Andrew spent two and a half years selling AI contract review to lawyers. It stalled at $800K. He rebuilt the company around finance teams and grew that to $10M. Then he demoed a little internal tool on the side at his own conference, and nobody wanted to talk about anything else. It did $350K in five weeks. He sold the $10M business and went all in on the side tool—Within went from zero to nearly $20M in 18 months.

In this episode, Andrew breaks down the 30-and-100 rule he uses to validate every idea, how he turned every customer conversation into a database that tells him what to build next, and why nine out of ten experiments have to fail.

Why You Should Listen

Why 30 conversations validate an idea and 100 customers reveal product market fit.
Why the thing everyone asks about matters more than the thing you launched.
How to tell that slow growth is a market problem, not a go-to-market problem.
How to run four bets a quarter with a kill metric on every one.

Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Within, Klarity, Andrew Antos, enterprise AI, AI transformation, pivoting a startup, enterprise sales, legal tech, finance automation, AI agents, customer discovery, voice of customer

Chapters

00:00:00 Intro
00:02:04 The Side Tool Everyone Wanted
00:04:26 $350K in Five Weeks
00:05:42 AI for Lawyers Before AI Worked
00:12:44 Stuck at $800K
00:13:43 Choosing Finance Over Legal
00:17:40 The 30 and 100 Rule
00:24:59 Selling the $10M Business
00:32:17 Building a Company Data Brain
00:40:01 Nine of Ten Bets Fail

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

He sold his $10M business to bet on a side app—then grew it to $20M ARR. | Andrew Antos, Co-Founder & CEO of Within

A Product Market Fit Show | Startup Podcast for Founders

He sold his $10M business to bet on a side app—then grew it to $20M ARR. | Andrew Antos, Co-Founder & CEO of Within