The Best Entrepreneurs Know How To Fail Fast

Last night at the TechStars Boulder Mentor dinner I got into a conversation about what makes a better CEO of a new startup – an experienced entrepreneur who’s last company was a failure or a big company executive with a stellar pedigree who has never worked in a startup.

Give me the experienced entrepreneur whose last company was a failure 100% of the time.  The cliche “you learn more from failure than success holds true”, but more importantly the dude that just came off a failure and is ready to go again is super-extraordinary-amazingly hungry for a success.  It doesn’t matter how much money he’s made in his past companies – once he decides to go for it again he’s going to be ready to crush it.

Spend four minutes listening to Mark PIncus’s interview on Vatornews about his lessons from Tribe – fail fast.  Two great entrepreneurs that I’ve worked with before (and intend to work with again) sent it to me this morning with a note saying “wow – awesome – must watch.”  (n.b. each of them had one success and one failure before I funded their third company, which was a huge success.)

Mark is the CEO of Zynga (I’m on the board).  I love working with Mark – I’ve known him since the mid-1990’s and funds I’ve been affiliated with invested in his first two companies: Freeloader and SupportSoft.  Both were successes.  We didn’t (for a variety of reasons that I can’t remember) invest in Tribe which was a failure.  When Mark started talking about Zynga, it was an easy decision to jump on board and do the first round funding with Fred Wilson at Union Square Ventures.

Mark amazes me on a regular basis – not only has he synthesized everything he learned from Tribe, he has developed unbelievable sense of self-awareness as an entrepreneur and a human that helps accentuate the things he’s great at while opening up for help when he needs it.

Note to everyone: check your pedigrees at the door – tell me about your successes and failures when we meet for the first time.  And fail fast.