Photo: Art by Clark Miller.

In November 2021, just as crypto prices were hitting all-time highs, MoonPay—a crypto payments startup that celebrities including Jimmy Fallon and Paris Hilton had praised for its non-fungible token “concierge” service—announced it had completed its first ever outside fundraising: an eye-popping $555 million round at a $3.4 billion valuation from investors including Tiger Global Management and Coatue Management. There was more to the deal than met the eye.

MoonPay raised $405 million by selling shares to investors, and the remaining $150 million represented shares cashed out by insiders in a secondary transaction, meaning that money didn’t flow into the company’s coffers, according to a person familiar with the matter. The shareholders who sold included co-founder and CEO Ivan Soto-Wright, the person said.