In 2011, Tom Hessert went to his first horse race. It was the 2011 Preakness, and, he said, “after trying to figure out the tote machine for half an hour,” he decided to place a wager, $5 to win on a horse whose odds were 5-1. After cashing his winning ticket for $30, he was, as he put it, “instantly obsessed.”
“I had a total blast,” he said recently from his office in New York’s Flatiron district. Like many first-time bettors, Hessert didn’t make his selection after handicapping the race. He bet the horse because he liked its 5-1 odds and figured that if he won, he’d make enough to buy a couple of drinks. 
He was with his brothers Walter and Bill. While Bill had been, according to Tom, “involved in the racing industry for a while,” Walter was a newcomer, too, attending only his second horse race, but what began as a day at the races quickly became a business plan for DerbyJackpot, the brothers’ online racing game that masquerades as an advance-deposit wagering account. Or maybe it’s the other way around.
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