Cycling – the ‘in’ sport in Silicon Valley

Get on your bike if you want to meet leading investors or start-up bosses and start pedalling

Thinking he needed to take up a "California sport," Greg Gretsch started cycling in 1988, when he moved to the Bay Area to work in marketing at Apple after graduating from the University of Georgia. He bought a 10-speed road bike and joined a group of other Apple employees for a standing noon ride.

“I think I went four miles before I got dropped,” he said, a reference to being left behind by faster riders.

Today, Gretsch (49) is a founding partner with San Francisco-based Jackson Square Ventures, which makes early-stage investments in fledgling companies, including a social network and performance-tracking app for athletes call Strava.

He rides an average of five days a week on paved roads in the Bay Area and on trails near his second home near Lake Tahoe. Cycling is primarily for exercise and escape, he said, but it has also been good for his career. "Connecting with people is important to what I do, and you can learn a lot about a person, and from a person, on the bike," said Gretsch, who founded three companies before going into venture capital in 2000 at a firm called Sigma Partners.


For many years, cycling has been the sport of choice for workers in the region’s highly competitive tech community, the antidote to more leisurely pursuits like golf. But just like golf, it has become a way for investors and executives to socialise and strike deals.

Fast-track connections

Max Levchin (41), one of the founders of PayPal who has a well-known cycling obsession, recalls how some people have tried to pitch ideas to him during his daily training sessions, typically cruising at more than 30km/h. "I've been pitched companies on the bike, but I tend to ride fairly fast," said Levchin, who is an early-stage investor and chief executive of the San Francisco-based financial services company Affirm.

It was through cycling that he got to know one of his Affirm co-founders, Jeffrey Kaditz. "We did a training ride," Levchin said, "and he was one of the faster riders out there."

Sami Inkinen, a co-founder of the real estate website Trulia and an accomplished triathlete, made the case for his startup, Virta Health, while on a ride this year with Levchin and another investor and cycling enthusiast, Raymond Tonsing of Caffeinated Capital. That was exceptional, Levchin recalled. "It's rare that you have someone who can pitch a company while riding hard, and I'm not going to slow down."

Tonsing invested shortly after the ride, and Levchin joined in several months later.

‘My shrink’ Steve Anderson, founder of Baseline Ventures, which was the first investor in Instagram, has heard investment ideas while cycling, “but mostly in the context of, ‘can you help me work through my pitch, and if you are interested, let’s talk about it later,’” he said. As a boy he rode 15km a day delivering newspapers, and he started riding again regularly 20 years ago. “It’s my exercise, my shrink and my Zen rolled into one,” he said.

Gretsch got to know the computer billionaire Michael Dell through cycling after Dell acquired the Sigma portfolio company EqualLogic in 2008 for $1.4 billion. The two met in Hawaii after the deal was completed and went cycling. "Outside of college, the strongest relationships I have are with people I have worked with or worked out with," Gretsch said.

Venture capitalists, recruiters and other professional networkers have introduced cycling events throughout the Bay Area that focus on building camaraderie, not just lactic acid.

In May, Gretsch started inviting "Silicon Valley types" to join a monthly ride that typically meets near the Golden Gate Bridge and covers 30km to 50km around the Marin Headlands. This summer, Gretsch invited the group to a mountain bike ride near Lake Tahoe. The outing, which climbed to a gruelling 2,500m, included Andrew Buckley, who heads up cycling programmes at the Northstar California resort; Jake Knight, an entrepreneur whose family started Knight Transportation; and Anderson from Baseline Ventures.

Startup Ride

To find potential members of the group, called the JSV SF Startup Ride, Gretsch compares his company’s network of professional contacts with San Francisco Bay Area users on Strava, the app that lets users track and compare their times, distances and routes.

Some members of the group, which now has more than 40 members, are longtime acquaintances of his, but Gretsch said he had met new people on every ride and had "already seen one deal because of it". He is still a regular at some of the continuing group rides in Silicon Valley – there are several of them, each with its own personality and pace. The Noon Ride, for example, meets every weekday, follows the same route around Palo Alto, and has nearly 150 members on Strava. "There are sometimes three group rides on any given day, from moderate to 'kick you in the butt,'" said Jeff Selzer, general manager of Palo Alto Bicycles, which opened in 1930.

"What I like about cycling is a ride can be any length, and most people know how to ride a bike," said Ali Behnam, co-founder of Riviera Partners, a national recruiting company that counts Dropbox, LinkedIn, Pinterest and Uber among its clients. "Golf is a big-time commitment, and it requires practice to be reasonably good," he said. "There is nothing worse than stepping up to a tee and duffing it."

Cycling, by contrast, is communal and lends itself to the formation of common bonds, whether it’s because of the lung-burning sensations of a hard climb, the endorphin-inducing thrill of a big descent, the expense of the equipment or the form-fitting attire. “You can’t hide much,” said Behnam (49), who has been cycling for 17 years, “but usually there is food and drink involved.”

In the spring, he participated in the Bottega Gran Fondo, a cycling and culinary event in Napa Valley. He has organised several group rides with cycling celebrities, including the former professionals Gary Fisher and Bob Roll, who is best known for his Tour de France commentary.

With these rides, Behnam said, there is some unspoken etiquette. Fellow cyclists should not monopolise one person’s time, and, unless the group is exceptionally competitive, “You don’t want to just drop the person you’re riding with,” he said. “Don’t try to crush them.”

Likewise, participants should not claim to be “big” cyclists if they are in fact recreational riders – especially if they are trying to win the trust of prospective business contacts.

Before riding with anyone new, Levchin usually does a quick search on Strava to get a read on the person’s experience. “If I think it will be painfully slow,” he said, “I suggest we go for coffee.”

– New York Times News Service