A white artist, he works in a genre largely known for its black musicians. He has collaborated with Kenneth "Babyface" Edmonds and the late Tupac Shakur.
Other musicians in his life include a music professor father, a concert pianist mother and grandparents who owned a record store with a wide variety of music.
He followed up his 1995 gold-selling album, Bonafide, with a platinum album Cool Relax two years later.
Whose wisdom about money do you feel admiration for?
Growing up, pretty much the only person that I was close enough to really see financial things happen was with my Dad. I grew up just naturally seeing the way he did things, and pretty much following the way.
When you come into money your first time, you have to go through that whole period of kind of going your own route, thinking, as an independent person, so you make some mistakes. But eventually, you get composure.
When you first had your golds, and your platinums, did you go out and treat yourself?
Great things come about when you have some success, you know?
My first house - thatÂ's probably the biggest investment IÂ've made. ItÂ's where you rest your head, so thatÂ's probably the greatest thing IÂ've accomplished.
From whom have you learned important lesson about money?
Basically watching the record company that IÂ'm at operate and do their thing. ItÂ's like IÂ've gotten more of a sense of business for the actual creative process.
YouÂ've applied it to your own music.
IÂ've applied it to my music, you know. And the politics that IÂ've been involved in let me have a higher perspective or a better perspective.
So you have a better sense of how to write and produce a song that will meet approval?
Yes. I think the album Cool Relax is kind of like an effort for me to be more commercial, in terms of just what the vibes were, on the radio, or that people in a mass were listening to. The first album was much more just kind of like me experimenting.
Do you have any regrets about moving into a more commercial direction?
I wouldnÂ't say so much regrets. IÂ'd say thereÂ's growth. IÂ'm just more wise now.
Stylistically, where IÂ'm going with my music is a balance between what IÂ'm feeling inside and also what I see happening on the radio.
WhatÂ's changed about the role of money?
I donÂ't think itÂ's changed. To me, money is the most evil thing on earth.
But itÂ's what our society made necessary.
This industry is a real test for a lot of people - especially kids that are romanced in this industry - because money will change your life as far as you let it.
Having money is a greater responsibility than not having any.You really have to stay grounded and not let it affect the way that you would grow normally.
How is it a greater responsibilit for you?
I want to maintain where IÂ'm at in my life and want to say I can keep my house, or keep my car, keep my studio and just have that sense of security. But at the same time I want to be able to provide for my future family and my family right now.
ItÂ's just more and less to worry about. ThereÂ's a lot of different things right now that are beneficial to me moneywise that come about. If I take them, I can go ahead and do it. But then again, in some cases, I mean, itÂ's like, sacrificing creatively where I want to go.
When I was really trying to get my foot in the door I was willing to sacrifice certain aspects of my own judgment in creativity, or whatever, to gain the money. Now I can plant two feet solid, and just make decisions creatively that are going to affect me financially.
WhatÂ's the most important thing you do with your money, aside from meeting your basic needs?
I have a lot of friends that are just kicking with me, or whatever. And just buying somebody a burger that doesnÂ't have a dollar, you know - thatÂ's a good thing to me.
IÂ'm trying to use it in a positive way. IÂ'm not trying to let money alter my normal way of thinking, which is trying to be the best I can be as far as just a person, a musician.
How does it feel to make so much money?
It feels great. ItÂ's a kind of thing where I see other people struggling, and I see the way a lot of my close friends, their normal lives go down. It makes me appreciate where IÂ'm at. It's a big reality check every time I get some money.
IÂ'm incorporating right now. Barcilek Productions is my production company.
When I do get some money, IÂ'm trying to do shows. IÂ'm trying to do promotions and just different things to get these groups started and out there.
Do you have a personal financial adviser?
Yes, I do.
ItÂ's been cool, because itÂ's helped me be really organized with the whole thing. Whenever thereÂ's money that needs to be paid out, thatÂ's the most organized way to do it.
YouÂ've mostly invested in things, like a house, and a car, but you donÂ't own any mutual funds?
No, I havenÂ't done any investments really as far as the stock market.
Do you ever write or sing songs about money?
In different ways, yes, I have, and itÂ's always been a reality - money involved in relationships, money involved in just being out, you could be in a club, whatever.
Is it about people that have money, or people that donÂ't have money?
Both. Sometimes it is. Sometimes itÂ's not.
It is a subject that you think about creatively?
Yeah it is. ThatÂ's reality, so pretty much I try to put reality in lyrically when IÂ'm writing.
Are there drawbacks to earning so much at a young age?
The only thing is the jealousy involved, of other people on the side that see you benefiting or whatever.
YouÂ've performed at a very young age, in high school, and crossing the color barrier in terms of what knds of songs you choose to perform. Do you take risks financially?
IÂ've taken lots of risks. I went on a two and a half month tour that I thought I was going to come back with a little money in my pocket. And I ended up doing these shows, knowing halfway through, I wasnÂ't going to make a dollar. I went ahead and finished the tour.
It was two and a half months of just riding around on a bus, just giving people the show that they want - hopefully that they wanted to see. All the shows were great, and people gave love, and when I got back, I felt, like, cool.
It was disappointing knowing that I spent all that time and didnÂ't really earn anything. But then again I did earn something. Because that is kind of like an investment - those people who come to the show might or probably will go out and buy the album.
WhatÂ's been your biggest financial mistake?
Probably certain videos that IÂ've done and spent a lot of money on. You spend a whole lot of money for a certain director or a certain look, or whatever, and it just doesn't end up turning out.
Best financial move?
The greatest thing IÂ've done is probably Cool Relax, putting that out, and actually doing the videos and spending the money to get exactly what I was feeling for the videos, because then those songs eventually went platinum.
In the way contracts work, the record company fronts the money, but you have to pay it back.
What advice would you give a young person about money?
Just to take it slow, that saving is the best thing you can do. YouÂ've got to take care of taxes early, because, you know, they will haunt you.
Is that something that youÂ've experienced?
I tried a couple of times to wait a while to pay them and wait as long as I could, and then it ended up being the wrong time.
Take care of your taxes, make sure to have an accountant. Money is kind of, like, you have to live with it to know, and you have to experience it hands on. Because itÂ's about your own decisions and how you go about forming your judgments, and just growing as an adult.
Anything in particular that you wanted to share?
I would actually take a quote, not from one of my songs, but actually a Lauryn Hill song that says wisdom is better than silver and gold. And, I think, in certain ways silver and gold can be a way toward gaining wisdom, because of the fact that it takes responsibility and takes just the knowledge of what you want to do.
Any particular song that you wrote about money?
Actually there was the one song I wrote called "FoolÂ's Gold."
The lyrics are saying: I bet youÂ're going to go for broke, you know. But foolÂ's gold - you canÂ't put your faith in things that look valuable, but that really arenÂ't. Because you could still be unhappy and be the wealthiest person alive.
Written by Marjorie Backman, a copy editor for CBS.com