Paul Ruppert and mother Molly Ruppert sit at a booth in Paul’s newest restaurant, Slim's Diner, in Washington. (Mary F. Calvert/For The Washington Post)

The night Ruppert’s restaurant opened in 1993, everyone came — all six of the Ruppert children and loads of family and friends.

The rest of the week, it was basically empty.

The opposite side of that stretch of Seventh Street NW, near Mount Vernon Square, was essentially leveled during the ’68 riots. There was only a parking lot, an emergency men’s shelter, two furniture stores and Ruppert’s.

One evening the sole customers were a couple who broke up over dinner. But Paul Ruppert, then in his early 20s, and mother Molly Ruppert, who were in the kitchen, and sister Christina, their only waitress, were cheerfully undaunted.

The family had always run businesses, starting with the hardware store opened by Paul’s great-grandfather in 1889, and the real estate management company founded by his grandfather in 1936, where Paul and his father, Raymond, still work. There was even a shoestring Christmas tree business started by the second eldest sibling, Tom, and passed on through four other kids that hinged on an old Ford pickup, a tree wholesaler in Pennsylvania and fliers.

Paul had proposed the restaurant a few years before it opened, over several family dinner table conversations. He suggested moving the real estate operations upstairs at the office at 1017 Seventh St. NW, and then tricking out the ground floor as an eatery. His siblings — who at the time ranged in age from late teens to late 20s — were all in school but helped out when they could. Molly began experimenting with recipes for chicken chili, meatloaf and chicken potpie.

In her first review of Ruppert’s, Washington Post food critic Phyllis C. Richman noted the furnishings, “right down to the crockery with a logo from some defunct club, were all bought at auction.” When she asked the waitress — Christina — how the $9.50 steak was, Christina answered, “I don’t know. I don’t get to taste that.”

And yet, “it had a sense of carefulness,” Richman, now retired, recalls, “with a quality of originality.”

After six months, the Rupperts hired chef John Cochran, an alum of Virginia’s Inn at Little Washington, only 28 and brimming with ideas. Shortly after he arrived, the family asked if he wanted to take over running the place. “For us, it was a dream come true,” says Sidra Forman, Cochran’s wife and business partner.

Success came quickly: Food & Wine magazine named Cochran one of the best new chefs in America in 1997. Once Molly and her children put down their aprons, they could have settled for being landlords. Instead, the restaurant gave them confidence in their ideas and in their ability to spot talent. In the following decades, Molly and Paul opened the Warehouse, an avant-garde theater, music and art space, the Warehouse’s cafe and later, after Ruppert’s restaurant closed, the Warehouse Next Door, all on that same block of Seventh Street. Molly’s seemingly unstructured, if-you-can-dream-it, you-can-mount-it approach to art and theater launched many a grateful D.C. artist. Deborah Randall, director of Venus Theatre, calls the 78-year-old“the godmother of art.”

Paul, 49, is known these days for his small retail and culinary empire that includes Room 11 in Columbia Heights, Petworth Citizen, Slim’s Diner and Upshur Street Books.He also initially partnered with two mixologists, brothers Derek Brown and Tom Brown, on the original Passenger and Columbia Room, which made Bon Appétit’s 2010 list of top 10 new cocktail bars in the country. Three years ago, the food blog Eater titled an interview with him “How Paul Ruppert helps make D.C. a cooler place,” reflecting the role both Paul and Molly have come to play in Washington, where prosperity has made the city more dynamic and yet more generic. Few entrepreneurs or arts patrons have cut as distinctive a path through the city as the Rupperts or contributed as much to its quirkiness.

So how did this mother-son duo go from a somewhat quixotic attempt at running a family restaurant to shaping the arts and culinary landscape of the nation’s capital? And why?

