The People I Looked Up To In Business (And Why That Might Surprise You)

Growing up, I found myself studying an unlikely group of "business leaders" – characters from movies like Goodfellas, The Godfather, and Scarface, alongside some real people from my neighborhood who happened to be in the drug trade. Before you close this email, hear me out. I'm not talking about glorifying violence or illegal activity. I'm talking about something much more nuanced: the art of understanding what people really want and creating mutually beneficial relationships to achieve goals. The core insight was simple but powerful: if I help them get what they truly want, they'll naturally want to deliver something valuable to me in return, and we can both win together.

There's a scene in Goodfellas around the Lufthansa Heist where the crew pays off truckers to tip them about valuable deliveries. What struck me wasn't the crime – it was the psychology. They understood that everyone has needs, motivations, and pressure points. The truckers needed extra money. The crew needed information. Instead of demanding or threatening, they created a system where both parties won.

I saw this same principle play out in real life growing up. The guys in my neighborhood who ran successful operations weren't the flashy ones or the ones who used intimidation. They were the ones who understood their community. They knew the owner of the local bodega, they knew the coach of the high school football team, they knew the local mechanics who fixed all the cars. We were all one community, and even though they were criminals and didn't operate above the fold, they contributed positively to the community and the community in turn respected them.

This taught me something most business books miss: success isn't about being the smartest person in the room – it's about understanding the wants and needs of everyone else in the room.

We're constantly told to look up to successful CEOs and entrepreneurs. But here's the problem: just because someone is successful doesn't mean their path is worth emulating. Some got there through luck, inheritance, or by stepping on others. Some built empires on foundations you wouldn't want to touch.

The characters I studied (fictional as they were) and the real people I observed had one thing I rarely see in traditional business heroes: they were obsessed with understanding human nature and creating genuine value exchanges. They knew that sustainable power comes from making yourself indispensable to others, not from taking advantage of them.

Whether it was Henry Hill in Goodfellas understanding how to make the right connections, or watching someone from my neighborhood who knew every person's story, their kids' names, their struggles, and exactly how to help when needed – they all understood that business is fundamentally about relationships and solving problems.

What fascinated me wasn't the illegal activity – it was how these characters and real people approached relationships. They asked themselves:

Compare this to how many people approach business today. They network by asking for favors without offering value. They expect loyalty without earning it. They want partnerships without understanding what the other party truly gains.

I want to be crystal clear: I learned about strategy and human psychology from these characters, but I learned right and wrong from family, mentors, and life experience. The goal was never to emulate their actions – it was to understand their approach to reading people and creating win-win scenarios.

In legitimate business, this translates to:

These unconventional lessons fundamentally changed how I approach every business relationship. Instead of leading with what I need or want, I ask people "What's keeping you up at night?" I look for ways to understand them and secondly understand their problems.

The results have been remarkable. When clients feel truly understood and see that I'm invested in their success, they become advocates rather than just customers. When partners see that I'm genuinely looking out for their interests, they go above and beyond what any contract could require. When employees feel that I understand their personal goals and help them achieve those alongside business objectives, they deliver work that exceeds expectations.

This approach has led to stronger partnerships, more loyal clients, and team members who genuinely care about our shared success. The relationships last longer, the deals are better, and the trust runs deeper because everyone involved feels genuinely valued and understood.

I realize this isn't the typical "look up to Steve Jobs" story. But I think we need more honest conversations about where we actually learn business lessons. Sometimes wisdom comes from unexpected places – including fictional characters whose moral compass was completely broken but whose understanding of human motivation was razor-sharp.

The key is separating the lesson from the messenger. You can study strategy without adopting values. You can learn about human nature without losing your humanity.

Maybe it's time we stopped pretending all our business insights come from Harvard Business Review and started acknowledging the complex, sometimes uncomfortable places where we actually learned to read people and understand what makes deals work.

What do you think? Have you ever learned valuable business lessons from unlikely sources? Hit reply and let me know – I read every response.