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.”