My first business cost me my tuck money. That turned out to be the cheap lesson.

At 15, I was a student at Falcon College, where we didn’t have a tuck shop. What we did have was a lot of boys who wanted soft drinks, and sportsmen who wanted Energade after training.

I had tuck money. I could have spent it on myself. Instead, I bought drinks to sell to everyone else. For a while, that meant I was surrounded by refreshments but couldn’t treat them as mine. I had put my money into the business, and I needed it back before I could spend anything.

It was my first lesson in supply and demand. I could see what students wanted, buy it and make it available to them. Then I realised the demand existed beyond Falcon. A friend at Peterhouse began selling drinks there on my behalf. He was my first employee, or perhaps my first business partner. At 15, we weren’t too concerned with formal titles.

He helped me reach a second market without being there myself. But reaching more customers also meant making sure we had enough drinks, and that the drinks we offered were the ones students actually wanted. I was learning about expansion and about serving a market well, though I didn’t yet have those words for it.

Then both schools got proper tuck shops, and our business was finished.

I understood why students went to them. A shop could keep drinks cold and offer far more than I could carry around. The tuck shops confirmed that I’d spotted a real opportunity. They also showed me how quickly I could lose it if someone served those same customers better.

I still think the schools missed a chance to let us run those shops ourselves. I would have loved that job. I might even have bought a fridge.

At 17, my friends and I moved on to selling something we couldn’t fit into a cooler box: a night out. We called ourselves Team Germany. There were about ten or twelve of us, and we organised parties people actually bought tickets to attend.

We’d find a house, imagine what the party could be, plan the night and market it until people wanted to be there. We formed partnerships that helped us get the right people in the room. I loved preparing the venue, watching guests arrive and seeing something we had pictured in our heads turn into a packed party.

We all contributed to the plans, but Dylan, Tino and I did much of the work to make them happen. The wider group made it possible in another way: none of us could afford to put on the sort of party we wanted alone. If ten people each put in about $100, suddenly we had $1,000 to work with. Long before I knew to call it crowdfunding, I’d learned that pooling small amounts of money could make a bigger idea possible.

Before long, Team Germany became a name people knew. We were the it guys, and I won’t pretend that wasn’t fun. But we also thought about what would happen when we left school. We created a system for appointing new members, and being chosen for Team Germany became a privilege. We handed it on to a second generation, then others after them. We would always be the first, but the brand could carry on without us.

Team Germany taught me that a good event starts well before anyone arrives. We had to give people a reason to care, get the word out and work with others to bring it to life. Then it was time for university, and I chose a beautiful, very cold country called Canada.

I landed in Vancouver and found myself working for Savage Entertainment, which put on club nights and other events for university students. It became my first real sales job. We didn’t sit around hoping people would buy tickets. We walked up to groups of strangers at parties, started conversations and tried to sell them tickets on the spot.

The groups of guys didn’t worry me much. The groups with beautiful girls? I suddenly became very interested in the floor, the ceiling, the weather—anything I could look at before making the approach.

I did it anyway. The more often I approached people, the easier it became to start a conversation, listen to them and make the ask. Team Germany had taught me how to get people excited about an event. Savage taught me what to do when the person I needed to convince was standing right in front of me.

Later, I bought a camera and became an event photographer. I liked being on that side of the night too: watching for the moments people would want to remember. I didn’t know then that the camera would become useful in another business a few years later.

I also tried to start an events company of my own in Canada. Oxygen Entertainment managed one paintball event. It was enough to show me how many costs arrive before the guests do, and how much more an idea needs once the excitement of planning it wears off.

My time in Canada ended when I came home to recover from depression. I won’t pretend that was part of some clever plan. I was unwell, and I needed to come home.

When I was ready to study again, I went to Amsterdam for a degree in entrepreneurship and business management. During my second year, I started a fashion brand called Barebanannas. I wanted to make clothes that could help start conversations about mental health, especially among men. I knew how alone depression had made me feel, and I didn’t want someone else to believe they had to carry it quietly.

Soon we had a small team, garments we’d made ourselves, a collaboration with a shop and photo shoots almost every weekend. The camera skills I’d picked up in Vancouver came with me. I knew how to look for a moment, make people comfortable in front of a lens and give the brand images that felt alive.

I was proud of what we created. I was less proud, eventually, of how easily I confused creating with selling.

We could spend an entire weekend on a shoot and come away with beautiful photographs. On Monday, we still had to find someone willing to buy the clothes. Barebanannas made me return to the question I had answered almost instinctively at 15: who wants this, and how do I get it to them? It also made me think about the people working alongside me. They believed in the brand and gave it their time, often without pay. If I wanted us to keep going, I needed a way for the business to support them.

Barebanannas didn’t last, but those people, the clothes and the work we did still matter to me.

