Bootstrapped 20 Years to Life Changing Exit | Simon Swords, S3E3

Simon Swords bootstrapped Fundipedia for nearly 20 years before selling to FE fundinfo in May 2025. He started in a garden shed with an Ethernet cable and a VoIP phone, ran three businesses at once for years, and eventually landed clients like HSBC, Barclays, and Legal & General. He negotiated the entire life-changing exit himself with his chairman and a ChatGPT subscription, without a corporate broker.

In this episode, Simon and I go deep on what it actually costs to play the long game. We talk about the childhood that wired him to push through anything, why he says he would rather have died than given up, and why he cried the day the deal closed.

We also get into why he sought therapy after the business was successful, not during the struggle. And why he thinks once you have the money, you're no longer allowed to be sad.

This is a conversation about whether the exit actually sets you free, or whether the real work starts after. If you're playing the long game, this one's for you.

_______

(02:00) Why bootstrapping for 20 years was the making of him
(07:31) Cumulative childhood trauma and growing up in Dagenham
(11:30) Anxiety as a superpower in business
(12:59) "I would have rather died than given up"
(15:38) Thinking he was having a heart attack on an onboarding call
(18:30) His chairman buying him out for a million pounds
(20:12) Waking up with the money and the anxiety still there
(21:52) The dragon he was chasing for 30 years
(23:30) Why most of his therapy came after success, not during
(28:30) Running the exit himself with ChatGPT
(32:31) What the cry on closing day was really about
(34:56) Why once you have money, you're not allowed to be sad
(38:30) The friends who anchor him to reality
(42:23) The panic attack that made him stop
(45:30) His 2026 plan to fill the space the business used to occupy
(48:05) What he's most proud of

Show notes:

• Find show notes of each episode on ProfitLed.fm. 

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• Follow Melissa on LinkedIn where she shares stories & lessons from her founder journey weekly.
• Connect with Melissa at melissakwan.com and subscribe to  'your founder next door', Melissa's weekly newsletter on what it's like to build a company without an abundance of resources and friends in high places.
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Transcript

SPEAKER_00 0:04

Today's guest is Simon Swords, the founder and managing director of Fundapedia. A data management platform he bootstrapped for nearly 20 years before a life-changing exit in 2025. Simon started building businesses at 16 and he eventually built Fundapedia from a garden shed with an Ethernet cable and a VoIP phone. He once ran three businesses at the same time before choosing Fundapedia as the one to focus on and eventually landing clients like HSBC and Barclays. At one point, he thought he was having a heart attack on a client onboarding call and decided to finish the call before going to the hospital. In this episode, Simon gets really honest about the childhood traumas that made him the founder he became, what it felt like to finally get the money and realize anxiety was still there, why he went to therapy after his biggest financial milestone and not before it, and the self-discovery and human journey he's on now post-exit. If you've ever wondered whether the exit actually sets you free, or whether the real work starts after, this one's for you. Welcome to another episode of ProfitLed. I'm your host, Melissa Kwan, co-founder of eWebinar. This season we're exploring the intersection of passion, profit, and purpose, and how those things change as founders evolve and come into financial success. Let's get started. Simon, you built Fundapedia for nearly 20 years before selling it. A lot of people hearing that now would think, hey, that's a long time because they're reading about two-year exits and like one year to 100 million, and they think that's the norm. And some might even hear this number and think, well, there's no way it's gonna take me that long. So I'm in a camp that believe that great companies are built in decades, not years. And I think the media really skews our idea of success and and what it should look like. What do you think about the time that you spent building? And how would you break up, I guess, those phases over the last 20 years?

