What’s your historical San Francisco and New York connection?
I was supposed to move to NYC in 2001. Specifically: I had my last interview for a job – a proposal writer for Sotheby’s – on September 12, 2001. Needless to say, that didn’t happen, and I never ended up making the move in the wake of 9/11. Instead, I stayed in Atlanta, and took a job at Google, which  a few years later gave me the opportunity to move to San Francisco. Even then, I was reticent about making the move; I had just purchased a house and just got a puppy (Lila Belle!) but the allure of a larger city and – frankly – the ability to act like a 21 year-old again, replete with near-nightly costume parties that SF was famous for at that time, lured me in. I spent six fantastic years in San Francisco, working at Google on Google Analytics, leading marketing at Digg and Facebook, before the “itch” to move to NYC resurfaced. I made it happen, a mere ten years after I had originally planned to come.

Describe your experience in NYC.
I am constantly surprised, thrilled and energized by this city. I’ve been here eighteen months, and find something new every day. I struggled with articulating what was the actual draw to finally move here, especially when I was not just content, but happy, in San Francisco, and finally I realized that I wanted to be in a place where I appreciated everything I have here. (I wrote about it a bit here.) Someone said that NYC strips away your creature comforts & then sells them back to you at a price; anyone who has gone through an apartment search can attest to this. For me, though, I love every square foot of my apartment, even the cracked molding and broken floorboards. I love the feeling of camaraderie when everyone is sweating on the subway together on an insanely hot summer day. Or when we coin a random snowstorm the next Snowmaggedon…more than anywhere else I’ve ever lived, in NYC I have the feeling that we’re all in it together.

What was the biggest challenge of moving from SF to NYC?
Leaving my friends. I have made life-long relationships with people I truly consider to be family. Leaving that behind – and coming not for a job, nor for a relationship; instead moving to NYC with the sole impetus being to live in NYC – confused people. Why would I leave when I had things so good already? I’ve been able to maintain these, though, through constant texts (phone calls? The iPhone lets you TALK TO PEOPLE? Who knew?) and apps like Path, not to mention regular visits back, have helped me stay connected with those I love the most.

How can NYC and SF best engage with each other?
With kindness, support & appreciation. I don’t mean that to sound as cheezy as I’m sure it does, but there is this underlying friction between the two cities, especially in the tech scene. You’re dealing with hyper-competitive, brilliant people, who are all working their butts off to make the next amazing thing. Recruiting is a challenge in both cities, with limited resources and an increased need every day. But – as I discussed in this article – we’re not that different. And more endeavors like this newsletter will help both cities collaborate more easily and gain the appreciation for both the differences, and the similarities, between the two.

Favorite SF secret spot
Walking my Dog to the top of Buena Vista Park at 7am on a clear morning. Or, and it’s not a secret at all, Bar Crudo (aka, my favorite restaurant ever.)

Favorite NYC secret spot
My friend Jay’s backyard in Williamsburg. Was one of the first places I spent time at in the city before moving here, and I love how tranquil & secluded it is. Makes me feel like I’m somewhere else entirely.

If you were not at Sailthru, what would you be doing?
My favorite things to do are introducing good people to other good people, and introducing people to undiscovered, amazing music. I’m lucky that in my role here at Sailthru I get to do the former; the latter is a hobby and am getting back into making monthly mixes as I did for years. (You can check out a few here, which I built using this beautiful product called Nubook.) Or, if I suddenly came into a windfall, on the water somewhere, learning to sail while writing that book I’ve been putting off for years.

From the 2905 Miles newsletter: connecting NEW YORK CITY + SAN FRANCISCO