He Left Plaid at 45 to Become a Founder for the First Time. — Jean-Denis Greze (Town)
Automate Compliance (and get $1,000 off!!) - https://vanta.com/lubaToday I walk with Jean-Denis Greze, co-founder and CEO of Town, an AI on-ramp platform for knowledge workers. Jean-Denis is the former CTO of Plaid, led engineering through a blocked $5.3B Visa acquisition, and walked away from the C-suite at 45 to start over from zero, and now he's turned a scrapped AI tax-prep startup into a $55M Series A company backed by Andreessen Horowitz. He gets into the week he decided to kill a business that was actually working, and why he refuses to call Town an "AI assistant."
We get into:
- Why he waited until 45, after seven years as Plaid's CTO, to become a founder for the first time
- The week he and his co-founder killed a working, revenue-generating tax-prep startup because it wasn't going to be a rocket ship
- Town's real bet: not a smarter AI assistant, but an onboarding layer that gets normal people leverage from AI without writing a single prompt
- His "accelerators, table stakes, foundations" framework for staying ahead of OpenAI, Gemini, and Google
- Why turning "uncool" work into cult culture, from Dropbox's Team Cash to Plaid's colorful tights, built teams that stuck around
So much more!
Timestamps:
00:00:00 Trailer
00:00:43 Intro
00:01:41 Leaving Plaid at 45 to become a founder
00:06:01 Redefining success beyond IPOs and revenue
00:11:56 The YC prodigy myth VS two decades of hard-earned instinct
00:19:47 The stress gap between being an exec and being the founder
00:25:35 Time-boxing family, health, and friends at Series A
00:32:11 Betting on AI tax prep and grinding for a year
00:38:13 The week they decided to shut down a profitable business
00:41:53 The worst three weeks: telling the team and winding down right
00:57:47 The accidental prototype that became Town
01:04:15 Why Town calls itself an on-ramp, not an AI assistant
01:12:29 Beating OpenAI, Gemini, and Google's home-field advantage
01:20:31 Team Cash: making "uncool" work fun at Dropbox and Plaid
01:32:02 Landing Andreessen Horowitz and Forerunner for the Series A
01:37:41 Outro
Follow Jean-Denis
LinkedIn: linkedin.com/in/jeandenisgreze
X: https://x.com/jgreze
Website: https://town.com
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