, small teams, product management, and the S.P.A.D.E. decision framework. We’re joined by prolific angel investor Gokul Rajaram. We cover the product analyst role, and focusing on controllable inputs, and editing vs. managing a product. “The best product leaders coach people across the company, not just in their team, and help develop them into the future leaders of the company.” – Gokul RajaramEPISODE GUIDE (LINKS, QUOTES, NOTES, AND BOOKS MENTIONED)https://www.danielscrivner.com/notes/angel-investor-speed-small-teams-product-management-decision-making-gokul-rajaram-spotlight-show-notesFULL TEXT TRANSCRIPThttps://www.danielscrivner.com/notes/angel-investor-speed-small-teams-product-management-decision-making-gokul-rajaram-spotlight-transcriptCHAPTERSThis episode is our definitive guide to product management in small, speedy teams. In it we cover: (00:00:00) – Introduction (00:02:26) – Gokul’s background in product management (00:06:58) – Applying a computer science background to product management (00:10:26) – What great product vision looks like (00:16:32) – The product analyst role (00:23:11) – Focusing on controllable inputs (00:26:07) – Experiment design (00:34:54) – Editing vs. managing a product (00:42:50) – S.P.A.D.E. decision making (00:55:18) – Speed in product creation ABOUT GOKUL RAJARAMGokul Rajaram is part of a new wave of solo capitalists, like Elad Gil and Lachy Groom, that play an outsized role in funding and helping many of the world's best startups. As Gokul says in this interview, his goal is for every founder he backs to say that he's the most helpful investor on the cap table. And if there is another thing that Gokul is known for, it's his expertise around product management and decision making, including the Spade framework he created at Square for making transparent decisions at the highest levels. Spade is now used by many of the world's best startups for large, important, and strategic decisions that need to be made transparently so the whole company understands why the decision was made.💌 FREE NEWSLETTERhttps://www.outlieracademy.com/newsletter🎙 LISTEN ONiTunes: https://podcasts.apple.com/us/podcast/outlier-academy/id1523851182Spotify: https://open.spotify.com/show/58edVNgqaPNaCSGSxM6pef?si=88f37a5d20434775Overcast: https://overcast.fm/itunes1523851182ABOUT OUTLIER ACADEMYLearn timeless lessons on work and life from iconic founders, world-renown investors, and bestselling authors. Outlier Academy is the forever school for those chasing greatness. Past guests include Gokul Rajaram of DoorDash, Scott Belsky of Benchmark and Adobe, Joey Krug of Pantera Capital, Mark Sisson of Primal Kitchen, Luke Gromen of The Forest for the Trees, and Brian Scudamore of 1-800-GOT-JUNK.Website: https://www.outlieracademy.comTwitter: https://www.twitter.com/outlieracademyABOUT DANIEL SCRIVNEROutlier Academy is hosted by Daniel Scrivner. Over the last 15 years, Daniel has led design teams at Square and Apple, turned around a $3M+ ARR SaaS business, and invested in more than 100 companies. He launched Outlier Academy in 2020 to learn from the world’s best founders, investors, authors, and peak performance experts.Website: https://www.danielscrivner.comTwitter: https://www.twitter.com/danielscrivner Learn more about your ad choices. Visit megaphone.fm/adchoices

Listen to a trailer for our next Spotlight episode featuring Gokul Rajaram. Learn more about your ad choices. Visit megaphone.fm/adchoices

