Keen On… Vinod Khosla: “I’ve Failed More Times Than I’ve Succeeded” (TCTV)

As the co-founder of Daisy Systems, the founding CEO of Sun Microsystems, a general partner at Kleiner Perkins and the founder of Khosla Ventures, there are few men who appear to have failed less than the legendary Vinod Khosla. And yet, when I caught up with Khosla after he keynoted yesterday’s excellent FailCon conference in San Francisco, he confessed to me that he’d failed more times than he succeeded.

Failure, of course, was the theme of the day at FailCon. And Khosla had much else to say about failure – arguing that the teachers in American schools are all failures and suggesting that all experts are full of “crap”. In Khosla’s mind, I suspect, what’s so interesting about failure is that you have to experience it in order to be successful. And that’s why, he told me, the success of technology entrepreneurs like Jack Dorsey and Max Levchin is dependent on their earlier failures.

This is the first of a week long series of interviews I did at FailCon on failure, thank you to for helping us with the filming. Check back tomorrow when MySpace co-founder and CEO Chris DeWolfe talks to me about how his failure at MySpace has inspired his new company Mindjolt.