The pitch Sebastian Thrun made to investors in 2014 was an alluring one. Thrun—former head of Google X, the company’s top-secret skunkworks—had already raised over $20 million for his buzzy online-education startup, Udacity. Now he wanted more. He promised to profoundly disrupt education through online courses that put students through a warp-speed curriculum, matriculating them with university-level “Nanodegrees” earned in a fraction of the time.

The model was still unproven. “It was super aspirational. Lots and lots of unknowns,” said Gabriel Dalporto, who became Udacity CEO in 2019. But Thrun got his funding—and a roughly $200 million valuation. Andreessen Horowitz ponied up in the $35 million Series C, as did Columbus, Ohio–based Drive Capital and another firm far removed from tech’s coastal power centers: Atlanta-based broadband and media conglomerate Cox Enterprises.

Cox Enterprises, which is owned by a sprawling, eponymous clan of billionaires, has been placing a lot of bold bets over the past decade, posting at least 70 venture deals in that time and 40 in the past three years alone. In addition to its investment in Udacity—which hit a billion-dollar valuation in 2015 and has “nine-figure” revenue today, Dalporto said—Cox has quietly backed electric truck company Rivian; Caffeine, a promising livestreaming platform; FaZe Clan, an e-sports team that recently completed a SPAC deal; PadSplit, a housing marketplace app; Enlace Health, a maker of medical payments software; and Clearcover, a car insurance startup. Cox Enterprises’ existing digital portfolio also includes brands such as Autotrader, which it launched in 1999, and Dealertrack, financial software for car dealerships, which it acquired for $4 billion in 2015.