Tolan raises $30M for its AI companion as active users pass 250,000

Tolan, an AI companion app built to help people manage daily life, relationships and emotions, has raised another $30 million. Union Square Ventures, Khosla Ventures and Homebrew participated in the round, which doubles the total capital the startup has raised to date.

Tolan did not disclose its new valuation, though it had already crossed $120 million previously. According to a report by Upstarts Media, PitchBook estimates the company is now worth more than $268 million, at medium confidence.

The product is reached through a cartoonish character that offers support and helps users get through their to-dos. That avatar-first entry point has become the standard shape for consumer companions, and it is also what makes the category easy to mock when it misses.

Revenue comes from tiered memberships that are required for full access to all features. Tolan told Upstarts Media its annual recurring revenue is now in the double-digit millions, a modest but real number for a consumer subscription app in this space.

The traction numbers are the strongest part of the pitch: more than 250,000 active users and more than 70 million conversations over the past year, with about 70% of users women and 40% parents. The app is said to appeal particularly to neurodivergent people, who may benefit from extra help with emotional support or organizing tasks.

The category's track record is uneven. Friend's pendant-based companion was publicly mocked as very cringe, and Character.ai filed for bankruptcy after its founders returned to Google. Against that backdrop, Tolan is seen as having found a balance between being helpful and not being perceived as too weird.

Competition is arriving from agents rather than companions. Meta gave its AI agent Muse a cute avatar and plans to release it as a hardware product, while task-oriented agents are competing for the same daily-planning use cases that Tolan targets.

The risks are concrete. Multiple lawsuits against general-purpose AI app makers allege that chatbot interactions contributed to users' suicides, and the boundaries of AI emotional support are still being redrawn. Watch whether subscription revenue can support the new valuation — and whether Tolan can stay on the useful side of both companionship and agency.