He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve

Episode notes

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 why 4-hour user sessions were the first sign that he had struck gold. Why You Should Listen How threatening to shut down your product can reveal PMF. Why firing all your existing customers might be the only way to scale. How to achieve a 40% conversion rate from cold outreach to demo. Why you should target mid market instead of enterprise if you want to deploy AI fast.