Entrepreneurship in a Nutshell. 20 Years In, Still Building.

10 May 2026 · entrepreneurship, life

2005. I was 23, fresh into my first proper job as a Systems Administrator at SunGard Availability Services in London. Earning a real salary for the first time. Three months in, I had the role figured out and my brain was already drifting. The work was fine. The work was boring. I wanted something bigger.

Then a friend pitched me a karaoke bar. Then it became a karaoke restaurant, because a pure karaoke bar only really makes money on room rental and snacks and drinks, and a restaurant catches lunch trade too. That was the logic, anyway.

Stupid? Absolutely. Exciting? Even more so. That’s how it always starts.

Twenty years later, I have started, run, walked away from, partnered into, partnered out of, and quietly buried more businesses than I can count without using my fingers. Karaoke. Design and print. A family takeaway in a properly bad state. An LED import/export company, many small ideas that did or didn’t work but stopped for good reasons. A dance company that bloomed for seven years until COVID. A dating platform stuck in stop-and-start mode. A small property thing we deliberately kept small. And now an AI business that mostly just runs out of my home.

This is the honest version of all of it.

The First One That Didn’t Open

We found the venue right next to Baker Street station. A basement under Starbucks (Starbucks was also the landlord, brilliant). £70,000 a year on the lease, plus fitout, plus karaoke equipment, plus all the things three first-time founders never thought to budget for. Three of us. All green. All in our early twenties. All convinced we’d figured it out.

We brought in a consultant. He was, in hindsight, the loudest signal that we hadn’t figured anything out. High fees, served himself, added no value. But I was 23 and I wanted to believe people. That belief cost me really really badly.

About a year and a half in, we ran out of money and out of trust with each other. The bar never opened. I left SunGard in mid-2007 after two years of trying to work alongside half a team that did the work and half a team that did fuck all (and a management chain who were fine with that), opened a design and print business with the same consultant on the side, and roped my older brother in to help. We built business cards, leaflets, flyers, anything we could draw and print. The markup on print is genuinely brilliant. We had returning clients. I was learning open source on the side, asterisk and trixbox and DNS and VPNs and CRM, the kind of stuff that becomes a career later when you don’t realise it yet.

Eighteen months later, by early 2009, that one fell apart too. The partner was on the highest salary, bringing in no new clients, racking up complaints from the existing ones, and adding no real substance to delivery. Health problems, spending problems, delivery problems, every kind of problem with no solution attached. Only problems and more problems on top. I walked. Three years in (counting from the karaoke). Massive debt. Bank loans, family loans, friend loans. Every penny I had ever earned was already gone.

Rock Bottom

I do not want to dress this up.

There were nights I did not go home. I was too embarrassed to face anyone. I slept rough on the streets of London, just to have somewhere that didn’t feel like judgement. Funds depleted. Spirit and morale at all-time low. The thoughts of suicide showed up. First time in my life. Not as a plan, more as a really loud option in my head, and I genuinely couldn’t see any clear way out. It was 2008. I was 26, broke, ashamed, exhausted, and out of moves.

I moved back to Birmingham. To my parents. Tail between my legs.

The thing about rock bottom is it holds. Nothing under it. The only way from there is up.

The Takeaway Years

By late 2010, my brother and I took over the family takeaway. It was in a properly bad state. Mismanaged, neglected, near bankrupt with bailiffs chasing debt, knocking frequently on the doors. We spent four years turning it around. Not by being clever. By doing the boring work. Watching what worked, watching what didn’t, changing one thing at a time. There was no Google or YouTube or AI to ask. You had to learn slow, and you had to be patient enough to wait for the result. Should also mention working with family came with its own challenges too. I now understand the saying, “don’t work with family.” Lol.

Somewhere in that period, another friend invited me into a fresh venture with two other partners (you would think I’d have learned). Three years of people saying “I’ve got the kids, I’ve got the day job, I’ve got something else on, I’ll get to it soon.” I’m sitting there going, mate, I have all of that too, and I’m still showing up. Three years (2009 to 2011) travelling back and forth between China and Taiwan. Mostly wasted. The lesson finally hit me: I’m genuinely terrible at picking business partners. I still remember juggling 3 jobs at one point back then. I nearly fainted at work from the burnout.

