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Buying a Loss-Making Business: Why I Told a Friend to Look at the Bigger Picture First

Buying a Loss-Making Business: Why I Told a Friend to Look at the Bigger Picture First

October 22, 2026•4 min read

Buying a loss-making business looks like an opportunity when the price is low and the turnover is large. Yesterday one of my closest friends told me he had been offered exactly that. The company turns over close to 10 million and it loses money. It sits close to what he already does. He could pick it up cheaply, and he and his business partner believed a turnaround could change their lives.

He was keen. I could hear it in how he talked about it.

I did not tell him to say no. I asked him one question: is it worth it for what you are trying to build?

I know my friend well. I know why he built his business. He wants a lifestyle, and money is only part of that. He wants freedom, time and choice. His own business has grown steadily over the last 18 months or so. It is starting to work.

A loss-making business with that much turnover and that much overhead does not deliver freedom. It takes focus. It brings stress and anxiety. There is no guarantee a turnaround works. And the attention it needs would come straight out of the business that is finally doing well.

The conversation mattered because of what he had not weighed yet. He saw the opportunity and the potential. He had not looked at the effect on his daily life, his energy or the business he had already built. That is easy to do. When a deal looks cheap, the mind runs ahead to the upside.

I want to be clear about what I said and did not say. I am not telling you he will walk away. That is his decision. What I care about is that he now gives it the care a decision of that size needs. He goes in with his eyes open, not wearing rose-tinted glasses.

Today I ran day 2114 of my daily streak, and this topic stayed with me for the whole run. The streak has taught me something about decisions. Running every day for this long is made of small, repeated choices. Almost none of them are dramatic. But the few large choices, such as committing to the streak itself, were made against a long view. I did not ask whether one run was worth it. I asked what I was building across years.

That is the question I gave my friend. Does this opportunity fit what you ultimately want out of life?

If the answer is yes, the decision is easy. You proceed, and you still do the work to check the numbers and the risks. If the answer is no, you have a harder situation. The worst outcome is to go into something and find yourself trapped. A loss-making business of that size could do serious damage to your personal situation if the turnaround fails.

So here is the process I would suggest if you face a decision like this.

First, step back. Take a breather before you reply to anyone. A rushed yes is hard to undo.

Second, write down what you want from your life. Not what the deal could earn, but how you want your days to look. Time, freedom, health, family.

Third, set the opportunity against that list. Ask what it adds and what it removes. Be honest about the stress and the focus it will cost.

Fourth, ask who else it affects. A business partner, a family, a team, your existing business.

Fifth, decide only after that. If you still want it, you will go in clear-headed.

None of this is complicated. The difficulty is doing it when you are excited. Excitement narrows your view, and a good price makes it narrower still.

I also hold myself to this. I run a property portfolio and I run Operations Director. There are plenty of tempting opportunities in both. My rule is to optimise what I already have before I expand. That rule exists because I have felt the pull of a shiny deal. Looking at the bigger picture protects the things I have already built.

The same thinking sits behind the run. I am running a lap of the world, 40,075km, barefoot-style, one day at a time, and sharing it daily to raise £1M for children's causes. After today the total is 16,252.94km, which leaves 23,822.06km to go. That mission is long. It only works if I protect the time, health and focus it needs. Every large decision I make has to pass that test. Does it fit the mission, or does it get in its way?

I am not the finished article on this. I make rushed calls too. But a short conversation with a friend yesterday reminded me how much a single question can change the shape of a decision.

If you are facing something big right now, take a step back. Ask yourself what you want. Then decide.

If you want to follow the mission, watch the daily episodes, subscribe and share them. The more people the vlog reaches, the more we can raise for children's causes, and that is why I do this every single day.

Watch the full episode: https://youtu.be/TUPfVHpVsGo

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I am on a mission to raise £1,000,000 for children's causes by daily run-vlogging barefoot-style, covering the total distance of a lap around the world—40,075 km.

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