I have now figured out why Silicon Valley is obsessed with kiteboarding, and it only took me four years. I was so incredibly scared of the sport when first introduced to it, that I didn’t truly embrace the experience of learning it. Go figure.
I remember my first time “body dragging,” which is the first step before you get on a board. It’s like body surfing, except you’re hanging on to a kite. I was excited about the adventure until I accidentally dragged across a bed of coral and ingested mounds of seaweed. Later, more “successful” attempts yanked me clear out of the water and dropped me fast into the ocean over and over again. I had the wind knocked out of me several times.
Thanks to the help of Wind Over Water Kiteboarding School owner Jeff Kafka, who also taught Google founders Larry Page and Sergey Brin, I have gotten up and riding on a board once. This was last Fall in San Mateo, California. I figured it would be like riding a bicycle and was hoping to show-off my new skills at this year’s annual MaiTai event in Maui, which is an exclusive gathering of 150 tech entrepreneurs, executives, and investors was started six years ago by Charles River Ventures Partner Bill Tai and professional kiteboarder Susi Mai. But to no avail.
Despite my lack of mastery, I was still determined to find out why the 150 entrepreneurs, executives, and investors who attended the event, were so obsessed with the sport. How did they persevere past the pain to get to the fun?
So at this year’s event, I asked my friend Gretta Kruesi, a tech blogger, show host, and a professional kiteboarder and instructor, to help get me riding. After my first attempt, having been dragged through the rocks, lost my bikini bottoms, and stranded in the middle of the ocean off the coast of Maui with my legs dangling as shark bait, I was ready to give-up when she said, “You can’t be a quitter and a kiter.”
There are a lot of parallels between extreme sports and being an entrepreneur, something I mentioned in my segment with BranchOut CEO Rick Marini, when he likened riding a super bike at 150 mph with founding a company.
The same thing goes for kiteboarding. Just like you can’t be a quitter and a kiter, you can’t be a quitter and an entrepreneur. No matter how many times you have the wind knocked out of you, you can’t let it keep you from reaching your goal. Both entrepreneurship and kiteboarding are risky propositions. It’s probably why you find so many taking up the sport in Silicon Valley. They love a challenge and thrive on the adrenaline it takes to succeed.
“Everyone has to go through the same learning curve,” explains Kruesi. “But once you make it through and survive, it’s worth it and the most fun you’ll ever have in your life.”
That’s why nearly 1,000 techies asked to attend this year’s MaiTai event in Maui. Only 150 were invited in order to keep the group exclusive and to make sure every techie had an opportunity to kite on the tiny Pro Beach near Kahalui, Maui. But big things are ahead for MaiTai as Jason Fass, former product manager at Apple and Jawbone, has taken the lead to help create more opportunities for adrenaline-loving techies.
Take a look at this video I shot at this year’s event. It was epic, with lots of big air, big sponsors, and big start-up launches. Fass also talks about what’s next for MaiTai, and Bill Tai talks about helping to get kiteboarding into the 2016 Olympics.