The Diary of a CEOSimon Cowell: Losing My Parents Reset Every Priority I Had
Cowell traces his rise from bored kid to record mogul, then a near-fatal back break; depression and son Eric reset his career, plus One Direction regrets.
CHAPTERS
- 0:00 – 2:30
Introduction, Subscriber Raffle, and Setting the Stage
Stephen Bartlett tees up Simon Cowell as a transformative figure in music and TV, briefly mentions the channel’s subscriber raffle offer, and frames the conversation as an attempt to understand the deeper forces that shaped the public persona everyone knows.
- •Show hits six million subscribers; launch of a special raffle for audience engagement.
- •Prizes include a £1,000 voucher, behind‑the‑scenes studio visit, and a 10‑minute call with Stephen.
- •Stephen introduces Simon Cowell as someone who has changed TV and music, hinting at both his success and his private struggles.
- •Initial teaser clips hint at topics: devastating loss, workaholism, depression, and regrets about One Direction.
- 2:30 – 12:30
Happy But Restless Childhood and Parents’ Influence
Cowell reflects on a happy yet boredom‑filled childhood, early hustling for pocket money, and the powerful moral framework his parents instilled in him—particularly respect, manners, and making others feel important.
- •Bored and disengaged at school; determined early to create a fun, interesting life.
- •Started earning as a child by washing cars and mowing lawns to fund holiday spending money.
- •Mother Julie as disciplinarian; introduced the phrase ‘manners maketh the man’ which became a lifelong anchor.
- •Father Eric offered specific, memorable advice, including the ‘sign on everyone’s head: make me feel important’ metaphor.
- •Simon consciously notices and acknowledges everyone in a room, from door‑openers to camera operators—directly tied to his parents’ teachings.
- •He now passes the same ‘manners maketh the man’ mantra on to his son, Eric.
- 12:30 – 25:00
Rejecting Corporate Paths and Entering Entertainment
Cowell explains how his father’s experience of being discarded by a big corporation convinced him to work for himself, recounting failed starts at Tesco, the civil service, and estate agency before landing as a runner in film and then in EMI’s post room.
- •Father warns him never to rely on a big corporation; they dropped his dad at retirement with no lasting care.
- •Simon fails exams twice; university is off the table.
- •Brief, disastrous job interviews at Tesco and civil service; recoils from rigid career ladders and snobbery.
- •Short but formative stint as a runner at Elstree Studios; sees a ladder to directing but loses contract.
- •Turns down an assistant job on The Shining after seeing film work’s insecurity and queue‑based hiring.
- •Mother secures an interview at EMI’s music publishing post room, which becomes his way into the music business.
- 25:00 – 42:30
From Mailroom to Song Plugger and First Failed Company
In EMI’s post room, Cowell weaponises curiosity and persistence to learn the business, secure a promotion into the international department, then leap prematurely into co‑founding a music publishing company that eventually fails in an NCP car park.
- •Post room is literally a basement/garage space; Simon makes £18 a week.
- •He knocks daily on executives’ doors asking for a better job and questions them about publishing and catalogues.
- •Exposure to royalty cheques (e.g., Kate Bush) reveals the financial upside of successful music writing.
- •After 18 months without promotion, he quits to try estate agency but hates the culture; mother notices his unhappiness.
- •Father’s connection prompts EMI to reconsider him; he is moved into the international department as a song plugger for country music.
- •The role is resented internally; job was ‘promised’ to someone else, so colleagues freeze him out for six months.
- •He responds by locking himself in a room, listening to thousands of little‑loved country songs, then hustling covers at labels.
- •Boss suggests starting a joint company, E&S Music; Simon is 19, feels unready, but gets persuaded by outside backers.
- •The company operates out of a former toilet in an NCP car park; after 18 months, he walks away sensing it’s a dead end.
- 42:30 – 1:00:00
Starting a Record Label, So Macho, and Breaking Hits Unconventionally
Cowell transitions from failed publisher to label founder, meeting Sinitta, inventing ‘So Macho’ as a club record, and using unorthodox tactics—like stock‑holding—to engineer a Top 40 chart breakthrough despite repeated initial failures.
- •Joins a manager of Hot Gossip and negotiates £55/week to start a new label, Fanfare Records.
- •Meets Sinitta at the Embassy Club; claims he runs a label as a pickup line and ends up genuinely signing her.
- •Spots an emerging dance sound in gay clubs; conceives ‘So Macho’ and B‑side ‘Cruising’ to break via club play.
- •Backer decides to exit into book publishing and shut the label just as Simon believes he has a hit.
- •He begs for a final £5,000 – no salary – to finish the record, video, and distribution; gets a reluctant yes.
- •Refuses to learn technical production to preserve the listener’s perspective; wants to stay the consumer, not the engineer.
