Tristan & Kieran O’Grady: Brothers Born in U.K. feel Hilton Head is the best place in the world

ogradybroBrothers born in U.K. feel Hilton Head is the best place in the world

Tristan & Kieran O’Grady,
United Kingdom

If you’re looking for a poster child for the notion that America is the land of opportunity, and Hilton Head Island offers more fertile soil than most for the growth of the American Dream, you could do far worse than Tristan O’Grady.

Born in the U.K. and raised in the extremely British-sounding Buckinghamshire, O’Grady spent his formative years traveling from place to place. His father, a resort developer, kept his family constantly on the move, and before he was rown the younger O’Grady had called England, Australia and South Africa home.

His wandering days ended when his father’s business in the U.S. led him to a golf vacation here on the island.

“For some reason he ended up on Hilton Head Island in the late ’80s,” said O’Grady. “He fell in love with it. He appreciated how it was being developed and the sense of a resort community that was designed to be a place to live and to vacation.”

And so, at 17, O’Grady made his last emigration. The young man who had seen the world had found his forever home.

“Looking back, it was a wonderful time. I instantly made a lot of friends who I’m still friendly with now,” said O’Grady.

Time away at college in Atlanta, and a brief return to the U.K., couldn’t silence the siren song of Hilton Head Island, a place where O’Grady had already established such deep roots. He’ll tell you about his time tending bar at “the infamous Batty Bats” or the summer spent helping in the construction of Hilton Head Christian Academy, but what he’s really telling you about is how Hilton Head has wrapped itself around him and vice versa.

And of course, there was the not-small-matter of meeting his wife Stacey, an oncologist at Hilton Head Hospital, shortly after college and falling in love. They now have four children.

But here it’s not enough to discuss just his roots. America is the land of opportunity, and O’Grady pursued them with zeal. His experience behind the bar led him to open Moneypenny’s (a moment of silence, please, for many a bad decision we all made at the old after-hours bar). A year later, the iconic island establishment Big Bamboo went on the auction block, and O’Grady jumped at the chance.

“We were lucky with Big Bamboo. It went out of business and my dad was a business broker at the time,” said O’Grady. “My dad always encouraged us to pursue our dreams, so when these opportunities presented themselves he helped out.”

O’Grady and his brother Kieran took over the Big Bamboo in 2000, and raised its profile from “that bar with the WWII stuff everywhere,” to a place that not only draws in visitors by the score but gives locals a first-rate watering hole, lunch spot and live music venue.

And while the life of an island nightspot operator proved too at odds with the life of a loving father of four, O’Grady launched a successful real estate career while still running Bamboo with his brother. A realtor has to be able to really sell the island, and O’Grady has a killer elevator pitch.

“When I sell real estate, I say after living on other continents, Hilton Head Island offers a better lifestyle and place to live than anywhere else in the world,” he said. “You can find bluer water or a better bar scene or a sandier beach, but when you put it all together, Hilton Head comes out on top.”

And apparently it’s not a bad place to chase down the American Dream, either.