When I first started looking at buying a business, I made a very predictable mistake. I treated it like any other product problem.

In my head, it looked something like this: see an inefficient business, think of a technology and fix everything. That mindset works when you are deploying a feature or solving a business problem. It does not work when you are trying to buy a real company that already has history, people and customers.

I have spent more than a decade in tech, a lot of it inside e-commerce and direct to consumer brands. I am used to thinking in terms of systems, processes, performance, efficiency. So at first, I approached acquisitions the same way: look at the numbers, spot the bottleneck, imagine the technical solution.

The problem is that a business is not just a system you just technically optimise. When you buy one, you are not only buying assets or software. You are stepping into an ecosystem that already exists. There are customers with expectations, team members with their own habits, an owner with a specific way of doing things, processes tailored to the business identity and a set of unspoken agreements that never show up in a spreadsheet.

Most of the real challenges are not technical. They are operational, cultural, or relational. For example, a founder who carries everything in their head, a team that is loyal to the owner, not the company or clients who stay because of one person, not the brand. None of that can be fixed with a few line of code and a new dashboard.

Another common trap is to treat the whole thing like a pure numbers game. It is very tempting to open a spreadsheet, pull a few ratios and feel like you understand the business.

Revenue, margin, churn, client concentration. All of that matters  and I pay attention to it. But the numbers are only a snapshot. They do not tell you why the founder is really thinking about selling, what keeps the team motivated or drained, or which clients are stable and which ones are one difficult conversation away from leaving.

Those answers come from conversations, not from a profit and loss statement. The more time I spend talking with owners, the more I realise that buying a business is a person to person decision first and a financial decision second.

One thing that helps a lot and that I do not see talked about enough, is having a clear focus before you start looking at deals.

In my case, I am not trying to look at every profitable business that appears on a listing site. I have more than a decade in tech - with a lot of that time overlapping e-commerce and direct to consumer work- so it makes sense for me to stay close to that world.

Right now, that means looking at businesses that serve e-commerce world rather than only the brands themselves. For example:

That focus helps in two ways. First, I actually understand the work. I know what good looks like and where the common problems are. Second, I can see where my skills might add value without pretending that technology alone will magically fix everything.

Going in without any sector or model in mind usually means a lot of noise and not much progress.

Another thing that is easy to underestimate is the emotional and time load that comes with finding the right opportunity.

From the outside, it is simple to say, “I will look at a few deals and pick one if the numbers make sense.” In practice, you review a lot of businesses that are not a fit, you start conversations that go nowhere or that you think might soon close… then it falls apart.

It takes patience and grit. There are long stretches where you are just collecting information, building relationships, and saying no.

This is where keeping things simple matters. It is tempting to build complex deal tracking tools and over automate the process. In reality, you need a clear filter, a way to take notes, and the willingness to keep showing up. Straightforward conversations and time.

In the next issue, I will talk about why some founders say they are open to selling, but hesitate when it starts to feel real. Understanding that hesitation is important if you want any conversation to move into partnership.

If you run a digital agency or an e-commerce brand and are thinking about what comes next, I’d love to hear from you.

Thanks for reading,

Jordan