Born in Norfolk, Virginia in 1928, Holland inherited his love for the ocean from his father, a member of the Virginia Pilot Association, as well as a first-generation Virginia Beach lifeguard and surfer. When he was nine years old, he caught his first wave on a paddleboard, setting off a lifelong course through surf history.
At the age of 19, Holland followed in his father’s footsteps, working as a Chesapeake Bay harbor pilot — a career he would keep for the next 43 years. But on the side, Holland began dabbling in surf retail. By 1959, he was importing Jacobs Surfboards from California, and selling them out of his garage; in 1960, Holland Surf Shop opened, followed by Smith and Holland Surf Shop, co-founded with Pete Smith in 1962.
As Virginia Beach’s surf community grew, Holland, Smith, Butch Maloney, and a handful of others longed for a taste of competition like the kind they heard was taking place on the West Coast. In 1961, they headed to a loosely organized contest at Long Island’s Gilgo Beach — a year later, they returned for the inaugural East Coast Surfing Championships. The following summer, they helped form the Virginia Beach Surfing Carnival. By 1965, both groups had joined forces and the current East Coast Surfing Championships, held in Virginia Beach, was born.
Holland was also a prolific competitor. He won hundreds of state, regional, and nation-wide amateur surfing contests, including seven United States Surfing Championship titles and 12 East Coast titles. He was the first East Coast surfer to win at the U.S. Open Championships of Surfing. “We were good surfers, so you knew it was bound to happen,” Holland once said of his win on the West Coast. “That it was me is a big deal to me.”
He was also a decorated judge. Through the late ’60s and early ’70s, Holland served as the Eastern Surfing Association’s head judge, and in 1972, he judged the World Championships, held in San Diego, California.
Holland has been called an “enduring and eternally youthful goofyfooter” — and for good reason. Into his 80s, he could be seen out in the water, still in possession of that classic style that made him an icon of the sport. When there weren’t waves, he paddled or competed as a nationally ranked triathlete. “The man was born in 1928,” surf writer Matt Walker said of Holland in 2010. “But everything he says, every action he takes, every wave he rides screams 18 way more than 81.” Holland’s three children were all accomplished competitive surfers.
After being inducted into Greg Noll’s East Coast Surfing Legends Hall of Fame in 1996, he was inducted into the Virginia Sports Hall of Fame in 1997. Holland died in June of 2017 at the age of 88.