The Diary of a CEOJaackmaate: The Untold Story Of My Battle With Health Anxiety & OCD | E127
CHAPTERS
- 4:20 – 10:40
Comedy, Parents And The Birth Of A YouTuber
Jack links Jimmy Carr’s idea that comedians try to please a parent to his own childhood, detailing a fraught relationship with his alcoholic mother and unwavering support from his dad. He explains how getting kicked out and living in a tiny box room forced him to take YouTube seriously, symbolized by buying a whiteboard and treating content like a job.
- •Jimmy Carr’s notion that comedians are trying to please a parent resonates with Jack.
- •Difficult relationship with his mum, who didn’t understand or respect YouTube and struggled with alcohol.
- •Supportive dad who believed in YouTube’s potential and defended Jack’s choices, like buying clothes for videos.
- •Being kicked out at 18–19 and living at his uncle’s in poor conditions became a turning point.
- •Buying a whiteboard, planning uploads, and saying yes to every opportunity in 2012 shifted YouTube from hobby to career.
- 10:40 – 35:40
Family Breakdown, Boundaries And Choosing Distance From His Mother
Jack and Steven compare their unconventional mothers and discuss the difficulty of setting boundaries with problematic parents. Jack recounts his parents’ turbulent relationship, his father’s eventual departure, and his choice to effectively cut his mum out for his own mental health, despite guilt and occasional contact.
- •Steven shares his own challenging mother; Jack relates and notes he’s barely seen his mum for 8–9 years.
- •Jack’s mum texts late at night when drunk; he wants messages at 10:30am Tuesday, not 11:30pm Saturday.
- •He debates when, or if, to draw a line under past harm and reconcile.
- •Jack’s dad was repeatedly kicked out unfairly; Jack witnessed his dad writing love notes that were ignored.
- •When his dad finally left after the 2006 World Cup final, Jack almost felt relief and supported him “flying.”
- •He maintains a close, safe relationship with his nan, contrasting with his mum’s unresolved issues.
- 35:40 – 52:40
School Years, Class Clown Identity And Early Shame
Jack reflects on being a short, ginger kid seeking acceptance through humor and disruption. He admits to regretting his behavior toward teachers, especially one he’d like to apologize to, and connects his class clown persona with learning to pre‑empt bullying through self-deprecation.
- •Sought acceptance from ‘cool kids’ by acting out and chasing laughs.
- •One big laugh (putting a ruler in a fan) hooked him on being the class clown.
- •He regrets being a “bit of a prick” to teachers, particularly Ms Chapman, and wishes to apologize.
- •Used self-deprecating humor about being ginger to disarm others and gain control.
- •Early home issues (mysterious facial marks blamed on a non-existent cat, beloved ornaments smashed) bled into school stress.
- •Academically capable and predicted top grades but underachieved due to lack of seriousness and focus on attention.
- 52:40 – 1:46:40
Inherited Traits, Anger Management And The ‘Anti‑YouTuber’ Persona
Jack examines how he consciously rejected his mum’s traits but inherited his dad’s temper, which he channels into trivial frustrations rather than violence. He then explains how his online ‘angry commentator’ persona evolved—from authentic annoyance to a fake, profit-driven performance that increasingly conflicted with who he really is.
- •He and his sister actively monitor themselves for echoes of their parents’ worst traits.
- •Jack shares his dad’s tendency to anger but mostly over trivial triggers (editing software crashing), which Fiona helps him regulate.
- •He did anger management at school (for an incident he says he didn’t commit) but acknowledges it probably helped.
- •As the ‘anti‑YouTuber’, he built a brand on slagging off other creators, often performing exaggerated anger for views.
- •He differentiates videos with a clear comedic ‘why’ (e.g., Zoella advent calendar) from ones driven purely by jealousy, clout, or money (e.g., KSI medication rant).
- •Awareness that his audience expected outrage made him feel trapped in a character he no longer believed in.
- 1:46:40 – 1:58:00
Trolls, Twitter And The Ego Trap Of Online Conflict
Jack and Steven analyze Jack’s habit of engaging with trolls and football Twitter, often from bed, despite knowing it’s emotionally draining. They discuss how Jack’s own abrasive comedic style trains his audience to speak to him that way, and how boredom, ego, and identity all fuel his online back‑and‑forths.
- •Jack frequently claps back at negative comments, then later deletes responses after Fiona persuades him.
- •He acknowledges that many trolls “are in my head,” and that part of him enjoys the rush of the argument.
- •Steven points out Jack’s young, laddish audience use the same language he uses (e.g., ‘two bellends’), sometimes blurring banter and insult.
