What teaching to a class of entrepreneurs taught me about business founders.

I recently taught branding and positioning to a class of around ten entrepreneurs here in Northern Italy.

I went in thinking this would be a one-way stream: I would teach them some of the things I have learned over years of working on branding, communication, and positioning. Instead, the classes I hosted taught me a lot too. I came out with a much better understanding of how entrepreneurs actually think, or maybe more precisely, how they are forced to think by the reality of running a small business every day.

In theory, when we talk about founders and business owners, we imagine people who are always looking ahead, imagining the future, developing the business, spotting opportunities, and building the next step before the current step becomes unstable.

That is the theory.

The reality, at least from what I saw, is much messier and much more human.

I witnessed how difficult it was for some of them to step out of the everyday life of their business, take a breath, and think about deeper questions like why they do what they do, where they want to go, what kind of business they want to build, and what objectives they should set for the future.

For some of them, even just listing some 10-years-objectives felt almost impossible.

And this is exactly where the gap became clear: the difference between how we imagine an entrepreneur should think in theory, and how they actually think in reality when they are inside the machine every day, dealing with clients, suppliers, employees, deadlines, bureaucracy, payments, uncertainty, and all the wonderful little gifts that come with running a business in Italy.

They are trapped inside a system that doesn’t give them enough space to act like the ideal version of an entrepreneur we read about in books.

Because when you are busy and frustrated with bureaucracy, with the noise that dominates every market, with customers who are more cautious, with costs that change suddenly, with geopolitical crises that sound like a far-fetched excuse for a small business owner in Northern Italy until they are not far-fetched at all, because suddenly the famous electricity bill goes up, budgets get eaten somewhere else, and people buy fewer machines, fewer services, fewer things that yesterday felt necessary and today feel like something they can maybe postpone.

So when someone like me walks into the room and says, “Let’s talk about your why,” I understand that for some people the first reaction might be to tune out, think “no, not another one of these people trying to sell me smoke,” and check their watch to see how long this out-of-touch marketing consultant is going to keep them away from the things they actually need to do.

And honestly, fair enough.

This is where I learned something important about teaching.

It is not enough to know that a concept you want to share is useful. You have to understand the emotional and practical distance between the concept and the person sitting in front of you.

Because if that distance is too big, they don’t reject the concept because they don’t care, or because they are not ambitious enough. They reject it because it sounds like it belongs to another world. And this is a problem I have probably contributed to myself many times, because I too have used the classic examples we all use when we talk about branding and positioning.

Apple. Nike. Patagonia. Tesla. Coca-Cola.

The usual suspects.

The marketing Avengers.

They are useful examples, because they show principles clearly and they are brands most people recognize, but when you are speaking to a small entrepreneur in Northern Italy, someone who maybe has a company with a couple of employees and does half of the business functions personally, these examples can feel completely disconnected from their reality. You mention Apple and you can almost hear the objection before they even say it.

“Yes, but that’s Apple.”

And they are right. Not completely right, but right enough that we should take the objection seriously.

Because what they are really saying is not “branding doesn’t matter.” What they are saying is:

“I do not have that budget, that team, that cultural power, that visibility, that ecosystem, or that luxury of time, so please explain to me what part of this actually applies to me.”

And this is where I think a big part of my job is, and where I want to focus even more in the future.

Translation.

Translation from big marketing ideas into something that makes sense for smaller realities, for local businesses, for companies that are excellent at what they do but struggle to explain why it matters, and especially for Italian companies that want to expand abroad.

This new two-day branding and positioning course I developed for CNA received a lot of interest, so much so that, due to demand, we are repeating it again in a couple of weeks. Of course I am happy about that, but honestly the part that fills me with the most joy is much smaller and much more human: hearing someone say, “Oh, I never thought about it this way.” Because that means that, even in a very small way, I helped someone stop for a moment, look at their business from a different angle, and maybe try something new that could improve their situation.