Back when he was courting record label deals, rapper Shyne, also known as Moses Barrow, had a tough decision to make. Typically as an artist, entertaining major label recording contracts is a dream come true. However, the frustration comes when you’re trying to decide which avenue will not only benefit your music, but also your artistry and career. So in 1998, with that on the brain (along with a rising popularity), Shyne made the decision.

“I called Mark Pitts and I was like, let’s do the Bad Boy deal,” he tells REVOLT. “Because we didn’t close the Def Jam deal yet.” Facing a competitive bidding war between the house that Russell Simmons built and Sean “Puff Daddy” Combs’ dream-turned-multi-platinum plaques, Shyne, now proud music ambassador to his native of Belize, had an inclination to choose the latter. “Something told me to do the Bad Boy deal,” he recalls, before adding “I got more than any new artists had at the time [and] I still got to keep my publishing and do an incredible deal.”

According to Shyne, it was more than just the glitz and glamor associated with the hit powerhouse that allured him to sign the deal. “I felt like Puff, he was the Phil Jackson and he demonstrated that.”

“I felt like I wasn’t ready to go to Def Jam and do it by myself,” he admits. “I don’t think I was Jay Z or DMX, who were ready and had their team and Lyor [Cohen] and Russell [Simmons] and them could just give them support. I think something in me just felt like I still needed to be developed, cultivated, and I needed to learn a bit more and I just felt that Puff could do that and Bad Boy could do that.”

Shyne recently performed at the Bad Boy Family Reunion Show at Brooklyn’s Barclays Center, reporting live from Belize. Check out the standout moment here, and see his sit-down with REVOLT below.