Jean-Denis Greze built an AI tax product for small businesses that made nearly $1M in its first year and was tracking toward $2.5M to $3M. He shut it down anyway. Sitting with a16z partner Alex Rampell, Plaid’s former CTO explains why incumbents could automate tax prep for their existing customers faster than a startup could win share, and why a once-a-year sales cycle left roughly one month to pivot.
The pivot became Town, an AI assistant that works from email and calendar. It found product-market fit fast enough that Ben Horowitz told Rampell it changed his life without knowing whose company it was.
