The Peel with Turner Novak

Jason Calacanis is the host of the All-In Podcast, This Week in Startups, co-founder of the Launch Accelerator, and the “3rd or 4th investor in uber”.We go inside the origins of All-In, how they decide what to talk about each week, and if Jason thinks it helped swing the election.We also talk lesson from starting 7 media companies over the past three decades, what he's learned from studying the world's best interviewers, joining Sequoia’s first scout program, his investing strategy at Launch, the story of being the “3rd or 4th investor in Uber", what people underestimate about Elon, and what it was like inside the Twitter buyout in 2022.Thank you to Austin Petersmith for helping brainstorming topics for the conversation.Thanks to Numeral for supporting this episode. It’s the end-to-end platform for sales tax and compliance. Try it here: ⁠https://www.numeral.com⁠Timestamps:(3:34) Interviewing lessons from Oprah, Charlie Rose(6:48) How to ask good questions(12:20) Jason’s favorite upcoming podcasters(17:57) Starting 7 media companies(22:50) How he'd start a new media company today(27:56) In-person experiences, “Bang Bang” in Japan(32:44) Vinyl bars, smartphones, mental health(38:41) Origin of the All-In Podcast(42:58) All-In’s influence on the 2024 Election(46:58) Why All-In got so political(52:35) Media lessons from Trump(55:01) Joining Sequoia’s very first scout program(57:55) Jason’s VC investing strategy(1:03:55) How Launch competes with other accelerators(1:08:46) Fundraising is a numbers game(1:13:06) Investing in Uber and Robinhood Seed rounds(1:18:31) Origin of “3rd or 4th investor in Uber” meme(1:20:57) How Jason got the first Model S(1:26:19) What people underestimate about Elon(1:27:37) Inside the Twitter takeover(1:31:44) Career advice for young people(1:35:22) Jason’s experience taking GLP-1’s(1:40:05) How All-in picks topics each weekReferencedHowie: ⁠https://howie.com/⁠All-In Podcast: ⁠https://allin.com/⁠Bret Easton Ellis (Podcast): ⁠https://www.breteastonellis.com/podcast⁠Red Scare (Podcast): ⁠https://en.wikipedia.org/wiki/Red_Scare_(podcast)⁠Preet Berrara (Podcast): ⁠https://cafe.com/stay-tuned-podcast/⁠Adam Friedland Show: ⁠https://www.youtube.com/c/TheAdamFriedlandShow⁠The Insider (Movie): ⁠https://www.imdb.com/title/tt0140352/⁠Launch: ⁠https://www.launch.co/⁠Ro: ⁠https://ro.co/⁠Follow JasonTwitter: ⁠https://twitter.com/Jason⁠LinkedIn: ⁠https://www.linkedin.com/in/jasoncalacanis/⁠Follow TurnerTwitter: ⁠https://twitter.com/TurnerNovak⁠LinkedIn: ⁠https://www.linkedin.com/in/turnernovak⁠Subscribe to my newsletter to get every episode + the transcript in your inbox every week: ⁠https://www.thespl.it

Steven Fabre is the Co-founder and CEO of Liveblocks.Liveblocks builds ready-made AI copilots and collaboration for your product, and Steven is one of my smartest friends on how people are actually using AI on a day-to-day basis.We talk about what most people get wrong when trying to build AI-native software, how to treat it as more than just a copilot that sits on top of your product, and what he’s learned about how large enterprises are actually buying and using AI right now.We also talk through Liveblocks journey of evolving from real-time human collaboration components into one that also incorporates AI, what he’s learned going from a designer to a CEO, and how he rebuilt the company after his co-founder stepped away.Thank you to Numeral for supporting this episode. It’s the end-to-end platform for sales tax and compliance. Try it here: ⁠https://www.numeral.com⁠Timestamps:(2:17) Liveblocks: Infrastructure for people + AI(6:08) Wrong ways to add AI to software(8:05) Why humans and AI must collaborate(12:35) How AI will change software UI(18:58) AI search optimization(26:20) How to get #1 on Product Hunt(32:33) Liveblocks 1.0 to 3.0 evolution(36:40) Why collaboration software is so hard(38:38) How customers use Liveblocks(42:36) Hiring