During the interview, Sway asked Ryan, “When the last time you been broke?… When did you hit bottom?… Last time you hit bottom”, and Ryan responded:
Man, uh, right after college, man. Right after college… Uh, you know, and it was crazy too because I hit the rock bottom after my boy got signed so…
My boy, Corey Latif Williams, he had gotten signed, uh, with Hock Islam, uh, and Kedar Massenburg, we went to Chicago recording studio, we did the album, and then there was, as usual, there were delays in the release of the album.
And, you know, I got paid as a producer, maybe $10,000 a track. That was the most money I’d ever seen from music, maybe somewhere between four and seven tracks.
And I thought it was great, and then I realized man that’s no money, and I ended up, basically, homeless in a, you know, in a garage behind a barber shop in Randolph, Massachusetts, man.
…In a garage, used to be homeless behind a barber shop. Like, literally, you know, walking across the street to eat, you know, shoplifting crackers, you know what I’m saying?… A Harvard grad.
…And, uh, ended up on my father’s couch. And, uh, my dad, basically, said, ‘Wow, you know, we worked our whole lives to get you into an Ivy League school so you would be straight…’ And, you know, they also worked their whole lives as a Salvation Army officers, which meant that they sacrificed, you know, financial gain here for what we would call Treasures in Heaven by actually, you know, serving other people.
So they really looked at me as, ‘Hey, when we get to that age… we sent you to Harvard so you could take care of us.’
And, obviously, I’m able to do that now, but at that time my father was getting a little apprehensive.
But, he made a deal with me… Um, he said, ‘Look Rye, you know, if we’re not gonna believe in you, who is? What is it that you need?’
And, I said, ‘Look I need, you know, this keyboard. I need this computer. I need this software.’
And he maxed out a credit card that he got in the mail, and he made a deal with me.
He said, ‘Look, imma max out this credit card, and you gotta make me a deal that, uh, you know, uh, you pay me back double within five years, but there’s an insurance plan for that five years.
You have a year to try in figure out how you’re going to make it in music, and if you don’t then you gotta apply to law school. And law school is three years so when you get out of law school you should, after you actually are gainfully employed, you should be able to give me back double.’
Uh, fortunately for me in any great story serendipity plays a piece, and the late great Ed Woods actually called me up maybe about four months after I got all my equipment, and he said, ‘Yo man, I got an internship for you in New York City. It’s unpaid, it’s 30 days, but, you know, come on out here and let’s see what you could do.
And, man, um, that was 2003, the rest was history.
Ryan Leslie is far beyond broke these days. Earlier in the interview he stated that he has amassed enough wealth that he doesn’t have to work another day in his life.
Ryan has also created a Wealth Plan, a financial literacy and wealth-building program that supports everyday people in establishing a path to financial freedom by educating and empowering them through coaching and mentorship from the knowledge he has learned from years in the finance world.