In 2019 My friend Philip invited me to a 2-hour cocktail party at his tiny apartment in the Lower East side. True to his word, the gathering, which was on a Tuesday night, started at 7 PM sharp, and at 9 PM he kicked us out onto Orchard Street to enjoy the rest of our night and/or to get to bed on time (since it was a weeknight, after all!)
I met a whole bunch of awesome people, and if I’m honest, I thought Phil was super cool for bringing such a lovely group of people together. The food and drinks were nothing to write home about, but no one cared. Phil stopped the party two or three times to get us to circle up and introduce ourselves and respond to an icebreaker prompt. It was pretty fun.
He mentioned during the party that he was following an early draft agenda, a recipe if you will, for such gatherings, that was being developed by his friend Nick Gray, who I knew of through other friends. Nick had started a company called Museum Hack that had blown up - in the good sense. They were leading creative tours in Museums around the city, so I guessed this guy Nick knew a thing or two about getting people together.
Cut to 2022 when Nick Gray’s book “The 2-Hour Cocktail Party: How to Build Big Relationships with Small Gatherings” came out. Here it was, four years later! I was fascinated to talk to Nick because I thought “How much could there be to this? Isn’t it all in the title!?” How much could the form have evolved over 4 years of prototyping and testing?!
I’ll tell you folks…this is a polished gem of a book.
If you’ve followed my work, you know that I’m a bit of a nerd when it comes to gathering/facilitation/conversation design. I love card decks about it, books, diagrams, narrative metaphors to fuel creative innovation in gathering science for skilled facilitators to bring diverse stakeholders together to tackle wicked problems. I have coached leaders on this skill, all over the world. I hosted many, many cohorts of my 3-month Masterclass on Facilitation that people lovingly described as “drinking from a firehose” of facilitation while somehow being spacious and deeply mindful of how we gather. Managing complex gatherings is a crucial skill!
Companies that can’t come together to discuss and decide on actions for their biggest challenges will not survive! And I love these types of gatherings - they are never the same, they have to be absolutely customized, and deeply considered.
Nick, on the other hand, has designed the “CheckList Manifesto”, the “Design Sprint” or the “Joy of Cooking”...not for any and all types of gatherings - but for one, single, Life-changing, surprisingly powerful gathering - a 2-hour, midweek cocktail party.
Nick’s book is designed with absolute beginners, or those hesitant or nervous to lead gatherings in mind…but masters of gathering will be pulled in too…I was.
Nick designed this insanely in-depth book to cover everything from snacks to drinks to how to write an invitation to…everything. Where to put name tags. How big those tags should be. You get the idea.
While I am a nerd in the sense of being an omnivorous gathering nerd, Nick is an obsessive compulsive nerd of this one form…and for good reason.
Nick believes, and I now do, too, that if more people felt more comfortable with having more gatherings we would all be more connected. The midweek 2-hour cocktail party just might save the world.
You can get the gist of the form from this conversation (I mean, even from the title!), but if you’re a gathering nerd like me, you'll absolutely enjoy Nick’s insanely thorough guide, which I found myself flipping through regularly as my wife and I prototyped our own first midweek, 2-hour cocktail party, which we titled a “Serendipity Salon”.
I think we all need more serendipity in our lives, and that’s why I loved the opening quote I pulled from my conversation with Nick - the ability to take a short conversation with someone and turn it into a deeper one, to create a space where your old and new friends can connect with each other…only good things can happen from creating more of that type of serendipity in our lives. My wife and I have hosted two parties like this already and, as Nick has advised, we have our next one in the books! I hope you will, too.
Links, Quotes, Notes, and Resources
The 2-Hour Cocktail Party: Book info
The 2-Hour Cocktail Party: Amazon
3 Tips on How to Plan a Networking Event
Clothing Swap: How to Plan the Party
How to Host a Happy Hour: Tips, Tricks, and Best Practices
Minute 8
Nick Gray:
Now, one of the key elements of the Nick Party Formula, which is N-I-C-K, name tags, icebreakers, cocktails only, and K stands for kick them out at the end. The N, which is name tags, has become something so natural to me that I don't even think twice about it. But your question made me think, "Gosh, what was it like the first time I used name tags? Why did I use name tags?" And I tell you, I meet so many people, I host so many events that, maybe this has happened to you, people know your name and you... I'm very bad with names or I'm someone who is bad with names at times. And so I said, "I'm just going to start to use name tags from my own need and want, that I don't remember them." And then I saw how much it helped other people. Constant experimentation and then reflection afterwards of who were the best guests? What were the best activities? How did that go? How do I think about that? That's something I'm very, very intentional about.
