In 1996, Chris Hehman built one of the first online bracket managers for the NCAA men’s college basketball tournament, or March Madness, as it’s known to the millions of Americans who gamble on it every year. Hehman’s boss at the now defunct telecom company Nortel Networks wanted a better way to keep track of the 50-odd entries in the annual office pool. “Fifty doesn’t seem like a large number now,” says Hehman, “but back then you had to print it all and mark up all of the results and score them by hand.” Hehman’s program was such an office hit that he turned it into a business, PickHoops, which now processes 180,000 brackets annually.
PickHoops isn’t the only, or even the biggest, online bracket manager. Its volume is nowhere near the 5.9 million brackets filled out on ESPN’s free service or the 4.5 million at CBS Sports. All of them provide a place for the members of a pool to enter their picks, and the programs keep score as teams are eliminated from the tourney. PickHoops goes further: It allows pool members to look ahead at potential outcomes and will even generate their initial picks, taking into account their tolerance for upsets. About the only thing PickHoops won’t do is collect and distribute money. It’s not that Hehman couldn’t add this function. It’s that he’s afraid to. “When we were first getting started, we looked at what the various rules were,” he says. “They are often extremely confusing or extremely weird. It’s not practical for us to even know where and when it’s legal.”