Paul Ruppert listens to Katie Presley, assistant manager, during the “WTF NOW?!” event organized by Todd Kliman on Ninth Street NW in December. (Mary F. Calvert/For The Washington Post)

Paul Ruppert was still an undergrad history major at the University of Pennsylvania when he dreamed up the restaurant. “I was interested in cooperating and being a part of something,” he recalls, and “as a middle child, I had less of a need to go out on my own and kind of make a name for myself right when I was getting out of college. Collaboration and cooperation were really important to me.”

It made sense, then, to partner with his mother. In business at least, he and Molly operate as equals. (In public, he refers to her as Molly, not Mom.) Their roles are as distinct as their personalities. Molly is instantly an intimate, quick to establish rapport. She is as interested in interviewing her interviewer as she is in being interviewed. Paul is more careful, less likely to share personal details. Molly collects people. Paul likes to research.

“She was very good with people,” he says, recalling the beginning of the Warehouse. “She would have a conversation with a performance artist, and she would say, ‘This person is going to do a show, so can you figure out how to make it happen?’ ”

Theater companies would set up pop-ups in the cavernous space, once used for the hardware store’s inventory. In 1996, Studio Theatre presented a Caryl Churchill play set in Romania. A Post story noted the worn floorboards and the lack of air conditioning, which was offset by an “urban ‘cool’ that temperature alone cannot measure.” Molly had already created the first incarnation of art spaces, then called Studio 1019. At the annual Art Romp, 50 to 100 artists would mount their work for a single evening, drink and then take it all down again.

Tim Tate, a local glass and mixed-media artist who has shown at Miami’s Art Basel and the Venice Biennale but got his start at the Warehouse, recalls the art ranging from traditional to scatological, even extreme. A man who ate a balloon and then pulled a second balloon from another orifice, an artist who removed his own foreskin onstage. But there were also artists who became major established names — such as painter Scott Brooks, and Tate himself.

In music, too, the space pulsed with vibrancy. Drummer Katy Otto of the band Trophy Wife tells a story of bringing Elaine Brown,former Black Panther Party chair, to a show by Mass Movement of the Moth, a punk band. Brown revealed she was a pianist and was invited onstage to play a set. “It was the kind of thing that could happen because Paul and Molly could trust people to do events and feel like it was our home,” Otto recalls. Paul says that at one point the only venue in the District producing more arts events was the Kennedy Center.

Even as the Warehouse became more established, it didn’t get any more polished. Deborah Randall recalls one day having to kick in one of the bathroom doors to let out an actor trapped inside. She rushed to tell Molly of the rescue. Molly tipped the glass of white wine she was holding in Randall’s direction, looked her in the eye and just said, “Good.”

Paul says their curatorial philosophy boiled down to “We can do this; we have a space.”

“We didn’t know established artists,” Molly says, laughing. “We showed friends and friends of friends.”

But many artists saw something more deliberate. “They did not curate objects or music; they curated people,” Tate says. “If you had a quirky or strong personality you were enabled to do your artwork and show.” Performance artist, poet and Post contributor Holly Bass calls the duo “advocates of the fringe and experimental.”

“They want to support the weird stuff that often can’t find a home in other art spaces,” she says. “They also aren’t interested in the limelight for themselves. I always got the feeling that they find supporting the arts for its own sake and artists deeply satisfying.”

(Mary F. Calvert/For The Washington Post)

Paul and Molly were able to nurture artists and restaurateurs thanks to deep roots in the city and some savvy investing.The Ruppert family arrived in Washington in the 1850s, German Catholic immigrants who became a part of a German-speaking diaspora on Seventh Street NW. Paul’s great-grandfather M. Frank Ruppert opened Ruppert Hardware Store in 1889; it outfitted the capital with hammers and nails until 1987. Paul’s grandfather was born above the shop and later bought properties mostly in the District and Maryland that help sustain his descendants today.

“I’m not a real Ruppert,” Molly demurs, having married Raymond Ruppert in 1959 after graduating from Catholic University. She was a fourth-generation Brookland resident. “I would go to 12th Street for the dime store or the movies, [and] I would know I was safe because I would always meet people who would say, ‘Remember me to your mother, your grandmother.’ It was a very small town.”

