Three Contractors, One Pattern: When Payment Never Comes

D.K. And Tree Podcast

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Some deals glitter at the start and ruin you by the end. We open up about three real stories from people we know—a contractor, a photographer, and a dry cleaner—who took on marquee work, did the job, and then hit a wall of delays, lawsuits, and nonpayment. The pattern is hard to ignore and harder to carry when payroll, vendors, and families depend on checks that never arrive. This isn’t about partisan point-scoring for us; it’s about conduct, leverage, and what happens when power treats contracts like suggestions.
We walk through the contractor’s three-and-a-half-year chase that ended in a partial settlement and a heartbreaking final act after he paid everyone else first. We talk about the photographer who only got paid after filing suit, giving up margin to legal fees and time. We recall the dry cleaner who almost lost his shop and, worse, his belief that doing good work would be enough. Along the way, we unpack what these cases teach about risk management for small businesses: front-loaded deposits, milestone payments tied to deliverables, escrow, payment bonds, and clear late-fee language that discourages stall tactics. We also stress real-world due diligence—checking vendor references, reading litigation histories, and talking to peers who have recently billed and collected from the same client.
If you’ve ever waited too long for a check, this conversation will feel close to home. We share practical ways to protect cash flow, set exposure limits, and know when to pause work. We also talk about the emotional toll of chasing what you’re owed and why solidarity matters—how sharing information, refusing predatory terms, and standing together gives small businesses leverage they rarely get alone. Subscribe, share this with a business owner who needs it, and leave a review with your best red flag to watch for. Your story could spare someone else from a painful lesson.

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2. Why I Never Backed Trump (00:00:21)

3. The New Jersey Contractor’s Collapse (00:01:19)

4. Photographer Paid Only After Lawsuit (00:03:48)

5. Dry Cleaner Hurt By Nonpayment (00:04:46)

6. Moral Barometer And Cult Loyalty (00:05:12)

7. Broader Lessons On Who You Trust (00:06:54)

8. Lawyer Up Tactics And Power (00:08:32)

9. Stand Together And Final Wishes (00:09:37)