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Interview: Kwame Jackson – Real Estate Entrepreneur and Professional Speaker (of Apprentice Fame)

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This article is part of a series in celebration of a new, dynamic voice in Black America: the NUBIANO Exchange. Brace yourself for the NUBIANO experience.

by Clayton Perry

Kwame Jackson is best known for the business savvy he demonstrated on the first season of Donald Trump's Apprentice. Although several years have passed since his “boardroom” experience, Jackson has successfully capitalized on his entrepreneurial skills and newfound celebrity. In April 2004, he co-founded Legacy Holdings LLC, a private investment firm with diverse interests, including real estate development, fashion, television and film production. Concurrently, following his Apprentice experience, Jackson’s expertise allowed him to blossom into an in-demand speaker and advisor for Fortune 500 firms and universities, as well as community, civic, and political leaders. To date, he has given over 250 lectures. Squeezing some time out of his busy schedule, Kwame Jackson settled down for an interview with Clayton Perry, reflecting on life, the Apprentice experience and race in America.

After going through the Apprentice experience, what have you learned about yourself? How has your life changed?

I’ve learned to have confidence in myself, better utilize my skills, and make opportunities for myself. I have also learned how to discern what’s important to me and what’s not. In life, I want to make a difference. Sure, I want to make a little bit of money and have some fun. With time, however, I found that money is not as important as I once though it was. I’ve also found great value in owning my own time. Moreover, I have also learned not to judge myself by other people’s yardsticks. It took time for me to realize that dollar signs behind it are not reflective of the passion behind. I made a conscious decision to step away from Wall Street. In the grand scheme of things, it’s not that important.

As opposed to other Apprentice alumni, why do you think you were better able to maximize your experience in the way you have? How did you do it?


One key difference is my mentality. Looking at reality TV, as a whole, you have your Chances and Tangos, and your New Yorks and Flavors and, then, you have me on the other side. When you look at reality TV, as a vehicle towards any new platform or springboard towards something positive, you have to frame your reality for yourself. On the Apprentice, I framed myself and didn’t get caught up in controversy. I always had my dignity and respect — something that’s hard to come by in celebrity culture. Losing either was not a trade-off that I was willing to make. Some people on the Apprentice were just happy to be on TV and, as a result, their experience led to negative depictions and limited opportunities — forever! Things were not just handed down to us. All of a sudden, you have 40 million people watching you. What are you going to do with that? What kind of opportunities are you going to create? For me, life on the Apprentice experience was a journey, although it was not a blueprint for success.

You are often quoted saying, “We have our whole lives to be ordinary, and only a few fleeting moments to be extraordinary!” What life event served as the turning point (or tipping point) — leading you away from failure and toward success?

I don’t think one ever gets led away from failure. Once you’ve been successful for so long, it becomes really easy to get comfortable and unwilling to go against something against which you could fail. Success is nothing but a string of failures. Nothing ventured nothing gained. I’m comfortable with that. In order to be successful in life, one has to take risks. And I know, from personal experience, that you have got to fall on your face a couple of times before you can get up. My “turning point” came about when I began to recognize my potential and realize the fact that I had the skills, confidence and, now, national notoriety to create and capitalize on personal success. I’m not yet where I want to be, but I’m going to get there.

Reflecting on your early years, what events led you to think: "This is what I want to do – be a businessman"?

I don’t think it was ever that clear. In life, all people can do is prepare themselves for opportunity. All one needs to do is have an open mind, so that they can recognize it, and, then, go after it. I never said one day that I was going to work to become a businessman. I simply told myself to venture out, get an education, obtain an advanced degree, work at some good companies and see where life takes me. When I put my life in motion, opportunities presented themselves.

How do you define yourself?

I don’t. My life’s guiding principles, along with my faith and spiritual relationship with God, keeps me grounded. Because of my success and my attendance at Harvard and the University of North Carolina, people often tell me that I should do this or do that. How is someone else going to tell me what I should do to be happy? I’m already focused on that for myself. Too often, people waste so much energy trying to live other people’s
lives — trying too hard to be different, make money and lavish in fun. I just try to focus on my own passions and continue by the choice I made to be on a very different path. 

What are some of your favorite quotations? What meaning/significance do they have for you? (Were they inspired by a role model, life event, etc.?)

Martin Luther King, Jr. once said that "[t]he ultimate measure of a man is not where he stands in moments of comfort and convenience but where he stands at times of challenge and controversy." That quote resonates deeply with me. Everyone can get along when it’s easy to get along, when bills are paid and everyone’s smiling. But look how quickly things change when people have to make difficult, unpopular choices?

Another powerful quote that I like comes from Barack Obama, when he delivered his keynote address at the 2004 Democratic National Convention: “Go into any inner city neighborhood, and folks will tell you that government alone can’t teach our kids to learn; they know that parents have to teach, that children can’t achieve unless we raise their expectations and turn off the television sets and eradicate the slander that says a black youth with a book is acting white. They know those things… people don't expect government to solve all their problems. But they sense, deep in their bones, that with just a slight change in priorities, we can make sure that every child in America has a decent shot at life, and that the doors of opportunity remain open to all… they know we can do better. And they want that choice.”

When we keep that in mind, that achievement and success is acting white, then please tell me what acting black is? Is that what we should aspire to? All of America should re-evaluate these things.