a coach to get better at sales(47:07) Steven’s biggest enterprise sales mistakes(50:28) How AI changes GTM and funding milestones(57:57) Going from a designer to a CEO(1:01:06) How Liveblocks first started(1:04:56) Importance of design in company building(1:06:51) Learning to become a CEO(1:12:29) When his co-founder left 5 years in(1:15:49) Becoming stronger hiring a new Head of Engineering(1:22:10) Remote culture: what doesn’t work(1:24:08) Remote culture: what does work(1:26:47) Importance of autonomy on remote teams(1:28:05) Most underrated basketball players(1:33:38) ACL injury that kickstarted his first businessReferencedLiveblocks: https://liveblocks.io/Careers at Liveblocks: https://join.team/liveblocksFollow StevenTwitter: https://x.com/stevenfabreLinkedIn: https://www.linkedin.com/in/steven-fabre-5510bb38Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Zaid Rahman is the Co-founder and CEO of Flex.Flex is the AI native private bank for high net worth middle market business owners, headlined by it’s 60-day interest free credit card for businesses.Flex just announced their $60 million Series B, as well as their new consumer product, Flex Elite, which pits it head-to-head against Amex for the consumer spending of some of the wealthiest people in America. It's products now spans from when a business owner first generates revenue, all the way to when they spend that cash personally.This conversation goes inside how the company scaled from zero to a $70 million revenue run rate in two years, and everything Zaid learned along the way.Thank you to Eric Bahn at Hustle Fund, Jeff Morris Jr. at Chapter One, Andrew Ziperski at General Catalyst, and Jared Thomas and Ewan Steel at Flex for helping brainstorming topics for the conversation.Timestamps:(1:44) Raising $60m to fix business finance(3:23) Flex Elite: Personal + Business banking(4:48) Jumbo shrimps: powering 40% of US payroll(9:16) The forgotten mid market business(14:01) “Flex fuels ambition”(16:08) How to serve entrepreneurs in middle America(22:58) Flex’s 5-pillar product suite(27:12) Starting Flex to help construction companies(31:51) Using AI to lend to mid-market customers(40:22) Power of multi-product in fintech(43:53) Zero to $3B in volume in 18 months(44:43) Raising a bear market Series A in 2023(51:00) How referrals landed their first big customers(55:07) Flex’s playbook for 85% organic growth(1:01:15) Dissecting various accents(1:04:22) Building a quiet luxury brand(1:09:33) Importance of customer happiness(1:12:43) Why CEO’s should be the top sales person(1:13:58) Building lots of in-house software(1:24:33) PMF is like operating a popular restaurant(1:30:49) How to raise a debt facility(1:34:48) Recruiting is so crucial for startups(1:39:00) Why VC’s hate lending businesses(1:45:14) Underserved vs Underbanked in fintech(1:48:02) Why business owners want personal + business banking(1:54:49) Acquiring Maza, leaning in to M&A(2:02:53) Most fintech companies look the same(2:08:35) Founder group therapy with Eric at Hustle Fund(2:11:50) The Thiel Fellowship’s 10% unicorn hit rate(2:15:52) Lesson from the ruler of Dubai(2:19:24) Building Flex’s risk underwriting engine(2:26:58) Flex’s AI opportunityReferencedTry Flex: https://www.flex.oneCareers at Flex: https://jobs.lever.co/Flex/Basel III https://en.wikipedia.org/wiki/Basel_IIILinguistic TikTok account: https://www.tiktok.com/@zaydupreeLazy luxury: most worn shoes on private jets: https://www.wsj.com/style/fashion/lazy-luxury-sneakers-are-these-the-most-worn-shoes-on-private-jets-7801be30Follow ZaidTwitter: https://x.com/zaidrmnLinkedIn: https://www.linkedin.com/in/zaidrahmanFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Matteo Franceschetti is the Co-founder and CEO of Eight Sleep.Eight Sleep created one of the original breakout consumer health products in 2014, quietly building a business that’s raised over $300 million dollars and was reportedly