"Since I was a kid, I've been interested in understanding the systems behind these seemingly random things in nature," Gilbert says. But this was the late nineties, when the tech bubble was being inflated with tornado-gauge force, and a couple of his buddies from Yale were starting a dot-com, which he joined as a consultant. The company, like so many others, went bust, but it was an important lesson for Gilbert in how e-commerce transactions worked. More crucially, he also picked up computer programming—by teaching it to himself after work each night. (Some people have happy hour; others find comfort in zeroes and ones. These days Gilbert can't even find the time or, evidently, the right speed, for a girlfriend: "In two weeks they're usually going 50 mph—marriage, kids—and I'm like, 'Hmm, I'm trying to figure out if we should see 3:10 to Yuma at 7:00 or 10:00.' ")
Read the story behind the founder of Proclivity Systems.