The Diary of a CEOReggie Yates Reveals The Secret To Staying Driven & Reaching Your Potential | E90
CHAPTERS
- 3:00 – 12:00
Roots, Culture, and Growing Up Between Worlds
Reggie shares his Ghanaian heritage, his parents’ migration to London, and his upbringing in Holloway and South London. He explains how West African values, a tight-knit but financially struggling household, and exposure to both council estates and affluent streets formed his early ideas about class, culture, and success.
- •Both parents are Ghanaian immigrants; grandparents moved to the UK seeking a better life for their children and grandchildren.
- •Raised initially in Holloway on a council estate, later moving to South East London; identifies strongly as a ‘Londoner’.
- •West African upbringing made education and achievement central as the perceived route out of hardship.
- •Household celebrated daily life and non-material forms of success, shaping his view that happiness is linked to fulfillment, not possessions.
- •Walks from his estate through wealthy Islington streets made him viscerally aware of class differences and sparked ambition.
- 12:00 – 28:00
Fathers, Mentors, and Breaking Generational Cycles
Reggie unpacks his complex relationship with his biological father, the contrasting parenting styles of his mum and stepfather, and his fear of inheriting toxic traits. He explains how therapy and conscious choices allowed him to step out of inherited patterns and build a mosaic of ‘Bits of Dad’ from multiple male role models.
- •Biological father was a musician but largely absent; parents divorced when Reggie was young; mum later married another Ghanaian man with a stricter, military-influenced upbringing.
- •Recognizes he and his father are similar in creativity but accepts his father wasn’t equipped for fatherhood.
- •Early fear of passing down generational trauma gave way to the belief that he defines his present and future through self-awareness.
- •Therapy helped him understand childhood trauma and the importance of consciously defining himself instead of being defined by his past.
- •‘Bits of Dad’ concept: he assembled fatherly guidance from multiple men—youth workers, TV producers, friends’ fathers—each providing different lessons (career, discipline, relationships).
- 28:00 – 42:00
From Council Estate to Set: Work, Class, and Representation
Reggie describes becoming a working child actor at eight, his early career on the Black sitcom ‘Desmond’s’, and the shock of moving between council estates and overwhelmingly white, middle-class TV sets. He reflects on how those experiences shaped his sense of difference, responsibility, and his later mission to create inclusive environments for others.
- •First major job at eight was on Channel 4’s ‘Desmond’s’, a Black family sitcom that mirrored his own family’s culture.
- •Seeing Black professionals enjoying work contradicted his grandparents’ experience of work as grueling and joyless.
- •On other sets, he was often the only Black person among a hundred crew, highlighting both racial and class isolation.
- •Noted small cultural markers of class (wine talk, lunchboxes, food, tinfoil reuse) that deepened his awareness of inequality.
- •Experiences of being visually and culturally ‘out of place’ made him hungry to one day create spaces where kids like him felt they belonged.
- •As a kids’ TV presenter dressed like estate kids (cane rows, tracksuits, Air Force 1s) on the BBC, he understood he embodied representation and relatability for young Black viewers.
- 42:00 – 1:16:00
Ambition, Platform, and the Myth of Overnight Success
The discussion turns to ambition, manifestation, and the modern obsession with relevance and quick fame. Reggie explains why he doesn’t chase ‘relevance’, how decades in media have shown him predictable cycles of rise and fall, and why he walked away from lucrative mainstream gigs to pursue documentaries with substance.
- •Reggie recalls being 12, interviewing the Spice Girls, then watching their inevitable arc from meteoric rise to decline.
- •He’s seen the same cycle repeated with boybands and now reality TV stars, only faster—sometimes just months from peak to irrelevance.
- •Rejects the goal of ‘staying relevant’, instead choosing to follow his passions and use platform responsibly.
- •At 18, a mother calling him a role model made him realize he had no choice in the matter; people would project responsibility onto him.
