I went to one of those Fame-like high schools for the creative and performing arts, where I met Questlove. He and I formed a group, around 1986, 1987. I started focusing less and less on visual arts and more on music. I cut my arts classes to go and sit in on music classes, and music theory, and started tagging along with Questlove to his extracurricular music lessons on the weekends. And then, between 11th and 12th grade, I lost my mother. She was brutally murdered.

I think it was then that my focus became really, really laser. My mom had always been one of my biggest supporters, my biggest fan, and she herself was a singer. So she always encouraged me to pursue my dream. As did Questlove’s mom. They were our two most staunch supporters. So when I lost my mom, there was no more doubt in my mind about what I was going to do. The focus just became, “How long is it going to take?” So we started rehearsing a lot more, working a lot harder than we had worked before. It became a reality for us. I knew I wanted to be a professional musician, and that Questlove and I would be partners or bandmates, be in a band of brothers for a long time. I think he knew that maybe earlier than I did.

A little after high school, we were busking on the street, in kind of the Greenwich Village of Philadelphia, at the intersection of Passyunk and South Street. That’s where we refined our craft, so to speak, with regards to mass appeal. To be all things to all people. To people who were into rock and roll, we had a rock edge, while maintaining the artistic sort of jazz integrity that had been instilled in us, while maintaining my credibility as a MC. It’s always been a delicate balance, and we refined the nuances of what we would become, just wanting to be able to please all the fans. We wanted to transcend age and gender and race and religion and place of origin. And at that intersection in Philly, it was the first place we had that kind of opportunity, to see if we had the chops, and I think it was when we began to feel confident that we did.

We would perform songs that we created on the spot. That’s when I realized how good I was at freestyling. Questlove would sometimes point things out while he was doing the beat, and I would incorporate whatever he said or pointed to into the verse, right there on the spot. I kind of realized that could be thing. We would come out, just start playing music, and I had no idea what songs we were going to perform. I would just start rapping, and add on what was happening in real time. I guess it was sort of Zen. I would free my mind of just everything. I would clear it. Take out the stress and stretch it and make my mind a clean slate, if that makes any sense. And only deal with what I was seeing and what I was experiencing at that particular point in time, and make observations. Like right now, I’m sitting beside my 9-year-old daughter, so if I were doing it now, I would start to think of words that rhyme with the number 9, words that rhyme with the word daughter. Then I would look beyond my daughter, look around the room. But it doesn’t get as big of a response from your audience as incorporating them. What their T-shirt says. The style of pants they’re wearing. Whatever someone’s style of hair is. So you look for things that are super-unique, that would further reinforce the fact that you are making this up on the spot. As a good freestyle artist, you kinda process your surroundings and your audience all in an instant, and you connect.

And it’s not even about the words you’re saying. It’s about the connection with the audience I was performing for. Because when I started to travel, and I started to go to non-English speaking countries, the audience would have no idea what I was even saying. So it became more about the way in which I said it, and making eye contact with the audience. It was about the attitude and the energy, less about the words and more about how the words were presented.

I kind of wish that that world was as viral video crazy then as it is now, that the technology had been there, because those were some amazing performances, and they were one of a kind. You had to be absolutely present, only in the moment. But it’s not like there’s a super-definitive moment where a beam of light opens up and you hear the chorus of angels. Maybe for some people, but for me, it was more like, “Wow, I’m good at this. When did I get so good at this?”