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.

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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.

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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.”

 

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At 38, with blue eyes and styled blond hair, Inkinen grew up on a farm in Finland, and started his career there as a physicist at a nuclear power plant. In 2003, Inkinen came to Silicon Valley to pursue an MBA at Stanford, where he was introduced to the sport of triathlon. By then, marathons had become almost a mainstream undertaking— something a dedicated morning jogger could pull off. “For people who were smart and driven but for the most part sit on their asses all day,” Inkinen tells me at a café in San Francisco. “Triathlons were starting to become the next physical accomplishment. They were something to aspire to.”

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Inkinen’s first was the Wildflower Triathlon, held each May near King City, CA, two hours south of Stanford’s campus. It’s one of the world’s largest triathlons, drawing almost 8,000 racers to a festive tent city populated by vendors, musicians, and athletes. Inkinen describes it as Woodstock with “less drugs and slightly less alcohol.” A crew of Stanford business school students races in the Wildflower every year, as do members of Facebook’s Tri Team—a group of engineers, marketers, product designers, researchers, and “operations gurus” at the social networking company who, according to the team’s official Facebook page, like to “swim, bike, run, hack. And that’s just before breakfast.”

Inkinen taught himself how to swim mainly through watching videos: In January of 2004, he typed “freestyle swimming techniques” into Google, found clips to study, and after just 30 days went from the dog paddle to being able to swim continuously for a half hour. He’s since won the Wildflower, both in his age group (2008, 2009) and as the overall amateur champion (2011). In 2009, he set the amateur course record at Ironman Arizona, and in 2011 he placed second in his age group at the Ironman World Championship in Hawaii. The following year, in Kalmar, Sweden, Inkinen completed his fastest Ironman yet, in a blistering eight hours, 24 minutes.

Meanwhile, Inkinen built Trulia, which he co-founded while at Stanford. The company now has more than 500 employees, and is on track to post more than $100 million in revenues for last year. Inkinen lives in Marin County, and trains 60–90 minutes every weekday morning before 8 o’clock, and one to four hours each day on weekends. For smart, driven, analytical technology entrepreneurs like Inkinen who, for the most part, sit on their asses all day, the back end of triathlon performance looks like an operating system in perpetual upgrade. “There are hundreds of different things you can tweak,” Inkinen says. “It’s appealing for a mind that’s always like, ‘How can I improve?’”

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A self-described “data geek,” Inkinen tucks a sensor under his sheets to track his sleep quality, and wears a continuous glucose monitor under the skin of his belly when he’s training. He dutifully records every workout on a spreadsheet, noting also his fatigue level, weight, resting heart rate, caffeine use, caloric intake, and morning mood. This “training and life log” reads like Inkinen’s personal software code; if any bugs arise—a cold, or grumpiness—he can look back and make adjustments. “I can usually find a lot of explanations,” he tells me. It’s a fitness regimen that not only mirrors his approach to business but also plays a role in Trulia’s daily operations. “We have company ‘mind and body’ days with bike-riding groups,” he says. “And networking within sports circles helps in recruiting people to join our team, which we’ve done multiple times. You build relationships that are much deeper.”

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Silicon Valley cultivates its own breed of hyperfit techie—a product of the area’s outdoor life as well as of an industry built on intense personal drive and an obsession with quantifiable progress. Not to mention the area’s extraordinary wealth: San Francisco has the most ultrahigh-net-worth individuals (assets worth at least $30 million) per capita in America, according to the research institute Wealth-X. A recent survey showed that wealthy Californians also skew younger than the national average. In addition to expensive kiteboarding equipment, these young, active entrepreneurs can afford to buy $8,000 carbon-fiber bikes from the boutique bike stores that have cropped up around San Francisco, which they take to races like the Leadville Trail 100 MTB, a high-altitude mountain-bike competition in the Colorado Rockies, and La Ruta de Los Conquistadores, a coast-to-coast stage race across Costa Rica. They can afford to seek out the same kind of lactate and gas-exchange tests that were previously only available to Olympic or professional athletes. “When you have these type A recreational athletes, even if they suck in terms of performance, they’re interested in these kinds of things,” Inkinen tells me. “They can’t just go and do it. They have to have some kind of progress and development.”

