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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. T…
4 months, 3 weeks 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 $8…
5 months 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 h…
5 months 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 w…
5 months, 1 week 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 …
5 months, 1 week 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 comp…
5 months, 2 weeks 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 probl…
5 months, 2 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 pla…
5 months, 3 weeks ago
He "kind of" had PMF for 8 years—until, after a rebuild, he raised $100M | Ben Alarie, Founder of Blue J
Season 4 Episode 84
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 …
5 months, 3 weeks ago
They failed every POC—then grew their cybersecurity platform to $100M ARR in 5 years. | Dean Sysman, co-founder of Axonius
Season 4 Episode 83
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'v…
5 months, 4 weeks ago