I Tried to Give a Contractor Five Thousand Dollars Last Month. He Never Found Out.

On a Saturday morning, a man I have hired before sent someone to look at two loose boards on my deck steps, and I tried to hand that person about five thousand dollars.

Curtis runs a small exterior painting and carpentry outfit, and he is good — careful, tidy, turns up when he says he will, which puts him in a minority I have come to appreciate. He was booked that morning, so he sent his foreman to look at the steps.

The foreman looked at the steps. And while he was standing on the deck, I did what customers do, which is point at the thing underneath him.

The deck needs stripping, the boards want fixing, and the whole thing needs refinishing before another winter gets into it. It is a real job. It is somewhere around five thousand dollars of work and I wanted it done inside the month.

He listened. He looked where I was pointing. He wrote nothing down. Then he said the sentence.

“You’d have to ask Curtis.”

I asked roughly what that sort of thing runs. You’d have to ask Curtis. I asked whether it could be done before the weather turned. You’d have to ask Curtis.

Three questions, one answer. And Curtis, as far as I know, has still never heard about any of it.

The tell

Here is the part I want to sit on, because it is the whole note.

Curtis did not lose that job. Nothing happened to Curtis. There was no bad review, no lost bid, no competitor who came in cheaper. A customer who likes him stood on his own patch of ground with money out and a deadline attached, and his business had no mechanism for taking it.

He will never see this. It will not appear in his accounts, because it never became a number. It will not appear in his pipeline, because it never became a lead. It will not appear in his receivables, because nobody ever raised an invoice for a job nobody ever quoted. The only place that five thousand dollars exists is in my head and now in yours.

Nobody calls to tell you they tried to give you money and gave up. That is not a thing customers do. We just quietly go and ask somebody else, and you carry on believing you had a normal month.

I have since worked out that I was, at the time, the third-most-expensive job on his list and the only one nobody had told him about.

What I got wrong

For about a week I assumed it would get passed along. That is what I would have done, so I assumed it was what would happen: he goes back to the yard, mentions that the woman on the corner is after a deck, Curtis calls me Tuesday.

There was no mechanism by which that could happen.

There is no job sheet with a line on it for what else did the customer ask about. Nobody at the end of the day asks the question. There is no form, no note, no five-minute conversation where it would come up. So a sentence like she wants the whole deck done has nowhere to go.

So my assumption wasn’t optimistic. It was just wrong about how the business is built. A thing gets passed along when there is something to pass it along through, and there wasn’t. The message didn’t get lost — it was never a message.

The three reasons a busy business runs out of money

Almost every owner I meet who is short of cash describes it the same way. I sold. Where’s the money? It is one sentence, and it covers three completely different diseases, and the reason so many owners stay stuck is that they treat their own version as the one they’ve read the most about.

One: you’re not collecting. The work is done, the invoice is out, and the money is sitting in somebody else’s account. Terms drift, nobody chases, and the owner is quietly embarrassed to ask a good customer for what a good customer already owes. The fix is unglamorous and it is entirely about cadence: bill on a schedule instead of when you remember, take money before the engagement starts rather than after it ends, and have somebody whose actual job it is to ask.

Two: you’re not charging enough. Plenty of work, paid on time, and the margin isn’t there — usually because the prices were set for a smaller, simpler version of the business and never revisited. That was last week’s note, and the fix is math you can do in an afternoon.

Three: the work arrives in clumps. You’re collecting fine and charging fine, and the money still comes in lumps with troughs between them, so payroll is an event and two slow weeks feel like the beginning of the end. This one is a selling problem wearing a cash problem’s coat.

Here is the part I want to be careful about, because it is where a lot of confident advice does real damage. “Sell more” is the right answer to the third disease and an actively harmful answer to the first. If your problem is that customers pay late, selling more work means delivering more before you’re paid — more wages out, more materials out, more of your money financing somebody else’s business. You will feel busier and be poorer. I have watched it happen to people who were doing exactly what they’d been told.

So do the boring diagnostic before you do anything: take last year and ask which of the three you actually have. Most owners have two, and only one of them is the constraint.

