Yusuf Stevens, the luminary media entrepreneur, stands as the illustrious founder and CEO of Cheeky Media & Cheeky Pictures, a maestro navigating the diverse realms of the media landscape.

Adorned with multiple accolades, Yusuf has been at the helm of Cheeky Media since its inception, deftly transforming it into a multimillion-dollar powerhouse.

In the dazzling tapestry of his achievements, Cheeky Media has birthed acclaimed productions like Real Talk With Anele, The Man Cave, Wingin’ It, She’s The One, Biting About, and Jou Ma Se Chef.

entrepreneurship, money matters, media — Yusuf Stevens, Image: Supplied

Yusuf himself is a beacon of success, earning a spot in Forbes' Top 30 under 30 and Destiny Man's top 40 under 40, a feat accomplished at the age of 29.

As the orchestrator of the enchanting live breakfast show, The Morning Show, Yusuf's creative genius extends to crafting some of South Africa's biggest shows, with international acclaim following suit.

The inception of Cheeky Studios in 2022 marked a new chapter, culminating in the production of an international feature film (slated for the last quarter of 2023) and a lucrative multi-movie deal, positioning Cheeky Studios as a titan in African cinema.

Yusuf's academic prowess is anchored in a BComm (Finance and Economics) from the University of Stellenbosch, while his lifelong dream of holding a PPL (H) adds a touch of aviation mystique to his persona.

Beyond the executive realm, Yusuf is a stalwart board member of The Anti Agency (Pty) Ltd, The Exponential Company (Pty) Ltd, B&B Media (Pty) Ltd, Generosity Digital, and Love Your Ears, illustrating his commitment to multifaceted impact.

As a distinguished media expert, Yusuf has graced numerous platforms, including SABC, ETV, and 702 Radio, while also contributing to the industry's inclusivity through mentorship programs at Cheeky Media.

entrepreneurship, money matters, media — Yusuf Stevens, Image: Supplied

Honored as a Leader of Influence at the 2023 SA Heroes Awards, his commitment to excellence extends to familial roles, being a proud husband and father to three young boys, his driving force.

Yusuf, cognizant of the void left by the death of his own father, is fervently dedicated to being present and setting high standards.

Beyond creating jobs as a CEO, he endeavors to shape a legacy of gentlemen through his example. In his pursuit of a global media empire, Yusuf values impact over financial gains, echoing his belief that true success is relative, urging others to dream big and work tirelessly.

"Success is relative. Don’t let anyone be the judge of your intentions or accomplishments. Your biggest competitor will always, only, be you," says the media mogul.

In the grand symphony of Yusuf's life, this refrain resonates as a testament to his indomitable spirit and unwavering commitment to a legacy of influence.

GQ South Africa caught up with Yusuf to chat about his media empire and everything in between.

GQ: Briefly tell us what makes you the person you are today?

Yusuf Stevens (YS): The best way to describe who I am is a Father trying to lead his sons to a better future, a Husband trying his best to ensure the happiness and stability of his wife & family, a businessman trying to ensure that the company he runs creates opportunities for people he wish he had and a Human trying to leave the world in a better state than when he came into it.

GQ: What made you get into the media space, was there an influential person on your path?

YS: Sheer fluke. I entered the media space when I filled the role of a receptionist at a production company temporarily. This opportunity afforded me exposure to TV production where I learnt things from the ground up.

GQ: What are the biggest challenges you've had to face in your career and how did you get past them!?

YS: The first major challenge was when my previous employers tried to sink my business as soon as I started. The company was very reputable in the industry and tried everything possible to derail us.

Another major challenge was when one of our clients (broadcaster) stopped paying us for one of the daily live shows we were producing which created a cashflow disaster- apart from that, Covid was challenging .

entrepreneurship, money matters, media — Yusuf Stevens, Image: Supplied

I think I got through all of these challenges the same way- Put my head down and I had to get creative and come up with solutions. I think the moral of the story is each one of these challenges could have ended the business- but luckily we don’t quit easily and are willing to work 24/7 to get the job done.

GQ: What does 'vulnerability' mean to you and what role does it play in your work?

YS: This is a tough one…. I am a person who needs to have a certain level of control over scenarios- and if things are beyond my control I try my best to limit the downside of an eventuality by meticulous planning.

The thing about growing a company is that if you don’t learn to trust people within your organisation, you will never grow- you will never be able to do more of the “big” things unless you entrust people to run on their own.

Every time we take on a project I’m left vulnerable - as an example- Appointing a director on a tv show or film, leaves me vulnerable.

