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all photos: Jeff Martin, interview by: Eden Raskin Jenkins

Paul Ruppert is the man behind the neighborhood, pulling the strings between fantastic local spots that you might not even know are connected (hence his no repeats rule). Paul is behind the original Columbia Room, The Passenger, Room 11, Petworth Citizen, Crane & Turtle (rip), Upshur Street Books and the soon to be opened Slim’s Diner. While this list alone is impressive, Paul has many more notches on his belt and doesn’t plan on slowing down anytime soon. Yes, the subject of the latest DC Dream Jobs feature is obviously very accomplished, but he is also deeply humble, hardworking, and has an uncanny (and enviable) ability to see into the future and just know what a neighborhood needs and can support, cue Upshur Street in Petworth. Each step of the way is admittedly a learning process for Paul and his team, but man what I wouldn’t give for his crystal ball.

What do you consider your first real job?

I had this feeling that restaurants might be in my future, so I worked with a lot of different restaurants. I would work there for six months and move on to a different one. I basically spent a couple years just doing different jobs and various things.

So, what was your favorite of the restaurant jobs?

One job in Philadelphia, it was like a nicer cafeteria. The cooking line was right up front, so you interacted with guests as they were coming down the line to order stuff, and some things you would just serve them from steam trays. Other stuff, like a burger or something like that, you’d have to call off to a short order cook who was basically right behind you. So that was a lot of fun, because you were in the kitchen, but got to interact with customers at the same time. There was a lot of good energy there.

What brought you back to D.C.?

I graduated from school with a history degree and I didn’t know what I wanted to do with my life. So I convinced my parents that we should open up a restaurant and that’s what brought me back. We opened our first restaurant in ’92, which was called Ruppert’s Restaurant and was on 7th Street.

What were you doing for the restaurant and who was doing it with you?

My mother was my partner. It was an American home style kitchen so it was food your grandmother would make. My sister, Christina was out front and it was very lean that first year. We didn’t have very many customers at all. We did get a review from Phyllis Richmond and it was a pretty good review… but it wasn’t a great review. At that time in the 90s hardly anyone was living downtown so after about a year we realized that we needed to do a better job of telling our story and getting the word out that we were actually there. We couldn’t do that because we were in the kitchen cooking, so we hired John Cochran as the chef. He turned out to be this fantastic chef and he took the restaurant from American home style and gradually made it to American cuisine but of the highest quality. Eventually we actually sold the restaurant to him. He was a real genius when it came to cooking.

Why did you sell the restaurant to him?

I was interested in going back to school because I was still interested in academics and potentially becoming a history professor. So at the point where John was working for us and starting to make changes in the kitchen, we could tell that he was ready for his own restaurant and I was ready after a couple of years to go back to school. So those things worked well in tandem and we just decided to kind of make a leap. I make a lot of leaps in my life and in my work. Sometimes they work out and sometimes they don’t, and this one just luckily worked out.

So you went back to school for history?

Yes, it was a Masters Degree in Irish Studies and I did that at Catholic University. Then from there I had the option to go on to get my PhD or I was offered the opportunity to run a small Irish-American museum in New York. So I decided to do that and my wife and I moved to NYC and we ended up there for five years.

How old were you?

28, I think about to be 29. So I got the job and then moved to NY and stayed there for six months then got another job. That was a disaster so I stayed at home with the kids and my wife went to work. That was a big experience.

Was it scary to quit your job and give up an income with children?

Everything’s scary. I’m an optimist and I love to do new things and am very quick to do new things and to take on new challenges and opportunities but everything is scary.

What made you move back to D.C.?

So there are two things that brought us back. One our apartment in Manhattan was starting to feel cramped. And two, while in NY, I was managing an art space, which was a theater and gallery on 7th street in D.C. so the opportunity to come back to DC and go back to what was still going on on 7th street was exciting. So we kind of made this decision from a standard of living standpoint, and the opportunity to do something interesting and meaningful with the building that my family owned.

