Today’s track: Charlie Parr — “Over the Red Cedar”
I’ve been self-employed since 2013.
Thirteen years of being my own boss, my own payroll department, my own HR. And if you’ve ever been a 1099 anything — realtor, contractor, wholesaler, freelancer — you already know the hardest seat at that table: health insurance.
For years I was on the typical government marketplace plans that most self-employed folks end up on. I can’t even remember the name of the plan I had at this point — which tells you something. They all blur together. You pick from a menu of options that somehow feel expensive and thin at the same time, you pay your premium, and you quietly hope you never have to find out what it actually covers.
Then in 2019, I brought on Colleen.
She started doing admin and contract-to-close coordination for my real estate business. If you’ve worked a deal with me since then, you’ve felt her fingerprints on it. And she hasn’t stayed put — over the years her role has grown to where she operates Winner Realty and offers contract-to-close for wholesalers and realtors. Watching somebody grow like that inside your business is one of the best parts of building one.
But this isn’t a Colleen appreciation post — well, it partly is — because one of the most valuable things she ever did for me had nothing to do with a contract.
She turned me on to Liberty HealthShare.
Technically, it’s a religious health share plan. I know how that sounds. You’re picturing an application with essay questions, a statement of faith, maybe a reference letter from your pastor.
There’s one question: Is your body a temple?
It is. You say yes.
That’s it. That’s the theology exam.
Now — when I signed up, it was about affordability. A solid option for a self-employed guy who was tired of the marketplace shuffle. What I didn’t know was that I’d end up stress-testing that coverage about as hard as coverage can be stress-tested.
You all know what I’ve had going on — the colon cancer, the chemo, the scans, the bloodwork, the parade of bills that follows all of it. Nobody signs up for coverage hoping to become a power user. But here I am, and I can tell you: Liberty HealthShare has been great. Through all of it.
I’ll also say this — my sister has been an angel through the whole thing. She’s so sweet, and she’s helped me navigate the entire billing side: getting every bill inputted with the right processing numbers, tracking what’s been submitted, keeping the whole machine moving. If you’ve ever dealt with medical billing, you know that’s not a small favor. That’s a part-time job done out of love.
So consider this a shout-out, plain and simple. If you’re self-employed and you need an affordable, solid health coverage option, hit up Liberty HealthShare. They’ve earned the mention.
And since we’re talking insurance today — that’s the thread, so let’s pull it — let me tell you about my car.
I don’t remember exactly how many years ago this was, but my car was stolen right off the street in front of my house by Bowman Field. One day it’s there, the next day it’s a police report.
My auto insurance was with Eric Fox at Erie Insurance, and they were awesome. They did replacement value on the claim — not some depreciated, sad-math number, but what it actually took to replace the car. I took that check and bought a Subaru Forester that I loved. A stolen car is a terrible week, but the right insurance turned it into a short story instead of a saga. Eric Fox, Erie Insurance. Note them.
Now hold onto that phrase — replacement value — because it’s the key to the back half of this email.
There’s a big shift happening right now with insurance companies, and if you own property, are buying property, or are selling property, you need to know about it.
Here it is: carriers increasingly don’t want to do replacement value on claims anymore — especially on roofs. Instead of paying what it costs to replace the roof, they want to pay a prorated percentage of the roof’s lifetime value. So if your roof is fifteen years into a twenty-five-year expected life, they’re not paying for a new roof. They’re paying you for the ten years of roof you theoretically had left.
Think about what that does to a transaction.
Because here’s how it’s showing up on the ground: on nearly every listing, nearly every inspection, somebody is now saying, “Hey — you need to replace the roof.” It’s like an epidemic right now. Roofs that would have sailed through a few years ago are getting flagged left and right, because the buyer’s insurance company doesn’t want to inherit a roof it might someday have to pay out on.
I had a four-year-old roof that they said had to be replaced.
Four. Years. Old.
So, two pieces of advice, from me to you.
First: if I were you, I’d be identifying insurance companies that are still offering strong replacement value plans. Not every carrier has made this shift yet, and the ones still doing true replacement coverage are worth finding and locking in. I’m going to do some more research on which ones those are, and I’ll report back here when I do.
Second: if you’re selling a property to a traditional buyer, just budget that you’re probably going to have to replace the roof — unless it’s been replaced in the last three or four years. Build it into your numbers up front. It’s a lot less painful as a line item on day one than as a surprise on day twenty-five of a thirty-day close.
Just another angle. Just another thing to be cognizant of in this market.
You know, I talk to a lot of investors — all day, every week. One of the underrated perks of that is I’m always keeping a pulse on things, collectively hearing what’s happening across the board before it ever shows up in a headline. This roof thing is a perfect example. I try to keep my friends and clients well informed, and this newsletter is a big part of how I do that.
So don’t be a stranger.
And it runs both ways — if you’re well informed on something, I want to hear it. Cool things, niche insights, something you’re seeing in your corner of the world that the rest of us aren’t. Tell me about it, and I’ll impart that wisdom to my clients, my friends, and all of you.
Reach out. Schedule a call. I’d love to talk. And if you have anything you’re looking to buy or sell — or you want to do some investing — hit me up. I’d love to chat about that too.
Have a terrific Tuesday.
Happily,
Rob Bergeron
Owner–Realtor at Award-Winning Winner Realty
Schedule a time to discuss your goals, bottlenecks, or whatever’s on your mind:
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PS: Slight refresh tomorrow on The Morning Bergeron, hope you enjoy!