Trusting a producer to run with a concept comes with risk- investing in new studios or equipment can be seen as a gamble as often these investments are based off contracts which could end, projects that can be terminated.

So trusting, in itself makes me feel a little vulnerable. That said, I totally back my team and I believe we are the best at what we do.

GQ: What’s something that gets in the way of your creativity, and how do you move through it?

YS: Constant disruptions. At any given time we have about 20 different projects all requiring problem solving, input and feedback so it means constant meetings, sometimes impromptu which can cause a bit of frustration.

I try to have regular status meetings when I’m in the office as scheduled times so as to limit the impact on my schedule and create a little bit of structure in the chaos.

GQ: Describe a snapshot of a joyful moment in your life.

YS: The day I got my Helicopter pilot’s license. It was one of those days where I took the time to take it all in, enjoy the moment and the personal accomplishment of fulfilling a lifelong dream.

GQ: Do you have a mantra, manifesto, or favourite quote for living and loving with your whole heart?

YS: There’s 2 that I live by – 1 is by Muhammad Ali- "Impossible is just a big word thrown around by small men who find it easier to live in the world they've been given than to explore the power they have to change it. Impossible is not a fact.

It's an opinion. Impossible is not a declaration. It's a dare. Impossible is potential. Impossible is temporary. Impossible is nothing." The second is by Nelson Mandela- “It always seems impossible until its done”

GQ: How do you define success?

YS: Success to me is always relative and I’ve have variations of its meaning apply to me. Initially success was always attributed to financial success and I pushed really hard to become financially successful.

Today it means something completely different- Its being at peace, having time for myself and my family, its watching my kids grow, its being able to create fond memories with my family. It’s being comfortable with who I am.

GQ: Would you say personal style, health & fitness and staying well-groomed are important in relation to success?

YS: Definitely. I think it’s often underrated. We live in an interesting society, where it’s cool to be sloppy and relaxed all the time. Personally, the way I dress has a big impact on how I feel and how I feel hugely impacts my productivity.

I think taking pride in your appearance says more words than you could ever and I believe that people who make the effort in looking and feeling good generally makes a better impression- and as the saying goes, first impressions count.

I also feel like a person who works at at keeping their bodies physically strong has a mental edge over those who don’t. Healthy body, healthy mind.

GQ: What would you say is the one thing that you think and feel you are blessed with?

YS: I have a very supportive family. I can’t always be at the sports matches, or at practice, or concerts- and it does make you feel guilty. Knowing that my family understands and appreciates what I do pretty much enables what I do.

GQ: You’ve recently founded a film production company; do you mind telling us about this project?

YS: I have wanted to move into scripted content for a while and then COVID happened and it slowed me down completely. I have subsequently started “CHEEKY STUDIOS”, which is the scripted wing within Cheeky Media and we’ve just completed our first feature film.

As much as it sounds glamourous, its really not and I had to dig really deep to get this off the ground. It was like starting over in an entirely new industry. I had no real network in the space, wasn’t taken seriously in the beginning, hired a lot of people who oversold and underdelivered

But, as with every other challenge, I’ve had to learn to fly whilst falling from the sky and I’ve managed to build a team that is really clued up, wants to shake things up and believe in the vision I have.

And that is to create movies and series that are truly and proudly South African, however appeals to an international audience. To show the rest of the world what we’re capable of and to deliver world class productions and get it out for everyone to see.

GQ: What are some of the latest films you’ve worked on since launching the company two years ago?

YS: Unlike TV, it’s a little slower than that - we’ve been working on one project which is in its final stages and will be released later this year.

This is a high budget (R25m) action comedy starring, Trevor Gumbi, Jonathan Boynton Lee, Nthati Moshesh, Noxolo Dlamini, Jack Devnarain, Thulani Mtsweni, Bouwer Bosch, Stevel Marc and Nadine Theron . We do have a few others in development.

GQ: How do you see yourself playing a role in South Africa and the world at large in relation to your roles in the media landscape!

YS: I’d love to play a role in getting the industry to operate more efficiently and more globally focussed. I’ve been working with investors to create a fund that will help eradicate some of the biggest challenges the industry faces and together with a few key stakeholders, we want to create a more inclusive environment that aims to help creatives be more creative and get their stories told.

GQ: And lastly, what’s next for Yusuf?

YS: If only I knew I’m working really hard to build Cheeky Studios into a global entity and I’m making slow and steady progress. I’ve been doing this for a while now and sometimes you get tired.

I think at 37, getting tired is not an option I’m digging deep. I’m definitely working on building a more sustainable team who can run things more independently and without my direct involvement in the hopes that it can free me up to get more deals done and focus on the macro full time.