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Town CEO Jean-Denis Greze Explains Why He Shut Down a Profitable AI Tax Startup

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The interview lays out a rare first-person account of killing a business that looked healthy on paper because AI shifts the moat toward incumbents with existing distribution. It also explores the awkward position of application startups that compete with OpenAI and Anthropic while paying them for tokens, and why the forward-deployed engineer model weakens as models improve. Founders weighing vertical AI plays and operators deciding when to pivot will find concrete decision frameworks, including how a US$1/month AI routine can save a restaurant thousands.

Jean-Denis Greze, former CTO of Plaid, built an AI tax product for small businesses that reached nearly US$1M in revenue in its first year, with projections of US$2.5M to US$3M the following year. He shut it down because he judged it could never reach venture scale, as incumbents could apply the same AI to automate tax prep for their existing customer bases faster than a startup could win share. Tax is purchased once a year, leaving roughly a one-month window to pivot. The pivot became Town, an AI assistant that works from a user's email and calendar, which grew fast enough that Ben Horowitz told a16z partner Alex Rampell it changed his life.

Image · a16z
Original · a16z

Jean-Denis Greze was CTO of Plaid. His next startup, an AI tax product for small businesses, brought in nearly $1M in revenue its first year, and he projected $2.5 to $3M the next. He shut it down anyway. The reason: in the age of AI, it was never going to be 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 also sold once a year, so he had about a one-month window to pivot before the door closed. The pivot became Town, an AI assistant that works from your email and calendar. It found product-market fit fast enough that Ben Horowitz messaged a16z's Alex Rampell to say it "changed my life." In this conversation, Alex and Jean-Denis cover: - How to know when to kill a business that's working on paper - Why Town competes with OpenAI and Anthropic, the companies it buys its tokens from - Why the "forward deployed engineer" model gets worse as AI gets better - How a $1/month AI routine can save a restaurant thousands - What agents mean for Amazon, advertising and the future of shopping 0:57 How Ben Horowitz discovered Town 2:20 Why Town started with AI tax prep 3:55 Why tax couldn't be venture scale 6:30 Shutting down a working business 10:24 The customer ask that became Town 13:35 Why Town built for users before IT 16:18 AI's iPhone moment at work 21:28 Jevons paradox for executive assistants 23:13 Town as a "token allocation machine" 28:00 How Town tailors itself to each job 34:03 Competing with your token suppliers 42:24 Staying off the AI labs' radar 44:42 Why AI isn't spreading evenly yet 52:32 How agents break the ad model 55:35 The friction humans actually enjoy 57:05 Why supply aggregators lose to agents YouTube: youtu.be/o_5f4N6Nq80 @jgreze @TownAI @arampell Your browser does not support the video tag. 🔗 View on Twitter 💬 19 🔄 5 ❤️ 65 👀 10570 📊 26 ⚡