Tiger Global markdowns include massive cuts to Bored Ape Yacht Club and OpenSea

The valuations of two notable crypto-related companies were cut by venture capital firm Tiger Global Management. Photo illustration by Fortune

Over the past few years, venture capitalists have poured hundreds of millions of dollars into the crypto darlings seen as the next big thing, but now the honeymoon phase is over.

One of the most notable VC firms, Tiger Global Management, has marked down its stake in Bored Ape Yacht Club and OpenSea by 69% and 94%, respectively, since investing in the companies, Bloomberg reported. The firm, which manages about $50 billion, recorded an 18% paper loss in its biggest fund at the end of September amid the markdowns, according to people familiar with the matter cited by Bloomberg.

Tiger Global did not immediately respond to Fortune’s request for comment.

Crypto startup valuations have been plummeting on the books of several VC firms. Last month, Coatue Management, a major investor in NFT marketplace OpenSea, marked down the value of its stake by 90%, according to The Information. The markdown puts the company at a $1.4 billion valuation on paper, compared with $13.3 billion last year.

OpenSea has been among the companies particularly hard-hit by a pullback in crypto and NFT trading. Its revenue is a fraction of what it was in previous years, and in early November the company laid off about 50% of its employees as CEO Devin Finzer promised a reorganization around what he called “OpenSea 2.0.” Days later, Fortune reported that about half of the remaining employees set off on a two-week company retreat at a $9 million West Hollywood mansion once owned by Katy Perry and ex-husband Russell Brand.

Investment in the crypto space came in at about $1.8 billion in the third quarter, down 28.3% from the previous quarter, according to TechCrunch.

Compared with the frothiness of 2021, valuations, especially for companies in the median growth category, have also come back down to earth, Fortune reported. Venture capital investors have more leverage as capital dwindles across sectors such as crypto, and some are using it to demand more for their investment.

Still, as investor optimism is building on the hope that the Securities and Exchange Commission will soon approve a spot Bitcoin ETF, crypto prices have seen a resurgence. Bitcoin has for weeks been teetering on the edge of $40,000, a price it has not hit since April last year. The coin was trading up 1.4% at $38,200 on Friday morning.