How To Fail With Elizabeth Day - ON MONEY WORRIES… With Fern Brady and Simon Cowell

Episode Date: January 5, 2026

Money worries are far more common than we like to admit: from keeping you awake at night to quietly shaping your choices and decisions, financial anxiety affects us all - especially after a season of festive indulgence. In this episode, comedian Fern Brady (recorded live in Edinburgh) speaks about not having enough money to stay at university - and the unconventional ways she earned a living to keep going. Media mogul Simon Cowell reflects on going bankrupt in his late twenties and how he *still* worries about money even now because of the fear that he’ll have to start again from scratch. Together, these conversations explore financial failure, resilience and the belief that setbacks don’t have to define what comes next. We hope they offer reassurance to anyone feeling overwhelmed by money issues right now. Listen to Fern Brady’s full episode of How to Fail here: http://swap.fm/l/cmeompBv7EHK20enmwbS Listen to Simon Cowell’s full episode of How to Fail here: http://swap.fm/l/hSwuCNEuZNgnaG20v0yB 🔗 LINKS + MENTIONS: Elizabeth’s Substack: https://theelizabethday.substack.com/ Join the How To Fail community: https://howtofail.supportingcast.fm/#content 💌 LOVE THIS EPISODE? Subscribe on Spotify, Apple or wherever you get your podcasts Leave a 5⭐ review – it helps more people discover these stories 👋 Follow How To Fail & Elizabeth: Instagram: @howtofailpod @elizabday TikTok: @howtofailpod @elizabday Website: www.elizabethday.org Join Elizabeth Day for a special How to Fail live show at Crossed Wires Festival in Sheffield! Tickets on sale now: https://crossedwires.live/podcast/how-to-fail Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com How to Fail is an Elizabeth Day and Sony Music Entertainment Production. Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts To bring your brand to life in this podcast, email [e-mail] Learn more about your ad choices. Visit podcastchoices.com/adchoices

It's the new year and it's a time for assessment. And for many of us, financial stresses will be part of that. And if you're worried about money, I want you to know that you are not alone. We are living through such challenging times. The Mental Health Foundation found that 72% of UK adults, which translates to 39 million people, report losing sleep over money. It's certainly a common theme here on how to fail. even those we perceive of as having everything like media mogul and millionaire Simon Cowell, they talk about the anxiety it causes them too.

Comedian Fern Brady came on How to Fail last year and she spoke openly about how she didn't have enough money to stay at university. So she had to get pretty creative and work a very different job to earn her cash. Then you'll hear from Simon Cowell himself, who talks about going bankrupt in his late 20s and how four. formative that was for him. Both of these guests talk about working through financial adversity to get to where they are today and I really hope it will give you the boost that you need. First up, here's Fern.

So you talk there about some of the challenges being at university and one of the very real challenges was there not being enough money. Yeah. So the stripping. Tell us about that. So, after failed first year and second year, first year I got in trouble with the police first of all done when I was 17, second year I had a bad boyfriend

I put it lightly, it's in the book and then it just became, I was working in a bookie's and it just was becoming clear that there wasn't going to be enough money to keep doing uni and have a goal at getting into student journalism.

Everyone else seemed to either have no job at all or the uni said you could only work a certain number of hours and then there was this article in the student newspaper that was like student strippers make cash doing lap dances

or it was a snappier headline than that and it was meant to be discouraging people from going into stripping but the number of strippers that I met that got into it from that article because strippers always like a lot of strippers lie and mention like their best night when they talked to journalists.

So this girl was like, I make £1,000 a night. And it's terrible to say that I make more money in comedy than I ever did from stripping. That's how bad I was at stripping. You have to have a certain personality for it and it involves a degree of openness and goodwill towards men. And that's why you need to be like 19 or 20 when you're doing it because you've still got that hope in your eyes.

and that you don't know that men are bad yet. And then very quickly I got cynical and I remember one guy just throwing money at my face and storming out because he didn't want a lap dance. Yeah. But I enjoyed writing about it in the book. You say it radicalised you as a feminist.

Yeah. Because I remember reading feminist theory, I switched. dropped out Arabic and switched to English lit so you do all the feminist theory and I remember reading it and being like, well I don't know how this applies to me

and then started working in the strip clubs and I was like oh yeah I'm big into feminism now that sort of suspicion I'd say a healthy suspicion about what guys' intentions are has stayed with me forever

well at the same time as that kind of radicalisation was happening you touched on it there that one of the court cases involved an X, and I know we had to be careful how we talk about it. Yeah, this was the worst bit of writing the book easily. And I can't even imagine how horrendous that was to live through and then how horrendous it was to live through it again when you were writing about it.

It was a very violent assault. And I wonder whether you feel like there was any part of your autism that made you more exploitable by someone like that? Yeah, so I found out that lots of autistic women are much more likely to end up in abusive relationships and there's actually just been a newspaper. This story about this is so sad.

This girl, she was groomed by Nazis in America and thought she was in a relationship with one of them online. I mean, I could give you dozens of examples of stories like that where you just, you don't see the danger, you don't see a lot of red flags coming. So the chapter about that relationship was the first one I wrote for the book or it was one of the sample chapters that I sent in.