- •‘So Macho’ flops twice; on the third attempt he ‘holds’ orders, builds back‑orders, then ships all in one week to force a Top 40 entry.
- •Once the track squeezes into the Top 40 and gets Top of the Pops exposure, it explodes into a genuine hit.
- 1:00:00 – 1:19:00
Financial Collapse, Massive Debt, and Rebuilding with BMG
At the height of early success, Cowell overextends on shares, property, and lifestyle, ends up personally owing £500,000 to the bank, moves back in with his parents at 30, and painstakingly negotiates his way back through a new label deal at BMG.
- •Encouraged to buy company shares on credit; banks sell him the dream as shares “will go up.”
- •Buys a house, Porsche, and lives on a gold credit card without understanding compounding interest.
- •When the company collapses, he’s personally on the hook for nearly £500,000; house and car are sold and still don’t clear the debt.
- •Parents never shame him; frame it as a life lesson and welcome him home at 30.
- •He negotiates the debt down by halving the capital-plus-interest total, finds a new bank willing to refinance based on his track record.
- •Meets lawyer Tony Russell via being sued over a Wham! ‘megamix’; Tony later works for him on trust, deferring fees.
- •Tony advises that the collapse is paradoxically the best thing that’s happened; pushes Simon toward a label venture with a major.
- •Universal says no; BMG says yes with a one‑year performance caveat. Simon hits the sales targets and rebuilds his career from there.
- 1:19:00 – 1:33:00
Key Mentors, Stock Aitken Waterman, and the Power of Pop Instincts
Cowell details how relentlessly hanging around producer Pete Waterman’s chaotic studio taught him the essence of pop: great artists plus great songs, executed simply, and how this partnership produced pivotal hits like Sinitta’s ‘Toy Boy.’
- •Identifies Stock Aitken Waterman as world‑class pop writers after hearing a standout radio track.
- •Meets Pete Waterman in a scrappy studio; asks him immediately to produce Sinitta’s follow‑up and is flatly rejected.
- •Pete predicts an explosion; within months, SAW records are dominating charts across the board.
- •Simon spends a year and a half effectively loitering at their studios: making tea, sitting in on sessions, never asking for pay.
- •Eventually Pete notices: ‘Why are you always here?’ Simon answers he’s trying to learn how they do it.
- •Waterman calls later with ‘I’ve got you a hit, mate’ and plays ‘Toy Boy’, which Simon recognises as a global record.
- •Simon describes Pete’s real genius as DJ‑level audience feel, not technical production, reinforcing the importance of instinct over ego.
- 1:33:00 – 1:54:00
TV Tie-Ins, Wrestling Records, and Making ‘Noise Amongst the Noise’
At BMG, Cowell treats television and children’s properties as distribution engines, turning seemingly ridiculous ideas—wrestling albums, Power Rangers, Soldier Soldier covers—into multi‑million sellers by focusing on fanbases, not industry cool.
- •Realises success isn’t about genre purity; it’s about whatever sells a lot of records.
- •Notices WWF wrestlers selling out Wembley in 27 minutes; reasons their fans will also buy music endorsed by them.
- •Boss literally begs him on her knees not to make a wrestling album, predicting catastrophe; he proceeds anyway.
- •Collabs with Pete Waterman again; flies wrestlers like Hulk Hogan and The Undertaker to record; album becomes a massive multi‑country success.
- •A&R peers accuse him of making a mockery of the business; he counters with sales data and the fun factor.
- •Uses BMG telesales team as ‘punters’ to spot demand spikes; they tip him to a song from TV drama Soldier Soldier.
- •He relentlessly pursues Robson & Jerome, even contacting family and friends; offers £50k each just to record vocals, whether or not they release.
- •When they hear the finished track, they realise it’s a hit and fully commit; they go on to outsell Oasis and dominate UK charts for two years.
- •Takeaway: trust your gut, leverage TV for emotional context, and don’t be constrained by what’s considered ‘cool’ A&R.
- 1:54:00 – 2:10:00
Trusting Your Gut, Standing Out, and Embracing Criticism
Cowell and Bartlett discuss how to stand out creatively when many people’s ‘guts’ are wrong, why it’s vital not to be a sheep, and how Cowell has learned to ignore traditional gatekeepers and accept the risks and criticism that come with unconventional choices.
- •Cowell acknowledges many talented people are frustrated: they upload music but get nowhere.
- •He chose a ‘slightly different direction’—avoiding the herd—to avoid becoming just another A&R sheep.
- •He defines success today as ‘making noise amongst the noise,’ often by reinterpreting older songs or innovating formats.
- •He urges artists to avoid copycat covers; instead, pick songs that feel contemporary but are decades old, then radically rearrange.
- •He is unfazed by accusations of uncoolness; what matters is career, passion, and results, not elite approval.
