LATE BLOOMERS - EPIC FAILS: The flops, failures, and f*ck-ups that made us who we are

Episode Date: December 17, 2025

In this episode of LATE BLOOMERS, Rich and Rox dive into the biggest flops, failures, and f*ck-ups of their lives — the ones that embarrassed them, humbled them, shaped them, and ultimately set them on the path they’re on today. Rich talks about giving up a near-pro golf trajectory at 15, two divorces by 32, and the gambling addiction that wiped out everything he had — and the gratitude and perspective that came on the other side of it. Rox shares the pain of taking down her first single after it “flopped,” the unopened post, the money chaos, and the shame stories she carried for years before learning to ask for help. Together they explore how these moments cracked them open, forced accountability, and led to therapy, sobriety, self-awareness, and the life they’re living now. It’s honest, hilarious, and painfully relatable — a reminder that everyone’s got failures, but it’s what you do with them that turns your life around.

This is the epic fails episode where we're going to be sharing with you our biggest flops, failures and fups. What's a fup? It is an F up. Ah, okay, yeah. Yeah, clean way. See what you've done there, yeah. Our mess-ups and how some of the worst moments of both of our lives have made us who we are.

So if you're in the middle of a fup right now, we hope that this can be a little boost, that things won't always be that way. Welcome to lay bloomers, where we are getting our lives together. Do do, do, do, do eventually. Right. What is it? All I remember is fups. So it's the biggest flops.

Flops, yeah. Failures. Yeah. And F-ups of our lives. Okay, lovely. That have made us who we are. So we're sort of going to look back at some of the moments we thought we were never going to recover from.

Yeah. And actually show that you can't not only recover from them, learn from them. and that they become part of your story. Now, obviously in our lives, we've got millions of those things to choose from. Yeah, definitely got a lot of thops. Got a lot of thops.

But listen, we're going to start with the flops. Okay, who's going to go first? You're going to go first. All right, fine. So if you think about your life, your whole life, sorry to put the pressure on, what's the greatest flop? that you went through?

I think probably I was maybe 15 or 16. And I was quite good at golf. So I started playing golf and I was 10. Not quite good. You were like, be real, be real. I was good at golf, right? I was good at golf. You were unreal.

Okay, well, you think that I'm unreal. There's obviously loads of really unreal players. I never got, like, pro, but I was on the way. Anyway, let me speak. So I started playing golf when I was 10, got pretty good at it. As a junior, I used to play like 54 holes a day. And with the vision of going into maybe pro, either a club pro or going on tour,

obviously had a lot of work to do before I got there, but it was definitely in that trajectory. and then I was junior captain, I was leading a team and like we were doing pretty well and then when I got to 15 got my first girlfriend, got my first part-time job and then just like stopped practicing really and then I had a kid at 17 or 18 and I think back like if I have just made potentially more sensible decisions, I would have probably been a golf pro. Yeah. Yeah. Brutal. Well, at 15, part of you decided that's not what you wanted, or you wanted different things. I think I just liked money. I liked earning money, so I would, I would be.

doing extra shifts at Sainsbury's as a supermarket that worked in and obviously hormones with the opposite sex so I was chasing that chasing tail. Chasing tail and money. Think of all the tail you would have got as a golf pro though. Yeah, well you don't think about that moment. You know, like I'm going to invest in my golf career the maximum tail in a few years. You go, I like that now. So that's what I'm going to go towards.

You shot your load too soon there. Shot my loads. I didn't mean it like that. Oh my God. I didn't actually mean it like that. Well, look, we're talking about flops and shooting loads and stuff. Like we're going too far with this one. Okay.

So you could have potentially been a golf pro. Yeah. You chose, it's not even tell you chose to have a kid. You chose a different life path. What then happened to you and golf? I mean, obviously, fatherhood didn't have time really to play. I played occasionally,

but obviously you have to practice a lot to maintain a good standard. Now I play a bit more, but just for fun, I've got no vision, want or desire to do anything, to pursue anything professionally. Or be it you, like, have this fantasy of me, like winning the open or something like no it doesn't work like i'm not 15 anymore not winning

but entering the open and just having like a late bloomer victory story i do i don't think i want to i think i just like doing it for fun which is which i do a bit more i've like got a play with my dad i've got like a golf buddy here matt which we play probably every couple of weeks different courses Playing loads more. I think it's so amazing that you've something that was such a massive passion that you then sort of had to start. It can be quite painful but you've like gone back and integrated it in. I always loved golf like it's a sport right. It was a hobby. It could have been more it wasn't and now I'm just quite comfortable with it being a being a hobby. So how has that flop made you who you are today? Well it obviously means.

