218. The F-ckup Files: Our biggest work (and life!) failures. Summer Sessions, Episode 1

29 Jul 2025 · 53 min · 19 chapters

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In short

“The F-ckup Files” (Summer Sessions, Ep 1) where Al and Leanne share major business, career, and life failures, with a holiday, low-expectations vibe.

Guests

No external guests. Hosts are Leanne (Chartered Occupational Psychologist) and Al (business owner). They also reference people in their stories (e.g., an MD/director, a licensing officer, a solicitor, and wedding attendees), but not as podcast guests.

Key claims

  1. Failure often comes from not asking for help and trying to do everything alone (Leanne’s demotion).
  2. Legal/workarounds can buy time, but systemic risk can still collapse a business (Al’s alcohol delivery scheme).
  3. Embarrassing moments become stories you eventually laugh about (Leanne’s pool fall).

Notable examples

  • Leanne: demoted after starting welfare-to-work contracts across Manchester/Cheshire and Yorkshire; returned after marriage leave; contract broke due to missing systems; later rebuilt credibility.
  • Al: started an early-2000s late-night beer delivery business; licensing changes and court action led to bankruptcy (~£103k debt); later built wealth via repossessed houses.
  • Leanne: fell into a pool gutter at best friend’s Thai wedding (Koh Samui), soaking herself right before fireworks.

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

Chapters

Tap a time to open that second in VO

Vacation Vibes and Podcast Plans

0:45 to 2:16

Hosts discuss the casual format of the summer episodes and their vacation experience.

“And three, Bulgarians, when they say no, they nod their head.”

Transitioning to Fun Topics

2:25 to 3:30

Hosts transition back to podcast content and share plans for upcoming episodes.

“you might know me from podcasts such as The Sideways Life.”

Introduction to the 'F-ckup Files'

3:30 to 4:45

Hosts introduce the main topic of the episode: discussing their biggest failures.

“the official episode title is the fuck up files um we had some ideas with the assistance of of an ai platform um to help us generate some ideas to watch talk about and we put it to our our lovely follow us on LinkedIn.”

Al's Early Career Mistakes

4:45 to 6:00

Al begins sharing his first career disaster story from his past.

“So, Leigh, do you want to start off with your first career disaster?”

The Challenge of Management

6:00 to 7:30

Leanne shares her experience of being promoted to a management role and the struggles that followed.

“unemployed and likely their grandparents had been unemployed for a significant part of their working life.”

Navigating a Complex Work Environment

7:30 to 10:00

Leanne details the complications of managing a new project and the lack of support she faced.

“This was voluntary and delivered also in partnership with the local authority.”

Demotion and Decision Making

10:00 to 12:00

Leanne discusses the impact of her demotion and the choices she had to make afterward.

“So basically become a peer of the people I had been, I'd recruited into the business and had been managing up to that point.”

Turning Around a Contract

12:00 to 14:00

Leanne explains how she turned around her situation at work and successfully managed the contract.

“But I might find a training and development role in Gibraltar.”

Remote Management Successes and Challenges

14:00 to 19:00

Learn about the journey of working remotely and overcoming management challenges.

“We had those conversations and it worked out really well.”

The Importance of Asking for Help

19:00 to 20:30

Discover the significance of seeking support in the workplace during tough times.

“And we both had to wrangle Rory Sutherland on an episode.”
Show all 19 chapters

Reflections on Career Failures

20:30 to 23:10

Examine the lasting impact of early career failures and the lessons learned.

“But enough about me and my career disasters.”

Starting an Alcohol Delivery Business

24:00 to 28:00

Explore the challenges faced while attempting to launch a business in the early 2000s.

“So we definitely came under the off-licence rules, which meant that you were only allowed to sell alcohol during what they call permitted hours, which is 10 a.m.”

The Licensing Officer Incident

28:00 to 31:50

Learn about a complicated situation involving a licensing officer and a creative solution that led to unexpected consequences.

“can you just show me where this person ordered this alcohol?”

Life After Bankruptcy

31:50 to 33:58

Explore the challenges faced after bankruptcy and the journey towards recovery and business resurgence.

“So at that point, I got a job selling off-plan stuff.”

Stigma of Bankruptcy

33:58 to 36:52

Discuss the stigma surrounding bankruptcy in society and its impact on mental health and entrepreneurial spirit.

“But I assumed there'd be a different court.”

The Pool Gutter Incident

36:52 to 42:00

Listen to a humorous and embarrassing personal story about a wedding mishap involving a pool.

“to on the 1st of february 2020 and my teaser is that i once got in the same year i once got an investigation from the Inland Revenue and also the VAT squad.”

Falling into the Pool: A Wedding Mishap

42:00 to 47:51

Listen to a humorous recounting of a wedding disaster involving a pool mishap and the reactions that followed.

“So I couldn't actually like turn all the way.”

The Tesco Ham Incident

47:51 to 51:45

A comedic tale about a supermarket encounter that goes hilariously wrong, leading to unintentional embarrassment.

“shiny takeaways of resilience to take from it.”

Reflection on Embarrassment and Moving Forward

51:45 to 53:06

A discussion on how to cope with embarrassing moments and the importance of sharing these experiences.

“yourself i think sometimes and this is the this is the jerry springers jerry's final thought you forgive yourself sometimes.”
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Transcript

Automatic transcript. May contain errors.

0:02Leanne:Hello and welcome to Truth, Lies and Work Summer Sessions, Episode 1. My name is Leanne. I'm a Chartered Occupational Psychologist, but I'm also just a girl sat next to a pool asking her listeners to stick with her and listen to a business podcast while they're on holiday. It's a tough ask. It's difficult to follow that one. My name is Al. I'm a business owner and also sitting by our pool on our terrace. You probably hear a little bit of wind, maybe some dogs barking in the background. Perhaps the occasional stalk because we're in Bulgaria for a couple of months over summer. And fun fact for Bulgaria, a couple of things.

