When Apple Music acquired Beats for $3.2 billion back in 2014, it was groundbreaking on a variety of fronts. It made Dr. Dre the richest man in rap at the time, skyrocketing his net worth to around $750-800 million. It also was Apple's largest acquisition ever; which is saying a lot for a company that has the largest cash hoard (over $250 billion) of any company that isn't a bank. But according to Beats cofounder Jimmy Iovine, the Apple deal almost didn't happen because of a seemingly harmless minute and a half video.
On May 9, 2014, Tyrese posted a now deleted video that showed him in a studio along with Dr. Dre. In the video, both Tyrese and Dr. Dre seemingly confirmed the then rumored multi-billion dollar Apple deal, which had been reported the day before, but wasn't yet confirmed by Apple. In the video, Dre said that he was "The first billionaire in hip-hop, right here from the motherf—ing West Coast, believe it."
In the HBO documentary, 'The Defiant Ones,' Jimmy Iovine said that as a result of the video, he thought that Apple might have pulled out of the deal. "We had gone for like six weeks without it leaking," said Iovine. "This thing has leaked, this thing is loud."
"I had wanted to work with Apple, at that point, probably 10 years, maybe more than 10 years. I'm like, 'how could this be possibly happening?' So sure I thought the deal could blow," he said.
Dre went on to say that he regretted the video. "I was in the studio, excitement was in the room, you mix excitement with a f—ing fifth of alcohol, man, something terrible is bound to happen," said Dre. "That is in the top three most embarrassing moments in my life."
Despite the video, the deal did go through, and though it didn't make Dre a billionaire, it made both he and Iovine a whole lot richer, and Apple executives in the process.