- •Jack recounts fans greeting him at meet‑and‑greets with, “Alright, you c*nt?”, mirroring his online persona back at him.
- •He’s tried deleting Twitter but always reinstalls it quickly, recognizing an addictive pattern.
- •Intellectually accepts he’d be happier disengaging more, but emotionally and egotistically struggles to let go.
- 1:58:00 – 2:09:00
Money, Arrival Fallacy And The Illusion Of The Finish Line
After years of grinding YouTube with little financial reward, Jack suddenly began earning serious money and focused on buying a house outright. Achieving that goal brought not joy but an unsettling emptiness, prompting a deeper conversation with Steven about why humans are wired for struggle and ongoing purpose rather than static comfort.
- •Jack did YouTube seven years without pay; the post‑Zoella income surge felt no more fun than the free era.
- •He single‑mindedly saved to buy a house; once he bought it in May and moved in September, his desire to upload collapsed.
- •Wandering the house drunk, he realized the ‘arrival’ felt meaningless compared to earlier milestones and hustle.
- •Steven frames this as “arrival fallacy” and “epidemic of purposelessness,” especially among men, linked to declining life expectancy.
- •Jack still believes money buys freedom (and thus happiness) but learned it doesn’t guarantee direction.
- •His deepest satisfaction comes from using money to help family—grandad’s £5k, sister’s diabetes tech, dog’s ashes—rather than material purchases.
- 2:09:00 – 2:20:20
Losing Motivation For The Main Channel And Authenticity vs Audience Expectation
Steven probes why Jack effectively abandoned a 1.4M‑subscriber main channel, which many would see as a dream asset. Jack explains that the channel had become synonymous with inauthentic call‑outs, and he only now uses it when he truly cares about a topic, like Boris Johnson, aligning output with genuine motivation rather than algorithmic pressure.
- •Jack rejects the framing of ‘can’t be arsed’; it’s more that the content style no longer reflects who he is.
- •Inbox requests to attack obscure creators over minor issues made him realize his brand had drifted into policing for sport.
- •He still occasionally uploads when there’s a real ‘why’—e.g., his fast reaction video on Boris Johnson that went viral and hit newspapers.
- •He compares wearing an inauthentic persona to a heavy mask that eventually must be discarded to protect mental health.
- •Past filming sessions where he ranted on autopilot for ad revenue, then couldn’t recall what he’d said, convinced him he had to change.
- •Current philosophy: main channel only when there’s a clear purpose and authentic emotional investment.
- 2:20:20 – 2:31:00
Class Guilt, Imposter Feelings And Redefining Deserved Success
Jack struggles to reconcile his relatively ‘easy’ earnings with the hard graft of people around him, leading to guilt and imposter syndrome. A stark encounter in a club with a cancer ward worker highlights the disparity, pushing Jack to reframe deservingness around impact, opportunities created, and generosity rather than sheer effort.
- •Watching his dad work 12-hour factory shifts yet struggle financially makes Jack feel guilty about his income from online content.
- •In a club, he compares his earnings to a cancer ward worker making 10% of his, which deeply unsettles him.
- •He’s conflicted: he won’t give all his money away but channels much of it to family support.
- •He links some guilt to seeing entitled YouTubers and not wanting to become like them.
- •Acknowledges he has a talent for being personable and making people laugh but struggles to fully accept he ‘deserves’ his level of success.
- •Counters this by highlighting how his success has lifted others—Stevie leaving Boots to co‑host Happy Hour, Fiona leaving retail to edit, etc.
- 2:31:00 – 2:46:40
Happy Hour, Spotify And A More Authentic Creative Path
Jack recounts the genesis of the Happy Hour podcast, from a drama-focused show with ImAllexx to a guest-led interview format that rekindled his love for content. He discusses taking a Spotify exclusive deal for financial reasons, then discovering unexpected upsides like high‑profile guests and a more sustainable, values-aligned future.
- •Always wanted to interview people; studied interview techniques at college and first interviewed his grandad.
- •Initial 2017 podcast fizzled due to logistical issues at YouTube Space; Happy Hour launched in 2018 with friend Stevie as the ‘everyman’ co‑host.
- •Early episodes with ImAllexx mimicked toxic YouTube drama culture; Jack dropped that approach as “poisonous” and pivoted to real conversations.
- •Ricky Gervais appearing early validated the show and opened doors to other guests.
- •Spotify exclusivity was initially a money-driven decision; he anticipated backlash from removing full video from YouTube.
- •Over time, benefits emerged: Spotify now books major guests (Johnny Knoxville, Rob Brydon, Russell Howard) and offers video options, while YouTube clips still monetize and act as promotion.
