“#Life is an amazing journey on which every traveler must find his own path. The Life Anthology represents all of the emotions, issues, high & lows any one person can go through in one day and sets them to a beat. Hip Hop has been omitted from contention when it comes to defining the average American life. This travesty has unfortunately alienated many rap/ hip hop fans who seek more than just doing a catchy dance or repeating a pathetically slurred chorus. In business, it has also distanced popular brands from really reaching the core of the hip hop community.”

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How’d you connect with Kanye West and GOOD Music?
Ah, that’s the greatest story… when i was in high school, Kanye was in Detroit, he was promoting his album Late Registration, and he was at the Radio 1 station, and I had a good relationship w/ the radio station when I was in high school, because every Friday I used to go down there and rap at the show called the Friday Night Cipher. And its a show where all the rappers, well, a lot of the city’s rappers would come and we would battle each other and the ones who would win the battles would get to rap on air for free. So, I did that when I was in high school. It was me and my best friend, Pat, Pat Pierce… And we did that for like a year straight, and it gave us a great relationship with the radio station.

So, one day Kanye was down here promoting Late Registration, it was on a Saturday, and I had done that show the day before. So, I basically ended up at the radio station and I pretended like I left something there the day before, but really I was just trying to like meet Kanye, and maybe rap for him or something… So I had cds that I was selling in high school at the time… So, you know, I was talking to one of the DJs there, and I remember the DJ telling me that Kanye was right down that hall, and that I should go rap for him. And you know, I ain’t never met no celebrity ever, so, my heart was beating out my chest, like I was nervous as I ever been,… But I ended up talking to him like, “yo, whats up man, I’m an aspiring emcee, I do this show here every Friday”… and he was like, “Oh, good job, keep it up”, and he started walking away. and I remember my boy saying, “Man, you better run for him man, what the fuck..” and I was like “you right..”. So, I tapped him again as he was walking out, and right before his body guard slammed me, he was like “yo, whats up?”, and I was like, “Man… can I spit for you real quick?”… and he was like, “Nah, I don’t have time.. I’m in a rush man, I gotta go”… I was like “Please man! You my hero!”.. He was like “Man, alright man.. but, you gotta spit while we walking out the radio station.. and you only got 16 bars so go.” So I started rapping, and ummm…. as we were walking out the station, basically he stopped walking, and he started just looking at me and listening to me, and instead of 16 bars, I ended up rapping for like 10 minutes and like 100 bars… So, that’s what got his attention. When I was done there was a big crowd wrapped around at the radio station and it was a real big moment.

