Why do some entrepreneurs hesitate close to success?

What happens when you finally agree with yourself that you are going to do what you have always wanted? Then in the next instant, when it is right there in front of you, within your grasp, you are confronted with the fear of actually getting what you want. And you call a halt, stop the presses and you want to renegotiate — with yourself.

It is always easier to not get something. In that way, you can desire, you can propose, you can anticipate, you can complain on all manner of things with yourself, and then when the gods say, OK, you can have what you want, you pull up and say, wait a minute. Not so fast, maybe I can have more? This is true in business, in finance, in relationships, in love. Case in point.

I have a client who told me on day one, four years ago, that he wanted to sell his company. Last week, he came in with the same lament, and in a short time on the whiteboard, I showed him a simple magic trick and poof, he is now in a position to sell his company and “get his number.” I handed him the goblet, but he was hesitant to drink from it.

Here is what fascinates me. The pause. The “well, maybe I could or should or might or maybe.” You told me what you want, and now you can have it. This issue haunts all of us, particularly entrepreneurs who define themselves to a large extent by their work, their title, their potential wealth. If I am not that anymore, then what am I?

I spend a lot of my time thinking about behavior and decisionmaking. And in this case, the real work for the client was not how to sell the company, it was all the other stuff about guilt, ego, repu

tation, definition of success, how much is enough etc. My shrink has Thursday morning open if anyone is interested.

My wife, Ms. Bry, and I do a podcast. On a recent one we got a fascinating question. Do entrepreneurs need courage? The answer we gave was a bit nuanced. I think courage is the byproduct of accurate risk assessment. Of course, hard things take courage to do, but the more powerful adjunct to courage is to try to avoid doing stupid things. Climbing a mountain takes courage, but doing it in flipflops with no water or food is stupid, not courageous. I think the startup game should be heavily informed by risk analysis. Data is power, understanding data is wisdom, and with that wisdom

comes the willingness to act courageously. And believe me, if it were easy, everyone would do it.

I was frustrated with myself recently when I could not effectively connect with an entrepreneur. He came in and I listened and probed for 90 minutes, and at the end, I realized that I had made no visible impression. Was it my fault or his? I think it was me. And the issue was that my frame of reference and analogies were foreign to him. He was not from America originally, so idiomatic venture capital speak made no sense to him. The set phrases and references in my playbook were meaningless to him. It was on me to figure out a way to give the information differently.

There is a famous line from the TV show “Ray Donovan.” He is asked by a wealthy man to fix a very difficult problem for him, to achieve a different result.

Donovan quotes him a price of $1 million. The man is surprised and asks Donovan, just what exactly do you do for $1 million? Donovan says, “I change the story.” That line so impressed me, I had it lithographed and put on the wall in my conference room. Think about the elegance of that idea. Same cast of characters, same puzzle pieces, but if I can reassemble them in a different order, then perhaps the viewer will see it another way, my way. I love that possibility.

When you are facing challenges in your company, what about considering an alternative story? Same letters, different words. Call it Boggle for startups.