Podcast Episodes

He added AI to parking lots—then raised $3.5B. | Alex Israel, Founder of Metropolis

Season 4 Episode 94

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 bough…

Published on 7 hours ago

He left a $2B ARR company to build AI agents—then hit $1M ARR in < 6 months | Amit Shah, Founder of Instalily

Season 4 Episode 93

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—sales…

Published on 4 days, 7 hours ago

He tested his idea in one weekend—then raised $120M. | Wayne Slavin, Founder of Sure

Season 4 Episode 92

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 t…

Published on 1 week ago

At 21 he made his 1st million. At 23, he grew his startup to $8M ARR in 6 months. | Matt Espinoza, Founder of Clover

Season 4 Episode 91

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…

Published on 1 week, 4 days ago

He walked away from $5M ARR—then built a $50M company. | Russ Fradin, Founder of Larridin

Season 4 Episode 90

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. …

Published on 2 weeks ago

He made 2 key changes —then grew to $100M ARR in 2 years & exited for $2B. | Harish Abbott, Founder of Deliverr & Augment

Season 4 Episode 89

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 …

Published on 2 weeks, 4 days ago

He built a $20B public company, left—then raised a $100M Series A. | Dheeraj Pandey, Founder of Nutanix & DevRev

Season 4 Episode 88

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 o…

Published on 3 weeks ago

He built a new database in his bedroom—now he powers Cursor, Notion and Anthropic. | Simon Eskildsen, Founder of turbopuffer

Simon spent 10 years at Shopify scaling databases to millions of requests per second. Then he discovered vector databases were so expensive that companies couldn't launch AI features. So he solved it…

Published on 3 weeks, 4 days ago

He burned $4M to hit $100K ARR—but with 1 big change, he grew to $4.5M ARR in just 12 months. | Guy Podjarny, Founder of Snyk & Tessl

Guy spent 2 years and $4M building Snyk to $100K ARR. Thousands of developers loved the product. They just wouldn't pay.

Then he figured out the problem: he had product-user fit, but not product-buyer…

Published on 4 weeks ago

5x founder asked Ford for a contract so large—they acquired his company instead. | Amar Varma, Founder of Mantle

Season 4 Episode 85

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 wi…

Published on 1 month ago