Plaid's Ex-CTO Killed a $1M ARR AI Tax Startup, Then Built Town
a16z · youtube · 2026-10-19
On the a16z podcast, Jean-Denis Greze (former Plaid CTO) explains why he shut down his AI tax product for SMBs despite $1M first-year revenue trending toward $2.5–3M: in the AI age it was never venture scale, since incumbents could apply the same tech to existing customers faster than a startup could win share — and with tax sold once a year, he had about a month to pivot. The pivot became Town, an AI assistant working from your email and calendar, which impressed Ben Horowitz before he knew whose company it was. Also covered: competing with OpenAI/Anthropic for tokens, why the forward-deployed engineer model worsens as AI improves, and what agents mean for Amazon and advertising.
Related event: Ex-Plaid CTO Shuts Down $1M-AI Tax Startup to Build Town(2 posts)→
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