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Too Late, My Ass

How to Get Your First Customer (and Why Your Mother Does Not Count)

first customer how to get your first customer make money after 50 starting a business after 50 Nov 05, 2026
Fay Chapple smiling across a cafe table at a woman, beside the title The woman who sent me my first client

Your first real customer is someone who buys without already loving you. Sales from family and close friends feel like proof, but they tell you almost nothing about whether the thing works. The people most likely to find you a stranger who buys are the ones at the edge of your life: old colleagues, people you have not spoken to in a year. Send each of them one plain sentence saying what you make, who it is for, and asking if they know one person like that.

Here is how I found that out, and why it took me twenty five years to notice.

What's covered:

  • Why your first sales from friends and family do not count
  • Where useful introductions actually come from
  • Why "please share this" gets you nothing
  • The one sentence to send instead

The woman who sent me my first client

I have been trying all week to remember who sent me my first paying client, and the answer, when it finally surfaced on Tuesday night, annoyed me enormously.

It was a woman called Dawn who worked in the accounts department of a company I had left eight months earlier. We were not friends. We were the kind of colleagues who are perfectly pleasant in a lift. I knew she had two daughters and a strong opinion about the kettle. She knew I had gone off to do something on my own and had probably assumed, correctly, that it was going badly.

And one afternoon she rang me, which was already strange, and said that her husband's cousin had a shop that was being rebranded by somebody who had made it worse, and did I do that sort of thing.

That was the first real money. Not from the three people I had told about the business constantly for eight months. Not from my best friend, who was extremely supportive and sent me approximately forty encouraging messages and zero clients. From Dawn, in accounts, with the kettle opinion.

I had forgotten her completely. I want to be honest about that, because it is the ugly bit. For twenty five years I have told the story of starting out as though it began with my own cleverness, and the actual beginning was a woman I had not thought about since 2003 making one phone call she did not have to make.

Three sales, and every buyer had my phone number

I am thinking about Dawn this week because on Saturday morning I sat on a live and read out five weeks of numbers for eleven things we have built from nothing on camera, and for the first time there were sales. Three of them. My sister, a woman I worked with in 2009, and a man at the gym who was being kind.

All three of them already had my phone number.

And what I noticed in myself, in the hour afterwards, was relief. The relief of not having to do the frightening part yet. Somebody had bought something, so the thing was presumably fine, so the terrifying job of walking up to a stranger could reasonably wait until next week. I have watched that same relief settle on a lot of people over 50 who were starting something, and I have watched it sit there for two years while nothing moves.

Why the warm sales are a cushion and not a beginning

Because the warm sales are not a beginning. They are a cushion. And a cushion is a thing you sit on.

Here is what I think is actually going on, and it is not a confidence problem, although it dresses up as one.

When you tell somebody who loves you about the thing you are building, you are not selling. You are confiding. The two feel almost identical from the inside and they are completely different transactions. Confiding is lovely. You get warmth back, and encouragement, and sometimes money, and all of it goes into the same part of you that needed reassurance in the first place. Nothing is risked, so nothing is learned.

Selling means handing somebody a thing and letting them look at it without looking at you. It is the looking away that is unbearable. You have spent weeks on this and they are going to glance at it for four seconds and decide, and their decision will be about the thing, not about you, and that is exactly what you wanted and exactly what you cannot stand.

So we stay in the middle of our own lives, where everybody has already decided about us, and we call that building an audience.

Where the useful news actually comes from

There is a piece of research that explains why that is such an expensive place to stand. Mark Granovetter went and asked a few hundred people in Massachusetts how they had really got their job. Of the ones who got it through another person, fewer than one in five had heard about it from somebody they saw often. Just over half heard it from somebody they saw occasionally. More than a quarter from somebody they rarely saw at all.

The news came in from the edge.

And once you have read that, the Dawn story stops being a charming coincidence and starts being the normal shape of how things happen. Of course it was Dawn. My best friend and I know all the same people. We have the same contacts, the same gossip, the same view of the same wall. There was nothing in her network that was not already in mine.

