Since I started talking with founders about possible acquisitions, I have noticed a pattern.

A founder will say something like, “I am open to selling” or “I would consider an offer.” On the surface, it sounds clear but once you get into real conversations, you feel a lot of hesitation underneath.

Most of the time, that hesitation is not random. It usually sits in three places: what is happening in their head, what is happening in their heart, and what the process looks like to them.

A lot of founders start by being curious. They want to know what their business might be worth. They hear stories, potential multiples, or see someone they know exit, and they think, “I should at least find out.” Then reality shows up..

Maybe the financials are not as clean as they would like it to be. The business might depends heavily on them personally or maybe the profit is solid but the structure looks more like a demanding job than a self sustaining company.

On top of that, the idea of the deal itself is often different from what they expect. Many imagine a single large number paid up front. In practice, there might be a mix of up front payment, deferred payments, and risk sharing. Once they realise it is not just a big cheque and a clean break, their head starts raising questions.

None of this means they are wrong. It just means they now see the trade offs more clearly, and that can slow everything down.

For a lot of owners, the business is not just an asset. It is a big part of who they are. They built it over years, often through stress, risk, and a lot of personal sacrifice. Stepping away is not just a financial decision. It is an identity shift. They think about their team,  their clients, and their reputation. Questions show up, even if they do not always say them out loud:

Will the new owner look after my team, or replace them?

Will clients be treated with the same care, or just seen as contracts?

Will the values of the business survive, or does everything reset once the deal is signed?

If those questions stay unanswered, the heart will quietly resist, even if the numbers look fine. This is where trust matters more than any model. If a founder does not feel that you understand what their work means to them, it is very hard for them to move forward; hence the importance of building rapport matters more than the transaction itself quite often.

From the outside, selling a business can sound simple. Put a number on it, find a buyer, sign papers, and move on. In reality, it is a long and sometimes uncomfortable process.

There is due diligence, where someone you just met looks into the details of how you run things. There are questions about margin, clients, staff, systems. It can feel like your work is being pulled apart and inspected. That alone can make a founder step back. Then comes the question of what happens after the sale.

Some founders have a clear plan. They know what they want to do next, whether it is another project, a different role, or more time for life outside work. Others do not, for them, selling does not just mean leaving a business. It means waking up without the structure that has shaped their days for years. If there is no clear picture of what comes next, it is very easy for a founder to slow things down or quietly disappear from the conversation.

From what I have seen so far, a few things stand out:

- When a founder says they are open to selling, it often means “I am curious, but I am not sure yet.”

- Valuation, deal structure, and owner dependency can create a big gap between the idea of selling and the reality of a deal.

- Emotional questions about team, clients, and legacy matter just as much as the financial ones.

- The process is tiring, and the lack of a clear plan after the sale can keep a founder stuck between yes and no.

If you run an e commerce brand or a digital agency and have started to think about what your next chapter might look like, I am always open to a conversation. Even if you are not planning to sell now, hearing how it feels from your side always help to understand you more.

Thanks for reading,

Jordan