Entrepreneurship Lessons from HBO’s The Sopranos

Like any second semester senior with a job locked up, I finally had the time to begin watching a new TV series. As a huge HBO buff (It’s not TV, it’s HBO), I landed on the famed, critically acclaimed series of the early 2000s, The Sopranos. Little did I know that this show would touch upon many entrepreneurial lessons I have learned both in the classroom and while working on my own ventures.

We can go back and forth for days debating whether the show’s main character, Mafia Boss Tony Soprano, is a hero or villain. However, what everyone can agree upon is that Tony is a true entrepreneur. Although his tactics for success certainly differ than other entrepreneurs we know (Could you imagine Zuckerberg in the mob?), the end result is the same: Tony runs his own group of businesses.

Here are three critical lessons from the one and only Anthony Soprano:

1. Cash Flow Businesses are King — So far (three seasons left) Tony does extremely well financially, because, unlike many entrepreneurs today who seek users first and revenue later, he has positive cash flow from small businesses in a diverse range of industries. He has ownership stakes in a gentlemen’s club, bootlegging business, pizza restaurant, and even a local spa. All of these businesses are what I call asset sale companies, meaning he does not have to raise millions of dollars to finance each project with the expectation of generating revenue. Other than the upfront (one-time costs), these businesses generate straight cash for Tony and his crew. Needless to say, a few of these businesses do border on legality, but it should not dilute the key lesson here: start businesses that generate cash RIGHT AWAY. Without cash, you can’t sustain your business. With debt, you are at the constant mercy and susceptibility of your investors.

2. Be a Strong Leader — By this point in the show, Tony is the bonafide Boss of his Mafia gang. With close to 50 people serving under Tony through the Mafia and his businesses, Tony needs to rule with an iron fist, but also motivate his employees. I am here to state emphatically that Tony leads by example, both in commerce and crime. When his own soldier Christopher was shot, Tony took matters into his own hands for vengeance, almost unthinkable for a boss of his pedigree. In business, Tony has exemplified his negotiation skills, savvy for new opportunities, and ability to transcend the minds of his employees. Tony’s handling of his aloof, erratic nephew Christopher best shows his leadership skills. When Christopher missed his son’s communion, he grabbed Christopher and told him he needs to make a decision in 15 minutes whether he is with Tony for good. Like most entrepreneurs, Tony wants employees who are putting their heart and soul into the company. He has no time for wishy-washy dedication; entrepreneurs need to follow Tony’s paragon and take control of situations. Beating around the bush with your employees never reaps positive benefits, especially as an entrepreneur.

3. Network constantly — It is no secret that entrepreneurs need to network and connect with other like-minded individuals as often as possible. You never know when a connection will come in handy for your business. Most outside venture funding is a direct result of a personal connection with someone at the firm. Tony Soprano is an extremely adroit networker, and certainly lives & breathes one of my favorite networking principles: it’s not who you know, but who knows you. The best example to date is when Tony ventured over to Italy to visit another organized crime faction for a potential business deal. Tony practiced the art of networking so well in fact, that he even attracted the love interest of Annalisa, head of the Neapolitan family. The trip culminated with an unexpected prize, the allegiance of a new solider, Furia Giunta. There are always opportunities for entrepreneurs to help each other, even in ways unintended in the first place. Let’s say you are a businessperson and you network with a coder to attract his/her talent for your latest mobile application. Without asking, you may never know when that coder will also have Angel Investor connections for you…

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