After graduating fromN.C. State's computer engineering graduate program, he took a job with a risky start-up company.
A few years later, he and a classmate created a software company called Stingray. Three years later, they sold it for more than $20 million.
"The initial gut reaction is to go out and get the fancy Porsche and all that kind of stuff," he says. "But I've kind of resisted that and tried to stick to my roots, my upbringing, of just kind of keeping my life simple and relaxed and not overdoing it with really expensive items."
Rolling in cash, but still wearing his T-shirt and jeans, Wingo did not slow down.
His love of Star Wars and interest in online auctions spawned a business idea that has bitten the industry.
"There's Web search engines, so you don't have to check eight or nine Web pages a day," he says. "Why aren't there auction search engines for doing the same thing?"
AuctionRover.comis a dog that hunts for bargains. Within eight months of its debut, GoTo.Com announced it would acquire Rover for about $200 million in stock.
"I guess one misperception is -- it's not like you've won the lottery. You don't get cash in a suitcase," Wingo says.
In spite of his success, or because of it, Wingo is hardly relaxing. The free candy and drinks may make his company look laid back, but AuctionRover pushes staffers to make the bite as powerful as the bark.
Staff members are not ashamed to put up banners on interstate overpasses or dress up in dog costumes to get recognized.
At the end of the day, Wingo claims he does not worry about money. He is just interested in making Rover perform new and better tricks.
"You just have to think of, 'What did I do today to impact this business?' And then the stock price will follow," he says.