Tolan raises $30 million for its AI companion as the category looks for trust

Tolan, the San Francisco startup behind an AI companion app of the same name, has raised $30 million. Union Square Ventures announced on October 19 that it is leading the round alongside existing investor Khosla Ventures; Upstarts Media also names Homebrew and reports that the round doubles the company’s total funding. Tolan declined to share its new valuation.

The company’s own figures are striking: about 250,000 monthly users, more than 70 million conversations over the past year, and annual recurring revenue in the “double-digit millions,” according to Tolan and its investors. Tolan told Upstarts that about 70% of its users are women and 40% are parents. Users talk to customizable characters with long-running memory, and the app increasingly handles chores such as meal plans and family logistics. TechCrunch notes the contrast with Character.AI, which recently filed for bankruptcy, and points to the risks of offering emotional support at all.

The pitch here is not romance but trust: a friend that slowly becomes an assistant. Whether that keeps attachment healthy, or simply makes it more useful, is the question investors are now paying to answer.