At a session from our 2022 IT Sales And Marketing Boot Camp, I had the chance to sit down with Sammy “The Bull” Gravano, one of the most infamous figures in organized crime. This conversation provided a rare insight into the inner workings of the Mafia, leadership structures and the brutal realities of loyalty and betrayal. While the world of organized crime is vastly different from running a legitimate MSP business, there are universal lessons about leadership, power dynamics and decision-making that are worth paying attention to.
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From Gang Life To The Mafia
Sammy’s journey into organized crime started young. He described himself as a troubled student, struggling with dyslexia at a time when learning disabilities were misunderstood. After being held back multiple times in school and getting into violent altercations, he found himself drawn to street gangs, specifically the Rampers gang in his neighborhood.
Despite knowing about the Mafia, Sammy and his peers initially stayed away from it. But that changed when he was approached by a Colombo family member who offered him a choice—join them and have protection or continue as a lone wolf, which meant certain death in their world. At just 23, Sammy made the decision that would shape the rest of his life.
Entering The Colombo Family And His First Hit
When Sammy joined the Colombo crime family, he quickly learned that the Mafia wasn’t just about power—it was about loyalty, structured operations and following orders. One of his first experiences in organized crime was being told to “hit the mattresses”, a term that meant going into an all-out war against a rival faction.
His first murder assignment came after a man named Joseph Colucci plotted to kill him and his associates. When the higher-ups caught wind of the plan, they ordered Sammy to carry out the hit. This was his initiation into the darker side of the Mafia, where power struggles were settled permanently.
Moving Up: Transferring To The Gambino Family
After internal conflicts in the Colombo family, Sammy was transferred to the Gambino family—one of the most powerful and business-focused factions of the Mafia. He described the difference between the two families:
- The Colombo family was more reckless, often resorting to violence immediately.
- The Gambino family, on the other hand, operated like a business—violence was a last resort, and they were heavily involved in construction, unions and financial operations.
This transition taught him the importance of strategic thinking, calculated decision-making and the power of operating a criminal empire like a business—all lessons that apply in the world of legitimate entrepreneurship.
Involvement In The Castellano Hit And A Reputation For Violence
One of the most notorious moments in Sammy’s career was his involvement in the assassination of Paul Castellano, then-boss of the Gambino family. He admitted to being involved in 19 murders, although not all were carried out by his own hands.
In the Mafia, involvement in any murder—whether planning, giving the order or pulling the trigger—meant equal accountability. This echoes the reality of leadership in business: you are responsible for the decisions you make, whether directly or indirectly.
The Code Of Loyalty And Eventual Betrayal
Sammy spoke extensively about the Mafia’s code of loyalty, which was ingrained into every member through blood oaths and unbreakable rules. The Mafia came before family, country and even God. If you were summoned, you had to drop everything and show up—no exceptions.
But despite this unwavering loyalty, he was eventually betrayed by John Gotti, the very man he helped take power. Facing a life sentence, Sammy made the shocking decision to cooperate with the government, providing testimony that led to Gotti’s conviction.
For business owners, there’s a stark lesson here: loyalty is important, but blind loyalty can be dangerous. Align yourself with people who uphold the same values, but always protect your own interests.
Life After The Mafia: Business And Media
After serving 22 years in prison, Sammy re-entered the world with a different approach. He started a podcast and social media presence, openly talking about his past in a way that had never been done before. Hollywood producers have even approached him about turning his story into a TV series, similar to The Sopranos but more grounded in reality.
He claims that above all, he is now obsessed with telling the truth. His stories cover the good, the bad and the ugly of his life in organized crime—no sugarcoating.
Final Thoughts: Lessons From A Life Of Crime
While Sammy’s world was brutal and unforgiving, his story highlights some key lessons that can apply to MSP owners and business leaders:
- Power Is Nothing Without Strategy – The Gambino family operated like a business, proving that success isn’t just about brute force but about long-term strategy.
- Loyalty Has Limits – Choosing the wrong people to trust can be fatal, whether in crime or business.
- Reinvention Is Possible – Despite his past, Sammy has managed to adapt and carve out a new path in media and storytelling.
At the end of the day, this conversation was an eye-opening look into a world few will ever experience firsthand. The Mafia may be a world away from running an MSP, but the principles of leadership, decision-making and survival remain universal.