After Amsterdam, I went to Thailand, where a former business partner had opened a coffee shop. Working through that venture taught me to understand every business arrangement for myself. A good relationship can make it easier to begin working together. It doesn’t replace asking questions and knowing exactly what I’ve agreed to.

Then I found a hotel, bar and restaurant I wanted to open. I called it The Celestial Crescent.

The annual rent was around €15,000. I had roughly €2,600 to my name. Most of it—€2,500—went towards getting the keys.

Those numbers look as alarming in print as they did in my bank account. Still, I saw 18 rooms and imagined what the place could become. Some rooms needed work. The top floor needed repairs. I moved into the hotel because I could no longer afford to rent elsewhere and began putting the place together piece by piece.

We got a bar licence and opened the bar. A little money from drinks could help us apply for a restaurant licence. If we could serve food, we might bring in a little more. I learned to give every euro a job because there weren’t enough euros to let any of them wander off. Cash flow economics 101.

I also had a staff member to pay. Their salary came before mine, even when that left me eating once a day or surviving on oats and raw eggs. I had enjoyed being the person who made things happen at our school parties. In Thailand, I understood what it felt like when other people depended on me to make the numbers work.

I found an investor who sent money for a rent payment, but PayPal withheld the funds. We missed the payment, and I lost the business.

That loss was difficult to accept. I had managed to find the money, yet I still couldn’t use it when I needed to. I kept trying to make Thailand work afterwards. Giving up has never come naturally to me, and for a long time I treated staying as proof that I was strong. Looking back, I can see how much staying was costing me. Sometimes I need to change course while I still have the strength to do it.

My parents welcomed me home when I was at rock bottom. They gave me the space to recover and begin again, and I’m deeply grateful for that.

I joined Carrick Wealth and started working in wealth advisory. I learned from my colleagues and from a boss who became more like a mentor. I also discovered that I could bring my appetite for building things into a company. When I had room to take initiative and develop an opportunity with other people, I felt like myself.

Outside work, I kept seeing possibilities. My family had a property that was sitting underutilised, and I spoke to my dad about what we could make of it. With his support, we brought it to life as The Celestial Crescent Hideaway. The name I’d given my hotel in Thailand found its way to a new home in Zimbabwe.

I also started building Fixa because I saw how difficult it could be for people to find reliable professionals to do work in their homes. I had experienced those difficulties myself. As the firstborn, home repairs naturally became my responsibility, and I hated the frustration and inconsistency. Above all, if someone did a shoddy job, there was nowhere I could leave a review and warn others about that professional.

To me, that was a big flaw in the market. Without a formalised system for reviews and accountability, poor workmanship could go unchecked. So I decided to build one.

I’m proud of those businesses. I’m excited by what they could become. I also feel the weight of keeping them going.

Sometimes I have no money. Sometimes I have a decent amount in my account, but I’ve already set it aside for wages, repairs or the next step for a business. I can invest it and see a return, or I can invest it and lose it. The decision follows me home either way.

It has cost me friendships and put strain on relationships. Dating can be hard when I want to make plans with someone, but I can’t always afford them—or when I can afford them today, yet know exactly what that money needs to do for the business tomorrow. I don’t expect anyone to find that easy. I do hope to be with someone who understands why I’m making these sacrifices. I’m trying to learn how to give the people close to me enough of my time and attention while I do.

When I hear “be your own boss,” I think of the boy at Falcon spending his tuck money on drinks for other people. I think of how nervous I was approaching strangers in Canada. I think of my Barebanannas team giving their weekends to an idea we loved, and of paying a staff member in Thailand before I could feed myself.

I still want to build. I’m glad I’ve taken some of the risks I have, even the ones that ended painfully. They taught me to look closely at what people need, to work with others, to sell what I create and to pay attention to the money coming in and going out. I’m still learning when to push forward and when a different route might give me a better chance.

I hope the work I’m doing now leads to a breakthrough. More than that, I hope I can build something lasting without always having to live in survival mode.

I also want to thank the people who have helped me along the way: everyone I’ve worked with, everyone who believed in me and everyone who took a chance on me. To our Celestial Crescent guests, thank you for choosing something we’re still building. To my parents, thank you for giving me somewhere to begin again, and to my dad, for helping me bring another idea to life.

To Andrew, my mentor at Carrick, and to Tawanda and Juniel, thank you for your guidance. To my teachers, former business partners and colleagues, thank you for the lessons, opportunities and experiences we’ve shared. You’ve all helped shape the man I’ve become, and you continue to shape the man I’m becoming.

Above all, I thank God—Yahweh—for sustaining me through every chapter, especially the ones I didn’t know how I would get through. Without Him, I am nothing.

If you’ve taken a risk to build something, what did it teach you that success stories usually leave out?