- •That realization pushed him away from light entertainment and toward documentaries, where he felt he should ‘have something to say’.
- •Critiques a ‘microwave era’ of success and social media ‘experts’ who want the end result without respecting the journey or work.
- 1:16:00 – 1:26:00
Failure, Cancel Culture, and Meeting Your Shadow
Reggie candidly recounts a public controversy in which his comments offended the Jewish community, triggering intense backlash and deep personal shame. He uses this episode to explore ego, accountability, and the importance of understanding your ‘shadow’—the wounded, reactive parts of yourself—as a foundation for growth and ethical use of influence.
- •He initially reacted by insisting “I didn’t mean it,” then realized intentions are irrelevant if real harm is caused.
- •The backlash felt all-consuming, but therapy helped him see his pain as partly vanity: his entire world was suddenly people upset with him.
- •Meeting with members of the Jewish community taught him about the impact of his words and helped repair some relationships.
- •Identifies a core trigger: having his character questioned undermines his self-image as a ‘good person,’ making it hard to hear criticism.
- •Therapist encouraged him to ‘get to know his shadow’—understand his worst self, patterns, and triggers—so he could handle future crises better.
- •Daniel Kaluuya’s metaphor—golf balls have dents so they can go further—reframed the scandal as a painful dent that ultimately increased Reggie’s range and depth.
- 1:26:00 – 1:44:00
Ego, Listening, and Navigating Conflict in Work and Love
The conversation broadens into ego, conflict, and emotional regulation in both professional and romantic contexts. Reggie and Steven compare how success can inflate ego, how triggers from childhood resurface in arguments, and why listening is often more powerful than winning.
- •Reggie notes many conflicts are ‘not actually about you’ but about what your actions trigger in the other person.
- •He stresses the power of shutting up and really listening, rather than chasing victory in arguments—especially with partners.
- •Acknowledges that being an outlier who has fought for success makes it easy to want to ‘win everything,’ including disagreements.
- •They reference books like ‘Ego Is the Enemy’ and ‘Leaders Eat Last’ in rethinking leadership and ego.
- •Reggie recognizes he once believed he knew more than his partners and therefore didn’t need to listen, calling that mindset unhealthy and toxic.
- •He now claims he has tools in place for most emotional situations, reducing the chance that triggers will run the show.
- 1:44:00 – 1:58:00
Leadership, Film, and Creating Space for New Voices
Reggie dives into his evolution as a filmmaker and leader, focusing on his feature film ‘Pirates’ and the way he designs environments where young actors of color can thrive. He examines his strengths and weaknesses as a leader, the importance of chemistry, and the structural barriers his cast face in an industry prone to typecasting.
- •‘Pirates’ follows three 18-year-old men of color on New Year’s Eve 1999, set against a UK Garage soundtrack.
- •Reggie deliberately employed and selected crew and heads of department to create an environment that understood and supported his young leads.
- •He organized a bonding weekend at Richard Curtis’s seaside home, where the cast cooked, watched coming-of-age films, and studied UKG culture to build authentic friendship.
- •Proud that audiences assume the three leads have been friends for years, validating his process of intentional chemistry-building.
- •Highlights typecasting: his Moroccan lead, Reda, had previously only been offered ‘terrorist’ roles and saw ‘Pirates’ as a rare chance to be funny and fully human.
- •Leadership self-critique: wants everyone happy and struggles with sacking misaligned team members; strength is nuanced people management, especially with actors.
- 1:58:00 – 2:10:00
Money, Purpose, and Walking Away from the Big Cheques
Reggie explains why he left high-profile, high-paying TV and radio jobs to pursue more meaningful work in documentary and film. He outlines his philosophy on money as a tool rather than a goal, and describes how alignment with purpose now dictates every project he takes on, from scripted drama to a Ghana-made dairy-free ice cream.
- •Hosted prime-time TV and Radio 1’s chart show for years, then quit by choice because he stopped learning and felt misaligned.
