Back to the Brig: Sharing Stories of Failure to a Captive Audience

Published in the San Diego Union-Tribune, August 31, 2015

Back to the brig.

Getting invited back to “do Miramar” is a little like your agent telling you that Letterman wants you back to do five minutes of stand-up, except in this case it is 90 minutes on entrepreneurship to 75 prisoners. And, as always, it is nice that I get to leave the brig when it is done. I am sure one of these times they will throw away the key.

The military has a program that encourages and teaches business skills to their inmates, since all of them eventually get out and all of them desire to be integrated into civilian life again and either get jobs or start companies. Recently, I was privileged to talk to “my gang” for the fourth time, and I can tell you that they are without question highly interested and focused and intelligent and ready to take charge of their lives.

As a note, the recidivism rate at the brig is less than 2 percent. That shows the value of providing programs and education.

We discussed many of the big ideas that readers of this column know by heart, as well as a couple of personal war stories, including, but not limited to, a recent failure I was involved in. You learn more from the failures than you do from the successes.

One of the themes this time was “I waited too long.” We all know that the hard decisions in companies are often uncomfortable and even though we recognize the issue, there is still a distinct tendency and desire to avoid unpleasantness. This is a human trait, not unique to entrepreneurs. I recently fell victim to this disease — the “I hope if I look the other way, it will magically go away and everything will be fine again syndrome.” (Find me a biotech that can solve that disease, and I am the lead investor.)

I waited too long to fire the CEO, and when the fan got hit, the ensuing issues were ugly and much of the pain and the losses could have been avoided if I had trusted my gut earlier and been willing to deal with the hard conversation when I knew I should have.

Note: Read “The Hard Thing about Hard Things” by Ben Horowitz.

In the same vein, I recently had a “stock vesting” issue in another company. The CEO finally faced that we had to terminate an employee, but by waiting a year too long to do this, he created conflict among the other employees who saw the unfairness of the situation, while at the same time creating unnecessary dilution for the whole company.

I have another company with a CEO who needs to have an unpleasant conversation with the lead investor. Again, my advice is to face it and do it now. And while we are on the subject of unpleasant conversations, let’s go back to the brig. One of the issues the prisoners have to deal with when they get out is their record. In certain cases, they have a dishonorable discharge; in other cases, they have a record as a felon.

I was asked: “What do you tell a prospective employer?” The answer is: Tell the truth and tell it early in the interview. There is no place to run, no place to hide, do it upfront. You made a mistake, put it on the table. I do not believe that fact alone will disqualify you for a job. I am always a fan of and a supporter of the second chance. If at the pearly gates, I am asked do I want justice or mercy — no contest, I will take mercy every time.

And finally on the subject of incarceration and educational programs, in the past year, I have also been contacted by several East Mesa detention facility inmates who read this column. They have asked me to come and talk to them. Unfortunately, although I have tried several times, I have been unable to get anyone in the Sheriff’s Office to respond to my request. However, I will continue the effort.


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