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Freedom to Fail – Part 1

September 23rd, 2009 by admin Leave a reply »

This past month, I was struck by something that Vinod Khosla brought up at the Haas School while accepting a “Lifetime Achievement” award, and have been turning it over in my mind many times… Khosla is responsible for major successes at Daisy Systems, Sun Microsystems, huge portfolio wins at Kleiner Perkins (KPCB) over the years, and is now responsible for at $1+ billion new fund at Khosla Ventures. What would you guess contributed most to his success: an eye for technology? Luck? Choosing the right teams?

Khosla’s secret to success

When asked what most contributed to his success over the years, Vinod boils it down to this: the Freedom to Fail. According to Khosla and many others, if we feel that we have the freedom & ability to push ourselves to the limit, create new ideas, and start companies we believe in – we are more likely to succeed. An entrepreneur who allows FUD (Fear, Uncertainty, Doubt) to creep in about his/her abilities and leadership, and fears failure is more likely to fail. More on this in a video of Vinod from SDForum awards 2 months prior.

Lessons from Early Yahoo

As part of the original Yahoo team, I observed this first-hand. There as a general feeling among the team that “hey, if this doesn’t quite go the way we imagined, we’ll fix it and try something else.”  If the worldwide web (or Yahoo)  didn’t quite take off, some of us would  just go back to their happy lives as grad students at Stanford and continue on.   Of course that didnt’ happen.  And, it was later on, after the company tasted big success that fear of failure crept in.

So, I have been wondering: what’s the link between “freedom to fail” and creativity in a start-up?  Do most successful entrepreneurial environments include this element? Is Freedom to fail learned or are some of us born with a certain “chutspah” that keeps us from thinking about failure? Can an entrepreneur deliberately set up a “Freedom to Fail” culture?  (More next post –>)

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