DJ Khaled is known for being uniformly positive and having few regrets. However, he did express one during an interview with Shannon Sharpe — and it involves Drake.

During a recent appearance on Sharpe’s Club Shay Shay podcast, Khaled explained that years ago, Drizzy DM’d him on MySpace, but the DJ and producer had no idea it happened.

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“Drake told me a long time ago that he used to hit me on MySpace,” Khaled began. “And I didn’t know how to work that MySpace stuff.”

“I say to myself, oh my God, if I had an opportunity to sign a Drake, or work with Drake before Drake was Drake…” he said, trailing off while thinking about the missed opportunity.

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But Khaled explained that he felt proud that The Boy messaged him back in the day.

“It just shows you that he had love for me as a producer, a DJ, and as a artist,” he said (Khaled made beats under the pseudonym “Beat Novacaine”). “The music I was making, he had love for me. And that’s so dope because that’s one of the biggest artists in the world… Just to know that before he exploded, he was listening to DJ Khaled too.”

You can see the exchange below.

In that same Club Shay Shay sit-down, Khaled expressed his skepticism about the need for professional money managers.

After talking about how his parents taught him to put effort into his dreams and value the capital it generates, the 47-year-old producer clarified to Sharpe that he takes care of “everything” himself.

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“I don’t believe in no accountant, I don’t believe in — what’s the thing they call — money manager,” he said. “I pay the grass, the car washman, the guy that’s cut my hair, the electric bill, the car note, the mortgage.”

“No disrespect to all you beautiful business managers out there — I don’t want to mess up your hustle — but I’ve heard a lot of crazy stories, okay?” he said.

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“There’s no way in the world I’m letting somebody have the power to touch the hard work. No way.”