0:36First of all, stalks, lots of stalks. They nest on top of lampposts. They do. Two, stalks are massive. They're like the size of a cat. Probably bigger. And three, Bulgarians, when they say no, they nod their head. So we went in and asked for something in a supermarket. He said, do you have this? And they said, no, but nodded their head. Very confusing. Anyway, this is Truth, Lies and Work where we simplify the science of work and basically relax over summer I believe.

1:01Leanne:Yeah I'm not sure we'll be doing much simplifying the science of work over the next few weeks but what we will be doing is bring you into our summer holiday. The idea is it's August or pretty much I think this episode will go out a couple of days before August starts and we fancy a little break too but equally we want to bring you with us on our summer holidays. So we're going to talk to you about things that On typical Truth Lies and Work, but on very Al and Leanne. So particularly if you listen to our This Week in Work episodes, the vibe and conversation, it will feel familiar, but just slightly different topic, as well as keeping it loosely work-related, but fun work-related.

1:43The dirty little secret is that most businesses think they know their customers. They have the data, the records, the history, but it's scattered across three teams and four systems, and in our case, it's about 216 ,000 spreadsheets, which means nobody can actually use it.

1:57Leanne:What you should be doing is using HubSpot because why? HubSpot connects it all. Every interaction, every support ticket, every conversation into one platform every team can work from. So when sales talks to a customer, marketing already knows the full story and when you know more, you grow more. Nice. Check out HubSpot.com, the agentic customer platform for growing businesses.

2:24If you've listened to our previous podcast, you might know me from podcasts such as The Sideways Life. We have a podcast called A Sideways Life, which is all about our travels. We have a whole backstory about that. And you probably recognise this is a lot more like that because we're sitting with a gin and tonic.

2:41Leanne:Yes, we are. The sun is out. Unfortunately, I left my sunglasses inside and I didn't go in because I might lose connection. But see, and Leanne's all ready. She's one sip of gin and she's just getting leery. But yeah, so if you're expecting professional broadcasting and expecting something incredible from these episodes, it's probably not the episode for you. Come back in September. Now's the time to lower your expectations, friends. We're back in September. We'll be back with all the normal stuff, which is... We'll also be back in our studio in Mostar. So we'll have all the equipment there. Yes.

3:11Leanne:And we should also say as well, our Thursday episodes will remain largely the same guest interviews, but topics are a bit more relevant. um so for example on thursday we have dr elaine coming up who's talking all about the best ways to switch off during your holiday and actually enjoy it um but today we are talking about i think the official episode title is the fuck up files um we had some ideas with the assistance of of an ai platform um to help us generate some ideas to watch talk about and we put it to our our lovely follow us on LinkedIn. And this is by far the most voted episode. People want to learn how we've completely messed up our lives and we are here to deliver.

3:55Absolutely. So what we've decided to do is split into three sort of like major fuck-ups. I'm not sure whether we can say that. Might need to beep it. Might need to beep it. It's the disaster files, we'll call it. You know what we mean. So the The first one is business disasters. Second one is career disasters. And the third one is just general disasters. Life disasters. Life disasters, just roughly speaking. So prepare to cringe. So, Lee, do you want to kick off with your first? Now, in yours, it's actually, I believe, you've got two career and one personal, and I've got one business.

4:33Leanne:That much of a mess up. I've got one business. One career disaster, I've got two. To be fair, I've got two business and one personal. because my career is nothing really, I've no job since 2002, so I can't really talk about that. So, Leigh, do you want to start off with your first career disaster? Oh, yes, the time I got demoted. How could I forget? That was a tough day. So, set the scene. So, before you tell us what happened, set the scene. What was your job? What was your position? How well was it going? So, I'm going to take you back to early 2012, January, in fact, right at the start of 2012, Well, the year that Al and I were due to get married, which was a stressful...

5:13You say due to get married. We did actually get married.

5:15Leanne:No, we did. But I mean, in January, we were due to get married in the September. So a fairly high stress year all in all. I got promoted into a management role, my first management role in the company I was with, but also probably my proper management role. I'd been in a management role before. I've only had one member of staff. and it was to set up a brand new welfare to work contract called the family support program which was co-funded by the dwp and the esf support fund um very exciting um there was me there was one coach on board basically the program was to help people who were from multi-generation worklessness families so worklessness worklessness yeah so they were unemployed their parents were unemployed and likely their grandparents had been unemployed for a significant part of their working life.

6:08Leanne:I should have known it wasn't going well when on my first day we sat down in a meeting with the MD, the director of the contract, fun fact, the MD and the director of the contract were married, no pressure there, and the one coach who was also starting to work one-to-one with the customers who had been a peer of mine for a number of years and had also applied for the management job that I had subsequently got. So you got this person's job? We applied for the same job I got it. They didn't? They didn't. Oof, that's not a great start. No, it's not a great start. So we were sat in this meeting talking about what the program looked like, all the things we need to do to set it up, which is basically everything.

6:51Leanne:And after that first morning session the MD came up to me and said Leanne can I have a word she sat me down on the stairs and said you don't have to do this oh that's harsh I was like what do you mean she's like well you know if this is a bit of a stretch for you I understand your maybe your main motivation was to move back to Manchester I've been put on a contract over in Yorkshire previous and had a very long commute she said I understand there's no pressure you're more than welcome to be a coach on this contract we'll find somebody else to manage it I don't want you to feel that there's any pressure we're not a job for you here and being the naive 27 year old that I was I was like I'll be fine I've got this I'll be absolutely fine so we went through the initial setup of the contract in the northwest which is Manchester and Cheshire East it went okay started to get some people onto program it was voluntary which made it difficult so typically welfare to work contracts are mandated by job centres.

7:50Leanne:This was voluntary and delivered also in partnership with the local authority. So it was slow getting people into programme, but we were starting to get there. They also had this contract over in Yorkshire and hadn't filled that position for a manager in Yorkshire. So maybe about a month in, we're starting to make some waves in the Northwest. And I was asked to pick up the contract in Yorkshire as well. So things are going well. Things are getting better. And I got the call from the same MD that told me I didn't need to do this. So I thought that's a nice phone call, a bit of faith, a bit of trust here.

