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Silicon Valley quest: Wind over water

June 16, 2008 |  7:11 am

Bill Tai is as competitive as venture capitalists come. But in spring and summer, even as the latest technology wave gusts through Silicon Valley, don’t look for him on Sand Hill Road. The Charles River Ventures partner is likely to be enjoying a wild ride on the San Francisco Bay as he pursues his quest for wind over water.

Kitesurfing VC Bill Tai catches airTai (in photos at right) launches from a mudflat, known as Third Avenue, that's east of U.S 101 near the San Mateo-Hayward Bridge. He picks up speed and power as he jumps waves, his colorful canopy pulled by strong winds. His kite once belonged to legendary big-wave surfer Laird Hamilton.

"Bill has been known as the mayor of Third Avenue for quite some time," colleague Saar Gur said.

Kiteboarding, also known as kitesurfing, is one of the fastest-growing water sports in the world. Standing on a board tethered to a kite that looks like a parachute, riders can go as fast as 55 mph. They often vault 30 feet in the air (some pros hit heights of 70 feet), feeling the kind of adrenaline surge that techies usually get from a successful product launch or initial public offering.

Aerial view of kiteboarding VC Bill TaiIt has become the extreme sport of choice in Silicon Valley. Aspiring entrepreneurs can skim atop the water alongside avid kitesurfers Larry Page and Sergey Brin, the thirty-somethings who founded Google Inc.

It’s not just that the unique geography of the Bay Area lends itself to kiteboarding. Tai, 45, says the sport appeals to Silicon Valley because its requirements tap the qualities of the inner geek: energy, passion, self-reliance, perseverance, fearlessness and calculated risk-taking. Divining the technical underpinnings of kiteboarding also stimulates a steady stream of brain teasers, as practitioners analyze such variables as wind speed and direction, tide movements, the capabilities of the equipment and the height and speed of waves.

Aerial view of kiteboarding VC Bill Tai At the same time, Tai and Gur say that when they're on the water, kiteboarding consumes all thoughts, offering them a rare reprieve from the 24/7 business cycle. It's basically a Silicon Valley version of meditation. And, unlike other water sports, kiteboarding is social and collaborative, reinforcing another key local ethos: Relying on your confreres to help you launch, land and steer clear of trouble.

Silicon Valley isn't much for corporate golf outings. Entrepreneurs, investors and engineers experiment with sports the way they experiment with new technologies.

"People going kitesurfing after work here is like the original astronauts roaring down the coastal highway in their Corvettes," said longtime Silicon Valley observer Paul Saffo, consulting associate professor at Stanford University. "It’s all about the speed and the adrenaline."

For Tai, a former windsurfer, kiteboarding is serious business. He does 1,200 sit-ups every morning to stay in shape: four sets of 300 while watching CNBC before the market opens, sprinting through e-mail between sets.

Tai jokes that he's a kiter who also happens to be a venture capitalist. He chronicles his kiting adventures on his blog, including the time a few years ago when he had to be rescued under the Golden Gate Bridge by the Coast Guard. His biggest rush: recently becoming a sponsored professional rider.

VC Bill Tai kiteboarding "I have more fun with that than anything I have ever done with work," Tai said.

Quite a statement from a guy who, in his 17-year venture career, has seen 16 of his portfolio companies go public.

Tai is perhaps most famous for his kiteboarding pilgrimage each May to Maui’s Kite Beach, the center of the kiteboarding universe.

He puts on the Mai Tai Kite Camp with Susi Mai, one of the sport's reigning queens. The event offers three to seven days of intense kiteboarding and professional networking in a sublime Hawaiian setting. Now In its fourth year, the camp also offers a rare opportunity ...

... to learn the ropes from top professional kiteboarders.

Bill Tai with kiteboarding gear"Bill always brings together a great group of people," said Ken Howery of Founders Fund. He first learned to kiteboard in 2003 and has attended Kite Camp twice. "Last year, one of the groups I met at the event even invested in our fund."

Philip Rosedale, founder of virtual world Second Life, was a first-timer at Kite Camp. "I finally got on the board, which was just really cool," he said.

Ben Ling, a former Google employee who now works at Facebook Inc., took lessons at Kite Camp and offered some advice to pro kiteboarders on building a product and a business. Now Ling is thinking about getting his own gear. He was joined in Maui by other Facebook converts.

"It’s like no other sport because of how much power the wind drives. It’s interesting to navigate that power and make sure you are directing it in the right way," Ling said. "It’s similar to working in a start-up in that you have tremendous raw talent that you have to harness in such a way to achieve great things."

Here's a YouTube video showing off Kite Camp, and Tai's smart take about the intersection of tech and kiting:

Kiteboarding and start-ups have very similar characteristics and therefore draw addicts from the same gene pool. Both require the operator to deal with a huge amount of uncertainty and variability in conditions. Both require intense focus while engaged. Both are such that any ‘mistake’ can be extremely costly -- at a minimum derailing the experience and erasing all the work that went into set up, and in kiting, creating potentially dangerous and occasionally fatal situations.

Both require a ton of passion to get through the hard part, just to enjoy fleeting adrenaline filled moments where everything comes together to create the sensation of FLYING across or above the water. At the beginning, both experiences are essentially 'life on the edge of destruction' -- very fun for a certain type of person. Plus the COMMITMENT. Once you launch, there is really no looking back. Commitment means commitment once the power of the kite is locked and loaded, and attached to your body.

Kiting is also a sport where, as in start-ups, the variability in outcome of small inputs into the system are huge. Huge 10 - 20 foot jumps or spectacular crashes with a 5 inch tug on a control bar. Exciting for sure, and as in a start up, there's no place to hide.

Entrepreneurs by definition deal in environments with huge uncertainty, and of course have to completely FOCUS to make anything work. Passion and commitment are 1000% requirements.

This sport is just MADE for the people that populate this valley.

-- Jessica Guynn

Photos of Bill Tai courtesy of Tai