The Luba Show

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Today I walk with Jean-Denis Greze, co-founder and CEO of Town, an AI on-ramp platform for individuals and businesses. 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