Sometimes, perspective shifts come when you least expect them. For me, it wasn’t during a deep conversation or after reading a finance book— it was at a bar in Vermont, halfway through a drink, after a long day of skiing.
it was at a bar in Vermont, halfway through a drink, after a long day of skiing.
In early 2023, a few friends and I took a trip to Vermont for a weekend of skiing. Nothing groundbreaking: just solid runs during the day, après-ski drinks, and the essential post-skiing amenity – a hot tub. We stayed at a small bed-and-breakfast called the Bromley View Inn—a cozy spot close to the hill that checked all the right boxes.
On our second night, we were having drinks at the inn’s bar and struck up a conversation with a group of guys who looked to be around our age, late 20s. A little while in, one of them got up, walked behind the bar, and casually poured himself a drink. Naturally, we joked that he probably shouldn’t be doing that. He replied coyly,
“Why not? I own the place.”
That sentence stuck with me. Until then, I had always seen property ownership as something reserved for people who already had wealth. That night showed me that wasn’t true. Here was someone who looked like me, was roughly the same age, and yet owned an entire inn. That single realization was more valuable than any business book I could’ve read. You don’t have to be middle-aged, rich, or plain lucky to own real estate.
You don’t have to be middle-aged, rich, or plain lucky to own real estate.
The real wake-up call didn’t happen until I got back to New York. I remember walking into my studio apartment in Brooklyn and staring at my $3,500 rent bill. I’d always accepted rent as part of life—especially in a city like NYC—but suddenly, it felt like setting fire to nearly half of my take-home pay every month.
I wasn’t investing in anything. I wasn’t building equity or moving closer to any financial goals. I was just maintaining the status quo.
That realization hit hard: Why was I paying someone else’s mortgage when I could be investing in my own future?
Why was I paying someone else’s mortgage when I could be investing in my own future?
That ski trip didn’t instantly turn me into a real estate investor or magically boost my net worth. What it did was force me to question the way I was living—and whether rent should be a “given” in my life.
The next steps weren’t glamorous. They involved breaking my lease, moving back home with my mom for six months, learning everything I could about real estate, financing, and critically... how to live with my mom again. It was uncomfortable, and there were sacrifices involved, but that’s where the real story begins.
What’s Next?
In the next post, I’ll discuss about the sacrifices it took to go from paying rent to buying my first multi-family property—and how moving back in with my mom wasn’t just humbling, it was necessary to make the numbers work.
This isn’t some overnight success story. It’s the start of a longer journey—and if you’re following along, I’ll show you exactly what it takes to get there.
Follow for the next chapter.