8:25Leanne:So I also then took on Yorkshire. And it was probably over the next three months that the wheels really started to fall off. If you're not from the UK, Manchester and Yorkshire aren't that close. And we had all of Yorkshire. So we're talking Yorkshire, West Yorkshire, East Yorkshire. Largest county, I think, in England. So based pretty much coast to coast of the north of England, a big area, just me, no fixed premises, all community based, had to bring in all the coaches, built a team from ground up. And that's probably the only thing that I can still say confidently that I did right because of all the members of staff that I hired in those initial four to five months.

9:07Leanne:Every single one of them, except one, remained on the contract for its entirety, which is three and a half years. Nice. So that I did well. um but understandably massive area complete startup two contracts very complex brand new I was out of my depth if I'm being honest I wasn't provided the support I probably should have been by the organization at this point um to the point where we were meant to deliver courses they weren't being developed in head office as I was promised they would then I had to pick up that as well and develop the courses myself equally did them well because those courses also stayed place for the entirety of the contract so where my strengths were recruitment pathway development training and development all that type of thing smashed it but in terms of building a contract from startup or the logistics office structure we needed systems processes I struggled and it was just it was just me so we get to about July August I know it's not going well I'm starting to feel that I'm losing control of where things are up to but I feel like it's ticking by we then go on holiday to get married we got married in Gibraltar so we had three weeks annual leave our wedding and then our honeymoon and I came back after three weeks and the entire contract was broken because I hadn't set up enough systems and processes that it could function without me being there and a new rule had come in anyway blah blah from the prime contractor which meant we didn't have the right paperwork in place anyway don't want to make any excuses I was out of my depth and I went into a meeting maybe on my third day back with said MD and my director and was told that I wasn't doing a good enough job I was being demoted and I had three options I could either become a coach on the contract in Manchester.

10:58Leanne:So basically become a peer of the people I had been, I'd recruited into the business and had been managing up to that point. That's rough. I could go back to the contract I used to work on in Yorkshire as a coach. Long commute. Long commute, demotion, back to the role I was in previously. Or a third option was I could be a tutor. So I could actually deliver the courses that I developed to the customers. So I went home. I spoke to Al, obviously, um and a couple of trusted colleagues and decided that i'd be a tutor because the other two options seemed like stepping back this at least felt like a bit of a sidestep and something new can i ask you at this point then how much of this was ego led as in you didn't want to look like you've been taking a step back it was a bit of ego but to be honest it was more from a view of career development because at this point you and i started talking about moving to spain and i kind of thought well I'm not going to find a job coach role in Gibraltar because unemployment doesn't exist in Gibraltar.

12:00Leanne:But I might find a training and development role in Gibraltar. So it was more that aspect of it. And to be fair, when I had been a coach, running the training sessions had been my favorite part of it. So I went back in the next day, said, I want to be a tutor. That's what I'll do. And the MD was not expecting that. She didn't like that. She thought I was going to go back to being a coach. So we took a break. And my director called John, who was also the MD's husband, said to me, I think you can do this. I just think it was too much for you to take on the entire North region. I think if you just have Manchester and Cheshire, with the team you've got in place, the premises you've put in place, I think in three months you'll smash it.

12:48Leanne:So he really campaigned for me to the MD to give me this opportunity. She was not keen and it was made very clear to me that if I didn't completely turn around the contract by Christmas and this would have been late September, then I was basically out of a job. So again, challenge accepted. At this point, Alan and I had already made the decision that we were going to move to Spain in the spring. So it's kind of like, well, make the most of it. Deal with what happens. and at that point as well John became much more of a hands-on mentor and over time coach and I got myself together in terms of being more organized understanding exactly where all of our customers were at where our coaches were at much more hands-on to the point of probably micromanagement within that first six weeks to understand exactly what was going on and just found our groove found the joy in what we were doing um we had a lovely wave of of inflow of customers coming on which also made everything easy to hit our targets and by christmas we were smashing it and the md came to manchester to visit me and asked me to stay on as manager fabulous is that the same contract that you ended up running from spain yes yes so this would have been at christmas and i'd already made the decision and I planned to move to Spain in May so I handed in my notice in April um contract still doing really well explained John we were moving abroad um he was very sweet gave me a hug wished me well and then the next morning I got a phone call he said to me when we left that initial meeting he's like don't talk to anyone yet obviously I want to talk it through Katrina and understand how we handle this transition um the next morning I got a phone call from John and he was like just so i understand are you leaving your job because you have another job to go to in gibraltar or you're leaving your job because you think you can't do it from while being abroad i was like the second one and he was like well i'm not so sure about that he said i think you can probably do the majority of this job remotely so go and have a think about how much of a job you think you could do what system structure potentially other members of staff you need to put in place on the ground in Manchester and talk to Al about it and see if it's even something he'd want you to consider because we would expect you to come back a week a month to the UK.

15:12We had those conversations and it worked out really well.

15:15Leanne:We flew to Spain in May and for the next two years I worked as a remote manager going back to the UK a week a month. In fact it went kind of better than that because after a year I got promoted into the national manager role where I had Manchester, I regained Yorkshire, which is the one I got demoted from and also picked up Cornwall. So let's just say that someone's listening to this and they go, oh God, yeah, I feel like that's happened to me. Or I'm at the situation where things aren't great at work, maybe not being demoted, but they just haven't got the promotion that they wanted. Is there any advice you'd give them?

15:52Leanne:I made the mistake that every first manager, the vast majority of first managers make. I felt I needed to do it all on my own. I felt I needed to have all the answers and I felt that asking for help would be a sign of weakness and signal to my incompetence. And the exact opposite is true. The minute I asked for help, went to my team, asked for their help, went to my manager, asked for his help, different colleagues across the business, is when it all turned around. I was stuck in this complete frozen threat state of overwhelm that I didn't do anything effectively. So I think if you're feeling that or if you've just been demoted or you can feel it coming, think about who around you can ask for support and ask for help.

16:40Leanne:and if it's possible to reduce your focus areas down to the absolute must be done, have to be done. So, Lee, when you look back on this, what, 13 years ago, 14 years ago, do you still see it as a career disaster?

