He sold his first startup for $100M. Then raised $250M in 18 months. | Dileep Thazhmon, Founder of Jeeves

Episode notes

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, and why being an outsider was his biggest advantage in building a global banking infrastructure from scratch. Why You Should Listen How to get to $7M ARR in one year through unscalable acts. Why a "messy" cap table with 50+ investors is actually a secret weapon. The "Beat Down" Framework: A brutal stress test for vetting your idea. The offline marketing stunt that actually worked.