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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
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