17:00Leanne:Yes, I probably do. I probably do because I can't sugarcoat it too much. it was it was such a hard hard experience and that was also the year that I started to have really bad panic attacks so my mental health took a real toll as well and it took me a long time to rebuild my credibility with the rest of the organization my team not so much my direct managers not so much my MD not so much but gossip in organizations happens so it took me a good probably 12 months to rebuild any form of credibility if I'm being honest there are some leaders and managers in that organization that never truly saw me as a competent no matter how successful ESF was and it was by far one of the most successful contracts the organization had ever seen I think we finished with from startup we finished with maybe more than 3 ,000 customers who'd gone through the program 40 plus members of staff and we yeah we were always one of the top performing but but that um but that one that one slip stayed with me and with my reputation with certain people throughout the business it was one of the hardest things I've ever been through in my career it was really really hard because there's an element of

18:17Leanne:you have to internalize that failure to an extent that you can learn from it and grow from it and that's a process we have to go through but that little sting of failure is still there and always will be I also think that's where maybe I I've since developed a lot of empathy for people who find themselves as accidental managers or new managers without the training where I can connect with them in ways that perhaps other practitioners and trainers and coaches can't so it's definitely given me a unique perspective but if i was being honest and i could go back and have it not happen i don't know that'd be a hard choice okay we're going to take a very short break after this i believe leanne's got a question for me did you know that the uk's number one management podcast that's us by the way and the uk's number one marketing podcast are both on the same podcast network we actually have a lot in common we both use behavioral science to help people do better at work.

19:17Leanne:And we both had to wrangle Rory Sutherland on an episode. And two out of three of us are devilishly good looking. And you're not going to say which. Phil, host of Nudge, UK's number one marketing podcast. It's brought to you, we need to do this in threes. The HubSpot Podcast Network. The audio destination. Or business professional. Seamless, seamless. Tell us about your latest episode, Phil. We've just done an episode on fake fandom and how New York indie bands are paying agencies to create fake TikTok videos about how much they like their work. And we talk about the behavioral science behind fandom and how that encourages people to enjoy the music and all of that good stuff and do some big things about how this affects the world of politics, business and brands as well.

20:00It is.

20:00Leanne:It's such a good show. Of course, you'll hear all the stuff you want to hear about how to grow your business by using behavioral science in your marketing. But there's also just some really interesting episodes that will be right up your street. Personally, I enjoyed Can Balsamic Vinegar Make Beer Taste Better? It can. And Are We All Just Status Seeking Monkeys? I am. Go and listen to Nudge wherever you get your podcasts. But come back. Yeah, come back. Definitely come back, because Nudge isn't as good as this, so come back. I'll cut that out. Keep that in.

20:32Leanne:But enough about me and my career disasters. There's another one coming, don't worry. Al which one of your mess ups do you want to start with first? Let's start with a big one so it was 2002 I'd been working for about well basically I've started work in a pub then I moved up to manager then I had my own pub then I got fired from my own pub because someone was stealing and I couldn't tell them who so they were like okay well you're stealing so and I wasn't by the way but they so I got fired from that so I had a couple of really weird job sales jobs for tele sales jobs that kind of thing and then had enough of working in the office and said right i'm gonna start my start my own business 2002 it was basically if you've heard of uber eats or anything similar it was basically that in 2002 so you'd ring me up at two o 'clock in the morning and um i would bring you some beer and that was it and it was aimed at students a couple of issues with starting that business first of all the peak times as in like just when the pubs shut back then you couldn't buy alcohol 24 hours um i know for all those kids who are, oh my God, if you're born in 2002, how old would you be now?

21:40You'd be 23, wouldn't you? So yeah, those kids, so anyone who's over the age of 40 will know in the UK will know you never used to be able to buy alcohol. So this solved the problem. Basically, I'd sell it over the phone. So people would ring up and I'd get the drivers out. But there was lots of peak demand around about 11 till one and then around about sort of 2.30 till four in the morning. But I paid the drivers rather than paying per delivery. I paid them an hourly rate, which meant that I didn't make a lot of money. And the second issue was I didn't really look forward. I wasn't really careful about what was going to happen in future.

22:16I heard that the licensing law was going to change, didn't think it was going to affect me, and of course it did, it decimated it. At a high, I think we had 20 staff and we were doing 20, 30 grand a week, which back in 2002, 2003 was decent. but no that didn't work at all so essentially what happened was I was every week I was trying to make payroll and I'd ring up the bank and they'd have to give me a temporary overdraft for three days and then I'd pull I'd withdraw the money to pay all the staff and then the revenue from those three days or at least I think it was actually when the credit cards went through and when that money hit the account, it allowed me then to get back into the black, is it?

23:02See, this is why I went bankrupt because I don't know the difference between red and black. Get back into the black and it was a really tough time. I ended up moving out the house I lived in. I lived in the warehouse. I built a little room in the back and I did everything to try and keep that business alive but it was not to be. So when the licensing law came in, went from 20 grand a week to about two grand a week. Had to fire 99 % of my staff. And to be fair, two grand a week were kind of almost profitable. But by that stage, I got 103 grand's worth of debt, mainly to HSBC banks. Sorry if you worked there and you were around in 2003, 2004.

23:46And so eventually I was like, right, well, I'm going to have to declare bankruptcy. um so i did so i'm bankrupt in 2005 for 103 000 pounds

23:59Leanne:oof oof indeed before we dwell on the um bankruptcy i i want to ask you because about the because this is so like we say al is a business owner al is is i know you hate this word you are an entrepreneur in ways that there aren't many entrepreneurs because not only did you have this idea that you saw yes it's the early noughties every student wants to keep drinking after 11 o 'clock and they don't necessarily want to go out clubbing but then you also had to find very creative ways of working around the existing laws around selling alcohol so tell us a little bit about that okay so without boring you about the legal regulations back then but essentially it was something called off sales and on sales on sales were on-premises sales so it was in bars in clubs, off-premises sales was you sold alcohol to basically drink at home or drink off the premises.

