Jae Skeese is a rapper who is making a name for himself with his gritty narratives and candid introspection. He is the first signee to Conway The Machine’s Drumwork Music imprint. His new album, Ground Level, is coming out in August and features production and guest appearances from heavy hitters like Big K.R.I.T., Sauce Walka, Project Pat, Jay Worthy, Lloyd, Project Pat, Statik Selektah, and Ski Beatz. Skeese is known for his unfiltered honesty and music that resonates from emotional depth. With a major single and more attention on his upcoming project than his previous releases, Skeese is set to make the biggest impact of his career so far.

When he sat down with us we discussed DJ Screw, shoes, life lessons and much more.

“Ground Level is me taking the next step from coming up out of the basement and building
on top of the foundation I have been laying the last three years.”

• Jae Skeese

DGB: I just saw the Sauce Walka & Big K.R.I.T. video. I used to live in Houston off Westheimer and I’d go to the Screwed Up store. What do you think of the store itself?

Jae Skeese: Man, I thought it was dope. So when we pulled up, we couldn’t go in because it wasn’t open. But, you know, just being down there and seeing what it’s like down there, man, it was pretty dope. You could tell it’s authentic. They got a car shop right next door & it was mad people pulling up watching us. It was dope to see it in person for sure.

DGB: Do you like Screw music?

Jae Skeese: Yeah, I always rock with Screw music. I always like to check out the different DJs & their renditions and remixes. What brought my attention to it was obviously U.G.K. Listening to their music, but also hearing the influence on Drake’s music and ASAP Rocky I was a big fan of ASAP when he first came out so you know I’m a fan.

DGB: One lyric that caught my ear, you said you wrote some raps where you didn’t agree with the message. Could you elaborate?

Jae Skeese: When I first started writing rhymes, I was listening to Jay Z, G-Unit, and other artists whose subject matter was different from what I do now. The influence was there, and I was just rhyming without paying attention to what I was saying.

When I finally started realizing where I wanted to go, I wasn’t going in the right direction. I was just so immersed in wanting to do the craft and being great at it. I was influenced by the people that I was listening to.

DGB: What sneaker do you think should be retro’d that hasn’t been?

Jae Skeese: Oh, that’s a good question. I’m going to say the Sacramento 10s. I don’t think those came back. I think the first time they came out was back in 95. I just saw a picture of them on Instagram. They had that good black tumble leather with the purple with the white jumpman on the bottom. Crazy. I want to rock that with the good Jason Williams jersey.

DGB: I’m curious, what’d you learn about people working in retail?

Jae Skeese: I learned a few things, for sure. I learned how to lead a team more than anything. I was in a leadership role when I worked in retail managing people. Working with people, it’s all about communication, you can see that in all areas of life, like not just in the workplace.

What I do now making music and working with the team that I work with now, it’s all about communication. It’s all about finding ways to motivate your team and how to stay motivated yourself. I learned a lot about that, working with a team and having to put something together. Every month we’re turning a profit while staying up to date on everything.

Also just having patience. Things aren’t always going to come as soon as you want them. Trying to flip the whole culture in the store takes time and it’s the same with music. You’ve got to grind from start to finish. My whole thing has been starting from the ground level, so that’s what the new album is called. Starting from wherever you start and then just getting up to that penthouse. You know what I mean? But it takes time and it takes patience.

DGB: So you had the million-dollar dreams. I was curious did you get that burgundy face Rolex you rapped about?

Jae Skeese: Yeah I did, I copped one a couple of months ago man and you know it’s in the Sauce Walka & Big K.R.I.T. video. I’m flexing that joint a little bit we got situated with that joint.

DGB: That’s what’s up. So speaking of the joint with Big K.R.I.T. and Sauce Walka I bet some people might be surprised. You can probably work with pretty much anybody, how do you choose who you want to work with?

Jae Skeese: I’m just a huge fan of hip-hop and music period. When I’m putting something together for whatever reason I get it in my head who I hear on certain records. When I’m crafting in the studio, I think of who will sound crazy on this. I study music kind of to a T. Then sometimes it happens by chance. The record with Freeway was like that.

DGB: Really? That song sounds exactly like what you said. You hear somebody on the beat. I thought Freeway was perfect for it, but maybe it’s just how you did the hook.

Jae Skeese: It was really by chance. Free is one of my favorite rappers. I’ve been listening to Free since his first album. I bought his first album on CD. We just happened to be in the studio together. I was playing my music because Freeway and Beans were in the studio. I’m just playing the joint and watching his reactions over in the corner as he’s listening. I’m like yo there’s a spot on that joint for you. He’s like play it back. We play it back. He’s like shit play that beat. I’m going in and shit. He did the verse right there on the spot.

DGB: How do you choose those geeked-out song titles? They’ll be from one line or the name of a shoe but the rest of the song will be about some other shit. The song’s named after the shoe but then that shit works.

Jae Skeese: Trying to stay different and not being obvious. I want it to be something where when you see the name of it you have to listen. I got a joint called Union 2’s. As soon as you see that, you’re like, Union 2? I know that shoe. Those are fire, I want to hear that. Then I got another joint called Bonneville. I mentioned the car in the song, but that specific car fits the overall mood. On my side of Buffalo when you see a Bonneville creeping up on you, you’re ready to run just off that.

DGB: What’s your biggest career regret and your best decision?

Jae Skeese: I have no regrets. I think everything that I’ve done up until this has been either successful or it’s been a lesson. I don’t regret anything because I’ve learned so much in the last four years. My best decision so far has been just staying the course. You take one step forward to take two steps back and then take three steps forward to take two more back. That’s just the nature of the game. Staying down has been my best decision. I could do something else, but that would be taking an easy route and I’ve never been that type of person.

DGB: If you had continued in retail or just stayed in a regular job what do you think you would’ve done?

Jae Skeese: So there’s a time in 2015 when I moved to Syracuse. I had just said fuck music for a minute, when I had my daughter. I wasn’t even really able to do music because I was working two jobs and taking care of a brand new kid with no support system outside of my daughter’s mother. We had just moved. We didn’t have any family or friends out there. So my plan was trying to climb the corporate ladder. One night I was standing there and I’m like “What the fuck am I doing here?” It’s like four in the morning. I have to figure it out. I moved out to Buffalo after that and I’ve just been locked in ever since.

Ground Level is out on August 24th.