SPEAKER_01 1:57

I guess Fundapedia was like the final boss of a bunch of businesses that I started, right? Back in childhood, I was I was constantly ideating about, you know, I could build a solution to that. The most silly example that sticks with me, but I would have had hundreds of these like every every month was like, wouldn't it be good if there was, and I'm sure, and I know for a fact that this has now been invented, but you've got to bear in mind I was like 13 at the time. Like, imagine if you were blind and you were filling up a bath, you'd want to be able to stick a little thing in it that beeps when the water reaches a certain level, right? Which is so mundane and silly, unless you're blind, obviously, in which case you don't really want to flood your house. So it's kind of important. The only reason I bring that up is to set this mindset of a childhood-driven approach to constantly looking for solutions to problems, rightly or wrongly, for better or worse. You know, I had to find lots of problems and kind of ideate in a business sense and ideate solutions to them. And with every kind of failure, it was kind of an iteration onto a success. And you know, touching on your point before I go through a couple of the a lot of the failures, actually, and I as you can imagine, most people don't spend a lot of time documenting them because it's much more fun to focus on the big multi-million pound exit. But when you talk about people that have that one to two year, like you say, social media driven idea that oh, I can just get a startup, get some VC money, pump it, flip it to PE, and then and I'm gonna go and sit in a yacht for the rest of my life. I know a few people that did have early success like that, and it and it ultimately blew them up. They had like initial kind of revenue and profit success, but then because they hadn't labored for years, weren't disciplined in kind of managing that, and so the thing fell over. It became too big, too quick, fell over and fell away without wanting to try and predict the future. OpenAI might be an example of that, you know, like that early mega success that then wasn't disciplined and and and didn't go on to achieve maybe what it initially set out to. So I had loads of things that I was thinking, like in terms of iterations, like I started a speed dating company with someone back when we used to have to place articles in newspapers because you couldn't SEO or pay-per-click it to the front. I started a hardware company just before Michael Dell started Dell, and I was like, oh, right, this is cool. And then one weekend your phone goes off and someone's network has gone down. So I picked up a couple of small business clocks. I'm like, oh, this is not cool. I don't want to run a business where A, my margins are being eaten by a megacorp like Dell, and B, my phone's gonna go off because they need me to come and actually change an Ethernet card, like PCI, like that's a nightmare. So then I transitioned to web design. It's like, oh well, web design's great because you can just do it from home. And if the website breaks, you can just fix it from home. It's infinitely more scalable. I'm also lazy, right? But like it's a scalable type thing, and then I realised that there's no money in that, and actually, that was a race to the bottom even 20 years ago, right? And so I think about it as that was my path. I I always wanted to bootstrap. The whole reason I started a business was that I wanted to be in control, and and I suppose if I'm gonna put my ego on the line, I wanted to be the centre of attention. I wanted to, you know, I wanted people to come to me almost, I suppose, without making it that sounds so terrible. But like I wanted to provide value in whatever that looked like, and then be worked with for that as opposed to anything else. And I suppose there was probably no other way to go about it if you weren't willing to give up the majority shareholding of your business. I had to just iterate, and even towards the end, I had a company that failed so badly, it's not even listed on company's house anymore, right? Like, and I I went to look it up because I'm sure I incorporate, I know I incorporated that as a business. It's not even there, but um even when we were building fundy, like and I'm talking like during COVID, so like 2020-2021, even then, I was selling a another business that I'd started off to one side for yeah, just under two million. That was a successful failure. It was making money, but it was going nowhere. But we took that money like and the business before that that kept the there were three core businesses towards the end before Fundy really took off and had its like J Curve or whatever people call it, hockey stick growth. It was like we had a bespoke or custom software company, we had Staff Squared, and then we had Fundy. And Atlas, the bespoke company, and Staff Squared, the stuff the HR software company, were both kind of leveraged, if you like, to fund the growth of Fundedia, and that's probably why it took so long. If I was a different guy with a different mentality, I probably could have got from zero to hero a damn sight quicker. But I'm kind of glad that I didn't. I think to be disciplined over a long period of time will leave something behind that's certainly for me more ingrained. I'm 43, right? The idea of a successful that even 33-year-old Simon who suddenly came into millions of pounds is a scary one. I don't think that I would have been a very good or nice person with it. I don't think I would have been very healthy with it. I think that I had to go, and it's very easy to say that once you're out the other side of the journey, but I genuinely believe, like with lots of biblical stories, right? You're like, oh, it didn't need to be quite as hard as that. But it's like kind of good that it was, right? Because it yielded the outcome that you wouldn't have had had that time not been invested. So that's my view on it. But like I say, it's a bootstrap view on it. It's certainly not a VCPE view on it. They would not like that.

SPEAKER_00 7:13

You've shared with me that a lot of what drove you to start a business came from childhood trauma, and that your hyper-vigilance and anxiety found a home in entrepreneurship because it was something that you could control. So can you take me back to that? Like what was going on in your early life and how did that shape the founder that you became?

SPEAKER_01 7:31

Yeah, I've not really spoken about this before. So just about to be a bit unfiltered here and might swear a bit too. So we'll see. As part of kind of prepping for this, I um pulled up my psyche vowel notes for my psychiatrist who I started to go and see back in 2023. And she had to write a letter to my insurance company to make sure that they were happy to continue paying for stuff. And it was one of the best letters I ever read, which is gonna sound odd when you hear what she said about me. It was comforting in a way to hear a doctor, a proper professional, say, as a result of Simon's childhood, which by the way is like cumulative trauma over a period of years. Simon has uh, and I'm reading rebating. All I heard was the generalized anxiety bit at the end when I initially read it, because I was probably still a little bit hyper when I first started working with her. But I read it back today, I was like, shit, Simon has emotional dysregulation, anxiety, a tendency towards catastrophic thinking, and a fragile sense of self. He does not have a formal psychiatric diagnosis, but this would be in line with generalized anxiety presentation. And when I read that again this morning, I was like, oh, okay. And and Mrs. S was in the room, she went, Well duh. Which was nice. What happened in my childhood? So I was a bit of a lono. I had a head brace, that was fun. I remember answering the door once to the small group of friends that I did have, forgot that I had it on, so they all kind of recoiled. I'll never forget that experience of them kind of A recoiling and then B laughing, that kind of sucked. I got beat up a few times by bullies. And it's worth pointing out, I was kind of born and raised in East London in a place called Dagnham, which was an industrialised blue-collar affair. So there was a lot of people kicking around and their offspring, obviously, that were just devoid of anything to do. So the social system just starts eating itself, right? Classrooms are full of kids that probably should have been diagnosed with some form of you know spectrum uh learning disability, which meant the whole class would just be taken offline because one kid's threatening to smash the place up and set fire to the school. You know, I would encounter drunk people that would literally beat me up and almost knock me out, and my friends would just run away. Friends would just run away. I had debilitating hay fever, like I had to take steroids to get through my GCSEs. Every day I would wake up with hay fever. Fortunately, I've kind of grown out of it. I'd wake up with my eyes kind of sealed shut and not be able to breathe very well, and so that caused me to turn into myself. And then my mum and dad shouldn't have been together, is is is is a really nice way to put it. They hated each other. My mum would work evening shifts and she would come home and they would have an argument. There'd typically be a door smashed or a plate smashed, because my dad would work from six in the morning till like seven or eight o'clock at night as he'd be out of the house, and my mum would go to work at like three or four o'clock and not come home till midnight. I would go home to an empty house. That was in a way the making of me. I'd taught myself to play guitar because it's better to do that. I'd teach myself like VB scripts or HTML because I, you know, I was quite lucky I had a computer and the internet was just coming around and all of that good stuff. But it taught me a lot of self-reliance in a good and a bad way, right? Like it it made me not want to rely on anybody else for help. It made me resilient in a way I can endure pain, mental and physical, in a way that isn't normal. I wouldn't wish that on anybody else. It's not nice. It these all sound like great superpowers on the surface of it, right? You would say to most people, oh my god, Simon's so tough. And where did he get all that from? Well, he got all of that from having a really horrendous time of it and using humour as a mechanism. Well, look, if they're if they're laughing, they're not beating you up. It is very much a defense strategy that I use to this day. If I'm in an awkward sales pitch for software and the internet goes down, you better believe I'm gonna make people laugh. It is such a weapon. And so, to answer, kind of come back to your question, and how does that shape you in business? Well, it makes you bloody good at recognising threats. If you've got generalized anxiety, you've got two choices. You can either, and I see this a lot in a lot of people, and it's fair enough, I'm not judging. You see, people just go, fuck it, I can't do it. And and and and just sit down, right? And and or walk away or go or go away, fight or fly, right? Or you or you fight and you channel that anxiety into, in my case, a very long to-do list that my wife will look at and it gives her anxiety. But ironically, she's like, I look at your to-do list, and she goes, I just can't. And I'm like, Well, yeah, we're wired up differently, right? That to me is focus and control and execution, and I set a big to-do list that comes down to a little to-do list that comes down, you know, and it's all there, and I can manage it and channel my thoughts through it. The idea of waking up one day and not having that, terrifying. Like, I sold the business in May last year. You better believe I've still I'm looking at it now. I've still got a to-do list, right? Because to take that away would be to allow the anxiety to come back in and to use a ship analogy, I would no longer be anchored. But like, rather than completely giving myself up to falling over, 10% of that generalized anxiety went into probably not so good things for me, and the other 90% went into that business, and it was all I thought about.

