Ramp raises $2 billion while Character AI files for bankruptcy

The venture capital landscape is showing stark contrasts in valuation and sustainability, exemplified by the simultaneous successes and failures of Ramp and Character AI. Ramp, a provider of digital accounting and expense management for small and medium businesses, raised nearly $2 billion in a new funding round. The round was led by Dragoneer, Thrive Capital, and Founders Fund, valuing the company at $60 billion. With estimated revenue between $1.5 billion and $2 billion, Ramp commands a 30-to-40x revenue multiple. Analysts attribute this premium to the strategic value of Ramp’s data on enterprise AI spending, which offers investors a potential control point to monitor and influence AI adoption, a dynamic similar to Stripe’s acquisition of OpenRouter.

In contrast, Character AI, a consumer companion chatbot that was a top app in 2024, has filed for bankruptcy, discharging between $50 million and $100 million in liabilities. The company faced significant legal challenges, including lawsuits over customer self-harm and a 2025 dispute with Disney over unlicensed characters. Disney has emerged as the leading bidder to salvage assets, agreeing to pay $20 million for certain intellectual property and hiring Character AI’s CEO, Colin Adams, to facilitate technology transfer. An affidavit from Adams revealed that Character AI spent $10 million per month on compute, while peak monthly subscription revenue was $2.8 million, with some months dipping below $1 million. Character AI’s last funding round in March 2023 was $200 million at a $1 billion valuation. 404 Media cited these figures to argue that AI economics do not work, a view dismissed by critics like John Katman, who characterized the failure as specific to Character AI’s business model rather than the industry as a whole. The bankruptcy marks the end of an early consumer AI phase, highlighting the difficulty of monetizing roleplay chatbots despite high user engagement.