How Steve “Monty” Montgomery, Renowned Restaurateur, Rolls

The Starboard owner works hard and plays hard, and gives back along the way.

Steve Montgomery might have been born in Washington, D.C., but in his heart, he’s always been a coastal Delawarean.

“I spent every single full summer of my life in Rehoboth Beach—along with most weekends year round,” he says. “I always wanted to be a beach kid.”

In many respects, he got his wish. Today, he’s the co-owner of four beach-area restaurants, including the landmark Starboard in Dewey Beach.

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Any Sussex Countian worth his or her salt will tell you that does not a true resident make. But if anyone gets a pass, it would be “Monty,” as he’s been called since college. Not only has he contributed to the local economy, he has also given back to his adopted home.

“Monty is a pillar of the Delaware community,” says Scott Kammerer, CEO and president of SoDel Concepts, a hospitality group with eight beach area restaurants. “He’s a great restaurateur that we can all look up to as a leader and a visionary here on the Culinary Coast.”

Local food writer Bob Yesbek would agree. “I have the utmost respect for Monty,” says Yesbek, the man behind the popular, which covers the dining scene. “Everything he touches turns to gold, and I believe that stems from the way he treats the people around him. He shares that quality with the late Matt Haley, who also built a successful enterprise by paying attention to everyone in his employ, from the dishwashers to upper-level management and everyone in between.” 

Monty started his own career on the bottom rung—at the tender age of 7. He is a firm believer in the Golden Rule: Do unto others as you would have them do unto you. “I just do my very best to treat many people well, and I hope in return they respect me,” he says.

The youngest child of Charlie and Barbara Montgomery, Monty was also the only son. “They save the best for last, right?” he jokes. Apparently, his older sisters didn’t think so. “They tortured me growing up.” 

His father worked in commercial real estate and property management, and his mother initially stayed at home in Arlington, Va., with the kids. In the summer, Barbara and the children moved to the Henlopen Acres home that Monty’s grandfather, Miles Montgomery, built in the 1950s. The house had seven bedrooms, enough to accommodate all the children, but no telephone. (Montgomery’s father came on weekends.) His grandfather told him that one day, he would own the house. “I believed him at a young age and couldn’t wait to declare Rehoboth Beach as my home.”

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When he was 7, Monty went to work for Dick Catts of Catts Beach Service, which rented umbrellas and chairs on the beach. The job, like summers in Rehoboth, became a tradition. Come September, his beach friends headed back to Rehoboth Beach Elementary School, and he went back to Virginia.

When Monty was 18, he got a nighttime job at The Starboard in Dewey Beach, then owned by the Hearn family. The local watering hole dates to 1960, when it was named Duke Duggan’s Last Resort Bar and the specialty was spaghetti and meatballs. Monty started as a doorman and a bar back.

He remembers well the first night, in 1987, that he was given the opportunity to tend bar near the front door. Because he was shy, bar manager Claire Walsh told Monty to belt a few back at The Bottle & Cork to “loosen up a bit” so he could talk up the customers. “I remember her saying, ‘Be fun but not obnoxious.’” She let him know that Chip Hearn would notice whether the register was ringing and if patrons were leaving Monty’s bar with drinks. “It worked out perfectly,” he says. “I stayed on that same bar for the next decade, every weekend.”

Monty pursued a business degree at Randolph-Macon College in Ashland, Va., where he made lifelong friends. “RMC will always hold a special place in my heart,” he says, though he wishes he’d paid more attention to the business classes he slept through, he jokes. After graduating, he spent several years at the beach.

“In reality, I did not want to grow up and wanted my summer job to continue for life,” he says. In some respects, that is what eventually happened. Until then, he spent seven years working at the family commercial real estate business, Koones and Montgomery, in Washington, D.C., which his grandfather founded in 1946. On weekends, he kept his bartending skills sharp at The Bottom Line in Washington, D.C., owned by Jim Weisgerber and Dick Heidenberger.

