Jim Duffy: Mob rule calls tune and not just for Tony Soprano

Tony Soprano (James Gandolfini) is a natural leader and always looking for an opportunity. Picture: AP

There were times when I actually felt sorry for Tony Soprano in the hit HBO mini series The Sopranos. Which, when I reflect on it, is pretty crazy as he was a crook, a mobster and a killer. But, when I watch the boxset, which I do at least once a year, I can empathise with him ... at times. Tony would say he never really had a choice but to follow in his father’s footsteps as the local mafia boss in New Jersey. Indeed the Alabama 3 hit theme song suggests this: ‘You woke up this morning, got yourself a gun. Mama always said you’d be the chosen one.’ So, Tony was anointed the moment he was born. As the family dynasty grew, there had to be a succession plan – a wee bit like our Royal Family – a pecking order and only one gets the top job. But Tony is more than just the boss: he is the entrepreneurial leader who has to keep the cash tumbling in while juggling multiple balls.

So, there he is, Boss, and top of the pyramid. One could be forgiven for thinking he would then have a nice life with plenty of wonga. How wrong could we be. Like all entrepreneurial leaders, Tony is only as good as the team he has in front of him and in how he leads, motivates and inspires. It’s here where it gets a bit complicated for him.

Firstly, any entrepreneurial leader has to know his or her own strengths, weaknesses, shortcomings, gaps and drivers. To lead any team, one needs to have passion and belief in what they’re doing and where it is all leading, but understanding that the leader can’t do it all and doesn’t have all the answers.

The well-rehearsed Shakespearean phrase ‘To thine own self be true’ is crucial to all leaders, and like all leaders, Tony struggles here. His torrid relationship with his mother plays out in his psyche, which leads him to seek the services of a psychiatrist. With some cognitive behavioural therapy and some Prozac, Tony peps up a bit. But, the moral of this one is that a good leader, Mafioso or not, needs to have his or her head sorted and recombobulated as far as possible, so they can lead others.

Tony has a larger-than-life personality. When he enters the room his capos and his henchmen are immediately aware the big man is there and one can feel the deference. I would argue that Tony is an ENTJ - a type of personality categorised and explained by the Myers Briggs personality system (extraversion, intuition, thinking, judgment). One of the key corner boxes, ENTJ’s are natural leaders and incidentally excel in the corporate world as chief executive officers.

He’s certainly an alpha male. This bodes well for his role as boss as he has some tough wise guys to deal with. Entrepreneurs building businesses from scratch to securing significant investment need to have a strong belief in themselves and have their heads geared for growth and tough decisions made in the context of ambiguity. Like Tony, they have to project themselves within their teams and investors are looking for them to be strong and decisive. But I’m not sure about the alpha male bit – a big set of balls can get in the way in business.

Tony Soprano is a great communicator. He speaks regularly with his capos, advising them of what he wants done, while schooling them in the political science of mob politics.

He has the New York family to deal with and Johnny Sacrimoni constantly undermining him and causing him issues. He has his uncle, Junior – Corrado Soprano – battling against his decisions and making his life difficult from within the business as well as outwith. So, Tony has to navigate all this, while keeping his team on track – just like the entrepreneur who has to deal with so many distractors.

Constant and consistent communications are key to keeping the canoe heading in the right direction with all the team paddling in concert. When one of the team doesn’t want to toe the line, there is no room for negotiation in an entrepreneurial venture.

As Tony says: “If you can quote the rules, then you can obey them.” There’s a great quote that states “you can’t run a marathon with a stone in your shoe”. The entrepreneurial leader has to cut quickly for the sake of the whole business. Although, Tony does take this to the extreme as dissenters often get taken ‘care of’ - clipped or whacked. Not recommended…

Finally, Tony is opportunity hungry. His commercial radar is up all the time. Whether it’s “boosting” some Italian tiles from a truck, skimming the numbers at his own in-house pop up casinos or owning a stake in Artie Bucco’s restaurant, Tony knows the margins to be made in each business model and how to squeeze out value for him, his team and his masters in New York. He takes counsel from Hesh Rabkin on some of the bigger deals and opportunities. So too, the entrepreneur has to be commercially savvy. In most instances, he/she is pitching for one type of funding or another and so has to know how much they need and how they are going to spend it wisely to make a return. Knowing their numbers and who to turn to for advice is a key skillset for entrepreneurs who want to build, grow or scale.

I’ve learned a fair bit from the Sopranos and could wax lyrical here on so many of the business models that emerge in the show. But, for any entrepreneurs out there feeling the heat in the throes of building a company, spinning plates, hiring new staff, making intuitive decisions on the fly and piecing people and deals together, with no safety net, let’s give the last word to Tony Soprano – “a wrong decision is better than indecision”.

• Jim Duffy is the Chief Executive Optimist of Entrepreneurial Spark