In luxury real estate, certain transactions leave a lasting imprint—not because of the price tag, but because of the people, timing, and perseverance behind them. For Dante DiSabato, one deal intertwined with a personal milestone became a defining chapter, while another period of professional uncertainty reshaped his approach to the business entirely.
Below, DiSabato reflects on the deal he would do again, the one that nearly pushed him out of the industry, and the lessons that continue to guide his career today.
HR: The deal I’d do again—set the scene. What was the deal, and why did it matter to you personally?
Dante: “In hindsight, it’s funny because I was engaged to my then fiancée, now wife, back in 2020, and we would walk along the sidewalk on Naples’ Gulfshore Boulevard. And every time we would come upon this gorgeous old house, a 1926 Addison Mizner-designed estate on the beach, and Hillary would say that she wished we could get married there.
A few weeks or perhaps months go by, and I’m at the car dealership buying a new car and I start chatting with the gentleman next to me in the showroom. It takes no time, and we’re talking like old friends and decide that we should all grab lunch together. Somewhere in the course of the conversation, he mentions his address—you guessed it—he owned the house on Gulfshore Boulevard. And it turned out that he and his wife were happy to let us get married on the property.
During the process of planning the wedding, I came across a buyer who was interested in buying that property before our wedding. They ended up closing on it before our wedding, but they honored the agreement, and we got married there. We are still great friends with both parties, and I have handled other deals for both. In fact, that buyer decided to sell after Hurricane Ian, and I handled the sale again.”
HR: What did you do on this deal that you still do today—something that became part of your playbook?
Dante: “That sale was a win-win-win. And while I don’t try to get married during every negotiation, I am definitely working hard to do my best for my clients. That’s just who I am. I love the job. I love building relationships. That’s what it’s all about.”
HR: Describe the deal that almost broke you. When did you first feel that something wasn’t right?
Dante: “My very first deal. It didn’t almost break me—it saved me. If it didn’t happen, I honestly think I was ready to quit for the first time in my life. I hadn’t sold anything in a year… A whole year. And that sale fed me for almost another year until my next sale. Naples was not an easy market to break into at the time—especially if you were young. Even though there are a lot of fresh deals, there aren’t a lot of big deals, so I get that it can be discouraging. But if you are professional and dedicated, and hard-working, you have a chance.
Looking back, that deal was the one that kept me going. Now, more than 17 years later, I’ve had well over $1 billion in sales before turning 40 years old, and $2 billion is on the horizon. But it’s amazing how that sale was the difference-maker for me. So it’s not about a deal almost breaking you, it’s about going on—persevering.”
HR: What did this deal cost you—time, money, sleep, confidence?
Dante: “This is a deal-by-deal business. Each seller and buyer are different. And that’s what I love about it—you are learning every day. You get more confident in selling, in relationships, in dealmaking. Every deal is unique. You put together a buyer and a seller and facilitate it with another Realtor most of the time. That’s a lot of moving parts and interesting personalities multiplied by however many homes you’re involved with. How great is that?”
