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Copyright: © Turner Novak
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/
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/
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
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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
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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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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/
Austin Petersmith is the Co-founder and CEO of Howie, the AI secretary.
We talk about why AI assistants are so hard to build, why they decided to build Howie super narrow, and everything that went into their brand, name, and viral launch.
Thank you to Adam D’Augelli, Sophia Amoruso and Alex Cohen for help brainstorming topics for the conversation.
Thank you to Hanover Park for supporting this episode. Try the modern, AI-native fund admin at https://www.hanoverpark.com/Turner
Timestamps:
(3:35) Howie: The AI Secretary
(6:08) Why AI assistants are so hard to build
(16:19) Why Howie started in email
(20:49) Adding a human in the loop
(30:48) AI software vs AI-powered humans
(36:21) How a meme inspired Howie
(39:29) Inside the making of Howie’s launch video
(44:15) Howie’s viral launch video + Discussion
(53:47) Designing the brand
(1:01:37) Long-term opportunity and roadmap
(1:07:53) Working for Jason Calacanis
(1:12:00) Jason's media lessons
(1:16:51) Getting Howie's first users
(1:19:35) Pitch deck strategy that raised $6m
(1:24:09) The mistake of optimizing for growth too soon
(1:29:48) Building an AI company outside of SF
(1:33:13) Being Superhuman’s 1st customer, Mercury’s 3rd
Referenced
Try Howie: https://howie.com/
Jobs at Howie: https://app.dover.com/jobs/howie
Howie Dewitt Meme: https://knowyourmeme.com/memes/howie-dewitt
NewKid: https://newkid.services/
Follow Austin
Twitter: https://x.com/awwstn
LinkedIn: https://www.linkedin.com/in/awwstn
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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