The biggest mistake I made in business cost me north of $150k, plus an estimated $10m in opportunity cost.

I’ve seen many other entrepreneurs fall into the same trap.

Today I’m going to share that mistake with you, in the hope that you can avoid it.

Why listen to me?

The best lessons in life come via failure.

I have started more than 15 ‘businesses’ since the age of 18.

Only a couple of them made enough profit to pay myself an average salary, which is my bar for labelling a business successful.

Some of the others fizzled out, some were a spectacular flop.

I’ve made almost every mistake in the book, but there was only really one mistake that I regret.

The Mistake

In 2017 I started an agency.

We grew it to £500k ARR in 10 months. My first properly successful business.

I was on cloud nine.

However, the business was in the lead gen space, which wasn’t a sexy space to be in, and it seemed full of problems.

Meanwhile, I’d scroll Twitter and see scores of entrepreneurs brag about how fast their SaaS business was growing and how their margins were insane.

It seemed obvious. I had chosen the wrong industry and I needed to go start a SaaS business.

And there lies my first lesson.

The grass always seems greener from the other side.

Speak to a veteran of almost any industry, and they’ll tell you how hard their specific industry is, and how they wish they were in a different space.

But the truth is, almost every industry is hard. As soon as there is money to be made, entrepreneurs flood the market and it becomes hard to compete.

There are very few, if any, easy wins.

Anyway, back to the story..

I saw how Proof had just been accepted into YC and was growing like crazy. You know the little pop-ups at the bottom of a website that shows social proof - something like ‘27 people bought this in the past 24 hours’.

I thought, if I could just copy that product, I can use my cold email expertise to scale it rapidly.

I called it Credible.

Then I did what most non-technical founders do and I went to UpWork to find myself an agency.

I went with an impressive young English-speaking guy from Chicago who claimed to have a top team of experienced developers in India.

I paid him £15k and he promised me it’d be ready to launch in 3 months.

12 months later the product was nowhere near finished, we’d paid him all the money and they refused to keep working on the project because they had run out of funds.

I spent £15k, plus hundreds of my hours preparing the business for launch.

We didn’t make a single penny.

I Didn’t Learn The Right Lesson

I thought I had just hired the wrong dev agency.

And that it could have been avoided if I hadn’t paid them the full amount unless they delivered on time.

Either way, I was put off agencies and I decided that to do it right, I needed to hire someone in-house.

By this time, there were multiple Proof competitors and the market was flooded.

So I came up with a new idea.

I’d start an Airbnb-style marketplace where digital nomads (like me at the time) could find and book tables at free laptop-friendly cafes around the world.

I called it DeskHop.

I found myself a Serbian-based freelancer on UpWork who was an expert in Bubble, the no-code software builder.

He cost me $1,000 per month full-time.

Once again, it took 4x longer than we expected to launch.

Whilst the developer was a hard worker and a super nice guy, he wasn’t the best developer, and the platform wasn’t super polished.

But really the issue was that the product didn’t create enough value, so we couldn’t charge much for it, and acquiring customers in expensive, so it just didn’t add up.

We ran the platform for three years, spending around $60,000 and making about $60,0000, but we wasted thousands of hours of mine and my staff’s time on it.

Third Time Lucky?

12 months later, I had a brainwave.

I had just become obsessed with Bitclout, and I thought it was crazy there wasn’t a similar platform that allowed you to create Company Coins and use them to speculate on the future of private businesses.

So I found a world-class Bubble agency, paid them a bunch of money and we launched our own cryptocurrency.

I called it Backed.

We sold $2k of tokens in the first two weeks, then came a huge crypto crash and sales completely dried up.

I had spent another $60k+, plus hundreds of hours over 12 months building yet another product, and I’d failed again.

One Last Try

You might think that I had learned my lesson, but you’d be wrong.

The above quote is one of my favourites, but I can’t help but wonder whether in this instance it was a hindrance.

So I started again.

I contracted an agency to build CarbonBee, an app that allows almost any business to calculate their carbon footprint, then offset it by subscribing to our service where we plant trees for you each month.

I spent many months and tens of thousands of dollars, not to mention hundreds more hours trying to grow it.

We got 10-20 customers, but it was small stakes.

I suspected that one day we’d be able to sell to bigger companies, but it seemed like super slow progress and there were no guarantees it would pay off.

So I sold the business for $15k and cut my losses.

My Epiphany

After three years of spending $150k+ and wasting thousands of hours of my time, my newly hired business coach asked me what my goal was.

I told him it was to make $5m so I would have financial security and could live off the interest if I wanted to.

All four of the businesses I had just tried to start were potential unicorns.

But my goal wasn’t to be a billionaire, so why was I gambling on building businesses that had a very small chance of success?

If my goal is to earn $5m, the surest way to do it would be to build a boring business.

Then I realised that the agency I had been neglecting had continued to grow, despite me putting virtually zero effort into it.

So I put a plan together to double the agency from $1m - $2m ARR in 12 months.

12 months later we had achieved our goal, and the business was thriving.

But the lost opportunity cost was huge.

Over those three or so years, although it still worked, cold email had become much less effective.

So while we succeeded in doubling the business, I predict we could have 10x the business with the same effort and investment, if we had started three years earlier.

What Did I Learn?

If you want to sacrifice the best years of your life for a 1/10 chance of building a billion-dollar company, then go ahead.

We need some of you to change the world.

But be honest with yourself about what you really want. What is your end goal?

If you’re like me and you just want to make a few million dollars so you can live a good life, plus have freedom of time & location, then your highest odds of success will come from building a business that is proven to work.

The mistake I made was not setting my goal and working backwards to build a plan of how to get there.

I hope you can avoid making the same mistake.


Go get it!

Lee