Till his early thirties my brother-in-law was a failed entrepreneur. After college he got a job as a sixth grade teacher in Camden, New Jersey and made barely enough money to support a family.  At one point (1975) he importuned me to get a part-time job for my sister: “Zelda just had a baby.  [Translation: we have an extra mouth to feed.]  Could you get a job for Zelda where you work, something she could do from home?  She can’t go to a regular job.  She has to stay home to take care of the baby.”  Did he ever think of getting a better paying job himself?”   He worked as a teacher till 1983, when he turned 36. He supplemented his income with a variety of endeavors such as selling encyclopedias and correspondence law courses.  In about 1972 he came up with the idea to write a guidebook for parents on how to help parents teach kids to read.  He would self-publish the book and that could be a source of income.   He ventured into illegality, filing at least one fraudulent negligence law suit, using manufactured evidence of injury. He contemplated illegal schemes like setting up a fraudulent Medicare clinic. There was a decidedly psychopathic trend in his personality. When he told my mother about his plan to create a fraudulent Medicare clinic, she responded with concern: “Isn’t that illegal? You could go to prison, couldn’t you?” He replied: “What’s the difference if nobody finds out?” My sister said she had to cut off my brother-in-law’s contact with one friend because they would discuss illegal money-making ventures when they got together. My sister said: “I’m afraid he would actually do these things because he doesn’t know right from wrong.   He could easily get caught up in illegal activities and not even know they were illegal.  I told him to stop seeing ——.” In his twenties my brother-in-law could be described as a “failed entrepreneur.”

In his thirties he created a successful mortgage business and made a good living. Could we say that he went from being a failed entrepreneur in his twenties to a successful psychopath in his thirties?  It’s been said that the entrepreneur is a successful psychopath while the psychopath is a failed entrepreneur.

The psychoanalyst Salman Akhtar, M.D. offers the following observations that might offer insight into my brother-in-law’s personality.