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I have a had a few successful businesses. I’ve created a successful sporting goods brand, built and sold a tech startup, and started a popular coffee shop. But those are the odd ones out. I have failed at far more businesses than I have succeeded at.

I don’t regret any of the failures. They took up thousands of hours and cost lots of money, but each one taught me something and helped set my feet on the right track.

Here they all are in one place: my shameful mistakes, my embarrassingly bad ideas, and my naive enthusiasm.

Bet Central

A go to place for all information about betting sites with a focus on in-depth reviews. We would make money from affiliate deals. 

Let’s start with the business that cost me the most money.

For most of 2011 and the beginning of 2012, we spent a lot of time and money trying to build bet-central. It wasn’t a business I was at all passionate about. I had simply heard a lot of stories about gambling affiliates making a fortune from writing reviews and wanted to get involved.

It seemed like a perfect fit. I had plenty of experience in the sector from spending quite a few years arbitraging different gambling sites, a lot of the ‘successful’ websites were rubbish or full of lies, and we had the money to invest.

Despite having almost no interest in gambling for fun, I honestly thought that I could provide some value and conquer this sector.

We spent quite a bit of money on it. Paying for the site to be developed, going to affiliate conferences in different countries to meet their marketing managers and employing a full-time employee who worked on it for one year.

The site was actually pretty good. But there were two main issues.

  1. We didn’t do any marketing and focused solely on content. After a year the site still had almost no traffic.
  2. We got the site built by cheap programmers off Upwork. It looked good but was very badly optimised for Google so we got no search traffic.

Ok. Maybe the site wasn’t that good. Remember how I said we employed a full-time employee to work on the site? Well, he had a masters degree in maths and English was his second language. So we obviously decided to use his skills… and got him writing reviews in English. What?!

We were young and stupid. Check out my super serious business card with our mascot ‘Beppe the bettor’.

bet central business card

No idea why I decided to call myself a ‘designer’. I think I just wanted to make the business sound bigger than it was. And I thought it was cool.

I am not sure exactly how much this disaster cost us in total. A deposit on a house perhaps. After our employee’s year contract was up we labeled the project a failure and shut down.

The one bright side is that I didn’t work on it full-time. Although… maybe if I had it would have worked out… who knows. It’s in the past. And do I really want to be encouraging people to gamble? Nope.

Pioneer Projects

A website development firm.

A few years before the Bet-Central disaster, I studied computer science at university. Like most of my classmates, I thought I could make some easy money by starting a company that made websites. So I teamed up with a friend and we started a web development firm called Pioneer Projects.

Turns out I am rubbish at making websites. Web design and development requires a very different skill set than I was learning at university.

Thinking back now, I really cringe at some of the rubbish we made for our customers. It is probably the business I feel worst about.

For the developers out there here’s an example. We thought that flash sites looked cool so built a lot of solely flash websites. What that meant was that Google couldn’t read the content and they never appeared on Google. A waste of everyone’s time and money.

We weren’t even making the websites quickly. Because we didn’t know what we were doing we put in hundreds of hours worth of work and probably made a fraction of minimum wage.

After wasting a few months we packed it in.

Hanging Rock

A social media platform aimed at the Edinburgh Fringe Festival. We would make money through on-site ticket sales.

After the failure of Pioneer Projects, we should have just quit web development. But then we were approached by a comedy promoter who asked if we could design a social media website for the Edinborough Fringe Festival.

Like the naive 21-year-olds we were, we were sold the dream. We wouldn’t be paid, but in exchange we would own 35% of the company. They would do all the marketing and use their current promotional network to get all the big acts involved.

We bought loads of pizza and expensed it to the company. Living the dream.

They promised us the world. A £50k marketing budget from Microsoft (don’t ask me why Microsoft was involved…) and £30k from one of the directors. We would soon be millionaires.

Thinking we’d learnt from our mistakes in Pioneer Projects. We contacted the entrepreneur societies at a few universities and said we were looking for skilled programmers to work on the project in exchange for a share of the company.

