Erick Sermon has accomplished many things throughout his long career — but he’s also passed up some big opportunities along the way, and one of the biggest was not signing G-Unit mogul 50 Cent when he had the chance.

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Speaking to Math Hoffa for his My Expert Opinion podcast on Saturday (October 28), the EPMD legend recalled how a serendipitous next-door neighbor introduced him to a rapper who would become one of the biggest names in Hip Hop.

“Well, Cory [Rooney, then Senior Vice President of Sony, the parent company of 50’s former label Columbia] lived next door to me, alright?” he began. “And Cory was with Sony and [production duo] Trackmasters [who worked with 50 Cent early in his career]. So he brung 50 to the crib. And you know, this is early 50. 50 used to come to the house all the time, and we’d do records. So, he was Def Squad… Cory just felt that it was best for him to be over here.”

Sermon remembered producing 50’s track “Da Heatwave.”

“That was the first single that I did after ‘How to Rob,’” he said, mentioning that Fif’ shouts both him and Def Squad out in the record’s outro. “That was his first single before he got shot up [in May 2000].”

Sermon said he was unconcerned back then about 50’s habit of dissing pretty much everyone, as he famously did on the controversial “How to Rob.”

“As far as the barking — whoever he was dissing, I didn’t care,” Sermon explained. “If you roll with me, it was cool. I wasn’t tripping on that. If you are with me, then they’re gonna have to say something to me, too.”

Check out the interview below, beginning at the three-minute mark.

50 Cent isn’t the only artist who Erick Sermon almost signed.

Back in 2012, the “You’re A Customer” rapper revealed that he’d also almost nearly signed The Notorious B.I.G. — but ultimately passed on that opportunity as well.

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“I coulda [signed The Notorious B.I.G.]. Biggie Smalls came to my office with my ex-best friend,” he revealed exclusively at the time. “He brought him to me, but I ain’t hear him though. I guess I wasn’t paying attention. And then after that Biggie Smalls came to my video shoot for ‘Hittin’ Switches’ and stayed there all day with Puffy, ‘cause Puffy shot ‘Hittin’ Switches’ with Hype Williams.”

He continued: “That was Hype Williams’ first video. And then they sat there and Biggie Smalls was telling a girl named Tracy Waples, ‘I need to get on Erick Sermon’s album.’

“And then in the last Rap Pages [interview with Big before he was murdered], they asked him a question: ‘So, who you wanna be like when you get up there?’ And he says, ‘Erick Sermon.’”