Editor’s Note: This post was originally published on Seattle 2.0, and imported to GeekWire as part of our acquisition of Seattle 2.0 and its archival content. For more background, see this post.

By David Aronchick

Congrats on becoming an entrepreneur, get ready for misery. Dave McClure’s extended rant telling you what an idiot you are to want to do a startup is a wonderful summary of all the many things that can and will go wrong with your new baby. It instantly reminded me of a great story in “D-Day, June 6, 1944”  by Stephen Ambrose. He writes of a private Charles East of the 29th Division, who was “told by his commanding officer on the eve of D-Day that nine out of ten would become casualties in the ensuing campaign[.] East looked at the man to his left, then at the man to his right, and thought to himself, You poor bastard.” If you want to do a startup, you have no option but to think this way, because you will fail. Your business is not the exception; your technology is not a revolution; your team is nothing special. You are going to fail. And the worst thing you can do in the world is try to prepare for that fact.

I commented about the dangers of (trying to) avoid failure not too long ago, but in summary, trying to mitigate your failure in any way is a complete waste of time:

  • You’ll never know where it’s going to happen.
  • Thinking about it will just dissuade you from taking the risks you need to do to give your business any chance to succeed.
  • In your attempt to avoid failure, you will so over-prepare, and have so little success in mitigation, that it will be worse than if you had done nothing at all.

So what should you do? Easy – go for the win.

I have met lots of entrepreneurs in the world, and one absolutely universal thing about them is that they are always going for the win. Going for the win means assessing the situation, choosing the best option and going full bore down that path without looking back for a second. A perfect example comes from the case study of Wesabi vs. Mint. Mint made a bet on Yodlee, a company that was “crumbling” and losing executives left and right. Risky? Sure. If Yodlee had gone down, that could have been the end of the business. But it paid off huge and even their competitor has to give them credit for one of the major reasons they won.

So what does it look like to go to for the win daily? 

  • Pick your horse and ride it no wasted efforts. If you think to yourself for even one second, “let’s do this just in case,” stop whatever you are doing immediately.
  • Measure measure measure. Your best bet for knowing you are going in the right direction is knowing your digits for victory. Could be revenue, traffic, conversion, pipeline, whatever it means to have a successful business. You need to be looking at that every day, and living and breathing those numbers. And when, not if, the numbers go south, you had better know why.
  • When the failure happens, you need to cut it out like a cancer and slam down the gas even harder. 

I disagree with Aaron Franklin,  in the context of your business, entrepreneurs MUST bet it all.  Waffling between one decision and another is a recipe for a drawn out and mediocre ride to failure. It is far better to fail quickly because it will give you far more opportunity to act on what you have learned. On the other hand, I do agree that entrepreneurs should never cash out their 401k or go into massive personal debt. Whenever I hear these types of horror stories, it is almost always because they have not failed fast enough.

“No one said it would be easy; but no one said it would be this hard.” The scope of the failure will be larger and more wide ranging, the type of failure will be completely unexpected, and the impact of the failure will be worse than you think your company could handle. If you are very lucky, you will still be in business after it happens. And if you are, you will be exactly the kind of company I would bet on to win it all.

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