What Successful Entrepreneurs and Successful Criminals Have in Common

By Timothy Askew; reprinted from Inc. with the kind permission of Timothy Askew.

I found this line in a recent John Grisham bestseller.  “Prisons are fascinating places, especially when the inmates are educated white-collar types.”

The distance between the criminal and the successful entrepreneur is not so very far.  We both intuitively operate out-of-the-box with an instinct for not accepting the status quo.  We both are not inclined to accept the tyranny of the given.  We both intuitively color outside the lines.

Note the work of Bill McCarthy (UC Davis) and John Hagan (Northwestern) who report that people who are the most successful at crime have a strong desire to succeed, to take risk and to live by their own rules.  Hmm.  Sounds very much like most driven entrepreneurs.

I recently met a wonderful man named Jeff Grant who heads up an organization in Connecticut called the Progressive Prison Project, a non-profit dedicated to guiding and supporting business owners and white-collar executives. who have been accused of, convicted of, or been incarcerated for crimes ranging from DUI to financially motivated felonies.

Jeff Grant feels entrepreneurs, single-practitioners, DBAs, and small businessmen increasingly face exceptional dangers of drifting into damaging legal problems and even incarceration for a variety of reasons.

1. Entrepreneurs lack the infrastructure resources to keep abreast with the increasingly complicated and onerous regulatory load emanating from all levels of government.  They are  overwhelmed with putting out constant fires in their real business. They have neither the time nor the inclination to spend days boning up on staying exactly on the right side of evolving law.
2. Furthermore, entrepreneurs frequently don’t even have a peer-level partner to challenge them on their interpretation and/or ignorance of compliance issues.  It becomes all too easy to carelessly cut corners.
3. The combination of daily pressure and aloneness may make it tempting to make a deal with the devil—a deal often abetted by drugs or alcohol or sex, which fuzz over and break down a  man or woman’s moral center.  More than in most professions, entrepreneurs may be tempted to take ethical risks when bills threaten to overwhelm.
4. Entrepreneurs often have big egos and suffer from hubris.  When they do not have the tools or knowledge for compliance, it is hard for them to admit it.  They (we) can suffer from  grandiosity.  We may begin to exaggerate, to lie, to puff ourselves up.  We sometimes don’t want to admit a core fear that we may not be the master of the universe, that we are not Elon Musk, Steve Jobs, or Mark Cuban.  Not even remotely.
5. Entrepreneurs are dreamers who can drift into not living in the rigorous reality of what their life actually is.

Jeff Grant can speak with authority on this subject.   He spent 14 months in a federal prison for a financially motivated crime stemming from bad decisions made under the dual influence of prescription drugs and financial pressure.

Grant headed a highly successful legal practice in Westchester County, New York.  The Greenwich Sentinel reports Grant as saying, “In the course of rehabilitating an [achilles heel] injury, I got hooked on prescription narcotics.  Doctors were more than happy to continue to prescribe them to me, and I took them for about ten years.”

Grant gradually lost control of his firm and eventually couldn’t meet payroll—at which point he made up the shortfall by dipping into client escrow funds.  He lost his company, his marriage, his money, his respected position in the community, his freedom.

What he found in prison was that there was little or no support for small businessmen like himself.  His present wife and Co-Founder of the Progressive Prison Project, Lynn Springer, puts it this way:

“Typically in the upper-middle class, where white collar criminals tend to come from, the husband has been the bread winner.  Generally, these are people who are considered to be very well off.  All of a sudden, all of their assets may have been seized by the SEC.  They don’t know how they are going to buy food, how they are going to heat their home, how they are going to put gas in their car.”  (The Greenwich Sentinel)

Furthermore, when Grant came out of prison he had to deal with what he calls the “schadenfreude” of many folks who took a closet joy in seeing the mighty fall.  Grant thinks there is an ecosystem problem in our society in which the rich person and the celebrity are both adored and virulently hated, and there is little sympathy, governmental or societal, for the fallen entrepreneur, who many see as a stand-in for the greedy 1%.

Grant speaks with power out of his own humiliation and suffering.  He has the well-earned authority of a deeply humbled man.  After his release from prison he got an M. Div. degree from Union Theological Seminary and founded the Progressive Prison Project, which is the first ministry in the U.S. created to provide support and counseling to individuals and families with white-collar and other non-violent incarceration issues.  (For further information on Jeff Grant try www.prisonist.org.  Also related to this issue check out my Inc. column of last year titled Criminals and Entrepreneurs.)

Robert Rohr, in his excellent book on addiction, Breathing Under Water, says, “People who fail to do it right, by even their own definition right, are those who often break through to enlightenment and compassion.”  Like Jeff Grant.  Thank you, Robert Rohr.

Image: Pixabay.

Tim Askew is the owner of sales firm Corporate Rain International and a member of the Inc. Business Owners Council. He has several advanced degrees, and has been a tennis pro, actor, opera singer, Broadway producer, dishwasher, bartender, minister, and college assistant dean. Askew is the author of the new book The Poetry of Small Business (available on Amazon).  @TimothyAskew