Let's Meet! Or, How To Pursue Serendipity

One of the things I love most is meeting new people who are outside of the usual circles that I travel in, who can teach me about things that I’d never learn about otherwise. To that end, I devote as much time as is possible in a busy schedule to having coffee or a quick chat with people around NYC when I’m able. And one of the most interesting people I’ve met that way in the past year is someone who makes those kinds of connections for a living, Ted Pearlman.

When Ted suggested a novel idea for connecting with people who otherwise wouldn’t be able to just grab coffee in New York City, I felt like I had to jump at it. While I’m a little uncomfortable with any context in which enduring dinner with me is presented as some kind of prize, the rest of the offer is so good that I got over my self-consciousness. Check out this deal:

  • You get a free trip to New York City, including airfare and ground transportation.
  • You get a night’s stay at The Gotham Hotel.
  • You get dinner at Danny Meyer’s Maialino, one of my favorite restaurants.
  • All you have to do to enter is tweet about it, as described here.
  • There’s nothing else, no terms & conditions or other obligations. If this were some sort of creepy spammy thing, I wouldn’t do it.


Earlier this year, Ted hosted an event called Meddle, which was a mind-bending, really challenging few days of learning from a smart group of people from a wide range of disciplines. Through Ted’s work on that event, I was reminded how much I love the learning that can only come from crossing paths with unexpected strangers.

Meddle Mini-Conference from Ted Pearlman on Vimeo.

At the same time, I try to be very aware of my privilege; I live in one of the most expensive cities in the world, and while I’m happy to be reducing the carbon footprint of all the air travel I used to do, that means it’s even harder for me to get face-to-face time with people who don’t live in New York City. It’s hard enough just to get time away from work to have a conversation where there’s time to discuss ideas.

So we’re trying an experiment. Even for someone with my ego, it’s a little cringe-inducing to say, “Hey, win dinner with me!” But on the other hand, I’d be delighted at the chance to win dinner with you. If that sounds cool, go visit the sign-up page and send us a tweet. (There’s a link to Ted’s private email address there, if you’re more of an introvert.) I particularly hope that those who wouldn’t otherwise have the opportunity to get to New York City will take advantage of this chance, and I’m optimistic that this kind of experiment can yield some positive outcomes for all of us.