Jason Wilson, best-selling author & Martial Arts Master, speaks on men hiding behind a mask, healing trauma, redefining masculinity, discipline as a tool,  Mental Health, Martial Arts, emotional freedom, family values and why vulnerability is real power artwork

Jason Wilson, best-selling author & Martial Arts Master, speaks on men hiding behind a mask, healing trauma, redefining masculinity, discipline as a tool, Mental Health, Martial Arts, emotional freedom, family values and why vulnerability is real power

Pivot Podcast

May 29, 2026

“Men put a mask to hide what appears to be weak to the world.
Speakers: Channing, Freddie T, Jason Wilson, RC
**SPEAKER_1** (0:00)
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**Channing** (0:30)
As we close out Mental Health Awareness Month, we wanted to have a conversation that went deeper than social media captions. Today, we sit down with Jason Wilson. He's made it his life's mission to help young boys and men confront the pain they were taught to suppress. Jason founded the Cave of a Doolum Transformational Training Academy. It's an organization that helps mentor young men through discipline, emotional intelligence, accountability, and healing. Many of you have seen the powerful viral clips, but behind those clips is a man whose message was built through struggle, loss, reflection, and transformation. We talked about the death of his mother and the grief that reshaped his life. We discussed trauma, emotional suppression, and how unresolved pain can spill into relationships, anger, or even domestic violence. But instead of avoiding accountability, he leans into it, speaking openly about his growth, about ownership, and the difficult work required to become a better man. We also unpack something our culture constantly confuses, masculinity versus true manhood, and even how that saved his son's life. There's also a deeply personal moment for Jason and I where he apologizes. It was rooted in reflection and humility and grace, and honestly, it became one of the clearest examples of what healthy manhood can actually look like in real time. This episode is emotional, at some points uncomfortable, but it's honest. And these are the conversations that we need more of, especially at the end of Mental Health Awareness Month. This one was long overdue, so please welcome Jason Wilson to The Pivot as he sits down for a pivotal conversation with me, Chan, and Freddie T.
I got some questions.

**Freddie T** (2:46)
We know you do, we know you do.

**Channing** (2:48)
We get an opportunity to have a ton of conversations on this show, but to have Jason Wilson here, bestselling author, and the work you're doing with the union, along with your wife, I don't want to forget her, but every day continuing to inspire. And it's one of those things, you've been doing this work for decades before I finally saw the viral video, and you start to think to yourself, you know, it's like, what are they doing at the cave that is transforming these boys, that this man had so much patience with this young man going through what he was going through. And so I just want to say thank you for all that you're putting out in the world and giving us this opportunity. Flying here, actually, I was watching Batman, and Bane was talking, and he said, nobody cared about me before I put on the mask.
And it was a superhero villain thing, but when I listened to that, I feel like so many men feel like they have to put on a mask in order to be cared about or in order to be thought of as valuable. Why do you think so many men struggle, Jason, with having the ability to open up and show the world who they truly are?

**Jason Wilson** (4:01)
Well, first and foremost, I believe that the facade, the mask you're speaking about is not, we don't put that mask on for people to care about us. We put that mask on to hide what appears to be weak to the world, appears to be a failure, appears to be wounded to the world. And so it starts from childhood. We're told when we're young, big boys don't cry. And then when you become a man, no pain, no gain. So there's no escape from the façade. And men today are crying out just wanting to be human. And I was watching on social media earlier, and I saw a clip from Dana White.
And I was really surprised to hear him say that men's mental health is BS.
Considering that we have, what is it, 17.5 veterans who take their lives every day, considering that men die by suicide almost four times as likely as women, considering that over 70% of violent crimes are by us men.
And to...
It was, to me, it was irresponsible, because I have to look in the eyes of men and young boys who are battling, should I be a human or do I just appear to stay strong?

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