Sailing into the Unknown

As someone who seeks out new experiences, Herb Ressing, GWSB MBA ’68, was excited to make his way to Washington via a one-semester undergraduate exchange program at American University. But the MBA program at GW’s School of Business led him to put down roots…for a time.

Ressing quickly made connections and began working for Senator Charles “Chuck” Percy – just the beginning of his life as a Washingtonian. A mentor at American encouraged Ressing to get a master’s degree, and he soon enrolled in GW’s evening MBA program.

“The reputation was outstanding,” Ressing remembers.

Ressing settled in Capitol Hill, where he raised a family and built his expertise in government. Over the next two decades, he supported a President’s Commission, worked for the Federal Trade Commission, served as a regional director for the Republican National Committee, and was a lobbyist for the Synthetic Fuels Corporation. He was also an early member of the Cogswell Society. Founded in the 70s, the group hosts monthly gatherings to toast “to temperance,” a tongue-in-cheek nod to Henry Cogswell’s Temperance Fountain (in northwest D.C.) and its teetoalsim origins.

Successful as he was, by the early 90s, Ressing – a traveler at heart – longed for something different. And he had an inkling of what might come next.

A few years earlier, a friend convinced Ressing to take a captained charter to the Virgin Islands, after an injury derailed their plans for a ski trip. Reluctant at first, Ressing soon found himself captivated by life on the water – and a bit starstruck. On the way to the islands, Ressing’s group happened to dock next to legendary journalist Walter Cronkite and his custom Westsail yacht.

“I thought to myself, if I ever had a boat like that, I would have died and gone to heaven,” Ressing says.

The trip turned out to be a game-changer. Ressing came back to D.C., purchased an old boat to restore, and learned to sail. He earned his captain’s license and began to take charter jobs on the Chesapeake Bay. It soon became clear that his new calling was in maritime life.

The universe agreed. As luck would have it, a friend with the Annapolis Sailing Academy’s boat donation program told Ressing they had a yacht that might be of interest to him. The former owner? Walter Cronkite. With the winning bid, the boat that started it all became Ressing’s new home. (He was actually able to relay the tale to Cronkite, during another chance meeting on the docks.)

With “The Chesapeake” ready, Ressing assembled a crew and headed south on the Intercoastal Waterway.

He docked in Ft. Lauderdale, Florida where “maritime is the lifeblood.” Soon, he was not only chartering, but also brokering yachts and branching off into other part of the business, including business development for local marinas.

“My job in the marine industry was to serve as a marketing and sales representative for outreach programs, and the background that GW gave me was very, very helpful,” Ressing says. “The MBA opened more doors that the average person would deserve…the fact that it was from GW was even more helpful.”

While Ressing was able to reinvent himself on the seas, the journey has not been without challenges. Once, while chartering a group of teenage boys to Key Largo, Ressing encountered a terrible storm, after the boys’ antics got them kicked out of the marina at midnight. High winds snapped the boat’s bowsprit – which helps hold up the mast – and, as Ressing says, “the reality of sailing became really real.”

Unpredictability, however, is what first inspired Ressing to change his life. And it still inspires him today, on the water, and beyond – he and his wife recently visited Africa during a three-week safari. For Ressing, sailing is not just a passion, but also a way to welcome the unknown.

“You have to try new things,” he explains. “Sailing has given me the chance meet so many interesting people and explore different cultures. It’s an adventure every time you leave the dock.”

-Melissa Nyman

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