SPEAKER_00 12:59

So I listened to your Practical Founders podcast, which you talked a lot about your business journey, and you said that you would have rather died than given up.

SPEAKER_01 13:09

Yeah, I would have.

SPEAKER_00 13:10

Was that about the business or was it about yourself and proving something?

SPEAKER_01 13:16

I like the line: most ambition is just unresolved pain. But to be honest with you, Melissa, I kind of apply this approach to everything, right? I've joined a band, I'm building a car, I've got my pilot's license. I don't mind if the plane crashes and I die. I do mind if it's because I didn't do enough planning that day. But if the plane goes down because the circumstance is outside my control, I'm obviously going to try and survive the plane crash, but then that's life, right? So it's this weird disassociation from inputs and outputs. This this kind of mentality provides you. It's that lovely but also chaotic and anarchic take on life, which is to oversee the downsides because you're going to over-prepare. I was watching a podcast the other day where some CIA recruiter was saying, We love people with anxiety, they're they're our favourite because they never ever turn up un underprepared. In fact, they never turn up just prepared, they turn up like well over-prepared, and we know exactly what we're getting with them. And then we can set them another task and raise the bar even more, and they'll go and over-prepare for that. They're great. I was confident that I was never gonna let the business fall apart as a result of my negligence. If it did ever die, it would not have been on my watch, it would never have been a oh Simon gave up and rolled over. It would have been a bloody hell, Simon nearly killed himself, you know, the stress of it all. And and especially once you start to bring other people along that journey, you've got to bear in mind towards the end, I had like nearly 40 members of staff, and then I've got their families and their mortgages, so many other things going on around all of it, right? And then my clients don't want to let my clients down either, right? I know you know this because you run these types of businesses too. So it wouldn't have just been me giving up, it would have been giving up for them too. And if I ever did have to say to them, guys, it's blown up, it's dead, I'm so sorry. They would have visibly seen in my body, I would have had blood pouring out of me that I did everything I could have done, and they would have gone fucking hell, so you've got to stop, mate, because you're gonna kill you're gonna kill yourself. Again, it's probably that emotional dysregulation coming in again. I would not feel happy unless they could see that I was bleeding out for it and for them, and and that's what creates this incredible thing, but obviously is not great for you, the individual, to put it mildly.

SPEAKER_00 15:39

I mean, for years you were running three businesses until you know your mentor called you out, you chose Fundapedia as the one business that you were gonna focus on. How many years did it take before you were out of survival mode and that you felt like things were getting easier? Was it like compounded success or was it like a single event that happened?

SPEAKER_01 16:01

It was a single event. So, as you all know, when you first start a business, especially as a young person, or if you're an immature idiot and you can be an older person than be an immature idiot. So I know a few of those, bless them. You don't see the distinction between the business bank account and your bank account. Like, oh, it's half a million quid in the business bank account. I'm a half a millionaire. No, no, you haven't paid tax on that money to put it out to your personal bank account. You are not half a millionaire. You have access to half a million pounds, but you will go to prison if you take that out and run away with it because there's people that are like, you know what I mean. So the business started to get some decent funding in it. We landed HSBC around 2019-2020. They were paying us a decent, they were our biggest client by a country mile. And to onboard HSBC took about a year. And I think my chairman, who is a very, very smart man, John, and not just smart intelligence-wise, smart emotionally at reading people, right? So he would have seen in me all the things that my psychiatrist saw, he could see that I was pouring my heart into getting HSBC live. I remember one of the times we were onboarding HSBC, I thought I was having a heart attack. I'm not joking. I I genuinely had a pain in my chest that I thought, I've got to stay on this call because it's an important HSBC onboarding call. But if this pain's still here, by the time I get done, which again is ridiculous, right? You're having a pain in your chest. Most normal people would go, screw HSBC. I think about it, I genuinely think I like bearing in mind this is a compounding of nine at that point, 16 years of stress and anxiety. I've got to go straight to the hospital. My take on it was I'll just finish this chat about how we're going to get the JSON files from this server to that server, the GRD server or whatever. And then, so long as the pain's still this bad or worse, I will then go to the hospital, like nuts, right? I only bring up that element of it as one very small, if I'm honest, example of how nuts it was, the magnitude of pressure that I was under. And then John said, let's go and talk to some people because now that we're getting up to these levels of revenue, we should be able to maybe sell a bit of the business to like a PE type company or whatever, and take some skin out of the game, right? Because at the moment I had at that time 99% of my net worth tied up in this business, right? So he he could see, bless him, the the dichotomy of my goodness, this looks like mega success on the business side, but Sai's still living a life of well, put it this way: some of my staff are earning more than me, right? Which is fine, that's just life. And all of my clients, bearing in mind, we're selling to financial services businesses. And and Johnny's from a financial services background, so he knows that world inside out and back to front. So, and I'm having dinner with these firms, trying to, these people trying, they're on half a million a year. I was probably earning 60 grand a year, 70 grand a year, right? So he could see that very smartly, he could tell that if we didn't do something to address that imbalance sooner or later, I was going to start to wonder what it was all about. So, anyway, we went and did this chat, had a chat with a couple of like investment type businesses. And then one day John said, How much do you want? What what number would give you comfort that if it all fell over tomorrow, you would feel like this wasn't a waste of 15, 16 years of your life? I said, Well, a million quid's a nice fan number, John.

