Take Five with Jake Dobkin ’98

Jake Dobkin ’98 is the publisher of Gothamist. He lives in Brooklyn with his wife, Karen Leskly Dobkin ’98, and their two children. Dobkin recently published Ask a Native New Yorker, a book of essays about life in New York City.


What were you like when you arrived at Columbia?

Between my native Brooklyn attitude, and my insecurity about being a transfer student, I was pretty desperate to prove myself. That led to a lot of loud-mouthing in Core classes, and some colorful extracurriculars — doing graffiti with the Prentis Hall art kids, exploring the tunnels under campus late at night and at least one ridiculous bar brawl. Somehow I kept my grades up, but there was more than one trip to the Dean’s Office for various infractions, including, memorably, the time I spent $500 of Woodbridge’s dorm entertainment budget on pudding cups as a prank.

What do you remember about your first-year living situation?

I didn’t arrive until sophomore year, and after a disastrous roommate situation freshman year at my first school, SUNY Binghamton, I decided I would do best in a single. Unfortunately, transfer students had the last shot at rooms, and I ended up in a double at one end of the eighth floor of Wien. Interestingly, the other transfer assigned to it had failed to matriculate, so for a week or two I was living there alone, and it was paradise — twice the size of a normal room, with a sink, and two exposures. But then the housing office started sending prospective roommates to move in. It took a lot of creativity to hold them off for the entire year, including, I believe, moving most of the furniture to the basement. I think that eventually led to another trip to see the dean!

What class do you most remember and why?

I was pre-med, and despite everything else, was quite dedicated to the classes and lab work, and the internship at St. Luke’s that went along with it. I particularly liked all the chemistry classes, which led to a job for a year after graduation as a chemistry teacher at Stuyvesant H.S., which was a whole other crazy adventure. Outside the sciences, I had a minor in English lit, which years later came in handy when I went into journalism and had to do a lot of writing. The class I remember most was Alfred MacAdam’s “Latin American Literature,” which introduced me to Borges and Garcia-Marquez and many other writers who remain favorites.

Did you have a favorite spot on campus, and what did you like about it?

I had a ton of semi-secret spots — the roof of the library, distant corners of the stacks, those two platforms at the edge of the Low Steps, the observation deck of Riverside Church (where I once almost got trapped for an entire weekend), plus some others I can’t name. The campus was like a wonderland that I could never fully explore.

What, if anything, about your College experience would you do over?

I probably wouldn’t have done that naked art show, or sweated that B+ in organic chemistry so much. But on the whole it was a great experience that introduced me to my wife, my business partner, many of my closest friends and most of the hobbies and passions I still enjoy today. I’d give it five out of five stars!