Tolan Raises $30M, PitchBook Values AI Companion at $268M

By Olivia Hart

Tolan has raised $30 million in fresh capital, and PitchBook estimates the AI companion startup's valuation at more than $268 million — more than double its previous $120 million mark. Union Square Ventures, Khosla Ventures and Homebrew participated in the round, which doubles the company's total funding to date, according to a report by Upstarts Media. Tolan itself did not disclose its new valuation, a gap worth noting given PitchBook attached only "medium confidence" to its figure.

The company told Upstarts Media its annual recurring revenue now sits in the "double-digit millions," generated through tiered memberships that gate full access to the app's features. No precise revenue figure, growth rate or churn data was disclosed.

Who uses Tolan?

Users interact with Tolan through a cartoonish character designed to offer support and help them work through their to-dos, relationships, emotions and goals. The startup claims more than 250,000 active users who have held more than 70 million conversations over the past year — roughly 280 conversations per active user, or close to one a day on average.

Around 70% of its users are women, and 40% are parents, Tolan's team told Upstarts Media. Anecdotally, the app is said to appeal particularly to neurodivergent people, who may benefit from added emotional support or help organizing tasks. These user figures come from the company itself; no independent verification was cited.

How does Tolan avoid the AI-companion backlash?

Tolan appears to have struck a balance between helpful and unsettling, at least compared with rivals. Friend, the pendant-based AI companion, drew public shaming: users dubbed it "very cringe," The New York Times called it "hated," and Wired said it "has no soul."

Character.ai, once a top contender in the space, recently filed for bankruptcy after its founders returned to Google. Its remaining staff is transitioning to Disney, which bought some of the company's assets.

That contrast is Tolan's clearest argument for durability in a category littered with failures.

What comes next?

Two risks temper the funding story. First, competition: a newer crop of AI agents helps users plan, organize and accomplish tasks rather than just talk through them. Meta gave its AI agent Muse a cute avatar for users to talk to and plans to release it as a hardware product in the future.

Second, liability: multiple lawsuits have been filed against general-purpose AI app makers alleging that chatbot interactions contributed to users' suicides. Tolan positions itself as an emotional companion, which places it adjacent to that litigation risk.

The $30 million gives Tolan runway, not immunity — its valuation surge rests on unaudited user counts and a revenue range the company chose not to narrow.