Turn Every Page: Entrepreneurship

“[Don’t] let anyone convince you that your dream, your vision to be an entrepreneur, is something that you shouldn’t do. What often happens is that people who are well meaning, who really care for us, are afraid for us and talk us out of it.”

-Cathy Hughes, entrepreneur and business executive

Do you know who Curtis Jackson is? If I ask most of my friends, I will get a blank stare. Some of you who receive this newsletter have already stopped to Google the answer. If I ask friends who 50 Cent is, they’ll have an answer—“he’s a rapper,” perhaps—but they will not know that 50 Cent and Curtis Jackson are the same person. Nor will they know that Curtis Jackson is much more than a rapper.

Recently, I finished Jackson’s Hustle Harder, Hustle Smarter, in which he chronicles how he gave up a life of drugs and rap music in favor of entrepreneurial endeavors—television, movies, and other business investments. Curtis Jackson already had a platform, so some would say it was easy for him to start a business compared to others. He was not subject to the same percentage of risk that others may experience—and, of course, he had millions of dollars to ease his fall if a particular business venture didn’t work out.

That all may be true, but Hustle Harder, Hustle Smarter explains how even with some advantages over others, starting and building a successful business is still tremendously difficult. But there are some enduring principles from Jackson’s experience that we can apply to ourselves or entrepreneurs who are looking for their next opportunity.

For example, Jackson talks a bit about only investing in sure things. There is obviously never a “sure” thing in the sense that there is always some risk, but Jackson has learned to significantly temper the risk of any deal or long-term endeavor so that the end result will almost certainly be in his favor. Essentially, Jackson does his homework and does not invest in another person or business unless he knows it has a high likelihood to succeed.

Another take-away is that you need to choose your partners and employees wisely. Jackson was repeatedly asked for favors and to give other people opportunities. When he did, those people would not always meet expectations. Some thought that because they hung around with 50 Cent, they were entitled to some share of the money and benefits he was receiving. After a while, he had to cut these free riders loose to remove the dead weight and the people that did not actually have his best interests in mind.

One theme in Jackson’s book is to look at things differently and to take bold action based on your unique perspective. When Jackson saw an opportunity to invest in Vitamin Water, he took it. He was attracted to the product, and even though it was an unlikely move for a rapper—most rappers were endorsing alcohol of some sort—he gave valuable insight to the company about expanding their market share and improving their product. He brought a perspective that no one else did, and he exploited it to great effect.

The same thing happened when he started the television series Power for the STARZ Network. After other networks passed on the show, Jackson was willing to accept what amounted to a pittance for him—$17,000 per episode—because he believed in the show and the concept. As he describes in the book, 50 Cent could make multiples of that amount on a single night performing at a club. But Jackson’s initial concession on compensation not only led to a $150 million deal over four years, it also solidified Jackson’s place in cable television and marked his shift from music to other media. (STARZ benefitted quite a bit as well, going from a no-name cable network to a viable player in the market.)

Curtis Jackson’s story of going from street hustler, drug dealer, and famous rapper to entrepreneur and business owner is a fascinating journey. Other books on entrepreneurship are not so raw. A lot of business books are ghostwritten pseudo-biographies meant to portray a business owner in the best light possible. Other books by prolific authors still often fail to explain the real struggle of entrepreneurship. Walter Isaacson’s Steve Jobs is a good read, for example, but I don’t think it tells the full story. Jobs is portrayed as a kind of madman, eccentric visionary and we certainly see his flaws in dealing with other people and his lack of bedside manner as a chief executive. But in the end, Isaacson’s book left me wondering about the personal human struggles Jobs had along the way. What did he struggle with internally beyond a quest for beautiful and intuitive products? What made him cutthroat and condescending? Did he see that as the only way to succeed in his line of business? Jackson offers a very human story that is surprisingly relatable even for people who did not grow up in Queens. (Another book to read in this genre is Arnold Schwarzenegger’s Total Recall: My Unbelievably True Life Story, his autobiography. Arnold is the master of diversification in that he participated in more types of endeavors—fitness, physical labor, real estate, business ownership, movies, politics, philanthropy—than most others, and he did them all with success.)

Starting a business is difficult. I did not set out from law school to start my own law firm, but it has been one of the greatest blessings for me. My oldest daughter spent years participating in a business fair here in Phoenix and is now trying to start an Etsy business. She’s experiencing just how difficult it can be. Other people I know have good (or sometimes great) business ideas that die on the vine because the person is too scared of failure.

I heard a podcast recently where a guest from a foreign country said that failure is part of what made America great. We have historically not condemned failure in the way that other countries and cultures do. Thomas Edison made more than 10,000 attempts to create a lightbulb and no one thought he was a madman. As he apparently said, “I have not failed. I’ve just found 10,000 ways that won’t work.” No one remembers Edison for his many failures. But no one would remember him for anything if he had been too scared to attempt his first experiment.

Entrepreneurship takes courage and endurance, and those are two things in short supply these days. In the era of quiet quitting and lazy remote work, I wonder whether children and young people will have the virtue of entrepreneurship instilled in them. I’m glad my daughter is trying to start a business. I hope she stays at it. Any experience running a business—from a lemonade stand to a multi-million dollar company—is worth having.

Without taking some risk, there is no reward. Whether it is in the context of your career or whether you think you have the next great business idea, take the calculated risk. It may not pay off financially, but you will become more human in the process.

Remember to turn every page. Enjoy your weekend. Please let me know whether you need anything.

Best,

Aaron