In 1998, I was 18 and had only held summer jobs. I had an entrepreneurial spark but no confidence and no real clue. The one thing I did know was that I didn’t want to be an employee so I became a freelancer. I did not call myself anything particularly, I would have been willing to freelance on lots of things. I loved computers and could fix people’s computer problems. Self-taught from 11 years old. This was mainly trying to get dodgy cracked PC games to work. I had an aging machine and a Cantonese school buddy would get them in a Hong Kong market during the school holidays. I would have stacks of floppy disks and getting them to work was a nightmare! This was back in the day before you could just download stuff. Anyhow, suffice it to say I got a few of them working eventually, and that made me pretty good at fixing stuff on a PC.

I did the odd random job here and there for getting people’s printers to work to wiring in speakers in a pub but mainly friends and family PC problems: they had a virus, their scanner didn’t work or they needed windows reinstalled or whatever. Things progressed and I did a little bit of web design when that came into fashion. I did the odd little website and fixed people’s computers.

I scraped by for years doing this sort of thing, I spent a lot of my time volunteering and did a few little jobs on the side to get by.

One day I woke up from this. I hadn’t done anything entrepreneurial at all – I had created a little job for myself. I was an employee without any employee benefits. This was not what I wanted when I was 18, I wanted a big booming business with plenty of income so I could invest in projects I was passionate about!

I was 25, newly married and had bought a house I couldn’t afford the mortgage on. I had to start to make money or spiral into debt and all the other problems that come with it. Unfortunately, I chose debt.

I started doing a bit more of what I had done in the past, it wasn’t enough and I found myself in a lot of debt that I couldn’t repay. I had to start to make money or go further into debt. This is the point where “I” becomes “We”. My wife started assisting with business decisions and figuring out how we could address our finances. We made a decision to go all in on a deal to buy a business and to triple our debts in the process with the hope that we could make that business make all the money we needed. Wrong decision!

Things started well – We were making all repayments, paying all the bills and living costs and had about 4 times the average wage left over each month. At this rate we would be out of debt in 5 years and have our house paid off in 10 years. Awesome! 4 months into running the new business and it all dried up, people were not buying from us anymore and it went making bank to costing us twice as much as it was once making us. We had some turnover so it was easier to get more credit and go into more debt to try and sort things out – We knew it must be possible as just a few months prior we were making good money. I also hated every single minute of it. Big mistake!

Things kept spiralling out of control until we finally shut the business and had to regroup. We had 10 times more debt than we had when we thought things were terrible! We were bust.

We had to start making money.

And we did.

We made a lot.

We started 3 new businesses practically the day we shut the failed one. The problem was, we made a lot of turnover but not a lot of profit, in fact hardly any profit. When you have a lot of debt, you have a lot of repayments. If you miss a lot of repayments, you get a lot of charges. It can be an uphill battle. We expanded quickly but our backlogs caught up with us. When you expand quickly your overheads can also expand quickly, our projections never fit with our needs.

We soon learned that making a lot of money does not fix the situation. We had three more failed businesses as a result and still a load (although slightly less) debt.

We had to start making profits. We started another business.

And we did. We made some.

We actually made quite a lot, enough to start making headway into our debts. This was the first time we actually made some progress. There was some disheartening news however: at the rate we were profiting and juggling debt and repayments, creating future backlogs to pay something that needed sorting right away and generally having a confused mush – it would be 24 more years before we were out of debt. We had already given our house back to the bank and agreed long payment terms that somehow fit in with our current income levels. We worked really hard that year to make that money and paid off a 25th of our debt. We had 24 years left on our prison sentence.

We had to start making more profits.

And we did. We made more.

With good behaviour, we have cut that prison sentence down from 24 years to 6.

If we continue to improve our behaviour we will be out on debt free parole in 2 years.

We now increase our income by 100%+ each year.

Hindsight may have made my life easier, but not better. I have benefitted from these mistakes and, although I regret any negative effects my actions may have caused others, I am a stronger and more driven entrepreneur as a result of living through them.

What I learned from this:

1. Lessons learned in failure are more important than the ones you learn in success.
2. Having massive repayments due tomorrow creates necessity to do something extraordinary.
3. Taking the easy way out is not an option when you care about your investors.
4. Investors will back you again when they see how you do in adversity.
5. When you are not doing so well, seemingly loft goals are not big enough. We make 4x as much money that I dreamed of making 10 years ago and it is nowhere near enough.
6. Costly mistakes are a form of investment, they teach you discipline and necessity after the fact. When you personally have to remedy them, they also stop you making them again.
7. Even if you completely fail as an entrepreneur, people seek you out for advice – willingness to try and actually go for it are admired qualities.
8. We have yet to have our big successes, but the odds are in our favour because we are playing the game.
9. We never set ourselves up to fail fast and light. We kept straining the same failure for years and made the cost of failure too big. Pivoting became harder and harder.
10. We never leveraged our skills and passions.

• Make sure your failures are fast
• Never get bailed out, bail yourself out so you learn your lessons
• Follow your passion
• Do not personally guarantee debt you cannot repay
• Keep going and improve every time.