The unprecedented attention that Cinco de Money brought Money’s way—it landed on Rolling Stone’s “40 Best Rap Albums of 2015” list, for instance—motivated him to change his plans for the mixtape’s sequel. “Part two was done when part one was done, but now that Cinco de Money has been getting so many write-ups and so much attention, I had to go back,” he says. “Two gotta be better than one. Or you’re moving backwards.” Before he goes public with an entirely redone Cinco de Money 2, Money will drop a new EP—he hasn’t pinned down the title or release date, but he says it’s imminent.
Born Tiwan Raybon, Money hails from the south suburb of Harvey, where he’s lived for most of his 28 years, but he’s undeniably part of Chicago’s hip-hop community. “I’m originally from the Hundreds; that’s where I stayed,” he says. “We didn’t do shit out there, so we don’t claim the Hundreds. Got love for the Hundreds, my peeps still stay out there, but we from out Sibley [Boulevard].” His father turned him onto music, playing Slick Rick and Eric B. & Rakim records at home. “I remember wearing three-piece suits at two years old, a microphone in my hand, ponytail, and just singing everything my daddy put on,” Money says.
His father’s house was a magnet for parties. “Like, if there was gonna be a party, a New Year’s party or birthday party, it was at my crib.” Extended family and friends packed the place late into the night, and Money was the only kid in the room. “I was always at these parties, bro, and always doing shit I wasn’t supposed to be doing,” he says. “I seen a lot.”
In the early 2000s, Money would go to teenage parties at the Markham Roller Rink, taking in sets of ghetto house, juke, and footwork by producers such as DJ Thadz, DJ Slugo, and DJ Spinn. “If you wasn’t at Markham Roller Rink on Saturday you wasn’t shit,” he says. Every weekend he’d head to the rink, then take the party to his mom’s house nearby—usually accompanied by one of his cousins, Isaiah Driver, who raps as I.D.
Money and Driver would form a duo called FireSquad in 2005, but they cut their teeth battle rapping, sometimes together and sometimes separately. “That’s back when battle rapping was heavy,” Driver says. “We never lost a battle. We would kill guys on Chicago and Madison on the west side. Or my father had a restaurant on 81st and Cottage Grove—we used to battle a couple guys in the lobby of the restaurant.” Driver says his father, Ralph, has owned a couple restaurants over the years; the joint on Cottage Grove in Chatham was called King’s Soul Food Cafe.
Money and Driver didn’t just rap at the restaurant—they worked there too. They’d open and close the place, fry chicken, bake cakes—anything that needed doing. “We used to freestyle while we was making orders,” Driver says. “We listened to beats all day long. Customers would come in, hear the same record instrumentals playing over and over, ’cause we was down there vibing. We knew that the music will take us [away] from washing dishes.”
Driver’s older brother, Ralph Metcalfe, who raps as Marvo, was close with Driver and Money. He also had more experience with music (he’s 31 now), and both younger rappers agree that his mentorship helped them enormously. “I had my record deal when I was about 15—I was with an independent signed through Universal Records,” Metcalfe says. “I actually taught them how to rap—I was really their main influence, honestly.”