14 Conversations From The Diary of a CEO That Stay With You Long After They've Ended

The list of not-to-be-missed episodes, basically

By Tinky Ningombam | LAST UPDATED: NOV 25, 2025

There are podcasts you play in the background and then there’s The Diary of a CEO. Hosted by Steven Bartlett, this series has quietly become one of the most honest, self-aware spaces on the internet. It’s where moguls unpack their egos, artists peel back the performance, and thinkers confess what they wish they’d known sooner.

What makes The Diary of a CEO so magnetic is that each episode feels like eavesdropping on the kind of conversations people usually have only in the quiet moments between triumphs. There are no filters here, no PR-approved narratives, just unvarnished honesty about anything under the sun : success, failure or fear. Across hundreds of episodes, the podcast has built something rare, which is above just quick lessons or motivational soundbites.

If you could only dive into a handful of episodes, the list below have the ones that stay with you long after the credits roll.

Dame Dash : The Man That Discovered & Built Jay‑Z & Kanye West | E192

In this episode of The Diary of a CEO, Dame Dash reflects on his journey from Harlem to co-founding Roc-A-Fella Records. He shares how early experiences, including a childhood promise to never feel embarrassed and the death of his mother at 16, shaped his fearless mindset. Dash discusses his “superhero” mentality, survival instincts from street life and the importance of authenticity in business. He critiques the music industry’s exploitative practices and emphasizes partnerships that preserve independence.

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Jordan Peterson: How To Become The Person You’ve Always Wanted To Be | E113

In Episode 113, Dr. Jordan Peterson explores self-improvement and meaning with Steven Bartlett. He emphasizes pursuing truth over comfort, warning against wearing personas that block genuine connection. Peterson introduces “proper prayer,” a method for identifying and fixing small, known flaws to achieve consistent personal growth. He argues that meaning and not happiness, is life’s ultimate goal.

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Maisie Williams: The Painful Past Of A Game Of Thrones Star | E181

The Game of Thrones star opens up on fame and personal growth. In this episode of DOAC , Maisie Williams opens up about growing up in the global spotlight after landing her role as Arya Stark at age 12. She shares the struggles of forming her personal identity apart from her iconic character, the pressure from fame and the impact of social media scrutiny. 

Maisie reflects on her family dynamics and the importance of vulnerability in personal growth. Loaded as one of the most honest and raw conversation, this episode broke the internet.

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Jimmy Carr : The Easiest Way To Live A Happier Life | E106

Comedian Jimmy Carr reflects on leaving a corporate career to pursue comedy, highlighting the power of self-reinvention. He shares how breaking free from limiting beliefs and “changing the story you tell yourself” allowed him to chase his purpose. Carr emphasizes that luck comes from effort and improvement, not chance. And that happiness is a personal responsibility. What stands out is the practicality of it all: happiness isn’t a mystery or a mindset shift, it’s maintenance.

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Simon Sinek: The Number One Reason Why You’re Not Succeeding | E145

In this episode, leadership expert Simon Sinek explores why many people struggle to succeed. The answer being avoidance of difficult conversations. He argues that courageous leadership requires speaking uncomfortable truths, even when it triggers conflict or strong emotions. Sinek explains the difference between niceness, which avoids conflict and kindness, which embraces it for long-term growth. He emphasizes that effective leaders “stand in the fire,” holding space for others’ emotions without rushing to fix them. The discussion challenges viewers to identify the conversations they are avoiding and face them to unlock personal and professional growth.

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Mo Gawdat : Ex-Google Officer Finally Speaks Out On The Dangers Of AI | E252

Ex-Google exec Mo Gawdat shares his “happiness equation,” a framework he developed to find joy following the tragic loss of his son. He emphasizes finding true wealth in love and life experiences. Gawdat also explores the future of AI, presenting a controversial timeline predicting societal disruption until the late 2030s before a potential post-2045 AI utopia.

