The Perfect Day to Boss Up summary

Before Ross hit it big, he was a struggling rapper living in DJ Greg Street’s basement. His momma was covering his car payments, and he was so broke that he slept in his truck whenever he left town. But the whole time, he was meeting and networking with hip-hop legends like J. Prince, Tony Draper, and Scarface. And they never guessed his situation. Because Ross hadn’t carried himself like a broke college dropout; he’d made it clear he was a boss. 

It doesn’t matter whether you’re driving a Bugatti or a busted Buick. What matters is that you’re driving. A boss grabs the steering wheel, gets in gear, and takes their life in the direction they want to go.

If you’re ever lucky enough to walk around The Promise Land, you’ll find foreign art on the walls. Piles of ornamental bicycles. Horses. A room full of sports memorabilia. Multiple garages containing multiple cars. More classic video games than in any public arcade . . .

Some call Rick Ross a hoarder; he prefers the term “collector.” Needless to say, Rozay did some spring cleaning during quarantine. But one thing he’ll never part with is his watch collection. The Rolexes, the Hublots – they’re worth millions, and there’s no question he’s a boss any time he walks into a room wearing one. 

People in Miami aren’t exactly modest about wealth. In fact, they often exaggerate how much they have. Those Lamborghinis on South Beach? A lot of them are rented. As a young man, Ross saw hustlers get money fast – and lose it even faster.

When he signed to Def Jam and received a seven-figure advance, he went from broke to millionaire. He could’ve easily blown through the money, but for nine months he acted as though it didn’t exist. He performed “Hustlin’” anywhere that’d pay him and squirreled away that money too. Not until Port of Miami debuted at number one did he finally lay out some cash on a house.

One of the first tracks Rick Ross ever wrote was called “Where the Hoes At?” At the time, he didn’t have a lot of experience with quote-unquote “hoes.” He was a nine-year-old virgin in third grade. 

But he was already honing a powerful tool to self-actualization: believing things into existence. He knew where he wanted to go, so he rapped from that imaginary future self’s perspective. Later in life, he used the same tactic when he wanted to become an investor in Luc Belaire – a new rosé. He’d tried it after a show at a club one night and was immediately smitten with the black bottle and its neon-pink labeling.

When Ross received the call from Kanye West’s people telling him to come over to Pinewood Atlanta Studios, he was skeptical. Ross and Kanye go back 20 years – and Ye had always been provocative. But recently, his tweets had started rubbing Ross the wrong way. Still, they had history. So Ross donned a Balenciaga sweater and drove over in his Rolls-Royce Phantom.

Kanye had relocated his music operations, his apparel lines, and his presidential campaign from Wyoming to the seven-hundred-acre film studio in Georgia – and he wanted to show Ross what he’d been working on. At the end of the tour, he suddenly said, “Tomorrow I might tweet that I don’t feel like being president anymore.” His campaign staffer’s response blew Ross’s mind: “It’s going to get a million retweets.”

Rick Ross raps for a living. He prides himself on being able to take down a rival in just a few lines. But he had to hand it to Anderson Cooper. Calling Donald Trump “an obese turtle” in the wake of the 2020 election results? Brutal.

As a large person himself, Ross felt a momentary pang of pity for Trump. But the man hadn’t acted like a boss. He hadn’t accepted his loss; instead, he’d tried to take everyone down with him.