In Episode #56, we deconstruct Vivek Sodera's peak performance playbook—from his favorite book to the tiny habit that's had the biggest impact on his life. Vivek is the Co-Founder of Superhuman. We cover identifying great founders, opportunities for growth, and having accountability partners for health.“I'm trying to optimize for happiness. I'm not trying to optimize for ego.” – Vivek SoderaEPISODE GUIDE (LINKS, QUOTES, NOTES, AND BOOKS MENTIONED)https://www.danielscrivner.com/notes/vivek-sodera2-outlier-academy-show-notes FULL TEXT TRANSCRIPThttps://www.danielscrivner.com/notes/vivek-sodera-outlier-academy-transcript CHAPTERSIn this episode, we deconstruct Vivek Sodera's peak performance playbook—from his favorite book to the tiny habit that's had the biggest impact on his life. In it we cover: (00:00:00) – Introduction (00:00:30) – What Vivek looks for in founders when he invests (00:04:50) – Identifying winners and predicting the future (00:08:46) – Having a health accountability partner (00:11:06) – Learning to say “no” (00:14:12) – Relying on Fitbit, Levels, and Superhuman (00:16:26) – The constant opportunity for growth and building relationships (00:23:40) – Failed startups and positively impact the lives of others ABOUT VIVEK SODERAVivek Sodera is Co-Founder of Superhuman, a platform striving to be the fastest email experience in the world. He is also an investor, with a portfolio of companies including Framework, UtilizeCore, Rewatch, Bunches, and Playbook. He previously co-founded Airseed and LiveRamp, though he started his career in nuclear engineering.💌 FREE NEWSLETTERhttps://www.outlieracademy.com/newsletter🎙 LISTEN ONiTunes: https://podcasts.apple.com/us/podcast/outlier-academy/id1523851182Spotify: https://open.spotify.com/show/58edVNgqaPNaCSGSxM6pef?si=88f37a5d20434775Overcast: https://overcast.fm/itunes1523851182ABOUT OUTLIER ACADEMYLearn timeless lessons on work and life from iconic founders, world-renown investors, and bestselling authors. Outlier Academy is the forever school for those chasing greatness. Past guests include Gokul Rajaram of DoorDash, Scott Belsky of Benchmark and Adobe, Joey Krug of Pantera Capital, Mark Sisson of Primal Kitchen, Luke Gromen of The Forest for the Trees, and Brian Scudamore of 1-800-GOT-JUNK.Website: https://www.outlieracademy.comTwitter: https://www.twitter.com/outlieracademyABOUT DANIEL SCRIVNEROutlier Academy is hosted by Daniel Scrivner. Over the last 15 years, Daniel has led design teams at Square and Apple, turned around a $3M+ ARR SaaS business, and invested in more than 100 companies. He launched Outlier Academy in 2020 to learn from the world’s best founders, investors, authors, and peak performance experts.Website: https://www.danielscrivner.comTwitter: https://www.twitter.com/danielscrivner Learn more about your ad choices. Visit megaphone.fm/adchoices

In this Replay episode, we explore building the world's first crypto hedge fund and growing to $6B in AUM. We’re joined by Joey Krug, Co-Chief Investment Officer of Pantera Capital. We cover lessons from investing in volatile markets, DeFi and the future of prediction markets, and branding in crypto.“When you're investing and you have a position that you think you have conviction in, where you think it's very high odds that you're right, take a big swing at it.” – Joey KrugEPISODE GUIDE (LINKS, QUOTES, NOTES, AND BOOKS MENTIONED)https://www.danielscrivner.com/notes/building-6b-hedge-fund-crypto-pantera-capital-joey-krug-ig-show-notes FULL TEXT TRANSCRIPThttps://www.danielscrivner.com/notes/building-6b-hedge-fund-crypto-pantera-capital-joey-krug-ig-transcript CHAPTERSThis episode is our definitive guide to building the world's first crypto hedge fund. In it we cover: (00:00:00) – Introduction (00:02:35) – Joey's daily work at Pantera, Augur, and Eco (00:04:35) – Joey's start in mining Bitcoin (00:09:28) – Joining Pantera and investing (00:17:18) – Lessons learned as an investor in volatile markets (00:20:13) – Pantera's active trading and early stage venture bets (00:23:41) – Perspectives on risk (00:29:24) – On scaling Ethereum (00:31:10) – DeFi and the future of prediction markets (00:35:35) – A peek into Eco (00:37:29) – Branding in crypto (00:41:20) – Technical analysis in trading ABOUT PANTERA CAPITALPantera Capital was founded by Dan Morehead in 2013 and became the first institutional investment manager in the Crypto space. Today, Pantera has amassed over $6 billion in capital, alongside absolutely eye-popping returns. Pantera invests in new Crypto, DeFi and Web 3 protocols and projects, and they also manage a liquid more mature Crypto portfolio. They live in a very interesting position within the space. As the co-founder of multiple high-profile projects, as well as the co-CIO of over $6 billion in assets.For more on Pantera, visit panteracapital.com. I also highly recommend subscribing to their monthly newsletter where they share their commentary and thoughts on the broader Crypto market. I've been a subscriber for years, and I've always really enjoyed reading through it.💌 FREE NEWSLETTERhttps://www.outlieracademy.com/newsletter🎙 LISTEN ONiTunes: https://podcasts.apple.com/us/podcast/outlier-academy/id1523851182Spotify: https://open.spotify.com/show/58edVNgqaPNaCSGSxM6pef?si=88f37a5d20434775Overcast: https://overcast.fm/itunes1523851182ABOUT OUTLIER ACADEMYLearn timeless lessons on work and life from iconic founders, world-renown investors, and bestselling authors. Outlier Academy is the forever school for those chasing greatness. Past guests include Gokul Rajaram of DoorDash, Scott Belsky of Benchmark and Adobe, Joey Krug of Pantera Capital, Mark Sisson of Primal Kitchen, Luke Gromen of The Forest for the Trees, and Brian Scudamore of 1-800-GOT-JUNK.Website: https://www.outlieracademy.comTwitter: https://www.twitter.com/outlieracademyABOUT DANIEL SCRIVNEROutlier Academy is hosted by Daniel Scrivner. Over the last 15 years, Daniel has led design teams at Square and Apple, turned around a $3M+ ARR SaaS business, and invested in more than 100 companies. He launched Outlier Academy in 2020 to learn from the world’s best founders, investors, authors, and peak performance experts.Website: https://www.danielscrivner.comTwitter: https://www.twitter.com/danielscrivner Learn more about your ad choices. Visit megaphone.fm/adchoices