24:54So that's basically what it was. So we definitely came under the off-licence rules, which meant that you were only allowed to sell alcohol during what they call permitted hours, which is 10 a.m. to 10 p.m. It sounds archaic now, and the kids these days, you know, be like, what do you mean you can't go in at three o 'clock in the morning and buy a bottle of white claw or whatever it's called? But no, you couldn't. After 10 p.m., you weren't allowed to buy any alcohol unless you went to a pub and then even then at 11 o 'clock it would shut so this was the this was the hole that i thought we could fill now the now just just to be fair there was a company out there called i can't remember they're called now um first emergency or something and they were trading but they were doing it wholesale um because weirdly in the uk and this sound boring but weirdly in the uk you are able to sell a wholesale without a without a license, which basically wholesale is 24 cans of lager.

25:47So what they were doing was students were going, can I have four cans of lager? And they're going, no, you have to buy 24. And they're like, I don't want to buy 24. Well, that's the only way we can sell it to you. So there was that. We found a slightly weird way around this. I found a law that basically said that if you're allowed to set aside orders for customers during permitted hours, and you're allowed to give it to them after permitted hours, as long as you then take the money during permitted hours. Now, bear with me. What that basically means, if Leanne said to me, I want four cans of lager tonight at 2 a.m., then I'm allowed to, in permitted hours, go into my shop, take four cans of lager, put a sticky note on, they're saying for Leanne, and then at 2 a.m., go and take that lager.

26:37I'm not allowed to take any money from her at that point. But then if I went and knocked on her door at 10.01 the next morning and said, can you pay me for those lagers? That's perfectly okay. So I was like, well, obviously that's not a good, great business plan. But you know, when you go into a hotel and they take a swipe of your card, well, I did that about the same time, which hotel took a swipe of card and was like, tell me how this works. Oh, it's called a pre, you know, I've forgotten the term, but it's called like a reserve kind of thing. Pre something it's called. and what they would do is essentially reserve the money on your card and then they would complete that purchase that transaction when you left i was like oh so that means i can go and basically take a swipe of leanne's card when i deliver the alcohol at 2 a.m and then at 10 a.m i could then complete that sale knowing the money's reserved for me for 24 hours and i could do it and i did that for like two years one of my best friends and a business partner in a current business um he was his job was to come in and essentially we had one of those old-fashioned machines where you with numbers on it where you type the credit card number in then you type the expiry date in then you type the amount you press enter and he just he just basically went through and did completions for all of the transactions the night before there'd be hundreds it'd take him four or five hours to do that but that's the way we got around it so like wow we found a way this is cool but then we got a visit from the um licensing officer first one and the licensing officer said can you just show me where this person ordered this alcohol?

28:07So go back to Leanne's example. What I was doing was taking Leanne four cans of lager at 2am, taking a swipe of her card to reserve the£10, whatever I was taking off her. And then the next morning at 10.01, I was typing her card in again and completing that transaction. The problem was the licensing officer was clever, and he was basically the police, the person who's in charge with licensing, and said, when did you when did leanne actually order that that stumped me a little bit i'll be honest because leanne hadn't ordered that she rung me up at 2am and says can you bring it to me so i was like hmm so then i wrote a bit of software back in if you remember lotus notes no i can't remember the database one was in lotus but i wrote a bit of software that essentially generated every possible combination of order for every possible customer we had a record of and we had like maybe a hundred like files and each one of those had an order like they had basically everything anyone could order from every customer so if liana ordered four cans of lager and a bottle of acardi she would have an independent order for four cans of lager and an independent order for a bottle of acardi that had been auto-generated during permitted hours that i could then prove she's pre-ordered it of course we'd never show them the files, but that's where we could do it.

29:22That satisfied the licensee officer for a little while, but then about six months later, it all went wrong.

Read the full transcript

29:27Leanne:So what happened when it went wrong? The licensee officer, I went to my solicitor by this stage, I've been working with my solicitor. Your solicitor must have loved you. He really did. It was one of the funniest gigs that you had. He really did. I think he did wills and stuff like that, boring stuff. And then this was a really bit of fun. Fun fact, he was also in the Commonwealth Games as a speedwalking walking like finalist he got bronze or something um but anyway he um he eventually wrote rung me up he went look he's we need to go to court they want to see us again so went for the magistrates and he walked into me in the magistrates court and he went bob who was the license officer's bob is furious with you he said i think it's the end of the end of the road so and it was i go in front of the mags and they basically said look no i'm rescinding your license taking it away from you're operating otherwise in accordance with the license.

30:16So I got taken away. So I was like, oh, what do I do now? Well, I did find out, remember this is the wholesale thing? As long as you sell 24 cans of lager or beer or whatever, as long as you sell 24 cans of lager, you don't need a license. Well, I looked at that and the licensing law said it could include lager, beer, and peri. Now, Perry is a pear wine. And if anyone's in the UK remembers Lambrini, Lambrini was the cheapest, petrol-ist, horriblest stuff you could possibly buy.

30:48Leanne:Lambrini girls just want to have fun. Oh, it was horrible. But you could buy a litre for genuinely about 80p back then. And that would class as wholesale. Well, if you bought a six-pack for about five pounds, that would be six litres. And that meant then your minimum order just became something like eight cans of lager or four cans of lager. I don't know exactly how we worked it out, but it basically became four cans of lager. So we still sold individually as if it was an off license, but every single customer had to buy this Lambrini to make it up to wholesale so that we weren't breaking the law.

31:25And then we also said, but don't worry if you buy it, as long as you keep it intact and give it back to us. When you order again, we'll give you a refund against it. But of course, when they ordered again, they got another case of Lambrini. So, and most people students so they drank it anyway um but then we did sell that literally at cost possibly even less than even below cost so um but yeah that lasted until the license law changed and

31:47Leanne:then that was it i went bankrupt so a fun ride i'm not gonna lie it was a lot of fun but it was also very very stressful um and um i'm now very gray and i think a lot of that came from those like five years of running that and also obviously i lost my house i got that repossessed and i also bought an investment house in manchester that got repossessed as well um and i couldn't get a bank account couldn't get a mortgage for seven years you know so but still like you say it was a lot of fun so take me back you're at this point what 27 28 yeah that's right bankrupt for 103 £3 ,000. And you do what?

