The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

20VC: The $100 Billion AI Assistant Race: Town vs Instinct vs GrokBot | We Spend $75K Per Engineer on AI Tools | Why the AI Assistant Market Is Not a Bubble & AI Assistants Will Replace Every App on Your Phone with JD, Founder of Town

September 7, 2026

AI Summary

5 min read

The AI Assistant Race: Why JD Thinks Town Can Win

JD, founder of Town, started his company building AI tax software. It failed. So he and his team spent three months in the wilderness and emerged with something completely different: an AI assistant that lives inside your email and calendar, watches what you do, and quietly automates the repetitive work. The prototype had product-market fit almost immediately. That was late 2023. Now Town is three months into public launch, and JD is navigating a market he describes as moving faster than anything he has ever seen.

What Town Actually Does

Town connects to your email and calendar and recommends automations based on your actual behavior. If you tend to send the same kind of reply to certain emails, Town notices and offers to do it for you. If you schedule the same type of meeting repeatedly, it learns the pattern. The product is deliberately opinionated: you cannot use Town without connecting email and calendar. About 30% of new users drop off at that point, but the ones who stay convert to paying customers at a rate above 15%, which JD calls extremely high for a product-led growth model.

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What you'll learn

  • 1 (04:30) **What Town Is and How It Works** - JD defines Town as an AI assistant that lives in your email and calendar, recommending automations for tasks you already do.
  • 2 (05:18) **The Pivot from Tax to AI Assistant** - JD explains why he abandoned an AI tax company to build Town instead.
  • 3 (07:00) **Cannibalization Threat from Big Tech** - JD addresses whether Google, Apple, and GrokBot will kill Town before it scales.
  • 4 (08:40) **The Real Moat: Network Effects at the Agent Level** - JD identifies agent-to-agent communication as Town's key defensibility.
  • 5 (09:56) **The Distribution Threat from Meta and WhatsApp** - JD names his most worrying competitor by distribution advantage.
  • 6 (10:57) **One Agent vs. Multiple Agents** - JD predicts how many AI assistants each human will use.
  • 7 (13:03) **Trusting Agents with Data Sharing** - JD envisions a future where agents decide what information to share with other people.

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Show Notes

Jean-Denis "JD" Grèze is the Co-Founder and CEO of Town, the AI work assistant reportedly in talks to raise funding at a $1BN valuation. Before founding Town, JD spent seven years as CTO of Plaid. Before Plaid, he was Director of Engineering at Dropbox. He is also a prolific angel investor backing companies including Modal, BaseTen, Merge and NexHealth.

AGENDA:

00:00 Why AI Assistants Are Silicon Valley's Hottest Market
07:00 How Does Town Compete With Grokbot, Instinct and Big Tech?
11:00 Will We Have One AI Agent or Different Agents for Every Part of Our Lives?
17:00 How Many Mistakes Can AI Agents Make Before We Stop Trusting Them?
20:00 How Does Town Choose the Best Models Without Destroying Its Margins?
29:00 Is the AI Assistant Market Already Too Crowded?
37:00 Can Apple Win the Agent Race—and Are We Entering a Cybersecurity Nightmare?
41:00 What Does a Successful Town User Look Like—and Which Pricing Tier Makes Money?
47:00 What Will AI Agents Be Able to Do in Three Years That They Cannot Do Today?
54:00 Is the Skepticism Around Billion-Dollar AI Assistant Companies Justified?
58:00 What Needs to Happen for Town to Become a $100BN Company?
1:02:00 How Has AI Changed Hiring—and Why Does Town Spend $75K Per Engineer on AI Tools?
1:06:00 What Is JD Most Excited About Over the Next Decade?

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