Matthias Balk | Picture Alliance | Getty ImagesFive years ago, venture capitalists were pouring money into American startups selling everything from lingerie subscriptions to scheduling software, anointing them with billion-dollar valuations before most even turned a profit.It was a frothy era for startups, fueled by a combination of cheap money and pandemic-boosted demand. But even after the Federal Reserve took some froth off by starting to raise interest rates in 2022, many founders believed that they could grow into their inflated valuations, investors told CNBC.Then, an app called ChatGPT arrived.”The ChatGPT moment was when people said, ‘Holy smokes, the next generation of entrepreneurs, their coding language is spoken English,'” said Samir Kaul, a partner at the venture firm Khosla Ventures, an early backer of OpenAI.”Now you’re seeing 50 engineers do what it would’ve taken 500 engineers to do five years ago,” Kaul said. “We had to completely reshuffle how we valued these companies.”While the shares of public software companies like Salesforce, ServiceNow and Workday got hammered this year because of the threat from artificial intelligence, a quieter reckoning has been unfolding in the private markets.The AI boom that funneled more than $250 billion into OpenAI and Anthropic ahead of their expected mega-IPOs this year has left hundreds of startups built before ChatGPT’s arrival in 2022 stranded — effectively cut off from venture funding because of their inflated valuations and outdated technology, yet not profitable enough for the public markets.There are 857 U.S. startups valued at $1 billion or more, the threshold for being deemed a “unicorn” company, according to PitchBook data. But nearly half of that group hasn’t raised fresh funding in the last three years, making those valuations stale, according to the private markets data firm. Startups that last raised in 2021 are now worth 68% less on average, while those that last raised in 2022 saw a 52% decline, according to Pitchbook’s own valuation estimates.As a result, more than 220 companies that had reached billion-dollar valuations in the venture boom are now fallen unicorns, according to PitchBook, which provided a list of the companies exclusively to CNBC. The estimates are based on factors including head count growth and comparisons with public companies. “A lot of those companies are pre-AI, not just in their cost structure, but also in their products,” Mercury CEO Immad Akhund told CNBC. His company, which raised $200 million in funding last month, provides banking services to a third of early-stage U.S. venture-backed firms.”They’re definitely in a difficult spot,” he said. “All the attention’s on AI, so if you’re not an AI-first company, you need really strong numbers to raise.”Glossier, Brooklinen, AG1The list of fallen unicorns includes well-known brands like Glossier, The Farmer’s Dog, Rothy’s, Brooklinen and Savage X Fenty, the lingerie company founded by musician Rihanna. The companies were part of a wave of direct-to-consumer firms built on the hope that digital retailers could earn software-like margins.Also included are mainstays of podcast advertisements including the powder supplement maker AG1 and the robo-advisor pioneer Betterment as well as the online ticket marketplace SeatGeek. These companies came of age in an environment that rewarded growth at nose-bleed valuations based on two broad assumptions: interest rates would remain low and a startup could always be acquired for its engineering talent.But the arrival of generative AI has redrawn the venture landscape, redirec …