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CEOs Gone Wild

Some of the country’s top execs are swapping their suits for spandex to compete in the most challenging races on earth

Imagine running through the wilderness for days, diving (on purpose) under solid blocks of ice or rowing a tiny boat across the Atlantic Ocean—then suiting up and heading into the office for a day of delegating. It sounds like the trajectory of a Bond movie, but this sort of double life—extraordinary feats of athleticism on one hand, your everyday nine-to-five on the other—is becoming more and more popular among a certain set of business titans.  

It usually starts out harmlessly enough. Forty-seven-year-old Nashville business mogul Phil Theodore says it occurred to him to do an Ironman when considering what he wanted to accomplish before his looming 40th birthday—beyond owning a variety of companies in the healthcare, print-management and consulting-services industries, that is. Despite his wife’s practical protests, pointing out a number of obstacles he’d face—Where would he find the time? He didn’t even own a bike! And so on—Theodore was determined. Five months later, he was in Brazil at a starting line. It was there that he met tech entrepreneur Daley Ervin, who has since become Theodore’s racing partner-in-crime.

“Then it kind of escalated,” says Theodore, in what could be called the understatement of the century. The two went on to run hundreds of miles at a time, at extreme altitudes and through myriad terrain, eventually taking on the aptly named Death Race, a biannual elimination-format competition in which athletes complete immensely difficult mental and physical challenges over the course of many days, from scaling mountains while wearing backpacks filled with rocks to chopping wood for hours on end. Only 15 percent make it through. “You don’t get to sleep,” says Theodore, somewhat boastfully. This coming December, he and Ervin will row a boat 3,000 nautical miles across the Atlantic Ocean from San Sebastián de la Gomera to Antigua to raise money for Team Beyond, a charity they created along with Manhattan philanthropy consultant (and fellow extreme racer) Jeff Smith to help use their races to benefit causes like hunger, clean water and cancer. Team Beyond is anticipating raising $5 million this year alone. 

Theodore and Ervin

Theodore and Ervin

Buttoned-up workaholics worth millions of dollars might not seem the most natural thrill seekers, but in a world that’s ever work harder, play harder, the combination is an ideal marriage. “As people take on more challenges at work, they also seek greater challenge in their personal lives,” says Dr. William Weiner, a New York City sports psychologist, noting that the interest among hard-charging business types in extreme sports—or extreme anything—has been growing steadily over the last decade. And although it may also seem counterintuitive for those who already experience extreme levels of stress at work to willingly seek out extreme pressures in their personal lives, Weiner also says the athletic ventures may have a positive impact on office performance. “In a certain way,” he says, “those challenges, particularly athletic challenges, sometimes embolden [executives] to take more risks in the workplace, too.” Many who’ve reached the top of their game professionally no longer face the same sort of hurdles that they did when they were younger and just coming up. And they miss it.

The extreme work/extreme play connection is clear to venture capitalist Philip Sanderson of IDG Ventures, an ultramarathoner who created a TED Talk titled “How I Hacked an Ultramarathon by Thinking like an Entrepreneur,” which encourages the idea of committing strongly to each and every goal—no excuses allowed. It’s a philosophy Sanderson says he has used in business from the start of his career, and which he has since extended to his athletic endeavors. “If I get home from work or out of a work dinner and it’s late—nine or ten o’clock at night—and raining, I’ll go out and run because I have to hit my 70 miles a week,” he says. “If I don’t run today, I have to hit 20 miles the next day, and I don’t have time to run 20 miles the next day, so it’s not even an option.”

Skulls given as medals to Death Race winners

Skulls given as medals to Death Race winners

There’s also, of course, the undeniable appeal of winning. These guys aren’t Olympic athletes, but they know how good it can feel to best the competition, especially if the competition happens to be someone in their circle of business acquaintances. With races like these, says Weiner, the animalistic desire certain CEO types have to constantly outdo themselves, and each other, is fulfilled. Chris Solarz, a managing director at New York City consulting firm Cliffwater, holds five Guinness World Records, including one for climbing stairs (going up 33,000 feet in less than 12 hours) and another for treadmill running (achieving the greatest distance in 12 hours by logging 77.07 miles). “I truly have not found my limit,” says Solarz. “I think my limit is when I’m curled up on the side of the road and I say, ‘I cannot take one more step,’ and have to be dragged off in an ambulance.” 

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