Chasing money without burning the bridge.

The hardest part of running a trade business isn’t the trade. It’s calling a nice person who owes you $1,900 and finding words that get you paid without losing the next job, the referral, and the wave at the hardware store. So most contractors don’t call. And the invoice ages.

Depersonalize the chase

The fix is structural: make the reminder come from the system, not from you. When a reminder text arrives automatically on day 3, it isn’t you hassling anybody — it’s just how the billing works, the same way the power company works. Nobody resents the power company’s reminder. They pay it.

Let the system be the bad cop, so you never have to be.

The 3-7-14 cadence

• Day 3 — the nudge. “Friendly reminder — invoice #142 for $650 is ready to pay here.” Most invoices die here, paid.
• Day 7 — the check-in. Same link, one added line: “Let me know if anything looks off.” It offers an exit ramp for honest confusion.
• Day 14 — the direct one. Still polite, now specific: “This one’s two weeks out — can you take care of it today?”

After day 14, it’s a phone call — and because the system sent the first three, the call is rare, and you arrive as the reasonable one, not the nag.

When they really can’t pay

Sometimes the money genuinely isn’t there. Take a deposit next time, but today: offer two dates. “Half Friday, half on the 1st” converts a dodge into a commitment, and a commitment with dates is something your reminders can chase for you.