When you’re born into a family whose legacy is intertwined with groundbreaking success in music and entrepreneurialism, there’s an certain legacy you have to live up to. Not everyone is built for that kind of pressure. Fortunately, Rev. Run’s son, Diggy Simmons, is a chip off the lyrical block. With his mixtape grind—The First Flight and Airborne—a heavy Internet presence, a strong management team, record contract with Atlantic, and several outside deals is the works, it seems like Dig is well on his way to blazing his own trails with a promising career ahead of him. XXLMag.com recently caught up with the young star to chop it up about his music and getting into the family business.

XXLMag.com: As a second generation MC how would you categorize what you do and where you fit in?

Diggy: Well, I mean honestly, I don’t think I fit into a certain box. Being that I’m still on the come-up, I don’t feel I’m commercial yet. I’ve been doing my thing on the Internet and I reach a pretty wide variety of people. I have my female fans all the way to the older crowd that enjoy listening to hip-hop music. So there’s really not a box you can put me in when it comes down to my music.

How’s your album coming along so far? Are there any particular producers you would like to work with on your debut?

I haven’t really started working on the album yet. We’re kind of just mapping out when we really want to do it. But who would I want to work with? I think I’d want to work with Just Blaze; No I.D. would be cool to work with, Pharrell or just the Neptunes in general. ’Ye (Kanye West) would be cool, too.

What are some of the things you have going on outside of your music people may not know about?

I have a lot of things going on I really can’t speak on in detail at the moment, but I’m working on so many things outside of my music. I’m excited for it all just to happen and come into fruition, but I’m working very hard.

Can you speak about how you secured that AT&T commercial which features your record, “Great Expectations?”

Man, that’s that Violator Management doing their thing. They [AT&T] came to Violator with that whole concept, which humbled me more so because that concept was something that was in my content from my earlier music from my first mixtape The First Flight that I released last December. It just let me know that a lot more people than I think are looking.

How receptive have DJs been to your music thus far?

As far as the DJs, they’ve been real receptive, especially like Mister Cee in the beginning. It might’ve been DJ Enuff that spun my song “Oh yeah” with Lupe Fiasco and Pharrell a couple of times, too. They’ve all definitely been real cool with my music.

Who are some of the artists that inspired you to pursue your dreams to make music—besides your father, of course?

I mean, Jay-Z all the way from Reasonable Doubt to Blueprint 3, I have every Jay album. Jay is somebody that inspired me, Em’, Nas, Kanye West, Lupe Fiasco… you know? I guess some of the core people that are really looked at. I also listened to A Tribe Called Quest and the Wu-Tang Clan as well.

How do you feel about the impact other young artists like the New Kids, Justin Bieber, Roscoe Dash, Chuckee & Lil’ Twist, Cali Swag District and Willow Smith are making? It’s like the kids are taking over again.

Man, it’s a beautiful thing to really see young people have that drive and ambition to make it on the Billboard charts. Justin is a friend of mine. We both have been friends before he blew up and to see him turn into a megastar, it’s crazy, man! It’s just a beautiful thing.

How did it feel to spit alongside your father and the legendary Ice Cube on this year’s BET “Cypher Sessions” segment during the Hip-Hop Awards?

It was great. The BET cypher was something that I always wanted to do and it was great to do it with my dad.

As an artist, what do you want people to take away from you and your music?

I’m just trying to be hip-hop in general, you know? Break boundaries, just really do it all… I’m really trying to push the bar with hip-hop and keep going with it. —Derryck “Nes” Johnson