Sami Inkinen, a co-founder of the real estate website Trulia and an accomplished triathlete, made the case for his start-up, Virta Health, while on a ride this year with Mr. Levchin and another investor and cycling enthusiast, Raymond Tonsing of Caffeinated Capital. That was exceptional, Mr. 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.”  Mr. Tonsing invested shortly after the ride, and Mr. Levchin joined in several months later.  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 10 miles 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.  Mr. 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,” Mr. 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, Mr. Gretsch started inviting “Silicon Valley types” to join a monthly ride that typically meets near the Golden Gate Bridge and covers 20 to 40 miles around the Marin Headlands. This summer Mr. Gretsch invited the group to a mountain bike ride near Lake Tahoe. The outing, which climbed to a grueling 8,000-foot elevation, included Andrew Buckley, who heads up cycling programs at the Northstar California resort; Jake Knight, an entrepreneur whose family started Knight Transportation; and Mr. Anderson from Baseline Ventures.  To find potential members of the group, called the JSV SF Startup Ride, Mr. 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 people, are longtime acquaintances of his, but Mr. 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 Mr. 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 organized 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, Mr. Behnam said, there is some unspoken etiquette. Fellow cyclists should not monopolize 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, Mr. 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.”
In the highly competitive and communal tech industry, cycling is taking the place of golf as both an individual obsession and a camaraderie builder.