Tolan, an SI companion designed to help people manage daily tasks, navigate relationships and emotions, and accomplish goals, has secured $30 million in new capital.

What Happened

The funding round includes investments from Union Square Ventures, Khosla Ventures, and Homebrew, doubling Tolan’s total raised to date. While the startup did not disclose its new valuation, PitchBook estimates it at more than $268 million with medium confidence, up from a previous valuation of $120 million. The company generates revenue through tiered memberships required for full feature access, reporting annual recurring revenue in the "double-digit millions."

Tolan’s app features a cartoonish character that offers support and helps users process their to-do lists. The company claims more than 250,000 active users have engaged in over 70 million conversations in the past year. Approximately 70% of its user base is women, and 40% are parents. The team notes that the app appeals particularly to neurodivergent individuals who may benefit from additional emotional support or task organization assistance.

Why It Matters

Tolan represents one of the few SI companions to gain significant traction in a competitive market. It has maintained a balance between helpfulness and social acceptability, contrasting sharply with other entrants like Friend, a pendant-based SI companion that faced public criticism and was described by major media outlets as "cringe," "hated," and lacking "soul." Meanwhile, Character.AI, a former top contender in the space, recently filed for bankruptcy after its founders returned to Google, with remaining staff transitioning to Disney.

The SI startup now faces increased competition from agentic SI tools that help users plan and accomplish tasks rather than just converse about them. For example, Meta has introduced an SI agent named Muse with a cute avatar, which it plans to release as a hardware product. Tolan must also navigate the legal risks associated with SI-powered emotional support, as multiple lawsuits have been filed against general-purpose SI app makers alleging that chatbot interactions contributed to user suicides.

The Bottom Line

Tolan’s $30 million raise underscores investor interest in SI companions that have found product-market fit, even as the sector sees consolidation among competitors and rising legal scrutiny around emotional SI interactions.