- •He recounts realising he could never win over stuffy radio producers; rather than persuade, he engineered chart positions that forced airplay.
- •Cowell admits there’s always a thrill in risk; each new series or idea contains the possibility of failure, which keeps it exciting.
- 2:10:00 – 2:25:00
Westlife’s Rise and the Bittersweet Death of His Father
Cowell revisits discovering and signing Westlife—after initially hating an earlier lineup—and how their early success coincided with his father’s sudden death, sharply reframing how meaningful chart triumphs felt compared with familial loss.
- •Louis Walsh relentlessly pitches ‘the best band in the world’; Simon dislikes the first version and declines.
- •Three months later, Louis swaps members; the second showcase impresses Simon within 30 seconds and he offers a deal on the spot.
- •Comic twist: Louis secretly re‑introduces one original member by dyeing his hair blond so Simon doesn’t notice.
- •Westlife go on to break UK records with seven consecutive No.1 singles.
- •While at a German conference promoting the band, Simon receives news of his father’s fatal heart attack.
- •The juxtaposition of a No.1 album and paternal loss crystallises for him how meaningless chart wins feel against grief.
- •He describes an agonising flight home and admits he had assumed his parents would ‘live forever.’
- •Over time, he continues to ‘talk’ to his parents in his head for guidance, believing strongly that they’re still with him.
- 2:25:00 – 2:38:00
Losing His Mother, Workaholic Spiral, and the ‘Vampire’ Years
The death of his mother triggers Cowell’s darkest emotional period, where he becomes a nocturnal workaholic to fill an inner void, putting success ahead of health until the shock of impending fatherhood begins to pull him back.
- •Mother’s death makes the loss of both parents feel final; he describes it as ‘as bad as things could possibly be.’
- •Chart positions and show successes lose significance: ‘all the things I thought were important… none of it meant anything anymore.’
- •He responds by working through the night until 7–8am, sleeping till mid‑afternoon, and embracing a ‘vampire’ lifestyle.
- •Food becomes mostly junk; he puts on a lot of weight and functions in a fog despite external success.
- •He admits to periods where life felt so empty he wouldn’t have minded if something terrible happened—even if he didn’t actively plan self‑harm.
- •He frames this era as intensely dark and speaks about men’s mental health; he still suffers depression and is particularly hurt by disloyalty.
- •The call from Lauren—‘Are you sitting down?’—announcing she was pregnant with Eric marks the beginning of a profound emotional and lifestyle turnaround.
- 2:38:00 – 3:02:00
Eric’s Birth, Life Reordered, and Strict New Boundaries
Becoming a father to Eric radically changes Cowell’s sense of purpose, his daily structure, and his boundaries around work, technology, and sleep, shifting his number‑one priority to family while still maintaining ambition.
- •Eric’s arrival ‘made me happy again’ and restored a sense of meaning after parental loss.
- •Sharing The Jungle Book with Eric reconnects him viscerally with his own childhood joy.
- •Cowell recognises that pre‑Eric, he was dragging others through 8am finish times and weekend work, and apologises in retrospect.
- •Post‑Eric, he institutes practical boundaries: rarely works Fridays, no emails after 5:30–6pm, and largely ignores social media.
- •He has no personal mobile phone, only an in‑car US phone he barely knows how to use; prefers landlines and in‑person conversations.
- •He found he was noticeably happier during three‑to‑four‑month stretches each year when his phone was off, prompting him to abandon it entirely.
- •He argues phones are like ‘having a toaster with you all the time’—useful but deeply boring and intrusive.
- •His advice to younger workaholics: identify where ego is forcing you to persist in bad bets, accept that creativity needs rest, and recognise a four‑day focused week can outperform five exhausted days.
- 3:02:00 – 3:30:00
Accident, Pandemic, Physical Rehab, and Discovering Therapy
A severe electric bike accident during the pandemic leaves Cowell with a broken back and months of immobility, but this crisis catalyses a new commitment to physical fitness and later to psychotherapy, which he credits with reordering his priorities and reducing overthinking.
- •Electric motorbike crash breaks his back in three places; he undergoes six‑hour surgery with a metal rod inserted.
- •He signs a consent form about life support just before going under, underscoring how serious the surgery is.
- •Post‑op, once spinal pain receptors wear off, the pain becomes ‘unbelievable’; he’s heavily medicated and deliriously calling his lawyer about his will and pitching TV shows.
- •A nurse forces him into gradual walking in the garden—starting with 20 steps—like a bird pushed from the nest; he builds up to 20,000–30,000 daily steps, shredding his unprepared feet at first.
- •He believes, in hindsight, the accident was worth it because it revealed how unfit he actually was and forced a course correction.
- •During extended isolation at home, he finally tries therapy at the suggestion of other entertainers who’d benefited.
