Ben Rego

The chats remind Ben of his own childhood when he would try to guess the square footage of homes he was passing with his father, Buddy Rego, president of Rego Sotheby’s International Realty. That interest never waned—and nor did the close bond with his dad, whom he credits with instilling in him a fierce work ethic and describes as “one of my favourite people to hang out with.”

Ben closed on thirty-eight property sales in 2022—understood to be the most of any island realtor—representing roughly 20 percent of the market share. He tells how his father, on seeing the figures, told him: “Jeez, mate, you’re a machine.” Ben says: “Him calling me a machine—that was super special to me, deep down. I just laughed it off in a second, but I still think about that. It makes me want to push on more.” Ben happily admits that making his father proud is a huge part of what drives him, along with providing for his own family —wife Amie, little Harry, and daughter Riley, aged one.

Alongside that is a desire to make the most of the many opportunities he’s been given and a straightforward passion for what he does. “I feel like I was honestly born to do it but not necessarily just to sell real estate— but I was born to work hard for my clients, for my clients’ best interests,” he says. “I think it would have been transferable into other industries, with that same mentality of really working for the client.”

Ben’s ancestors came to Bermuda from the Azores, and his grandfather, Benjamin Rego Sr., founded Rego Ltd. in 1949—the island’s first and now longest- running real estate company.

Benjamin Sr. eventually sold the business to son Buddy, who partnered first with global property firm Knight Frank and then with luxury brand Sotheby’s International Realty. The door was always open for Ben to join the business, but he wanted to do so on his own merit. After university, he worked for a Sotheby’s affiliate in Boston for several years, assisting three of its top agents and learning all he could about the industry. During that “invaluable” apprenticeship he saw how the best agents developed their own personal brands—a skill he has since used to great effect in Bermuda, gaining thousands of followers and likes for his @regobermy property posts on social media sites such as Instagram, LinkedIn and Facebook. He even has his own slogan, ”Patience. Positivity. Persistence.” and a podcast, Keys to the Rock, with his friend, chartered surveyor Daniel Woods.

When Ben returned to Bermuda permanently in 2015— having already passed his real estate licence exam on a secret 24-hour trip back to the island— he joined Rego SIR in a market- ing role and became an agent a couple of years later. He’s since achieved accolades as the company’s top selling, renting, listing and gross commissioned agent, earning him a promotion to sales agent manager. Ben leads a weekly team meeting, trains other agents and continues to sell property, be it a house worth under $400,000 or a mansion for more than $10 million. “I’m of the mindset of a luxury white-glove service no matter what the price point,” Ben says. He adds: “One of my biggest strengths is just the ability to connect with all types of people. I have best friends from all walks of life, whether it’s in Bermuda or around the world.”

His days start very early and finish late, but he wouldn’t have it any other way, describing himself as an “unbelievably organised” professional who is “just on the ball” and always responsive. “It is tiring but it’s very fulfilling because I want to give my kids, at the very least, the life that I was able to have and the opportunities and experience that I was able to have.

“But I want to do it on my own terms and my own sweat equity.”