- •Jack’s vision includes live tours and maybe a more formal chat show, but primarily he just wants to keep doing conversations he loves.
- 2:46:40 – 3:07:20
Health Anxiety, OCD And Living With Constant Fear Of Illness
Jack offers a raw look into his health anxiety and OCD, describing obsessive cancer fears, avoidance of medical checks, and intricate rituals he once believed kept loved ones safe. He acknowledges the irrationality yet feels trapped, too scared to seek medical confirmation and relying instead on self-help workbooks and music that articulates similar struggles.
- •Health anxiety rooted in finding a testicular lump at 13 and fearing cancer; doctor called it a cyst, but fear persisted.
- •Now avoids touching or looking at that area, and any cancer-related advert triggers intense distress.
- •Estimates 15–20 daily episodes where his brain insists he already has cancer, not just a risk.
- •Historical OCD rituals include kissing a photo of his grandad 13 times and mentally repeating prayers in perfect order, with do‑overs if ‘wrong.’
- •Explains OCD ‘waves’ using a weed high analogy—moments of dissociation then sudden awareness, but filled with cancer thoughts.
- •Recommends rapper NF’s music for others with OCD/health anxiety, saying the metaphor of “black balloons” mirrors his inner experience.
- •Openly admits he tells others to seek help but is personally too afraid of diagnosis to see doctors, highlighting the disorder’s hold.
- 3:07:20 – 3:27:40
Alcohol, Sleepless Nights And Obsessing Over Sunrise
The conversation turns to how Jack uses alcohol and strange time-based rituals to manage his anxiety, particularly at night. He candidly parallels Steven’s business partner Dom’s patterns, describing his own habit of drinking alone until sunrise to avoid being alone with intrusive thoughts, and compulsively tracking sunrise times and clock digits.
- •Jack often continues drinking after nights out to prolong the period without intrusive thoughts, mirroring self-medication.
- •He experiences “hangxiety” where post‑drinking days magnify OCD and dread.
- •He fears bedtime because that’s when cancer thoughts intensify; sunrise becomes a dreaded deadline symbolizing another day starting with no sleep.
- •Obsesses over sunrise times and has a compulsion to turn his phone off on exact quarter hours (e.g., must see 04:00 or 04:15).
- •Admits being in a recurring pattern of 2–3 hours of sleep for several nights until exhaustion forces a reset.
- •Despite these struggles, he insists he’s fundamentally happy, underscoring the complexity of living with chronic anxiety.
- 3:27:40 – 3:49:40
Love, Fiona’s Support And The Question Of Fatherhood
Jack speaks movingly about his partner Fiona, describing her as his backbone who now manages anxiety better than he does. He shares how she quietly orchestrated logistics to ensure he fulfilled a West Ham gig when he wanted to bail, and then grapples with the idea of becoming a father amid fears about sacrificing his current lifestyle.
- •Fiona was initially the anxious one with panic attacks; over time their roles reversed and she now anchors him.
- •She listens to his spirals late into the night, rarely drinks, and gently pushes him through avoidance (e.g., packing his bag, booking hotels).
- •Their families differ: her family talk and connect deeply at Christmas; his watch TV—she’s brought more emotional openness into his life.
- •Jack feels he’d be a great dad but keeps moving the goalposts (first 25, then 27, now “by 30”), fearing sacrifice of freedom and career focus.
- •He doesn’t want to be an older dad but also doesn’t want to give up what he loves doing right now.
- •Steven relates with his own partner’s stabilizing influence and similar ambivalence about timing children.
- 3:49:40
Talent, Stand-Up Dreams And Feeling Content At Last
In the closing section, Steven presses Jack to own his talent and consider stand‑up more seriously. Jack recounts opening for Max Fosh and feeling, for the first time, completely in his element on stage. He ends by describing himself as “content” rather than fully happy, acknowledging remaining issues but also deep gratitude for where he is.
- •Jack identifies his core talent as being able to talk to anyone—from KSI to Deborah Meaden—and get a laugh by meeting them at their level.
- •Steven insists Jack’s presenting and podcasting skills are rare and under‑credited by Jack himself.
- •Jack describes near‑panic before opening for Max Fosh, jokes written on his hand, then a sudden click once on stage: timing, pauses, crowd control.
- •The rush of live laughter felt like what he’s “meant to be doing”; he now wants to pursue both Happy Hour live shows and solo stand‑up.
- •Steven likens live shows (e.g., his Palladium dates) to feeling most alive, reinforcing Jack’s instinct toward real‑world performance.
- •Responding to Israel Adesanya’s question “How are you truly feeling?”, Jack answers: “Content…privileged to be where I am,” signaling a fragile but hard‑won equilibrium.