In Episode #101, we deconstruct Alex Rubalcava's peak performance playbook—from his favorite book to the tiny habit that's had the biggest impact on his life. Alex Rubalcava is Partner at Stage Venture Partners. We cover the coming energy transition and advice for founders and investors.“No one in the world has an urgent problem that will get solved by investing in some random guy's venture capital fund.” – Alex RubalcavaEPISODE GUIDE (LINKS, QUOTES, NOTES, AND BOOKS MENTIONED)https://www.danielscrivner.com/notes/alex-rubalcava-stage-venture-partners-playbook-show-notes FULL TEXT TRANSCRIPThttps://www.danielscrivner.com/notes/stage-venture-partners-alex-rubalcava-playbook-transcript CHAPTERSIn this episode, we deconstruct Alex Rubalcava’s peak performance playbook—from his favorite book to the tiny habit that's had the biggest impact on his life. In it we cover: (00:00:00) – Introduction (00:01:53) – Alex’s superpowers in investing (00:03:07) – Advice for founders (00:05:03) – Learning from Berkshire Hathaway and investment books (00:09:17) – The massive energy transition underway (00:14:24) – Advice for new investors (00:16:54) – Planning and long term success ABOUT ALEX RUBALCAVAAlex Rubalcava is the Founder and Managing Partner of Stage Venture Partners. Stage VP invests hyper early, typically pre-seed and seed, into deep technology companies across four core verticals, which includes space technology, industrial applications, healthcare and life sciences, and eCommerce tooling. What fascinated me about Alex and Stage Venture Partners is the incredibly unique approach of investing early into very difficult technological problems with a proven ability to help shepherd these companies from seed to Series A and beyond.In this episode, we cover Alex's investing superpower, how he manages his time, why he loves the book The Gorilla Game, the advice he gives founders again and again and again, and so much more.💌 FREE NEWSLETTERhttps://www.outlieracademy.com/newsletter🎙 LISTEN ONiTunes: https://podcasts.apple.com/us/podcast/outlier-academy/id1523851182Spotify: https://open.spotify.com/show/58edVNgqaPNaCSGSxM6pef?si=88f37a5d20434775Overcast: https://overcast.fm/itunes1523851182ABOUT OUTLIER ACADEMYLearn timeless lessons on work and life from iconic founders, world-renown investors, and bestselling authors. Outlier Academy is the forever school for those chasing greatness. Past guests include Gokul Rajaram of DoorDash, Scott Belsky of Benchmark and Adobe, Joey Krug of Pantera Capital, Mark Sisson of Primal Kitchen, Luke Gromen of The Forest for the Trees, and Brian Scudamore of 1-800-GOT-JUNK.Website: https://www.outlieracademy.comTwitter: https://www.twitter.com/outlieracademyABOUT DANIEL SCRIVNEROutlier Academy is hosted by Daniel Scrivner. Over the last 15 years, Daniel has led design teams at Square and Apple, turned around a $3M+ ARR SaaS business, and invested in more than 100 companies. He launched Outlier Academy in 2020 to learn from the world’s best founders, investors, authors, and peak performance experts.Website: https://www.danielscrivner.comTwitter: https://www.twitter.com/danielscrivner Learn more about your ad choices. Visit megaphone.fm/adchoices

