What’s your historical San Francisco and New York connection?I was born in NYC a few blocks from my current home. I first visited SF when I was looking at colleges, but concluded that Stanford was too sunny and beautiful – if I went there, I’d just play frisbee all the time and never learn anything. I moved to SF in 2012 after eight years of living all over the place – Paris; Boston; London; Washington DC; Madrid; Dongguan, China; and Istanbul. I’m back in New York now, but still make it to SF for at least a week every two months.

Describe your experience in SF and your experience in NYC.
When I moved to SF, I’d been living in the Middle East for three years. I had major reverse culture shock. There were certain things that were nice about being back in America: I loved that journalists weren’t thrown in jail, that I could get strawberries whenever I wanted not just when they were in season, etc. But I also noticed America has its own problems: entrenched economic differences, racial segregation, and all sorts of weirdness in the way that men and women interact. I found SF especially odd, with its tech elite stepping over passed-out homeless people on the way to get their $8 toasts. I moved to New York after six months, and have lived there ever since. But I’ve ended up back in SF with more and more frequency, drawn to the ridiculousness of the city. It has many flaws, but it nurtures a kind of audacious thinking that I find addictive. Plus I’ve found it much easier to raise capital for my company, Hitlist, in the Bay Area.

What was the biggest challenge of moving between NYC and SF?
I haven’t found it challenging. I get my tickets via Hitlist, which send me an alert whenever flights between the two cities drop below $300. I keep pretty detailed lists of who I want to see when I’m in either place, and I try and make it possible to catch up with as many people as often as possible.

How can NYC and SF best engage with each other?
Most San Franciscans seem peculiarly uninterested in the world beyond the Bay Area (unless you count Black Rock City for a week in August/September). I’d like to see more San Francisco residents act like New Yorkers, who will say that their city is the best in the world, but they tend to have a bit more reason to say so.

Favorite SF secret spot
I like Bluxome St. Winery – it’s not quite a secret but relatively tucked away in SOMA. You can split a bottle of wine with a few friends for much less than buying individual drinks, and the space has a nice airy feel.

Favorite NYC secret spot
Burp Castle, 41 E 7th St.  Bartenders periodically ‘shush’ the patrons so it never gets too loud. I love coming here for a quiet catch up with close friends over obscure Belgian beers.

If you were not where you are now, what would you be doing?
Trying to think of a better way to get everyone in the world to travel more.

Trip Entertainment: what song/album, TV show, podcast, or videos have you been consuming lately?
The Stuttgart Piano Trio’s 1988 recording of Schubert’s Piano Trios in E Flat Major.