The Peel with Turner Novak

Turner Novak

Exploring the world’s greatest startup stories. Get a behind the scenes look into the founding stories of your favorite companies. Learn how the industries they operate in actually work, and learn playbooks and tactics you can use to launch and scale your own business.

  1. Inside the All-In Podcast: Lessons from Elon, Trump, Oprah, Travis Kalanick, Investing in 100+ Startups per Year with Jason Calacanis

    DEC 18

    Inside the All-In Podcast: Lessons from Elon, Trump, Oprah, Travis Kalanick, Investing in 100+ Startups per Year with Jason Calacanis

    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.com⁠ Timestamps: (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 week Referenced Howie: ⁠https://howie.com/⁠ All-In Podcast: ⁠https://allin.com/⁠ Bret Easton Ellis (Podcast): ⁠https://www.breteastonellis.com/podcast⁠ Red 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/TheAdamFriedlandShow⁠ The Insider (Movie): ⁠https://www.imdb.com/title/tt0140352/⁠ Launch: ⁠https://www.launch.co/⁠ Ro: ⁠https://ro.co/⁠ Follow Jason Twitter: ⁠https://twitter.com/Jason⁠ LinkedIn: ⁠https://www.linkedin.com/in/jasoncalacanis/⁠ Follow Turner Twitter: ⁠https://twitter.com/TurnerNovak⁠ LinkedIn: ⁠https://www.linkedin.com/in/turnernovak⁠ Subscribe to my newsletter to get every episode + the transcript in your inbox every week: ⁠https://www.thespl.it

    1h 43m
  2. Why the Future of Software is AI and Human Collaboration | Steven Fabre, Co-founder and CEO, Liveblocks

    DEC 11

    Why the Future of Software is AI and Human Collaboration | Steven Fabre, Co-founder and CEO, Liveblocks

    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.com⁠ Timestamps: (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 business Referenced Liveblocks: https://liveblocks.io/ Careers at Liveblocks: https://join.team/liveblocks Follow Steven Twitter: https://x.com/stevenfabre LinkedIn: https://www.linkedin.com/in/steven-fabre-5510bb38 Follow Turner Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

    1h 37m
  3. Building Flex, the AI Private Bank with CEO Zaid Rahman

    DEC 4

    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 opportunity Referenced Try Flex: https://www.flex.one Careers at Flex: https://jobs.lever.co/Flex/ Basel III https://en.wikipedia.org/wiki/Basel_III Linguistic TikTok account: https://www.tiktok.com/@zaydupree Lazy 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-7801be30 Follow Zaid Twitter: https://x.com/zaidrmn LinkedIn: https://www.linkedin.com/in/zaidrahman Follow Turner Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

    2h 32m
  4. Inside Eight Sleep | Using AI to Sleep Better | CEO Matteo Franceschetti

    NOV 25

    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.com⁠ Timestamps: (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 cars Referenced Eight Sleep: https://www.eightsleep.com/ Compliant VC Meme Account: https://x.com/compliantvc Follow Matteo Twitter: https://x.com/m_franceschetti LinkedIn: https://www.linkedin.com/in/matteofranceschetti/ Follow Turner Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

    53 min
  5. Inside the New Superhuman: $700M ARR, 40M Daily Users with Rahul Vohra

    NOV 20

    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/Turner Timestamps: (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 founders Referenced Superhuman: https://www.superhuman.com Grammarly: https://www.grammarly.com High Resolution Fundraising: https://paulgraham.com/hiresfund.html High Resolution Fundraising: https://paulgraham.com/hiresfund.html Superhuman Quantitative Framework for Finding PMF: https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit/ Whisper Flow: https://wisprflow.ai Follow Rahul Twitter: https://x.com/rahulvohra LinkedIn: https://www.linkedin.com/in/rahulvohra/ Follow Turner Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

    1h 40m
  6. Inside Stripe: Stablecoins, AI, and (not) Going Public | Will Gaybrick, President of Technology and Business at Stripe

    NOV 13

    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.com Amplitude: Listen to users at scale with AI https://www.amplitude.com/AI-Feedback Timestamps: 2:42 Will’s promotion 5:29 Build vs Buy in AI 6:39 Inside the Bridge acquisition 8:54 Stripe’s stablecoin strategy 11:20 Why building Stripe is so complicated 13:22 How Stripe builds new products 18:29 AI companies growing 3.5x faster than SaaS 22:58 New fraud vectors in AI businesses 25:19 Agentic commerce in ChatGPT 29:34 Building modular products 34:05 How Stripe uses AI internally 42:12 Building the first payments foundation model 48:23 Link, Stripe’s 200M user consumer product 56:52 Will Stripe ever IPO? 59:14 Blurring of private and public companies 1:03:39 Starting Hack Yale 1:08:23 Joining Thrive’s $5 million Fund 1 1:12:30 Low margin businesses are underrated 1:16:30 Joining Stripe as CFO 1:21:59 How Stripe’s go-to-market has evolved 1:25:56 Stripe’s margins 1:29:52 Why financial services are so hard to use 1:33:04 Lessons from Alan Mulally Referenced Stripe: https://stripe.com/ Careers at Stripe: https://stripe.com/jobs/search Follow Will Twitter: https://x.com/gaybrick LinkedIn: https://www.linkedin.com/in/william-gaybrick-5730347 Follow Turner Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