And it was weird because I hadn't been planning on writing a book and then something triggered a memory about that time and I just sat down and started writing it. and I had this really mad physical feeling when I was writing it and then when it came to publishing the book we had to cut so much out I had to prove certain things had happened which obviously you have to not get sued but it felt like it was happening all over again like I started having these physical feelings that hadn't had for years but it was important to put it in

because I read this book called Asper Girls that someone from my audience told me to read. It's a good book, but it's quite dry. It's not a memoir. It just lists examples of stuff that can happen to autistic women. So we're more vulnerable to things like grooming, more vulnerable to violent relationships, school bullying, blah, blah, blah. And as I was reading the book, I was like, this is like a point by point list of things that have happened to me. So I thought it might be more effective to write it as a memoir. But yeah, it was, that was by far like the hardest bit of the book coming out by far. I'm so sorry you went through that and I'm so grateful that you had the courage to write about it and to withstand it because I know

so many people will feel seen by your words and it will give them. Yeah. Let's get on to your failures. Yeah. That is one of them by the way. Okay. Yeah, I'm socially inept. I want to come back to that, actually, because I think it's so interesting hearing about someone so famous and how that has helped counteract that self-stated ineptitude. But before we do that, your first failure is bankruptcy. So this was when, in your late 20s, the company that owned your record label went bankrupt. Is that right? Yeah. So I had started a label with about four or five thousand pounds and someone had backed me financially and then the guy who backed me was part then his company was bought by another company or something i can't remember and that company went bust now when it

was public i think we were buying shares or i borrowed money i was in debt so um when the big company went bust we all went bust and then i was i mean literally back bankrupt. I owed the bank about, I think, 250,000 pounds. My house, I think, when I sold it, I still owed about 70 grand on the mortgage. I had to just get rid of everything, house, cars, everything. And luckily, my parents were in, in London, living in London. And I had to get from my old house to their apartment. And I had just about five pounds. And I kind of worked out well, the five pounds get me, you know, in a cab to my mum and dads. And that was it. I mean, that was the moment. I thought, Christ almighty, I really am broke. But they were brilliant. They were

kind of like, it happens. You know, you've learned a lesson. I found then a bank manager who lent me some money to pay back the other bank over time. So I just, in a weird way, kind of got lucky with it. When I've heard you speak about this before, you've been asked whether you felt humiliated, and you said no, that actually, in a way, it was good for the balloon to be punctured. Yeah. Tell me a bit more about that. Well, it was the 80s.

So it was kind of, everything was about Porsche's, flashy, you know, it was very obnoxious, and I was very obnoxious, I think. I'd had a big hit record. Robson and Jerome? No, this was Sanita, actually, with my. first artists and you know um the record sold about a million copies so you know i was making you know for someone in their early 20s a lot of money but it was it was really an illusion because it wasn't my company um i didn't really make much of the profits i had lots of credit cards and just

i think i just believed because it was really my my first attempt of breaking an artist that was going to last forever and it didn't and then yeah when it when it happened I didn't miss the house that definitely didn't miss the Porsche I hated that Porsche looking back and my mom and dad were amazing you know they didn't think that I'd failed because I'd succeeded but failed at the same time yes I had success but I just didn't have any money no one kind of like stopped being my friend I'd bought a TR6 for about six and a half grand which I loved it's like a car Yeah, I just loved it. I remember seeing it in a showroom, bought it. It always went wrong, but I just loved it because I could afford it. And I loved that car more than the Porsche because it was kind of everything became real at that point. And I really learned a lesson about don't borrow money. Just don't. You know, just live with what you have and just be happy with that. How obnoxious were you?

Well, I do remember one time I was driving in my Porsche, I had long hair, the top was down and I passed this pub and I remember someone shouting out, you wanker and I went, actually, you're right, I am a wanker and I put the top up. So I probably was, yeah. And your parents, Eric and Julie, were clearly a formative and profoundly important influence on you. Can you tell me a bit about them and who they were? Well, they were just amazing people. I mean, honestly, genuinely just kind people as well. I remember my dad, I suppose he would be middle class. You know, when he died, he didn't have any money. However, we did grow up in nice houses.

We were always moving. I remember that. He was very generous. He worked for a company, EMI, so he retired at 65. And once he retired, he never had another phone call. And I remember seeing that, and that was really hard to see him because he was still really smart, but because he was part of big company, it was over. And that was kind of depressing.

My mum was like super glam. She reminded me of Elizabeth Taylor. Who you met when you were a child, didn't you? Yeah, yeah, because our next-door neighbours, I think, ran one of the big studios. So they were always having these flashy parties and we'd always be looking over the fence. I think that was probably looking back, looking at that party. It was weird because I didn't want to be the actor or the actress. I wanted to be the person who had the party, even at that really young age.

So your mother was like Elizabeth Taylor. Sorry, I interrupted. Yeah, she was very glam. But again, she was very down to earth. I mean, the last thing they were were snobs. They just weren't. They were, again, very grounded. My mum didn't come for money.

My dad didn't come for money. They didn't inherit anything. My dad built up. He built up himself. My mum was incredibly hardworking. She was a dancer. Please do follow How to Fail to get new. episodes as they land on Apple Podcasts, Spotify, Amazon Music, or wherever you get your

podcasts, please tell all your friends. This is an Elizabeth Day and Sony Music Entertainment original podcast. Thank you so much for listening.