Episode
He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve
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- Feb 9, 2026
- Duration seconds
- 3136
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Summary
Jay was running a respectable AI startup with $3M ARR. But he knew it wasn't a venture-scale rocket ship. So, he decided to fire all his customers, pivot the entire company, and bet everything on a new vertical: legal AI for plaintiff attorneys. Eve went from zero to unicorn status in under two years, raising $100M at a $1B valuation. In this episode, Jay breaks down the brutal reality of pivoting a revenue-generating company, how to achieve "demo shock" in an antiquated industry, and w...