32:32Leanne:What happens next? You look for a job? Do you move back with your mum and dad? What happened? So at that point, I got a job selling off-plan stuff. Now, off-plan properties, I thought it was legit. Turns out it wasn't. In fact, funnily enough, the person behind that has now been the serious fraud office have just finished an investigation. And I believe that guys looking at somewhere between eight to 10 years in the big house in the in prison um so uh yeah interesting interesting times but yes i went and did that and then um and then because i'd had my house repossessed i was like i know all about repossession i'd looked into it so um the you know the kid remember he was 17 who was doing all my all my credit card processing he'd been to university at that point um and i said do you fancy starting a business where we go and buy repossessed houses And he was like, sure.

33:23So we did. So we started a company. We bought quite a number of houses, around about 40 houses in about 18 months of people getting repossessed. And that built our wealth. So we built, and basically that's the wealth that I suppose to this day we have. So it all worked out all right in the end.

33:43Leanne:It did work out all right in the end. I want to ask you though about the immediate aftermath of being bankrupt because that is it's something then there shouldn't there shouldn't be shame attached to it but there is definitely a stigma attached to it certainly in the uk not in the entrepreneurial community because i hear people say like you're not a real entrepreneur unless you've been bankrupt at least once but certainly amongst the general kind of population bankruptcy is a bit of a is it yeah it's got a stigma how did you how is your mental health in that immediate aftermath i think i I suppose immediately, like if we're talking literally immediately, I went to court and I don't, I'd never been to court before.

34:23I had, I had been to court. I've been in court for the magistrate. Licensing laws. Licensing laws. But I assumed there'd be a different court. I assumed it'd be like the bill, you know, where there'd be like someone in a wig and I'd be stood in a box. And basically like it wasn't the magistrates. And so they'd have a big gavel and they'd be like, I declare you bankrupt. Now take him down kind of thing. and actually I sat in a room, I filled out some forms and then an hour later she came back and went, there you go, you're bankrupt. And it was such an anticlimax that I went to a local pub and I think I just spent the afternoon in there with the little money I had, just having a few beers and feeling very sorry for myself.

34:56But the truth was, this was what, 2007, so 2005, so I'd be 28 and something special about being in your 20s because you are so resilient. And so I was like, rather than going, well, my life's over, I was like, okay, what can we do now? What's next? And so I went and got that job selling dodgy stuff, which I didn't know at the time. And then start the business about a year later, maybe 18 months later.

35:23Leanne:So the same question you asked me, with that in mind, do you still see it as a business failure? No, 100 % not. Had I not had that failure early on, if I had it now, that would be difficult to recover from both financially and mentally that would be tough one to cut to it because imagine if you'd spent like 30 years building something or 20 years building something and then it went pop so no that's a tough one to come back from is that also why you're a big fan of the gen zed younger millennial generation who are out there with their side hustles and trying to build something for themselves yeah exactly i think if you're gonna get it wrong and get it wrong in your 20s.

36:05Because, in fact, you should be getting it wrong in your 20s. I think there's an old Yiddish expression that's something like if you're not making mistakes, you're not making enough decisions. And I would say in your 20s, if you're not on the brink of bankruptcy at least once every year or if you're not doing something you really, really regret, you've not done something you really regret, then you've not made enough decisions. So I think you should go out there, try everything. It's that childbirth and Morris dancing.

36:30Leanne:And I've done neither. advice taken i can't believe the time that's going by are clearly talking about trauma suits as well i i know we had another one each i wonder if maybe we talk about this another another time i guess a teaser for you headline would be i quit my job with nothing else to go to on the 1st of february 2020 and my teaser is that i once got in the same year i once got an investigation from the Inland Revenue and also the VAT squad. This is when there were two separate things. The VAT squad turned up with eight people in a black van at my warehouse and ripped everything apart. So that's going to come up in a future episode.

37:16But let's just talk, let's just finish things off with a bit of a fun one, although it's not fun for Leanne, I don't think. We're going to talk about our personal fuck-ups. We're going to talk about the time that, you know, that moment, 3am or even no probably more like 11am 11pm you were just lying in bed you're about to go to sleep and your brain just prods you and goes do you remember that time that you did this you go oh god no oh i hate it lee what does your brain say at 11pm and it's prodding you telling you did

37:47Leanne:something silly do you remember that time you fell in the pool in thailand at your best mate's wedding

37:56Leanne:I cannot believe that you are making me share this I didn't tell anyone for so long I just wanted to tell everyone because it was the funniest thing I've ever seen but at the time Even now my stomach is going I'm so Come on, get it over and done with like a plaster So set the scene, tell us what happened and tell us why it was even more mortifying than it actually sounds My best friend Alec was getting married to love his life, Kenny, in Thailand, Koh Samui. We got invited to the wedding. We were actually the only friends invited, which was a huge honour. Because there was family. Yeah, it was family.

38:34Leanne:No, they didn't elope. No, there was family there and family friends, but there was no personal friends. So we were the only two invited, which was a huge honour. Al and I being because at that point we were living in Spain were like still fit let's make a month of it and we traveled around Thailand first and then met up in Co-Smi with Alec and Kenny and the fam for the wedding um beautiful beautiful day it rained but I mean in terms of like the ceremony beautiful day they had Thai monks chanting in the ceremony and actually the rain added to it and in Thai Buddhist culture uh water is very lucky so actually they were very excited that it was raining that day and and it was a yeah beautiful beautiful ceremony beautiful meal an incredible privilege to share that very intimate moment with such a small group of people the evening comes the rain clouds parted and the um the party started in the pool area beautiful pool it's a complex called tango lux on coast mui google it it's stunning go there on your next holiday incredible in fact Alec if you're listening he's there now say hi to the gang um so we're on the we're on the pool area this must have been about I know exactly what time it was it was about quarter midnight and we were we were chatting and a few drinks had been consumed but anyone who knows me knows I'm I'm from the northwest my parents are scources and my bloodline is Irish I'm a girl that can handle her drink she can so I'd had a few drinks of course but I was by no means drunk and certainly not drunk enough for this event to happen that was coming without being absolutely mortified the pool area was stunning it's one of those infinity pools you know the one where it kind of like it has no edge only with this one it did have an edge and it was like a little two foot wide gutter that that kind of went around the area of the pool and then there the decking of the the pool area so we had been told i'll be careful of the the edge of the pool be careful the edge of the pool so i'd been stood chatting to alex mom and his niece and just chatting about various things and alex mom was very cool and very fun and very bubbly and then we hear an announcement that the fireworks are about to start at midnight how wonderful if everyone can make their way to the beach i'm in then just chattering chattering with alex mom in niece.

