Come Fly with MeUltimate Jordan, and Airtime--I saw and studied all of the Michael Jordan videos as a kid. Who didn’t? Never in a million years could I have imagined I would join MJ’s circle of advisers when I grew up, but life is full of surprises.

In March of 2007, I received the opportunity of a lifetime to work in the NBA for the then Charlotte Bobcats, now Charlotte Hornets. Michael was minority owner and president of basketball operations at the time, and I was asked to be the organization’s director of legal affairs. In addition to traditional legal responsibilities, I was also asked to play a role in the organization’s management of its salary cap and player transactions. This latter role thrust me into a crucial part of what the organization did, and helped me learn what Michael needed from his business “teammates.”

Within a few years, I was asked to lead the organization’s legal department as its vice president of legal affairs, which increased the frequency of my interactions with Michael and gave me the unique opportunity to observe, study, and internalize lessons from the man many (including me) believe to be the “G.O.A.T.” (Greatest of All Time). When you are around Michael enough, you realize very quickly that his rise to the top was far from coincidental. I observed his leadership style, his quick mind, and his pure desire to be the best.

Today, I’m the founder and CEO of Yuno, a social shopping startup changing the way we think about our value in commerce. So why leave what many would consider a dream job? Because, like Michael, I’ve always wanted to put my abilities to the test and I’ve always had the desire to be the best. In July 2013, I decided to pursue my entrepreneurial dream. And what I took with me were five important lessons from Michael’s journey that everyone, especially entrepreneurs, can use to achieve their goals.

1. You Must Experience Failure to Achieve Success 

MJ missed more than 9,000 shots, including 26 game winners. He didn’t make his high school’s varsity basketball team the first go-around. He kept losing to the Pistons early in his career. He’s dealt with negative comments about being an owner of the Charlotte Hornets. Still, he learns (and thrives) from failure and has never once backed down from the biggest challenges. 

Takeaway: You’ve got to embrace failure to find success. From there, success fuels more success for yourself and those around you. Once you figure out how to win, the culture of winning becomes ingrained as second nature.

2. Build an All-Star Team

While he is remembered for leading the greatest team in NBA history, it took years to find the right kind of help to get him to the top. While history still sees him as "the guy," it took years of adding the right pieces around him to build the ultimate culture and formula. 

Takeaway: Being the smartest, most gifted person in the room only gets you so far when the odds are stacked against you. You’ve got to surround yourself with other valuable talent and role players who are willing to sacrifice individual accolades for the greater good. The opportunity to be on a team that’s going in the right direction will help you inspire and attract top talent.

3. Work Smarter--and Way Harder--Than Your Competitors

Michael was--and still is--driven by the desire to be the best. But he realized from an early age that his talents alone wouldn’t carry him to the top. He had to add size, maturity, strategy, and new skills in order to take down the many other hurdles standing in his way.

Takeaway: Be honest with yourself and understand what your weaknesses and strengths truly are, both as an individual and a leader. Should you do the same analysis of your competitors, you’ll find that you possess many dangerous weapons that they have no defense for.

4. Believe Without a Doubt That You Are the Best

With legends such as Larry Bird and Magic Johnson carrying the NBA torch through the 1980s and early '90s, Michael knew exactly who was on top of NBA’s Mount Rushmore. Even before he had a single championship to his name, he knew the future was his for the taking. And once that thought was in his head, nobody was going to stop him, the haters included.

Takeaway: To be the best, you have to first conceptualize it. Just like you would fantasize about hitting the game-winning shot in your own driveway as a kid, it’s vital that you visualize the thrill of victory--that you see that your company can be the true leader in your industry. When you know what success looks like, you can take every necessary step to make it a reality. Just be sure not to mistake cockiness for confidence.

5. Build Something That Leaves a Legacy

Nearly 15 years after retiring from a legendary career, MJ is still remembered as the G.O.A.T. Not only did he help transform a sport and inspire an entire generation, his contributions spanned the globe and transcended far beyond the hardwood. As a businessman, his clothing brand remains iconic, and he remains active in a number of endeavors that enhance the lives of millions.

Takeaway: As an entrepreneur, you’re only hardwired to think about today and tomorrow, not 10 or 50 years from now. That focus is critical to remaining on course with your main objectives. However, you need to take some time to look at the longer-term vision for your business or cause. How will it thrive long after you give up your position at the helm? Are you building something for your children, your community, or even complete strangers to benefit from? The answers to those questions can be far more rewarding than the fruits of your labor today.

Published on: Aug 21, 2015
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