The Big Apple

Remember that really nice kid in your 8th grade class who was always mocked due to something embarrassing thing that happened eons ago in elementary school (i.e. peed himself in class)? You may not be able to remember his name, but I can - it was Pittsburgh. Traditionally thought of as only a step above New Jersey in overall appeal, Pittsburgh suffers from antiquated notions of being a dirty, dingy city left reeling from the fallout of a collapsed steel industry. My couchsurfing host, Aaron, dispelled these notions quickly. He lives in a chic and comfortable three-level apartment style house complete with spiral staircase, downtown views and nearby quaint restaurants. The kicker? He bought the house for 30% of what it would have cost in any major and fashionable metropolitan area. Visions of investment firm “Youderian Vintage Apartments : Pittsburgh” began dancing through my head. Aside from the deals to be had, Pittsburgh is actually a gorgeous city. The skyline, as can be seen below, is one of the more beautiful I’ve seen.



After an early-morning laundry session in which I chatted with and interviewed (for the upcoming documentary) two fiery old men, I hit the road for New York. After many miles and accursed toll booths, I found myself in Brooklyn, NY. The plan called for me to leave my car in Brooklyn and head into the city. This plan, hatched through advice from a friend of a friend, seemed like a great idea at the time. When I actually got to Brooklyn at dusk and faced the idea of abandoning my beloved car to streets to fend for itself in a less-than-stellar neighborhood for three nights, I paused. The renters and car insurance I purchased prior to the trip eventually provided me with enough comfort to wish my car the best, say a prayer, and board the subway for Manhattan.

While it wasn’t quite as overwhelming and enormous as I’d imagined, the sheer immensity and activity of New York is still a sight to behold. I stayed with my buddy and co-DJ from college, Brian, in the North end of Harlem on 155th Street. During my two days, I managed to see the mandatory myriad sites: Time Square, The Statue of Liberty, Wall Street, Central Park, Fifth Avenue, Ground Zero, Harlem and, as all true geeks will fully understand, Apple’s flagship store. I was also able to get some great material for the perspectives documentary and interviewed a subway preacher, a homeless sax player, both an Indian and Pakistani girl and my humble host.

Central Park at Night


The Tech Mecca


Born to Invest?


Skyline from Central Park


The most enjoyable aspects of New York, however, were my experiences off the trampled tourist path. I attended my first Hanukkah party where guest were split into Jews and Gentiles and faced off to play a traditional dradle game modified to include both gambling and drinking. We were given a handful of gold chocolate coins which I assumed were gifts. Never one to let food sit untouched, I quickly began consuming the gold nuggets until I realized that they were to be used for the upcoming Jew vs. Gentile gambling and drinking showdown. It was with a no lack of of embarrassment and shame that I admitted to my host I had wolfed down my gold coins and needed new ones in order to play.

On two separate evenings I headed out to listen to live jazz and blues music in some small New York clubs. The first, Fat Cat, was a lively club with a fantastic jazz band and a wide variety of games for patrons to enjoy. A number of chess boards were set up and an old and weather man invited me to play with a wave of his hand. Two opponents and four games later, I was out $16. I have never been good at chess and this systematic flogging was not unexpected. My brother Chris and college roommate Ryan consistently humbled me whenever I challenge either of them in the past.

The other club, Bar 55, was a small blues club featuring Sweet Georgia Brown. An enormous and saucy black woman with an equally large voice, she was the self-proclaimed “Last of the Red Hot Mamas”. Whether or not she was the final surviving member of a dying breed, she made sure no one questioned her red hot status; sitting on the laps of patrols, openly discussing her enormous bosom and belting out lyrics like “Don’t touch my thigh because then you’ll want to touch my cherry pie” gave her complete and utter red hot credibility. Interested in booking her for your next wine tasting or church function? Feel free to visit her website.

I was waiting to catch the subway home after my last night out when I experienced something really cool. On the subway platform was a street musician strumming a guitar. While street musicians are everywhere in New York, this one in particular had a particularly powerful voice, a knack for capturing rhythm with his guitar and was singing well-known songs. A group of young kids started singing along with the infectious music and the idea slowly spread. People started to gather around and a homeless trumpet player joined the crowd. Before long, a massive crowd of people ranging from well dressed uptown yuppies to homeless men in camouflage fatigue were singing and clapping in unison, filling the late-night subway tunnels with noise. A stern-faced professional dropped his serious facade and began openly clapping and singing. Next to him, a homeless man momentarily forgot about his troubles and became lost in the emotion and enjoyment of the surrounding music. It was a sad moment when the train arrived some twenty minutes later and the crowd reluctantly dispersed. As soon as the train doors shut and the music was no longer audible, invisible boundaries once again appeared as people re-entered their individual worlds. But for those twenty minutes on the platform, joined together by the music and the late hour, we’d all let down our guard and a group of diverse strangers had shared in the spirit of camaraderie. It was, far and away, my favorite experience in New York.

Returning to Brooklyn the next day, I was overjoyed (praise God) to find my car untouched and containing all my traveling cargo. New York was behind me and D.C. lay ahead, my next stop on the trail.