Billionaire investor Vinod Khosla's best advice for success: 'Your willingness to fail is what will let you succeed'

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vinod khosla

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Khosla Ventures partner and Sun Microsystems cofounder Vinod Khosla

Billionaire Vinod Khosla is a true Silicon Valley legend, with career highlights including the founding of Sun Microsystems, a long stint at venture capital firm Kleiner Perkins, and now, one of the most sought-after investors in tech as the leader of Khosla Ventures.

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But on stage at this week's Structure conference, Khosla reminded the crowd that even his successful career wasn't without its setbacks.

"I've failed at more things than anyone I know," Khosla says. "No one remembers the failures."

To prove it, Khosla brought up The Data Dump, a company he cofounded in 1981, about three months before Sun came into being. The Data Dump and Sun had the same investors, Khosla says. In fact, Khosla says, he cofounded both companies with Scott McNealy.

When Khosla asked the crowd if anybody remembered The Data Dump, only a very few hands went up. McNealy once described it as a "total disaster," and Khosla acknowledges that it wasn't long for this world.

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Still, he says, from The Data Dump, he went on to start Sun, a company that was massively successful for a long time, and which basically invented several of the main concepts that are critical to computing today. He just had to pick up and move on to the next big idea.

Scott McNealy, Sun Microsystems

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Scott McNealy, cofounder and former CEO, Sun Microsystems

"Your willingness to fail is what will let you succeed," Khosla says.

And Khosla, a big proponent of the idea that nimble little startups can topple big established companies, took the opportunity to jab at what he sees as a lack of innovation from tech leaders.

"It's one of the reasons larger innovations don't come out of larger companies, because they don't like to fail," Khosla says.

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