The Diary of a CEOEddie Hearn on Selling Matchroom For 5 Billion | E58
CHAPTERS
- 0:00 – 4:20
Opening: Obsession, Vulnerability, and the Man Behind the Promoter
Steven Bartlett frames Eddie Hearn as one of the most relentlessly driven people he’s ever met and sets the intention to explore the insecurities and vulnerabilities beneath Eddie’s public persona. He introduces themes of childhood wounds, compulsion for success, and whether ultra‑success is really a choice.
- •Steven describes Eddie as ‘neurotically obsessed’ with success and constant forward motion.
- •He links extreme success in guests to fragile, insecure backstories.
- •The conversation aims to see if Eddie’s inner world mirrors that of ‘ordinary’ people—insecurities, mental health, self‑understanding.
- •Framing of Eddie not just as a loud boxing promoter but as a complex, driven individual.
- 4:20 – 13:50
Childhood, Winning at All Costs, and the Shadow of Barry Hearn
Eddie explains how his dad’s ultra‑competitive approach and nouveau riche background shaped his obsession with winning. Growing up as Barry Hearn’s son, with a taste of early glamour and privilege, left him both spoiled and driven to surpass his father’s achievements.
- •Parents taught him that ‘taking part is irrelevant’—only winning mattered.
- •Childhood filled with competitive cricket, football, table tennis, even sparring with his dad.
- •He’s a ‘failed athlete’ who channelled his sporting obsession into promotion.
- •Describes growing up around Ferraris, limos, Eubank and Naseem Hamed, and being an ‘obnoxious’ rich kid.
- •At school he was ‘Barry Hearn’s son,’ similar to Frank Lampard being ‘Frank Lampard’s son.’
- •He feels he’s surpassed his father in some ways but can never beat the story of coming from nothing.
- 13:50 – 26:40
Being Relentless: Sacrifice, Family Guilt, and Selfish Focus
The discussion moves into the cost of Eddie’s relentless drive on his family life. He admits the inherent selfishness required to keep pushing at his level, the impossibility of balancing perfect parenting with extreme ambition, and the constant tug‑of‑war between work and being present.
- •Eddie acknowledges he texts colleagues at 3–4 a.m. and works through the night, especially with US time zones.
- •He defines himself as a family man but admits he won’t let even family obstruct crucial work.
- •Concrete images: landing from the US, driving straight to a press conference, barely making school pickup, then being on the phone at the park.
- •His daughter calling out, “Dad, please get off the phone,” hits him hard but doesn’t stop the pattern.
- •He says you can’t be a great operator without significant sacrifice, similar to elite athletes.
- •Relies heavily on an understanding partner who accepts ‘this is what he’s like.’
- 26:40 – 38:20
Deathbed Thought Experiment: Regret, Perspective, and Self-Awareness
Steven asks Eddie to imagine he only has days to live. Eddie reflects on his grandfather’s recent death, the finite nature of life, and whether he’d regret his work–life choices, concluding that he’s largely at peace because he’s ‘squeezing the juice’ out of his life.
- •Grandfather’s death made him reflect on mortality and how everything ends in a hospital bed.
- •Life is ‘a game’ and we’re on borrowed time; you can’t take yourself too seriously.
- •He believes he’d mostly say, ‘I couldn’t have done any more’—especially professionally.
- •Admits he would likely regret not spending more time with family at that moment.
- •He distinguishes between deathbed emotions and how you must act now: you follow what feels right in the present.
- •Emphasises clarity: he knows he needs to do more at home but is currently ‘okay’ with the trade‑offs.
- 38:20 – 48:40
Growing into Self-Acceptance: From Insecure Lad to Comfortable Operator
Eddie contrasts his younger self—image‑conscious, reactive to criticism, and chip‑on‑shoulder—with his more self‑accepting 41‑year‑old self. He argues that becoming comfortable with who you are is both liberating and a huge performance advantage.
- •At 27, he cared deeply what friends said about his appearance; now he laughs off hairline and weight jokes.
- •Says being comfortable with yourself is ‘the best feeling in life’ and when you become truly powerful.
