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Q&A: Angel Investor and Kiteboarding Guru Bill Tai

The tech power player discusses his love affair with extreme sports.

As co-founder of Mai Tai, a kiteboarding retreat and community whose members have an accumulated net worth of $7 billion, according to Forbes, Charles River Ventures' partner Bill Tai is one of Silicon Valley's most ardent kiteboarders. He's also one of the most connected, investing in startups such as Tweetdeck, Tango, and Voxer, and serving on the board of companies like Scribd and Glyde. Tai recently talked with Men's Fitness about his obsession with an intense and dangerous sport that combines the power of paragliding with the action of surfing. 

How did you get into kiteboarding?

For me, kiteboarding was an evolution from other water sports. I learned to sail an interclub dinghy while I was at Harvard but I wanted more speed and transitioned very quickly to windsurfing. I loved windsurfing because it puts you in touch with the water in a way boats can't, and they're light enough to catch air and even do flips with if you launch off a wave just right. I pushed myself pretty hard in that sport, and on a trip to Mexico with Aaron Gershenberg of Silicon Valley Bank in 2000, a couple friends of mine who were professional windsurfers brought some of the very first production kites and boards with them to try out. When I saw what they could do with that gear, I was in awe and knew that I had to try it. That Christmas I was given a "hand me down" of a kite that had belonged to [surf legend] Laird Hamilton but was too small for him and I taught myself to fly it that spring on a field in California.

You mentioned to Men's Fitness that kiteboarding "is a highly multivariate equation that some people just want to solve." What exactly does that mean?

Redirecting wind power to skim across the water in a precise direction—while not overwhelmingly hard—takes some practice. A rider has to be constantly adjusting the kite in three dimensions to remain directional- all the while navigating constantly changing waves, water surfaces, wind speeds and currents. It's a little like sailing in 3D but on a boat that sinks if you stop moving, while holding a throttle of a jet engine in your hands. The power is hard to describe—a rider is holding enough force in his hands to shoot himself 20-40 feet into the air in a tenth of a second—probably comparable to getting shot out of a cannon. That power is available to you most of the time.

What are some of the dangers of kiteboarding? Have you ever been in a pretty serious situation?

Accidents can happen in any sport where you are harnessing that much power. That said, the sport has gotten very safe over the past five years due to improvements in gear design to allow riders to automatically de-power just by letting go of the controls. Lessons have also been standardized and start off with "safety first." In the earlier years of the sport the gear did not de-power and even if you were knocked unconscious the kite would keep dragging you across land or water. In those years I did end up in the Maui Memorial Emergency Room a couple times. There are other situations that can also occur if your gear fails and you're to far from shore to swim back. I've also had my kite break while I was under the Golden Gate Bridge and I got sucked nearly a mile out to sea in 10 minutes. I was very lucky to have the coast guard come and pull me out of the water.

You got sucked straight out into the waves?

Straight out to the ocean. The water level in SF Bay rises and falls 6-10 feet a couple times per day, and the bay is very, very large. That volume of water goes in and out of the Golden Gate so the water current there can be very strong. At peak tidal flow, anything floating in the water without power will be moving a mile every 10-12 minutes. On that particular day it was peak flow with the water moving out—so I was basically heading outbound in the westerly direction pointing toward the Farallon Islands.

Did you have a plan?

Nope.

You were just like, this is it?

Well, yes, I was very lucky that another kiter named John Gomes saw me drifting out to sea and called the Coast Guard. He understood the situation instantly and also had a VHF radio with him. He called the Coast Guard, who saved my ass.

Do you have and tips for our readers? The dos an don'ts of kiteboarding?

Definitely take lessons from somebody that is qualified, certified, and knows what they're doing. If you're holding that much power in your hands you want to know how to handle it properly. When I launched my first kite, I did it myself and ended up accidentally flying myself over a field. I was literally skiing across the field barefoot until I came to a sidewalk, and when I tried to step over it the motion of pulling on the bar to step over the sidewalk loaded the kite with more power, so I ended up flying like Superman over the field at body height. It took me a bit to detach from the kite because I was Velcroed on to the control bar and when I finally released I hit the ground and skinned my palms and part of my chest.

But you stuck to kiteboarding?

Yeah, a friend of mine named Bernd Girod who was there ran over to me to see if I was OK. He tells me the first thing I said was "Wow!…did you see that? If I could harness that power it'd be amazing. How cool would that be?"

How fast do kiteboards go?

There was a new kiteboarding speed record set recently on water, 65 miles per hour. Kites can pull you really fast, but the part that is most amazing is the acceleration. A motorcycle or dragster can't take you from a standstill to forty feet in the air in a tenth of a second.

What brands would your recommend gear-wise?

My favorite kites are made by Cabrinha and Naish. If you're looking for a board, and are looking for a twin tip (something that resembles a wakeboard with fins) I love the Axon kiteboards. For surfboards, I really like Hydroflex.

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