CEOs Who Ride the Wind

Greek mythology’s Icarus, using wax wings, crashed because he flew too close to the sun. But a fair number of today’s CEOs harness the wind to skim across snow, ocean, surf, sand or paved surfaces at 40-plus miles per hour, even uphill.

The Paragliders

Barry Barr, CEO of KAVU True Outerware, got hooked on free flight when his father, a pioneer during the infancy of hanggliding, duct-taped him to his chest and they ski-launched down a mountain in Sun Valley. Now a paraglider, he has been flying in the Americas, Europe and the Pacific over the last 23 years.

Barr tries to paraglide everywhere he goes and he encourages the company’s staff to drop everything and get outside when the weather is good. In fact, there’s even a contest for the KAVU employee who sleeps outside most often during the year—the prize is a pair of ski passes.

Dirk Van Rees, president of Courtroom Visuals, has been paragliding for 10 years and flies all over the world. He also flies tandem, taking along family and friends for fun, or flying with tourists over Aspen and Snowmass for a paragliding tourism service.

Jeff Hamann, president of Hamann Companies, flies a powered paraglider, which includes a motor backpack unit to give thrust to a climb. In the last eight years, he covered almost the entire distance between Arizona and Panama, and he expects to fly the remaining parts by year’s end. On a recent group trip, he flew over the nearly impenetrable rain forest of Panama’s Darien Province, home to crocodiles and FARC guerillas.

The Windsurfer

“When it’s windy and I’m in the office, my staff wonders why I’m there and not out sailing,” says David Troup, CEO of Solinus. A windsurfer for the last 30 years, he sometimes hits 44-plus miles per hour and somersaults up to 40 feet over waves.

Troup hauls his gear on business trips and surfs between meetings. An extreme sports omnivore, he also does stand-up surfing, giant slaloming, snowboarding, kiteboarding, skiing, rock climbing, mountain biking, sailboating and flying. When he was 15, he raced in the Windsurfer World Championships. You can see him in various snowboard pants and gear in many of the photos which he has posted online showcasing to the CEOs of the world, that work is not everything. One should also know how to blow off steam and have a hobby.

The Skydivers

The challenge of jumping out of a plane 13,000 feet in the sky and plummeting to earth at 160 miles per hour has helped Dave Afre of Apollo Innovations “sweat the small stuff and overcome those self-limiting beliefs we hold, sometimes.”

Entrepreneur Peter Shankman has skydived over 220 times, all over the world, “whenever I’m in a city with a drop zone. Sadly, it’s never enough.” He’s also completed 13 marathons and seven Olympic distance triathlons.

As Brandon Radcliff, president of Specialty Watercraft, makes his safety check before a jump, he says to himself, “No. 1. Gravity is non-negotiable; No. 2. For everything else, see No. 1.”

The “New Golf” of Silicon Valley

Sergey Brin has kiteboarded along a 40-mile path in San Francisco Bay and built a sailboat that can be kite-powered. Larry Page kiteboard-raced against Sir Richard Branson between two British Virgin Islands. The Google founders’ passion for kiteboarding has encouraged a wave of Silicon Valley entrepreneurs to begin kiteboarding, one of the newest of the extreme sports.

Bill Tai, a partner in Charles River Ventures, who converted to kiteboarding from windsurfing 10 years ago, is another Pied Piper for the sport. He has drawn hundreds of Silicon Valley entrepreneurs into kiteboarding. They include: Trip Adler, Jared Friedman and Tikhon Bernstam, co-founders of Scribd; Josh Williams, CEO of Gowalla; Johann Schleier-Smith, co-founder of Tagged; Ed Baker, CEO of Friend.ly, Tim Hickman, CEO of Hard Candy Cases, Susan Coelius Keplinger, COO of Triggit; and Scott Painter, CEO of TrueCar.

Among its enthusiasts, kiteboarding has become known as the new golf of Silicon Valley.

The list keeps growing. Tai’s annual kiteboarding and tech networking camp drew more than 150 founders and executives of high-tech, startup companies in 2010, compared with 80 in 2009. He also created a snow-kiting camp that was attended by three dozen participants this year.

Among its enthusiasts, kiteboarding has become known as the new golf of Silicon Valley. Scott Painter of TrueCar, who has attended the kiteboarding camp for the last four years, says he was kiting before it became a sport. Nearly 20 years ago, he was “an odd sight, sand-surfing down the beach in Santa Monica in my Army boots.”

Elsewhere, Brian Beveridge of Greenridge Business Systems, kite-skis on frozen lakes in Canada in temperatures hitting -40 degrees, including wind chill. He ranked second in a 2010 Worldwide Speed Kiting contest, reaching a speed of 55.3 knots. Other active kiteboarding executives include Dave Morin, CEO of Path; Ken Howery, managing partner of Founders Fund; Konstantin Othmer, CEO of SpeedPad.com; and Jim Pitkow, CEO of Attributor. Sir Richard Branson tried to kiteboard across the English Channel for his 60th birthday, but didn’t make it because of bad weather.

Kiteboarding is not for the faint of heart. Once Tai was kitesurfing under the Golden Gate Bridge and broke his kite. Tangled in his lines, he was swept out into the Pacific Ocean and had to be rescued by the Coast Guard. “I thought I was toast,” Tai says. Undeterred, he was back on his board a few days later.