Curtis has the third one. And the reason his months are lumpy isn’t that demand is lumpy. Demand was standing in his own foreman’s line of sight on a Saturday morning.

Why selling is always the thing that falls off

Curtis is not lazy and he is not disorganized. He is doing the work. That is the entire problem, and it is a completely acceptable thing to be doing.

Doing the work has a deadline. A customer is standing there, a job is half-finished, rain is coming Thursday. Selling the work has no deadline at all. Nobody is waiting in a driveway for Curtis to write down what he charges to refinish a deck. So on any given day the work wins, and it wins for the best reason available: it is the obvious thing that people are waiting for.

Except that I was waiting too. I was waiting for a bid. He had no way of knowing that, which is exactly the point — the customers waiting on you are invisible, and the ones standing in front of you are not.

Then the math gets cruel. The month is lumpy, so the money is lumpy, so the owner starts reading a selling problem as a cash problem — and goes and looks at his overheads, his suppliers, his rates, or a loan. Every one of those is a real thing you can look at. None of them is the reason.

Large companies have a name for the specific thing that happened on my deck. They call it speed to lead: how long it takes to get back to someone who has raised their hand, and how fast your odds drop for every hour you don’t. Enterprise sales teams buy software to shorten it, because they worked out some time ago that somebody asking is worth almost nothing and somebody answering is worth everything.

Nobody has ever sold that idea to a man with a ladder on his van, which is a shame, because his version is worse. A sales team that is slow loses a percentage of something it can count. Curtis doesn’t have a lead to be slow about. Nothing was ever written down, so there is nothing going cold in a queue — it evaporated on a Saturday while a good man stood on it.

I know this from the inside and not from a book. I once built a company from nothing to seven figures in nineteen months on pure outreach, talking to the single hardest audience I could have picked — so I am not in any doubt about whether selling works. But I know the pull of the other thing perfectly well. There is always something on a Tuesday afternoon that can be built or tidied or finished, and it will feel like a productive day, and it will be one.

The reason I now put the selling in the calendar before anything else gets to claim the time is that I learned, expensively, that it does not survive being left until later. Not because anyone lacks discipline. Because the building has a finish line and the selling doesn’t, and a day will always fill itself with whatever has an edge on it.

The clock is what makes it final

There is one more piece, and without it this is only a story about mild annoyance.

A deck has to be dry to be refinished, and it has to be done before the weather closes in. That is not a preference, it is a season. Which means my patience was never open-ended: there was a date after which the job stops being possible this year, and the window got smaller every week I didn’t hear from him.

That is what converts friction into lost revenue. Left alone, I wait. Given a deadline, I don’t — and the decision makes itself without anybody deciding anything. I didn’t fire him. I didn’t have a conversation with him. I like working with him and I still do. I just ran out of month.

Almost every business has one of these clocks and most owners never think of it as theirs: the season, the school year, the quarter, the moment the customer’s own project starts, the day the other quote lands. Your customer is on a timer you can’t see, and it is running while you are up a ladder.

What it isn’t, and what it costs to fix

It isn’t that Curtis needs more crew. He has crew. The crew was standing on the deck.

It isn’t that he needs more marketing. He has more demand than he is capturing already, which is the good problem, and it stays a good problem for exactly as long as it takes a customer to find somebody else. Paying to get more people asking, when the ones already asking are evaporating on somebody’s deck, is a way of paying to lose slightly more.

Something that answers is a different matter, and worth separating out, because it usually gets lumped in with marketing and it isn’t marketing. A page that lists what you charge for the common jobs, or something on your website that will talk to a customer at nine at night and take down what they want — those aren’t there to find you work. They’re there to catch the work that already found you, on the evening you were on a roof. That is the same job as the sentence you give your foreman, done by other means.

And it isn’t a character flaw, so it doesn’t get fixed with more discipline. Every year somebody tells a hardworking owner to be better at business development, and every year the work is still standing in the driveway at 7am, and the work wins, because the work should win. You do not fix a structural problem by asking someone to be a better person about it.

