In August 2020 I wrote five lines addressed to hiring managers, asking them to stop demanding five or more years of experience for entry level jobs.
It did 22,742 likes. 1,676 comments. 868 shares.
It is still the best-performing thing I have ever published, and nothing since has come close. It was also read almost entirely by people who could never hire me.
That post is one of three times I aimed my business at the wrong buyer. The other two cost me more, and they were harder to see coming.
The audience that could not buy anything
I kept going for a long time after that post, because it worked. Open letters about unrealistic job requirements. Posts about graduates sending forty applications and getting two interviews. Every one of them traveled further than anything I wrote about sales.
None of them built the business I have now. I spent a large part of two years being read by people who liked what I wrote and had no reason to buy anything from me, and then had to start again in front of an audience of B2B founders.
The lesson is not "post about your niche", which is advice anyone can give you. It is narrower. Reach is the easiest number on the page to move, and it is the one with the weakest connection to revenue. A post that gets 22,000 reactions from the wrong room is worth less than a post that gets 40 reactions from twelve buyers and two of their competitors.
If you are choosing between writing something that will travel and writing something your buyer will recognize, choose the buyer. I have written elsewhere about what founder content is actually for, and it is not applause.
The clients I could learn nothing from
At the same time, I was running free online events for dental clinics, aesthetics clinics, plastic surgeons, medical spas and chiropractors. How to get new patients every day from social media and search engines. How to stop relying on referrals. A hundred seats, owners from the US, the UK, Canada, Australia and New Zealand.
It was real work for real businesses, and I was decent at it.
Here is what I did not understand at the time. A clinic owner filling appointment slots in one city and a software company chasing a six-figure contract across two continents have almost nothing in common, and neither do the skills you need to help them. The tactics were local, the money was small and fast, and the decision took an afternoon. When I moved to B2B, most of what I had learned was worth nothing. I kept the work ethic and lost the playbook.
That is the cost nobody puts a number on. Not the revenue you earn from the wrong clients, which is usually fine. The years of learning that do not stack on top of each other.
So the question I would ask before taking on a type of client is not only whether they will pay. It is whether the tenth one teaches you something the first one did not.
The second business hiding inside the first
In 2023 I did something that felt obvious at the time. There was real demand for people who could book B2B meetings properly, I had the process written down, so I started training people to become client acquisition specialists.
Two mistakes in one, as it turned out.
The first was that the result I was selling lived inside other people's decisions. Whether someone did the work. Whether a company hired them at the end of it. I could control the teaching and almost nothing after it, which is a bad position to sell from and an uncomfortable one to sit in when it goes wrong.
The second is subtler and more expensive. It was a different business from the one I was already in. Running campaigns for B2B companies and running a training operation share maybe a tenth of their work. Different product, different buyer, different support load, different way of losing your evenings. It pulled attention out of the thing that was working, to build something adjacent that I did not really want to own.
Founders do this constantly. The new thing is next door to the old thing, it uses what you already know, the demand looks obvious, and it quietly costs you the focus that made the first thing good. If you have ever been argued out of adding a second service line, you know the shape of it already: one offer, one audience.
I do not run that program anymore.
What the three have in common
None of them were bad ideas. Each one was easy to say yes to, and that was both the appeal and the flaw.
The letters to hiring managers were easy because the reach was enormous. The clinics were easy because they paid and the work was familiar. The training program was easy because the demand was visible and the skill was already in my head.
Not one of them was built backwards from the question I use now: who do I want to be working with in three years, and does this bring me more of them or fewer?
That question kills a lot of good-looking ideas. It has also made the business much simpler. One thing, sold to one kind of company, delivered by a team that does it every day.
If you are designing something new this quarter, run it through that filter before you run it through a spreadsheet. Not "will this sell", which is the easy question. Ask who it will bring you, and whether you want them. If you want the arithmetic version of the same decision, it is in how I pick a market.