What this bankruptcy says about AI startups

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After you win the economics Nobel, what would your first act be? Buy a Corvette? Gloat to your childhood bully? For co-winner Michael Woodford, his first act was … proctor an exam. The DAY that Columbia professor Michael Woodford found out that he and Robert Hall won the economics Nobel, he returned to his class with the pithy title “Cognitive Mechanisms and Economic Behavior” to administer an exam. He was welcomed to the classroom with cheers and applause. He held up his arms in triumph.

Michael Woodford, Columbia University professor and winner of the 2026 Sveriges Riksbank Prize in Economic Sciences in Memory of Alfred Nobel.

Andrew Harrer/Bloomberg via Getty Images


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Andrew Harrer/Bloomberg via Getty Images

Coming up:

  • Character.ai is going through bankruptcy. What can we learn from the AI startup’s decline? 
  • Why President Trump wants to import diesel fuel from Russia
  • Why stagflation was John Maynard Keynes’ Achilles’ heel

News We’re Watching

When AI startups get vacuumed up, what’s left behind?

What to know: Character.ai is a company that allows you to speak with a “companion” — an AI-powered fictional character, historical figure, or whatever you decide to build. It came out just before ChatGPT and quickly went viral in part thanks to its adoption on TikTok. It hit 28 million monthly active users at its peak.

Character.ai had a lot of engagement, a big customer base, lots of talent … and Google promptly picked ’em up for $2.7 billion back in 2024. But Google didn’t buy the company and absorb it! No, that traditional “acquihire“ model would require all sorts of legal and regulatory approvals. Instead, they hired away the founders (and other big hitters on the team) and bought the nonexclusive license to the technology, leaving the company itself behind. That’s called a “reverse acquihire,” and it’s happened at least six times in the past two years with AI startups. Now this week, Character.ai is filing for Chapter 11 bankruptcy.

Some of the “Characters” available to users

Some of the “Characters” available to users

Gabby Jones/Bloomberg via Getty Images


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Gabby Jones/Bloomberg via Getty Images

Why it matters: A “reverse acquihire” doesn’t leave a company in the greatest position. After the Google deal, Character.ai had to change its business model away from the quite costly LLM training and toward developing AI characters. Its founders were gone. Sure, the shrunken company had $2.7 billion in the bank, but leadership was still looking to raise money as they struggled to monetize their user base.

So is the “reverse acquihire” what caused the pain? Or was it a symptom of a larger issue? Character.ai faced a mountain of litigation over alleged harm to minors plus copyright concerns from Disney. So what’s left behind? A once very promising company, which Disney is very excited to pick over for parts of it for $20 million.

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