Vol 1 · Issue 93 · Monday, August 17, 2026

I had a call in the spring with a guy who runs a commercial cleaning company outside Tampa. Good operator. Forty one accounts, eleven people on payroll, and he'd just wrapped the best quarter he's ever had.

He also couldn't make payroll that Friday.

Nothing was broken. The work got done. The clients were happy. It's just that sixty three thousand dollars he had already earned was sitting in other people's bank accounts, and he was too polite to go get it.

That's the whole article. You can leave now if you want.

But if you've ever looked at a healthy revenue number on a Tuesday and then looked at your actual checking account and felt your stomach drop, stick around. This one is fixable in about a week, it costs you nothing, and it'll do more for your business this month than any new lead you could possibly go chase.

Here's how it happens to almost everybody.

You start out hungry. Somebody says yes, and you're so relieved they said yes that you don't want to spook them. So you do the work first and send the invoice after. You put net 30 on it because that's what invoices say. They pay on day 45 and you tell yourself that's just how it goes.

Do that a hundred times and congratulations, you're a lender. You front the labor, you front the materials, you carry all the risk, and you collect somewhere between thirty and sixty days later at zero percent interest. Actual banks charge good money for that service. You do it for free, then lie awake wondering why the business feels tight when the numbers look fine.

I've written before that revenue is a vanity number because of what's left after costs. This is the other half of it. It isn't only how much you keep. It's when it actually lands. A company with beautiful margins and terrible collection timing still goes under. Cash flow isn't a finance concept you'll get to someday. It's oxygen.

The good news is that nearly all of this is self inflicted. Which means you get to un inflict it, starting this week, without asking permission from anybody.

Ask for money before you start. Not all of it necessarily. But some of it, every time, no exceptions.

Fifty percent up front on projects. First month plus a setup fee on retainers. A deposit on anything custom. Pick your version, then make it the default line on every agreement that leaves your desk.

I already know the objection because I've heard it a thousand times. “My clients won't go for that.”

Your clients pay a deposit to the caterer. They put a retainer with their attorney. They buy the plane ticket months before they get on the plane. They prepay their insurance every six months without blinking. Nobody in the entire history of commerce has refused to hire a roofer because he wanted money up front. What you're actually worried about is that asking makes you look like you need it.

Flip that around. Asking for a deposit makes you look like you've done this before. Amateurs take whatever they can get and hope. Professionals have terms.

And a deposit does something no contract can do. It buys you a client who is emotionally committed. People who have paid you show up to the kickoff call with their homework done. People who haven't paid you reschedule twice and then go quiet. The deposit isn't just cash. It's a filter.

Here's the entire change, one line on your proposal:

Fifty percent due on signature. Balance due on completion.

That's it. If you close four proposals a month at eight grand each, you just pulled sixteen thousand dollars forward into this month instead of next. You didn't sell anything new. You didn't work more hours. You just stopped financing your customers for free.

Now, somebody will push back. Maybe one in fifteen. Here's what you say, and the trick is to say it like it's the most ordinary sentence in the world, because it is:

“The deposit covers materials and locks your spot on the schedule. It's how every job runs here.”

Then stop talking. Don't explain it twice. Don't offer an alternative before they've asked for one. The number of owners who talk themselves out of their own terms inside eleven seconds of silence is genuinely remarkable, and I've been that owner.

If they truly can't do fifty, take thirty. If they can't do thirty, take a thousand dollars flat. The exact percentage matters far less than the principle, which is that money moves before work does. Once that's true, everything downstream gets easier.

Go pull up your last invoice. I'll wait.

If it says net 30, answer this honestly. Who decided thirty days? Was it you? Did you negotiate it with anybody? Or did it come preloaded in the invoicing software four years ago and you've never touched it since?

Net 30 is a leftover from a world where invoices moved by mail and got paid by check. Your client can pay you from their phone in eleven seconds while they're in line at Starbucks. There's no operational reason for thirty days anymore. There's only habit, and it's your habit, not theirs.

Change it to due on receipt. If you sell to bigger companies with real accounts payable departments, go net 15 and have the conversation there. But stop volunteering for a month of float that nobody asked you for.

Then add the part everybody skips. A late fee that exists.

Not a threat. A term. Something boring, like this:

Invoices unpaid after 15 days accrue a 1.5 percent monthly service charge.

It goes on the invoice. It goes in the agreement. It sits there looking unremarkable, and it quietly changes behavior. Not because 1.5 percent hurts anybody. Because it tells the person on the other end that you keep track. Payables queues get sorted by who keeps track. That's not cynicism, that's just how the job works over there.

