Trending: Instacart valuation hits $7.6B after $600M round; Amazon removes Instacart branding at Whole Foods

Vinod Khosla at Startup Weekend EDU (Photos via Bootstrapper Studios)

Don’t call Vinod Khosla a venture capitalist. After all, the venerable Silicon Valley investor, entrepreneur and philanthropist doesn’t really have the best opinion of those who invest other people’s money in startups.

“I refuse to call myself a venture capitalist, and it pisses off most venture capitalists,” said Khosla, speaking at the kick-off event for Startup Weekend EDU in Seattle Friday night. “I am not in the venture capital business, because to me that means golf and parties and VC networking and VC golf trips and sailing trips. I don’t do any of those.”

Interviewed by TechCrunch founder Michael Arrington — who disclosed that Khosla is an investor in the newly-formed CrunchFund — the self-described “venture assistant” noted that he probably spends less time hanging out with other VCs than anybody on Silicon Valley’s famed Sand Hill Road. After all, the investor in AdReady, Square and Xobni said that he’d much prefer to hear a good entrepreneurial pitch.

“Most people who do well might go spend $100 million buying a yacht. And I’ve known plenty of people who have done that,” explained Khosla. “My yacht is 100 little $1 million startups…. That sounded a lot more fun, backing 100 young entrepreneurs than buying a yacht and sailing it once a week…. These startups are my yacht.”

To laughs from the crowd, Arrington then asked Khosla about his private plane. But the co-founder of Sun Microsystems said the plane is more of a utility vehicle, allowing him to efficiently travel to find the best startups.

Michael Arrington and Vinod Khosla at Startup Weekend EDU

It was an inspirational and thought-provoking discussion, and there were too many pearls of wisdom to count. But I especially enjoyed Khosla’s insights about the entrepreneurial spirit, and the fire and passion one needs to build something that has a big impact.

According to Khosla, that fire burns best among young entrepreneurs. And the reason for that is because they have not been conditioned to the traditional ways of doing things.

“After you work long enough, you get too know everything the way things are supposed to be, and you forget that new things can be invented,” he said. “The biggest danger in doing things is listening to experts…. You first have to reject all conventional wisdom…. And most people over the age of 30 … start to assume that they know how things work.”

In his view, young entrepreneurs are not as prone to following conventional wisdom and are more willing to try new things.

“Unless you try new things, you won’t do new things,” he said.

Khosla then launched into a lengthy and fascinating discussion of his views on failure, including a discussion of Steve Jobs and his own lessons from the blow up of pen computing startup Go.

“My philosophy in life is I don’t mind failing in trying new things. But it better be relevant if we succeed. I don’t mind the low probability of success, but I better be impactful if we do succeed. And that is sort of my key criteria now on what I spend my time on. Failure doesn’t matter, and I often say that my willingness to fail is what gives me the ability to succeed…. You don’t want failure, but you shouldn’t be afraid of it. Because, if you are afraid of it, what you do is avoid all of the risks … to the point where the consequences of success are inconsequential And you see VCs doing this all of the time. They reduce the risk in the startup to the point where if they are successful it doesn’t really matter. It makes no difference.”

Here’s some of the discussion in which Khosla shares his views on VCs, talks about the lessons that can be learned from failure and in the final video chats about ways to fix problems in education.

Like what you're reading? Subscribe to GeekWire's free newsletters to catch every headline


Job Listings on GeekWork

Find more jobs on GeekWork. Employers, post a job here.