Listen to one of our favorite moments from tomorrow’s 20 Minute Playbook episode featuring Alex Rubalcava of Stage Venture Partners. In it, Alex shares his favorite books, tools, habits, and more. Learn more about your ad choices. Visit megaphone.fm/adchoices

In Episode #100, we explore the power of virtual cards, building two-sided products, and selling into enterprises. We’re joined by Andrew Jamison, co-founder and CEO of Extend. We cover starting from scratch in the payment space, building software in a startup environment, and the differences between working in a large corporation and in a startup.“Nothing good really happens with cash.” – Andrew JamisonEPISODE GUIDE (LINKS, QUOTES, NOTES, AND BOOKS MENTIONED)https://www.danielscrivner.com/notes/extend-power-of-virtual-cards-andrew-jamison-spotlight-show-notes FULL TEXT TRANSCRIPThttps://www.danielscrivner.com/notes/extend-power-of-virtual-cards-andrew-jamison-spotlight-transcript CHAPTERSThis episode is our definitive guide to virtual cards and selling into enterprises. In it we cover: (00:00:00) – Introduction (00:02:00) – Andrew’s international background and work at American Express (00:07:34) – What credit cards unlock in a global, interconnected world (00:12:39) – How Extend works (00:16:08) – Starting from scratch in the payment space (00:19:25) – The first four years of Extend (00:24:17) – How virtual cards benefit small businesses (00:34:39) – The decision not to be a card issuer (00:41:10) – Building software in a startup environment (00:48:35) – The differences between working in a large corporation and in a startup (00:56:07) – The entrepreneurial journey ABOUT EXTENDExtend is the world's first virtual card platform that works with every card issuer. Which might make you think, what is a virtual card? Virtual cards effectively tokenize a physical card making it easy to create any number of digital cards, each with advanced controls around everything from spending to geolocation, to merchant gating, which enables very powerful uses for a massive number of industries. From helping lawyers and law firms clearly break out expenses by cases and attorneys, to powering food delivery companies like GrubHub and DoorDash so couriers can easily pay for the food they're picking up, to helping travel companies hold thousands of hotel rooms all tied to individual virtual cards.💌 FREE NEWSLETTERhttps://www.outlieracademy.com/newsletter🎙 LISTEN ONiTunes: https://podcasts.apple.com/us/podcast/outlier-academy/id1523851182Spotify: https://open.spotify.com/show/58edVNgqaPNaCSGSxM6pef?si=88f37a5d20434775Overcast: https://overcast.fm/itunes1523851182ABOUT OUTLIER ACADEMYLearn timeless lessons on work and life from iconic founders, world-renown investors, and bestselling authors. Outlier Academy is the forever school for those chasing greatness. Past guests include Gokul Rajaram of DoorDash, Scott Belsky of Benchmark and Adobe, Joey Krug of Pantera Capital, Mark Sisson of Primal Kitchen, Luke Gromen of The Forest for the Trees, and Brian Scudamore of 1-800-GOT-JUNK.Website: https://www.outlieracademy.comTwitter: https://www.twitter.com/outlieracademyABOUT DANIEL SCRIVNEROutlier Academy is hosted by Daniel Scrivner. Over the last 15 years, Daniel has led design teams at Square and Apple, turned around a $3M+ ARR SaaS business, and invested in more than 100 companies. He launched Outlier Academy in 2020 to learn from the world’s best founders, investors, authors, and peak performance experts.Website: https://www.danielscrivner.comTwitter: https://www.twitter.com/danielscrivner Learn more about your ad choices. Visit megaphone.fm/adchoices