SPEAKER_00 19:26

John is your business partner.

SPEAKER_01 19:28

He was my chairman and second largest shareholder in the business, yeah.

SPEAKER_00 19:31

Yeah.

SPEAKER_01 19:32

And he said, fuck it, I'll write you a check for a million quid. Let's do that. Let's stop worrying about getting third-party people involved. I'll buy you out, you sell your shares to me, I'll give you a million quid, they're all thereabouts. And and the numbers didn't quite come to that. Like we had to, there were some backs and forwards on it.

SPEAKER_00 19:52

But you didn't sell all your shares, it was like a portion.

SPEAKER_01 19:55

It was just a very small amount at the time for a chunk of money that in in any circle from any working class background, you would say prior to the event that I then had last year, it was a life-changing amount of money, right? It just was.

SPEAKER_00 20:12

Yeah.

SPEAKER_01 20:12

And I remember getting the money, I remember still being knee-deep in the work, uh, and I remember waking up one day and going, Fuck me, the anxiety's still there. This has all been a total waste of time. And it was about then that I went to see Dr. Amy and the psych, you know, uh doctor, and had a chat with her about everything. Uh, and she, you know, did an incredible job using CBT of taking me through a process of reevaluating what it is to be me and and take me on a journey to get comfortable with that. Because up until, you know, because it just it did not bring the the the relief, if you like, that um I was I was looking for. It just didn't, you know, which I was devastated about. But a bit of therapy and all of that good stuff. It took another six to twelve months, but after after quite a lot of therapy, I did get to a place where I could start to I didn't unwind properly, because obviously you can't because you're still in the trenches, right? But I certainly started to calm down a bit and and think, right, this is no longer life or death. This won't have been a 15-year waste of time, but you know, I I can hold my head up a bit.

SPEAKER_00 21:29

What I find interesting about your story is most people assume the hard inner work happens during the struggle, but for you, most of that work and therapy came after the business became successful and you had crossed that that milestone. You also said on another podcast that your therapist helped you stop chasing the dragon. What is that dragon?

SPEAKER_01 21:52

I set myself a target to have a successful business. One of the mistakes I probably did make at the outset is not define. What success was for me, it was control and independence, but that has so many that's so vague because I hadn't said, Well, when I have X amount of money in my bank, that means that I'm going to be happy. And maybe even if I had said that, it wouldn't have come true anyway, so it probably would have been a nonsense. But I think the dragon that I was chasing was I suppose not ending up back in Dagenham. I used to have a recurring dream about ending up back in Dagenham. You know, the things that happened in my childhood coming back to haunt me, being weak, getting beat up, being socially ostracised, not feeling like I did have anybody who had my back, right? These were all things that wrongly, definitely wrongly, taught me that well, the only person you can trust is yourself. So I suppose the dragon that I was chasing was me. I was trying to get to a point where I could genuinely look at myself in the mirror like I'm looking at myself on this podcast now, and say, So you're okay, mate. You're okay. You were safe, right? I had to get the circumstances of my life to such a place through mega amounts of control, control freakery, channel everything in and discipline over all these years to get to the point where I could go, right, I can now I only look at my to-do list for an hour a day now, right? I used to look at it all day, every day.

SPEAKER_00 23:19

So you had some financial relief earlier, but did that not change the way you worked at all? Like were you still getting up, building the business, like growing it?

SPEAKER_01 23:30

I suppose what it did is it it took the pressure off of me in the sense of I think one of the things John would say if he was on this call, he would say, so I was probably still being too risk averse for where he had got to, because he was struggling to recognise that he had made progress. You know, when I met him, he was maybe at the foot of the mountain, but now he's at like, I don't know, using an Everest analogy, he's at base camp too, right? He doesn't seem to be celebrating that. He's certainly not acknowledging that, let alone celebrating it. I I I've got to do something here to get him to the point where he doesn't feel like everything he's done has been for nothing, but equally not set him up so much that when I call him up, he's on a yacht in the Bahamas, you know. So that was probably the balance, you know, of where I got to. No, you know, you've got to bear in mind my mum was an employee, you know. There were lots and lots of things going on there that were Simon, is it was a running joke, and I didn't give myself this name because I'm not that much of an asshole. But people call me Mr. Fundapedia, right? And and and I took that as a joke, but I also took that very seriously, right? I am Mr. I've I've I've made promises to these individuals that were I don't, I'll be honest with you, I don't particularly care about HSBC, right? They're a big bank. They don't I let me put it this way: I care about HSBC as much as HSBC cares about me, right? Which is not very much, but I do care about the person that I made that promise to. I said I'd get that JSON file from my system to that system by Friday. It's happening, right? So there was a lot of like the macro view on it is that I don't let myself down, but then the the the micro view on it is I've got lots of legal and non-legal contracts with lots of people, and I'm not just gonna not fulfil them. I'm not that guy. I you know, some people might have taken that money and gone, that's enough, I can tap out now, or at least tap down now and take, but that wasn't me. I left my foot well and truly on my own neck until the end.

