My Time in Jail


Fancy careers force people to build walls.  These walls protect lucrative franchises and social constructs.  These walls also hide the world from careerists like me.  Upon writing “WEALTH, ACTUALLY”, I have been able to meet scores of people and indulge my curiosities in the areas that the banking industry and society as a whole avoids like the plague.  One such curiosity was my recent day in jail.

This experience came to me via Steve Sims, entrepreneur and author of “BLUEFISHING”.  We connected around the release of our books and mutual interests.  He suggested that I join a group he was assembling for a day in jail through Defy Ventures.  The goal was to make a strong impact on a group of people that were preparing for their release by developing entrepreneurship skills and breaking the cycle of recidivism.  Through a mix of rabid self-interest in promoting my book and other projects, curiosity and altruism, I was easy to convince.

Defy’s mission is simple and they state it eloquently in their materials (WWW.DEFYVENTURES.COM):  “We harness the natural talents of currently and formerly incarcerated men, women, and youth and redirect them toward the creation of legal business ventures and careers. Defy offers a suite of services that includes intensive personal and leadership development, competition-based entrepreneurship training, executive mentoring, financial investment, and business incubation. By engaging top corporate executives, investors, and entrepreneurs nationally, Defy catalyzes broad scale personal and economic opportunities for people with criminal histories, and shatters perceptions of one of the most stigmatized and overlooked populations in America.”

We assembled at Kern Valley State Prison just north of Bakersfield, California.  KVSP is an all-male level 4 maximum security prison that houses 4,500 inmates.  It is no country club.  At all.  People are here for doing awful things. We broke off into groups to listen to pitches from the 100 or so inmates that had gone through the entrepreneurship program.  They asked for counsel and resources for their business ideas.  We heard their stories.  We found commonality in our experiences.

I took away a few indelible lessons.

  • Incarceration in this country is a death sentence. It just takes longer.  It creates a cycle of dependence and helplessness that is extremely difficult to break.  Once branded with a felony conviction, most of the resources and opportunities in this country are no longer available (including the banking system).  As a result, successful reintegration into society is a low probability event.
  • Entrepreneurism is a universal (and powerful) language.  I witnessed as much talent, hustle, ingenuity and negotiation in a day in jail than I have in 16 years in private banking.  Contrary to what you might think, there are fewer distinctions between successful entrepreneurs on the outside and prisoners on the inside.  Many times, that distinction is a matter of opportunity and circumstance.
  • Entrepreneurship is a camaraderie.  It is also for misfits- people who have more to say than a rigid corporate structure will allow.  I met a bunch of like-minded go-getters from around the country who joined Steve simply because they thought it would be a good idea.  It was a terrific energy.
  • There are very bad people in jail and they do not belong out in the world. There are also people who have done terrible things in the past who want to chart a different course.  There should be more resources to de-stigmatize and develop this vast pool of potential.  As stated in The Bronx Tale, “the saddest thing in life is wasted talent.”
  • Our criminal justice system is in dire need of reform. The seeds of this statement were planted for me a few years ago when the “Kids for Cash” scandal erupted in Pennsylvania.  (  If the Koch Brothers and the Kardashians are of the same mind on rethinking the purpose of the prison system, then there must be something to analyze.
  • The most amazing statistic I heard all day is that inmates lives are structure so they have to make fewer than 10 decisions/day.  Most of those have to do with survival.  I make 50 decisions when I wake up just to get out the door.
  • There are people inside the criminal justice system who want to see inmates succeed. I met many of the administrators and guards who believe in the programs and were excited to see the investment of time and energy.
  • Our lives are fragile and the support systems we have around us are vital. Very few of us can say that they have never been held accountable for doing something illegal (I certainly can’t).  Now imagine that you have a target on your back, can’t envision a life beyond the age of 21 and that you will likely always be in the wrong place at the wrong time without proper representation.
  • There are a host of characters in the financial services world that should get on their knees and thank their God every day that they are not in prison. They know who they are.
  • A visit to a prison is a terrific way to earn more about yourself, build links within teams in a short period of time, and establish perspective when the absurdities of a corporate existence have taken on a life of their own.

Feel free to reach out to me to find out more about Defy Ventures’ programs or to hear more about my experience.

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