Miles Penn: San Francisco

What’s your historical San Francisco and New York connection?
I grew up in NYC. I used to work in finance in NYC. Now I travel back for family, friends and MTailor related business.

I went to Stanford, just a little bit south of SF. Now I live and work in SF (MTailor is based in Potrero Hill), and most of my college friends are here as well.

Describe your experience in SF and your experience in NYC.
Growing up in NYC is a unique experience; I think I had a lot of personal freedom from a very early age. The thing I miss most is the incredible options for food delivery any time.

SF has been really fun. It is a lot more relaxed and outdoorsy vs. NYC. I bike to work every day (I think biking in NYC is a little insane). I also spend a lot more time outside the city than I did in NYC. I will visit the South Bay, go biking, hiking, go wine tasting, etc…

What was the biggest challenge of moving between NYC and SF?
The time zone difference is what kills me. Now that I am in SF and my family is still on the east coast, speaking with them is significantly harder. I am still at work when they go to bed.

How can NYC and SF best engage with each other?
I highly encourage that people visit the other coast and try something that is very “SF” or “New York.”

For visiting SF, I enjoy Philz Coffee.

For NYC, I love seeing Broadway shows.

Favorite SF secret spot
Fort Point (right under Golden Gate Bridge) — I like to run to it.

Favorite NYC secret spot
Angel’s Share — speakeasy bar in the East Village. You walk through a nondescript Japanese restaurant to get into this pretty fancy bar where they infuse their own alcohols.

If you were not where you are now, what would you be doing?
I’d either be back in NYC doing finance or starting another company.

Roadtrip Entertainment: tell us what song/album, TV show, podcast, or web videos you’ve been watching lately.
I’ve been watching a bunch of Veep on HBO recently.

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