Loved and loathed: Why is Cassper Nyovest settling scores in the ring?

It’s 1.13pm, about half an hour since actor and musician NaakMusiQ made his entrance, and rapper, songwriter, entrepreneur and record producer Cassper Nyovest has just walked into The Venue Green Park, an upscale rooftop and events establishment located on the 20th (and highest) floor of Sandton’s Green Park Corner. While his counterpart dons an unremarkable beige tracksuit, Cassper exudes opulence in a cream suit, a crisp white T-shirt and an orange pair of his signature Root of Fame 990 sneakers. There’s little doubt who the star of the show is. 

Ahead of their bout this weekend, the pair have gathered select media, influencers and celebrity guests for a press conference where sponsors and stakeholders will share details on one of the biggest weekends in South African entertainment in recent memory. The grandeur of this scene and the trajectory of Cassper’s growing business portfolio brings to mind Egyptian Cotton, his indulgent and lushly produced Rick Ross-esque 2020 single featuring Anthony Hamilton. There’s a line in the song where he raps, “Been contemplating giving up rap and become like Keith [Dr Keith Bothongo] … They say surround yourself with greats, I do it frequently”. 

When I catch up with Cassper in the backroom where he and other A-list guests are posted up after the press conference, I ask him if the moves he’s making are slowly pulling him in the direction of his mentor and if his days in music are numbered. 

“What I meant with that line is being exposed to other opportunities that make way more money than music,” he says. “Keith is a property mogul, that’s my mentor. So I’d just love to go into property and just chill, have no beef, nobody hears about me, you know. But at the end of the day I love what I do and I don’t think I’d ever quit music – even with all the money that I’m about to make with everything that I’m going into I’d never quit music, that’s who I am, it all starts with the music.” 

In an industry and genre characterised by easy come easy go, Cassper is hellbent on making moves that will immortalise him. Like Jay-Z, one of his idols and a reference point in the making of Egyptian Cotton, he’s making legacy moves. “Would you rather be a trend, or you rather be Ralph Lauren?” Jay-Z famously said in an interview with T Magazine in 2017, referencing his desire to create a brand empire that will outlive us all. 

Things haven’t always been like this. Cassper’s life has not been without its travails. His mother and father separated when he was young. He dropped out of school and left home as a teenager to chase his rap dreams in Joburg (his baby sister Tsholofelo, whom he named his debut album after, gave him the little money that she had for his taxi fare). He slept on different friends’ couches as he tried to find his feet in the city. Through sheer persistence and never say die attitude, he eventually arrived. Today, Cassper is, arguably, the most talked about entertainer in South Africa, with an preternatural ability to spark debate and go viral at any given moment. He’s loved and loathed in equal measure. 

Over the past few years he’s shrugged off the AKA-led character assassinations and surpassed his nemesis’ career with ease through his iconic Fill Up concert series that’s seen him pack up some of the biggest stadiums in the country, several shrewd business moves and a growing musical catalogue. A decade into his career, he is arguably the most relevant rapper in South Africa, and not because he’s been consistently releasing the biggest rap records, but because you just can’t ignore him. In a genre characterised by luxury and showboating, no one has amassed more trappings of an opulent lifestyle than he has. And he won’t miss the opportunity to remind you of this. 

In the backroom, as he answers a boxing-related question during an interview with Slikour, Cassper trails off topic and begins enthusiastically gloating about the sales of his Root of Fame sneakers. Slikour waits for him to finish then says, politely, “Save this, we’re talking about boxing today.” Cassper chuckles, realising that he just went into full promo mode. 

  His greatest gift is the ability to conjure up business and marketing opportunities and hype them up with such confidence that you are likely to buy into it, even if you don’t really understand why. He’ll find any opportunity to pitch his work, using words like “brilliant”, “unbelievable”, “never-been-done-before”. He’s earned the right to speak this way, and there’s reason to believe that he will speak it into existence. 

Apart from a brief follow-up chat, Cassper and I’s conversation began a few days earlier. We got into everything including the coming fight, his strained relationship with the late Riky Rick, to the influence fatherhood has had on his thinking. 

Congrats on your upcoming fight. How did the idea to start being involved in boxing in this way first come about?

I’ve always liked the sport and been vocal about watching the big fights. That developed into me using it for fitness and simply grew into a real passion. Now I can’t stop, it’s a problem. 

How involved do you intend to be in the sport going forward and what role do you feel this upcoming fight with NaakMusiQ could have in elevating the sport?

I’m truly invested now. I spend a lot of time researching and learning the sport, the history, the business, the people and the entertainment of it. My hope is to draw enough eyes on this to boost the interest in boxing, showcase the talent that these professional athletes are and give them the shine, remuneration and respect they deserve. 

DJ Sumbody, Cassper Nyovest, DJ Tira, NaakMusiQ and Vertex Events chief executive Thato Segaole at a Celeb City press conference in Sandton. (Jabu Nkosi)

When you fought Slik Talk, you mentioned that you were doing it to teach him a lesson, did you feel like that objective was achieved and what’s the most important thing that you felt came out of that fight?

