Episode
He sold his first startup for $100M. Then raised $250M in 18 months. | Dileep Thazhmon, Founder of Jeeves
- Published
- Feb 16, 2026
- Duration seconds
- 3354
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Summary
Dileep sold his first company for over $100M. For his second act, he didn't just want another win; he wanted to solve a problem that banks refused to touch: global business banking. In this episode, Dileep breaks down how Jeeves scaled to $7M ARR in just over a year by doing things that "don't scale"—like physically mailing credit cards to Argentina. He reveals the counterintuitive strategy of raising from dozens of small investors, how to pivot a fintech when interest rates skyrocket, ...