I Lived At a Motel One Summer Because My Dad Was a Real Estate Investor
Cozy Cabins Was Not That Cozy, But It Cash Flowed
I can’t even count the number of houses that I lived in when I was with my dad. My dad, like me, was an attorney, but his passion was real estate investing. He bargained, traded, bartered, and bought at courthouse steps. This meant we moved around a lot, especially in the summer.
One summer we lived at a motel - Cozy Cabins. We didn’t live there because we were renting. We lived there because my dad owned and operated it for at least one summer. It was a long summer, but fortunately, I spent most of it in the Berkshires at camp.
Cozy Cabins, located on Montauk Highway, Route 27, three miles east of Bridgehampton on Long Island, offered one- and two-bedroom units, kitchenettes, and complete baths with hot showers. It was 1 1/2 miles from Ocean Beach. We offered rentals by the day, week, or month, and were open from May 1st through November.
My dad was way ahead of his time. If Cozy Cabins is still there, someone is probably trying to turn it into a boutique short-term rental resort. He invested for appreciation, cash flow, and because it seemed like a good deal. I wish I could ask him how this investment turned out and why he sold it, but he passed away more than twenty years ago.
This was more than forty years ago, so my memories are sparse, but I do remember that there were two very popular bars right across the street - The Swamp and The Annex. Nightly rooms were a thing. The cabins were not cozy; they were purposeful.
I remember my stepbrothers and I trying to negotiate a cabin for ourselves. My dad laughed and then took us to see one. We immediately declined. The cabins were not cozy, but they cash flowed. This was my dad. This is who I learned everything about money and real estate from.
If you want to build generational wealth through real estate investing, you have to get comfortable with being uncomfortable, especially in the beginning. If scaling to millions were easy, everyone would do it. It’s not. It takes vision, skill, tenacity, grit, and a willingness to bend to your properties.
I don’t know why my dad bought and sold Cozy Cabins, but I know he wasn’t afraid of failure. He used money and real estate as a vehicle. That vehicle was meant to benefit me and my sister, but he also found the time to enjoy his real estate until he sold it.
He was never emotionally attached to a piece of real estate, which drove my stepmom and us crazy at times, but then the next house was better. Perhaps this summer at Cozy Cabins was an anomaly, as it was no better than anything, despite the main house being decent. But it cash flowed.
Some questions for you to consider:
How uncomfortable are you willing to be to build a good foundation for generational wealth?
How open are you to looking at outside-the-box assets?
How many real estate investors do you know who have been doing this since before the year 2000?
Successful real estate investors are nimble. Many of them fail. When they do, they accept it and move on to the next opportunity. What’s your next opportunity?
This Substack replaced my long-running newsletter, making it easier for me to publish on demand.