The Twenty Minute VC (20VC) · Monday, September 7, 2026
Jean Denis (JD), founder of Town, discussed the company's pivot from AI tax preparation to an AI assistant that integrates with email and calendar. The initial venture into tax prep did not achieve sufficient product-market fit, leading to a strategic reset and focus on areas with high user engagement like email and calendar.
“Yeah, so we've spent a year building an AI tax company. Like, business tax prep with AI. We got to some product market fit, but not enough where it was gonna be a success. There's a thing like the truth is we failed the building a business that would be a good business.”
“One of the areas we just looked at is, why has no one built AI that operates out of email? Just, there's so many people in the world who run their business and their life out of email and calendar. We were like, why is no one built a good product there?”
“And the prototype, we built a quick prototype in a couple of weeks and it had product market fit almost immediately. So that was the pivot.”