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

It was the most devastating thing that ever happened in my life. Thinking, "What have I got to live for?" And, um, oh gosh. I have to ... (whispers)

Please welcome Simon Cowell. (audience cheers)

The scale of his success is staggering. Who's changed the landscape of television and music.

Absolutely dreadful. As a kid, you were quite naive, weren't you?

Seriously naive.

Trying to take on the world with a music publishing company which fails in the car park, and then-

Yeah.

... you go from there to, "I'm gonna start my own record label at 24."

Mm. I met Sinitta in this club, and I thought, "I'm gonna make a record with her." I don't know how a record's made, I can't read music, but let's just do it. The first time, it flops. Second time, it flops. Even when I had the hit, I owed the bank £500,000 and I'm broke. But I would rather be mocked for being different than being safe.

Do you remember this single? The album hits number one.

Yeah, but this was a real bittersweet time because I get a phone call which starts with, "Are you sitting down?" And I was on a downward spiral from that period. Became a ridiculous workaholic, working till 7:00 in the morning, suffering from depression. And the truth is, I still suffer from depression at times.

What about One Direction?

The one thing I regret about One Direction is... So, boys, if you're listening...

We've just hit six million subscribers on The Diary of a CEO, so me and my team would like to do something we've never done before as a little thank you, and we're calling it the Diary of a CEO Subscriber Raffle, and here is how it works. Every episode this month, we're going to pick three current subscribers at random, and we'll send one of you a £1,000 voucher, one of you tickets to come and watch The Diary of a CEO behind the scenes live with our team, and one of you will have a 10-minute phone call with me to discuss whatever you want to talk about. If you're a subscriber, you're in the raffle. Thank you from the bottom of my heart for allowing me to do something that me and my team love doing so much. It is the greatest honor of my lifetime, and I hope it, I hope it continues, uh, off into the future. Let's get to the episode. (instrumental music plays) Simon, in order to understand the man that sits with me today, what is the early context that I must know about that will help me to understand the Simon Cowell that all of us know so well? What is that early context that, the oven that you were, you were cooked in?

Well, I had a happy childhood. I was always bored though, uh, really bored at school. I always wanted to have a life where I would be interested and have, have fun. When I was told, (laughs) "The school days are the best days of your life," I'm thinking, "Oh my God, this is terrible because I hate school." So, uh, I was really determined to do something where I would be actually just having fun. That's what I kept thinking to myself. And I want to start making my own money. Um, and, and one thing my parents did do when we were very, very young... Because in those days, you could actually, even at the age of about seven or eight, you know, i- in our neighborhood, is go round to people's houses, knock on their door and say, "Can I, can I wash your car?" (laughs) "Can I mow the lawn?" Uh, 'cause my mum and dad said, um, "If we pay for the holiday, you've gotta earn your spending money." So I'm like, "Fine." So... But I used to love it. Um, if you, if you got 10 quid for, like, washing a car, I mean it was like bingo. It was the best feeling, so...