you know great news everyone i'm not traveling the world playing the best courses in the world with loads of money and i'm living in a borough outside of london instead no i'm i joke uh obviously it is it is i don't know what reality would have looked like clearly um but i do know what reality looks like now i'd never met you ADHD love wouldn't have been a thing the podcast wouldn't have been a thing dubby wouldn't have been a thing so you know it it took me on a different life path but I'm incredibly happy with my life path so I'm not I'm not moaning it would have been it would have been different if I was touring the world being a golf pro but who knows that could have led to much more miserable life you struggled with addiction in your 20s so had you

have had all that money and opportunity from being a got look who knows it we all like to think of things working out but it might not have so definitely oh well okay I'm very glad to have you and I'll keep my fingers crossed for the open. Yeah, okay. Was your flop, then, biggest flop? I mean, I've got loads to choose from. So, uh... We're not talking just any flop.

No, I'm going to go with, um, my first album. Yeah, okay. Go on, tell us. My Roxanne Emery album. What was it called? Four weddings and a funeral. F-O-R. Because I sort of wrote quite sad,

reflective songs, which I think still do. Maybe a bit louder now, but yeah, I'd started doing open might nights in my early 20s. I'd got signed to management and label pretty much overnight. Put out a few singles. Put out a couple of EPs, I think. So funny, I have a fan now, Dana Rose, who was a fan of me back then. She's been a fan from day one. She has the signed EPs.

The Turnback EP. and the other one, I can't remember the name. They might be worth loads in the future. I don't think they'll get to be worth anything. You never know. Yeah, sorry. So working on music, I was very green. I was very new.

Obviously, my personal life, mum had just died. So I was in a very strange place in a young person's life. And I was working towards a debut album. I got on tour a couple of times over a couple of years. And, yeah, I really felt like I was building something. and then the situation with the label was very complicated there was an investor but he wasn't that reliable

and they weren't in a great financial situation anyway the label went bust so so my dream of having a breakout album and charting in the album chart and all that just completely bombed and obviously a record label pays for everything So I was like halfway for an album that wasn't finished. And I chose to use some money that I'd got from my mum. I sing away.

Finish the album. Obviously, you know me, reckless with money. Spending every penny I had on music doing the same thing. So yeah, paid for the out. I must have paid tens of thousands to finish this album. Do the artwork, do a video shoot. But my heart and soul into it. And then the day it came out, Total Flop.

I just remember sat in my, sat in my basement flat alone, getting drunk on ciders. And I remember just sort of tweeting, oh, the albums out after years of blood, sweat and beers. I wrote the album's out and sort of made a bit of a joke. Total Flot, so all of that money. When you say total flop, just nobody bought it, nobody listened to it? and it maybe got to like 87 in the iTunes charts but it didn't do anything it didn't make back any money

and I can't remember when but I ended up taking it offline because I was so ashamed and I was so embarrassed because I'd spent a few years of my life working to become a musician and my friends thought I was a musician and things almost looked like they were going a bit well

done these couple of tours a couple of EPs but in reality it had all fallen apart and it was a bit of smoke and mirrors and I was alone doing it incredibly upset and ashamed and yet like had a legit actual flop of something I'd spent all this time and money on. Really interesting, maybe for another day, another conversation

that you took it offline because it didn't do very well. Like that, there's something in that. Because I don't think you would do that now. If you had a song that didn't do very well, I don't think you'd take it down because it's like your art. I was so ashamed. I was like, I'm a failure. I'm disgusting.

I've spent my mum's money on this awful art project that nobody even, I just hated myself so much. I couldn't even have it online. Sometimes people ask me, now, where can I get that old album? How long was it up for? Honestly, I can't. I can't even remember a little while.

Okay. Brutal. So what's the lesson? How has that helped you become who you are today? Well, I released an album at the beginning of this year. My debut album as Rory, and it was very different. I had a team of people helping me. I had people investing in the record.

I had the beautiful band base of 37 Club waiting for it. And people listened to it and bought it. And for some reason, this time, it went in the top 10 of the UK. So it's quite crazy, the two different experiences. But I think what I want is, which is great. It's amazing. You've done a great job. That doesn't tell me how the flop helped make you.