VeloSF symbolizes the type of performance training that tech money can buy. The indoor cycling studio, located in San Francisco’s North Beach area, contains a bicycle valet, a bike-repair shop, physiological lactate testing, an open TRX workout space, and a state-of-the-art sound system. Technology executives like Mark Pincus, the co-founder of online gaming giant Zynga; Mike Moritz, chairman of Sequoia Capital; and PayPal co-founder Max Levchin all train at VeloSF with Matt Dixon, owner of Purplepatch Fitness, who leads a kind of high-tech spinning class. “If you think about the tech industry, it attracts people who are ambitious and goal-driven, who like measurable results, but also like adventure,” says

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Dixon, a physiologist, former professional triathlete, and elite coach who’s trained multiple Ironman champions over the course of his career. “Cycling has all of that. And you can have toys. It really is by far the No.1 sport in the tech industry.” Dixon also leads his executive clients on weekend rides around the Bay Area, as well as weeklong cycling trips to Europe that combine Tour de France-type hill climbs with wine tastings. “Sometimes you look around and think, Valleywag [a Gawker Media news and gossip blog] should be here, because this is the Who’s Who of Silicon Valley now,” he says. “Cycling has become the new golf. Deals used to be done on the course. Now they’re done on two wheels riding Old La Honda Road.”

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Talking with Bay Area Internet entrepreneurs, many of whom are under 45, it would seem that fitness is just a backdrop for an informal kind of networking that, in more traditional industries, might take place at a country club. “It’s an explosion,” says Biz Stone, the Twitter co-founder who currently owns an app maker called Jelly Industries. “My employees are all big cyclists, ultramarathoners, weightlifters.” There’s an outdoor fitness boot camp (and “networking community”), started by Edward Sullivan in San Francisco, called freefit.org, where several entrepreneurs gather for high-intensity interval training, body-weight exercises, and plyometrics—and that’s just before breakfast. A select group of clean energy executives retreats to a ski condo in Tahoe. Rob Bailey, the CEO of DataSift, a big-data startup, tells me that “many early- to late-stage VCs” work out at the Sports Club/LA in downtown San Francisco. “Mike Stoppelman [the CTO of Yelp] works out there,” Bailey says, as though he were talking about a celebrity. “Usually we’re so transactional and slammed. At the gym, you’re relaxed and have a chance to build relationships with the people you do deals with.”

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Every morning before dawn, a group of employees for large tech companies on the peninsula congregates outside a coffee shop in San Francisco for a two-wheel commute to Silicon Valley. SF2G (San Francisco to Google) began in 2005 as an activity listserv inside Google; employees who lived in the city used it to find ride partners. It’s now an open Google Group that comprises around 2,000 employees from companies like Apple, Facebook, and Bosch. “It’s really an MVP list of people and companies,” Brian Kemler, a Google program manager in privacy and self-driving cars, tells me.

Any member of SF2G can initiate a trip by proposing a mustering point in San Francisco—usually Philz Coffee or Ritual Coffee in the Mission District—and declaring an intensity level for the ride, on a scale ranging from 0 (“unsustainable pace, 100% effort, most people dropped”) to 4 (“no rider left behind, easygoing, genteel, plenty of regroups”). Posters are encouraged to add other designations to their plan, such as “business pace,” described as a “no-nonsense, very consistent, moderate-to-fast pace, pacelines, no sprints, wear your business socks” kind of ride, or “shenanigans/ tomfoolery,” a commute in which “attacks, sprints, arbitrary contests of all kinds” are encouraged.

Usually, two groups of eight to 12 cyclists depart each morning and head south along one of two routes charted by SF2G’s pioneers. The mostly flat Bayway (42 miles to Mountain View) follows frontage roads and suburban streets, while a hillier route via Skyline Blvd. (45 miles) has a 2,400-foot elevation gain but offers the reward of scenic ocean views. Farther down the peninsula, riders peel off toward their respective employers: Facebook in Menlo Park, Google in Mountain View, Apple in Cupertino. They shower in the company showers, eat breakfast at the company cafeteria, and in the afternoon stow their bikes on the company shuttle for the trip home.

“A lot of these people have become my closest friends,” says Kemler. “But it’s really benefited my career as well.” When Kemler applied for a job within Google last year, he turned to a fellow cyclist for advice. “I have a group of people in my immediate team that I can reach out to for mentoring,” he says, “but if something comes up, I’ve got other connections at other companies.”

Every fall, Sequoia Capital hosts an annual bike ride for an exclusive group of industry players. Sequoia has backed some of the most successful tech companies, including Google, Yahoo, and Apple. By Sequoia’s own estimation, around 20% of the Nasdaq’s value is made up of companies it’s funded. Its annual event is like the Valley version of a golf invitational. This year, participants included Riley Newman, head of analytics at Airbnb, and Othman Laraki, an entrepreneur and former Twitter VP. (Inkinen and Moritz also attended.) On the longest of two rides, the riders logged 70 miles and climbed more than 6,000 feet. They schmoozed afterward over pizza and continued the banter on Strava, a social-media app for running and cycling where the participants, naturally, posted performance analytics of the ride.

“Cycling really embodies the Silicon Valley culture,” says Joe Dobrenski, a Sequoia Capital partner, about an industry that places greater value on what someone succeeds in building than, say, where they went to school or their family ties. “It’s a meritocracy,” he tells me. “Everybody’s kind of equal on a bike.”

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