ON MONEY WORRIES… With Fern Brady and Simon Cowell

5 Jan 2026 · 15 min · 4 chapters

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How To Fail With Elizabeth Day: Episode Summary

Episode Title

ON MONEY WORRIES… With Fern Brady and Simon Cowell

Podcast Description "How To Fail with Elizabeth Day" explores the lessons learned from failures. Each episode features a guest discussing three personal failures and the growth derived from these experiences.

Episode Overview In this episode, Elizabeth Day tackles a prevalent issue—money worries. With guests Fern Brady, a comedian, and media mogul Simon Cowell, the discussion centers around the struggles of financial anxiety and the unconventional paths taken to overcome these challenges.

Key Themes and Concepts

Financial Anxiety

  • Commonality:
  • The Mental Health Foundation indicates that 72% of UK adults experience sleep loss due to financial anxiety.
  • Both guests, despite their successes, share personal experiences of financial concerns.

Fern Brady's Journey

  • University Struggles:
  • Brady faced financial difficulties in continuing her education, leading to creative survival strategies.
  • Unconventional Work:
  • She candidly discusses her experience as a stripper to fund her university education, revealing societal perceptions and personal realizations.
  • Brady reflects on the radicalization of her feminist beliefs through her experiences in strip clubs.

Simon Cowell's Financial Setbacks

  • Bankruptcy Experience:
  • Cowell shares his life-altering experience of going bankrupt in his late twenties.
  • He describes the feelings of humiliation as absent and instead views bankruptcy as a necessary puncturing of his initial inflated ego.
  • Lessons Learned:
  • Cowell emphasizes the importance of living within one’s means, highlighting the difference between perceived success and actual financial stability.

Guests' Reflections

  • Fern Brady:
  • Discusses the impact of her early financial struggles on her worldview and artistic expression.
  • Reflects on the notion of being vulnerable and how it relates to her identity as an autistic woman, along with the challenges faced in personal relationships.
  • Simon Cowell:
  • Shares how the lessons learned from bankruptcy shaped his understanding of success.
  • Provides insight into his upbringing and the influence of his parents on his perspective towards money and relationships.

Key Takeaways

  • Resilience Through Failure:
  • Both guests illustrate that failures, particularly financial ones, can lead to personal growth and resilience.
  • Candid Conversations:
  • The episode fosters an open dialogue about money, which is often stigmatized, encouraging listeners to confront their own financial anxieties.
  • Shared Experiences:
  • The shared struggles of successful individuals serve as a reminder that financial worries can affect anyone, regardless of their status.

Conclusion This episode of "How To Fail with Elizabeth Day" provides an insightful exploration of financial worries through the personal stories of Fern Brady and Simon Cowell. Their candid discussions about failure and resilience offer reassurance and inspire others who may be grappling with similar issues.

Links

  • [Listen to Fern Brady’s full episode](http://swap.fm/l/cmeompBv7EHK20enmwbS)
  • [Listen to Simon Cowell’s full episode](http://swap.fm/l/hSwuCNEuZNgnaG20v0yB)
  • Join the [How To Fail community](https://howtofail.supportingcast.fm/#content)
  • [Elizabeth's Substack](https://theelizabethday.substack.com/)

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For more insights and discussions on failure and growth, tune into "How To Fail with Elizabeth Day" on your favorite podcast platform.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Fern Brady's Financial Journey

1:10 to 2:40

Fern discusses her experiences in university, including financial struggles and her unconventional job to make ends meet.

“So you talked there about some of the challenges being at university.”

Exploring the Impact of Abuse and Autistic Vulnerability

2:40 to 5:48

Fern candidly shares her experiences with abusive relationships and how her autism contributed to her vulnerability.

“That sort of suspicion I'd say a healthy suspicion about what guys' intentions are has stayed with me forever.”

Simon Cowell's Bankruptcy Experience

5:48 to 9:14

Simon Cowell recounts his experience of bankruptcy in his late twenties and the lessons he learned from it.

“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.”

Influence of Parents on Simon Cowell's Life

9:14 to 13:06

Simon reflects on the significant influence his parents had on his life and career decisions.

“And then, yeah, when it happened, I didn't miss the house.”
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Transcript

Automatic transcript. May contain errors.

0:00It'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.

0:46So 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 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.

1:15So you talked 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 I failed first year and second year. First year I got in trouble with the police first I'd done when I was 17. Second year I had a bad boyfriend, to put it lightly, it's in the book. And then it just became, I was working in a bookies and it just was becoming clear that there wasn't going to be enough money to keep doing uni and have a go 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 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 a lot of strippers lie and mention like their best night when they talk to journalists so this girl was like I make a thousand pounds 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

2:52and 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 um I enjoyed writing about it in the book you say it radicalized you as a feminist because I remember reading feminist theory I dropped out of Arabic and switched to English Lit so you do all the feminist theory and I remember reading it and being like 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.

3:44That 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 ex and I know we had to be careful how we talk about it. Yeah this was the worst bit of writing the book easily. 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 story about this is so sad um 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 to not get sued but it felt like it was happening all over again like I started having these physical feelings that I hadn't had for years but it was important to put it in because I read this book called Aspergerals 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 um 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.

6:44Let'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 twenties, the company that owned your record label went bankrupt. Is that right? Yeah. So I had started a label with about four or 5 ,000 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 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 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 dad's and that was it I mean that was the moment I thought Christ almighty I really am broke um but they were brilliant they were kind of like it happens you know you've learned a lesson I found then a man a bank manager who lent me some money to pay back the other bank over time.

8:44So 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 Porsches, flashy, you know, it was very obnoxious. And I was very obnoxious, I think. um i'd had a big hit record robson and jerome no this was sunita actually was my first artist 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 I think I just believed because it was really my first attempt at breaking an artist that was going to last forever, and it didn't.

9:47And then, yeah, when it happened, I didn't miss the house. I definitely didn't miss the Porsche. I hated that Porsche looking back. And my mum and dad were amazing. They didn't think that I'd failed because I'd succeeded but failed at the same time. I had success, but I just didn't have any money. no one kind of like stopped being my friend I bought a TR6 for about six and a half grand which I loved it's like a car yeah 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 yes 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.

10:38How 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 at 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. When he died, he didn't have any money.

11:27however 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 it was that was really hard to see him because he was still really smart but because he was part of you know big company was over and that was kind of depressing um my mum was like super glam she reminded me of elizabeth taylor who you met when you were a child yeah yeah because our next door neighbors 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.

12:25I 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 everything my dad built up he built up himself my mum was incredibly hard-working she was a dancer

13:00please do follow how to fail to get new episodes as they land on apple podcast 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.

From the publisher

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

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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.

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