The Pell Grant checks came quarterly. At South Plains College in Levelland, Texas, most of the basketball and football players were eligible for the subsidy money from the federal government in 2009. And what was left over after college costs, they wagered in Brandon Pitts’ dorm room. A 5'10" point guard on the basketball team, Pitts hosted any and all NBA 2K9 and Madden enthusiasts who wanted to play for cash. “We’d get that Pell Grant check, and that was the time to play for money because we all thought we were balling,” Pitts says. “Then people started throwing down a few hundred on a game, and it got kind of crazy.”
For some reason, the school let Pitts hold a 2K9 cash tournament in the common room of the dormitory for the first time that year. The first tournament was free. The second tournament cost each player $50. The winner took home $500, and Pitts cleared $1,000 before the cost of additional gaming systems and controllers. “I think the school was okay with it because it brought some campus unity,” Pitts says. “In college everybody was up to no good one way or another, but this was on campus, so it wasn’t dangerous.
“That was my light-bulb moment like, Oh s---, I could make money off of this.”
The big idea: Host Madden and 2K matchups for money online, and charge a rake. Pitts tore his ACL playing basketball the following year and never fully recovered. There were two failed attempts at game-hosting websites—abandoned after creative disputes and poor organization—then a breakthrough. Drawing on a legal team with experience in the online poker boom of the early 2000s and, later, the daily fantasy sports wave, Pitts took advantage of the shifting legal landscape in sports wagering and got his app, One Up, into Apple’s App Store this year.
Pitts says more than $1 million has changed hands on the app in the six months it’s been available, and he has secured more than $1.4 million in funding from various investors. A close friend, Anthony Wells, introduced Pitts to Celtics guard Terry Rozier, a partner and One Up’s biggest public-facing backer, who touts the site on Instagram. The company just opened its Series A round of funding.
One Up, based in Pitts’ hometown Cleveland, tried and failed eight times to get approved for the App Store. It’s chief competitor, playerslounge.co, has yet to do so. In the gaming community, the concept of wagering on outcomes is not new; several websites offer fans the opportunity to bet on pro gamers facing off in titles like Fortnite and Rocket League. But betting on oneself on a small scale (One Up offers the opportunity to wager between $5 and $5,000 on a single game of Madden, 2K or FIFA) is relatively uncharted territory.
Last month, Pitts hosted a handful of friends for an in-person 2K session for cash in the Cleveland office and posted updates on Instagram Live. Soon, gamers from across the Midwest were offering to drive to Cleveland to get in on the action. One of the top Madden gamers in the world, Serious Moe, based in Indianapolis, offered to make the road trip. The goal, Pitts says, is to provide an app experience that courts confident gamers like the friends in his office willing to drop several thousand dollars on a game, as well as novices wagering $5 to $10, with tiered play that prevents sharks from taking advantage of minnows.
The endgame? Possibly a partnership with or sale to an EA Sports or 2K, as long as gambling on sports in all its forms continues to gain mainstream acceptance.
“I think we have a ways to go—we want to continue to focus on building an amazing experience,” Pitts says, “but we do believe a company with more resources to expand this thing is within our vision.”
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