I’ve had ‘Bruised’ on repeat this week. The Bens wrote it about a relationship that didn’t survive —Ben Kweller and Ben Lee in support. Ben Folds on piano, wearing the whole thing on his sleeve. I’m stealing it for something else, because bruised is bruised. Doesn’t matter if it’s your heart or your balance sheet. Something hits you, and even after the mark fades, you remember exactly where it landed.
It’s because I keep getting the same phone call.
Different name every time, same shape. Somebody’s cash flow doesn’t work anymore. Somebody’s insurance renewal came in at double what it was last year. Somebody’s property tax bill jumped and the spread they were counting on disappeared with it. Somebody grew fast in 2021 and 2022, took on debt that made sense at the time, and the time is over.
Some of these calls are quiet — somebody who’s embarrassed, who waited three months before finally texting me because they didn’t want to say it out loud. Some are loud — a call at 9pm because a partner just said something that changed everything. I’ve had both kinds this year, more than usual.
I’m not going to dress this up. A lot of people are having a bad time right now.
W-2 people are getting stretched by fixed incomes that don’t move while everything around them does — groceries, insurance, gas, all of it climbing while the paycheck stays flat. Investors are getting bit from two directions at once: insurance premiums up, property taxes up, and the math that used to cash flow on a rental just doesn’t anymore. Some of that is the market doing what markets do. And some of it — I’ll say this plainly — is people who grew too fast, over-leveraged, or weren’t pragmatic when they had the chance to be. That’s not me being harsh. That’s just what’s true, and I think a lot of us know it, even about ourselves.
Inventory here has been climbing steadily since spring, and we’re well past 4,000 active listings now. That number doesn’t fix itself. More options for buyers usually means less patience for a seller’s problems — and less patience is exactly when a shaky deal stops being shaky and starts being a real one.
Here’s the other thing I want to say, and I mean it.
It’s okay to have a bad time.
I’ve had a bad time. I’ve mentioned pieces of this before, but I’ll say it plainly again, all in one place. I’ve got a lawsuit with Joe and Kim Worth. I’ve had cancer. I had a wedding planned in Italy that got called off. I lost my mom to alcoholism when I was eight years old. None of that makes me special. It just means I’ve had practice. Life happens. It happens to everybody eventually, in some form or another. What matters isn’t whether it happens to you — it will. What matters is how you handle it when it does.
And it’s scary. I’m not going to pretend it isn’t. But you can’t manage what you won’t look at. You have to shine a light on it, the whole thing, even the parts you’d rather not look at directly. Scoop it under the rug instead, and you don’t end up with a smaller problem later — you end up with a bigger one, with interest. I think a lot of people are finding out right now that “later” is now.
Here’s the part that keeps me useful in situations like this: people bring me their problems constantly, and almost every time, they think their situation is one of a kind. Most of the time, it isn’t. I’ve seen it before — plenty of times — and I know how to work through it. Some problems are trickier than others, and I hate that anybody has to deal with them at all. But I love using my brain to help solve them. I love pulling in my smart friends and my resources and figuring out the actual way through, not just the comfortable-sounding one.
So I guess this is kind of an altar call. If you’re in a difficult partnership right now. If your cash flow has gone negative and you know it. If something you own is headed for a short sale. If you’re sitting in a pre-foreclosure and haven’t told anybody yet. If you’re stuck paying hard money right now and you’re throwing bad money at bad money just to keep the lights on — I’d love to talk. No charge for the conversation. Thirteen years in this business, and the adversity I’ve been through isn’t worth much to me unless I can use it to keep somebody else out of the ditch.
Yesterday I put out my Top 25 People to Meet in Real Estate — link’s here if you missed it. Every single one of them is somebody I’d trust with a problem like the ones I just listed. That list is a resource. Use it.
The best work I do is usually invisible. It’s the partnership that got restructured before it blew up completely instead of after. It’s the disaster that just — didn’t. Nobody throws a parade for a problem that got solved quietly, and I don’t need one. I just want to be the guy you call before it gets worse instead of after.
Here’s who I think wins the next few years: the nerds. Not the credentialed — the curious. The ones who find out what the other smart people are already doing, or who just sit down and ask themselves, “what can I actually do about this?” At Winner Realty, we teach agents and clients how to do the harder stuff — lease options, novations, assignments, land contracts, 1031 exchanges, even how to invest in oil and gas. There’s more red tape with all of it, I won’t pretend there isn’t. But if you learn to do it properly, it’s a real resource, both for you and for anybody you’re working with. Most realtors and investors stop at the surface. I think that’s a mistake.
Every new rule, every piece of legislation, every fresh problem — most people groan about it. I look at it differently. Every new problem is an opportunity, because everyone else has to solve the exact same one at the exact same time. That’s the kind of thing we love. We love change, because it’s our chance to think our way through something and bring a real solution to the market before anybody else bothers to find one.
Same with insurance. Same with taxes. Everybody’s getting hit with the same headline, but almost nobody sits down and actually works the numbers on their own situation — what a reassessment appeal could do, what restructuring the debt could do, what selling one property to save three could do. The people doing that math right now are the ones who’ll still be standing in twelve months. The people hoping it fixes itself usually aren’t.
That’s true in business, and it’s true in life too. I was on the board of KREIA, and there was a lawsuit there — not fun to go through at the time, but I learned from it. Now I can help clients figure out when a lawsuit is actually worth fighting and when it’s worth letting go and just being done working with somebody. Both are real answers, depending on the situation. Knowing the difference is most of the skill.
So — bruised or not, I’m still standing. I’ve taken a few hits by now. If you’re sitting with one right now, you don’t have to sit with it by yourself.
📊 Yesterday’s poll: 4–6 hours a day won it — 42.86% of you living there. “I’m scared to look” and “2–4 hours” tied behind it. Only two of you claimed under 2 hours. I don’t believe a single one of you.
When trouble shows up, what's your first move?
Warmly,
Rob Bergeron

Owner–Realtor at Award-Winning Winner Realty
Winner Realty | OffMarket.deals | Property Partner Data Company
Schedule time to discuss your goals, bottlenecks, or whatever’s on your mind — book me here.
PS: If you’re in the market, here’s where I’d start looking. All four-bedroom-plus single family homes under $277,000. Every multifamily property we’ve got available right now. Land deals with seller financing on the table. Available STRs — look hard at the new tax changes before you buy. Everything Winner Realty has listed right now. And OffMarket.deals just dropped a batch of new off-market additions — check them out.
PSS: Round 6 of 12 today. Half way done. Time flies when you’re having fun! ←-truly!
PSSS:
Under performing
Sky diver
Unless target
Is bland
If you need a game ball
I’ll give you a hand
Where ever I am
Where ever I am