Basically, that is just how I got his attention. He didn’t want to sign me like right after that at all. We just kept in contact, and I was sending music back and forth over the years, really… and then when he was working on his album Graduation, he invited me to come work with him. I was in LA, just like to take me under his wing. He really showed me how an album was made, all sorts of different types of stuff. And then he signed me shortly after to just GOOD Music, like in 200-, like the end of 2008. Then I got signed to Def Jam later on that year. And then I’ve been working on my album since then. So, I’m about to come out with my album this year…. that’s like the short version, because there was a whole bunch of madness going on. [laughs]
How does it feel to be one of XXL Freshman of 2010?
Aw man… a relief, a blessing. You know, I thought I should have been on it last year, but its even better timing that I’m on it this year. So, everything happens for a reason. Its an honor. You know when you like a young-… when you a kid or any aspiring rapper; All rappers want to be signed or get a record deal with Def Jam or something like that. Or be on the cover of XXL or some type of big magazine, so, for that to happen, its an honor. For that to be my first magazine cover, man, its more than a blessing. Can’t thank XXL enough for that…. My mom was really proud.
Whats one thing that you bring to the table that other rappers don’t?
One thing I know a lot of rappers forget to bring is a sense of themselves on the record and originality. Besides that, I think I just bring a combination of lyricism mixed with something people can relate to. I want my music to be the soundtrack to peoples lives. And my music isn’t all serious, I have a lot of fun in my music, just like people my age have a lot of fun. Going through different issues people go through from like young relationships to young love, or if you going through and just partying all the time, going through different phases, going through being broke, going through being young and starting to live that dream… It is all these different concepts that I incorporate in my music. One thing Kanye taught me to do is do it in a certain way. Keep it a certain level of lyricism, meaning a certain level of conceptual idea. I think that is one thing that I embody in my music, and I can’t wait for everybody to hear it.
When can we expect a finished project from you?
Definitely coming this year 2010. We’re trying to gage it to see if its going to come before or after Kanye’s album. It’s probably going to come before… I say probably around the end of summer. We’re going to drop a couple of singles and stuff..
Do you ever get star struck when working with people?
Hell yeah! Man, I met Beyonce.. I remember the first time I met Jay… Well, really man, the first time I met Kanye was my first time being star struck. The second time was when Kanye had me in a meeting with Jay-Z and I was star struck as hell, and then, the third time I got star struck was when I met Beyonce. Shoot… who else… Man… Yeah, I get star struck all the time man. Like when I met Pharrell the first time, I was star struck. And now these guys are my friends, and they cool with me, so it’s all good.
Do you have time for personal life?
Yeah man, you know.. You always gotta make time to live and have a personal life. It definitely gets sacrificed sometimes but, its all for the better. Whenever you on your job, or even if in school, or doing work, you’ve got to sacrifice your personal life too sometimes. Its nothing outside the regular really. I just have a different type of job than regular people.
Whats your favorite song of all time?
One of my favorite songs of all time, its going to sound cliche and shit because I’m like signed to Kanye.. But, the song on College Dropout, way before I knew Kanye, “Last Call”, and its the last song on The College Dropout. That was one of the songs, I think, that most changed my life. It gave me the most inspiration a song has ever given me.. and, really like, it gave me the motivation to keep going even on them days where I didn’t want to rap no more.
Whats your personal best? (the best track you’ve put out)?
Well, my favorite track, no body’s heard yet, I recorded it. It’s a song called “Celebrity”. And we’re thinking about putting a video out to it, and like putting it on the radio and everything. Its real dope. Its different though, but its dope as hell. Yeah, its one of my favorites. The thing is, when you decide to put out a song, you have to decide if you want to go the regular cliche way and put out an easy radio song or do you want to go against the grain a little bit. And that’s what it is. The song is undeniably good, well, to me it is. And not just because I’m on it, but because the production is flawless. Its great.
Who produced it?
My homie Filthy Rockwell. He’s from Detroit. And he’s a real heavy producer. He produced some records for Slaughter House, Royce Da 5′ 9″, for like D12.. and he’s been putting work on my album, its crazy.
So, aside from rapping, what do you do for fun? Or is that all you have time for?
Nah, no no, hell no. That’d be whack if that’s all I had time for. I like to watch movies, because I feel like, no matter what you got going on in life, when you look at a movie it seems like you just forget about all the shit you got going on and focus on that movie. Really good movies can make your problems go away for an hour and a half or two hours. I really love chilling and just relaxing with my girl or a girl or something like that…
Do you have a girlfriend?
[laugh] Yeah, well, you know… I feel like everybody got to have someone special but, I am young too, so, I always keep that in mind.
What advice would you give someone who wants to pursue rap?
Simply that, you have to be prepared. You have to have a good sense of whats good and whats not good, and what people aren’t going to like. And then you have to visualize it. You know, nobody can see your vision like you so, if people hate on you, or can’t understand what you’re doing, don’t let that discourage you, just use that as motivation. And I feel like, if you really believe in something, and truly want to do something that you’ll get your shot. At least you’ll get one shot. So, just keep it going, and do anything you can to like further your success or what ever you’re trying to do. For me it was rapping at the radio station every Friday, when I was in high school. And that gave me connections with the radio station, and that connected me with Kanye, and that connected me with a record deal.
Well, those are all the questions I have for you… Thank you so much for doing this interview.
No problem, I appreciate you. Take care.