free cash flow positive in the first half of 2025.But things weren’t always easy, and Matteo shares the challenges of starting a hardware company, why hardware has stronger moats, and the fundraising mindset he adopted that eventually got Khosla Ventures and Founders Fund to invest.We also get into the importance of sleep, how the company’s Sleep Butler uses AI to help you sleep better, and the big opportunity building more consumer health products.Thanks to Numeral for supporting this episode. It’s the end-to-end platform for sales tax and compliance. Try it here: ⁠https://www.numeral.com⁠Timestamps:(2:18) Three pillars of health: sleep, nutrition, fitness(4:02) Creating a sleep routine(6:59) Importance of body temperature in sleep(8:43) How Eight Sleep works(12:14) Using AI to help you sleep(18:35) The AWS outage(24:12) It’s too hard to build in Europe(28:09) Why hardware has stronger moats(32:23) How to fundraise for a hardware company(35:30) The opportunity in Sleep tech(38:43) Hiring is easy when you have a mission(40:37) How to fight jet lag(43:03) Opportunities in women’s health(45:54) Evolving from single purchase to subscription model(47:12) Matteo’s personal health stack(49:41) Racing sports carsReferencedEight Sleep: https://www.eightsleep.com/Compliant VC Meme Account: https://x.com/compliantvcFollow MatteoTwitter: https://x.com/m_franceschettiLinkedIn: https://www.linkedin.com/in/matteofranceschetti/Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Rahul Vohra is the Founder and CEO of Superhuman Mail.Rahul sold his company to Grammarly in July of 2025, which had just acquired Coda in 2024. Following the acquisitions, the combined companies rebranded to Superhuman in October of 2025.And it’s quietly one of the most underrated businesses that no one is talking about, with over $700 million ARR and 40 million Daily Active Users. Grammarly spent 15+ years building integrations with over a million other products, that they’re now layering more AI products on top of.We talk about Rahul’s journey building Superhuman, go inside the acquisition, all the lessons he’s learned from selling two companies, why you should design your product like a video game, and we also re-visit his famous quantitative guide to finding PMF.Thanks to Todd Goldberg, Ed Sim, Shomik Ghosh, Ryan Hoover, and Rahul’s brother Gaurav Vohra for helping brainstorm topics for this conversation.Thank you to Hanover Park for supporting this episode! Upgrade your fund admin to the 21st century https://www.hanoverpark.com/TurnerTimestamps:(2:42) Inside the Superhuman acquisition(11:09) Grammarly: $700M ARR, 40M DAUs(18:53) How to sequence your product roadmap(24:43) Vision for the new Superhuman(32:43) Build your product like a video game(38:24) Designing Karamja island in Runescape(41:10) Build products like toys and games(44:53) Starting a Machine Learning PhD in 2006(48:49) Dropping out to start his first company(50:47) Rapportive’s crazy accidental launch(57:56) Meeting Superhuman co-founders(1:02:17) Being 1 of 20 to access LinkedIn’s API(1:06:38) Almost getting acquired by LinkedIn(1:10:32) Nearly dieing, getting acquired with 2 weeks of runway(1:20:08) Diligence from VCs vs Acquirers(1:26:37) Rahul’s quantitative framework for PMF(1:30:45) How to build an enduring brand(1:31:51) Rahul’s AI-powered productivity stack(1:35:01) Todd and Rahul’s angel fund(1:36:45) We need more solo foundersReferencedSuperhuman: https://www.superhuman.comGrammarly: https://www.grammarly.comHigh Resolution Fundraising: https://paulgraham.com/hiresfund.htmlHigh Resolution Fundraising: https://paulgraham.com/hiresfund.htmlSuperhuman Quantitative Framework for Finding PMF: https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit/Whisper Flow: https://wisprflow.aiFollow RahulTwitter: https://x.com/rahulvohraLinkedIn: https://www.linkedin.com/in/rahulvohra/Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/