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

The Diary Of A CEO

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Simon Cowell is a world-renowned record producer, talent scout, and music mogul. He is best known for being a judge on some of the world’s most popular TV shows including, ‘The X Factor’, ‘Britain’s Got Talent’, ‘Pop Idol’, and ‘American Idol’. 

00:00 Intro
02:16 Early Context
03:17 Your Parents
04:32 Your Work Ethic, Where Does That Come From
07:20 The Importance of Respect
11:02 Making the Decision to Pursue Entertainment
16:24 Working in the Post Room at a Record Label
20:03 Making His Way Up in the Music Industry
24:00 Starting a Record Label with Your Boss
29:19 Creating Your First Smash Hit Record
36:44 Going Broke Right After Creating Your First Smash Hit
43:43 Meeting Pete Waterman, a Moment That Changed Everything
47:41 Being an Early Adopter of TV
56:54 Following Your Gut Regardless of the Criticism
01:03:34 Finding Westlife
01:06:34 Your Father Passing Away
01:14:41 Your Life Changing After Your Son, Eric, Was Born
01:20:13 Loyalty, Why It's So Important to Me
01:22:39 Setting New Work Boundaries in My New Life
01:26:19 Advice for a Young Simon Cowell
01:28:57 The Importance of Hard Work
01:31:34 Your Accident, Breaking Your Back in 3 Places
01:36:43 Going to Therapy
01:43:00 Foundational Advice for Anyone Starting Out in Their Career
01:46:43 The Importance of Legacy
01:50:06 The Rise of Bullying
01:52:06 One Direction
01:55:15 Searching for a New Boy Band
02:00:37 Harry Styles
02:02:58 AI Within the Music Industry
02:06:52 Will One Direction Get Back Together?
02:08:18 The Last Guest's Question

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Comments (7,496)

  1. @TheDiaryOfACEO

    If you enjoy this conversation, please can you do us a favour - subscribe & like this episode 💛👊🏾 Are you ready to think like a CEO? Gain access to the 100 CEOs newsletter here: ⁠bit.ly/100-ceos-newsletter

    1.8K likes

  2. @johnvale295

    I once drove Simon Cowell back to his home in London from Heathrow airport during the period when he was gaining a reputation as Mister Nasty on Pop Idol in the mid-2000s. All I was thinking as we walked to my car was "Don't annoy him. Don't upset him. Don't make him angry." During the journey, he was the one making polite small talk with me and I was responding with monosyllabic answers, still mindful of his TV reputation. I mis-read his address and ended up taking him to the wrong destination, but he wasn't angry and was fairly relaxed about my incompetence. When we (eventually) arrived at his home, he even invited me in for five minutes. He seemed like a genuinely decent person and this interview proves that his "Mister Nasty" persona was just an act.

    202 likes

  3. @tormenter121

    My mum was a stewardess for 30 years and said of all the celebs she met flying. Simon Cowell was the most genuine, down to earth celeb she ever met. He was so polite and friendly she said

    4.4K likes

  4. @carollive8710

    I met Simon Cowell on the streets of Beverly Hills about 10 years ago. I am not usually the person who would go up to a celebrity and interrupt them, but I was with my young teenage daughter who was excited. He was very kind, allowed her to take a photo with him and spoke a few nice words to her. I thought then he had a kind heart.

    4.8K likes

  5. @LiveLaughLove_11.11

    His story would make a good movie

    149 likes

  6. @dragostodirel

    I wanted to commend you not only for convincing Simon Cowell to join the podcast but also for the incredible way you allowed him to open up. This is by far one of the most interesting podcasts I've ever listened to. Thank you!

    1.9K likes

  7. @maryn9167

    I met Simon Cowell about 15 years ago, working in Harrods as a sales associate. He went around to each counter, smiling and saying hello. Genuinely lovely person, he deserves all his success.

    1.1K likes

  8. @VibeDaMaia

    Without trying to diminish his personal merit, to me, Simon Cowel's life story confirms the monumental influence of supporting parents in one's life. Loved this conversation. Thank you. ♡

    302 likes

  9. @ultraviolettp3446

    This was one of the best interviews I have ever witnessed. Simon Cowell is a tough nut to crack and you got him to be vulnerable and to be actually human which I thought never was possible. Kudos to you. I have been a Simon Cowell fan for years and this interview confirms that he is truly gifted with a sixth sense about people. Great job! You stunned him when you produced his work, records and cd's which he could touch and to relive the experiences, and you could see his eyes light up that someone cared. You obviously read his book and you were not the focus of the interview like so many big named interviewers have become. Simon opened up to you and you are amazing at your sincerity and appreciation of your subject of the interview.

    79 likes

  10. @ellenthom34

    I have never seen Simon so relaxed and vulnerable. Thank you for allowing your guests talk with minimal interruptions. You expressed amazement when you reached 5 million. It's apparent that audiences are starved for intelligent discourse. No matter the subject or guest I always come away elevated in mind and spirit. Love the real Simon

    589 likes

  11. @judyquattro7677

    Simon is so genuinely honest about everything he was asked. I love Simon in this format.

    986 likes

  12. @sarahjanesoggee3604

    Before retiring I was a flight attendant and had the pleasure of serving Simon and he was such a pleasure to have on board ,and to my surprise he came on board a month later and remembered me! When we landed in LA as I was getting on the crew bus I noticed him letting people take pictures with him,he must have been so tired after a long flight, but his fans came first,everything you see and hear in this interview is so spot on ,he is a real Gentleman and his parents must have been so proud,really enjoyed this podcast thank you

    1.8K likes

  13. @yall2743

    The man who don't cut corners when he speaks. I just have to see this.

  14. @maryjohnston4296

    My dad was 59yo when he died. I lived 2 states away from my parents. I just happened to be home visiting- my father was rushed to hospital and died a few hours later. I still miss him .

    134 likes

  15. @spanishdncr71

    A lot of people think of Simon Cowell as not being a nice person, but a high school friend once told me he knows Simon really well and he’s a really great person. ❤

    137 likes

  16. @giseleafecheoficial

    His parents did a brilliant job. He is a special human being.

    110 likes

  17. @salomejohn2980

    Having seen Simon only as the AGT, BGT host, this interview has completely changed my perspective! This is such an eye opener! Simon genuinely comes across as an immensely talented and yet kind and humble person; his honesty, clarity of purpose, self-belief and most of all his tremendous regard for his parents are truly admirable. I'll always look up to him ❤🙏

    115 likes

  18. @silverbirddog2761

    I'm amazed at how many times Simon Cowell has been interviewed, and how little those interviewers prepared for it, relative to how much preparation went into this interview.
    Read his book. Bought copies of his early record deals. Understood the ins and outs of business and specific details about marketing, and applied that understanding to Simon's life story.
    Hands down, great interview. Well done. It's great watching someone who is older and has lived an exciting life brighten up and reminisce about his life with a younger man interviewing him.
    You have a natural gift for leading people down a road, and guiding them through their story, that actually helps them to relive some of their best moments. It's really remarkable to watch.
    I'm only 51 minutes in, but I'm quite confident that Simon will shed some tears before it's over.

    1K likes

  19. @nancywaldman7284

    Simon, you are the first person in my 79 years old who remembers his parents! And, I admire you and respect you for loving them and talking with them in moments of your life. I am from Peru, and I live in Charlottesville, Virginia.

    91 likes

  20. @aimeedavies3197

    As someone who lost my mum and dad before 30, I found this really comforting to listen to when he spoke about his mum and dad

    279 likes