SPEAKER_00 25:32

And you ran the whole exit process by yourself with your chairman and Chat GPT. What did it feel like to negotiate really a life-changing deal on your own terms? And were you genuinely prepared to walk away from it if it fell apart?

SPEAKER_01 25:48

Yeah, I'd tell you now, I would have. I I I I might have told the story on the other one about how the people that were working for the firm that bought us were inherently fair. They really were. And I and I just wouldn't bring it up if they weren't, right? I'm not gonna 2020 or try and be like disingenuous in hindsight and say, oh, they were really good guys because they gave me a load of money. I just wouldn't talk about them. I'd rather say nothing than than hold a mistruth out there for how they treated me. They were fair, and the way that they ran their operation to bring Fundopedia into the business was there's no such thing as perfect MA, but they ran it fairly, and they never at any point did or said anything. They themselves made me want to say, screw this, I'm out. But lawyers and accountants don't play those games, especially lawyers. And there was one time, and again, this is not the buyer's fault, a lawyer asked me to do something about an employee's contract. We were maybe three weeks away from closing the deal, so we shut we closed it on the 28th of May, and I was downstairs, and uh Leanne, my wife, was in the background because she's as you can imagine, motivated to stay in the loop because she was also head of marketing for the business, right? So she wasn't just uh an innocent bystander and all of this, she'd really poured her heart into the last few years of getting the business where she got it to. And one of their lawyers asked me to do something with one of my senior members of the sales team's contracts, and and I remember saying, No, I'm not doing it. And he said, Well, the problem is, Simon, if you don't do it now, bear in mind this is the lawyers, not the buyer speaking. Problem is, Simon, if you don't do it now, then once the transaction is complete, we lose all of our leverage. I said, Well, call the deal off then. I don't remember thinking very much about how I felt at the time, although I genuinely would have, but I do remember looking up and seeing the end stop what she was doing and turn around and look at me with the most, oh my fucking god, what have you just done, face ever? Which I I I I love. But I meant it, Melissa. I I I truly meant it. There was no way on the way out I was turning over a member of staff who'd been like maybe not served with the business for for as long as some of the guys. I'm really blessed that I had guys working in that business when it sold that have been with me since they left school, like nigh on 20 years ago, right? Which I take as a massive positive in terms of how they see hopefully me and by extension the business. But no, there was no way I was gonna let that happen. And that's one event that sticks with me only because of more of the reaction of Leanne's side than anything else. I just remember her face, like she nearly dropped whatever it is she was doing, right? But there was loads of that on the way through, and and I suppose it's easy to say that because also it wasn't a forced cell. Like, we we didn't need to exit. The business was insanely like it was doing well, and I think we were on the trajectory that I'm not sad about when I got out because AI and cybersecurity and all the things that are now every time I load up whatever your preferred podcast is you hear about, right? Which terrifies me, including the ability to write software in a weekend that would have taken me a year five years ago, right? So I'm not unhappy about when I got out, but we were a data company, so we I'm not saying we were totally shielded, but the value of the business was in the IP and the data. I probably could have pushed it for another year, you know. So I felt like we could have kept going. And worst case scenario, I would have carried on working with some great people for another year or two, you know. Like we we we turned down an offer the year before we did sell, and I always described that as like finishing a marathon and then being asked to run another 10k like the next day. Well, fuck, if you can do that, you can probably run another 5k, you know, like just keep going. I would have kept going, and and I wouldn't have been sad about it.

SPEAKER_00 29:45

But when the deal closed, you cried. So were those tears of joy, relief, sadness, like all of it? Or what was that?

SPEAKER_01 29:54

I wasn't sad about it. Um, it was relief. I mean, I'm still processing processing it now. One of the um best bits of advice I was given after the sale was that for every year that you spent in the trenches, you need a month to decompress. Imagine you're a deep sea diver, and if you try and come up for oxygen too quickly, you will get the bends. I tried to come up for oxygen way too quickly. Like I was I can just go and swim at the surface now, catch some rays and come up from my you know, deep sea where you you know, where you got the fish with the the light on the front of them, the weird-looking monsters. Um, I was down there with those guys. It was it was so weird, Minnesota. I think you've had an exit, right?

SPEAKER_00 30:36

Yeah, not as big as yours, but I had some financial relief as well. Hey, I want to take a minute to talk about the thing that makes my life and this podcast possible. My own company eWebinar. Here's something no one questions. We expect every piece of content in our personal lives to be available on demand from this podcast to our favorite TV show. But when it comes to business webinars, whether it's demos, training sessions, or onboarding calls, anything where a live person has to show up and deliver content, we're still asking people to be somewhere at a specific time on one specific day, hoping they'll make it, and it just doesn't scale. The average attendance rate for a live webinar is 30 to 40 percent. That means the majority of people who want your content never see it. Prospects who never see your demo don't convert, customers who skip onboarding don't activate, anyone who misses training won't adopt your product. The E webinar was built to solve that. We turn any video into an interactive experience that runs on autopilot 24-7 in every time zone. Your audience joins when it works for them, and our live chat lets you respond to questions in real time or later through email, so every question gets answered and nobody feels ignored. It outperforms live by every metric. Attendance, watch times, engagement, and conversion rates are all higher. When live delivery is no longer the bottleneck, you open up a whole new world of opportunities, and that's the real unlock. You're not just replacing the webinars you're already doing, you're finally creating all the ones you never had bandwidth for. The onboarding series, the product walkthrough, the sales demo for that segment you've been meaning to go after. Come see it for yourself. Visit ewebinar.com to join our demo at your own time. No salesperson required. Alright, let's get back to the episode.

