
Wednesday Sep 03, 2025
EPISODE 188 : Handling Late Payments : Strategies and Systems for Smooth Cash Flow
Hey there my friend!
Ever felt like you spend more time chasing up overdue invoices than actually running your business? You’re not alone – over half of us business owners struggle with late payments, and honestly, it can threaten the very survival of our businesses.
In this episode of The Boring Sh!t in Business, I’m getting real about that not-so-glamorous part of entrepreneurship: chasing money.
Here’s what you’ll get when you hit play:
✅ Real talk about why those late payment emails are so awkward (and how they tank your cash flow if you let them).
✅ My absolute must-have strategies for setting payment terms and boundaries from day one – enough with the vague “payment due soon” nonsense!
✅ How to swap out sticky notes and spreadsheets for invoicing systems that actually keep you sane (and make the software play the “bad guy”).
✅ Tips on dealing with clients who genuinely forgot (no shame, we’ve all been there)… and how to handle the serial late payers who treat your invoices like suggestions.
✅ Tools for rewarding your on-time legends AND what to do when you just have to cut those persistent late payers loose.
This episode is the no-fluff, practical advice I wish someone had given me years ago. By the end, you’ll know exactly how to protect your cash flow, keep your relationships intact, and maybe even save your Friday night wine for celebrating, not stress-drinking!
PS – I’d LOVE to hear the weirdest excuse you’ve gotten for a late payment. Comment or DM me so we can commiserate (and have a laugh).
Ready to spend less time chasing invoices and more time doing what you love? Go check out the episode now!
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