Tolan, an AI companion app that helps people manage daily life, emotions, relationships, and goals, has raised another $30 million, according to a report by Upstarts Media. Union Square Ventures, Khosla Ventures, and Homebrew joined the round, which doubles the total amount the startup has raised and moves its valuation above the previous $120 million. Tolan didn’t disclose the new valuation; PitchBook estimates it at more than $268 million with medium confidence.

Users interact with a cartoonish character offering support and helping them get through to-dos. The app monetizes through tiered memberships required for full feature access; Tolan told Upstarts Media its annual recurring revenue is in the double-digit millions. The startup claims more than 250,000 active users and over 70 million conversations in the past year. Around 70% of users are women and 40% are parents, and the team says the app is anecdotally particularly appealing to neurodivergent people who may benefit from additional emotional or organizational support.

Tolan‘s traction stands out in a category where other AI companions struggled publicly. Friend’s pendant-based product was widely mocked—’very cringe’ to users, ‘hated’ per The New York Times, ‘has no soul’ per Wired—while Character.ai, a former top contender, filed for bankruptcy after its founders returned to Google, with remaining staff transitioning to Disney.

Still, the article flags two pressure points. Newer AI agents, which don’t just converse but help plan, organize, and execute tasks, could compete directly; Meta’s Muse, for example, pairs a cute avatar with plans for future hardware. And like other AI-powered emotional support apps, Tolan faces legal risk: multiple lawsuits have been filed against general-purpose AI app makers over chatbot interactions allegedly contributing to users’ suicides.