Nate at the top of Mt. Aconcagua, Argentina. It’s the highest peak in the Americas and apparently a fine place to have a cup of coffee.

What’s your historical San Francisco and New York connection?
I moved to NYC in 2006 with an ex-.  She had gotten into Columbia’s PhD program, but I had vowed never to leave the Bay – I even encouraged my dad to move out here.  I had one awful week at work, agreed to visit NYC, and was gone within 4 months.  (see #2)

Describe your experiences in SF and NYC.
I live in Oakland.  $#%t! Did I just disqualify myself?  …I was determined to move out to the West Coast since high school. I was snowboarding at Heavenly once, and saw kids come off the mountain, pack up listening to the Stones, and then head home like it was no big deal–and I hated them for it. I thought I’d move to Seattle, and had a job wrapped-up there when I agreed to be flown down here for an interview. Thought I’d use it is an excuse to visit friends.  When I got off BART at Civic Center I saw a bus driver actually KICK a guy off of his bus…it was mind-blowing after a terribly peaceful week in Seattle.  As a Southside Chicago native, something clicked.  I was home.

The Bay is (was) like that.  It rides the line between pacifism and outright chaos.  It’s nice to have options.

What is the biggest challenge of moving from SF to NYC to SF again?
The biggest challenge is convincing myself that SF is still as edgy, creative, exciting, dive-y, and welcoming as it used to be.  It just isn’t.  I hate to say it, but the tech community really is killing that aspect of SF.  Artists, creatives, hell-raisers–all pushed out.  Community is suffering.  People don’t put the same stake into their new neighborhoods, just sink lots of money into them.  It’s important, but not the same. And where are the $2.75 PBRs?! I’m still totally in love with Oakland, even as I watch it begin to suffer the same fate.

How can NYC and SF best engage with each other?
Just play NICE!  Look, I get it, New York – you still have better pizza…we’re gaining ground. But your burritos really just can’t compare.  It’s cute that you’re trying, though: effort noted.  Also, maybe you could found some start-ups out there?  Jeeeeez.  There really just isn’t any more room out here! Come visit, I’ll put you up! I’ll probably be out there again this summer.  I really miss it.  Let’s ride bikes.

Favorite SF secret spot
I don’t really do Yelp or much social media stuff, so this won’t be a particularly hip answer.  There’s a Uyghur Chinese place out in Parkside, Old Mandarin Islamic Restaurant.  They can make it SPICY.  (RIP old Yamo–with Tah-Weh Lee).  In Oakland, I head to Enssaro for Ethiopian – it’s walkable from my house, as is Coach Sushi and their refillable sake. That one is a stumbler.

Favorite NYC secret spot
Di Fara Pizza.  It’s not really secret if you know your slices, but few are willing to make the trek.  I spent a lot of time biking around the city and would swing by when I had several hours to kill.  Yessss, it takes that long.  It’s off the S line over by Avenue J. DiFara makes the pies with his bare hands–the health department doesn’t like this.  They have issue with the fact that he cuts his basil with scissors and sprinkles it on top. I was there one time when the [health] inspector paid a visit; spent the entire time glaring at him, hoping my masterpiece would come out of the oven before he got shut down. Again.

If you were not rocking the minds of middle schoolers, what would you be doing?
If I wasn’t rocking middle schoolers’ minds?  I guess I’d either be a test pilot, own a brewery, be an astronaut, or have my own little izakaya-type pizza shop. Preferably all of the above. I’d be like a Buckaroo Bonzai, but for beer and pizza.

Inflight Entertainment: tell us what song/album, TV show, podcast, or web videos you’ve been watching lately.
Inflight, I unplug.  Last flight, I started 7 Summits by Dick Bass, Frank Wells, and Rick Ridgeway.  It chronicles the expeditions of the first two people to summit the highest peak on each of the seven continents–they did it in one calendar year. I’ve peaked two, with two more in the works next year…I don’t have the bankroll to do it as they did.

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