Draper might also perform his own version of the frat rock classic Wild Thing ("Wild thing, I think I’ll fund you, but I wanna know for sure . . ."). And these days, he reminds acquaintances to catch him, along with his daughter, his nephews and his brother-in-law, on the movie and spin-off Nickelodeon TV series The Naked Brothers Band. The show is very much a family affair, created, produced, written and directed by his sister, Polly Draper, perhaps best-known as an actress in the 1980s television series thirtysomething. The Naked Brothers Band is a sweet-natured comedy about kid and tween angst among the members of a very youthful rock band. Draper, the seasoned Silicon Valley venture capitalist, appears occasionally, playing the school principal, Joe Schmoke.

Draper is, by all critical accounts, out-of-tune as a singer and somewhat stiff as an actor. "We both got kicked out of music class for singing too loud and too poorly," says Tony Perkins, Draper’s friend since first grade, who grew up to be the creator and editor of Red Herring magazine and, more recently, founder of the social network AlwaysOn. Draper’s venture capital career, on the other hand, has produced some notable hits: Hotmail, the Internet telephone service Skype and the huge Chinese search engine Baidu—along with the dozens of misses that litter any venture capitalist’s portfolio.

When Draper’s name pops up in the business media and in private Silicon Valley circles, cynics often talk about how he failed to see the potential of Google (he met cofounder Sergey Brin on a plane, but decided to pass because he was already backing some 20 other search engine companies, most with names no one would remember) and how he’s hardly the first investor in either Skype (his father was the first) or Baidu, though he placed lucky bets on both.

"Sure, people say I’m crazy like a fox," says Draper, who stands a gangly 6-feet-4 and seems to shrug off self-doubt and criticism like he does an entrepreneur with a bad elevator pitch. For the near future, he’s staked his reputation on a number of ventures in very hot, but unproven, technology. "I’m pretty excited about the two electric car companies we funded," he says. "One is called Tesla. It has sports cars that can go from zero to 60 in less than four seconds. The other one is called Reva, and it’s a lower-cost electric vehicle made in India."

Like Father, Like Son
But it isn’t always easy to be Silicon Valley royalty. In a place where anyone who wanders into town with a great technological breakthrough can become a celebrity overnight—or at least make it look that way—Draper had to contend with proving he had his own worthy ideas and wasn’t just riding the reputation of his father, Bill Draper. The elder Draper is a partner in the VC firm Draper Richards and was the son of a venture capital pioneer, William Henry Draper Jr., who founded Draper, Gaither and Anderson in Silicon Valley in 1959 following a distinguished career as a four-star general, undersecretary of the Army and co-architect of the Marshall Plan. In the 1960s, the retired general cofounded the Population Crisis Committee and advised China on its one-child-per-family population control program.

Bill was one of the first venture capitalists to deploy the limited-partner structure that enables VCs to take a position in a startup company with a plan to exit in three to five years through some sort of buyout by other investors. "Before that, you had to wait about seven years to see if you had a winner," Perkins says. "It was mostly the Whitneys and Rockefellers who invested this way; there just wasn’t an industry of full-time professional venture capitalists." Bill also served as chairman of the Export-Import Bank under President Reagan and CEO of the United Nations Development Program, a position that required the family to travel frequently.