What it actually takes is smaller and duller than that, which is the good news and the reason almost nobody does it:

Write down a price for the six things you get asked about most. Not a full rate card. Six. A range is fine, and a range is usually more honest than a number — a price per square foot with a spread in it for the condition of the boards is infinitely more useful to a customer standing on one than silence is.

Then give anyone who goes out to a customer’s property one sentence to say and one thing to do. The sentence is a range and a promise: that’s the sort of thing we do, it usually runs about this, I’ll have Curtis call you today. The thing to do is write it on the job sheet before leaving. That’s it. That is the entire mechanism the business was missing, and it costs an afternoon and a piece of paper.

Then the call actually has to happen, because it has now become a promise somebody else made on your behalf — which is usually the only kind of promise that reliably gets kept.

Going looking for this is genuinely unpleasant, and it stays unpleasant right up until you find the first one, at which point it turns into math and you can do something about it.

The number under the number

Last week I wrote about a woman whose prices lived in her head, and what that cost her was margin — she did the work and got paid too little for it.

This is the same thing one floor down. When the price lives in your head, sometimes you get paid too little for the work. And sometimes the work never arrives at all, so you don’t get the chance to be underpaid for it, and that version doesn’t show up anywhere. Margin you can find later, in a spreadsheet, on a bad evening. Revenue that was offered and never collected is invisible for the rest of the life of the business.

Which is a strange kind of comfort, if you turn it over. Everything on your accounts is at least something that happened. The dangerous number is the one that isn’t on there.

Next Tuesday: another one of these — the next thing that’s true and nobody says.

Common Questions

Why is my cash flow so uneven when the business is busy?

Busy and profitable aren’t the same as predictable. Uneven cash flow in a healthy business usually comes from one of three causes, and they need opposite responses. You may not be collecting — the work is done and invoiced, but terms have drifted and nobody chases. You may not be charging enough, typically because prices were set for a smaller version of the business. Or the work itself arrives in clumps, because selling happens only when delivery allows it. The third is a selling problem presenting as a cash problem, and it’s the one most often misread.

Will selling more fix my cash flow?

Only if the problem is that work arrives unevenly. If the problem is that customers pay late, selling more makes it worse — you deliver more work before being paid, so more of your own money goes out in wages and materials, financing your customers. You feel busier and hold less cash. Diagnose which of the three causes you actually have before increasing volume; most businesses have two, and only one is the constraint.

How do I make cash flow more predictable?

Predictability comes from steady demand capture and steady collection, not from cutting costs. On collection: bill on a fixed schedule rather than when you remember, take payment before an engagement begins where the work allows it, and make chasing someone’s defined job. On demand: make sure a customer can get an answer when you personally aren’t there — a written price or range for your most common jobs, and one sentence anyone visiting a customer can say. Cost-cutting improves a bad month; capture and cadence change every month.

What is the revenue you never knew you lost?

It’s work a customer was ready to buy that never became a quote, an invoice or a lead — so it appears nowhere in the accounts. It typically happens when the only person who can price a job isn’t the person in front of the customer, and there’s no way for the request to get passed on. It’s uniquely hard to manage because it leaves no trace: customers rarely tell a business they tried to buy and gave up, they just call somebody else. The only defence is a written price for common work and a captured note from every customer visit.

Is this the same thing as speed to lead?

It’s the small-business version, and it’s worse. Speed to lead is the sales term for how fast a business gets back to someone who asked, and the well-known finding is that the odds of winning drop fast within the first hour. That framing assumes somebody wrote the request down — that it exists as a lead going cold in a queue. In an owner-run business it often isn’t written down at all, because the person the customer spoke to had no way to price it and no route to pass it on. There is nothing to be slow about. The tooling sold to fix speed to lead — routing, alerts, automated follow-up — all starts from a captured lead, so none of it applies. The fix here is earlier and cheaper: a written price for common jobs, and one sentence for whoever is on site.

The Saturday morning happened. Curtis is a composite — the trade, the location and the details are changed to protect a real supplier I still work with. Figures are illustrative. Education only — not financial, tax, or legal advice.