- •Admits he was a ‘bit of a knob’ at school, driven by subconscious insecurity and a chip on his shoulder.
- •Highlights how people gravitate to relaxed, smiling, self‑accepting individuals in social situations.
- •Believes most 40‑year‑olds would laugh at what they worried about at 20; mindset changes massively over time.
- •Emphasises passion as the essential fuel for relentlessness—you can’t fake it long‑term.
- 48:40 – 1:00:00
Love, Marriage, and Finding Someone Who Accepts Your Obsession
Steven asks how Eddie sustains a marriage while being so work‑obsessed. Eddie shares how his wife navigates his mental absence, how they’ve grown together, and the blunt conversations he’s had about his priorities and nature.
- •His wife describes him as being ‘in his own world’ much of the time.
- •Classic scene: she explains school issues; he zones out thinking about contracts; she tests him—he fails.
- •They have major rows: accusations of selfishness, caring only about work.
- •He says he explicitly told her years ago: ‘Nothing is going to get in my way; you have to understand me.’
- •Believes early dating is hardest because partners want time, attention, and presence—things hardest for obsessives to give.
- •He makes conscious effort: racing back for dinners when exhausted, scheduling couple time even if he doesn’t feel like it.
- •Cites his parents’ old‑school dynamic and his mum’s devotion to Barry as a model he grew up around.
- 1:00:00 – 1:11:40
Is There an Endgame? Exit Fantasies, the Beach Cigar, and the Fear of Walking Away
The conversation turns to whether Eddie can ever truly stop. He fantasises about a future where he and his wife enjoy a ‘cigar on the beach’ moment, but admits that walking away from boxing and letting rivals ‘win’ currently feels unbearable.
- •His wife would probably tell ‘God’ he needs to keep doing what he does because she knows how important it is to him.
- •He doesn’t want to be 70–80 dealing with constant problems, but he’s unsure when or how to stop.
- •Family business is deeply hands‑on; he’s resisted investment and boards to maintain control and passion.
- •He’s selling his wife on a ‘faster exit strategy’—a few more big years—but isn’t sure he believes it himself.
- •Leaving boxing would feel like letting old rivals and critics ‘win,’ which he hates.
- •His dad walked away from boxing into darts and became far more relaxed—a model Eddie admires but hasn’t embraced.
- 1:11:40 – 1:21:40
Mental Health, Overthinking, and the Power of Short-Term Focus
Asked about mental health, Eddie distinguishes between normal low days and clinical depression, acknowledging his attitudes have evolved. He links mental struggle to overthinking and outlines his practical coping strategy of focusing on simple, short‑term tasks.
- •Earlier in life he was sceptical about depression, especially in seemingly ‘successful’ people; now he accepts it’s real.
- •Notes older generations like his dad took even longer to acknowledge mental health issues.
- •He personally doesn’t feel he’s had depression, but has had very down days, which he sees as normal.
- •Connects many mental health problems to overthinking and worrying about things far in the future.
- •His tactic: write down a basic daily list (walk the dog, gym, contract, shopping), then tick everything off.
- •That structure and completion feeling helps restore momentum and counters anxiety.
- •Echoes the philosophical notion that depression is past‑focused, anxiety is future‑focused, and the cure is ‘more now.’
- 1:21:40 – 1:30:00
Social Media, Criticism, and the New Burden of Celebrity
Eddie and Steven dissect the toxicity and utility of social media. Eddie tells stories of online abuse, his dad arguing with strangers on Twitter, and even having his phone number leaked, highlighting how digital criticism distorts perspective and drains energy.
- •Social media helped build Matchroom’s brand and connect with fans but has become ‘a toxic place.’
- •He’s consciously started ignoring more online negativity to protect his headspace.
- •Worries about his kids posting on TikTok and receiving cruel comments—something previous generations never dealt with.
- •Describes fans prank‑calling him after his number was leaked; he confronts one caller, urging him to focus on his own life.
- •He pities people who spend their days trolling; sees it as wasted energy and lack of purpose.
- •Within Matchroom he tries to create an environment people enjoy: food, gym, pool, travel, nights out—to spark passion.
