Jaackmaate: The Untold Story Of My Battle With Health Anxiety & OCD | E127
Steven Bartlett (host), JaackMaate (Jack Dean) (guest)
In this episode of The Diary of a CEO, featuring Steven Bartlett and JaackMaate (Jack Dean), Jaackmaate: The Untold Story Of My Battle With Health Anxiety & OCD | E127 explores jaackmaate Confronts Fame, Family Trauma, Health Anxiety And Redemption Journey In this candid conversation, YouTuber and podcaster Jack Dean (Jaackmaate) traces his journey from a chaotic childhood and early YouTube grind to financial success, creative burnout, and eventual reinvention through his Happy Hour podcast.
Jaackmaate Confronts Fame, Family Trauma, Health Anxiety And Redemption Journey
In this candid conversation, YouTuber and podcaster Jack Dean (Jaackmaate) traces his journey from a chaotic childhood and early YouTube grind to financial success, creative burnout, and eventual reinvention through his Happy Hour podcast.
He opens up about a painful relationship with his alcoholic mother, the stabilizing influence of his father and partner Fiona, and how family dysfunction shaped his need for attention, comedy, and control.
Jack describes in detail his debilitating health anxiety and OCD, his reliance on alcohol as self-medication, and the paradox of achieving his financial goals yet feeling directionless.
Throughout, he reflects with striking self-awareness on the moral cost of his old ‘call‑out’ content, his guilt around money, his evolving sense of purpose, and why honest conversation and helping others now drive him more than views or controversy.
Key Takeaways
Unresolved childhood trauma often fuels both ambition and self-sabotage.
Jack’s volatile relationship with his alcoholic mother, witnessing unfair treatment of his father, and experiencing physical marks he had to hide at school all contributed to his desperate need for external validation. ...
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Building a career around outrage or inauthentic anger is unsustainable.
Jack admits many of his commentary/call‑out videos were driven less by genuine conviction and more by views, money and audience expectation. ...
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Reaching a big external goal often triggers a loss of purpose rather than lasting happiness.
After years of saving with a singular focus on buying a house outright, Jack finally did it—and almost immediately lost motivation to upload to his main channel. ...
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Health anxiety and OCD can be pervasive, irrational, and hard to treat when avoidance takes over.
Triggered by finding a lump in his teens and fearing cancer, Jack now estimates he convinces himself he has cancer 15–20 times a day. ...
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Alcohol can function as a powerful but dangerous form of self-medication.
Jack describes nights where he continues drinking long after others stop, not for fun but to keep intrusive thoughts at bay. ...
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Supportive relationships can be a critical counterweight to mental health struggles.
Jack credits his dad with believing in his YouTube potential early and providing moral grounding, from defending his choice to buy T-shirts for videos to teaching him to avoid physical fights after serving time for manslaughter. ...
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Honest self-reflection can transform guilt and imposter syndrome into more ethical ambition.
Coming from a working-class background and seeing relatives graft physically demanding jobs for little pay, Jack feels guilty earning large sums by talking online—especially when meeting people like a cancer ward worker earning a fraction of his income. ...
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Notable Quotes
“You can only do that for so long before you just hate yourself.”
— Jack Dean (Jaackmaate)
“If it weren’t for my mum, I wouldn’t have bought that whiteboard.”
— Jack Dean (Jaackmaate)
“There’s probably 15 to 20 times a day where I actually convince myself that I have cancer.”
— Jack Dean (Jaackmaate)
“I did YouTube for seven years without earning a penny…and that was no more fun than when I was doing it for free.”
— Jack Dean (Jaackmaate)
“I’m never going to say I deserve this to the level I’ve got to now…but I know the people around me deserve it.”
— Jack Dean (Jaackmaate)
Questions Answered in This Episode
You describe being too terrified to see a doctor about your health anxiety; what specific changes in your life or mindset do you think would need to happen before you’d actually book that appointment?
In this candid conversation, YouTuber and podcaster Jack Dean (Jaackmaate) traces his journey from a chaotic childhood and early YouTube grind to financial success, creative burnout, and eventual reinvention through his Happy Hour podcast.
Get the full analysis with uListen AI
Looking back at your series of Zoella and KSI videos, is there one moment or line you now feel crossed from justified satire into bullying, and how would you handle that same situation differently today?
He opens up about a painful relationship with his alcoholic mother, the stabilizing influence of his father and partner Fiona, and how family dysfunction shaped his need for attention, comedy, and control.
Get the full analysis with uListen AI
You spoke about the emptiness after buying your house outright; if you could redesign your goals now to avoid that ‘arrival fallacy’, what would a healthier set of personal and creative milestones look like?
Jack describes in detail his debilitating health anxiety and OCD, his reliance on alcohol as self-medication, and the paradox of achieving his financial goals yet feeling directionless.
Get the full analysis with uListen AI
Given how much guilt you feel about money, would you ever consider channeling that into a structured project—like a foundation, mentoring scheme, or content series—specifically supporting people like your grandad or that cancer ward worker?
Throughout, he reflects with striking self-awareness on the moral cost of his old ‘call‑out’ content, his guilt around money, his evolving sense of purpose, and why honest conversation and helping others now drive him more than views or controversy.
Get the full analysis with uListen AI
You said stand‑up felt like what you’re meant to be doing; what concrete steps are you taking (or avoiding) to turn that feeling into a full show or tour, and what scares you most about fully committing to that path?
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Transcript Preview
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People know Jack Mate for being the guy to slag stuff off, and that's funny. And then when the content dried up, well, I've now got to go and look for someone who's doing something wrong. You can only do that for so long before you just hate yourself. Didn't really get on w- with my mum. She would do and say things that I don't think any mum should really do. Things would happen at home and I'd have, like, a mark on my face, like, from someone that shouldn't have given me that mark. I made a video reacting to Zoella's advent calendar. That changed the game for me. The, the upload before that, I was gonna quit. I struggle with, um, health anxiety and OCD. There's probably 15 to 20 times a day where I actually convince myself that I have cancer.
So you're too fearful to go and get a health check done?
If I go there and the doctor's like, "Yeah, you're ill," then that's the end for me.
What do you mean that's the end for you? Jack, give me the, uh, give me the context on your life. You know, I, I sat here yesterday with Israel Ad- Adesanya and he told me about his childhood. Um, and there was hints of that that really kind of felt similar to the experience that I read you've had as, as a young man as well. And then also, I think, the other one where I could see real distinct similarities, and I think you might have listened to this podcast, is Jimmy Carr.
Yeah. Yeah, what a man.
Yeah, what a man, right?
Yeah.
He's like a... I didn't realize he was s- he was gonna be such a philosopher. One of the things he said to me was, you know, when someone t- becomes a comedic figure, which I consider you to be in many respects, I think you are.
Mm-hmm. I'll take that.
Yeah, good. Okay.
I'll take that.
Um, he, he says that instead of asking... 'Cause there's, you know, there's this kinda stereotype that the person themselves is struggling with something and they're trying to make other people laugh. He said to me, as you might have heard, he said, "You've actually got to ask them which one of their parents they were trying to please or to, to make happy." Does that resonate with you at all?
Um, yeah. I mean, upbringing, didn't really get on w- with my mum. I don't think she truly understood the potential in YouTube, whereas my dad always did. So when I was sort of like, like, we're... I guess, how old are you, Steve?
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