How Cassper Nyovest has harnessed his skills and became a business mogul

On Sunday night, a few hours after he’d taken to the ring and lost to Naak Musiq in their exhibition bout at Sun City's Superbowl, Cassper Nyovest was pictured smiling from to ear to ear as he danced by his table at the official Celeb City after-party.

In the video, he was sporting a pair of his signature Root of Fame 990 sneakers, a self-branded T-shirt with his face on it and drinking out of a bottle of his own liquor brand, Don Billiato.

It was an outrageous flex that showcased his unparalleled level of business smarts and ownership.

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Despite having just taken a bruising loss in front of the entire country, the 31-year-old is winning big.

The control he exerts over his own career — he owns his music, he’s constantly outfitted in his own clothing line and he drinks his own liquor brand — calls to mind American rapper Rick Ross, who is appropriately nicknamed “The Biggest Boss”.

Like Ross, who has in the past year expanded his business portfolio to include enterprises as diverse as a hot wings fast food joint and potato chips, Cassper is making money by any means necessary and, perhaps most importantly, maintaining ownership.

The journey here really began with his historic and iconic “Fill Up The Dome” concert in 2015, through which he became the first local headliner to fill up at the then 20 000-capacity Ticketpro Dome, which is now a WeBuyCars dealership.

That was the moment the country first came to a standstill in support of the ace rapper.

He followed that up with “Fill Up Orlando Stadium” a year later, an occasion which saw him double his efforts with a sold-out crowd of 40 000.

Then he set out to fill up FNB Stadium, but fell slightly short with a reported 68 000 tickets sold out of 75 000 available.

He went on to conquer Moses Mabhida and Royal Bafokeng Stadium over the following two years.

There’s this thing Cassper does, where he creates the impression that he is the most hated person in the world and everyone is out to get him.

Then, out of the blue, things will turn completely – the sponsors he says were shunning him will suddenly appear, the stadiums he is “struggling” to fill will suddenly sell out, and the industry that’s supposedly blackballing him will show up to support out of the blue. Everybody loves the underdog, Cassper knows this and he plays on this each time.

While pure boxing fans and ex-boxers debate if this past weekend’s festivities will ultimately help boxing, what is undeniable is that

Cassper has thrust the sport into the limelight, even if just temporarily, and used the platform to once again bolster his brand and make some serious coin.

Last year, Cassper took on television when he hosted SABC1’s “The Braai Show”.

While he is really funny, with a dry wit, comic timing and casual delivery that reliably creates laugh-out-loud moments on his Instagram Stories, he isn’t a very good TV host.

Yet still he drew eyeballs to his show through the wide array of A-Listers he hosted on it and his relentless punting of the show on his social media, which has huge reach. That’s what he does.

Whether it’s a new album or new business venture, he hypes it up and promotes it with such conviction and vigour that we are compelled to pay attention.

Cassper is not immune to the occasional gaffe, though.

Last month, in a social media post meant to celebrate the late Riky Rick, his caption was widely criticised for its homophobic undertones.

Sometimes his relentless sensationalism can go a step too far.

Take 2020’s lush single, “Egyptian Cotton”, for instance.

On the second verse he rapped, “I think I might let go of the Bentley, cause I don’t wanna have his (Khotso, his son) stomach go empty”. It’s a line so over-the-top that it’s laughable. His young son’s stomach is not going to go empty, and Cassper does not need to sell his Bentley to make sure of that.

Then, of course, there are his constant beefs, primarily his long-running feud with AKA, which somehow continues to pique public interest.

There’s a level of theatre to it all that seems engineered for promotional purposes: Cassper Nyovest is doing far too well to really care about silly feuds.

The strengths and weaknesses that make him so compelling are a major part of what has brought him this far and why he is likely to keep taking it further. His fearlessness and shamelessness are what make him such a marketing genius.

He recently shared how his latest endeavours in footwear and liquor are an attempt to make him the first billionaire South African rapper. At this rate, there’s no reason to doubt him.

In a recent interview with Mail & Guardian, Cassper shared an interesting perspective on his approach: “This current roll-out of businesses is a step towards the few other major deals I’m about to close off,” he said.

“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 the studio according to how I feel, not because I need to go and make money.”

Despite all these mega business moves, last year Cassper released what is statistically the biggest single of his career, “Siyathandana”.

So even though the focus is switching and he’s becoming more and more of a multi-hyphenate mogul, the music is hitting more than ever.