SPEAKER_01 32:31

So I'm talking to someone who will understand this, and there aren't many people who understand this, so it's a weird thing to talk about, right? When you've invested basically most of your life, because I started working on this when I was 16, right? If you add up all the failures, and I'm 43 now, I spent more time trying to get here than not. And you can't really include ages 0 to 10, because that's just a fucking write-off, right? Like, so really, formative years 10 to 16, then at 16 went full bore until I was 42. So there's no way that you can have a an event, however big the number could have been 10x what I was given, and then suddenly go, Great, I can relax now. Like, you're just not gonna, right? It's just impossible. Your body's gonna you're gonna wake up the next day and the next day and the next day, and your body's still gonna be going, Oh right, like the levels of cortisol in my body were high, like they would be in any kind of fight or flight situation for decades. So no, there was no instant relief or happiness or sadness. I did cry when I had the phone call in this room. I remember going downstairs and saying to Leanne, it's done. And then I had a big old cry. It was more a cry of just letting out twenty five years of maybe even forty-two years-ish, of pain and self-loathing and disgust with you know who I am and torment and and overthinking everything and like literally 20, 30 years of just everything I wished for for young Simon that I could have just got done so much quicker, but didn't. But thank goodness I got it done ultimately, you know, like that was what it was. It it wasn't yeah, I'm loaded. No, it was it still isn't if I'm honest, Melissa. It really isn't. Like it the the money is a happy side effect of what I did. To have done it purely for the money wouldn't have yielded the same outcome. I I did it because I hated I I was angry. It was an anger I I did it to channel anxiety and anger into something, because otherwise I would have just gone down the pub and blown my face out and been dead by 40. So I d rather than that, I just channelled it all into a business that thank God I met the right people along the way that got me, you know, we all got where we wanted to be.

SPEAKER_00 34:56

I mean, you said something to me that I think a lot of successful people feel, but no one says out loud, which is once you have money and options, you're no longer allowed to be sad. Like, tell me about that.

SPEAKER_01 35:09

Because I am sad. Not allowed to feel sad, you're not allowed to tell all right. I mean, there's just so much to unpack in that one silly little statement, right? Like, all your mates are still working, they're starting there, right? We've all got mortgages, relatively young children. I'm only 43. Some of my mates have got babies, you know. They're all up against it, they're all staring down the barrel of working until they're at least 55, 60, 65, depending on where they are and things. They're all subject to the same things that everybody is, social media, this thing that you touched on earlier about how success should be a two-year thing, right? Well, guess what? That applies in the working world too. Why aren't you a VP yet? Why aren't you a director yet? Why aren't you this, that, or the other? Why aren't you earning six figures? Why, why do you only have a five-bedroom detached house in Kent? You should be living in Belgravier. Like, like, all of these expectations sit heavy on their shoulders too. So there's a lot going on there. There's having to be careful about how I manage interactions around money, right? I want to do fun shit that costs a lot more than they can afford. I lie sometimes about what stuff costs me so that they will come and I let them contribute towards it. So this isn't really directly directly answering the you can't be sad, it's more how do you manage the interactions to your friends that haven't had an event like the one that I'm so fortunate to have had, right? And I know they know that I'm lying. Hey man, I've got a spare muse ticket. Do you want to come to Brixton Academy? No, I haven't, but I'm gonna go and buy a go-go and spend 500 quid a ticket. Do you want to come? Like that'd be the real chat. And he would go, I'm not letting you spend 500 quid on me. This was for my cousin literally two weeks ago, right? He's like one of the best concerts he's ever. I I cried at the concert because I know how much that meant to him, right? And and I enjoyed it, don't get me wrong, but I got so much joy out of him being there with me. And he wouldn't have come if I'd said, Do you want to spend you know that on the ticket? Because he would have said that's nonsense. And he wouldn't have let me do it either, right? Because he's got pride like me. It feels like years pass between speaking to some friends and I have to remind myself that they're all so busy. That's a weird thing. I've got all day, every day, if I choose to, to sit down and do nothing. And sometimes I have to, oh, I've not heard from I'm gonna say Sam, right? Sam for like a week. Oh, is he is he upset with me? And I go back through my messages. Have I have I said something, no? I don't I don't think so. Okay, uh, cool. And then he'll text me and go, like literally, it'll always be like this way an hour later, I'm so sorry, dude. Like I've had this and that, and my son's not been well. Oh, okay, cool. And and that had to happen a few times, and then I was honest with Sam. Funny enough, Sam's a real guy, he lives down the road from me. I was honest with him about it. He went, Oh dude, oh man, like that sucks. And and I was like, Yeah, man, but obviously it's on me. It's like, well, yeah, but I see how you get there, like thinking that people have fallen out of you because they're not talking to you, like, or you've you've not heard from them for a week or two. I mean, the irony is that I don't hear from my dad from one month to the next. So, like, yeah, there's some weird dynamics going on with all of that, but um, there's the comms, there's the money, there's the I don't go and talk to them, and like you can't have a chat with them and be like, my wealth manager's trying to charge me two percent a year to manage my money, and I think the fee drag on this is too high. What do you think, guys? Don't say that one, as if so, and then obviously, you know, you still have births, marriages, and deaths to contend with. It's so hard, right? Like, everybody knows that I'm bloody loaded, right? Everybody knows, or at least expects, therefore, that I am living the life that they would live if they were bloody loaded, right? Because most people would sit there and go, Well, if I had that amount of money, you better believe I would be doing this, I'd have that, I'd go and buy this. I don't like my car, I'd change my car, I'd change my house, I'd change my wife or husband, you know, like everybody in their head has got a sit a to-do list that they will, when they're having a beer or whatever, sit there and go, I'd be I go to Magaloof, I would I like all the I buy a Pierre de terre, whatever it's called in London, like a list. Everybody had like I had it when I was building the business. Reality is when you get the money, you do do that. I did do that. I got I got private shopper to the four seasons at Hampshire and took my mates, you better believe I did. I went shooting while drunk and for shit champagne. Like, I did all of that, you can't do that forever. So suddenly, you so you have this massive peak of really cool things that you do, but then real life starts to set in, my foot hurts. Well, I've not been well recently, I've got a cold, you know, and and so but it is a job to make sure that you manage your relationships, and and the thing that I am most privileged to have, I I'm quite lucky and good at making new friends. Uh, it is a bit of an art or a skill, however you want to put it, but equally, I'm absolutely conscious of the fact that I've got friends that have known me since I had fuck all. And those relationships are so valuable because they will. I said something you you know, you were just saying you can't say that. I said something, it wasn't that, but I said something similar to that to a friend about three months after I sold the business, and I won't tell you what C-word he used, but you can use your imagination, right? He went, boo-hoo, you C-word, and now that's a running meme between us, right? Because I'll go to I'll be like, Oh Tom, I was just about he went, Oh, am I about to boo-hoo you? And and you can't put a price on that level of anchorage to reality. Like, I'll be like, Oh, it's only five brands, it's not only five thousand pounds, Simon, it's five thousand pounds, mate. It's a lot of money. And and it's also you know, talk about managing relationships. I've got 12 years old, I'm pointing because he's still on bloody school holidays, because he's at private school, so I seem to pay more and he doesn't do as much education. He gets a three-week Easter break, right? So he's still in there, bless him. Uh and not at school, frustratingly. But I have to manage it with him too. I I've lied to him. I said, You're not getting any inheritance, mate, just so you know, you're not. And by the way, uh, we were driving in the car the other day. I said, Do you do realize you're in the top 1% of wealth in the not in this country, in the world? He was like, What? I mean, yeah. In fact, I think you're probably in the top 0.1% there or thereabouts. And he couldn't get his blessing, he's only 12, he's quite grown up, but he couldn't. It's like, what does that mean? I said, Look, we'll sit down and have a longer conversation about this when today, maybe tomorrow, maybe when you're a bit older. But you don't, you don't know me. You have no idea where you are in the world. You've absolutely won the lottery. Like, you just have, you know, like to have the things that we've got and to have a dad that can now be around the way the way that I am is just ridiculous.