Dawn's network was a completely different country. Her husband's cousin's shop was not a thing I could have reached from where I was standing, in any number of years, with any amount of effort. She was the only door.

Which means the people you have let go quiet are not a failure of friendship. They are the only infrastructure you have.

The eighty one people you have walked past

I went looking for mine on Monday night. The criterion was simple and slightly brutal. Have not spoken in over a year. Do not dislike. That is it. I went through contacts and old email and one terrible spreadsheet from 2019, and I got to eighty one people in about forty minutes, and I sat there feeling genuinely peculiar about it, because I would have sworn before I started that I knew fifteen people.

Eighty one. Eighty one doors I have been walking past because the handle is awkward.

Stop asking people to share it

Then I did the thing wrong, which I may as well tell you about since the whole point of doing this on camera is that you get the failures too.

I sent twenty four messages last week asking people to share something. Here is the link, would you share it if you get a minute, no pressure. Nearly everybody replied. Several of them were lovely about it. A few said they would definitely share it.

Nothing happened. Not one thing I could point at.

It took me two days to work out why, and when I did I was embarrassed, because it is obvious. Share it is a request with no instructions in it. I was asking people to do the hardest part of my job for me, for free, in their own words, without having been told who it is for. Most people cannot do that. The ones who try get it wrong. The rest press a button, feel they have helped, and move on, and the whole thing dies quietly without anybody having been unkind.

On Thursday I rewrote four of them. One line each. I make large print puzzle books for people whose eyes have had enough. It is for anybody who has given up on a crossword because the print is too small. Do you know one person like that.

Two came back with a name.

Two names, from four messages, in about four minutes, after two days of warm nothing. And the difference between the two versions is not charm or confidence or copywriting. It is that the second one asks a question a person can answer about their own life, and the first one asks them to go away and do some unpaid work on mine.

The sentence that has three parts and no apology

I keep thinking about what that means about Dawn, actually. Nobody asked Dawn anything. She just happened to know, because I had mentioned it once in a lift, what I did and who it was for. One sentence, eight months earlier, apparently in passing, and she carried it around until it matched something.

That is all this is. You put the sentence into enough hands at the edge of your life, plainly, with no apology in it, and then you wait for one of them to meet somebody.

So this week there is no building. We have built plenty. I am going through eighty one names with a sentence that has three parts and no apology in it, and I am going to feel ridiculous doing it, and somewhere in there is somebody's cousin with a shop.

And I am going to find Dawn on LinkedIn, because it occurs to me, twenty five years late, that I never thanked her properly.

Tell a stranger.

This week on Too Late, My Ass: Season 3, Episode 8, Your Mother Does Not Count. It covers what actually counts as a first customer, why the edge of your list is worth more than the middle, and the one sentence to send instead of asking people to share. Listen to the full episode.

Frequently asked questions

What counts as your first real customer?

Somebody who buys without already caring about you. A sale from your sister or a close friend is lovely, but they are buying you, not the thing. The first stranger who pays is the first real test.

Should I sell to friends and family first?

You can, and it is fine to accept their support. Just do not treat those sales as proof the product works, and do not let them become a reason to put off approaching people who do not know you.

How do I find my first customer with no audience?

Go through your contacts, old email and past colleagues for people you have not spoken to in over a year and do not dislike. Most people find far more than they expect. Send each one a single plain sentence about what you make and who it is for.

What should I say instead of asking people to share my post?

Say what it is, who it is for, and ask if they know one person like that. A question someone can answer about their own life gets replies. A request to share gets polite silence.

Is it harder to get customers when you start a business after 50?

No. You usually have more contacts than a younger founder, spread across decades of jobs, neighbourhoods and clubs. The hard part is reaching out to the ones you have let go quiet, not having too few.


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Read next: Is it too late to change careers at 50?, How to start consulting after retirement and How to make money after 50: six places to start

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