Khalil Osiris is a man who’s walked through fire. After spending a gruelling 20 years in prison, he emerged transformed and hungry to make an impact. Having earned his bachelor’s and master’s degrees while behind bars, he went on to become a respected educator, speaker, and justice reform advocate—working across the U.S. to help formerly incarcerated men reintegrate into society, find employment, and rediscover their purpose.

Khalil and I have known each other a long time. We’ve walked different paths, but always shared a deep commitment to truth, redemption, and calling men to live with strength and integrity. In this conversation, we tackle some of the pressing issues of our time—race, cancel culture, virtue signaling, tribalism, and the labels that so often divide us. But more than that, we explore the power of owning your story, breaking free from the past and stepping into a life of purpose.

This isn't about pointing fingers or stirring controversy. It's about honest dialogue, grounded in grace and our shared humanity. It's about finding common ground and building bridges in a world that desperately needs them. Join us as we discuss accountability, masculinity, brotherhood, and the transformative power of redemption. Discover what it means to live with conviction, courage and hope.

Craig sits down with men’s mental health crusader and TRC veteran Thulani Grenville-Grey to explore one of the most important and overlooked issues in society today: the emotional struggle that so many men carry in silence.

Having both worked extensively with men across South Africa, Craig and Thulani unpack why men find it so hard to ask for help, why so many suffer in silence, and what lies beneath their reluctance to express pain and vulnerability. They also share their unique insights and moving stories from the front lines of helping men heal and reconnect with their true selves.

This frank and sometimes uncomfortable conversation offers a rare glimpse into the male psyche - how early experiences shape identity, how cultural expectations suppress emotion, and how unspoken pain often drives destructive behaviour. It’s a raw and deeply human look at what it means to be a man - and how healing, vulnerability and true brotherhood can change everything. If you’re a man, or love a man, you need to hear this.

In this episode, Craig takes a brutally honest look at a fictional series that’s hit a nerve across the globe - 'Adolescence'. What unfolds in the story is tragic, but what it reveals about the world our boys are growing up in is even more alarming. This isn’t about blaming masculinity. It’s about understanding what goes wrong when we don't guide it, nurture it, and validate it. Join Craig in uncovering the deeper truth behind the headlines - because it’s only by confronting it that we can raise the kind of men this world desperately needs.

In this raw and honest conversation, former pro footballer Silver Shabalala opens up about his journey from the streets of Soweto to the national spotlight - and the personal cost that came with it. From sudden fame and fast money to fathering nine children and falling into the traps that destroy so many men, Silver shares his story with rare vulnerability and courage - revealing the hard truths about life, manhood and fame he wishes someone had told him when he was young.

Now, driven by the absence of mentors in his own life and a deep desire to help others avoid the same pitfalls, Silver is actively engaged in mentoring men across South Africa - guiding them through the challenges of masculinity, identity and success.

This eye-opening episode uncovers the four big lies young men grow up believing - about sex, power, success, and what it truly means to be a man - and unpacks a more authentic, life-giving vision of masculinity rooted in truth, brotherhood and accountability. This isn’t just a story about football. It’s about falling, rising, and finding purpose in pain. If you’re tired of false masculinity and ready for something real, this conversation will hit home.

A father’s love is one of the most powerful forces in a daughter’s life. It shapes her confidence, her sense of worth, and the way she sees the world. In this episode, I have the joy and privilege of talking with my own daughter, Blythe, about our personal father-daughter journey. In this unscripted, authentic conversation we unpack the lessons learned, the mistakes made, navigating the pain of divorce and the moments that have meant the most to each of us. It’s the story of a sacred romance. If you’re a dad, this episode will challenge and inspire you to be even more intentional in the way you love, lead, and support your daughter.

We often hear about the importance of human rights, but what about the responsibilities that make them possible? In this episode, we take a deep dive into the often-overlooked truth: rights and responsibilities go hand in hand. You cannot have one without the other. From history’s greatest struggles for equality to modern-day challenges, we examine how fulfilling our duties to others is the key to protecting the freedoms we cherish. Are we holding up our end of the deal? Tune in for a compelling conversation that challenges the way we think about rights, freedom, and accountability.

What happens when a woman dares to step into a world dominated by men? Asnath Mahapa, South Africa’s first Black female commercial pilot, has spent decades defying expectations and shattering stereotypes. In this powerful episode, she opens up about the relentless obstacles she’s faced—from sexism and racism to self-doubt—and how she overcame them with resilience, grace, and an unshakable belief in herself.

Asnath has not only broken barriers in aviation but has also blazed a trail for other women, empowering future generations to rise. In honour of International Women’s Month, we celebrate her incredible strides toward gender equality and women’s empowerment. We also dive into the harsh realities of systemic bias, the power of perseverance, and why the fight for true equality is far from over.

If you’ve ever been told “you don’t belong,” this conversation is for you. Asnath’s story will leave you inspired, fired up, and ready to take up your own space in the world.

60% of South African children grow up without a father. 10,000 babies are abandoned every year. But what if men chose to show up? In this episode, I sit down with Sihle Mooi, a passionate advocate for fatherhood and men’s development who leads ‘Hotel Hope’, a home providing love and care for abandoned children. We dive deep into the power of masculinity, the crisis of fatherlessness, and how men can step into their role as protectors, mentors, and nurturers.

This conversation isn’t just for dads—it’s for every man who wants to make a difference. If you’ve ever questioned the role of men in society, this episode will change the way you see fatherhood, masculinity, and your own power to bring change.

The real heroes in life aren’t the ones on stages and platforms receiving awards and recognition, fame and fortune. The real heroes are everyday men and women doing their bit to make the world a better place, sometimes in the humblest of circumstances.

Join me as I chat to one of these everyday heroes, Tapson Moyo. I was blown away by the wisdom of this ‘humble philosopher’ and I’m sure you will be too. His reflections on life, work, fatherhood, conscious choices and staying positive are guaranteed to inspire.

We are all of equal value, and this episode is an invitation to honour and acknowledge the hidden heroes among us.

Are you addicted and don’t even know it? Addiction isn’t just about drugs and alcohol—it’s anything that controls you. In this powerful conversation, Craig Wilkinson sits down with Conrad Cooper, one of South Africa’s leading experts on addiction recovery, to expose the hidden addictions that are destroying lives.

From pornography, social media, and gaming to workaholism and gambling, we uncover how addiction is actually a behaviour disorder—driven by deep emotional wounds, trauma, and a need for connection.

💡 In this episode, you’ll discover:

✔️ The #1 reason people stay addicted (it’s NOT what you think!)

✔️ How porn addiction rewires your brain—worse than heroin

✔️ The "90% of addiction" you never see

✔️ Why most addicts don’t know they’re addicted

✔️ The simple test to check if you’re addicted

🚨 If you or someone you know is struggling with addiction, there is HOPE. Recovery is possible. Freedom is possible. It starts with awareness.

🔔 Subscribe for more powerful conversations on breaking free from addiction and living a life of purpose.