Ben Rego has been entrenched in the real estate industry ever since he was a child with both grandfathers and parents having successful careers in the business. Ultimately, it is his honest, personable manner and energetic big city experience from his years working for a Sotheby’s affiliate in Boston that keep him as passionate and motivated as ever, striving to always be innovative and constantly available at any time for his clients and their real estate goals. He specializes in what he calls ‘Patience, Positivity, Persistence’ as his business motto, while the most important element will always be putting the needs of his clients first and establishing true value and a relationship that extends beyond any one transaction. Ben currently lives in Bermuda with his wife, Amie, and son, Harry.


1. What is your favourite Bermudian tradition?
Without a doubt, Cup Match, and all of the history that it stands for! I just love that although we all have our differences in terms of which side of the island we support, never is the island ultimately more united and full of joy, celebration, and proudly displaying our culture.


2. Where is the best place for a fish sandwich?
Cup Match because it never tastes so good as when walking around on a warm holiday weekend, but besides that then Art Mel’s!


3. Where is the best place for sushi?
Got to give this one to Harbourfront! I’m a massive sushi fan, and a huge foodie in general. I would say that the Togarachi Roll at Harbourfront is perhaps my favourite single dish that anywhere on the island creates for any type of cuisine.


4. What’s the most Instagram-worthy place in Bermuda?
I’d love to say all of the lovely homes that I am honoured to represent the sale of, as they all have their own unique features and elements that my media team and I love to photograph and video. In terms of a public “Wow!” location, I would say Castle Harbour and our crystal clear ocean.


5. What is the best advice you’ve ever gotten?
This is a tough one as I am always looking for advice and a different perspective from others who can provide value to my life and business, but I would say my grandfather, Benny Rego, stating, “Plan your work and work your plan!” Being determined and always finishing the job in the right way is crucial.


6. What do you like most about yourself?
I think I’m proud of the professional mentality I have, but I do hope that I can learn to slow down and be satisfied at times. I would think that I am someone who can relate to all types of people from all local to global backgrounds, as I am someone who truly, deeply cares about others and their happiness/success.


7. What do you like least about yourself?
I am on my phone a lot. It is a blessing and a curse as I think it is essential to be prompt and efficient in real estate, but sometimes I need to give Mr. Outlook a break on the emails and get back to people later during certain moments. I try as best as I can to not work much when in front of my son in the evenings as I do not want him having a misconception about what daddy is doing and wanting to stare at screens himself since he is my mini-me!


8. What keeps you up at night?
I am constantly waking up to take notes on what to remind myself to do the next day, or who to check in with, or what home I’ve come to realize is perfect for someone. Besides that, it is my little 1-year old son, who some nights is a better sleeper than other nights!


9. What’s your favourite thing to do on Sunday?
Family is by far the most important thing in my life. My wife, Amie, and our little son Harry and I love going to Huckleberry for brunch and then on a family outing to never stop exploring our island and seeing Harry react to it all.


10. How long have you been in Bermuda?
I was born and raised in Bermuda. After University in the US, I worked in Boston for a prestigious real estate brokerage to gain invaluable experience from 2011-2015. I have been back working in Bermuda full-time in the real estate industry ever since.


11. What was your first job ever?
I used to rake the 9 beaches at the 9 Beaches Hotel and work in their laundry and landscaping departments one summer. I’ve had all sorts of jobs during my teen years, everything from being an intern at various companies, to even flipping burgers for the sailing camps at the Royal Hamilton Amateur Dinghy Club.


12. Who was/is the most influential person in your life?
That without a doubt is my father. We are similar in many ways but very different in others. His tough love attitude and strong encouragement of me has always made him someone I want to impress whether it was for school grades or now as I grow in the business. No matter what success I might have achieved, it is always ‘on to the next one’, because working hard is expected. We may butt heads at times, but ultimately, he is my best mate and my competitive go-getter mentality is all because of how he has raised me.


13. Do you ever get island fever?
I do at times, as traveling is one of the most eye-opening experiences that I feel very fortunate to have done. As someone who has a passionate love for the arts, different cultures and food, I love trying new things and interacting with others, so whenever my family and I travel we always dive into the local scene head first.


14. What’s your favourite thing in your office?
Our smaller meeting room that we call “2 Rock Passage.” In this room there is a couch/lounge area as well as a meeting table of just 4 chairs in front of a big screen and it is used for private client meetings, breakout sessions with our team, and interviews. I find it to be such a useful space for my clients when we discuss strategy and their properties, and it just has a great positive energy.


15. What’s your favourite thing at home?
Probably the kitchen! It is a wonderful space where we love to entertain, and where my wife and I love cooking together as I attempt to be a good Sous Chef for her!


16. Loquat or Bermuda banana?
Loquat’s, and I love locally made loquat jam.


17. St George’s or Somerset?
Somerset! My grandparents on my mother’s (Gibbons) side lived near Somerset Bridge so I have very fond childhood memories of the West End (the best end!).


18. Cricket or football?
Football, but I absolutely love watching both in person and on television. Sometimes my team, Tottenham, makes me wish that perhaps I didn’t watch them at all!


19. What are you reading right now?
Ninja Selling by Larry Kendall. It is a fantastic book that is system based on a philosophy of building relationships, listening to your customers, and helping get them to where they want to be. It is less about selling and more about how to create value for people, which to me is important as I always believe in establishing valuable relationships beyond a transaction.


20. What is your biggest phobia?
Failing at anything 3 times. I think failure is a brilliant thing as we learn through trial and error and it makes us humble, as well as hungry to achieve more. Without taking strategic calculated risks that have great upside, we are unlikely to fail, which is a bad thing in business and in life. Failing once is down to being oblivious and new to the environment of whatever goal we aim to achieve. Failing twice is the real learning curve that is acceptable, but we should then be on the path for more mature, prolonged growth.