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

Page: https://stenobird.com/podcast/a-product-market-fit-show/he-sold-his-first-startup-for-100m-then-raised-250m-in-18-months-dileep-thazhmon-founder-of-jeeves
Text version: https://stenobird.com/podcast/a-product-market-fit-show/he-sold-his-first-startup-for-100m-then-raised-250m-in-18-months-dileep-thazhmon-founder-of-jeeves.md
Podcast: [A Product Market Fit Show | Startup Podcast for Founders](https://stenobird.com/podcast/a-product-market-fit-show)
Published: 2026-02-16T10:00:00+00:00
Episode link: https://www.buzzsprout.com/1889238/episodes/18461238-he-sold-his-first-startup-for-100m-then-raised-250m-in-18-months-dileep-thazhmon-founder-of-jeeves.mp3
Audio file: https://www.buzzsprout.com/1889238/episodes/18461238-he-sold-his-first-startup-for-100m-then-raised-250m-in-18-months-dileep-thazhmon-founder-of-jeeves.mp3
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Duration seconds: 3354

## Resource

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, ...

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