Disappointment

How do you handle disappointment?  It makes a difference in your responses to life.  It also makes a big difference in your response when you are the CEO of a startup.

I came back to Chicago with the expectation that my apartment would be mostly done.  We walked in and it was no where near the place it should be.  Going into the project, my expectation was set by the contractor that this was a 50-60 day project.  We are on the 4th month.

If he was an entrepreneur leading a startup, we’d be looking for a new CEO.  He just cannot execute.  The important stuff doesn’t resonate with him.

The problem for my wife and I is it’s totally screwing with our life.  We are not unfamiliar with the rehab process. We had a home in Geneva that was destroyed by water after we built it.  We rehabbed a house before that and we rehabbed a co-op in Chicago.  This one is taking longer than the co-op but I digress.  For us, when life hands us lemons we try to make lemonade.  That’s what I tried to do on this recent trip.

As an investor when disappointment happens, it’s often best to take a step back.  Try to figure out the macro picture first.  Once you see it, zero in on the things you can change to effect a different outcome.   In our business sector of B2B Fin tech it’s generally not an idea that just doesn’t work.  It’s about execution.

Seeing the macro helps you understand if the feeling of disappointment is one you should be feeling or not.

Sometimes the important stuff doesn’t resonate with the CEO of the startup.  They either are blind to it, or they don’t want to see it.  They might not see the forest because of the trees and that is where a thoughtful investor can help out.  It’s a tough conversation to have.  How the investor handles it can mean the difference between success and failure.

Often, you might see it in either communication, or the board deck.  Sometimes communication ceases.  It’s important to keep those lines open when a company is struggling.  Board decks emphasize things that are wrote and not important to the survival of the firm.

On Monday I will meet our contractor.  I am prepared for a lot of excuses.  No one likes to take responsibility and say it’s their fault.  We don’t like to admit failure.  Especially when money is at stake.  The correct response is to take responsibility and say, No excuse sir, and move on.  I learned the ethos of No Excuse sir back when I was 18.  The thing is, when you really learn what it means it is empowering and forces you to do better. But, you have to move on changing the way you do business and that’s where the tough conversation ensues.  How are we going to change the process so we can execute better?  People don’t like change.