The recovery started small. I made one decision. Stop feeling sorry for myself. The only person who could fix this was me. So I started running. Every day, for two years. I started reading (the twenty-year reading list is over here, if you want the trail of crumbs). I learned to dance. I went scuba diving. Sailing. Windsurfing. Wine tasting. I started travelling, properly. I started doing things on my own. The hardest one was learning to be selfish, because it ran straight into my ego and my idea of who I was supposed to be. But once you’ve hit rock bottom, the only direction is up, and you stop waiting for other people to make your life happen.

When the takeaway was healthy again, my mum told me to sell it. She is the one person in my life who has never worried about me, because she always saw me out in the world, not behind a counter. So we sold. I travelled for six months and came back trying to figure out what next. I’m finally free.

Bloom and Burnout

By 2015, a friend got me into ICT infrastructure work in the building services sector. Eighteen months. Brain absolutely cooked. Tough industry, fresh in it, the pay wasn’t great, but I learned an enormous amount very very quickly.

Then I started a dance business. This time, I picked the partner. On my terms. Around the same time, I went back into the data centre world. It was easy and innate, the kind of work I’d been passionate about for years when it came to hardware and infrastructure (it was my actual home turf). That career properly took off. The ICT designer years had quietly built me a project management muscle and a delivery rhythm I didn’t know I had, and it made a real difference.

In parallel, I tried to help my wife start an Amazon reseller business. We worked through paid programmes and friend introductions. The big lesson there was about prototypes, MVPs (minimum viable products, the rough thing you ship to see if anyone actually wants it), and getting interest first instead of trying to perfect a product. Selling something nobody wants is much much harder than selling something people are already asking for. Plenty of failed products, plenty of laughs about it later. We closed it when she moved on to her own thing and I was already running a job and a dance team.

The dance business bloomed. We just kept building it because we cared about the scene and figuring out what would add value to people’s lives. Brazilian Zouk, all-inclusive dance marathons in Ustron, Poland (the kind that nobody else was running properly back then) and well-refined dance programmes with progressive learning and practice all packaged properly together. Seven years in, we were 15 people on the planning side alone, and the scene was paying attention. Then 2020 came, COVID arrived, totally fucked everything. International staff and no UK building meant zero government help from anywhere. I burned out. That was the moment I decided I genuinely never want to pay tax in this country again, but that’s a separate rant.

Inside COVID I tried to put a team together for a dating platform. Same problem as always. Nobody could carve out the time (even though it was COVID and no one had anything better to do or wanted to do anything!). The idea has been on ice for years now, but I still believe in it, and AI changes the maths on whether I need a team to build it (the full story of that one lives here).

We also built a small property portfolio. Once UK tax law and the Renters’ Rights Act started rewriting the maths, we stopped expanding. Small and steady. The full case study with numbers is over here.

Now

So that is twenty years. Six or seven proper ventures, depending how you count, plus a couple of side bets. Lots of pain, lots of money lost early, lots of scars. Blood and sweat. Had my second midlife crisis already, for what it’s worth. Do I regret any of it? Not at all. Frustrated at times, yes. Never angry. Every one of those failures became muscle. Every wrong partner taught me what to look for in the right one. Every empty bank account taught me what I would actually do with the next one.

Twenty years on, in 2026, what I am building now is a small AI business. The reason it is small is that I no longer need a team. AI does the work of three or four people, if you set up the harness around it properly. (I built that, it is called SST3-AI-Harness, and most of what I do runs through it.) Most people can’t keep up with me, because I’m just too fast at getting things done properly. And picky as hell about the work. And high energy. I don’t accept subpar quality or poor implementations, ever. Recently diagnosed ADHD and OCD, both of which I’ve had all my life apparently, both of which now make a lot more sense as why I am the way I am, through better and worse.

