The Peel with Turner Novak

• 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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• 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/NumeralThePeelHanover Park: Modern, AI-native fund admin at https://www.hanoverpark.com/TurnerTimestamps:(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 datingReferencedGreptile: https://www.greptile.com/Careers at Greptile: https://www.greptile.com/careersMonetizing Innovation: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867Greptile Work Culture: https://www.greptile.com/blog/work-cultureEpisode with Adit @ Reducto: https://youtu.be/h98dLRJFHMMFollow DakshTwitter: https://x.com/dakshgupLinkedIn: https://www.linkedin.com/in/dakshg/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 Reducto: YC to Series B in 18 Months, From Pivot to Fortune 10 Customers, Lessons in Founder-Led Sales | Adit Abraham, Co-founder and CEO of Reducto

  Sign-up here to get weekly episodes + transcripts in your inbox: https://www.thespl.it/Adit Abraham is the Co-founder and CEO of Reducto. Reducto’s product takes PDFs and physical documents, and extracts all the data, just like a human would if they were reading it.At the time of recording, they’ve processed over 1 billion pages, grew 6x over the past five months, and are fresh off a $75 million Series B led by a16z. And Adit told me they’ve only burned $1 million of capital so far to get here.And the craziest part, Adit told me they’ve only burned $1 million of capital so far to get here.Anyone building an AI product probably sees Reducto as essential infrastructure. Our conversation gets into how they built the best product in the space, landing a Fortune 10 customer as a two-person startup, getting to $1 million in ARR within a few months, lessons doing founder led sales to over $5 million in ARR, and what the future of PDF’s, and human / computer data looks like.Thank you to Liz Wessel at First Round, Chetan Puttagunta at Benchmark, and Adel Wu at Reducto for helping brainstorm topics for Adit.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/NumeralThePeelHanover Park: Modern, AI-native fund admin at https://www.hanoverpark.com/TurnerTimestamps:(3:35) Reading unstructured human data(10:44) Growing 5x in four moths(12:38) Insurance, healthcare, legal, logistics(19:13) Where LLM’s still struggle(28:23) Starting Reducto from a blog post during YC(32:01) Landing a Fortune 10 customer with two people(35:48) Limiting the product and growth early on(40:57) Getting an MIT professor fired(43:50) How to avoid pivot hell(49:00) $108M from First Round, Benchmark, a16z(51:48) Chetan convincing them to raise a Series A(55:50) Raising a Series B in 48 hours(59:36) Redeye flight to hire the 1st AI researcher(1:05:42) Lessons hitting $5m ARR with founder-led sales(1:13:09) Staying on top of changes in AI modelsReferenced:https://reducto.aihttps://reducto.ai/careersFollow AditTwitter: https://x.com/aditabrmLinkedIn: https://www.linkedin.com/in/aditabrahamFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSign-up here to get weekly episodes + transcripts in your inbox: https://www.thespl.it/

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