What’s the Most Interesting Conversation You’ve Had With a New York Taxi Cab Driver?

Taxis drive on Park Avenue during a snow storm in New York City in 2005.

Photo by Ezra Shaw/Getty Images

This question originally appeared on Quora.

Answer by David S. Rose, lifelong New Yorker, Red Herring’s “patriarch of Silicon Alley”, Crain’s “father of angel investing in New York”:

Last winter, I had a tightly scheduled day and had to get from Park Avenue and 49th Street, where I was giving a speech at the Waldorf Astoria, down to lower Manhattan for an important meeting. Unfortunately, the move happened to be around 4 p.m., when taxi drivers change shifts, and there happened to be a blizzard going on outside. Needless to say, there was not an available cab anywhere to be found. I could have been in Siberia for all the luck I was having in getting a ride.

After 15 minutes of fruitless hailing, I was dejectedly about to bag it and blow off the meeting because it would have taken too long by subway, and there were no Uber cars available either. All of a sudden a taxi comes careening around the corner. Now, that’s not unusual in Manhattan, but the roof light was off (indicating that the cab already had a passenger and was prohibited from picking up anyone else), and as it screeched around in front of me, the driver reaches across and flings open the front passenger door, shouting “Get in, get in!”

Hey, this is New York, and strange things happen all the time, but this one was really weird. My first thought was, “I’m being kidnapped!” but I did a quick check and saw a legitimate medallion on the cab’s hood … and besides, did I mention there was a blizzard going on? So I cautiously got into the cab, whereupon the driver turns to his passenger and announces …

(Wait for it … )

“This is David S. Rose, the famous angel investor! We can’t let him stand out in a blizzard!”

Suffice to say, you could have knocked me over with a feather. After picking my jaw up off the floor, I stared at the driver in amazement … who turned out to be an entrepreneur moonlighting as a cabbie, and who had watched my TED talk on venture capital pitches and had then seen me at an event. The passenger turned out to be a business reporter from Fox News, and after we all finished laughing and exchanging cards, the driver dropped the reporter off at Grand Central, I volunteered to pick up her fare in appreciation, and we headed down to my meeting while the driver pitched me his company!

Only in New York, kids, does being an angel investor get you a cab in a blizzard. Only in New York.

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