Fubo Gaming (formerly unnamed sports betting platform)

Sam Ratner was 18 years old, living in his mom's house, working from Lifetime Fitness and Starbucks, when he decided to build a company. He'd already tasted entrepreneurship: as a teenager in high school, he ran a snow removal business with his friend Ilya Fedorovich, doing $50-60k per winter, financing trucks, and learning the fundamentals of business. That experience gave him confidence he could scale something big.

But small-margin businesses didn't interest him. "If it's easy, there's no value," he explains. "If anyone could get into it, there's inherently zero value long-term." So when he heard whispers about the government potentially legalizing online sports betting nationally, he didn't jump in immediately. Instead, he spent hours writing out how he thought the market would evolve.

His analysis concluded that while DraftKings and FanDuel might get early traction through fantasy sports audiences, the market would eventually be dominated by either brick-and-mortar casinos or media companies like ESPN. The tech, however, was ancient—overseas systems from the early 2000s, rebuilt minimally for mobile. No native iOS apps. No good APIs for ticketing or merchandising.

Sam's insight: build the platform the right way, mobile-first, with modern architecture. Then call the big players and offer them a better deal than paying massive rev shares for outdated Swedish software.

He dropped out after intentionally failing his finals (so returning to college wouldn't be an option). Living at his mom's, he worked in coffee shops and a gym yoga studio, where he set up a semi-permanent desk setup. He funded the company on credit cards. "I didn't want to do anything but spend every waking moment on the business," he says. "So I just opened credit cards."

Sam didn't start by selling to DraftKings or FanDuel. Instead, he directly approached the NBA and MLB. At 19, with no authority and no track record, he somehow convinced the leagues to grant him authorized gaming operator status. "I think they thought I was crazy and kind of cool," he says.

He made it work by putting pieces in place that gave them confidence: he raised capital from venture funds in sports, media, and entertainment that the leagues already knew. He hired lawyers who represented ESPN and other major sports companies. Suddenly, he wasn't just "some crazy kid"—he was "a crazy kid with people we know."

Within 18 months, Sam had built the platform, secured league partnerships, obtained gaming licenses in 17+ states, and achieved compliance. He had something nobody else had: authorized market access to the NBA and MLB.

But Fubo TV saw what he'd built and wanted it more than he wanted to launch it himself. They called. He'd spent the time and capital building infrastructure that big public companies didn't want to touch—regulatory complexity, legal headaches, capital requirements. Fubo was willing to pay for that. At age 23, he sold for $40 million.

Sam kept most of the money in the market, using it as collateral for margin loans rather than selling stocks and creating tax events. He's since become fascinated by unconventional business opportunities: he bought a decommissioned riverboat casino in Iowa (for under $1 million) and spent a year exploring how to reposition it. He analyzed a vending machine business in rural Idaho that was doing triple margins compared to others, flying out to understand why. He investigated a water taxi business at Lake of the Ozarks that was generating $400k per boat per summer.

He didn't pursue any of these. His bar is high: "I had no interest in if it couldn't be worth at least a billion dollars in five years." But his ability to do deep diligence, fly to strange places, talk to old men at junkyards, and see patterns others miss—that's made him someone investors and entrepreneurs want to know.