Freelance to Founder Is It Best to Drop Late-Paying Clients?
Nov 18, 2025
Chanda Koston, a Navy veteran and business strategist, joins the discussion to navigate the tricky waters of managing late-paying clients. She emphasizes the importance of setting clear payment terms, including requiring upfront deposits for new clients. The duo also explores how building recurring revenue can stabilize cash flow and reduce stress. They provide practical tips, like securely storing payment details to ensure timely payments, and advise freelancers on whether to keep or let go of challenging clients.
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Require Upfront Payment For Chronic Late Payers
- Draft a new contract requiring a deposit or full prepayment when a client pays late repeatedly.
- Invoice before work or require a portion up front to protect your cash flow and continue the relationship.
Late Payments Often Come From Process, Not Malice
- Late payments are often non-malicious and stem from organizational processes, not spite.
- Small business owners should communicate how delayed cash affects them because corporate clients may not realize the impact.
Keep A Card On File To Guarantee Payment
- Take a client's credit card on file (via a secure processor) so you can charge invoices when they become due.
- Use Stripe or similar tools to protect cash flow even if you bill after delivery.