Failure in context

A few nights ago, I had dinner with some special guests who were visiting Boulder and Techstars. They were Joachim and Steven who are with the Singapore government and Ken Zolot, a Techstars mentor and MIT Lecturer from Boston who is also a Senior Fellow with the Kauffman Foundation and is working to understand entrepreneurial ecosystems.

Among many interesting parts of the discussion, one topic stuck out for me. It was about how failure is almost celebrated here in the US in the context of entrepreneurship. Things have changed in Singapore, but apparently Asian culture has historically made it shameful to fail. Of course, in the US it’s not exactly great to fail, but it certainly falls short of shameful. In fact, as the saying goes, if you haven’t failed you haven’t pushed your limits.

This made me think back to a video from Big Omaha that I had seen recently of Jason Fried saying that somehow “failure became cool” and he said that he didn’t get the “fail early, fail often” mantra it at all.  Ever since I watched this the first time, it had bugged me. So I went back and watched it again. Then I read his related post on the 37Signals blog.

Some of this is semantics – I think “fail early, fail often” is usually used in the context of micro-failures and experimentation and not at the macro level of the entire enterprise.

In a post supporting his position that “this industry’s obsession with failure has got to stop“, Jason says “Many investors and entrepreneurs out there believe that you should fail a few times before you succeed.” I’ve never once come across this attitude, but I suppose it could exist. In clear contrast, Brad Feld has said that his favorite entrepreneur to invest in is a successful one coming off a recent failure. This is not just due to the lessons learned, but also because that entrepreneur is going to be very, very hungry. Of course he’d be somewhat less likely to invest in an entrepreneur who has failed and failed and failed with no success.

I think there is some confusion here between “fail early, fail often” and “fail fast.” Failing fast is about the case where you’re on a path that is going to fail and the writing is on the wall. In that context, failing the company fast makes sense.

When people say “Fail early, fail often” I think they generally mean something different. Of course people aren’t encouraging you to go out and start companies that fail just for the experience of it as if it somehow makes you stronger!  Rather, it’s about testing and trying until you get it right – generating an overall success. Think little failures, early and often, and you’ve got the right context for “fail early, fail often.”

That’s what was bugging me. To me the two sayings are used in completely different contexts. Am I right? What does “fail early, fail often” mean to you, vs. “fail fast”?

UPDATE: After writing this, I watched Micah Baldwin’s video from the same event, where he made a similar point about the confusion about the “ending point” of failure in Jason’s talk at about the 11 minute mark.

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