I also like Jack Johnson’s mantra: “You don’t define me, I define me.” One should always stay true to oneself and one’s own priorities. In addition, they should also be able to live up to any related consequences.

Another quotation that I love comes from Robert Johnson. He once said that individuals should “make [their] friends before [they] need them.” People should harness that inner power to accomplish things. In the end, it’s funny to see how things always tend to work out.

What is your perspective of race in America?

Unfortunately, we are not very far from the turn-of-the-century question posed by W.E.B. DuBois. Even in the 21st century, much of American life is defined by the color line. In regard to race, America has such an ugly and deeply entrenched culture. It’s almost like the 800-pound gorilla in the room. Most certainly, we have made some progress. Without question, I can do more things that W.E.B. DuBois could in his day. Until we start to move past some things, however, there is a lot of progress left to be made. That being said, America is supposed to be a meritocracy. If someone has good ideas and works hard, race is a small hurdle. Granted, some energy will be needed to overcome it, but it is false to say that it cannot be overcome. Make no mistakes, though, it is there. One only has to look at the large educational disparities, disproportionately high incarceration rates and limited economic opportunities to see that. I do, however, firmly believe that if one never gives up, one day they will succeed.

What specific instance crystallized your conception of race?

It must be noted that I didn’t grow up in the civil rights movement or have people shouting “nigger” in my face; living in North Carolina, however, my own people tried to instill the notion that if you’re trying to be accomplished, then you were trying to be white or labeled an “Uncle Tom.” That’s when thing began to crystallize. I came to see how deeply scarred we are as a people and what that means, as it pulls us back into mediocrity instead of pushing us up to greater heights. “You’re so ashy … so dark … African booty-scratcher.” It’s crazy that it’s so deep and entrenched in us. I’ve been a victim of it and even used it. It’s on a very subconscious level. Look at how beauty is defined in America and everything that you see in Hollywood. It’s not surprising that minority groups internalize that. The possibilities and limitations on one’s own (or cultural) success is stamped on your brain a million times before you hit the sixth grade. By the time a child grows up, especially without proper care, it takes a lot of strength for someone to erase all of that from his or her memory bank and turn it down.

If you could change one thing in the black community, what would it be?

I really wish that when African-Americans were freed, circa 1865, we would have been given full economic and civic participation in society. Imagine what 40 acres and mule would be worth. Imagine the culture of entrepreneurship, had we not been locked out of the political arena for so long or being suffered the second-class citizenship of race and economics. Money talks and green is the ultimate force in our culture. Out of 35 million African-Americans, we only have two billionaires: Oprah [Winfrey] and Bob [Johnson]. (This point shows that we are just now getting to participate at the highest levels of society.) America is a capitalist society and people don’t have to help you. Economic empowerment is the source of real power. People have to help themselves.

If you could meet any black pioneer, for a day, who would you select? Why? What would you talk about? What questions would you ask?

Malcolm X. At the end of his life, he was changing. I’m interested to know the internal struggles he was going through and the strategies he would have tried to implement (had he not been assassinated). I always admired him. He had a fascinating air about him. He was always was depicted as a counter against Martin, as a separatist, since he wasn’t always supportive of non-violence. But if someone harms your family, what would you do?

If you had to live your life over again, what one thing would you change?

I don’t live my life in “would-as", “should-as" and “could-as". When I was a kid, I sold candy on my bus. There’s no denying: I was going to be an entrepreneur, even though I didn’t grow up saying I wanted to be on Wall Street. That’s what I am and that’s what I’ll be. If I had to look back, I probably would take a shot a being a stand-up comedian. Chris Rock and Richard Prior had the best sense of humor and they cut up a lot — hamming it up in front of people. That may be an alternate career path at some point. I have a weird sense of adventure and I like testing myself. I thought about becoming a Navy Seal and going through that process, so that I could push myself to limits I never thought possible. I don’t think either one of those are going to happen though.

What is the legacy that you would like to leave behind?

If people can look at my life and say, “Kwame Jackson inspired the second generation of the civil rights focus on wealth creation and economic empowerment,” I would be pleased. It is high time that we wake our generation up, take ourselves out of the bling culture and start focusing on owning a home, instead of trying to dunk a basketball and make a CD. I definitely don’t want my legacy to be a bunch of zeroes behind my name but, rather, a legacy of influence, positive images, and idea creation. Hopefully, it’ll snowball. Maybe I’ll have my Barack moment and feel really good. I’m a capitalist and I like nice things, but they don’t define me or drive me.

Your website notes that you have a book in the pipeline. What can fans expect?

This project has been a long haul for me. Currently, I’m working with a literary agent and debating over different ideas. Readers should expect to find personal revelations on the notion of persistence, overcoming "nos" and how to turn a “no” into a “yes.” They will also find information on what people have done since the beginning of the word “no.” A pastor of a close friend once said that the “setback ain’t nothing but the setup for the comeback.”

For more information about Kwame Jackson, please visit his official website.

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About Clayton Perry

  • http://www.KappaAlphaPsi1911.com Spencer Bruce

    Great article on Brother Kwame Jackson. He has a good story to tell on work ethics, persistency, lessons learned and achievements and his book should be very intersting reading.

    Deputy Executive Director
    Kappa Alpha Psi Fraternity, Inc.