7 takeaways from the season 2 premiere of “Caresha Please” with Rick Ross
Almost a year after season one of Yung Miami’s beloved and viral show “Caresha Please” ended, season two returned with a bang. There was no doubt that her fanbase missed the rapper’s candid interviews with celebrity friends. On Sept. 12, a new episode was released with the special guest for the premiere being fellow Florida emcee Rick Ross.
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Ross, who refers to himself as “The Biggest Boss,” began his rapping career in the 1990s but didn’t see mainstream success until he released “Hustin’” in 2006. Since his career took off, he has made popular songs of his own and with some of the music industry’s biggest talent like Drake, DJ Khaled, Chris Brown, Lil Wayne, and more. In addition to his prosperous music career, he’s also known as a thriving businessman due to his multiple investments in restaurant chains Wingstop, Checkers and Rally's, an auto detailing company, the champagne industry, and real estate.
During his sit-down with Yung Miami, he gave insight into how he became a well-rounded entertainer, his business endeavors, love life, beef, and more. See seven standout moments from the interview below:
1. Priorities matter when he spends money on a woman
The entrepreneur has been connected to a lengthy list of women during his long-standing career. When dating, he doesn’t have an issue spending money on a lady who caught his attention. Although the businessman likes to spend on whoever is the apple of his eye, it depends on a few factors, as Rozay believes a rich man should be logical and prioritize according to a woman’s situation.
“It depends on the female I’m dealing with; how much do I really like where she’s at in life?” the Belaire champagne investor told Yung Miami.
2. The expensive items he purchases are also for motivational purposes
Ross has been able to reach his dreams and has been able to afford his desired lifestyle. In addition to his innate ambition and willpower, what inspired him growing up was seeing the nice or luxurious items other people owned. Seeing someone else acquire things that he was unable to afford made him believe he could do the same. Due to this, he hopes others are encouraged to go after their aspirations when they see the grand purchases he’s made like his $30 million jet, his home on Star Island, high-end vehicles, jewelry, and more.
“It’s for motivational purposes only for the hustlers,” he said. “I knew what it would have done for me as a youngster, you know what I’m saying? So, when the youngstas see Rozay pull up and move how we move it… yeah.”
3. There’s a slight possibility for him and Drake to end the beef
The Toronto native and Ross have had a long friendship with some ebbs and flows, and right now they’re on the outs. It’s a disappointment for many to see since the two have joined forces to create hit songs like “Aston Martin Music,” “Diced Pineapples,” “Stay Schemin,” “Money In The Grave,” “Lemon Pepper Freestyle,” and others. The Wingstop franchise owner even teased a joint project the two were working on in 2021.
Recently, things took a turn amid the Drake and Kendrick Lamar rap battle where Ross found himself in the crossfire. The “Hotline Bling” artist took shots at him in his song “Push Ups” after he appeared on Metro Boomin and Future’s collaborative album We Don’t Trust You. This caused the Florida native to clap back and release a diss track titled “Champagne Moments.”
“It depends on how I feel,” he explained when asked about ending the feud. “If I had Luc Belaire maybe that morning, it may be a good day. If I haven’t, you never f**kin’ know because that’s how the game go. It’s just like that. F**k him or whatever it is, but other than that I ain’t lose no sleep.”
4. He purchased his jet to make more money
Jets that celebrities usually take flight in are typically charted, not owned. The upside of utilizing a private jet helps them avoid the chaos at the airport, be secluded from others, and get to their desired destination on time. Since The Biggest Boss likes to make as much money as possible, he's always wanted to buy a jet one day. It was a long journey of flying commercial airlines, but he was able to afford his own, which cost him $30 million. Now he’s able to make three appearances in one day because he has his own set of wings.
“I was patient. I was watching all my homies take their jet pics,” he shared. “And I used to like them too. I love to see my homies on they [jets]. And guess what? Me and my dogs, we was on Delta. I said, ‘Let’s be patient, let’s grind, let’s grind, let’s grind.’ And when the time came, I went and got the G550. It hit me [for] $30 million, but once again we on the double up.”
“I want to go buy a jet, and not just to take pictures on IG. F**k that. I want to be able to get money in three different cities in one day, 24 hours,” he said later in the interview.
5. Crispy Kitchen is his next business venture in the food industry
In 2011, the businessman opened his first Wingstop franchise in Memphis, Tennessee, reported Yahoo! Finance. Since then, he’s become a staple for the popular wing brand with nearly 30 locations nationwide. According to the Miami Herald, he became a franchise owner of the Checkers and Rally’s he used to go to growing up in Carol City in 2016. Now, he has plans to launch and introduce an original chicken brand.
“We creating our own chicken brand, Crispy Kitchen. So, y’all going to be able to walk into the grocery stores and buy a big bag of that. Man, we ain’t playing no games out here. This is for real, so we hustlin’ and we having fun doing it,” Ross said.
6. He believes his ex Tia Kemp took an “L” when they parted ways
His baby mother Tia Kemp has grown to become one of social media’s favorite aunties for her animated faces and quick words as she roasts Ross from time to time online. The two haven’t been in a relationship in years, but they never have a problem going back and forth. Ross believes she hasn’t been the same since he’s been in her life, saying it’s one of the effects of losing a “boss.”
“She cool, but she lost,” he disclosed.
“She lost the boss. That’s what we playing for out here. That’s what it’s all about. When you around the boss, everybody happy. When the boss cuts you off, that’s when you get… and I get it,” he added laughing. “I get it baby. It’s Rozay. When you take that L though, that’s a big L. That’s a big L to take.”
7. There was only one security guard with him in Toronto
In July, Ross had an appearance in Vancouver, Toronto that ended in a fight with some locals for choosing to end his set with Kendrick Lamar’s “Not Like Us,” per TMZ. When he left the stage, he was approached by a group of men and things turned physical as he and some of the camp were hit in the altercation. He feels things would’ve been different if it wasn’t just him, his assistant, DJ, and one security guard against approximately 15 men.
“All my homies that travel with me couldn’t come in because of they felonies. If I would’ve just had two more homies with me, we would’ve stripped them n**gas out their drawers and socks,” he insisted.
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