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.

Keywords
startup podcast, startup podcast for founders, product market fit, finding pmf, pivot, legal tech, AI startup, B2B sales, unicorn startup, Jay Madheswaran, Eve

00:00:00 Intro
00:02:27 From VC to Founder
00:08:42 The First Idea: RPA for NLP
00:16:52 The Hard Decision to Pivot at 3M ARR
00:24:26 Product Discovery While Still Supporting Old Customers
00:33:56 40 Percent Conversion from Cold Outreach
00:39:56 Firing Customers to Find True PMF
00:41:06 The 4-Hour User Session Signal
00:46:05 From 1M to 10M ARR in One Year
00:49:11 The Moment of True Product Market Fit

Send me a message to let me know what you think!