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
In an insightful discussion on 20VC with Harry Stebbings, Jean-Denis (JD), co-founder and CEO of Town.com and former CTO at Plaid, delved into the evolving landscape of AI assistants. JD positioned Town.com as a top-three priority in the AI assistant market, stating it operates as an AI assistant living within users' email and calendar, recommending and automating tasks they would typically do themselves. The company recently pivoted from an AI tax preparation business after realizing the potential of agentic models operating within daily communication platforms.
JD openly addressed the fierce competition, acknowledging that giants like Google and Apple view this space as a top priority. He views "moats" as a luxury for companies further along than Town.com, emphasizing the immediate need for deep product-market fit with a target of 100,000 to a million paying users. He believes the winning product will feature a network effect at the agent level, highlighting Town's "agent-to-agent" feature where assistants communicate to retrieve information, a concept he sees as a true differentiator. JD outlined several theories for moats in this space: custom models, personalized context data, and distribution channels, noting Meta/WhatsApp as a significant threat due to their existing user base.
The future of human-agent interaction, JD predicts, will involve trusting agents to decide what data to share with others, even without explicit rules. He argues that AI models will become more adept at respecting privacy boundaries than humans, citing examples of intra-company data sharing for business outcomes that currently seem "insane" but will become commonplace. He also suggested that while human oversight will remain crucial for setting goals and budgets for agents, the agents themselves will handle the bulk of execution and even monitoring, potentially leading to fewer errors than human-driven processes.
On the technical front, Town.com employs model routing, leveraging different models (e.g., Gemini, OpenAI, 11 Labs) based on cost-effectiveness and task requirements. JD noted that while consistency in user experience (like voice personality) limits "wild routing" for direct user interaction, pure reasoning tasks allow for more flexibility. He confessed that Town.com heavily relies on frontier models due to the complexity of custom workflows, accepting this as a necessary subsidy for growth, with the expectation that costs will decrease over time for many tasks. He stressed that their priority is maximizing product value and growth rather than immediate cost optimization.
JD shared insights on Town's "time to wow," crediting their high 15% payment conversion rate to the immediate value users experience by connecting their email and calendar, which enables personalized automation suggestions. He also revealed an unexpected product-market fit with families, particularly parents managing numerous school and children-related communications, despite their core focus being enterprise.
Addressing Apple's potential entry, JD expressed skepticism due to Apple's lack of cloud-native DNA and their commitment to on-device processing and strict privacy, which he believes lags behind the "frontier" of AI capabilities. He also touched on the broader concern of data leakage and cyber threats in an AI-driven world, likening it to the early days of chemical industries learning to manage risks.
When defining success, JD prioritized consistent monthly payments from users, indicating that sufficient value is being delivered. He contrasted the potential for long-term revenue growth in enterprise (where AI directly drives business value) with the more limited scope of consumer use cases, favoring a large base of users paying less over fewer paying more. He expressed excitement for the advancements in conversational AI and the potential for AI to dramatically reduce daily toil, foster innovation in various sectors, and ultimately lead to a more prosperous and fulfilling world.