SPEAKER_00 41:57

Well, he'll uh he'll enjoy this for another decade and he'll have it handed to him later.

SPEAKER_01 42:02

Maybe, maybe not. I mean, we'll see. My I'll be honest with you, Melissa. My aim is to try and spend most of it before I die. I'm not joking. Spend it or give it away, that's for sure.

SPEAKER_00 42:12

Well, you've got quite quite a few years to go. I mean, how do you think about passion and purpose and happiness now that you are financially comfortable?

SPEAKER_01 42:23

So I'm still passionate if you can't tell. I don't necessarily find purpose in business anymore. I'm not saying I never will again, but I I did look for it towards the end of last year. And every time I got close to it, it was like a bit like going to Chernobyl. Like even with a hazmat suit on, I get there and I could feel the radiation of the yeah, and it was a bit too real watching founders struggle with what I've been through and seeing them struggle with it, and and knowing viscerally what they're going through. Their VCs just turned them over, making them shut the business down, for example, or they just can't get sales through the door fast enough because who knew enterprise sales takes years? Well, you should have, but here we are. So I tried to lean into finding purpose back in work because that was my it's a bizarre again, a bizarre contradiction, but like a safe space, or certainly a place where I could channel my anxiety and realized over Christmas when I nearly had a panic attack because I was sat down with somebody and they started telling me some stuff. You ever had a panic attack? No. Oh, you're blessed. Keep it that way.

SPEAKER_00 43:29

I plan to.

SPEAKER_01 43:30

Yeah, too. Once you've had one, it's like a door that you can't shut again. So I've only had about only I've only had about four in my lifetime. But once you've had one, you you can spot the early warning signs, and as much as you would think, well, that would mean that you can then take steps to avoid it. It doesn't work like that, unfortunately. A panic attack that what once that door's open, you can't shut it, you will just get sucked back through it again. So you have to work even harder to stay away from the door, if that makes sense. Well, in the run up to Christmas, I nearly had one. And I had to I had had seven coffees. It was partly my fault. I was off my face on caffeine. But again, I was only using that as a mechanism to get through all these meetings that I was booking for myself because I was thinking, right, I'm going to go back and let's do this. And this is how I used to be, right? And it's about after I had that night near near-miss panic attack, and I was in a public place too. It would have been a right disaster. That I was like, right. I know you need purpose, and I know you're looking for passion and purpose. And I know that you could help these people. So I really do. I get it, right? With all of that knowledge and obviously the money you could invest too. I get that you want to go back there, but it's that whole for each year that you were there, you need a month off. You might never be able to go back there again, right? Let's just start there. You might never have it in you to do that again, but you can't be without purpose either, because that's just going to create an absolute idiot, right? You're going to blow yourself up. So what are you going to do? So I went away and I I wrote a business plan for myself in January, right? And and and listed a bunch of things that I'll pull them up now, actually, rather than um just wing it. I set some goals for 2026, and these are going to sound so trite and boring and self-kind of indulgent, but it's all I had when I was sat in January thinking I can't just not have a plan because then all of that energy isn't going to go, it's it's only going to go somewhere bad. And that bad could be as bad as negative thoughts and overthinking, or as bad as alcohol and drugs, right? Which I just can't have. And would be such a shame and a waste of life given where I am, right? I I now feel this enormous sense of responsibility to maximize not just the longevity of the amount of time. I kind of want the 20 years back that I gave up, if that makes sense. Like I kind of want to go at least one for one ratio on the years that I put in to the years of upside. So anyway, just reading off the stuff on the list. I wanted to join a band. I used to be in the band when I was a kid. I can play a bunch of instruments. So I've rejoined a band, a metal band, as a drummer. I set myself a target to play 10 gigs this year. I want to run a half marathon. That's going to be a thing. I want to do a half iron man. Building the car. I am meant I'm again, I'm just about to contradict myself. I am mentoring two businesses, but I'm doing it on the basis that I've been able to be honest with them that mentally I can't go all in. So if anytime they email me or text me or call me and I'm not around, I'm sorry, guys, you've just got to accept that. And they've kind of accepted to work with me on that basis. Had they not been up for that, I would have said, well, then I can't help you. But they're kind of happy to have as much as I can give rather than nothing. So I had to kind of manage that. I'm working on a book. I've got a blog that I'm kind of I'm doing that whole write a load of blog posts and I'll turn it into a book one day rather than just sit down and try and write a book. I want to rent her a chess tournament. I love chess. It's a bit of an addiction, if I'm honest. And I want to rent her a poker tournament, ideally in Las Vegas. Because again, I just love, as you can imagine, the whole thing that scratches my brain. So yeah, that for me is across like physical and mental well-being, those targets. And I treat those everything I just listed there. Some people would go, well, they're nice hobbies. My brain doesn't work like that. My brain's like, they're now getting done. Not, I'm not gonna die trying to run a half-mouth, and if I don't feel well, I'll just stop. Right? It's not it's not that level anymore. But certainly, that's my job. It is my job, and if I get to December and I haven't ticked off most, if not all of it, I'll say, Well, I didn't do my job this year. I've got to do better next year. You know, that's that's just too right, unfortunately.

