Mr. Galanis, a 2010 Duke University graduate, recruited a fellow alumnus and software engineer, Devon Townsend, to build it. In the spring of 2017, the website BookCameo.com launched with a tweet from Mr. Marsh, promising videos for around $20; Tori Spelling and niche Vine personalities like Evan Breen joined later that year. (Mr. Blencowe, 37, and Mr. Townsend, 33, who are also co-founders, still work at the company.)

For Mr. Galanis, Cameo, based in his hometown, Chicago, felt like the company the trio was destined to build. He and Mr. Blencowe were fresh from a short-lived production career. (Mr. Galanis still highlights their IMDb credits, which include a TV show called SAF3, pronounced “safe,” about an elite rescue task force.) Mr. Townsend had been a star on Vine, the short-lived, short-form video app.

“We lived in this world,” Mr. Galanis said. “We didn’t build this business by accident.”

This article is based on interviews with Mr. Galanis and more than 30 current and former Cameo employees, investors and advisers as well as internal documents, screenshots and photographs.

Mr. Galanis sports a dark close-cropped beard and often wears either polos or Cameo-branded shirts and baseball caps. He’s a self-assured pitchman who views himself as an ultra-connector, peppering conversation with references to business leaders he admires like Elon Musk.

He pointed to a 13-year-old college newspaper profile of the events company he ran at Duke, with the headline “The Mayor of Main Street.” He said it offered “pretty important” context for why he was able to build Cameo. The article, which is topped with a photo of Mr. Galanis flashing a thumbs-up while drinking a Busch Light, describes how he made a name for himself by befriending local venues and organizing huge parties, like a beer-pong event that was viewed as innovative for taking place on a weeknight at Shooters, a spot that was normally a sweaty dance club with a cage. (He also took credit for an “April Showers” party, featuring coeds in wet T-shirts.)

Erin Griffith and Sapna Maheshwari

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