Tolan raises $30M from Union Square Ventures, Khosla and Homebrew

Union Square Ventures, Khosla Ventures and Homebrew put up the new $30 million, which doubles the company's total funding. Tolan declined to share a valuation. The app is a subscription product built around a customizable character that helps with planning, budgeting, relationships and goals. Upstarts Media reports that annual recurring revenue more than doubled over the past year and now sits in the double-digit millions, with paid memberships driving the business. The company says its 30-day net user retention improved 115 percent year over year. The new capital will widen access through a first-ever free tier and support more capable features. For founders, Tolan is a consumer AI product with real subscription revenue and no enterprise sales motion. Retention and paid conversion are the metrics to watch, and emotional-support use cases carry product safety obligations that teams should plan for early.