The Peel with Turner Novak

• Building Flex, the AI Private Bank with CEO Zaid Rahman

  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/

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• Inside Eight Sleep | Using AI to Sleep Better | CEO Matteo Franceschetti

  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/

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• Inside the New Superhuman: $700M ARR, 40M Daily Users with Rahul Vohra

  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/

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• Inside Stripe: Stablecoins, AI, and (not) Going Public | Will Gaybrick, President of Technology and Business at Stripe

  Will Gaybrick is the President of Technology and Business at Stripe.Stripe builds financial infrastructure for the internet, and if you’ve ever purchased a product online, you’ve probably used Stripe.We talk about what Stripe’s doing in crypto and stablecoins, how AI is changing commerce and payments, how they’re thinking about going public, how they build products internally, and interesting data they’re seeing around AI-native companies, like how they’re growing 3.5x faster than SaaS companies.Thank you to Claire Hughes Johnson, Josh Kushner, and Cosmin Nicolaescu for help brainstorming topics for the conversation.Thank you to Numeral and Amplitude for sponsoring this episode.Numeral: The end-to-end platform for sales tax and compliance. Try it here: https://www.numeral.comAmplitude: Listen to users at scale with AI https://www.amplitude.com/AI-FeedbackTimestamps:2:42 Will’s promotion5:29 Build vs Buy in AI6:39 Inside the Bridge acquisition8:54 Stripe’s stablecoin strategy11:20 Why building Stripe is so complicated13:22 How Stripe builds new products18:29 AI companies growing 3.5x faster than SaaS22:58 New fraud vectors in AI businesses25:19 Agentic commerce in ChatGPT29:34 Building modular products34:05 How Stripe uses AI internally42:12 Building the first payments foundation model48:23 Link, Stripe’s 200M user consumer product56:52 Will Stripe ever IPO?59:14 Blurring of private and public companies1:03:39 Starting Hack Yale1:08:23 Joining Thrive’s $5 million Fund 11:12:30 Low margin businesses are underrated1:16:30 Joining Stripe as CFO1:21:59 How Stripe’s go-to-market has evolved1:25:56 Stripe’s margins1:29:52 Why financial services are so hard to use1:33:04 Lessons from Alan MulallyReferencedStripe: https://stripe.com/Careers at Stripe: https://stripe.com/jobs/searchFollow WillTwitter: https://x.com/gaybrickLinkedIn: https://www.linkedin.com/in/william-gaybrick-5730347Follow 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/

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• Roger Ehrenberg | Investing in Sports, 10x Funds, Traits of Top Founders, Current Seed Stage Market, Investing in Detroit

  Roger Ehrenberg is the Co-founder of Game Changers Ventures and IA Ventures.We talk about the current Seed stage venture environment, what he learned investing in sports teams, how COVID changed sports, what he’s investing in today, characteristics of the top founders, advice for emerging managers, and his real estate and consumer brand projects in Detroit.Thank you to Michael Kim, Jon Oberheide, Jesse Beyroutey, James Fitzgerald, Dan Feder, Sarah Smith, Marc Weisser, and Charles Hudson for help brainstorming topics for the conversation.Thank you to Hanover Park for supporting this episode. Upgrade to an AI-native fund admin at https://www.hanoverpark.com/TurnerTimestamps:3:45 Current Seed stage market7:17 Starting Game Changers to invest in sports 12:25 Investing in the Miami Marlins16:45 Investment opportunities in sports18:21 Tomorrow Golf League23:54 Investing in sports teams25:50 Business models in sports27:12 Importance of real estate development, gambling32:53 How COVID changed sports38:41 Clippers experimenting with cheap tickets & concessions41:51 Opportunities monetizing super fans46:51 Sports as an investable venture asset53:24 Great founders find big TAMs56:31 The desire to win58:09 Sending letters to break into Wall Street from Michigan1:02:38 Raising IA Ventures Fund 1 in 20091:07:58 Advice for emerging managers1:13:18 The Trade Desk’s three bridge rounds1:18:03 Lessons on recycling capital1:20:16 What it’s like working with your kids1:24:53 Brand Detroit1:29:14 Being world class at multiple disciplinesReferencedGame Changers Ventures: https://gamechangers.vcIA Ventures: https://www.iaventures.comEberg Capital: https://www.ebergcapital.comTGL Golf: https://tglgolf.comBrand Detroit: https://www.branddetroit.comFollow RogerTwitter: https://x.com/infoarbitrageLinkedIn: https://www.linkedin.com/in/rehrenbergFollow 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/

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