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Having been involved in The Starboard for 12 years, Monty knew when, in 1999, the Hearns wanted to sell. He also knew he was the guy to buy it. “But I had no clue how to make that happen,” says Monty, then 29. He turned to Weisgerber and Heidenberger, who helped him put together the deal, raise capital and borrow money. 

“I was terrified to tell my dad that I was partnering with two folks to buy The Starboard,” he says. “When I told him, he was more supportive than I could ever have imagined. He knew it was an opportunity, and I knew I partnered with successful guys.” In 2000, Monty and the two partners split ownership of The Bottom Line with JR Mosbrucker.

In 2004, Monty, Weisgerber and Heidenberger, along with Kevin Roberts, opened Bethany Blues in Bethany Beach. A second location followed in Lewes in 2009.

Monty and his original partners, along with Steve Roop, have owned Portside Tavern in Baltimore since 2005. With Weisgerber and Eric Sugrue of Big Fish Grill fame, he owns Nick’s Fish House, also in Baltimore. Last year, he and his Bethany Blues partners opened 99 Sea Level Restaurant & Raw Bar in the new Marriott in Bethany Beach. And soon to come is Starboard Raw, a 48-seat raw bar on Coastal Highway in Dewey.

With so many restaurants to run, time is an issue. The partners cover for each other, and at least one of them is in a restaurant on most days. Each, however, has a favorite, and for Monty, that is The Starboard. 

When he started working there, it was primarily a locals’ bar. Then it became a hangout for D.C., Baltimore, Philly and Wilmington people on vacation. Now, he says, it’s a locals’ favorite that still draws tourists seven days a week in the season. Monty’s goal is to keep the action going from breakfast through last call. It thrills him to see people nursing hangovers eating breakfast near families with small kids. He feeds on the diversity.

Monty says there is room for everyone—including kids—in Dewey, “an amazing, small and cozy resort with a big ego and reputation.” He was instrumental in bringing movies and bonfires to the beach. The Starboard sponsored Radio Disney when it came to town, and there’s now a kids’ version of the Running of the Bull. (The adult version, during which people run after two people in a bull costume, is entering its 20th year.)

Since the day he and his partners purchased The Starboard, he has supported the Dewey lifeguards and police, “the backbone of this town,” he says. The Dewey Winter Gala has raised nearly $100,000 for both. The gala also benefits the Dewey Business Partnership, which he has been president of since it started in 2011. Other Starboard events have raised more than $50,000 for the Rehoboth Beach-Dewey Beach Fire Department.

This year, he’s also president of the Delaware Restaurant Association’s board.  

“Monty is what all boards aspire to have today,” says Carrie Leishman, president and CEO of the association. “He is a passionate advocate for his industry, and he’s earned the respect of his peers by getting things done and never apologizing for having fun along the way.”

Of all his business and philanthropic activities, Dewey Goes Pink, a 5K race and party that he coordinates with gym buddy Adam Howard, is the closest to his heart. His mother passed away in 2010, after a 25-year battle with breast cancer. Given he has two daughters with Dee Dee, his wife of 12 years, and three sisters, he’s concerned that another of his loved ones will face the disease. Over the past five years, the event has raised $250,000 for the Delaware Breast Cancer Coalition.

Leishman calls Monty “a collector of people. He has a unique ability to convince everyone that they are his best friend and he knows everyone,” she says. Monty says that he’d far rather give than receive. It’s one of the reasons he loves what he does. 

A proponent of the work-hard-play-hard approach to life, he also loves to go on vacations with his wife and daughters, who are 9 and 5, to “eat, drink and laugh.” “I just love my little girls and want them to be part of my work and my free time.”

His daughters are now students at Rehoboth Elementary School, where he once longed to go. Chip Hearn’s son now works for Monty at The Starboard, as does Walsh’s daughter. “I could not be happier,” says Monty, “to see how life comes full circle.”

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