I’ve been self-employed for over 15 years. In that time, I’ve started businesses, closed businesses, sold a business, built things people loved, built things that couldn’t pay for themselves, lost people I thought were irreplaceable, and — here’s the important bit — I’m still here.
This isn’t a highlight reel. It’s the opposite. These are three stories about failure, and what came after.
The person who left
Systemato weathered Covid well. We adapted, kept going, came out the other side in decent shape. Then, just as things were winding down and it felt like the hard part was over, a key person — a right-hand pillar of the business — left. Suddenly.
They couldn’t accept that the business had changed. Their role needed to change with it, and they couldn’t bear that reality. So they walked.
If you’ve ever lost someone essential to your operation, you know the feeling. It’s a gut punch. Not because the work can’t get done — it can, eventually — but because you trusted the structure, and the structure just cracked.
Where I failed:
- I failed to plan for people leaving. And that’s on me. Circumstances change. People want a change. Relationships sour. People leave. It’s not a possibility; it’s a certainty.
- The failure was not dealing with it before the fact — not having a plan for the inevitable. You should always be prepared for anyone to walk out the door at any time. I wasn’t.
What I learned:
- I’m still here, aren’t I? New people came on. The business took a swerve rather than a hit. We adapted, evolved, grew new areas, trained new people.
- What felt like a catastrophe became a catalyst. The lesson: plan for departure, absolutely — but also trust that you can rebuild. You can.
The product nobody could pay for
Gallarija was an AI-powered property search engine that scanned the internet and brought all property listings in Malta into a single website. Zero fees, zero commissions, full transparency. Your lookout for property in Malta.
I built it with a friend because we were geeks who wanted it to exist. We couldn’t find one like it, so we just built it. It had a real, loyal userbase. People loved it.
The problem was that love doesn’t pay invoices.
Where we failed:
- A product is not a business. As geeks, we built a product because we thought it would be cool to have, not because it was a business. We never figured out how to monetise it without making the product worse. We failed to think about monetisation from very early on — not later, not eventually, from the start.
- And we made enemies of a bunch of estate agencies whose business model we threatened simply by existing. We hadn’t anticipated that either.
What I learned:
- Never start a business without a clear path to profit. Full stop.
- I learned all about machine learning, back in 2019, before AI was a buzzword on everyone’s lips.
- I learned how intractable people can be when you threaten their livelihood.
- And I made good contacts and gained a lot of people’s respect by building something that challenged a status quo many people despise.
To this day, people tell me they miss Gallarija and wish it was still around because they used it every day. That’s worth something. It’s just not worth money.
The business that worked (until it didn’t)
The 3rd business I talked about was a condo management firm that I set up with a friend, bootstrapped and grown entirely organically over five years.
We went from zero residential blocks managed on day one, to over 70 by year five. Entirely by word of mouth. Entirely on the strength of good customer service. No marketing spend. Just by doing the job well.
Sounds like a success story, right?
It was, until it wasn’t.
Where we failed:
- The business model hit a wall. Every time the business grew, we needed to hire more hands to handle the workload, so profitability wasn’t keeping up without compromising on customer service.
- Staff turnover was brutal — you hire someone great, you train them, they learn the job, then the daily grind of problems and people yelling on the phone and actual, literal problems wears them out, and they resign. Rinse. Repeat.
- And then there’s the life part. Two co-founders with babies born four days apart. There comes a point in your life where at 7:30 pm you’d vastly prefer to give the baby a bath and grab a bite to eat with your spouse than listen to gripes about the lift not working in some common parts of some apartment block you set foot in once.
We got tired. We exited, selling the business to a competitor.
Not for any life-changing amount of money, but a buyer was found for a business in a niche that is not glamorous.
And that, in itself, is an achievement.
What I learned:
- Build a business in an area you care about, at least a little.
- Co-founders are extremely important — as Enzo Ferrari’s father reportedly said, a company is perfect when the number of partners in it is odd and less than three.
- Build a business that can be sold, and build it this way from day one.
- And pay yourself first. Keep equity in the company to avoid debt, fine — but pay yourself something, because if you don’t, it will just be a drag and a sap on your will.
- Oh, and when you sell? Know the three numbers: what you want, what you’re valued at, and what the buyer will actually pay. They are rarely the same number.
What got me through
My then-girlfriend, now wife. My co-founders. My colleagues.
And my own internal drive and pigheaded determination to swivel, duck and bob and weave and keep going rather than throw my arms up and give up.
Reframing failure as a lesson is not just a platitude. It’s a survival mechanism. It’s a great way to keep going when the alternative is to stop.
What success actually looks like
For me, success is the fact that I get to choose what I do.
No boss comes and gives me a task. I decide to work on this client, or I decide to set up this business based on this idea, at the time of my choosing, with people I want and like — not who are chosen for me.
That I have the privilege to do this is, to me, a great success in itself. If it pays for itself, so much the better, but the liberty to even try is already so gratifying.
Business, like marriage, is a closed box — as we say in Maltese, you don’t know unless you’re in it.
Without wanting to go down the Instagram post road of “they don’t see the 4 am starts” — it is true that they see the client roster, but they don’t know how long your payment cycle is.
They see your logo in places, but they don’t know what each placement cost.
They think you’re rolling in it, but they haven’t seen your provisional tax payment.
It looks like you have it all figured out, but you’re two weeks away from throwing in the towel.
I don’t mean to sound negative.
Honestly, for the most part of my 15 years in self-employed business, it’s been fun. Challenging, tough, but truly — fun.
And hell, if it were all easy, would it even be worth doing?