What I have actually learned about people, after twenty years of asking them to build things with me, is this. Not everyone is cut out to be an entrepreneur. Entrepreneurs are a completely different species of human beings. We’re survivors. We fight. We grind. We do what it takes to get things done. We try not to lose sight of the goal. We push limits because nobody else will. We innovate. We create. We take risks. Sometimes we fall or fail, but we always dust ourselves off and get back up trying.

Would I take a business partner again? Of course. If they’re the right breed. If they’re a real entrepreneur, not a wannabe. Everyone has ideas. Not everyone has the will, or the ability, to turn one into reality. As an entrepreneur you need to be able to learn, and learn fast (learn how to learn). You don’t get to have excuses. You’re accountable for everything, every decision. You need urgency to get things done or figure things out. You need grit, a lot of grit. And unless you’re willing to go through all of these, you’re better off sticking with your day job.

Learnings

Confidence, it took me quite a few years to learn this one. I always thought I was the problem, turns out it wasn’t. The reason why everyone wants to partner with me is to leverage my intel, skills, drive, and abilities. I thought I was dumb and there were many people who were more capable. Turns out there isn’t, and it’s all in my head. The reason things get done and I am where I am today, is because of me. Not others.
Be picky with who you get in bed with (finding a business partner). Drop them quick if they are dead weight and red flags are showing early on, it’s like being mis-sold a product or service, terminate it! Before they suck any more of your energy and soul.
Choose fairness over equal when it comes to partnership and rewards (what are they able to offer and bring into the team; investments, equity, salary, bonus, time, skills, energy, results; all of these need to be weighed).
Communication. Be vocal, if something is wrong, talk about it, and it’s better to deal with it earlier rather than later. Working with your team or partner is about being able to talk about uncomfortable subjects and matters and work together how to deal with it. Don’t drag shit out.
Trust your instinct, if something smells like shit, looks like shit, then it probably is shit. This goes for everything: listening to people, salesmen, adverts, product descriptions. Learning to spot bullshit became one of my superpowers.
Don’t give up. The moment you do is when your dream’s over. This doesn’t mean keep doing the same thing and hoping for a different result.
Building a strong foundation in any skillset or knowledge, or infrastructure, is important and it takes time, a lot of time, focus on the basics and keep things simple, and do those simple basics very well. Don’t go for quick and fancy, like the next fad or get-rich-quick schemes. Build things that last and offer real value.
Risk reward management, probably an important one. If the reward is not worth the risk, don’t take it. Risk only what you can afford to lose. Write it off immediately once you’ve invested like it’s money already gone.
Spend the time to prototype, build an MVP, test the water before you invest any more time and money.
This probably hits a few pointers above, scalability. Do something that can be scaled, whether through automation or manufacturing or workflow and processes. You want to be able to refine your product or service and ensure it’s able to reproduce the same results every time and roll it out. This helps bring costs down later and grow your profit margins.
Don’t take money from friends and family unless you absolutely have to. Losing your own savings is one thing. Losing theirs is much much harder to live with. I borrowed from friends and family for the karaoke and the print business. When it all went to zero, that debt was the one that hurt the most.
Pursue what YOU actually want, not what the world calls “success”. Big dreams and making tons of money were what I thought I was supposed to chase. The mindset shift that pulled me out of rock bottom was deciding I’d rather build a life I actually wanted, not one that just looked impressive from the outside.
Look after your health. Burnout is a real cost, not a badge. I worked through 3 jobs at one point, fainted at work, and then sat through a COVID burnout that flattened me. None of it was strategic. All of it was avoidable if I’d treated rest as a non-negotiable.
Sometimes solo is the right answer, not partnership. I wasted years waiting for the right team to assemble itself for ventures like the dating platform. AI changed the maths on what one person can build. Some ventures need partners. Some don’t. Knowing the difference saves a lot of waiting.
It’s okay to fail. I’ve done it a lot of times. Out of all the business ideas, only 3 succeeded in my life so far, and that’s enough. Even with the successes, I’ve exited them to move on to bigger and better things. Everything is temporary anyway. You can choose to move on or not, for whatever the reason, or when the time is right and it’s time to let it go.