As my friends, family, and colleagues know: I affectionately call New York City “Fun Island.”
The name is a bit silly, but it’s directionally quite accurate.
Fun Island started out as a joke, but over the past 3+ years it served a very serious purpose: connect all the amazing people I’ve met in NYC together.
One of the reasons I’ve championed this so much is because I really do believe in the potential that the city has to offer. People from all over the world come to live here in NYC, and as a result you get an incredible melting pot of talent in everything from art and finance to tech, teaching, and hospitality. Few other cities have this type of density, and as importantly, the geographic friction is astonishingly low. You’re almost always 20 minutes away from anyone and anything.
Friction and Fun (Island) Dinners
That lack of friction is significant.
I’ve spent close to two years running dinners every Wednesday, Thursday, and Friday. That’s a lot! But surprisingly it never felt like too much (however 8 in one week was). Part of the reason I decided to do this was because I knew I could pull it off here. I don’t think I could’ve done this in any other city, at least not at this frequency.
Some people asked me how I did it. I think the truth is I just really like spending time with awesome people. Having small dinners is a sustainable way for me to stay in touch with the exciting people in my life; intimate, curated dinners are quite energizing, and far more productive than networking happy hours.
The dinners took a life of their own, and every few months I’d put on larger, more fun, Fun Island events like a Black Tie Boat Cruise, a Gatsby Rooftop Party, and most recently, a Summer Solstice Soirée.
A few people asked what the ROI for all this was — “why even do it?”
That’s not how I think. I don’t pull out a spreadsheet and figure out what I should or shouldn’t do when it comes to stuff like this. We all try to make robust, rigorous decisions. And sometimes a list or spreadsheet helps you do that. But sometimes you just feel a reason deep down that you can’t fully articulate. Fun Island dinners were one of those instances.
As I’ve thought more about them though, I’ve come up with plenty of great reasons. Seeing people ask each other hard questions is one. Watching founders grill each other is another. Hearing informal pitches was one too. But those are all pretty standard. The real value came from doing this 3 days a week, every week, for 2 full years. That’s how these friendships became so deep; brand new guests would hear people share some deep vulnerabilities, and some would even share their own. One of the things I’m most proud of from these dinners is that by the end of each meal everyone wouldn’t be strangers anymore. People have repeatedly reached out to tell me about ways they’ve continued to engage with fellow dinner mates, whether it’s ongoing email chains, business deals, or new best friends — even dates! I’ve heard it all. And I’m really thankful people decided to join.
Everyone in this city is special — if you spend enough time looking and listening, you’ll realize it. If you maintain a high bar for who you invite, then there’s no downside.
That’s why artists like Humans of New York do so well. The people here are endlessly interesting. Everyone has something to teach you. And we are all craving for a intimate space where we can share a small part of our story — ideally with an audience that’s excited to hear it.
That’s what I tried to foster. Some of my favorite memories come from dinners where I was the only person that loosely knew everyone. There were people I had briefly met via work or travel or some other way. After a few hours, that bond was different. You understood the others at a new, deeper level that you couldn't get from just having coffee chats.
I'm mentioning all this because I'm moving. I'm leaving Fun Island, and I'm sadly not going to be able to do as many dinners here moving forward (though I won't be stopping).
Life in Movie Quotes
I didn’t want to write a post about moving cities. It’s cringy and frankly not that important or interesting. People move all the time.
I wanted to write this to say thank you to all the people I met here who made my life better. It feels like I’ve been here for 5+ years, 10 even. And that’s because I’ve met so many people here and shared so many memories with them.
One of the wonderful things about friendships is you get to create a shared dictionary and language together. You create a set of inside jokes and silly incantations that you carry with you. I still remember ones from my closest friendships growing up.
I think it’s unique when someone introduces you to a whole new type of language, one that’s distinctly authentic to them. Over time it becomes native to you. One of my languages is movie quotes; I live life with a random assortment of them. It’s a personal super power — they’re always at the ready.
Some people don’t think it’s a proper super power. They’d say it’s more impressive to get all the answers on a quiz correct. To which I’d simply say: oh indubitably.
One quote I often think about is from Billions. I touched upon it in my piece on my late Grandfather:
There’s a quote from the show Billions that I love — one of the characters is asking Axe about two different obligations they have, and what they should do. Axe simply says: “You get one life, so do it all.”
You get one life, so do it all.
New York is a place where you really can do it all.
It’s not lost on me that Manhattan was where many people made first contact with America. My own Grandmother came here by boat — alone — and told me she always remembered seeing the Statue of Liberty, and this overwhelming feeling of hope.
That feels like a different world, especially in today’s day and age. But it wasn’t that long ago, and I’ve thought about this a good amount over the years in the city, especially because so many people I’ve met have journeyed their way here from all over the country, and the world. It’s a special thing to witness and experience.
