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Town vs Instinct vs GrokBot | Why the AI Assistant Market Is Not a Bubble

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. ----------------------------------------------- Timestamps: 00:00 - Intro 02:08 - Why Town Pivoted From AI Tax to AI Assistants 04:09 - Can Town Survive Google, Apple and OpenAI? 06:14 - Why AI Assistants Could Have Network Effects 08:48 - Will Everyone Have One AI Agent or Many? 11:01 - Will We Trust AI Agents With Our Private Data? 17:16 - Are Goal-Seeking AI Agents a Feature or a Bug? 19:30 - How Town Chooses Between OpenAI, Anthropic and Open Models 22:33 - Can AI Assistant Economics Ever Reach SaaS Margins? 25:05 - Open Models vs Frontier Models: Who Gets the Workloads? 29:56 - How Should VCs Invest in the AI Assistant Race? 33:45 - Why AI Startups Can No Longer Outrun Their Competitors 39:31 - Why Apple Could Lose the AI Assistant Race 41:50 - Are AI Agents Creating a Cybersecurity Time Bomb? 43:42 - Why Token Maxing Is the Wrong AI Metric 47:46 - Consumer vs Enterprise AI: Where Does the Bigger Business Get Built? 50:06 - Is ElevenLabs Worth $22BN? 51:57 - The Biggest Risk to AI Assistant Margins 01:00:01 - Is the AI Assistant Hype Justified? 01:03:41 - Quick-Fire Round ---------------------------------------------------------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on X: https://twitter.com/HarryStebbings Follow JD on X: https://twitter.com/jgreze Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #ai #founder #town #ceo #instinct #grok #aiassistant

Jean-Denis "JD" GrèzeguestHarry Stebbingshost
Sep 7, 20261h 16mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Why AI assistants will win: networks, trust, and cost curves

  1. Town pivoted from an AI tax product to an email-and-calendar-native AI assistant after prototypes showed immediate product-market fit as models became more agentic.
  2. JD believes the assistant category is not a bubble because a winning product could become the primary interface to digital work, but the market is still early and mainstream PMF is not yet fully solved.
  3. He expects durable moats to come less from model advantage and more from multi-user agent network effects, accumulated integrations/context, and strong product opinions about human–assistant relationships.
  4. Economically, the big uncertainty is what fraction of tasks will remain at the frontier (expensive, supplier-controlled) versus shifting to cheaper/open models, which determines whether margins can approach SaaS-like profiles.
  5. The next wave of risk and opportunity is trust: agents will handle more autonomous actions and data sharing, creating both massive productivity upside and heightened cybersecurity/privacy stakes.

IDEAS WORTH REMEMBERING

5 ideas

The winning AI assistant may be the one with agent-to-agent network effects.

Town’s current defensibility thesis is that assistants become more valuable when they can securely collaborate across coworkers (e.g., one person’s “townie” asking another’s for an answer), creating switching costs that single-user assistants don’t have.

Users will prefer a small number of front-door agents, with specialist agents hidden in the stack.

JD argues you won’t want a different agent per app; instead you’ll have 1–3 “entry points” shaped mainly by data separation (personal vs work) and privacy/compliance needs, while specialist systems sit behind the scenes via tool/model routing.

Trust will shift from humans manually gating data to agents autonomously managing disclosure.

He predicts agents will increasingly act as privacy filters—deciding what to share and what not to—similar to how humans mentally arbitrate sensitive vs appropriate information today, but with fewer mistakes than people make (e.g., accidental reply-all, leaking spreadsheets).

Model routing is constrained as much by user-perceived personality consistency as by raw capability or cost.

Town routes across providers (OpenAI/Anthropic/others; ElevenLabs for voice) to optimize for ROI, but consistency of “personality” and UX can limit routing because users notice tone/verbosity changes and perceive it as quality regression.

The core margin risk is the share of workloads that remain frontier—where suppliers set prices and may compete directly.

Like many AI apps, Town is mostly using frontier models today; JD expects many tasks (email labeling, routine scheduling, repeated workflows) to migrate down the cost curve to cheaper/open models, but the unknown is what % stays “frontier,” which determines whether margins can resemble SaaS.

WORDS WORTH SAVING

5 quotes

You can build now at the speed of machines, but you can only learn at the speed of humans.

Jean-Denis "JD" Grèze

I know what I'm building is a top-three priority at Google and Apple, like, in the next 12 months. Not a top-10 priority, like a top-three priority.

Jean-Denis "JD" Grèze

I think you'll trust your agent to decide what data to share with other people without you intervening in five years.

Jean-Denis "JD" Grèze

The product in this category that will win will have a network effect at the agent level.

Jean-Denis "JD" Grèze

We've passed the point where humans will read every line of code. That is never happening again.

Jean-Denis "JD" Grèze

Town pivot from AI tax to assistantsEmail/calendar as the assistant “home”Big Tech competition (Google, Apple, OpenAI, xAI/Grok)Agent-to-agent collaboration and network effectsSingle vs multiple agents; privacy-driven data silosTrust, data sharing, and autonomy boundariesModel routing, personality consistency, and voice stacks (ElevenLabs)

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