41:06Leanne:I turn around and the worst thing is I said something like, Linda, you're so cool at this point. My mum would probably tell me to stop drink. And then the next thing I remember is being in the pool gutter. Not even the pool. Not even the pool. If it was the pool, I would have been able to style it out. I'd have been like, hey, come on everybody. In the pool gutter. I don't even know how I got in it. I don't know because you could bang your head easily. It's two foot wide. You could have banged your head, taken your teeth out. I must have cartwheeled into it. There was no other explanation for it because to the point where when I went full under, like my head was under as well.

41:45Leanne:It wasn't just like my legs fell in. My entire head went under the water. I pop up and I'm then facing with my back to the bar area where I'd just fallen from, looking over the full pool to the hotel and have to so I'm sideways right so that the pool is like I'm looking at it so I have to turn in the gutter to be able to then fish myself out but because my hips are fairly fairly wide as any you know good looking shapely woman's is I couldn't actually turn the full way so I couldn't actually like fit my hips because it It was only like, it was honestly, it must have been like a foot and a half, like 30, 40 centimetres.

42:30Leanne:It wasn't much. So I couldn't actually like turn all the way. So I had to like lift myself up out enough. So my hips were out of the water to turn around and then lower myself back down to then see the entire freaking wedding party looking at me going, are you all right? and at this point bless Alex Alex's niece is like fishing my handbag out of the pool and and somebody's saying grab a towel um and and somebody fishes me out I can't even remember who it was and I'm trying to like oh how funny oh house leave me because I'm not drunk enough for this to be no a thing or funny you hadn't like oh gosh yeah and then at that point it was like one minute to the fireworks I was like oh my god come on everyone let's go to the beach it's distraction thank god a distraction let's go let's go with this tower i'm gonna um and then one firework goes off and then they fail all the fireworks fail so i had one rocket and that was it and then of course everyone turns back to me and goes what happened so i was like and then and then steph like sister who i actually used to work with um at pinnacle the company we've just been talking about with alec um came up to me and bless her she's she's she's a lovely lovely girl but she was laughing just like what the oh yeah and how did you do that oh my god how is it even possible and i was like i don't know she's like why is your hair wet i was like i don't know um so i was like i'm gonna take this opportunity to go in back to the the hotel room and change because i'm still dripping head to toe yeah so i went back to our beautiful little villa and it has like this little courtyard and i sat i think i got out of my dress and i sat in a dressing gown just on the on in the lounge area just thinking i can't go back out there this is the worst thing that's ever happened to me can i just just at this point i wasn't there i didn't see leanne do it i was at the bar and leanne was walking towards the fireworks and i was just finishing my beer at the bar and someone said someone's falling in the pool and i went oh my god that's embarrassing isn't it hadn't realized it was my wife so just in case you thought that i was doing nothing i was wasn't there when you fell in and you went back on your own, I believe, because you didn't want me to come with you.

44:44Leanne:No, I insisted on that. I insisted on that. So I'm sat there probably at this point about 20 past midnight at my best friend's wedding thinking I want to leave immediately. Can I book a flight out of here? And at that point, Alec comes to the door. The group, my best friend, comes to the door and he's like, he just sits down to me and is like, are you okay, hon? I'm like, no, Alec. I'm not okay. I'm not okay that is the worst thing that could have happened and you can see him kind of halfway between like genuine concern empathy and just laughing yeah you can see the pain and struggle in his face but he keeps it together he's like the end in situations like this in this situation you've got two options either you go to bed embarrassed and ruin my wedding day or you put on another dress you dry your hair you get out there and you have a great night i was like well that's not much of a choice alec is it he's like no so go and get dressed and you did i did and went back out and it's that point you know everyone's very kind at that point because i realize i think that i'm mortified it's not as funny as they thought it was so i was like are you okay did you hurt yourself and at that point i sit down next to kenny's mom denise the other the other groom and she is from preston and the most wonderful northern salt of the earth woman you'll ever meet and then I sat down and she goes you all right love I went yeah yeah so you um fell in the pool yeah did Denise yeah embarrassing that love yeah it is and then she leant over and just took my hand she went are you okay I was like yeah she's like do you want a drink I was like yeah um and then the rest was history until the next morning when I bump into Alex's cousin who who'd gone to bed already because she had a small child with her and said you're all right I heard you fell in the pool last night at that point I was like I was like I can't I can't talk about like completely tricking she's like oh my god I didn't realize it was a um so yeah so I didn't tell anyone for a while I believe that Alec and Kenny did pull up the CCTV and their subsequent honeymoon at the same resort and laughed very hard at at me falling into it I think the resort team were very pleased that I didn't launch any kind of health and safety violation given the years of which I could fall into the pool gutter and I didn't talk about it again until Al's 40th which probably would have been a year later when your sister came up to me I was like I've just been talking to Alec and he said you fell in the pool at your wedding I was like what so it gets it gets rolled out as a story amongst the friendship group from time to time but I think actually before I told my closest girlfriends it was probably a good three years later couldn't couldn't yeah mortified so thank you for letting me relive that i will spend the next 18 months trying to push that back down yeah yeah well absolutely no problem like i'm looking at now and she's like wiping her eyes and i know there's like halfway between sweating or just laughing or perhaps crying or perhaps a combination of all three so that is the most embarrassing moment of my life an absolute fail there is no lessons to be learned from it and there are no shiny takeaways of resilience to take from it.