- •Acknowledges that everyone loves praise and hates criticism, but insists you mustn’t let it steer your decisions.
- 1:30:00 – 1:37:00
Reluctant Celebrity: Using His Profile as a Promotional Weapon
Steven challenges the perception that Eddie loves the limelight. Eddie clarifies that he never set out to be a celebrity; he accepts visibility because it demonstrably grows events, fighters, and the Matchroom brand, drawing parallels to Dana White and Vince McMahon.
- •He always saw himself as a businessman continuing his dad’s work, not a public figure.
- •Recognises that being ‘the face’ of boxing helps sell shows and has become part of the model.
- •Industry critics say he’s more famous than many fighters, but he sees that as a strategic asset.
- •Cites the UFC’s Dana White and WWE’s Vince McMahon as archetypes of promoter‑as‑star.
- •Lockdown pushed him into writing a book and doing endless Zoom content out of fear of losing momentum.
- •He calls his behaviour an ‘illness’—waking up at night to do contracts and interviews—but also his advantage.
- 1:37:00 – 1:48:00
Family Business, Valuation Dreams, and the Five-Billion-Dollar Question
The final third dives into Matchroom’s future: potential investment, IPOs, and the idea of selling for UFC‑level multiples. Eddie wrestles with the tension between his father’s wish to remain a pure family business and his own desire for global scale and a huge ‘we did it’ moment.
- •Matchroom has grown from a four‑person family firm to hundreds of employees in multiple countries.
- •Hedge funds and investors approach constantly, inspired by the UFC’s $4.6bn sale; Eddie believes boxing could be worth even more under a unified model.
- •His father insists he’d ‘never’ sell, float, or take investment; Eddie argues it’s the natural next step for global expansion.
- •Lack of a son slightly changes Eddie’s sense of succession; he even toys with ending the journey alongside his dad rather than passing it on.
- •He wants offices in Sydney, Toronto, Mumbai, Beijing—because “we were never supposed to be this big,” and proving that matters to him.
- •Emphasises that more money wouldn’t materially change his lifestyle; the drive is legacy, the story, and the game of building something unprecedented.
- •Admits that even if they sold for billions, it probably wouldn’t make him deeply content—though it would create a huge ‘I can’t believe we did it’ moment.
- 1:48:00 – 1:51:40
Chaos as Stability: Addiction to Problems and Operating Under Pressure
Steven shares his idea that high achievers mistake chaos for stability and would find pure ‘stability’ chaotic. Eddie agrees, explaining that he feels most calm when dealing with crises and high stakes, much like fighters feel safest in the ring.
- •Steven observes that entrepreneurs define ‘stability’ as having problems and goals; stopping feels like chaos.
- •Eddie says he’s at his best when fights fall through, shows are in jeopardy, or everyone else is panicking.
- •He feels nervous watching AJ fight because he can’t control it, but utterly calm when fixing business crises.
- •Draws analogy to Steve Davis, who said he has ‘no nerve endings’ in big snooker moments due to repetition.
- •Eddie recalls his own first shaky press conference and how repetition turned him into a natural, note‑free speaker.
- •He argues you only become exceptional by repeatedly putting yourself into high‑pressure situations until they feel normal.
- 1:51:40
Closing Reflections: Simplicity, Honesty, and Squeezing the Most Out of Life
The conversation ends with Eddie summarising his philosophy: keep things simple, don’t overthink, be honest with yourself about your situation, and work harder when things get tough. He credits his dad’s simple but relentless mindset as a guiding principle.
- •He jokes the interview felt like another counselling session and will make him think deeply afterward.
- •Warns that over‑analysis invites doubt and mental turbulence; simplicity is protective.
- •Reiterates the importance of being brutally honest about what’s happening in your life and what you’re really doing.
- •Shares his dad’s advice: if you’ve got problems, ‘wake up an hour earlier tomorrow and go to bed an hour later.’
- •Believes that if you understand your own situation clearly, you can handle and solve it.
- •Closes on the idea that smiling, working hard, and not overcomplicating things are his core coping strategies.
