If you are a founder, you usually see buyers at their most polished moment. A clean offer. A short bio and maybe a deck.

What you almost never see is the quieter side. The deals that stall. The ones buyers walk away from. The ones where you pick someone else. From my side, that is where a lot of the real learning sits.

Here a few of those from my own journey into acquiring e-commerce agency businesses.

One of the first serious opportunities I looked at was on paper very strong.

The numbers were solid. Recent years looked good. The team structure made sense. It matched a lot of what I thought I was looking for.

The more I dug in, the more one thing stood out. Almost all of the sales and key relationships lived in the founder’s head. The brand presence was mostly a personal account. New work came from the owner’s outbound efforts. Very little was written down about how clients were found, closed and retained.

If I pictured the business a year after a sale, the risk was clear. The owner steps away, the personal brand fades and new work slows. Not because the service is weak but because the sales engine was never really separate from the founder.

From your side as a founder, this is what that means: if everything important flows through you, a buyer has to rebuild the front of the business just as you leave. Some may still be up for that. Others like me in this case, will decide they are not the right fit and quietly walk away.

Another opportunity was very lean. Strong numbers, controlled cost base, no wasted headcount.

Then I asked a simple question: who is staying?

The owner wanted to leave. The main operations person wanted to leave. The finance person was also open to going. After more questions, it was clear the owner and ops lead carried most of the know how. Very little of it lived in systems or docs.

Could someone step in after both of them left and slowly figure it out. Possibly. However I would I have to rebuild the machine from scratch while learning the sector. So not quite right opportunity for me.

From a founder’s view, a wave of key people wanting out at the same time is a signal buyers have to respect. It does not mean the business is bad but it does change the kind of buyer who will feel comfortable stepping in.

One deal had no real issues on the business side. The problem was me.

It was one of my first proper calls with a business owner. He knew his numbers, his market and had already spoken with other buyers. This was familiar ground for him.

We had a good discussion about the company. Strong position in e-commerce sector, clear results after 2020.

Looking back, I spent most of the call trying to sound right instead of listening. He went straight to numbers  and I followed. We talked price and structure before I really understood what he wanted from his next chapter.

He chose a buyer with a roll up already in place. That made sense for him. They could plug him into a larger setup that was already up and running.

From the founder’s side, this was simply one more data point. Sometimes buyers will sound a bit clumsy, especially when they are new to the market. Part of your job as a seller is to read that and decide who feels right for you. In this case, I was not that person and I agree.

Another business I looked at was strong in most of the ways that matter.

The financials were healthy. The team was capable. They were early in using AI in their process and client delivery, which made sense for where the market is going.

As we spoke, it became clear we wanted different things from the future.

My plan is to buy and keep building, stay close to the business and its people and grow what is already there. Their ideal outcome was to maximise price and sell to a private equity buyer with a larger cheque and a different plan.

There is nothing wrong with that choice. Years of work give a founder the right to pick the path that fits their life.

In that sense, the seller’s clarity helped. They knew what “good” looked like for them, which made it easy to see I was not the right fit and to move on quickly.

The easy story about buying businesses is a straight line. See deal. Do deal. Move on.

The reality feels very different. Some deals do not happen because of clear operational or team risk. Some do not happen because the timing or goals do not line up.

From where I sit, those experiences are not failures. They are information and lessons. They shape how I now think about owner dependency, key staff, rapport and fit.

From a founder’s view, these near misses are a reminder that deals do not only fall through because something is wrong with the business or the buyer. Often it is just a mismatch of timing, risk, or direction.

If you run an e-commerce digital agency and this resonates, you are always welcome to reach out.

Passing can be progress,

Jordan