Episodes
He "kind of" had PMF for 8 years—until, after a rebuild, he grew 10x …
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…
They failed every POC—then grew their cybersecurity platform to $100M…
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…
He tested his pitch on Uber drivers—then built a cybersecurity platfo…
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…
He quit Google & his 1st startup failed—but his 2nd grows at $1M ARR …
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...
He tried to return $200K to investors 30 days in—then exited to Micro…
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...
A drug dealer threatened to kill him—then he grew 50x in 3 Years to $…
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…
He pitched 100 VC and spent 3 years building— then grew to $7B AUM. |…
Doug spent 3 years building technology before landing real customers. While other startups were growing fast, Ethic was stuck at $5M AUM after two years. Until he found a way to help his customers help them WIN new clients th...
PMF Observations: Speed is the only startup moat—& why most founders …
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...
He spent 5 months working with customers before building—then grew to…
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...
She cold messaged 50,000 engineers—then grew to $10M+ ARR. | Shensi D…
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 ...
He bet his house on a startup—took 7 years to $1M, then hockey stick …
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...
He quit his job, went all-in on AI agents—then grew to 100K users & a…
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...
TechCrunch called him a fraud at 18—then he built a $10M ARR fintech.…
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 ...
Paul Graham Said His Startup Was Worthless—2 Months Later He Hit $1M …
Jon spent 3 years building Gamma with barely any traction—just a few hundred users after burning millions. Then ChatGPT dropped. In desperation, he pivoted to AI-powered presentations in March 2023 with one year of runway lef...
He quit Google, launched Rubrik—then grew to $1B ARR & a $16B market …
Soham co-founded Rubrik by taking what he learned from building Google's data center tech to enterprises desperate for cloud migration. Two quarters later, he hit $1M ARR. And a few years later, a $16B IPO. Soham breaks down why paid pilots beat free trials, how to sell enterprise hardware before i…
He Bootstrapped to $55M in Revenue—without ever having to hit 100% Yo…
Stéphan bootstrapped AODocs to $55M in revenue and 250 employees without taking a dime of VC money—while competing directly with venture-backed competitors. Starting as a services company in 2012, he spotted the cloud migrati...
He Bootstrapped Wrike to $10M ARR—then exited for $2.2B. | Andrew Fil…
Andrew bootstrapped Wrike and grew it from 0 to a $2.2B exit by doing the exact opposite of what every startup book tells you. No pivots. No talking to customers before launch. No narrow niche. Just 17 years of relentless foc...
Q2 2025: The new Series A Bar is $3M ARR—& only 20% of seed startups …
Peter Walker from Carta drops the hard data every founder needs. Based on actual cap table data from 1000s of startups, this Q2 update reveals the brutal new reality. It takes 2+ years to go from seed to A (up from 1.6), you ...
His Video AI app hit $10M+ ARR in Months—without a sales team. | Mich…
Hedra CEO Michael Lingelbach breaks down how his generative video app went from zero to millions of users and an eight-figure run rate in months — then deliberately slowed down to rebuild a V2 that enterprises would pay for. ...
He grew to millions in ARR in 18 months—by fighting with his co-found…
Ross went from lawyer to self-taught engineer to CTO at a 1,600-person unicorn—then quit to build Wordsmith AI. In 18 months, he's raised $30M and grown to mid-single-digit millions in ARR by doing everything differently. He ...
He thought his startup would fail—then grew to $100M ARR. | Rick Song…
Rick built Persona into a $100M+ ARR unicorn, but he never thought it would work. In fact, Rick started Persona believing it would probably fail, and that mindset might be exactly why it succeeded. In this episode, Rick revea...
Forget PMF—Neil Patel says to give your product away for free instead…
Neil Patel just flipped everything you know about startups upside down. He says product-market fit is overrated, giving away your software for free can make you rich, and the real secret to scaling isn’t charging customers—it...
He got kicked out of Harvard—then grew to $5M ARR in just 3 months. |…
Roy Lee went from getting kicked out of Harvard and Columbia to building Cluely, one of the fastest-growing AI startups ever—going from 0 to $5 million ARR in just 3 months. We go deep on Roy’s playbook for using controversy,...
She raised $1.3M, and delivered real, strategic value — then shut it …
Mary Beth Snodgrass shares the raw and real story behind Healthiby—an innovative healthcare startup that succeeded in delivering measurable health outcomes but ultimately didn't take off. Hear firsthand what went wrong, from ...