- •He finds a strong rapport with his therapist Justin, who helps him see he overthinks, reshuffles his top 10 priorities, and simplifies his mental frameworks.
- •Cowell likens therapy to going to the gym for your mind and strongly rejects stigma; he doubts anyone could honestly say ‘I didn’t need that’ after seeing a good therapist.
- 3:30:00 – 3:50:00
Fatherhood Advice, Passion Over Money, and Reframing Success
Cowell talks through the advice he’d give Eric about career and success, stressing patience, passion, and Sunday‑night excitement over status or wealth, and reflecting on being happier at times when broke than when rich but miserable.
- •He’d tell Eric to be patient, get good at whatever he chooses, and enjoy the learning journey as much as the arrival.
- •States he’s been happiest at times when he was broke and unhappiest at times when he was wealthy, proving money isn’t a linear path to contentment.
- •Sunday‑night anticipation—looking forward to Monday—is his test of being in the right field.
- •Success is not about having more than others; there will always be people with more or less.
- •He emphasises responsibility: don’t blame others if things don’t work out; trust your instincts, accept hard work, and own your decisions.
- •He recalls leaving the mailroom for a better‑paid estate agency job and becoming more unhappy, reinforcing that ‘more money’ doesn’t equal ‘better life.’
- 3:50:00 – 4:10:00
Legacy, People-First Values, and Rising Social Pressures
The conversation pivots to legacy: how Cowell wants Eric and the world to remember him, his horror at rising bullying and materialism, and his insistence that liking people and treating them well is central to both career and character.
- •He’s increasingly preoccupied with legacy—not just his, but the contestants’ clips that live online forever.
- •Quote he likes: if you live with eyes open, you’ll eventually find the person you’re looking for (your ‘Pete Waterman’).
- •Advises young people to seek mentors smarter than themselves and to prove work ethic so those mentors will invest in them.
- •As a boy, he was crushed when a celebrity refused him an autograph at The Ideal Home exhibition; vows never to do that to others.
- •He always says yes to photos and autographs, despite family irritation, seeing it as a compliment and part of the job.
- •He’s alarmed by rising bullying and unrealistic material expectations, blaming social media in part.
- •Worries about young people who think they need everything by 21 or that poor academic performance means no future; counters with his own slow‑burn trajectory.
- •He wants his legacy to be: achieved everything without a head start and treated people well—those are what he hopes Eric inherits.
- 4:10:00 – 4:45:00
One Direction, Managing Fame, and IP Regrets
Cowell examines One Direction’s formation, their solo trajectories, how he tried to prepare them for fame’s realities, and his single biggest regret: not owning the group’s name, which has complicated any potential reunion or derivative projects.
- •He views success, despite its challenges, as better than not succeeding; the issue is honest expectation‑setting.
- •He told One Direction not to complain about paparazzi, privacy loss, or exhausting schedules—they’re part of choosing stardom.
- •He regards bands as more fun than being a solo artist and often a better launchpad for solo careers.
- •On Harry Styles: he never predicted Harry would become ‘one of the most successful artists in the world’, but saw charisma from day one.
- •Cowell notes British global breakouts have plummeted in the last seven years—he can barely name three—despite social media.
- •He’s organising a new boyband search and documenting the full process, without a pre‑secured label deal; the band will have to earn it on merit.
- •He sees ‘people and personality’ as the secret sauce; authenticity beats over‑styled, over‑scripted groups.
- •With One Direction he regrets giving the band name away; each member now owns a slice, meaning one holdout can block tours.
- •He says bluntly: he should have owned the IP; next time, he will insist on owning names while still letting artists earn most of the money.
- 4:45:00
AI, Future of Entertainment, and Final Reflections
In closing, Cowell and Bartlett briefly explore AI’s impact on music, predict a boom in live entertainment and ‘real’ experiences, and end on a simple life‑changing decision: cutting sugar, alongside sleep, as foundational health choices.
- •Cowell sees AI as both opportunity and concern but believes the ‘real thing’—live human performance—will stay more compelling.
- •Mentions existing virtual Japanese acts selling out stadiums, but insists audiences want to say they were in a room with real people.
- •Stephen cites AI leaders predicting increased demand for IRL entertainment as automation frees time; Cowell agrees and notes the resurgence of legacy IP (Lego, Mario, Barbie).
- •They observe how digital extremes often revive analogue opposites—vinyl vs. streaming, slow fashion vs. fast fashion.
- •Cowell still rates artists like Queen, Bowie, Elton John, and George Michael as unmatched by most current acts.
- •Asked what one decision would most positively impact his life long-term, he answers simply: ‘Don’t eat sugar,’ tying health back to sleep and overall wellbeing.
- •He reiterates that sleep is ‘the best medicine’ and that overwork without rest is unsustainable.
