My journey in the world of bars started long before I drank my first beer. I grew up in Cleveland Park, a quiet Washington DC neighborhood where we were given room to roam. My best friend Daniel (front) and I were in entrepreneurial lockstep as we delivered newspapers, raked leaves, shoveled snow, and published our own rag, The Macomb Street Journal. All this early hustle led me to buy my first car when I was 15, a 1967 VW Karman Ghia, for $125. I was a year short of my driver’s license, but why let technicalities get in the way? Not one to limit my rule stretching, at 15, I also drank my first bar-beers at Gallagher’s Pub (now Nanny O’Brien’s), a Cleveland Park bar I now own with partners. By the time I was a junior at Wilson High School, I had a morning paper route, delivering 350 Washington Posts 365 days a year, worked at several gas stations, tore tickets at the Georgetown Theater, and started painting houses. I was willing to try anything.
Along the way, a four-year stint as a soprano in the Washington Cathedral Choir provided me with an excellent business foundation. My mother was kind enough to save this reprimand for my having operated an “armaments business” on Cathedral grounds. It is one of my prized possessions. “Dawson, this will be on your permanent record!” were words I heard more than once from teachers; I still hope to find that permanent record somewhere.
My first restaurant job was during my junior year in high school, with my best friend Daniel at Phineas Prime Rib, a Marriot chain restaurant located on Wisconsin Ave, near VanNess St in DC. This was an eye-opening introduction to what happens when management doesn’t pay attention, and the staff runs wild. I remember leaving after long shifts with steaks, popovers, dessert, and food that my stoned housemates welcomed. At Phineas, I started as a dishwasher, graduated to busboy, and then became the beer & wine bartender. Danger, Will Rogers! For a few years after high school, I worked as a motorcycle messenger and traveled all over the US and the world whenever I had a few bucks to burn.
Next up was the University of Massachusetts, where I worked in the Student Union Carpenters shop and studied history. I spent countless hours in the Amherst Public Library and stumbled on a book that captivated me— Rolling Homes by Jane Lidz. The book was filled with buses and vans that had been converted into homes. Why not build my own? My friends thought I was crazy, but that never stopped me from trying something new. I bought an old step van from a wood stove shop where I briefly worked and got to work designing my new home. The plan was to live in the university’s parking lot and eventually head off to see America. Unfortunately, engine seizure ended this adventure before it began, but the process of dreaming and building something crazy was in my blood.
I never graduated from UMass, and I remember little from the classroom, but the life lessons were extraordinary. From working as a carpenter to bartending at the Iron Horse Music Hall in Northampton, I discovered the loose pieces of what would eventually become my career building and opening bars. Back in DC, I started a small contracting company with a friend and mentor, Mike Millan, and we laughed as much as we built.
My life of random choices, often made with little thought but loads of curiosity, led me nicely to 1992 when my cousin married a pool shark, and I decided to open a pool hall, once again, diving into something I knew nothing about but was willing to try. My friend Brian Harrison, a DC bartending legend, and I describe our similar histories in this way: “Dumb enough to try, too stupid to quit.”