To many music fans, Masspike Miles first came on their radar on Rick Ross’s “Get It Together.” Recording the smash with Ross in late 2008, Miles signed with Ross’s Maybach Music label.

This connection has lead to videos with Yo Gotti (“Here We Go”), Shawty Lo (“Perfect Women”) and even more collaborations with Ross: “Cigar Music” and “Love Drunk.” He’s also released a new mixtape, The Pursuit of Happiness hosted by Rick Ross & DJ Khaled.

Miles Wheeler is the product of Parisian mother and a father from Cape Verde, a collection of Portuguese-speaking islands off Africa’s West Coast. He was born in 1980 in Sacramento, California. As a child, Miles moved to Boston with his family to be closer to the city’s large Cape Verdean community.

Miles’ father, a jazzman, named his son after legendary trumpeter Miles Davis.
And it didn’t take the kid long to launch his own musical career. Miles quickly caught the eye of legendary R&B producer Maurice Starr, who also discovered New Kids On The Block and New Edition. Miles became the lead singer of Perfect Gentlemen, who Starr signed to Warner Bros in 1992. He was just 11 years old. Miles was soon working with artists like Bobby Brown, Dallas Austin, Eddie F and Montell Jordan.

But Perfect Gentlemen, despite their talent, never took off like Starr’s other acts. Miles sees this chapter in his life as vital music industry education. “The lessons I learned watching Maurice Starr equipped me for success,” he explains.

A key lesson was patience. He retreated to his Roxbury neighborhood. He alternately spent time working on music and falling into the streets. “This was a difficult time for me,” Miles admits. “But I always knew I’d return to the music business.”