All things considered, Devin Miles is doing well for a 21-year-old college dropout.
He is fresh off the first two performances of his "Fly High" tour with California-based rapper D.U.B.B. as he sits in his Washington Square apartment, reflecting on a journey that brought him from a child who was too afraid to curse in his rhymes to a young man hoping for stardom.
He hasn't much time for rest. In July, Miles has tour dates in Cleveland, Denver, San Diego and Los Angeles. He knows he has to keep working. If he's not, someone else will.
So goes the trouble of chasing one's dreams, especially when that dream is to become a figurehead in rap music, as Miles aspires to be. So far, he's on the right track. He's three EPs deep and working on his first full-length release, he's built a following that expands beyond Pittsburgh, and he's done it all building from the ground up with a small group of friends as his partners and a supportive family behind him.
Five years from now, he says, he hopes to have headlined five national tours as well as a few overseas, have his own small label with young artists working under him and have produced two Grammy-nominated albums.
"Actually three," he says, correcting himself.
"I want to be a household name in rap: You dig rap, you dig me."
Growing up in Penn Hills, Miles was constantly surrounded by music.
His father, Bobby Simmons, owns a "ridiculously amazing" collection of records, as Miles puts it, and it was that exposure that began Miles' love affair with music at a young age. He was obsessed with "oldies" like The Temptations and the O'Jays; to this day his favorite artist is Ray Charles, who he admires for his work and perseverance.
When he was only 4, Miles began taking piano lessons, a practice he continued until he was 17. Someday, he thought, maybe he could play like Ray or perform like The Temptations.
"I would always want to mimic them," Miles says. "And I would always wish that I could play music like them or be at their standard or at their caliber someday."
Miles remembers his older brother, Demarcus, playing him Jay-Z for the first time. He was the first rapper Miles ever heard and remains his favorite emcee.
When Miles was 10, Demarcus bought him a copy of the Dr. Dre classic "The Chronic." All was good until it was discovered by Miles' mom, Jan, who considered to be inappropriate music.
"My mom found it and she snapped on him and snapped on me because there was so much bad, negative stuff on there," Miles recalls.
Demarcus continued to allow Devin to listen to rap in secret. Demarcus was 16 or 17, Devin estimates, when he began writing his own lyrics and rapping them to Devin over instrumentals they would find online.
"He would rap his lyrics, and I thought it was the coolest thing ever," Miles says.
So when he was 12, Miles began to write lyrics himself. At that point, they were for nobody's ears but his and his brother's. Devin was weary to use cursing in his lyrics until his brother eventually gave him the pass.
Today, Devin says, Demarcus is amazed to see how far his younger brother has come rapping, and Devin is proud to make his older brother happy. Bobby is proud, too, to see his son still playing music all these years later. Jan, meanwhile, has come around. She expressed concern when Miles made the decision to drop out of college after his sophomore year at Duquesne University but has since seen the progress Miles has made.
"It's a pretty awesome feeling to have your family really support you," Miles continues, "especially in something like this that most people see as a super long shot."
Miles met John Welch as a high school freshman at Central Catholic.
Today, Mr. Welch goes by "Christo" and is Miles' primary producer, roommate and best friend. They first got serious about making music together when they turned their dorm room at Duquesne into a studio.
Miles began sharing music on his Facebook page. It caught some people's attention on campus, but it wasn't being taken completely seriously until he shot the video for a track titled "Spaced Out" and released it online. It went viral before it was eventually flagged on YouTube and taken down for inappropriate content, mainly the smoking of marijuana. Still, for Miles' camp, it was a victory.
"But that moment, whenever I dropped the video and saw that people really received my music and liked what I was doing was when it clicked in my head and I was like 'I'm really going to do this,' " Miles says.
From there, he began a project called "Miles Mondays," a new release of some sort every Monday. Next came his first EP, "Finding My Own," which was special to Miles because he finally got another friend from high school, Zekiel Thompson, to sign on to be his manager.
After touring to places like Penn State and George Mason they decided to drop out of school and go full time with their music. It was a tough decision for Miles, but it's panned out. In the years since, he's dropped two more EPs -- "This Is How I Live" in 2012 and "In Due Time" in 2013, the latter of which was sponsored by Myspace and has garnered north of 50,000 plays.
Miles has even drawn attention from some big-time rappers. His video for a song called "The Good, the Bad, and the Ugly" aired on MTV's "RapFix Live," with rapper T.I. telling Miles he admired his music and his message.
While performing at a showdown in Texas at SMU, where Juicy J was the headliner , Miles took a chance in the green room and asked for his contact information. He complied, leading to Miles to ask if he'd like to guest on a track.
To his surprise, Juicy J said yes. Miles sent him a song called "S.L.A.B.," a Southern slang for "slow, low and banging" cars. Miles waited roughly two months and had all but given up on receiving a verse when he received a file while lying in bed at 12:30 a.m. one night.
"I leaped out of my bed and like screamed and ran upstairs," Miles recalls. "I called Zeke, I was like, 'Yo, he sent me that song back!' "
Miles has yet to work with either of the two famed Pittsburgh rappers, Mac Miller and Wiz Khalifa, although he's worked with producers for both of them. In fact, he and Miller were close friends in high school when Miles would go to Miller's house and listen to songs he had made.
"If I see him, we're definitely going to talk; we're definitely going to laugh," Miles says. "It was really motivating to see him take it seriously and go somewhere out of Pittsburgh."
Miles keeps his hometown prominent in his music, and together from their studio at their apartment, he and Christo have created a sound they think matches the feel of the Steel City, a sound they call "industrial."
"That's Pittsburgh," Miles says. "It really works out like that, and you can definitely feel the whole vibe of the city if you listen to the music in its entirety."
In high school, kids would joke when he'd tell them he was going to drop a mixtape. Since then, he's faced more than his share of doubters -- They'll criticize him for not having a record with Wiz or Mac, for not having a Plan B, for thinking that he even has a shot at all.
"A lot of people talk because they don't have the courage to chase what it is that they really love, whether it's fear or who-knows-what that's stopping them," Miles said. "People will always try to knock you down."
One low point came in February 2012, when he was featured as one of Jenesis Magazine's "Next five out of Pittsburgh." Miles was excited until he heard negative chatter about his inclusion. He recalls people saying that due to his small body of work, he didn't belong with other four.
"I actually had a talk with my brother," he says. "He said, 'Man, you've been doing this for a really long time, and it's clearly the one thing you love to do, so you just got to keep at it. You've got to say [expletive] what anybody says or thinks, and you've got to just keep trucking along.' Ever since then, my skin's been tough, and we just keep going."
Miles and Christo are working on their first full-length release, titled "Pixburgh," which they believe is their best work to date. Miles was nearly brought to tears recently while performing a track off that project, titled "What They Gon' Say?"
For Miles, that song is the response to anyone who may have doubted him. It's about his relentlessness in pursuing his dream, it's about those who have supported him, and, mainly, it depicts a moment that Miles says made him realize his music actually helps people. At that point, what can anyone say to stop him?
"That's something I think people who don't agree with the lifestyle, don't agree with the career choice, don't understand," Miles explains. "And if they don't, there's still nothing you can tell me. You can't knock what I'm doing because I am helping people and I am touching people, and I am making an impact in somebody's life somewhere."