Season 4

Jennifer went from VC to founder and immediately broke every rule in the book. When she pivoted Scribe from an automation tool to a documentation platform, her investors told her she had just killed the company. She ignored t...

Eric spent 30 years in cybersecurity. Built and sold an MSSP to private equity for hundreds of millions. Then he started Tenex and hit $43 million in revenue in ONE YEAR. This isn't theory. This is a founder who's done it mul...

Carta's Peter Walker is back with the freshest data on what's actually happening at the early stage—and it's not what you're reading on X. While headlines scream about record-breaking rounds, the reality on the ground tells a different story. Seed deals are down. Time between rounds is stretching. …

Alex and his co-founders spent 2018 pitching parking lot owners on computer vision tech. Every meeting ended the same way: "Cute startup, come back in 30 years." So they did something else—they bought the parking operators an...

Amit walked away from being President of 1-800-Flowers after scaling it from $500M to $2B because he saw smart people trapped in dumb systems. His insight: half of global GDP is 90% manual work—salespeople entering data inste...

Wayne tested flight insurance over a single weekend with a WordPress site and Google ads. When people tried to pay, he showed a fake error message. The result: 15.9% conversion. That validation led to Sure, now powering insur...

Matt sold his first company at 19 and made $100K. He sold his second at 21 and made $800K. A couple years later, he launched Clover and grew it to $8M ARR in 6 months. His secret? Insane distribution. His formula is to ignore...

Russ has started and sold multiple companies over 30 years, but his Dynamic Signal journey will change how you think about product-market fit. They had $5M ARR selling influencer marketing software. Then Russ told investors t...

Harish spent 9 months building Deliver and could barely get 10 customers. The product worked. Merchants liked the fast delivery promise. But nobody was signing up. Then he made two changes—and scaled to $100M in revenue in 2 ...

Dheeraj built Nutanix into a $20B public company—then walked away to start DevRev. He just raised a $100M Series A. This episode breaks down why most founders "sell and run" (chase new logos instead of delivering value), why ...

Amar is a 5x founder who helped birth Tinder (it was the 10th project—after the first 9 failed), then sold his next company to Ford for putting a platform in every single vehicle they make. But the wildest part? He got Ford t...

Ben Alarie spent 8 years building Blue J with "partial product market fit"—real customers, real revenue, but no real market pull. Then he made a bet that would either kill the company or 10x it: he put the existing product in maintenance mode and gave his team 6 months to rebuild everything from sc…

Dean thought he'd have to bootstrap Axonius because no investor would fund a solution to a problem that had existed for 20 years. He was wrong—they've raised $500M. The breakthrough came when a Fortune 500 company was actively being hacked by Chinese state actors. Their first customer almost said n…

Casey turned hackers into a marketplace and built Bugcrowd to $180M+ raised. But the real story isn't about cybersecurity—it's about how he validated a two-sided marketplace with almost no product, refined his pitch by literally testing it on Uber drivers until it clicked, and cracked the code on c…

Zach spent 8 years at Google leading engineering for Google Docs, then left to build a photo sharing app with zero go-to-market plan. Reality hit hard: "At Google, anything you launch gets millions of users. At a startup, the...

Alex had $2,000 in his checking account when Microsoft acquired his last company. For years, he paid himself $30K while his friends made six figures at corporate jobs. He had only 2 months of runway for 18 straight months. Th...

Brett had a drug dealer's car for 13 days. By day 11, the death threats started coming. This is the reality of building ServiceUp, the "DoorDash for auto repair." Brett literally stole DoorDash's entire playbook—city launches, three-sided marketplace, everything—but discovered even if he got 90% ri…

Doug Scott and the Ethic team spent years building technology before landing real customers. While other startups were growing fast, Ethic was focused on building, and after two years had only a modest amount of AUM. Until he...

Arnold Schwarzenegger mastered three completely different fields—bodybuilding, acting, and politics—with one simple philosophy: reps, reps, reps. This solo episode reveals why speed of execution is the only real moat for earl...

Aviv spent months walking construction sites carrying tools for managers just to understand their problems—speaking to customers is "bullsh*t"—you need to work beside them to see reality. His company Buildots had a working AI...

Shensi cold messaged 50,000 engineers to build Merge. She worked 9am-9pm every day, gave her first customers two months free to prove herself, and refused to hire anyone remote—even during peak COVID. She purposefully didn't ...

Eldon put a $150K line of credit on his house to start eSentire in 2001. No VCs would touch him—they didn't understand services businesses. He worked 12-hour days, 7 days a week for 7 years to hit $1M in revenue. His co-found...

Soham spent 6 months building AI that would auto-generate integrations between any software. He locked down Glean as an early customer because he had friends there. And it failed completely. So he pivoted. This time, he refus...

Sahil was 18 when TechCrunch published a hit piece calling him a copycat. His co-founder Aaron was 16. They'd just raised $6 million from YC and top VCs for their crypto startup, then got subpoenaed by a state government and ...