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Dr. Bessel van der Kolk :  The Body Trauma Expert: This Eye Movement Trick Can Fix Your Trauma! The Body Keeps The Score! | E302

A Professor of Psychiatry at Boston University and President of the Trauma Research Foundation, Dr. Bessel van der Kolk is best known as the author of the global bestseller The Body Keeps the Score. In this conversation, Dr. van der Kolk critiques traditional talk therapy for its inability to reach the “speechless” parts of the brain, advocating instead for somatic approaches like EMDR, yoga, neurofeedback and breathwork. He argues that true healing through body awareness, safety and human connection and not through conversation. Listeners often describe this episode as nothing short of life-altering.

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Lewis Capaldi: The Untold Story Of Becoming A Global Superstar At 22 | E178

In this deeply moving episode, singer-songwriter Lewis Capaldi dismantles the myth of effortless stardom, offering an unfiltered look into the emotional cost of fame. He opens up about imposter syndrome and the paralyzing pressure to replicate his debut success. Even describing panic attacks that left him feeling “disconnected from reality.” Capaldi’s candid discussion of his 2022 Tourette’s diagnosis reframes vulnerability as strength, culminating in his unforgettable Glastonbury moment, where fans sang for him mid-performance.

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Simon Cowell  : Simon Cowell Opens Up About His Heartbreaking Loss & His Regrets About One Direction! | E248

In this rare, introspective interview, Simon Cowell steps away from his sharp-tongued public persona to reveal the man behind the mogul. He opens up about going bankrupt at 30 and rebuilding his career from scratch, a humbling turning point that shaped his work ethic. The birth of his son, Eric, and a near-fatal accident profoundly shifted his outlook, grounding him in gratitude. Cowell reflects on his rise from the post room to global stardom, his only regret involving One Direction and the necessity of loyalty and evolving priorities.

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Sir Richard Branson: How A Dyslexic Dropout Built A Billion Dollar Empire! | E256

Business titan Sir Richard Branson shares how he built the Virgin empire by turning his dyslexia into a foundational business advantage, forcing him to keep everything simple and understandable. He details his "screw it, just do it" philosophy, defying conventional norms. He talks about importance of brand and media exposure in disrupting multiple industries. Branson provides an inspiring counterpoint to traditional corporate success, emphasizing that a focus on people is one of the keys to long-term entrepreneurial freedom.

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Dr. Gabor Maté: The Childhood Lie That's Ruining All Of Our Lives | E219

In this gripping episode, psychiatrist and trauma expert Dr. Gabor Maté explores how childhood trauma lodges itself in the body and manifests as adult dysfunction, addiction or chronic illness. He defines trauma as unmet emotional needs and not just as abuse. He also unpacks "The Childhood Lie," the belief that one must be perfect to be loved, leading to the suppression of authentic emotion. Dr. Maté offers a compassionate framework for understanding and healing emotional wounds, stressing that self-compassion is the essential starting point for personal freedom.

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Ben Francis: How I Built a $1.5 Billion Business At 19! | E167

In this episode, Ben Francis breaks down how Gymshark went from a teenager’s side project to a billion-dollar global brand.He outlines the blueprint for modern success, emphasizing the non-negotiable power of community-led marketing and leveraging influencer collaboration to build an authentic brand identity. He lays out a new playbook for modern entrepreneurship, one built on authenticity and the humility to keep learning in public. Francis focuses on the dedication to product and the lessons learned from scaling a company rapidly in the challenging e-commerce space, offering practical inspiration for the next generation of entrepreneurs.

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Brené Brown: The Algorithms Have Forced Us Into A Hidden Epidemic, This Is The Only Way Out!

Steve Bartlett says Brené Brown is the single most requested guest on his channel, and it’s easy to see why. In this conversation, she names what so many quietly feel — a hidden epidemic of disconnection. She breaks down how the digital world, especially social media, has rewired the way we relate to each other. What we call connection is often just a cycle of outrage, comparison, and noise that leaves us lonelier than before.

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Tony Hawk: The Man With the $1.4 Billion Name! | E227

This episode tracks the life of a man who turned a counterculture into a global phenomenon. Tony Hawk talks about how skateboarding, once dismissed as a teenage rebellion, became his lifelong business and identity. He shares how landing the first “900” changed his career overnight and how the Tony Hawk’s Pro Skater video game series turned his name into a billion-dollar brand. 

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