It’s an open secret in the technology industry: If you want to score a deal, learn to kiteboard. Alex Mouldovan, a 42-year-old entrepreneur, took up the sport last summer. He was driving along Third Avenue in San Mateo, CA , one May afternoon, and the colorful fluttering of kites offshore lured him to the beach. Mouldovan was the founder of the social-marketing software company Crowd Factory, which he’d recently sold to a San Mateo-based firm, Marketo, for more than $13 million. When he wandered over the dunes that afternoon, he’d just rung the Nasdaq bell in New York City, via satellite, to mark Marketo’s initial public offering. He was instantly inspired to buy some kiting gear and take lessons. That’s how he met Bill Tai, a partner with Charles River Ventures.
Kiteboarding, with its athletic demands and inherent dangers, naturally captures the curiosity of risk takers and adrenaline junkies. The sport is a cross between windsurfing and paragliding. With feet hooked into a wakeboard, “kiters” harness into a giant kite and skim across the surface of the water at speeds of up to 65 miles per hour. They launch off waves and twist acrobatically in midair. They must scrutinize variables like wind direction and tidal flow. Miscalculations can mean falling out of the sky onto shoreline rocks or outcroppings.
Google founders Larry Page and Sergey Brin, who are avid kiteboarders, both learned at Third Avenue. “There’s a little bit of punishment that you choose to accept when you either launch a startup or decide to pick up this sport,” says Tai, who’s been hospitalized three times for kiteboarding-related injuries. “You’re going to get tossed around and slammed and dragged underwater for periods of time, and you have to suffer through it and stay committed until you succeed. Once you step in, just the process of trying identifies you to people in the community as a type similar to themselves.”
Tai, an angel investor to numerous startups in Silicon Valley, invited Mouldovan to MaiTai, a series of kiteboarding events for tech execs, startup founders, and venture capitalists that he started seven years ago with professional kiteboarder Susi Mai. “The same minds that want to apply technology to solve all kinds of technical and life problems are attracted to this sport,” says Tai. “It’s a highly multivariate equation that some people just want to solve.” MaiTai began as a small gathering of friends at the vacation home of Ken Goldman, the chief financial officer of Yahoo, and is now a five-day, invite-only event held at various times of the year in the Hamptons; Maui; Cape Hatteras, NC; the Dominican Republic; Perth, Australia; and Necker Island, Sir Richard Branson’s private Caribbean island.
Forbes estimated the total net worth of individuals on a recent MaiTai trip in Hawaii at $7 billion in market value. Through joining MaiTai a few months ago, Mouldovan has discovered companies in which he wants to invest and has been hired by other MaiTai-connected companies as an adviser. Its kite gatherings epitomize the casual comingling of sport and business. The program includes sessions in which aspiring entrepreneurs can pitch potential investors and solicit feedback (including, at Necker, from Branson himself ). At one recent MaiTai event, a 25-year-old Australian entrepreneur and amateur kiter, Melanie Perkins, presented her idea for a cloud-supported and collaborative graphic design platform. The former CEO of Shutterfly and the inventor of Google Maps were among those sitting in the room who loved it. Within months, with help from the MaiTai network, Perkins’ startup, Canva, acquired $3 million.
Companies are also hatched at MaiTai weekends. In May 2011, while snapping photos of pro kiteboarders in Maui, 32-year-old entrepreneur Matt Brezina wondered why he couldn’t send postcards from his iPhone. Seven months later, Postagram, the company he went on to launch after the trip, had 30,000 users. And in previous years, Voxer and Tango, two of the many startups that launched their products at MaiTai, were listed among the year’s top-30 most downloaded Apple apps. “Things like that happen on our trip,” says Tai. “It’s really unbelievable.”
Many of Silicon Valley’s most successful Internet companies came of age only in the past decade, when the idea that fit employees also make happier, more productive ones became a truism. Free gym memberships and yoga classes are standard HR perks; Twitter and LinkedIn, for instance, recently built CrossFit gyms inside their headquarters. Google has a bike repair shop at its Mountain View campus (as well as rock-climbing walls and swim-in-place pools). “Body hacking” is now a thing. The dressed-down office culture inside most tech companies means every day can be casual Friday. Jessica Shambora, a marketing communications manager at Facebook who’s raced in five half-Ironmans, said she will occasionally wear exercise attire to work so she can squeeze in a session later.
“Maybe it’s because it’s a younger generation, but it appears to me that being totally unfit is starting to be a little bit socially unacceptable,” says Sami Inkinen, co-founder of the real estate website Trulia. “It’s something people are aware of: If I’m successful in business, why should I be so unfit that it’s actually unhealthy? It seems that opinion is changing.”