How to get out of tight spots

Posted on June 1, 2012. Filed under: startups, venture capital |

Yesterday I caught up with an entrepreneur who is in a pretty tight spot…typically when faced with a problem or issue…I like to cycle through every possible move and then pick the one that has the highest probability of solving the problem at hand.  Usually there are 2 or 3 directions that seem viable and 2 or 3 that we can immediately throw out just by looking forward and playing out how all parties will respond to a decision…In this type of analysis I am rarely looking for a perfect solution or certainty…I don’t need to know for sure that a decision will solve the problem…just that it is the best of the available options…

Occasionally…however…a spot is so tight that none of the 6 options appear to have a high probability of success…it is very difficult to look at 6 alternatives, recognize that the best route is still only 15% likely to solve the problem…and still lean into that decision…but that is EXACTLY what you have to do as an entrepreneur…it is one thing to look for a 7th option…and sure…we can spend a few cycles trying to find it…but usually that which is not immediately apparent does not exist…it’s sort of like holding a crappy set of letters in scrabble…you can stare at the tiles for 10 minutes before you make your move…looking for that 40 point word that is going to get you back in the game on this hand…but the fastest way to a change is to play through the crap letters…make your 10 point word that doesn’t seem to help…but in doing so get yourself to a new context and a new set of letters…that present an option that is more attractive.

Our instinct when faced with 6 alternatives that seem unappealing is to freeze…not choose any because none seem forward moving…and we only want to move forward…but the reality is…something is going to happen if you make a decision…tomorrow or next week is going to look different than today…the tiles will shuffle…new words will appear…today’s decision is not your last decision…just a means to the next decision…when faced with 6 shitty routes…choose the least shitty…actively…lean into it as hard as you would a 95% solution…and wait for new words to emerge…they always do…companies only die when you stop reaching into the bag for new letters

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    I’m a NYC based investor and entrepreneur. I've started a few companies and a venture capital firm. You can email me at (p.s. i don’t use spell check…deal with it)


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