Entrepreneurs and Criminals…maybe it is quite a fine line…

Sheena Leaf

I was delighted to meet the very interesting Sheena Leaf in Exeter on Friday.  That’s Sheena in the photo.  Sheena was originally a psychiatric nurse and these days is working on a project in Devon called “The Entrepreneur Inside”.  It’s a project that aims to deliver entrepreneurial education to prisoners and Sheena’s part way through a prison pilot that will connect offenders with business professionals and a regional university business school to uncover legitimate entrepreneurial potential.

This is something that’s never occurred to me before – although a cursory Google search identifies a couple of serious academic research studies comparing especially drug barons & gang lords with entrepreneurs.

I find this a fascinating idea – as it’s all to do with circumstance and life chances as well as morals.  On the flight back to Belfast on Friday evening I jotted down a few thoughts of my own about what some of the similarities are.  This is what I came up with:

·         We all like ducking & dealing – although perhaps we call that negotiation

·         We all like to make money – sometimes even just for thrills

·         Both sets lean towards being manipulative and control freaks – again we probably call that negotiation

·         We all resent being told what to do & like to be our own boss and make our own independent decisions

·         Everyone has a healthy disdain for the competition (there’s a famous story from a non-Disney theme park who used the objective “Kill Mickey” internally)

·         We all work hard to make ourselves indispensable to our customer base and we all want “addictive” products to sell

·         Both of us like spotting opportunity & backing “horses”

·         We all monitor and respond quickly to market trends

·         We both have a strikingly different risk profile than other groups of people

·         We all like to break the rules although we tend to do that by using armies of professional advisers to look for legal loopholes.

Interesting eh?  I’d welcome your thoughts on this & I wish Sheena every success with her ground breaking pilot. 



  1. Interesting stuff Mary. There’s always less that divides us than unites us in all the spectrum of human activity :)I wonder if some classes of criminal (or entrepreneur) are better described as “artists” – those that are properly creative in their creation or destruction. I don’t have much experience of criminals in real life so I always think of films like Batman where the Joker is quite clearly an artist as well as being highly destructive.Similarly there are many so-called entrepreneurs that are unethical and not creative as well as those who go into it to create something useful (and be paid fairly). Perhaps “privateers” is a better word for those less principled people.


  2. Thanks for that Mary. You have captured the essence of what ‘The Entrepreneur Inside’ is all about – the fact that we are all the same. Unfortunately, some of us are more ‘the same’ than others! The others don’t take the same opportunities; don’t play the game the same way and don’t have the connections. We’ll see if we can change that, shall we?


  3. I wouldn’t say it was ‘a fine line’ at all. I think we can draw a distinction between having a talent, or a skill, and choosing how to deploy that skill. For example, paedophiles are often very charming and articulate, and torturers have to feel a lot of empathy with their victims, in order to know how to hurt them. But that’s not ba reason to avoid people with those qualities.I don’t like it when businesses use language like ‘killing’ the competition or getting customers ‘addicted’. It promotes the idea that business is amoral by nature and we’re all struggling to get by, when in fact there are abundant opportunities to create more value, and deeper satisfaction.Sheena’s ideas about enrepreneurial education strike me as both a good way to help rehabilitate criminals, and an excellent way to sharpen the minds of ordinary, honest folk. Many of us undervalue our own talents, and though I’m not a Pangloss or a Pollyanna, I’ve found that people almost always become cynical and mean because they don’t believe optimist and generosity is a viable option.


  4. Good points Martin & Gordon & thanks for your input Sheena. Thanks also to the many people that gave their feedback & comments on Twitter including someone who pointed out that PR people & confidence tricksters also tend to use the same playbook.A bit of poetic licence used in this post Gordon – you know I believe in collaboration & indeed that was the topic upon which I addressed this year’s IoD conference on International Women’s Day as working in partnership as opposed to in competition would be one of my pet subjects.I thought this was a fascinating idea and one I wanted to promote a bit of debate around.


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