Listen to a trailer for our next Spotlight episode featuring Extend with Andrew Jamison. Learn more about your ad choices. Visit megaphone.fm/adchoices

Eric Markowitz shares his journey from being an award-winning journalist to the Director of Research at Worm Capital—leading all of the research that informs Worm’s concentrated, long-only, technological disruption investment focus. Eric shares why investing is all about making good calculated bets, the important of slowing down the research process, how he avoids making behavioral mistakes, and so much more.“I think the lesson learned is there’s so much value to patience in this business. That just slowing down not only the research process, but the actual allocation and trading process, is immensely valuable. Some of the greatest investors just do nothing, right? That is such a hard thing to conceptualize—especially in a culture that values action and values doing things. Most of the time, really the best answer is to do nothing.” — Eric MarkowitzEPISODE GUIDE (LINKS, QUOTES, NOTES, AND BOOKS MENTIONED)https://www.danielscrivner.com/notes/eric-markowitz-worm-capital-playbook-show-notes FULL TEXT TRANSCRIPThttps://www.danielscrivner.com/notes/eric-markowitz-worm-capital-playbook-transcript CHAPTERS (00:00:00) - Introduction (00:01:56) – Eric’s Path from Journalist to Director of Research (00:07:57) – Why Investing is About Making Good Calculated Bets (00:09:47) – Worm’s Two-Step Research Process (00:13:21) – The Importance of Slowing Down the Research Process (00:15:36) – Guardrails and Keeping Bad Information Out of the Research Process (00:19:48) – Worm’s Behavioral Advantages in Investing (00:23:44) – Eric’s Recent Obsessions: The Future of Robotics (00:26:54) – Eric Markowitz’s Favorite Books ABOUT ERIC MARKOWITZEric Markowitz is the Director of Research at Worm Capital. Worm runs a concentrated long-only strategy and invests in technological disruption. They call themselves "value investors focused on the future” and are drawn toward messy, complicated sectors of the market that are difficult to understand—and even more difficult to accurately price.Before joining Worm Capital, Eric worked as an award-winning investigative business journalist and wrote from Inc., The New Yorker, and Newsweek. As the Director of Research, Eric leads all of Worm’s research efforts including mapping out new industries, understanding new technologies, and breaking down investment targets to understand the inputs and outputs that drive their business.Twitter | Worm Capital | The Nightcrawler💌 FREE NEWSLETTERhttps://www.outlieracademy.com/newsletter🎙 LISTEN ONiTunes: https://podcasts.apple.com/us/podcast/outlier-academy/id1523851182Spotify: https://open.spotify.com/show/58edVNgqaPNaCSGSxM6pef?si=88f37a5d20434775Overcast: https://overcast.fm/itunes1523851182ABOUT OUTLIER ACADEMYLearn timeless lessons on work and life from iconic founders, world-renown investors, and bestselling authors. Outlier Academy is the forever school for those chasing greatness. Past guests include Gokul Rajaram of DoorDash, Scott Belsky of Benchmark and Adobe, Joey Krug of Pantera Capital, Mark Sisson of Primal Kitchen, Luke Gromen of The Forest for the Trees, and Brian Scudamore of 1-800-GOT-JUNK.Website: https://www.outlieracademy.comTwitter: https://www.twitter.com/outlieracademyABOUT DANIEL SCRIVNEROutlier Academy is hosted by Daniel Scrivner. Over the last 15 years, Daniel has led design teams at Square and Apple, turned around a $3M+ ARR SaaS business, and invested in more than 100 companies. He launched Outlier Academy in 2020 to learn from the world’s best founders, investors, authors, and peak performance experts.Website: https://www.danielscrivner.comTwitter: https://www.twitter.com/danielscrivner Learn more about your ad choices. Visit megaphone.fm/adchoices

Listen to a trailer for our next Playbook episode featuring Eric Markowitz of Worm Capit Learn more about your ad choices. Visit megaphone.fm/adchoices