Today's track: Dirty Projectors — No Intention.
Growing up, my family had a mantra:
If it doesn't say you can't, then you can.
It sounds like a loophole. It is a loophole. And it came from one.
In kindergarten, I started competing in this thing called Odyssey of the Mind. It later became Destination Imagination — DI, if you're familiar. It's basically competitive creative problem-solving for kids. You get a challenge, you work as a team, and you perform.
Our first performance was supposed to be eight minutes long.
Ours went thirty-two minutes. We were dressed as ducks. We were five years old. Nobody cared about winning at that age — everyone was just doing their thing. But I kept doing it. All the way through my sophomore year of high school, with basically the same group of friends.
We always gravitated toward the improv challenges — the ones where you draw random things, you have to incorporate historical elements, and you solve problems on the spot within a time limit. And here's the part that stuck with me more than anything else:
They encouraged you to look for loopholes.
Not cheating. Loopholes. Anything that wasn't explicitly against the rules was fair game. You were rewarded for being clever. For reading the fine print. For finding the angle nobody else saw.
My sister did it too, with her own group of friends. My dad was a judge — he's an engineer, so he judged the structural challenges. It was a family thing.
Our team ended up going to globals — the first team from Springboro to make it in thirty years. They actually put our team's name on the signs entering town. That was pretty surreal for a bunch of kids who started out dressed as ducks.
And that mantra — if it doesn't say you can't, then you can — it wasn't just a cute thing we said. It wired my brain for everything that came after.
In 2007, I hadn't set foot on the University of Kentucky campus yet.
I was a senior in high school in Springboro, Ohio. I knew a handful of people going, but that was it. No deep connections, no older sibling to show me around. I was just a kid from Ohio who got accepted and figured — why wait?
So I started the graduating class Facebook group for UK.
Not because I had some grand strategy. Not because I was "building a brand." I just thought it would be cool to know more people before I showed up. So I made the group, invited everyone I could find, and started talking.
People joined. A lot of people. We started doing what college kids do — asking dumb questions about dorms, comparing meal plans, arguing about whether you really need a car on campus.
But then something happened that I didn't plan for.
I made a friend in the group. I was interning with the Cincinnati Reds at the time — I actually built all the party deck furniture out in the outfield, and it's still standing after all these years — and we ended up going on a double date to a Reds game before school even started. We stayed friends all through college. I was in his wedding. And just last week — over a decade later — I had a meeting with him. He's doing incredible things in the engineering world.
All because I made a Facebook group. Nobody told me to. Nothing said I couldn't.
But it wasn't just one friend. That group created a web of relationships across campus that opened doors I didn't even know existed. And that same instinct — just putting myself out there and being open to what comes back — is what carried me to Louisville. It's opened doors here too. Connections into projects I never would've found if I'd kept my head down and stayed quiet.
At UK, I started doing the same thing — but with a blog.
It was called The Room by the Pool.
Every day, I'd read the news — just scan everything I could find — and then write up what I thought was interesting. That's it. No niche. No strategy. No "content pillars." Just: here's what's happening, here's what I think, see you tomorrow.
A thousand unique visitors a day.
A thousand people, every single day, showing up to read what some college kid thought about the news. Not because I was an expert at anything. Because I showed up consistently and had something to say.
Sound familiar?
That blog was the prototype for the newsletter you're reading right now. I just didn't know it yet.
Now here's where it gets good.
Years later, I'm in Louisville. I'm in real estate. And I start running comps for local wholesalers and investors. Not because anyone asked me to. Just because I thought it was useful and I wanted to be helpful.
I never ganked anyone's deals. Ever. I'd just say, "Hey — if you end up getting this under contract, I might have a buyer." That's it. No angle. No catch.
And eventually, I said something that changed everything:
"Hey — instead of working against each other, let's work together."
They gave me their buyers lists. All of them. I combined them into one mega list and started sending out their deals on my website. If I found a buyer, I charged $2,000. If I didn't, I didn't charge anything.
First year: $42,000. From a website.
And here's the part that gives me chills every time I think about it. My buddy Nick — my weightlifting partner — we'd talk about ideas while lifting, in the hot tub, in the sauna, walking out to the parking lot. Just two curious guys exploring ideas. Nothing formal. No agenda. Just riffing.
And one day, out of nowhere, Nick goes: "Yo. That idea you had? I made you a website."
Nick created something that made so many wrinkles in the rest of my life. How awesome is it to have people like that?
That website became OffMarket.deals.
That buyers list became the morning email list.
That email list became this newsletter.
That newsletter now reaches over 40,000 people every single morning.
Because I put myself out there. Because I shared instead of hoarded. Because I said "let's work together" instead of "that's my deal."
Collaboration is key to ascending. Let the experts expert. Nick's an expert at building things — I'm not. The wholesalers were experts at finding deals — I wasn't. But I was good at connecting people. So I stayed in the space where I excelled and let everyone else do the same. That's not weakness. That's leverage.
None of this was planned. There was no ten-year strategy. No business plan that said "Step 1: dress as a duck in kindergarten. Step 47: build a newsletter with 40,000 subscribers."
There was just a kid who was taught to look for loopholes. To find the angle nobody else saw. To assume that if nobody said you can't, then you can.
And every time I acted on it — every single time — something came back that was wildly out of proportion to what I put in.
Nobody told me I couldn't start a Facebook group for a school I hadn't attended yet. Nobody told me I couldn't write a daily blog as a college kid with zero credentials. Nobody told me I couldn't combine everyone's buyers lists into one mega list and help them sell faster.
So I did. And here we are.
If it doesn't say you can't, then you can.
(Missed Friday's issue? The Obsessed Will Inherit the Earth — on obsession, AI, and why the credentialed are in trouble.)
See you tomorrow.
Enthusiastically,
Rob Bergeron
Owner–Realtor at Award-Winning Winner Realty
PS: Hit reply and tell me — when did putting yourself out there lead to something you never expected? I want to hear your version of this. Everyone's got one.
PPS: My friend Jamie is down in Belize homeschooling her kids Alex and Alexia — and they could really use a used laptop to share for school. If you've got an old one collecting dust, hit reply and we’ll figure out how to get it down to her. Would mean the world!
PPPS: Tried out a new Indian fast casual place called Zila Indian Kitchen. It's in the Vogue Center. It's going to do very well — Louisville has its next hit on its hands. I’ll be taking a bunch of my lunch meetings here!