You are that just said you released one. So I quit music after that, my own music. I swore I'd never do a solo project ever again. And then when I met you and when I started getting a bit better in life, I went back to it and actually I'd been so humbled and so hurt by it not doing well. I came back to music, A, willing to work incredibly hard to do anything. But also knowing how much it could hurt me and knowing how much I wanted it. Like, if you come back after you've failed years later, like, you really care.

So I sort of learned that even though I tried, I couldn't kill the spark in me. And it, yeah, it made me probably more resilient, more humble as well. Like, if we've already had my biggest flop, so. Yeah. People often ask now what my dream in music is. I'm like, I don't have one. It was to have a fan base and sell out a show, I've done it. Yeah.

Everything now is bonus. So yeah. All right, cool. Flops done. What's next? Now we're on to our biggest failures. It can be an actual failure or when we felt like the biggest failure in our lives. So over to you.

What's been your biggest failure in life? I would say divorces. Withness. Divorces. plural. Yeah. I was married for the first time for seven years, 18 to 25. Yeah.

And then got married, I guess maybe 26, 20. Oh, no, I didn't get married again straight away. I got my next wife a year later. We were together seven years, but only actually married for like one. Like, it was after six years. Yeah, it was after like six years. But yeah, being divorced twice by the time you're like, 32 that's a bit of a failure oh no it's so young yeah it would be young to be divorced once i mean

most people aren't even married by the time they're 32 let alone certainly not knocking up two two divorces like i wonder from a percentage point of view right i reckon that's that is point point zero zero zero zero if there's any listeners that had two divorces by 32 let rich No. Yeah, I don't think it will be. You certainly never met anyone, have you? No. I've met people that have been divorced twice, but not by 32 years old. What? It's like a sort of 65 maybe more. Yeah, so that's probably my biggest failure. And why, I guess it's an obvious question, but I do want to ask, why did it feel like such a failure? And was time one and time two different in terms of it being a failure

I mean look nobody gets married clearly to get divorced I think obviously one and two completely different people I probably wasn't

hugely different though like you know we know my story about the abuse I was younger my addiction problems and stuff like that so like I just wasn't ready to be in a relationship At 18, I wasn't ready at 26. I wasn't ready at 32. I needed to do some work. There was a lot of emotional unavailability, a lot of selfishness, a lot of addiction. So, yeah, I just, there was no way that a relationship was going to, or a marriage was going to work. And it didn't twice.

what was it like with your family like did you perceive like your mom and dad seeing you as a failure after one or two like it's like double-barreled right because getting a divorce is hard enough being embarrassed about getting divorced again makes it doubly hard because you've got obviously the oh so obviously i had a child with both of these people so like when it got to the second one. you know my youngest was four years old was getting divorced that's crap like that's just thinking about child care like am i going to be there how often am i going to see her what am i going to do and then you've got the shame about myself it's like you've been divorced twice now rich like what are you doing and then you've got to tell people which is like embarrassing to say like i like laugh about. It's not really a joking matter, but I can now. I'm, I'm years and years through like it. It's brutal. It is. Like one is traumatic enough. And then to go through it again and just telling, telling people like, oh my gosh. Okay. So how did two divorces make you

who you are today? I think, you know, it really helped me understand the need to work on myself. Well, you know, with therapy, with understanding myself, with the addictions. It really, like, made me look in the mirror. Because one, it was sort of quite easy to chalk off. I was a bit young. Maybe too young. Me, in it 16, 17.

Yeah, yeah. tells us a kids. Yeah. But two. Whereas then do it again and it's like, hang on a minute. You're the common denominator. You can't run away. Yeah.

Yeah. So like something needs to change. And obviously that doesn't, that's not going to be the same answer for everybody. It's probably going to be a different answer for everybody. But it really gave me the ability to look at myself and be like, what's going on? What's going on here? And then obviously met you, got sober, went to therapy. I'm loads calmer now.

You're a lovely young man. Used to struggle loads of anxiety. I don't anymore. But yeah, so it, I wish I would have learned it earlier. Not to not get divorced, but just be happier in myself. But I didn't. So I've still got a lot of life left, touchwood. And you've got the two kitties.

Yeah, and they're brilliant. They're brilliant, aren't they? So, you know. And I'm not like a weekend, Dad, you know, Sear lived here for a number of years. We live around the corner from Lily who's here, probably just shy 50% of the time. So like, yeah, it's, it's good. Life is, life is good. And I think they're both, okay.