Perhaps it’s poetic that I’m trading this city for California, another place deeply embedded in America’s brief history. Westward we go.
But before I leave, a goodbye.
The Alphabet & ABCs
There’s never a perfect way to say goodbye, so I thought I’d close by using some of that shared language here. To be honest, I’m a little sad. I suppose it’d be weird if I wasn’t, but that doesn’t make it any easier.
It’s hard to say goodbye. And you never have enough time to really do it. So in some ways this is a public thank you to all my friends in Fun Island. You made everything so fun. I’m going to miss you.
I thought about adding all their names, but I don’t want to embarrass them, so I decided to use their first initial instead.
A few of the many that I’ll miss: A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, Q, R, S, T, V, W, X, Y, and Z. (Unfortunately I missed befriending a U).
That’s a lot, and there are multiple people for multiple letters!
This isn’t a permanent farewell by any means. But I believe transitions are really important, and saying goodbye this way felt like the right way to process this one. The frequency and volume of encounters may decline, but the depth and amplitude will hopefully stay the same. Sometimes it doesn’t, and that’s okay too — that’s part of life. It’s like that magical wedding weekend where you have so much fun with the bride, groom, and all their guests.
It’s a perfect moment in time, and then it’s over. And that’s all it needs to be. Sometimes those are the most beautiful memories. The ones you randomly recall and make you smile.
I’ve had waves of memories come over me the past few weeks. More than I was prepared for. Some made me laugh hysterically, others made me tear up, and most made me feel happy. In some ways a day in NYC feels like 3 all wrapped together. Time expands and compresses in these weird ways and you’re left stepping back and realizing so much has happened in the course of a day, month, and suddenly years.
The act of stepping back is hard to make time for, but if you do then you usually are blown away by the progress. Writing this all out was one way to do just that.
You may be wondering, how long is this going to take? I promise I’ll wrap this up swiftly.
Some goodbyes are harder than others, and sometimes they require a unique way of showing how you feel and what the person means to you.
You Know My Methods
If you looked closely at my list of letters above, you’ll notice that there’s one missing. And if you didn’t catch it, I’ll let you go back up now and check. In the meantime, I’ll give you a pretty pointed clue.
I didn’t forget that letter. To be honest, I knew it would be one of the harder ones to say goodbye to. They made Fun Island what it is. In fact I even came up with that name while texting them.
I’m fascinated by the idea of a personal surface area — the shape of who we are, how that shape changes, and how others see and perceive that shape.
In many ways, most of what we want in life is to be seen and be appreciated for who we are. Sometimes you meet people that understand what shape you are much better than even you. Or maybe they see that small little part of you that others rarely do. They go out of their way to celebrate it — an amazing feeling to have.
This person did that and much more for me. And in a fitting way I don’t think we would have been friends in any other city other than Fun Island, because of the simple fact that it’s so easy to serendipitously get connected here compared to anywhere else.
The odds of us meeting are almost overwhelmingly small. But somehow we did; I’m immensely grateful for it, and far better off, too.
One of the cool things about friendships is when you look back and remember the first few times you hung out, you realize you didn’t know how that friendship would grow, or what it would become. It’s fun to realize how people’s personal surface areas sometimes click just the right way, and reflect back on which parts connected first.
In this case our first conversation consisted of answering questions about what we wanted to do with our lives while walking through a museum. True to form, I started taking about how I wrote a 10,000 word essay (for fun! During COVID!) that led me down a path I chartered for myself.
I don’t think most people would’ve seriously cared about that as deeply as this person did. I remember feeling embarrassed about how much we were talking about my answer, and then I realized that the curious mind I was talking to was genuinely interested in learning about me. Later I learned that they had already scanned my outfit head to toe; they subsequently admitted they already knew most of what I had told them about me thanks to their initial scan. Little did I know I was dealing with a modern day Sherlock Holmes.
But I digress.
Looking back, I’m really glad the past few years happened. I’m especially happy that I met the people I did — NYC made my life even more exciting. I’m really going to miss everybody, and I know that this next chapter will be better because of my time here.
We’re not here very long. I always try to remember that. After being in NYC for the past few years, I think the predominant takeaway is clear: go out of your way to get to know people. Build relationships with them. Be vulnerable. And be willing to develop deep friendships as a result. Life feels that much richer when you do. That’s why it’s called Fun Island.
And when you meet someone that really sees and hears you — recognize and appreciate that. They often become your biggest cheerleader, and they make you feel even better about you being you.
That’s what big ballers do. They bring the cool, and make the game fun for everyone involved, no matter who you are.
Thank you P. I hope everyone gets the opportunity to have a best friend like you.
PS - Big gulps huh?
PPS - the end…?