AI Summary
5 min readJean-Denis Grez, former CTO of Plaid, spent a year building an AI-powered tax preparation tool for small businesses. The product worked. The business did not. Tax is sold once a year, has no word-of-mouth flywheel, and incumbents could copy the AI features faster than a startup could grab market share. So Grez and his co-founder shut it down. Within months, they launched Town, an AI assistant that lives inside email and calendar and now serves hundreds of thousands of users. The episode is a case study in how a founder recognized a dead end, pivoted into a horizontal platform bet, and is now racing to make AI useful for people who are not engineers.
The Tax Pivot: Why a Working Product Was Not Enough
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What you'll learn
- 1 (00:00) **Why Jean-Denis Left Plaid and Started a Tax Company** - The founder explains his initial post-Plaid exploration into using AI to automate SMB tax preparation.
- 2 (07:07) **The Pivot: Why They Walked Away from a "Good" Business** - The founder describes the difficult decision to abandon a working product because it couldn't scale.
- 3 (10:24) **The Insight That Led to Town** - The founder explains the simple question that sparked the new company: why hasn't anyone built a great AI agent for email and calendar?
- 4 (13:31) **PLG vs. Enterprise: The "Good" Trap** - The founder explains why they chose a product-led growth (PLG) strategy over enterprise sales, using a Blackberry/iPhone analogy.
- 5 (18:20) **The Adoption Journey: From Email to Core Systems** - The founder outlines the phased approach to getting AI adopted inside companies.
- 6 (21:23) **Defining the Market: It's Not "Assistants"** - The founder reframes the market from "executive assistants" to a much larger opportunity.
- 7 (24:43) **The "Iceberg Lettuce" Problem: A Concrete Use Case** - A detailed example of how Town can save a restaurant owner money by analyzing wholesaler price changes.
+ Full timestamped outline available in the app
Show Notes
Why hasn't AI transformed everyday work as quickly as coding? Town CEO Jean-Denis Greze argues the bottleneck isn't intelligence, but making AI useful to people who don't have the time or technical skills to build their own automations.
Jean-Denis joins a16z General Partner Alex Rampell to share why he pivoted Town from tax software to a personal AI assistant built around email, calendars, and the workflows that run businesses. They discuss why consumer-grade experiences may win in enterprise AI, how Town discovers and automates tasks users wouldn't think to delegate, and why model neutrality and data ownership matter as AI labs increasingly compete with application companies.
They also explore what happens when agents begin acting on our behalf, from managing everyday work to shopping and commerce, and why the next generation of software may need to adapt to each user rather than the other way around.
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
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