Sears doing loads better. And Lily's seems absolute like loving life. We're going into teenage years the next couple of years. That's going to have its own challenges. I wait with baded breath, but oh, lovely. Thank you. your failure. Yours then, your biggest failure.

Again, loads to choose from, which is lovely. I'm going to go with near bankruptcy. Okay. It's a classic. Yeah, yeah. It's a classic. So this must have been 2019. So it's just before I've met you.

Just before I've met you. And it's the year I've just got sober. just moved back from Amsterdam. I've had the breakdown of yet another relationship. I was like 10 in a row. Also just embarrassed what's wrong with me. Shame, all that. But whilst that was going on, whilst I was drinking and relationship hopping, I was racking up an incredible amount of government debt in unpaid taxes. I was obviously doing all this. I've been doing stuff in music. I hadn't paid legal bills. Imagine owing money to a lawyer. of all people

and I'd racked up it was about 40 grand's worth of debt and then there was a bit of old phone bills that I hadn't paid for years in there and I had not opened any of the mail that I'd been sent from HMRC for years and then when I was sober

I was living with a friend and they basically encouraged me to open the letters and have a look and yeah it wasn't a pretty sight thank God really because I opened a letter that said you haven't done your taxes you owe us this much money your company's going to be struck off the register

and ceased to exist and I had about six weeks left to them good job you opened it then then very very grateful for that time so yeah then I had to like face well I'm not earning an money and I need to pay back 40 grand.

Yeah. And the government want this money back. And that actually I sort of contacted them to make a payment plan that I could afford, which they accepted. And actually through that, was able to pay off little bits and actually work it off over the next couple of years. And it was just at that moment when I think I had my first hit record and then started to earn a bit more money.

I was able to get myself out of all of that debt, but the failure of having worked in music for all these years and having my own company, and my company was named after my mum. So watching that about to go bankrupt, you're like, I'm the biggest failure known to man. Everyone was right. I should have got a normal job not done this stupid music malarkey.

So what's the learn then? Because I'm just sort of sitting here thinking, I wonder what she's going to say. Because it's not that she opens her post really regularly or that even she's particularly brilliant with money. Get a long-term partner that is a bank manager. Yeah? Yeah.

Sorted. Because you, from very early on, been very involved in what I do and so helpful. Kicking me in the ass when I'm, I need it and I'm spending too much money. Open my eyes to the fantasy. So you, being with you, I never would have spent all my money on an album

that was going to flop again. You wouldn't let that happen. No, I wouldn't. But you would be like that. You're going to hurt yourself, basically. So I have a lot of protection with you. I've got an amazing manager who also looks at that stuff. I've got an accountant that pays the taxes.

I've got all my ducks in a row now. So I guess, though, for those that aren't in the music industry and don't have accountants and bank manager, partners i suppose it's being vulnerable and asking for help asking for help it opening that first letter right in that first email it felt like 40 grand was throttling me like there is no way i couldn't pay that back in 10 years with the amount i was earning at that time um again it's made me who i am because i'm not going to say that i'm good with money because you're here and you're cool BS But it's made me...

Put you if I wasn't it? Maybe, yeah. It's made me a bit better of money. It's made me incredibly grateful that that company is still going. Yeah. That there's cash coming in that I can afford to make albums and there is money. And I'm so grateful. So it's made me just very, very grateful to be a business owner and like more conscientious

of the people that I need on the team because it can't be me. I also would say, I wouldn't say that you were good with money, but I think you do consider things more than you maybe ever used to. I don't have credit cards. No. As one small example, that's not necessarily being good with money. It's been good with myself with money. Yeah.

And that's fine. So it's finding our own way. Okay. We're on to the last one, which is your biggest F up. F up. but okay this one's well easy for me is it yeah it's losing oh no all of the money that i had yeah and going into debt on gambling so obviously we've done episodes before where we've mentioned your whole gambling story but just for a refresher for people that have heard it and obviously

for people that may not have heard those episodes can you spell your beans so i am a compulsive gambler gambling addict and it was slots gradually built I wouldn't even say gradually it quickly built up to be completely unmanageable and at the time

I remember just spinning slots on my phone one night it was a hundred pounds a spin and I was pressing it so I didn't even let it spin it was just like do do do do do do do do do do do do do and and that was the breaking point i suppose i was sweating i didn't have any money the only reason i stopped is because they wouldn't let me put any more money into my betting account because i had i had deposited 10 000 pounds that day um so didn't let me put any more in i didn't have

that money by the way by that point i'd lost everything already and that was a credit card that was but you were taking money off credit cards to gamble with yeah you can't do it anymore they've changed the law but um yeah you could put money in your betting account using a credit card instead of instead of cash they would charge you the same interest as if it was a cash transaction so yeah oh my god it was brutal and yeah that was that was the biggest low the biggest fup of my life by by far so it wasn't that was the moment but like that was that was two years in the making yeah and that's probably potentially contributed to divorce number two because that was happening.