We built a team and worked our arses off. The site was built, we launched it and then waited for customers and riches to roll in.

But no one came.

Eventually, it became clear that no marketing was being done. There was no £80k budget. No one came to the website. No sales were being made and then one day our main contact just stopped replying to emails.

Student Swag

An education company where we taught students how to matched bet by giving seminars and creating online resources.

This was a company I started with two friends. We had found a way to make money by taking advantage of the welcome bonuses bookies offer new customers and thought we could build a business around teaching other people to do it too.

We built a website, stuck posters all around the university promising easy money and ran a few seminars.

I’m actually still very good friends with some of the people who took the course and some of them have gone on to become successful entrepreneurs. I wonder if there is a link between the sort of person who’s willing to try out a random moneymaking idea they see on a poster and someone who’s willing to take a big risk and start a company…? Food for thought.

The business ran for about six months and we made around £10,000 after expenses. As there were three partners, £3,333 was nowhere near worth the huge amount of work we were putting into it.

When we announced we were closing down we got an offer of a buyout from a similar site, but it wasn’t for enough to make it worthwhile.

Grime Garms

An E-Commerce dropshipping store that sold clothing related to the UK music subculture grime.

I have a good friend who had a  popular blog where he wrote about the clothes that grime artists wore in their music videos.

Most of the brands in these videos are very small. Run by a couple of friends out of their bedroom and not stocked anywhere but on their own BigCartel website.

We had the idea of putting together a one-stop shop store for all these brands. When we received an order, we would forward it on along with the money minus our commission.

It all went initially went to plan. We created a website and started contacting all the different brands. Most were happy to work with us. We put up our favourites on the site and started selling.

That is when the problems started. We would get an order, forward it on and then hear nothing for a couple of weeks. The customer would chase us up and then we’d eventually get an email along the lines of:

orders late

I think even with that we probably could have made it work. We could have moved to stocking and fulfilling orders ourselves.

But an even bigger issue was that our margins were way too small. We thought dropshipping would be easy. Turns out it’s not.

We were taking a 10% commission but were doing all the order processing, customer service, generating the sales and taking all the stick from the customers when their clothes didn’t arrive.

For the pennies we were earning, it just wasn’t worth it. We did meet some interesting characters though.

I’ve just done some Googling and I don’t think any of the brands we were working with are still in business.

Importing Cars to Malta

A company that imported and sold used cars from the UK to Malta.

This business was the focus on my second ever blog post. It wasn’t a total failure, it made money and still had potential when we shut it down.

But it was high risk and took so long to get anywhere with it that we were faced with the choice of scaling up hard or quitting. We eventually closed the business down. It made a total of €6,388 after all costs and after roughly a year’s worth of work.

Here’s one of our vehicles. Still, the nicest car I’ve ever owned!

The main issue we had was the risk of holding constantly devaluing stock. The second car we bought took us over seven months to sell. After that, the thought was we either need to scale up a lot. Or quit.

We quit.

Weekly Bonuses

A Groupon-style website where we offered time-limited exclusive bonuses for bookies and casinos.

weekly bonuses

This was a collaboration with a friend. I convinced him to drop down to just working at his job two days a week and spending the other days trying to build a business with me and working on his blog.

The Groupon business didn’t work out. It took a lot of work to constantly be negotiating for new bonuses and we didn’t do much marketing so had very little traffic.

The project didn’t lose much money, maybe £1,000, but did take up a lot of time.

Luckily, it ended up working out for my friend. After Weekly Bonuses we started our table tennis brand and soon after he quit his job altogether.


A lot of these failures were down to rookie mistakes or being naive and falling for someone else’s dream. But without them, I wouldn’t have struck gold the few times I did.

So rather than pick random lessons I learnt and advise you to avoid my mistakes. I’m going to tell you the opposite.

Keep being naive and keep trying stuff you shouldn’t. It’s the only way to learn and when you finally hit gold it will have been well worth it. If I can do it, with all the ridiculous failures above, then anyone can.