What’s your historical NYC and SF connection?
I grew up in Queens, but not the Coming to America Queens you’re thinking of. Eastern Queens is littered with a bunch of dull suburban towns, which is likely why you’ve never heard of any of them. Venture ye not eastward, Long Island City-dweller — unless you’re an Irish-Italian kid with a prescription painkiller addiction, in which case you’ll fit in just swimmingly.

I moved to San Francisco in late 2008, shortly after graduating college in LA, to clear my head after a breakup and to seek out what I thought at the time were My People: other entitled millennials with nerd cred and a drive to build empires. Without doing any research on SF neighborhoods, I had the brilliant notion to live in the Castro, which as you can imagine did wonders for my dating life. The silver lining was that if when any man approached me on the street at 2AM, it was just to tell me that my shoes were sooooo cute and omg where did you get them!?

By 2010, I was living a fairly archetypal SF existence — the startup was taking off, I’d managed to make a couple of good friends — when I was hit with mental illness out of the blue for no rhyme or reason. Within a few days, I found myself back in NY shacked up with Ma and Pa again, after swearing my whole life that I’d never move back to that dreary, cold shithole called NYC. And yet, once I was back on my feet, I saw my surroundings with new eyes, and felt at home for the first time in my life — in the one city that I’d spent my entire childhood trying to flee.

All that said, I’ve been back in SF for over a year now. I’d been feeling pretty meh about my career when a recruiter reached out with a job description seemingly written for me and about me — so I moved again. I spent my first eight months living in SoMa hating the city, and the past six months in the Lower Haight loving it, the moral of the story being don’t ever live in a part of town where even the friggin’ CVS is closed on weekends.

Describe your experience in SF and your experience in NYC.
While I love my life in San Francisco, I’ll always be a stranger in a strange land here. There’s an ethereal optimism in this city that constantly clashes with my ingrained cynicism, and while I’m likely far happier in SF’s mild weather and magical terrain, I’m far more at ease among the grit and grime of New York, even in its most gloomy moments and in the darkest reaches of its underbelly. In other words, I’m torn between the two.

What was the biggest challenge of moving between NYC and SF?
Mustering the inner fortitude to go to the DMV for a new license each time.

How can NYC and SF best engage with each other?

Very, very delicately. NYC is overly abrasive and SF gets offended so damn easily.

Favorite SF secret spot
My entire neighborhood. Sandwiched between several other ‘hoods that try just a little too hard (Haight-Ashbury, The Mission, Pac Heights), Lower Haight is an idyllic enclave that doesn’t cater to any one particular scene and still has much of its history intact, and despite having tons of bars and restaurants has always been overlooked as a destination.

Favorite NYC secret spot
The women’s restroom at Beauty and Essex. I’m not even much of a drinker, but a champagne bar inside of a women’s bathroom feels secretive and esoteric while also following the natural order of the universe — a universe in which many of the most important conversations between women happen inside public restrooms.

If you were not where you are now, what would you be doing?
Working somewhere very similar. I don’t really have hobbies, so I’m a hollow shell of a person when not distracting myself with the nonstop chaos that is tech product management.

Trip Entertainment: what song/album, TV show, podcast, or videos have you been consuming lately?

I’m several years behind the rest of the world and just started watching Breaking Bad! Can’t believe all of y’all in SF already watched this and yet no YC company has even tried to reinvent the meth lab.