Ex-Plaid CTO killed his $1M-revenue AI tax startup over venture-scale fears, pivoted to Town
a16z · x · 2026-10-19
In an a16z podcast, former Plaid CTO Jean-Denis Greze explains why he shut down his AI tax product for small businesses despite nearly $1M first-year revenue and a projected $2.5-3M the next year.
- In the age of AI, it was never venture scale: incumbents could use the same technology to automate tax prep for their existing customers faster than a startup could win market share.
- Tax is sold once a year, leaving roughly a one-month window to pivot before the door closed.
- The pivot became Town, an AI assistant working from your email and calendar, which found product-market fit fast enough that Ben Horowitz told a16z's Alex Rampell it "changed my life."
- The conversation covers when to kill a business that works on paper, and why Town competes with OpenAI and Anthropic — the very companies it buys tokens from.
Related event: Ex-Plaid CTO Shuts Down $1M-AI Tax Startup to Build Town(2 posts)→
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