Season 4
His 1st startup failed. His 2nd became a unicorn in just 18 months. |…
Jake founded Serval in April 2024— by Dec 2025 he'd raised a $75M Series B from Sequoia at a $1B valuation. He didn't look for a "wedge" or a "niche." He looked at ServiceNow—a $160B, 20+ year-old incumbent that everyone IT team relies on—and rebuilt it from the ground up in a YEAR. In this episode…
Solo Episode: B2B SaaS is dead. Here's what the best AI founders are …
The startup game has completely changed. If you are still building with the 2018-2022 B2B SaaS playbook, you are already behind. In this episode, we break down exactly how the GenAI shift has altered value creation, competiti...
He got rejected by 60 VCs, burned all his savings—then grew to $100M …
For the holiday break we are resurfacing some of our best episodes so far. Here is the best episode of season 3. Kyle left his job as a hacker at the NSA to launch Huntress. He bootstrapped for 3 years and burned all his savi...
He killed a $100K ARR product & pivoted—then raised $375M. | Viraj Pa…
They were building a Segment competitor. It was working—customers were paying. But every sales call, prospects kept asking about the backend tech instead of the product. So they killed the roadmap and pivoted. It took them 18...
Solo Episode: The Five Steps to Product Market Fit
For the holiday break we are resurfacing some of our best episodes so far. Here is the best episode of season 2. Here are the key lessons from the past 60 episodes that we've released to date. Each of the 5 steps to Product ...
He killed a viral app with 50k users. 2 years later, he hit $10M ARR …
David had a consumer app with 50,000 users and viral traction—and he shut it down. The retention metrics weren't as good as what he'd seen at Snapchat. That difficult decision cleared the path for Juicebox, AI for recruiting ...
Her VCs said she killed the company. 6 years later, it's worth $1.3B.…
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...
How his AI-first services company grew $0 to $40M ARR in one year. | …
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...
Q3 2025 w/Carta: What you need to raise a Series A. | Peter Walker, H…
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. …
He added AI to parking lots—then raised $3.5B. | Alex Israel, Founder…
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...
He left a $2B ARR company to build AI agents—then hit $1M ARR in < 6 …
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...
He tested his idea in one weekend—then raised $120M. | Wayne Slavin, …
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...
At 21 he made his 1st million. At 23, he grew his startup to $8M ARR …
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...
He walked away from $5M ARR—then built a $50M company. | Russ Fradin,…
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...
He made 2 key changes —then grew to $100M ARR in 2 years & exited for…
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 ...
He built a $20B public company, left—then raised a $100M Series A. | …
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 ...
5x founder asked Ford for a contract so large—they acquired his compa…
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...
He "kind of" had PMF for 8 years—until, after a rebuild, he raised $1…
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 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...