10 management lessons from highly successful gangsters

By Jeppe Kleyngeld

Running a large company or criminal empire, what’s the difference? The demands for its managers and leaders are very similar for sure. As a leader, your vision needs to inspire others and your actions need to have significant impact. You also need to be able to effectively solve problems and prevent painful blunders. Taking a close look at 10 highly successful gangsters from popular movies and television series can be inspirational. Eventually most of them went down, but they all had impressive careers as criminal CEO’s. What can business leaders learn from their successful approaches and significant failures?

1. Plan all your actions carefully
Neil McCauley
The Gangster: Neil McCauley, Heat

The Lesson: In the spectacular opening scene of Michael Mann’s Heat, criminal chief Neil McCauley and his team of robbers manage to take down a huge score. The key to their success? Planning, planning, planning. McCauley is a perfectionist; every detail needs to be scrupulously prepared, nothing can be left to coincidence. It there is even a slight chance that something is wrong; he will walk away from a job no matter how much money is at stake. Off course, there is a slight bump in the road for McCauley and his team later on, but that is only because pulling armed robberies is a highly volatile business. But even with a terrific investigation team on their tail lead by a fanatical Al Pacino, they manage to take down another – even larger – score later on in the movie.

2. Build a team you can rely on
Joe Cabot
The Gangster: Joe Cabot, Reservoir Dogs

The Lesson: ‘I should have my head examined for going with someone I wasn’t a 100 percent on…’ Yeah, you should have Joe. As a manager, your most important task is to choose the right people around you and make them perform optimally. When you have a crucial project to realise – a diamond heist in Joe Cabot’s case – you don’t want to take any chances on whom you hire for the job. Joe’s negligence at this point, allowed a special LAPD-agent to infiltrate his crew, leading to a disastrous outcome for the project and all those involved.

3. Always look out for opportunities and know when to strike
Henry Hill
The Gangster: Henry Hill, GoodFellas

The Lesson: In Wiseguy, the novel on which the classic mob movie GoodFellas is based, protagonist Henry Hill describes his bewonderment at how lazy many people are. Great entrepreneurs like him are always looking for new ways to make money. Once in a while, a golden opportunity arises and a highly successful business manager will recognize this once in a lifetime chance and grab it. In Henry Hill’s case, this was the Air France heist in 1967. He walked away with 420.000 US dollars from the Air France cargo terminal at JFK International Airport without using a gun; the largest cash robbery that had taken place at the time. This was Hill’s ticket to long term success within the Mafia.

4. Analyse, decide and execute with conviction
Michael Corleone
The Gangster: Michael Corleone, The Godfather

The Lesson: Your success as executive depends for a great deal on the way you make decisions and follow them through. When his father, family patriarch Don Vito Corleone, is shot by Virgil ‘The Turk’ Sollozo, Michael Corleone knows the threat of his father’s killing will not be over until Sollozo is dead. That is his analysis. Then, without any hesitation, he decides to kill Sollozo despite the hard consequences that he knows will follow. The third part – the execution – he performs flawlessly, killing Sollozo and his bodyguard Police Captain McCluskey in a restaurant. Michael later in the film again proves to be an extremely decisive leader when he has the heads of the five families killed when they conspire against the Corleone family.

5. Support the local community
Young Vito Corleone
The Gangster: Young Vito Corleone, The Godfather Part II

The Lesson: For long term success, you need more than just great products (in the mob’s case: protection, gambling and theft). You will need commitment from all your stakeholders and especially goodwill from the communities you operate in. Young Vito Corleone sees that gangster boss Fanucci is squeezing out everybody in the neighbourhood he lives in. Nobody is happy with him. So he murders Fanucci and takes over as neighbourhood chieftain. Rather than squeezing out people, he starts helping them. Every favour he does for somebody, earns him a favour in return. Those are a lot of favours and a lot of people who think he deserves his success and wealth. They are willing to give everything for their Don.

6. Don’t be afraid to use your subconscious
Tony Soprano
The Gangster: Tony Soprano, The Sopranos

The Lesson: As a leader, you want to base your decisions on hard facts as much as possible, but sometimes your intuition is much more powerful than the greatest performance dashboard in the world. In the first season of HBO’s monumental Mafia series The Sopranos, family patriarch Tony Soprano’s own mother tries to have him whacked. He had revealing dreams about this before it happened, but refused to look at the painful true meaning of these dreams. Through therapy, he learned to use his subconscious like a true expert, so when his friend Big Pussy Bonpensiero starts ratting for the FBI in season 2, he knows something is wrong. In a fever dream, Big Pussy (as a fish), reveals the hard truth to Tony. When he wakes up, he knows exactly what to do. Big Pussy must sleep with the fishes. Tony’s new ability to listen to his subconscious makes him a much more effective leader.

7. Think and act faster
Nucky Thompson
The Gangster: Nucky Thompson, Boardwalk Empire

The Lesson: After a botched assassination attempt on bootlegger and crooked politician Nucky Thompson, his enemies are left numb and indecisive of what to do next. Nucky – on the other hand – immediately makes a counter move. He goes to see his enemies and tells them the attempt on his life changed his perspective on things. He will abandon the bootlegging business and politics, so his enemies can take over. In secret however, Nucky books a trip to Ireland the next day, where he purchases a huge amount of cheap and highly qualitative Irish whiskey. His enemies underestimated him. By thinking and acting faster than his opponents, Nucky manages to surprise them and outperform them in business.

8. Take compliance seriously
Al Capone
The Gangster: Al Capone, The Untouchables

The Lesson: He was the king of his trade; the bootlegging business in Chicago. He made millions importing booze and selling it to bars and clubs. The thing that brought him down was income tax evasion. Managers can learn a simple truth from this mistake; compliance is your license to operate. Off course in Capone’s case this was a little different because he did not have any legal income to begin with, but many CEO’s of businesses have fallen into the same compliance trap. Sure, sometimes it is cheaper to pay a fine than to spend a fortune on meeting some obsolete policy, but you should never fail to answer to the most important rules and regulations. So even when it is sometimes tempting to bend the rules, in the end: being non-compliant is always more costly than being compliant.

9. Ride the Industry Waves
Tony Montana
The Gangster: Tony Montana, Scarface

The Lesson: Every industry has its waves, and a great CEO knows how to ride these waves. Take the drug business in the 1980’s. Cocaine was coming up big time in Florida. After Montana gets rid of his weak boss Frank, he sets up a massive cocaine trade in Miami and surroundings. His supply chain is very efficient. He imports the stuff straight from the source in Bolivia. Nobody can compete with that. It isn’t before long that Montana is Florida’s one and only cocaine king.

10. Keep your friends close and your enemies closer
Don Vito Corleone
The Gangster: Don Vito Corleone, The Godfather

The Lesson: You want to know what your competitors are up to? Invite them over for dinner and a meeting. Don Vito Corleone does it all the time. When he invites the heads of the five families for a sit down, in this powerful scene in The Godfather, he learns a great deal. It is not Tattaglia he should worry about, but that treacherous Barzini. Now that he understands the conspiracy against the Corleone family, he can help his son Michael take the necessary precautions.

Jeppe Kleyngeld is content manager from the Netherlands, specialized in business, management, finance and media. He works for Alex van Groningen, a community business, at the moment active in The Netherlands and South Africa, that is committed to bringing CFO’s and finance professionals together.  

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