- •He didn’t want to ask pop stars shallow promo questions; he wanted to explore how they were coping as humans.
- •Accepts that leaving those roles meant a significant financial hit but prioritizes creative and ethical alignment over income.
- •Views money as important for living and supporting others but refuses to chase it as an end in itself.
- •‘Make Me Famous’ dramatized the mental health toll of social media and reality TV fame, informed by real conversations with ex-contestants.
- •Co-created a dairy-free ice cream brand manufactured in Ghana, employing thousands and paying fairly—proof that product ventures can match purpose and impact.
- 2:10:00 – 2:24:00
Love, Being a ‘Moving Target’, and Redefining Partnership
The discussion turns deeply personal as Reggie and Steven examine why high-achieving, constantly-evolving people are hard to date. Reggie reflects on his past selfishness, unrealistic expectations, and the shift from looking for perfection to seeking friendship, understanding, and mutual growth in a partner.
- •Reggie openly calls himself hard to date, likening himself and Steven to ‘moving targets’ whose evolution shrinks the viable dating pool.
- •Admits his worst romantic trait was not listening enough, assuming he knew better, and expecting partners to grow into what he needed.
- •Now sees his needs as: unconditional love, deep understanding (especially of his culture, work, and obsessions), and true friendship.
- •Clarifies the difference between empathy and understanding: a partner must grasp his Ghanaian heritage, family symbolism, and spiritual outlook to truly know him.
- •Rejects the ‘you complete me’ idea; believes each person must be whole on their own, then build a shared life together.
- •Recognizes he was once selfish and uncompromising; therapy and failed relationships taught him to value flexibility, listening, and the same grace he gives friends.
- 2:24:00 – 2:30:00
Parents, Safety, and Redefining Family Love
Reggie revisits how his parents’ volatile dynamics shaped his ideas of safety and love, and how adulthood and therapy altered his view of them. A moment in Richard Curtis and Emma Freud’s home—with a neon sign reading ‘Everything is going to be okay’—becomes a symbol of the kind of unsaid safety he wants to create for future children and loved ones.
- •Acknowledges his parents were young, lacked today’s language around mental health, and didn’t fully grasp how their arguments or styles would affect their kids.
- •He aims to judge their choices less harshly, recognizing cultural context and limited emotional tools available to their generation.
- •Contrasts that with his own era—the ‘self-help generation’—which has therapy, books, and open conversations as resources.
- •In Richard and Emma’s home, a neon sign saying ‘Everything is going to be okay’ moved him deeply; he saw it as a constant, subconscious assurance of safety for their kids.
- •Realizes love can be communicated through environment and constancy, not just words; this experience clarified what he wants his own family environment to feel like.
- •He’s forgiven his father and can now cry listening to his music, appreciating the beauty his father brought to the world even if he couldn’t give it as a parent.
- 2:30:00
Potential, Frustration, and Empowering Others Through Five Seven
In closing, Reggie articulates his belief that his potential is unlimited, grounded not in hype but in a track record of manifesting goals through work. He introduces his company Five Seven, dedicated to people, product, and content with purpose, and reflects on the tension between wanting others to realize their potential and accepting their pace and path.
- •His mum always told him his gift was ‘to see and to communicate’; he now interprets this as both creative vision and the power of manifestation.
- •Every time he has deeply wanted something and worked toward it—like turning a funeral idea into a feature film—he has eventually achieved it.
- •He feels his potential is unlimited as long as he continues to align vision, work, and purpose.
- •Five Seven (his company) spans people, product, and content, with a cause arm (Pass the Mic) to uplift young and diverse creatives.
- •Rejects using his platform to sell meaningless products; insists anything he backs should be good, purposeful, and capable of inspiring others to surpass him.
- •Acknowledges Steven’s frustration when friends underuse their potential but argues you can’t be angry at where someone is on their own trajectory; people must learn via their own mistakes and timing.
