Joe De Sena learned the value of hard work cleaning the pools of Queens mobsters. And from Wall Street to the founding of his Spartan Race empire, he never stopped learning. now he wants to teach you.
Credit: Photographs by Peter Yang

In the course of a lifetime, it's pretty obvious you're going to encounter someone like De Sena just about never. So when you do, it's only natural to wonder, How did this happen? What were the circumstances? Why aren't I like this? What can I do to be more like this? Actually, this is something De Sena himself has thought a lot about. "I'm digging deep to find out what happened," he says, "because I want to redo that for my kids." He's almost feverish about wanting his kids to be as big-league, crackerjack, top-notch as he is. The three older ones all play instruments. The boys are wrestlers (and statewide contenders). His older daughter is well on her way to multiple pull-ups. They have a full-time Chinese housekeeper who is teaching them Mandarin, and are allowed to watch only Chinese-language television. And yet De Sena is aware that the things that shaped him most essentially will never have a hand in shaping them.

A 9-year-old De Sena in Howard Beach, Queens.

Back then, in the 1980s and early 1990s, everybody who was anybody in Howard Beach was a mobster. The guy Robert De Niro played in Martin Scorsese's GoodFellas lived there, as did John Gotti and any number of bosses, underbosses, captains, and capos. The soldier who gunned down Gambino don Paul Castellano outside Sparks Steak House in Manhattan — "That was my neighbor," says De Sena. "I mean, it was the organized-crime capital of the world. Every frigging house was organized crime." His mom, Jean, wanted no part of it. She was a meditating, yoga-practicing, health-food-eating, deodorant-despising half-hippie girl who never really fit in. His dad, Ralph, didn't want to get involved, either, but what could you do? "Let me put it this way," De Sena goes on, somewhat uncomfortably. "It was very hard to be in Queens and Brooklyn and be a legitimate business person, which he was, and run the kind of businesses he did — trucking, a warehouse, air freight — without having lots of friends."

Often, the dinner-table conversation revolved around who was going to jail and for how long. This worried De Sena. "I kept thinking, 'Could I do 20 years?' " he says. "Could I do the time and do whatever needs to be done to get through?" He decided he needed to get tougher, so he took cold showers, walked the streets carrying duffel bags full of rocks, two hours at a clip, and swam 30 laps after cleaning pools for 10 hours straight. He started doing this when he was 13. "I was a nutcase," he says. "All the neighbors were like, 'What the fuck is this kid doing?' But those things definitely made some DNA adjustments, and definitely had some influence on the races later on."

In the early 1980s, all his dad's businesses went bust: They were overextended, says De Sena, and "funding in our neighborhood came at a serious price, with serious consequences." Shortly thereafter, his parents divorced, he and his mom moved to Ithaca, New York, the alimony checks stopped coming, and the heat in their house was cut off in the middle of winter, leaving him to stew in a deep crucible of uncertainty, doubt, and fear. Not that he ever experienced it as such, because he was spending his summers back at his father's in Howard Beach, where he was already getting shit done with his pool-cleaning business.

"What happened was, my other neighbor was a big organized-crime figure in the Bonanno family," he says. "My dad lost everything. This guy was just being nice. He said, 'Hey, come clean my pool.' I cleaned his pool, so then he gave me the head of another organized-crime family's pool to clean, and then it was John Gotti's pool. I had 750 customers, most of whom were connected in one way or another. I cleaned pools for 80 percent of the organized-crime people you read about in newspapers. I come into the house, I have coffee or whatever, I got to know everybody that close. I did this for 11, 12 years. I watched how they ran their families. It was crazy. They'd lose their wife, their house, their car. I made a mental note not to run my house that way. What did they see in me? I was a very hard worker. If you're in the business that they are in, I'm the exact guy you would want to attach yourself to, because I'm an earner."

Meanwhile, back in Ithaca, he'd started an illegal fireworks business, selling Black Cats and bottle rockets to other junior high kids for their lunch money, which ended after he got nabbed in an administration-led sting operation ("They set me up!") and was suspended for two weeks. He then went into the T-shirt business. He was nothing if not entrepreneurial. After high school, he decided to go to Cornell, was rejected three times, did not take no for an answer, and got in on the fourth try. He returned to his Howard Beach pool business after graduation, made $200,000 a year, scored $100,000 overnight on a hot stock tip, and at the age of 24, sold his pool business for $500,000. Then he went to Wall Street, started a new job as a $30,000-a-year trainee at a brokerage house, worked his way up, saw a guy running in the stairwells, started running in the stairwells himself ("I used to live in stairwells. I mean, that's what I did"), ran marathons, flew places for triathlons, survived that car accident, entered more triathlons, and one day decided to start his own Wall Street trading firm. All he hears is, "You were a pool and construction guy. Nobody's gonna do business with you." They were right, until the day De Sena realized he had the wherewithal to get himself and his would-be clients a table at Rao's, an Italian restaurant in East Harlem, reservations impossible to come by, the hottest joint in town. "Fourteen tables," he says. "Very difficult to get into. Denzel Washington might be there, Billy Crystal, the mayor, wiseguys. Somebody once got shot there. Everybody wants to go to Rao's. Clients loved it. So how did I get in? It was handy having friends from Howard Beach." He kind of shifts sideways. "Man, in those early years, that table did a lot."