You'll almost never have to charge it. That was never the point. The point is what having it does to the conversation before you get anywhere near needing it.

The single biggest upgrade most owners can make this year is getting a card or an ACH authorization on file and charging it automatically.

Recurring clients should never get an invoice that asks them to do something. They should get a receipt. Those are two completely different emotional experiences. An invoice requests a decision. A receipt reports a fact. One of those can get postponed. The other can't.

If you're running on Go High Level or anything like it, this is already sitting in your account waiting for you to switch it on. Card on file, recurring charge, automatic receipt, done. Same story if you're direct on Stripe or QuickBooks. It's one Tuesday afternoon of setup for a permanent change in how money reaches you.

For project work, put the milestone charges on the same card that took the deposit, and say so in plain language in the agreement. “Card on file will be charged upon completion of each phase.” You just deleted your entire collections process before it had a chance to start.

Offer ACH too. Not because anybody loves ACH, but because card fees on a twelve thousand dollar invoice are real money, and giving people a cheaper lane they'll actually use is worth the two minutes.

And if you run anything longer than about six weeks, stop billing at the end. Bill on progress.

Thirds work fine for most people. A third to start, a third at the halfway mark, a third at delivery. On bigger builds go to quarters. The rule is that your outstanding exposure at any given moment should never be more than you'd be willing to eat if the client vanished tomorrow, and you should actually do that math instead of vaguely feeling okay about it.

Progress billing also does something sneaky and good for the relationship. It creates natural checkpoints. Every payment milestone is a moment where you both look up, confirm you're on the same page, and keep going. Projects that pay at the end are the ones where a client goes quiet for five weeks and then hates the result.

This is where most owners lose the plot. Invoices go quiet, reaching out feels like begging, so you wait. Then you wait some more. And by the time you finally say something you're irritated, it comes through in the email, and now it's a whole thing with a client you actually like.

Don't be a person about it. Be a system.

Build a ladder. Same one every time, for everybody, no exceptions, no emotion:

Every one of those first four rungs can run without you. Wire it up in Make.com so invoice status in your accounting tool fires the sequence, or use whatever your CRM already ships with. It takes an afternoon. It runs forever.

The reason this works isn't the emails. It's that you stopped deciding. When chasing money is a weekly decision, you'll skip it, because it's uncomfortable and there's always something more interesting on the calendar. When it's a system, it just happens, and you never have to feel anything about it again.

Let me say the quiet part too. The awkwardness you've been avoiding has a price tag. That cleaning company owner had sixty three thousand dollars outstanding because thirteen separate times he decided this wasn't a great week to bring it up.

Any business that sells on terms is making a credit decision, whether it knows it or not. You're just making yours with no information and a lot of optimism.

So put a rule in writing. Anybody new pays a deposit, full stop. Anybody who's gone past thirty days twice moves to prepay only. No debate, no exceptions, no meeting about it. “Our terms for new work are payment in advance” is a complete sentence. And if that costs you the client, go look at what that client has actually been costing you in hours, aggravation, and float.

I have never once had an owner tell me they regretted cutting loose a chronic slow payer. I've heard the opposite roughly nine hundred times.

If you do nothing else with any of this, do three things before Wednesday.

One. Add the deposit line to your proposal template so it's the default and you have to remove it on purpose. Two. Change net 30 to due on receipt and paste in the service charge language. Three. Write down every dollar currently owed to you, oldest first, and send the day 10 email to all of them today.

That third one is the fun part. There's money out there right now with your name on it. Not pipeline. Not projections. Money you already earned doing work that's already finished and already delivered. Most owners I talk to are carrying somewhere between fifteen and forty thousand dollars of it and have never once sat down and made the list.

Make the list. Send the emails. See what the mailbox looks like Friday.

The Tampa guy did exactly that. One round of polite, boring, unemotional follow ups to thirteen accounts on a Tuesday morning. Thirty one thousand dollars collected by the following Monday. Same clients, same relationships, nobody got mad, nobody fired him. He just finally asked.

You're not being pushy. You did the work. Go get your money.

Talk Soon,

Dan

Dan Kaufman
Founder, Dead Simple Growth and Pinnacle Masters

P.S. If you want the exact five email collection sequence I hand to clients, word for word, reply to this with CASH and I'll send it over. It's the least glamorous thing I own and it has probably moved more money than anything else I've written.