So then you came back to D.C.…

We basically took what we had been doing on 7th street and we further developed it.  The restaurant was still there, but we weren’t managing it or doing anything with it. We started to develop other things. We owned three buildings on that street, and we turned one into an art gallery, the second into the Warehouse Theater. And then gradually we added the Warehouse Café, later that would become the Passenger. Then we added a second space, we added more gallery space, we added a music venue, and we did all of this during the first decade of the 2000s. In 2006, we had more events and performances than any other venue in D.C., other than the Kennedy Center. We had over 600 nights of music or film or theater or what have you. It was a really vibrant space for the arts in DC.

I did that for a number of years and then we were going to sell the buildings around 2007.  We started to wind down what we were doing with the theater and everything. We were prepared to sell, and we had a contract to sell, and the economy went down the toilet and the contract disappeared. I had been looking for my next project and had been talking to Derek Brown and Tom Brown, so we just decided to do the Passenger and Columbia Room in that building. So that’s how the Columbia room came to be in our spaces on 7th street.

How much of a hand did you have in the concept and the opening?

I was really kind of centrally involved in the opening of it, since I was experienced in that and had done it a couple of times already. Derek and Tom both had their visions for the Passenger and Columbia Room but they weren’t fully defined. That’s something I’m really good at is asking questions and prodding people and saying “are you sure you really want to do it that way?” “Why not do it this way?” So I was central to that process but not in a public way and not in a driving the car way. We met everyday for a period of a couple of months. We opened Columbia Room in February, and I’m also kind of handy in carpentry so again I was very helpful in guiding the physical vision. In fact, we had to be opened by February 14th, which was Valentine’s Day and we had a big huge snowstorm, so I took my air mattress and slept there for three nights and worked 18 hour days finishing the Columbia Room enough that we could have guests come in on February 14th.

Have you found that you’ve been missing something crucial that you’ve had to adjust quickly?

When we opened the Passenger, it was going to be a punk rock wine bar. That’s what Tom and Derek wanted, a punk rock wine bar. All the press was saying that Tom and Derek made delicious cocktails, but that was a secondary thing for us. Within two months we had shrunk our wine down to just a few selections and we were going full steam with the cocktails.

What are the biggest lessons you learned from opening restaurants?

Well, of course, the first one is that everything takes longer than you expect. And that’s been true for about every restaurant that I’ve done. I would say that I’ve learned that there have been things that I’ve had a natural ability for and certain things I did not. That was both eye opening and humbling because when you’re 22 you think you can do anything. And it very quickly became apparent that I was good at some things and not so good at other things. I would say those are the things.

So what were some of the things that you had to let go of and what were some of the things that you knew you had to take on as your own?

For me the front of house was difficult. Having that interaction was difficult with customers because at times their expectations were not fair. And as a 22 year old, I was not equipped to do a good job for the customers coming in. Since then I’ve learned quite a bit and a lot of that has been working with people like Derek Brown, Tom Brown, Dan Searing and Elizabeth Parker and just watching them with customers. Now I’m a lot older so I’ve been able to learn by watching people that are good at this type of thing.

And then what are your strong suits? What did you really feel passionate about?

For me it was putting together a project. Recognizing what the business should be for that particular space and neighborhood at that particular time. I think that’s one of my strong suits. At the time of my first restaurant, the Convention Center had not been built across the street for instance, it was a big huge parking lot and on the corner of it was a homeless shelter and so lots of people came and thought it was the craziest thing in the world to open up a restaurant across the street from a homeless shelter. I think that’s something I’m good at–my ability to see down the line, into the future and have a good idea of how a neighborhood or a street may change over time and to be early in on that change.

That’s an important skill to have in a developing city. Obviously Petworth is an emerging exciting neighborhood. So how did you choose Petworth?

We were ready for our next project. I love D.C. and I love the neighborhoods in D.C. I’m out and about quite a bit, going to art shows, theater performances, other restaurants and bars. And I love learning about them and the history of them, and what makes them tick. So when we were looking for our other project, Petworth was one of the neighborhoods that was on my radar. Kera Carpenter had opened Domku 5, seven years before, and I talked to her a number of times and she was encouraging about Petworth. When we were looking, the Petworth Citizen space and the Crane & Turtle space became available at the same time so I could picture something that combined the two spaces. So have a neighborhood restaurant and bar in Petworth Citizen and then have something that’s a little more elevated, basically fine dining meets the neighborhood in Crane & Turtle. So that’s kind of how that happened.

