Why a $1M Startup Wasn’t Worth Building in the Age of AI

Jean-Denis Greze was CTO of Plaid. His next startup, an AI tax product for small businesses, made nearly $1M in its first year and was on track for $2.5M to $3M. 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 partner Alex Rampell to say it “changed my life,” without knowing whose company it was. In this episode, Alex and Jean-Denis cover: - Why a profitable business can still be the wrong business to build - How to know when to kill something that’s working - 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 Timestamps: 00:00 Intro 00:56 Leaving Plaid for the SMB tax bet 06:57 Walking away from a working business 10:28 How Town was born 16:16 The iPhone moment for AI at work 23:22 Town as a token-allocation machine 29:10 Horizontal vs vertical 34:03 Why Town over OpenAI and Anthropic 44:32 Why AI is underhyped outside the Valley 52:33 Neutral agents and the broken ad covenant Resources: Follow Alex Rampell on X: https://x.com/arampell Follow Jean-Denis Greze: https://x.com/jgreze Learn more about Town: https://town.com Stay Updated: If you enjoyed this episode, be sure to like, subscribe, and share with your friends! Find a16z on X: https://twitter.com/a16z Find a16z on LinkedIn: https://www.linkedin.com/company/a16z Listen to the a16z Show on Spotify: https://open.spotify.com/show/5bC65RDvs3oxnLyqqvkUYX Listen to the a16z Show on Apple Podcasts: https://podcasts.apple.com/us/podcast/a16z-podcast/id842818711 Follow our host: https://x.com/eriktorenberg Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see http://a16z.com/disclosures.

Alex RampellhostJean-Denis Grezeguest

Oct 19, 20261h 1mWatch on YouTube ↗

EPISODE INFO

Released: October 19, 2026
Duration: 1h 1m
Channel: a16z
Watch on YouTube: ▶ Open ↗

EPISODE DESCRIPTION

Jean-Denis Greze was CTO of Plaid. His next startup, an AI tax product for small businesses, made nearly $1M in its first year and was on track for $2.5M to $3M. 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 partner Alex Rampell to say it “changed my life,” without knowing whose company it was. In this episode, Alex and Jean-Denis cover:
Why a profitable business can still be the wrong business to build
How to know when to kill something that’s working
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
Timestamps: 00:00 Intro 00:56 Leaving Plaid for the SMB tax bet 06:57 Walking away from a working business 10:28 How Town was born 16:16 The iPhone moment for AI at work 23:22 Town as a token-allocation machine 29:10 Horizontal vs vertical 34:03 Why Town over OpenAI and Anthropic 44:32 Why AI is underhyped outside the Valley 52:33 Neutral agents and the broken ad covenant Resources: Follow Alex Rampell on X: https://x.com/arampell Follow Jean-Denis Greze: https://x.com/jgreze Learn more about Town: https://town.com Stay Updated: If you enjoyed this episode, be sure to like, subscribe, and share with your friends! Find a16z on X: https://twitter.com/a16z Find a16z on LinkedIn: https://www.linkedin.com/company/a16z Listen to the a16z Show on Spotify: https://open.spotify.com/show/5bC65RDvs3oxnLyqqvkUYX Listen to the a16z Show on Apple Podcasts: https://podcasts.apple.com/us/podcast/a16z-podcast/id842818711 Follow our host: https://x.com/eriktorenberg Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see http://a16z.com/disclosures.

SPEAKERS

Alex Rampell
host
Partner at Andreessen Horowitz (a16z).
Jean-Denis Greze
guest
CEO and founder of Town; former CTO at Plaid.

EPISODE SUMMARY

In this episode of a16z, featuring Alex Rampell and Jean-Denis Greze, Why a $1M Startup Wasn’t Worth Building in the Age of AI explores why Town ditched SMB tax to build neutral AI work agents Jean-Denis Greze explains why he abandoned a technically successful SMB tax automation product: annual purchase cycles, weak word-of-mouth, and incumbent distribution made it unlikely to scale to venture outcomes.

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