47:53Leanne:It was the worst embarrassing moment of my life and I will never get over it. On my deathbed, I'm sure the last thing I will think about is do you remember the time you fell in the pool? And if I outlive you, then I will tell it. I know you will. I know you will. Okay. So just really quickly, because we've only got a couple of minutes left, but I will tell you my story. And my story is so, so, so simple. Do you remember it, Lee? Tesco. Yes. In the supermarket. So there's a supermarket chain in the UK called Tesco's. basically think Walmart. That's essentially the same thing. Although I'm not sure that Tesco's would be, or Tessa Cohen, the original woman who started it, would be pleased me with that comparison.

48:29So I walk into Tesco's, I go up to the meat counter and I'm like, okay, Leanne's told me to go and get some ham. So I went across to the meat counter and I saw there was like some, in the UK, they have this processed ham that's horrible. Something that looks like a teddy bear. They literally process it to make it look like a teddy bear's face. It's like, So that's like the worst ham. And then there's medium ham, which is just supposed to look like fake ham. Bit sweaty ham. Sweaty ham, which is processed, but they put little bits of white in it to make it look like it's proper ham, but it's not.

48:59That's the wafer thin ham. And then they have the good ham.

49:02Leanne:The like, like the pepper. Yes. What is it called? Like... Pepper crusted. Crusted. And it's just, it's a proper piece of pig leg sliced. It's a proper ham. It's really, really nice. So I said, can I have some ham? She pointed to the snide ham, the wafer thin ham, said, no, no, not that one. Can I have the good ham at the front? And it just so happened that this cabinet was quite kind of wide. So when I pointed at the front, it was a bit was nearest me standing face to the cabinet, but furthest for this woman to actually reach across and get. So she's trying to reach across and she can barely reach to get this with her tongs.

49:37She can barely reach to get this ham. And she picked up the first bit, it fell off and we both chuckled. and he picked up a second bit and she only pulled a little bit off and I was like, oh my God, is your arm not long enough to reach that ham? And she just stopped looking directly in the eye and just stared at me. I'm like, why the hell is she? What's wrong with her? What have I said? It's not like, and I looked across and her other arm was kind of, I don't know whether it was cut off at the elbow.

50:04Leanne:You've been amputated at the elbow. Been amputated at the elbow. That's her other arm. and I'm like, oh my God, that's why she's staring at me. And I just thought, there is nothing you can do to make this situation worse. And then my brain went, hold my beer. Because without thinking about it, I just pointed at her stumpy arm and I went, I didn't mean that one. And she, oh, she was mortified. I was mortified. I'm mortified. Right. She's heard this five times now. She's still speechless. She walked away. I walked away. Suffice to say, there was no ham sandwich that night. We had tuna instead. And that's the moment.

50:49Not the moment of like, is your arm not long enough? Because that's bad enough. But just me just saying I didn't mean that one and pointing at this poor woman's amputated arm.

51:02Leanne:That's the worst thing. I mean, you guys know Al by now. Now, you know he's a kind, intelligent, gentle soul who tries to do everything he can to make people's lives better. He's also a complete doofus. I am, 100%. And I just, it breaks my heart because I know that haunted you. It still haunts you. um and it's it's yeah it's it's it's just one of those situations where it it was a complete unintended accident that you tried to make better and failed and ultimately made worse so we didn't shop in that tesco again no we didn't and you know what this like you say you need to forgive yourself i think sometimes and this is the this is the jerry springers jerry's final thought you forgive yourself sometimes.

51:51And so often when I do think about that and I cringe so hard that sometimes I literally like sort of like curl up like a prawn then I just go, come on now. It's not that bad. At least you didn't fall in a pool. So on that bombshell, we shall leave it for today. Thank you for joining us. Thank you for having me come this far. We will have another episode like this at some point. And then I'm going to go and Leanne's going to come and have a little conversation with me.

52:17Leanne:I'm going to go cry in the bathroom. if you want to um share my humiliation come over to linkedin say hi connect say do you know what i heard your poor story and i'm equally embarrassed for you um if you have an embarrassing story to share a career fail or a business fail that maybe you learned something from or maybe it was just freaking awful share sharing is caring and i think the overall message is we all mess up it's how we respond to it and how we move forward um and we we moved forward in the best ways we could and look at us now we're sat next to a pool in in bulgaria retelling our worst moments to people on the internet who we've never met there is a worse moment than all of that and that is that my gin's finished your gin is warm you need to go and replace that so we will see you guys next week bye bye

From the publisher

This week we’re diving into our biggest professional disasters — and the personal embarrassments we still think about in the shower. From losing £103k on a failed business to being demoted out of a dream job, these are the moments that shaped us. And the ones we usually keep quiet.

Recorded poolside with a gin in hand, this is the first of our Summer Sessions — stripped-back, slightly tipsy, and very real.

🔥 What We Cover

📌 Leanne’s first big management flop
The dream promotion that turned into a living panic — and what she learned about boundaries, leadership, and starting again after being publicly demoted.

📌 Al’s bankruptcy at 26
The booze delivery startup that collapsed under licensing laws — and the brutal lessons in risk, resilience, and recovering from £103k of debt.

📌 Public fails and poolside humiliation
Leanne’s wedding faceplant in Thailand. Al’s Tesco meat counter catastrophe. We relive the awkward moments that taught us more than any win ever has.

📌 Why failure is worth sharing
We talk honestly about panic attacks, identity crises, and the long tail of shame — and why we still believe in taking big swings.

🎧 Want more from Truth, Lies & Work?
– Website: https://truthliesandwork.com
– LinkedIn: https://www.linkedin.com/company/truthlieswork
– Al Elliott: https://www.linkedin.com/in/thisisalelliott
– Leanne Elliott: https://www.linkedin.com/in/meetleanne
– Email: hello@truthliesandwork.com
– Book a call: https://savvycal.com/meetleanne/chat

🧠 Support with Mental Health and Well-being
– Mind UK: https://www.mind.org.uk/information-support/
– Samaritans (UK): Call 116 123 or email jo@samaritans.org

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