How I Turned an e-Sports Hustle Into a Startup With Celebrity Investors and Over $6 Million in Funding

Like many college students, Brandon Pitts, now 32, spent much of his time in undergrad playing Madden and NBA 2K. Unlike most of his peers, though, he managed to turn his avocation into a burgeoning e-sports empire. Since 2011, the entrepreneur has hosted local tournaments, where everyday players bet money on themselves in hopes of winning a grand prize. Last month, his company introduced software called 1/0S that allows anyone to host a tournament to benefit their own local club or organization through his company’s Tournament Partner Program. Here, Pitts explains how running an underground e-sports hustle in his younger days led him to create a series of tournaments hosted by real-world NBA players including Terry Rozier, Derrick Jones Jr., and Quinn Cook.

Growing up, the two things I used to do were play basketball and play video games. When I left home for college–I spent a summer at Texas Tech, then a semester at Oklahoma Panhandle State University, followed by a couple of years at South Plains College–I played both until I tore my ACL. Then it was just video games. 

My dorm room back then was the hot spot. I had the PlayStation and the Xbox, two TVs, all the controllers; all my basketball teammates and everybody else would come by at all hours to play games like Madden NFL, NBA 2K9. We used to huddle up in my room, play all night, sleep in class all day, and then do it all over again.

The room became like a mini e-sports casino. I was the matchmaker. You want to win some money playing Madden? Give me $50 before you play. I’ll match you up with someone else, take $5 from both sides, and make sure the winner gets paid. After a while, I was probably making $75 to $100 a day that way. Eventually, the dean at South Plains let me host a 32-player video game tournament in the school’s main common room. I pulled together four TVs, set up the matches, and made about $500. 

After my injury, I left school and went home to Cleveland. Shortly afterward, I joined a local pre-seed stage incubator called Shaker LaunchHouse and worked on starting up a business–Winner’s Circle Games. It was similar to what I did in college: I hosted video game tournaments and set up one-on-one matches, only now most of the action took place in hotel meeting rooms, and people found it all through word of mouth. As people got to trust me, and I was able to start setting up more matches online, both sides would PayPal me the money, they’d play each other from their own consoles at home, and I’d send the winner the money minus my cut. After a while, we even had a 1-800 number you could call to get a match: “If you want to play Madden on Xbox, press 1, if you want to play NBA 2K on PlayStation 4, press two,” and so on, and a website where you could check your balance. I set it up like it was this big corporation. Really, it was just me, doing almost everything manually. 

Most of Winner’s Circle was still an events business, and it was a lot of work–I’d be driving all over Cleveland transporting the systems and the TVs, setting them all up. At one point, someone robbed the LaunchHouse and took all my TVs. It was at that point I decided to head out to Silicon Valley, where I crashed on couches and ran the online part of Winner’s Circle on the road. 

I wasn’t sure what to do next, but I didn’t want to go back to driving all around Cleveland with TVs and Xboxes. I decided it would be better to keep everything mobile. I partnered up with a guy named Diego Aguilar, who had a product background at Google and Spotify. We built a mobile app and called it Play One Up: Users download it, find an opponent, and then pay in their money to the app, which holds onto it and pays the winner via PayPal at the end of the game (if opponents disagree about who won, they send us a screen grab proving it). All the matchups are streamed on Twitch. Since we launched the app in 2019, we’ve had 250,000 registered users bet more than $5 million against one another using the platform. 

On the basis of that progress, I raised $6 million, and even got some pro athlete investors involved, including Denzel Ward of the Cleveland Browns (his dad was a teacher in my junior high and had been a mentor) and Victor Oladipo of the Indiana Pacers (one of his trainers is a childhood friend). Last month, we announced our latest product, called 1/0S. Essentially, it gives people like me when I was younger everything they need to host an e-sports tournament: the software that makes the matchups, collects the entry fees, and even provides the support staff.