    1h 36m
  7. Roger Ehrenberg | Investing in Sports, 10x Funds, Traits of Top Founders, Current Seed Stage Market, Investing in Detroit

    NOV 6

    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/Turner Timestamps: 3:45 Current Seed stage market 7:17 Starting Game Changers to invest in sports 12:25 Investing in the Miami Marlins 16:45 Investment opportunities in sports 18:21 Tomorrow Golf League 23:54 Investing in sports teams 25:50 Business models in sports 27:12 Importance of real estate development, gambling 32:53 How COVID changed sports 38:41 Clippers experimenting with cheap tickets & concessions 41:51 Opportunities monetizing super fans 46:51 Sports as an investable venture asset 53:24 Great founders find big TAMs 56:31 The desire to win 58:09 Sending letters to break into Wall Street from Michigan 1:02:38 Raising IA Ventures Fund 1 in 2009 1:07:58 Advice for emerging managers 1:13:18 The Trade Desk’s three bridge rounds 1:18:03 Lessons on recycling capital 1:20:16 What it’s like working with your kids 1:24:53 Brand Detroit 1:29:14 Being world class at multiple disciplines Referenced Game Changers Ventures: https://gamechangers.vc IA Ventures: https://www.iaventures.com Eberg Capital: https://www.ebergcapital.com TGL Golf: https://tglgolf.com Brand Detroit: https://www.branddetroit.com Follow Roger Twitter: https://x.com/infoarbitrage LinkedIn: https://www.linkedin.com/in/rehrenberg Follow Turner Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

    1h 31m

  8. OCT 31

    Why AI Coding Will Never be 100% Autonomous, How Engineering Teams Are Actually Adopting AI, Inside the 996 Discourse, How to do Creative Marketing | Daksh Gupta, Co-founder and CEO of Greptile

    Daksh Gupta is the Co-founder and CEO of Greptile, the AI code reviewer that understands your entire code base. Greptile just closed a $25M Series A led by Eric Vishria at Benchmark, and we get into their long and winding journey to build one of the fastest growing AI companies. Thanks to Suds at SF1 for helping brainstorm topics for the conversation. Thank you to Numeral and Hanover Park for sponsoring this episode. Numeral: The end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeel Hanover Park: Modern, AI-native fund admin at https://www.hanoverpark.com/Turner Timestamps: (3:15) Evolution of AI coding + code review (11:23) Coding will never be fully automated (18:07) Why you need a separate code reviewer (24:34) How eng teams adopting AI is changing (27:37) Why LLM costs will come down (31:54) Pricing AI products (35:27) Getting your team to adopt AI (38:17) How Daksh started the 996 discourse (42:10) Recruiting is a funnel, open roles are a product (49:19) Making an energy drink for programmers (51:19) Brainstorming marketing stunts (57:22) Don’t do hype marketing too early (59:41) Starting a band, hitting #14 on Spotify (1:06:35) Evolution of the startup meta (1:12:39) Starting Greptile in class at Georgia Tech (1:19:18) Moving to SF, getting into YC (1:23:44) Pivoting from codebase chat to code review (1:27:09) Crazy growth and mimetic desire (1:29:47) Pricing AI software (1:34:44) How to market developer tools (1:39:46) Greptile's fundraising journey (1:42:57) Why YC is worth the 7% dilution (1:46:39) Treat fundraising like dating Referenced Greptile: https://www.greptile.com/ Careers at Greptile: https://www.greptile.com/careers Monetizing Innovation: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867 Greptile Work Culture: https://www.greptile.com/blog/work-culture Episode with Adit @ Reducto: https://youtu.be/h98dLRJFHMM Follow Daksh Twitter: https://x.com/dakshgup LinkedIn: https://www.linkedin.com/in/dakshg/ Follow Turner Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

    1h 55m
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4.6
out of 5
11 Ratings

About

Exploring the world’s greatest startup stories. Get a behind the scenes look into the founding stories of your favorite companies. Learn how the industries they operate in actually work, and learn playbooks and tactics you can use to launch and scale your own business.

Information

  • Creator
    Turner Novak
  • Years Active
    2023 - 2025
  • Episodes
    123
  • Rating
    Explicit
  • Copyright
    © Turner Novak
  • Show Website
    The Peel with Turner Novak

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