At 17, he rented Hamptons mansions monthly then sub-let them to prom groups each weekend, charging the same rate per night. He misled homeowners about the purpose and admits the whole thing was sketchy, but says it taught him negotiation and risk-taking before he knew better.
I've been an entrepreneur now since I was 17, 18 years old. When I was in college, I met one of my best friends who sadly he passed away recently, actually. He brought me an opportunity where we would rent out mansions in the Hamptons over the summer. And then we would, every weekend, we would rent the house out to prom groups for them to come and party because they weren't able to get houses. There's a little bit of a sketchy business, like we would go to these homeowners and we'd say, hey, you know, we have our family coming in from Europe, we need this house for a month. They'd say, all right, it's $20,000 for the month. And then every weekend we would rent the house out for $20,000. And that was kind of my first business venture. And it was a lot of things wrong, but it was fun. I learned a lot from there. We did a favor for a prom party that they couldn't get a house.
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