Crawl out from under that rock and recognize greatness. If you don’t have it, get his “UKnowBigSean” Mixtape (2009) [here]. This dude is dope but, don’t take my word for it, find out for yourself. Follow him on twitter @Big_Sean. And check out his site UknowBigSean.com. I expect big things from him this year.

MD: Word on the street is, you’re just 14, is that true?
D: Yes, yes… born in 1995. ’95 was my year..
MD: Wow, so young… but in listening to your flow its pretty mature, how’d you get it that way?
D: Oh man, I’ve never heard that before,… uhm, I’m just me. I focus on being me, whether its me on the fashion end or rhyming, I just focus on doing me. I’ve been doing this for a little bit so I guess I’m just me.
MD: Tha’ts whats up… So, when did you start rapping?
D: I first started rapping when I was 5… did that for a couple of years and then I stopped for a while, and didn’t really start back up until like last summer..
MD: So, where do you want this to go, is rapping just a hobby?
D: This is what I want to do. People always look at me, and they see my family… Like they see my dad and my uncle, and think that oh his uncle is just gonna sign him and his dad will be on the project, but no, that is not the case, this is an independent project, and this is something that I am doing for myself…
MD: Being the independent artist that you are, how do you think you can pull away from your family’s shadow?
D: Keep being me, keep doing what I do. Sometimes its almost like people persecute me because of what I was born into. Like they look at my house, wait, its not even my house, because I did not work for it. I’ve just got to keep doing me..
MD: What inspires you? How do you get a concept for a new song?
D: Life, girls, school.. things I went through, things I’m going throught… stuff like that, its all inspiring
MD: Speaking of girls…. do you have a girlfriend?
D: No, ladies… I’m single. [laughs]
MD: [laughs]… well, I bet there are a lot of teenage girls excited about that. So your mixtape was hot, rave reviews on Fly Away and Laid Back.. what were your fave tracks?
D: My favorite tracks? Hmmm… I’m looking at the track list on my itunes right now… It’d have to be Fly Away and Point To Prove… My mixtape came out in December, so my newer favorite track is Set Me Free, its a single I dropped last week…. but, definitely Fly Away, Point To Prove, and Set Me Free…
MD: With this mixtape, do you feel as though you have a “point to prove”?
D: Yes, most definitely… People look at me and expect me to be rapping for fun, and this is something I want to do, I’m not what you think I’m going to be and do what you think I’ll do. I definitely proving myself to everyone…
MD: Thats real…. so if you were to compare yourself to an artist who would it be?
D: What do you mean..?
MD: Like Ye’ compared himself to the new Slick Rick… you would be?
D: I don’t remember him saying that… wait, he said… [raps] “hey young world, i’m the new Slick Rick, they say I move to quick”… Ummmm.. I don’t know. I’m me. I’m Diggy.
MD: Thats real… but, what artist do you like or influence you?
D: Lupe Fiasco, Kanye West, Jay Electronica, J.cole, Andre 3000, Mos Def, Lykke Li… and many more.
MD: If you could collab with any artist, who would it be?
D: Man,… Thats a hard one, there’s just too many…
MD: If you could give advice to someone trying to get the same buzz you have, what would it be?
D: Keep working until you get noticed… Like I had my blog [Life of a Jet Setter], and people started to pay attention to my fashion, and then I did some music, and now there’s twitter. Twitter is like your own PR. And you just put your music out there. For me, some people didn’t even know I did music until sites like 2DopeBoyz posted me, and then I started getting recognition from that…So, just keep grinding…
MD: That’s real, so true… Thanks for doing this interview, definitely appreciated it… make sure to come back when you drop that album!
D: Of course, no problem… I will whenever, just hit up Cathryn.

Definitely check Diggy out on his blog at Life of a Jet Setter, and his twitter is @Diggy_Simmons… A real fresh kid on the rise.
- Miss Dimplez