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How US Healthcare Actually Works, the WWII Tax Loophole that Broke it Forever, and How AI Can Fix it | Nikhil Krishnan, Out of Pocket
Nikhil Krishnan is the Founder of Out of Pocket, a media company that makes understanding healthcare more entertaining and accessible. We spend 100 minutes talking about how the US healthcare system actually works, how World War II changed
Sophia Amoruso on Bootstrapping Nasty Gal to $120M Revenue, Turning Down $400M, Declaring Bankruptcy, Public Failure, Starting Trust Fund to Back Other Founders
Sophia Amoruso is the Founder of Nasty Gal and Trust Fund, an early stage venture capital firm. We talk through her journey of starting Nasty Gal as an Ebay store in 2006 to sell vintage clothing, bootstrapping it to $28 million in revenue,
Footwork’s Secret Sauce | Mike Smith and Nikhil Basu Trivedi
Nikhil Basu Trivedi and Mike Smith are the Co-founders of Footwork where they invest up to $15 million in Seed and Series A rounds. This is the first time they've ever sat down to record a conversation together on video. We talk about start
Inside Hanover Park: Building an AI-Native Service Business, Growing to $15B in Assets
Chris Hladczuk is the Co-founder and CEO of Hanover Park, the AI-native fund administrator, vertically integrating fund administration, portfolio management, and LP experience for finance and investment teams. Chris is the 2nd ever returnin
Inside Canada’s Fastest Growing AI Company | Spellbook, Scott Stevenson
Scott Stevenson is the Co-founder and CEO of Spellbook. Spellbook is an AI copilot for contract review and drafting, essentially “Cursor for lawyers.” They have 4,000 customers in 80 countries, and to my knowledge is the fastest growing AI
Benchmark’s Chetan Puttagunta on the Past, Present, & Future of Software
Chetan Puttagunta is a General Partner at Benchmark. We talk about investing in Manus, the AI company that went from zero to $100M ARR in eight months and was recently acquired by Meta. We also talk through the full history of application s
Inside Serval: Building the System of Intelligence for IT | Jake Stauch
Jake Stauch is the Co-founder and CEO of Serval. Serval automates IT with AI. We talk taking on incumbents with an AI-native product, why IT departments haven’t had much automation historically, the 12+ month journey of landing their first
Garry Tan on the Past, Present, and Future of YC
Gary Tan is the President and CEO of Y Combinator. YC is the startup accelerator behind companies like Airbnb, Stripe, Coinbase, Reddit, Twitch, and thousands more. According to Garry, they’ve invested in 20% of all startups worth $5B or mo
Building the Wearable That Gets You Stronger | Miranda Nover, Co-founder of Fort Health
Miranda Nover is the Co-founder and CEO of Fort Health. Fort builds wearables that automatically track strength training for people who care about longevity. This is a new format I’m experimenting with. It’s the first time I’ve had a Banana
How Duo Security went Zero to $1B ARR in Ann Arbor | Dug Song, Jon Oberheide
Dug Song and Jon Oberheide are the co-founders of Duo Security. If you’ve never heard of Duo, it might be one of the most underrated software stories of all-time. Starting in 2010, they burned only $14 million to hit $100m in ARR, were acqu
Building Real-Time Data Streaming for AI | Jacqueline Cheong, Co-founder and CEO of Artie
Jacqueline Cheong is the Co-founder and CEO of Artie. Artie moves data across your systems in real-time, and we talk about why that’s so important in the age of AI. It’s a lot harder than you’d think, as less than 5% of real-time data strea
The State of AI: Rise of Reasoning, Surge in Chinese Open Source, Sovereign AI , How to Invest in AI Today | Nathan Benaich, Air Street Capital
Nathan Benaich is the founder of Air Street Capital and author of the State of AI report. On its eighth year, the report is a year-long effort on the biggest things happening in AI, across research, industry, politics, and safety. This epis
Building the $3B API That Didn’t Exist, Europe’s Regulation Problem | Marcelo Lebre, Co-founder of Remote
Marcelo Lebre is the Co-founder and President of Remote, the payroll and international employment company. Remote is one of today's most underrated software companies. We get into why payroll is such a hard problem, why most of the industry
Kevin Hartz | Backing Teen Founders, Lessons from the PayPal Mafia
Kevin Hartz, Co-founder of A*, Eventbrite, Xoom, and Sauron. Kevin has been building and investing in technology companies for 30 years, and we talk about how the industry’s evolved, why he calls AI the Mother of All Bubbles, why we’re stil
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
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 a
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 Ser
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 ca
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.
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 c
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, charac
Why AI Will Never Replace Engineers, Inside the 996 Discourse, and Creative Marketing | Daksh Gupta, 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 o
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 wou
Building AI-Native Infrastructure for Developers | Erik Berhnardsson, CEO of Modal
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 actual
Howie: The AI Secretary | Austin Petersmith, Co-founder and CEO
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. T
How Loops Fixes Email for Developers with Co-founder and CEO Chris Frantz
Chris Frantz is the Co-founder and CEO of Loops, the email platform for software companies. We get into why sending emails is still a big problem, his hilariously simple framework for building products, getting in to YC with a last minute a
Untold Startup Lessons from Dozens of Academic Research Papers with Dan Gray at Equidam
Dan Gray is the Head of Insights at Equidam. If you’re a tech and investing nerd like us, you’ll love this conversation. We cover everything Dan’s learned reading dozens of academic research papers on startups and venture capital, debunking
Rethinking Asset Allocation, The Past Present and Future of Venture Capital | Dan Feder, University of Michigan
Dan Feder is a Senior Managing Director of Investments at the University of Michigan’s $18 billion endowment. Our two hour conversation talks through the past, present, and future of all things venture capital, and investing more broadly. D
Inside Intercom’s AI Turnaround, Why Software Companies Must Train Their Own Models | Eoghan McCabe, Co-founder and CEO
Eoghan McCabe is the Co-founder and CEO of Intercom, building Fin.ai, the AI customer service company. This was an extremely candid, two hour conversation going inside every detail of how Intercom was the first late stage software company t
How To Generate Alpha in Venture Capital | Albert Azout, Level Ventures
Albert Azout is the Co-founder and Managing Partner of Level Ventures, combining first-principles thinking with state-of-the-art data science to back and build top seed-stage firms and their breakout companies. Venture investing is hard, an
