Calboy Tells Flakko To ‘Do The Math’ On Stolen Money 

Chicago rapper Calboy revealed the circumstances behind his departure from the central label system in a recent interview with Flakko on No Jumper.

Calboy, born Calvin Woods, pointed to friction stemming from his 2018 hit single “Envy Me,” which eventually led to his exit from Polo Grounds/RCA Records to his current independent status. When Flakko asked about Cal leaving Dream Chasers management in 2021, the rapper said he technically didn’t leave.

“Technically, I didn’t leave … I wanted to get the f*ck on, so I ruffled a few feathers,” he said. “I stayed only for a few years because I felt like they were holding me.”

Calboy points to Shari Bryant, co-president of Dream Chasers distributor Roc Nation, as the main reason for signing with a management team run by a fellow rapper before ultimately deciding he needed to move on.

“I felt like I needed her on my team … but I was in a situation, and I felt they was incapable of getting me to the next level in that situation dealing with the people I was dealing with from the label point of view.”

He admitted his frustrations with the label led to him “blacking out” for days in solitude. Calboy says he stopped short of using more forceful tactics because “that ain’t business.” When Flakko asked Calboy about how much money he took from him, he didn’t want to specify.

“If you know what’s up, ‘Envy’ was almost six times platinum … over a billion streams. Do the math.”

He later said the song, which peaked at 31 on the Billboard Charts, brought him “just about” $1 million. Despite the rough split, the Wildboy artist doesn’t harbor ill will toward his former business partners, notably Meek Mill and Bryant, who “taught him a lot.”

“I still f*ck with Meek to this day,” he said when discussing the Philadelphia rapper. 

As far as Polo Grounds and RCA are concerned, Calboy chalks it up to them “winning in business.”

In March 2022, Calboy took to his Instagram page to air his grievances with Polo Grounds and RCA. He called for his fans to spam the social media accounts of both companies. He discouraged new artists from signing before calling out Polo Grounds founder Bryan Leach and demanding his release.

Calboy’s latest single, “On My Own,” dropped in July through his Loyalty & Company imprint. 

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