Well at the time it seemed like he learned the lesson. I wasn’t under the impression he’d suddenly be a saint. But I wanted him to know there could be repercussions to this cyber bullying and he’s fortunate I did it in a controlled environment and built some fun around it plus I paid him. But someone else might not take the approach I did and it could end up far worse for him and the likes of him.   

With AKA seemingly back in the picture, do you anticipate that we may eventually get that long-awaited fight between you two? If so, what makes you feel confident you’d beat him up?

I don’t know if it will ever happen because he’s simply scared and will always create silly excuses and demands to get in the ring with me. It’s okay though, it’ll happen whenever he builds the courage. 

 Aside from the fight, it’s been a really tough couple of months with the loss of Riky Rick, Citi Lyts and DJ Dimplez. Do you feel this may bring hip hop together and closer again? Also, what were some of the biggest life lessons you took out of your friendships/relationships with these three artists?

Man, it’s truly tough to answer this. Honestly been a heavy period for myself and so many in the industry. With Riky, he was a brother to me, it’s obviously well publicised we had issues and weren’t as close for however long. I still struggle with it cause not only did I lose a brother, I also lost out on time with my brother while he was still here. That hurts and somehow I have to move on and be thankful that at least we were back on talking terms. Citi Lyts and Dimplez, also sad and truly heartbreaking cause both these gents were such kind souls, always respectful and not bothering nobody. I’m glad our paths crossed, I wish both of them were still here with us. Go boima. 

Summer Love has been extremely popular even without much push on your socials. Can you talk me through how that song came about and why you feel it’s been able to achieve so much success?

We were in London for shows and my team that side put a studio session together with Raye, a really amazing soul and extremely talented artist. My producer Alie Keys always travels with me so getting the record done was pretty smooth. The song is beautiful and sometimes the biggest records aren’t always the most promoted. The people decide and push it organically. We are scheduled to shoot the video in London in late April, though. 

Siyathandana is arguably the biggest song of your career. When you were working on it, did you get a sense of how successful it’d become? Also, does the drama with Boohle [in an interview with MacG last year, Boohle claimed she wrote most of the song and seemed to suggest Cassper was hardly involved in the recording process] take anything away from how you look back at the song?

Hehe, I know Youtube says Siyathandana is my biggest record but Baby Girl is actually the biggest. That doesn’t take away from how amazing and how massive that record went. We just made music and the energy was great. Abidoza is an amazing producer so sessions with him always feel like we have an incredible song. We weren’t trying to make a hit or chase charts, but we were definitely intentionally making a great song and thank the Lord it came out as beautiful.  

As far as Boohle, it’s in the past. She said what she said and as always when such things happen I move forward. No issues though, we made great music and if it’s meant to be we’ll work again in future. Great vocalist and talent. 

Root of Fame has been another big success story for you. How did the idea to get involved with Drip come about and how fulfilling has this whole process been for you? 

Lekau hit me up via social media and after a little while we met up, had great conversations. I liked his view point and absolute dedication, we always started building immediately as we hit it off. One of the greatest experiences of my growing career, there’s so much more coming from this partnership.

After the relationship with Ciroc ended, did you intend on being involved in the liquor business again? If so, can you talk me through the process of how that intention then led to the founding of Billiato?

The crazy thing is even before the Ciroc deal me and my manager spoke about having our own liquor brand. We were actually presented with an opportunity back then for ownership with a start-up brand. We felt it would be best to learn the industry through the Ciroc partnership and work our hardest. We literally saw it as a paid internship, a paying opportunity to learn through one of the biggest in the form of Diageo. So as it turns out this entire process was leading to Billiato and has been in the works for nearly 6 years. 

How much has being a father influenced how you do business and how you manoeuvre around the industry these past few years?

It’s opened my thinking so much more. I’m always conscious of the fact that all of this is more than just about myself. My son is literally my life, his biggest influence on me regarding the industry is more self-awareness and self-care. This game will eat you up if you aren’t deliberate about self-care, and my son is my constant reminder to take care of myself. 

When you were first coming up in the game, did you plan to be involved in this many diverse businesses and to achieve success as an entrepreneur too?

Absolutely always been the plan. I’ve been selling and doing business since before I was successful. From owning my label and releasing my own music, to building my merch from scratch and making my own tours and shows. This current rollout of businesses is a step towards the few other major deals I’m about to close off. My role models are Kanye and Jay- Z and those are business people. So I’ve always had that in mind to diversify. It also makes you comfortable when you’re making money elsewhere. I’m not forced to put out a song because I’m making money elsewhere. So the day I feel like it and I’m inspired I get into studio according to how I feel, not because I need to go and make money. 

While the Slik Talk fight was hugely popular, there was a bit of criticism about the production value — the commentary, the refereeing, the camera work. Can fans expect a better production this time around?

You’re too kind via “a bit of criticism”. We are definitely providing way better quality. Stay put for our big broadcast platform announcement. First fight was a big learning experience for myself and the entire team and we are well prepared for this next one. 

The Cassper Nyovest and NaakMusiQ fight will take place this weekend as part of Celeb City, a series of gigs running at Sun City from April 8 to April 11, 2022. For tickets visit webtickets.co.za

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