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

2026-09-07 · 71 min · 12 entities

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Episode description as stored

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?