Molly and Raymond settled near Chevy Chase Circle and raised Mark, Tom, Elizabeth, Paul, Christina and Nora. When they got older the couple took in foster children. The kids were involved in myriad arts — dance, music and theater.

“I was always encouraged to try new things,” Paul says, “with no expectation to be fantastic at something. If something was worth trying, it was worth trying.” Mark and Christina are in the arts as well: He is creator and executive producer of the 48 Hour Film Project competition; she is its director of operations. The other three are a lawyer, an economist and an engineer.

An uncle ran the hardware store on Seventh Street until construction of the nearby Mount Vernon Square Metro station closed the block for 18 months in 1987. The business died, but the real estate office remained, soon to be reimagined.

The artistic haven the Rupperts created helped save that corner of downtown from both blight and development. “The fact the Rupperts were able to keep a spark going there … was so significant and that they were able to preserve some of those buildings,” says the District’s former director of planning, Ellen McCarthy. “That is a very cool stretch of buildings that add a lot to that block.”

The family’s roots in the local business community go back to M. Frank Ruppert’s hardware store, opened in 1889. (Courtesy of the Ruppert family )

But with the opening of the Walter E. Washington Convention Center in 2003 and the ensuing rapid development downtown, property taxes eventually soared by 500 percent, making their shoestring margins untenable. Paul and Molly reluctantly looked to sell. Then the economy tanked. Instead of selling immediately, Paul started a project that he had been mulling with star bartenders Derek and Tom Brown, which became the Passenger and Columbia Room, sibling bars nestled like Russian dolls. “People noticed it right away,” says Derek Brown, now owner of Eat the Rich, Mockingbird Hill and Southern Efficiency in Shaw. “Paul was instrumental — not just as a business partner but also as a mentor.”

In 2013, the family finally sold the properties on Seventh Street and one on New York Avenue to developer Douglas Jemal and split the profits among a large number of family members. Paul, who by then had opened Room 11, a tiny wine bar and small-plates restaurant, with Nick Pimentel, Dan Searing and Ben Gilligan, invested his share in various projects in Petworth. Molly returned to school to earn a certificate in life coaching (she already had a master’s in counseling). But leaving Seventh Street after 124 years was bittersweet. Despite reaping a significant windfall, Molly says, it still felt as if they had been “wrenched away from what was a kind of home here.”

Assistant manager Katie Presley and Molly Ruppert on Ninth Street NW in December. (Mary F. Calvert/For The Washington Post)

On a dreary December night, the enormous picture windows of Slim’s Diner in Petworth are decorated with a witty mix of wintry cheer and a hint of cheek with a seasonal sculpture by artist David Mordini. Around the back and up three flights of stairs, 40-odd people sit in a room with rough-hewn wood floors and whitewashed drywall for a panel called “WTF Now?!” featuring economist Tyler Cowen, poet Sarah Browning, Slate writer Jamelle Bouie and philosopher Firmin De- Brabander. Writer Todd Kliman is moderating. Every seat is filled; the event is sold out.

After brief opening remarks, Paul steps aside and hangs in the background with Molly. He had been eyeing Petworth for years before he started opening restaurants along Upshur Street NW, just east of Georgia Avenue. He wanted his new ventures to be welcoming to both new and longtime residents, so he did things like put out a call for what kinds of potatoes to serve at Slim’s — and got 800 responses. Kliman’s “WTF Now?!” discussion series is more political than other recent projects. But Paul says it is part of a continuum with the Warehouse.

After the panel wraps, Paul stays behind while Molly meanders over to Petworth Citizen, chats with the staff and settles in with a Manhattan. She talks about curating shows in Anacostia and coaching artists. It is easy to see how she works and how she charms. Again and again she turns the conversation back to the reporter and away from herself.

Turn off that recorder, she nods toward the device, so we can really talk.

Sarah Wildman is the author of “Paper Love: Searching for the Girl My Grandfather Left Behind.”

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