Big time. Yeah, yeah. So how has that fup made you who you are today? I, you know, forgetting all of the GA meetings and finding community and understanding it about me, I think the biggest thing for me is the ability to be grateful for my life now. And I don't say that lightly. Like I, when things are good, I think that I feel it more than a normal. I don't know what other words to use. A normal person, a securely attached person, a happy person.

Because I've felt the opposite of it, like in a really dark way. So I think it's better for me. It's like being trapped in a cave how you would appreciate sunlight when you got out of Like, rather than somebody that just wakes up and it's just there for him every day. So, like, you've been to the lowest low with gambling, not wanted to be here anymore. Yeah. To now, like, when life is happy or you're with the kids, me, the dog, like, it's like, oh, my God. Yeah, definitely.

Almost didn't have this. Yeah. More reflective and more gratitude. Look at that. That's beautiful. That's what I was in this episode for. Yeah. To hear that.

That's, yeah. Let's have yours then. All right. again loads to choose from but I'm going to go with getting evicted oh yeah nice

juicy funny it's around the same time my album flopped so I was not doing so well and I would have been 29 and I've been in this London flat for three years

I don't remember it because I was blackout drunk most nights used to drink myself to pass out alone when I would I wasn't going out partying. Yeah, pretty dark days.

And I'd been late on rent a couple of times because I didn't have a job. I was managing someone in music and sometimes write songs. I wasn't doing my own project, but I was scrambling. I was doing the odd graphic design thing, just scrambling to make the odd 50 quid here, 100 quid there, spending a lot of money on drink and other substances. And, yeah, sometimes I was late on my rent and I had been. of given a final warning that if you're late on your rent again, you'll be evicted. I don't know if I thought he wasn't being serious or, I don't know.

It makes no sense that I did this, but I went out for a night out. You know one of those nights out that just doesn't end. It starts in a bar to another bar, to a club, ended up in a strip club, because they're always open late. you can always get a drink. My memory goes pretty hazy there, but I'm in a private booth in a strip club. Yeah.

With a card paying for all kinds of things. I sort of woke up, I got myself home somehow, thank God. And I sort of woke up in the morning, like hung over and want to come down, remembering what I'd done, feeling pretty ashamed and realizing that I'd spent not only my rent, but also a girl that worked for me, their salary. So I then had to tell my landlord I couldn't pay rent.

I had to tell someone that worked for me. I couldn't pay salary. And he said that's the final time. You're evicted. And I was given my notice. And that was just, I'd been in that flat three years. Like it was horrendous and I wasn't happy, but it was home. And that was like where my system was.

So to be thrown out and I couldn't go anywhere else because I didn't have any money. I've had to go back home with my dad and my step-mom, which I'm very grateful that they let me go home. That came with some complicated feelings as well. Yeah, big, big fup. And then I turned 30, I think a few weeks after that. And what's the learn then?

It's similar to you. like I didn't have a home until I met you. Obviously, I moved into your flat many years ago. And then a few years ago, we went to seven oaks to rent our own flat together. And I was able to pay half the rents. It's like working hard. And then this year, we bought a house at 40. I never, ever, ever thought I'd be able to own a house with the amount of debt I'd been in,

being the type of person that was evicted. So it makes me so, so, so grateful for a home for you, the kids, rock it because I know what it's like to be in such a mess with yourself that you risk your own home. So it's, yeah, it's gratitude. And I love what you said. It's like the person that's been in a cave forever that sees sunlight. I was literally in like a basement flat and the electricity had been cut off. So I was literally in like a black cave. and now I'm not so it comes with a lot of gratitude and also and also like it's a warning

to never I'll never be there again wow well that's it I like that episode yeah flops failures and fups so if you're in a flop or a failure or a fup keep going not keep going to make it worse but but stay around keep going keep going keep trying because when we make get through those things. It does make us who we are. And your amazing love story, work story, whatever it is, might just be waiting for you a few years down the road. If you have enjoyed it, leave us a comment, share it, like it, wave at us, whatever, you know what to do. And we'll see you next week. See you next week.