Cameo to the Moon, and Back

Kenny G opened a meeting with a saxophone serenade. Paula Abdul judged an “American Idol”-style talent contest. “Hamilton” cast members performed. Lance Bass was there, hanging out. And when Robert Van Winkle, better known as Vanilla Ice, sang his 1990 hit, “Ice Ice Baby,” flanked by 10-foot sparklers, he pulled the Sugar Ray frontman Mark McGrath onstage.

This was Cameopalooza 2021, a company retreat celebrating the meteoric rise of Cameo, an app and website where regular people could buy personalized videos from minor celebrities for as little as $1. Attendees feasted on seafood towers and fondue fountains at an upscale restaurant on the Chicago waterfront and partied into the night at a Hilton penthouse suite, where Jack Harlow, a TikTok-famous rapper, performed a private show.

Three hundred Cameo employees danced, took videos and basked in their good fortune to be a part of the Cameo “Fameo” — the company’s nickname for its employees and community of celebrities. They were on a rocket ship powered by D-list celebrities and pandemic loneliness.

The company was preparing to expand in every direction: crypto art, live events, merchandise, international; its co-founder and chief executive, Steven Galanis, now 35, was expert at straddling the line between business and pleasure. A former collegiate party promoter, he shared the lifestyle of Cameo’s celebrity talent, jet setting between parties, sporting events and luxury homes in Miami, Los Angeles, and Chicago. Cameo had just raised $100 million on the audacious ambition to pioneer the “connection economy,” landing a $1 billion “unicorn” valuation just a few years into its existence.

Now fueled by money from venture capitalists including SoftBank, the investor that powered so many of the previous decade’s frothiest start-ups, Cameo could be so much more than just a quirky, semi-ironic video greetings business. Mr. Galanis and his co-founders decided to build “one of the most important, beloved consumer companies of the generation,” as Mr. Galanis declared in a 2021 interview. “Something that can be as enduring as what Walt Disney did for the last century.”

Investors and employees — encouraged with a meme stock battle cry of “LFG!”(“let’s go!” with an expletive) — believed the company’s surging growth would continue forever.