Tolan, an AI companion built to assist users with everyday tasks, relationships, emotions, and personal goals, has secured an additional $30 million in funding. The latest round was backed by Union Square Ventures, Khosla Ventures, and Homebrew, effectively doubling the total capital the startup has raised so far. According to a new report by Upstarts Media, the new funding pushes Tolan's valuation past its previous $120 million mark. While the startup did not confirm its new valuation, PitchBook estimates it at over $268 million with "medium confidence."

Users interact with Tolan's app through a cartoon-style character designed to provide encouragement and help them work through their daily to-do lists.

Tolan earns money through tiered membership plans, which are necessary for accessing the full range of features. The company told Upstarts Media that its annual recurring revenue has reached the "double-digit millions."

The startup stands out as one of the few AI companions that has gained meaningful traction, reporting over 250,000 active users who have engaged in more than 70 million conversations over the past year. According to Tolan's team, roughly 70% of its users are women and 40% are parents. Anecdotally, the app is said to hold particular appeal for neurodivergent individuals, who may benefit from extra support—whether emotional or organizational.

Compared with other AI companions, Tolan appears to have struck a balance between being genuinely useful and avoiding the perception of being too strange. Contrast that with the public backlash faced by Friend's pendant-based AI companion: users called Friend "very cringe," The New York Times described it as "hated," and Wired said it "has no soul."

Meanwhile, another former leading competitor in the space, Character.ai, recently filed for bankruptcy following its founders' return to Google. The remaining staff is transitioning to Disney, which acquired some of the company's assets.

However, Tolan may encounter growing competition from newer AI agents that help users plan, organize, and complete tasks and goals—not just talk through them. Meta, for example, gave its AI agent Muse a cute avatar for users to converse with and plans to release it as a hardware product in the future. The startup must also contend with the risks associated with providing AI-powered emotional support, particularly as multiple lawsuits have been filed against general-purpose AI app developers alleging that chatbot interactions played a role in users' suicides.