Did you think having two spaces created more of a street?

So that’s the idea. You don’t necessarily want to open your restaurant where there are a bunch of other restaurants, because that could be a challenge, but three, four, five restaurants can be a real benefit. And we see that all the time where people come to Crane & Turtle or they come to Petworth Citizen for a drink, and now we’ve opened a bookstore, so people will browse the bookstore or go to a reading in the bookstore then come to Petworth Citizen for a bite to eat. We’re very happy to have Twisted Horn on the block now…the cocktails are delicious.  So that’s an important part of our calculation, as well. And I could see that there were changes happening in Petworth and that we could get in early on those changes and that we could really make our imprint.

How do you make sure to successfully integrate your businesses into the neighborhood?

You have to listen, and that’s something that I try to do, especially when you’re doing a project. That’s why I get out there and talk to a lot of people. For instance, with the diner we did an online survey where over 800 people answered a series of questions. I wanted to know what people thought.

I think that’s such a great approach and allows you to listen to your customers and neighborhood. You’re working with your customers and that leads to success.

It’s interesting also in that with Crane & Turtle we wanted it to be more neighborhood focused, but the quality of the food and drink meant that people were coming from further afield so we had to do reservations and it’s more of a destination. It’s still in a neighborhood setting, but it’s also a destination. So we open and then we tweak. And some we tweak more than others.

What inspired you to open each of your business ventures and what’s a common thread between them?

So there are lots of common things between them. One is that we’re friendly and welcoming, that’s first and foremost. Two is that quality is important to us but it’s not luxurious quality, it’s affordable quality. And the third is the craft component. Four is that we set parameters and then we hire people who we hope can operate within those parameters. And we give them a set of expectations but we also give them a set of responsibilities to fill in the blanks and fill in the spaces. So it’s not rigid what we do, it’s not top down by any means, it’s bottom up. At the top we kind of create the structure, but we let the details percolate up from both the people working in the space and our customers. Our customers really drive what we do and we don’t know that completely until we open. And then the other thing is we don’t repeat. At least so far we haven’t repeated.

Who is the person or who are the people who have inspired you the most?

Dan Searing and Elizabeth Parker for their sense of hospitality. I learned so much from them and that’s one of the great things about doing this as a slightly older person–now I recognize that I can actually learn things from people. Tom Brown, I really admire because he’s someone who is both really knowledgeable but also truly authentic to himself. He doesn’t pretend to be something that he’s not. He is who he is. Derek, I’ve learned a ton from. What I admire about Derek is his ability to connect to almost every person that he meets in a way that feels real. I think that’s one of his true magical abilities, to make anyone he talks to think that they are his friend. So that’s something that I don’t have naturally, but I’m a true believer that you can learn things and you can change the way you approach people or the way you do things.

What is the hardest part about having your own business and the most rewarding part?

The hardest part is the buck stops with me. That’s by far the most difficult, that I can’t throw my hands in the air and say “help someone else solve this for me.” The most rewarding part, I love it on a Friday or Saturday when I come into one of my restaurants and everything is working and there’s tons of people and there’s a fantastic energy in the room and you can just tell that the front of house and back of house team are both on top of their game and it’s like when everything comes together, I don’t want to say it’s magical, but it’s magical.

What advice would you tell your younger self?

I would tell myself, both my younger self and my self right now to be more disciplined. I think that’s something that I have not conquered. The other advice is talk to as many people as you can. The more contacts you make, the more successful you’ll be, and that’s coming from someone who couldn’t call up a girl in high school, couldn’t pick up a phone and make that phone call.

Where do you see yourself in one year, five years, and ten years?

So one year, I mean we’ve got the diner opening. And I think that the next year is about opening the diner and then solidifying what we’re doing at our other places. In five years and ten years I’d like to be more involved in the arts. So I’ve kind of swung away from that with the closing of the warehouse theater and the gallery, but that is an important part of what I do. So for instance right now I’m on the Board of the Anacostia play house, and what I’d like to do is be more active in the arts and perhaps create more space for artists to offer and present their art. So that’s my kind of longer term goal to get back into that world.