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

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

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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

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LinkedIn: https://www.linkedin.com/in/turnernovak

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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/

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/

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/

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/

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/

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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/NumeralThePeel

Hanover Park: Modern, AI-native fund admin at https://www.hanoverpark.com/Turner

Timestamps:

(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 models

Referenced:

https://reducto.ai

https://reducto.ai/careers

Follow Adit

Twitter: https://x.com/aditabrm

LinkedIn: https://www.linkedin.com/in/aditabraham

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Twitter: https://twitter.com/TurnerNovak

LinkedIn: https://www.linkedin.com/in/turnernovak

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Erik Bernhardsson is the Co-founder and CEO of Modal, building high-performance AI infrastructure.

We talk about building what is essentially a new cloud provider, created from the ground up, optimized for AI. We also talk about what actually happened with the great GPU shortage, how Modal fixes the inference problem in AI, and why he thinks AI will lead to 10x more developers.

He also shares lessons on culture from joining Spotify as the 40th employee, treating hiring like a prediction problem, what most people get wrong working with early customers, why more people should start companies in their 30’s and 40’s, and reflections on fundraising in a hot market.

Thank you to Tim Chen at Essence Venture Capital and Erik’s Co-founder Akshat for their help brainstorming topics for this conversation.

Thank you to Meow and Hanover Park for supporting this episode.

Meow: Get free bookkeeping for your startup at https://www.meow.com

Hanover Park: Modern, AI-native fund admin at https://www.hanoverpark.com/Turner

Timestamps:

(4:26) Modal: AI-native infrastructure

(9:02) Why its so hard to get GPU’s

(15:00) Hitting PMF with AI generated media

(20:37) Competing in IOI competitions

(23:09) 40th employee at Spotify

(27:17) Lessons from Spotify

(31:17) Starting Better[dot]com

(34:05) Treating hiring like a prediction problem

(36:12) Erik’s favorite interview question

(39:07) Sales + common design partner mistakes

(42:02) Startups should solve hard problems

(44:05) Evolution of Modal’s product over time

(50:15) Rise in importance of inference in AI

(52:07) AI development post-GPU scarcity

(58:51) Building a brand in dev tools

(1:04:31) Fundraising from Seed to Series B

(1:07:42) More 30+ year old’s should start companies

(1:10:00) Reducing developer tax, increasing productivity

(1:20:37) Why Erik’s bullish and bearish on AI

(1:26:17) Bubbles, downsides to inappropriate valuations

(1:34:58) High CO2 levels make you dumb

(1:37:38) Difference between US and European startups

Referenced

Modal: https://modal.com

Careers at Modal: https://jobs.ashbyhq.com/modal

Suno: https://suno.com

Planet Scale: https://planetscale.com

How to hire smarter than the market: https://erikbern.com/2020/01/13/how-to-hire-smarter-than-the-market-a-toy-model

Interviewing is a noisy prediction problem: https://erikbern.com/2018/05/02/interviewing-is-a-noisy-prediction-problem

Cloud in 2030: https://erikbern.com/2021/11/30/storm-in-the-stratosphere-how-the-cloud-will-be-reshuffled

Follow Erik

Twitter: https://x.com/bernhardsson

LinkedIn: https://www.linkedin.com/in/erikbern

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/