SPEAKER_00 47:57

Well, last question for you looking back across your entire journey, what's the thing that you're most proud of?

SPEAKER_01 48:05

I suppose the obvious answer is not having given up.

SPEAKER_00 48:10

Yeah.

SPEAKER_01 48:11

I got sued for a million quid, most people would have given up. I lost good members of the team at critical points that could I could have given up then. I had a cancer scare. I thought I had lymphoma, got this gnarly little scar on my neck that you can't see. It's about then that I was like, I really am killing myself here. If if my immune system is so broken that the doctor's misdiagnosing me with cancer, I've I've got to stop. But I didn't, you know, some people would have gone, my health comes first. I went, nope, my health doesn't come first, actually. It's not even second often. It's it's it's nuts, right? But some people would have like I had so many things go wrong and sideways I could have absolutely leveraged as a reason for I better stop now. I'm drinking too much to numb the pain of all the stress. I've got to stop now. No, no, I'll wake up on a hangover and I'll get on a call and I'll do the demo. I booked in a demo for nine o'clock. It doesn't matter that I've only had three hours' sleep, I'm doing the demo. The demo, and Leanne used to say to me, Mrs. S, I can't believe you did that demo this morning. You were drunk last night. Like, how did you do it? It's like it was non-negotiable, Lee. Like, it's sorry, what part of non-negotiable do you know? So I suppose that the second thing that I'm most proud of though, because it's not just about me. I'd like to think that along the way I touched and and my job, you know, in terms of purpose going forward. I want this just because I'm not doing it through work doesn't mean I'm not doing it. Me doing these other hobbies that I'm talking about, they're not all just about self-serving, they're about finding ways to build connections with people and touch people in a way that it emotional connections, right? I I created emotional connections with people, I'd like to think, or at least I felt it, I'm sure hopefully they did too. Be that staff, be that clients, be that other fintechs that were in the ecosystem, who I could just say, dude, keep going, it's gonna be alright, you know. All of that, right? Helping people through tough times when they were employees, lending them money, even without the money, just telling them that they're doing a good job. In whatever format it came in, I'd like to think I might be wrong. I always wish that when you walk around, you know, like in the Sims, you get the stats above their heads. I wish that that was a thing in real life. Because I'd love to know like whether I'm well out on the number of people that I've I I had an emotional connection and impact on, you know, like and loads of people did it for me too, right? It's not a one-way street, but I'd like to think emotionally I connected well, put it this way: one of my guys was at a conference yesterday, and he texted me after the conference and said, Loads of people came up and asked, Where are you and how are you getting on site, right? And I took that and I joked, I obviously being me, I wrote back and went, I would be told to piss off and leave me alone, just as a joke, right? Obviously, but on the inside, I went, Fucking hell, that's amazing. Like they they actually really like me. Because obviously in my childhood I didn't have anyone like, so yeah, I'd like to think that I left a mark on a few people in a good way, and and and I think you know the the two things are interlinked, right? I never gave up because I saw those little glimmers of connection, and they're addictive. I um you know I was addicted to that those things being possible and wanted to have as many of them, and I still do want to have as many of those little fleeting moments of connections with other human beings as as as as any one person can before I die, you know, and and that's I'm proud of that. I'm proud that I have that mentality.

SPEAKER_00 51:54

Well, Simon, thank you so much for coming on the show and taking the time to share your story. That's a really good one.

SPEAKER_01 52:00

Thank you for giving me the opportunity to, and obviously I hope that it helps anybody else out there who's uh on their own journey.

SPEAKER_00 52:11

Real quick, if what we talked about today resonated with you, the best thing you can do to pay it forward is to share it with someone you think would enjoy it too. The only way this podcast grows is by word of mouth. Whether that's a review, a post, or even a text to a friend, it would mean the world to me and would help me keep this podcast going. Hit subscribe so you never miss an episode. And head over to profitled.fm for show notes. If you want to connect or share feedback, I'd love to hear from you. Find me at melissaquan.com. That's M-E-L-I-S-A-K-W-A-N.com. Thanks for listening. Bye now.