Three Contractors, One Pattern: When Payment Never Comes

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.

Chapters

• 0:00 Holiday Greeting And Setup
• 0:21 Why I Never Backed Trump
• 1:19 The New Jersey Contractor’s Collapse
• 3:48 Photographer Paid Only After Lawsuit
• 4:46 Dry Cleaner Hurt By Nonpayment
• 5:12 Moral Barometer And Cult Loyalty
• 6:54 Broader Lessons On Who You Trust
• 8:32 Lawyer Up Tactics And Power
• 9:37 Stand Together And Final Wishes

Transcript

D.K: 0:10

All right, good morning, good morning, happy holidays, everybody. I hope your Thanksgiving was doing good and I hope everything's going well. If your boy Damon, I'm here with the DK and Tree Podcast. Man, I tell you, when I hear the tongue foolery out here, I try to spread this information out. And basically be careful who you're making deals with because sometimes those deals may not work out good for you. I saw this story, so of course, you know, I'm gonna come share it with you all because again, I want you to listen to this for yourself because hey, no better than uh hearing it from the horse's mouth.

Speaker: 0:47

So somebody asked me yesterday if I ever gave Donald Trump a chance. And I said no. But you have to understand why. The reason why I didn't give Donald Trump a chance is because I own a company that works a lot of contractors, do estimates and whatnot for contractors, bought other support for other folks in the industry, but that's enough set. Anyway, what happened was uh a buddy of mine that was a contractor up in New Jersey called me up one day and said, Hey man, uh I got this opportunity to do this business with Trump, and it's just it's huge, and I I think I'm gonna do it. And I said, Well, I I get that you're gonna do it, but it might be in your best interest to think that through because you know the honest truth is that dog bites, and he said, Yeah, I understand, but I mean I'm gonna write a tight contract and blah blah blah, you know. So he he takes the gig. And he tells me later he's having a little bit of problems getting getting uh getting paid. Fast forward three and a half years, he still hasn't been paid his $3.5 million. He's been worn down pretty awfully, and Trump's attorneys said that they would pay him $1.2 million, and that was it. He took the $1.2 million the day that that showed up as certified funds. He took the title to every truck he owned. He owned a pretty decent-sized company. He took a bill of sale for a bunch of other equipment, generators, bark welders, all kinds of stuff. Ladders, you name it, chip crane. He went to another place and he sold all of that and walked out with certified funds. He went to the bank, he deposited those funds into the bank. Then he gave a list of amounts and people and companies that he needed to cut checks to, and they cut certified funds to all those individuals. He took those checks, he went down to the post office, he individually sent every one of them out in the by express mail. And then he went home and he blew his brains out. He blew his brains out because Donald Trump decided to take advantage of the little guy, and he couldn't handle the failure. Fast forward a couple of years later, a friend of mine who is a professional photographer picked up a job for $120,000 from Trump to take pictures of his property. Three months after it was done, he couldn't get paid. He ended up having to file a lawsuit, and only after the lawsuit was he paid. So he pretty much had to be a pretty big haircut. And another friend I have down in Boca had a father who was in the dry cleaning business. And years ago, he did dry cleaning work for Donald Trump. Donald Trump never paid him, and he just about lost his business, and he did lose his spirit, and he was never the same. So when you ask me if I'm ever gonna give Donald Trump a fair shake, no. Because he didn't give anybody else a fair shake. He has no moral barometer. And you can tell that truth that I just told you. That's true. Pain that I'm talking about. The people I know are new. You can tell that to people in the Trump cult. And it's like they can't even hear you. I'm never going to understand this. Ever.

D.K: 6:18

Three people he personally knew that went through business with that guy. I'll leave him nameless because you already heard what he who he said. But he said one guy unallowed himself. Another one had to sue to get their money, and one almost lost their business. Because this guy just didn't care about nothing but himself. But let's look at this on a broader scale. You gotta be careful who you do business with. Who you make deals with. Make deals with someone that can't be reversed. You're supposed to be a business person, then it's supposed to be business. It's not personal, it's business, right? People have business, people have families, people have lives that goes on every day. And for you not to pay these people, it's sad. It's sad. But you're the leader of the free world now. And you're still making people suffer. This is my opinion, my opinion only. I don't speak for anyone or any entity. Only me. Like I said, I normally don't dive onto politics. I don't. But in this situation, it's sad. Like I said, you just have to be careful who you make a deals with. You have to be careful who you talking to. Regardless of a contract, regardless of anything. Because that person could just take you for everything you work. I heard some old things and um I heard this saying back a while back. They said that in his case, he will lawyer up enough to where you'll quit. Because you don't have enough lawyers to outlawyer him. So people just give up. And that's sad. That's sad. But remember, I always say power in the people. If you all stand together and band together, you got a fair shot. You got a fair shake. But in them three stories that that man just described, you could hear the emotion in his voice. How hurt and sad he was that this one guy could do this to this many people and make them suffer. Because you are ripping someone off. That's truly sad. But I just wanted to come share those three stories with you. I hope each and every last one of you have a prosperous holiday. And if you don't get the chat before Christmas, Merry Christmas to you, if you wanna get the chat before then, happy new year to you. I'm signing off.