The Art of Strategy and Reinvention

There is not as much of a difference between illegal businesses and legal ones as you may think. For example, running a drug dealing operation involves sales, customer service, and accounting skills. Leading a gang requires people management, communication, and adaptability. These are all commonplace in a well-running Fortune 500 corporation too. At the core of this is the importance of recognizing transferrable skills, one foundational element of the work I do in helping formerly incarcerated individuals build businesses. Just because someone may have run an illegitimate hustle, it doesn't mean they don't have the ability to do so legitimately, actually quite the contrary.

This worldview has become a no-brainer for me in the more than two years I've spent doing this work. And while it may not be something that most people have thought of or come to terms with, we all have something to learn from it. The secret to this lies in strategy, and how someone goes about applying their skills at the right time. One of the greatest examples I've seen of this is in Robert Greene's book The 50th Law. Greene, one of my favorite authors, wrote this as a follow up years after his classic, The 48 Laws of Power, and focused it around the life of Curtis "50 Cent" Jackson.

Fifty grew up in Southside Queens at a time when crack had ravaged the community. His mother, who had him at age 15, turned to drug dealing to support their family. She tragically died 8 years later in a house fire that was likely started by a rival drug dealer. This experience hardened Fifty at a young age and showed him the cruel world that he was placed in, thus leading to drug dealing himself in order to survive. In 1994, after getting arrested for selling and possessing drugs and subsequently sentenced to a "correctional" boot camp program, Fifty turned to music as a release.

While it took Fifty several years to transition away from his drug dealing business, he poured much of his time into writing lyrics and rapping over beats. His unique flow and work ethic were quickly noticed in the hip hop industry. He signed to Columbia Records, was asked by Nas to perform on his tour, and had songs that caught the attention of Jay-Z, DMX, and Wu-Tang Clan. Just as Fifty was on track for mainstream commercial success in the year 2000, a hired gunman shot Fifty 9 times in a car outside his grandmother's house. This made Fifty toxic, a man surrounded by so much violence that no executive would want to risk doing business with him. The bullets alone should've killed him never mind his music being shelved, but instead of dwelling in pain and negativity, he used his recovery time to hole up and plan his comeback. Fifty came up with a unique idea for a relentless and organic mixtape campaign intentionally using bootleggers to flood the streets with his music. It caught the ear of Eminem...the rest is history.

Fifty's accomplishments speak for themselves: Over 30 million album sales, hit TV shows, movies, bestselling books, an endorsement deal with Reebok, a massively lucrative Vitamin Water partnership, a headphones company, a lucrative stake in a vodka company, a Super Bowl performance, and the list goes on. But what makes his career so fascinating and impressive is his use of transferrable skills and strategy to achieve success in these categories.

He acknowledges that he learned much of his business knowledge from the streets. When you're hustling on the corner, your life is on the line and you need to be cunning. You need to develop a sixth sense of when things might go wrong. You need to think about marketing strategies, branding, and product development to stay a step ahead when all of the rival dealers are trying to gain a monopoly and take control of your turf. Yet while the environment of Southside Queens was a dangerous place, Fifty said that the corporate boardrooms he'd previously done business in were just as tough, if not worse. Many executives, especially in the music industry, were manipulators, self-servers, and power wielders who would do anything to get one over on you and say one thing to your face just to stab you in the back.

Fifty has gone through several stages of character development as a mechanism to counteract this cutthroat culture. First, he found a way to use his tough guy, unpredictable image to his advantage, becoming one of the kings of early 2000s rap. He then cultivated a savvy entrepreneurial toned-down persona that was more "brand-friendly" for sponsorships with big businesses. He has played the role of social media provocateur, intentionally drumming up controversy, when looking to promote and get "free" attention for his projects. And once his core fan base grew older and was no longer as interested in the kind of music Fifty used to make (a style that would also be tough to keep up with in his 40s), he pivoted to be a TV production mogul that met his audience where they were. Fifty reinvented himself at every turn and continues to do so.

This all begs the question, how much of this is by design versus Fifty being a natural genius? I think he would tell you it's more of the former. But, for our practical purposes, it doesn't really matter. What we can learn is that the art of strategy, transferrable skills, and reinvention are all tools within our toolbelt. Best believe, we should make use of them. We don't need to have grown up in Southside Queens in the crack era or have done the things Fifty did as a youth to take cues from his success.

We live in a time of economic downturn where major tech companies went from doling out cushy salaries and perks to laying off thousands of people. A major financial institution, Silicon Valley Bank, just instantaneously crashed causing a major ripple effect in the markets. Artificial Intelligence is advancing so rapidly that jobs are more at risk than ever. There is extreme volatility right now, no one can know exactly what's around the corner. The only certainty is uncertainty. We are in our own version of Southside Queens.

This calls for us to be antifragile, to use the term coined by Nassim Nicholas Taleb. We need to be comfortable being uncomfortable, assume formlessness (Law 48), and see how we can gain from, not just succumb to the conditions we live in. Think several steps ahead like a grandmaster chess player or like someone in Fifty's position. We have better odds of success than he did based on where many of us grew up. But what we lack is strategy and the will to reinvent ourselves. Playing it ultra safe feels too good. Change is extremely painful, especially for those of us who haven't had to persevere through such hardships. We need to build up resiliency and train it like a muscle. We need to be fearless.

The point is that now is not a time to be complacent. Think about the skills you have and if you're maximizing the potential of what those have to offer. Are you being strategic with how you take initiative of your career or are you letting life happen to you? How are you reinventing yourself to meet the changing needs and demands of the business world, not of today, but of 2024 and beyond? These are the questions we should all be asking ourselves. None of us want to wake up tomorrow and realize that it's too late.