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: https://youtu.be/o_5f4N6Nq80 @jgreze @TownAI @arampell