Minute 15
Daniel Stillman:
So it's very interesting because sometimes new ways of doing help us think and be differently. There can be that transformation of, "Here's how to do it." And I think it will open up things for people. I want to really zoom in on this idea that... So, you mentioned serendipity and serendipity has been one of these words that has been lighting up and expanding for me. Specifically, this term about building serendipity engines in our lives. And so, because doing a party once will not be the engine you're talking about. So, a minimum viable party is not doing a party. In a way, what is the viable party habit in order for it to become an engine of serendipity in someone's life, do you think?
Nick Gray:
Well, and how you can take it to turn it into an engine of serendipity is by always having your next party scheduled on the calendar. Why is that helpful? Because today's Tuesday, as we record this, you go out tonight, you meet somebody interesting either at the line in the grocery store, on the subway, at a party, at a friend's house. What is your next step of action if you think somebody's interesting? I got to be honest, these days it's very rare that, besides me inviting them to a party, that I would say, "Hey, we should really have dinner sometime." That is a reach for me and, I think, for many other people. It requires a large level of commitment, vulnerability, scheduling is difficult.
But what I found from living in New York for 13 years and meeting thousands of people, was that I could invite them to my party and it was a very easy invitation. By the way, that's why I call these cocktail parties. It's not about the drinks. I don't drink alcohol myself. I don't know how to make a cocktail. But the phrase cocktail party encapsulates a social construct of a lightweight gathering where you'll have a lot of little conversations with minimal commitment, where you can bounce. You don't have to be there like a dinner party, you're trapped, you're stuck, that's three hours.
Minute 33
Daniel Stillman:
If you're doing this monthly, what is the cadence that you would recommend to somebody, and how do you create variety of the list from party to party?
Nick Gray:
For myself, generally the advice I tell people is every six weeks or so, you should be hosting something. And I like to invite about half regular people and half new people. And that helps mix it up. Using those words as well, there's always new people. Using that phrase when you explain it to somebody, number one, makes them feel more welcome. They're not walking into a party with established cliques. And number two, makes them not feel left out if they don't get invited again. The idea that there's always new people is something that will make these parties a success.
Minute 37
Daniel Stillman:
Why do the first icebreaker so early in the party? Because I know in your agenda, it's almost right out of the gate, right? It's pretty early in. Everyone is not necessarily even going to be at the party yet. And as an experienced facilitator, I still felt awkward breaking the frame of the traditional party. Which is, things are just kind of happening and everyone's kind of on their own. And to bring in structure early in the party, breaks the pattern and shows people a different sort of thing is happening here. I actually think it takes guts. Even as an experienced facilitator, I'm like, "Oh my God, this is not the place for me to be doing this." So, why do it? And, why do it so early?
Nick Gray:
So as an experienced facilitator, you may appreciate my reasoning on this. Many of my readers have never hosted an icebreaker before. In fact, they're terrified about the idea of leading an icebreaker. And so that first icebreaker, number one, is meant to get them out of the awkward zone. But number two, is to show them that icebreakers work and to make it easier to stop a party with fewer people, to know that when they have to stop it 20 minutes later when everybody's there, that it's going to work.
So it's for the purpose of the facilitator just as much as it is to get out of the awkward zone. The awkward zone is the zone that I describe as the first 10 or 20 minutes of a party when you haven't reached critical mass. Sometimes the people that you don't know the best have shown up early and it just is what it is. It's awkward. We do an icebreaker there to just get the conversations broken up and add a little momentum, create some excitement.
But I really do it for the hosts. I used to hear from so many people, before adding this first icebreaker, they'd say, "Oh, I did the party and then I never did the icebreaker. Everybody was having fun, I didn't want to interrupt it." And what they're really saying is, "I was too nervous. I was a little scared."
More About Nick
Nick Gray moved to New York City with very few friends and less-than-stellar social skills. But Nick craved new relationships and exciting opportunities. He started hosting non-traditional parties—a move that opened doors he never could have imagined.
Today, after hosting hundreds of 2-hour parties, he counts business owners, artists, and inspiring teachers among a circle of friends that helped him launch a multimillion-dollar company, Museum Hack. Featured in The New York Times and The Wall Street Journal, Nick has been called a host of “culturally significant parties” by New York Magazine.
Full Transcript
Daniel Stillman:
Well then I will officially welcome you to the Conversation Factory. Nick Gray, thanks for making time to talk with me about talking.
Nick Gray:
I'm excited to talk about talking, and parties and networking and all those things.
Daniel Stillman:
Well, yeah, because isn't a party just a bunch of people... I mean, I suppose talking is one of the things that's supposed to happen at a party.
Nick Gray:
Yeah, yeah. Parties are a lot of talking. Although now that I think about it, what would it be? Yeah. And so parties are a lot of talking and I've written a book that just helps add a little bit of structure to that talking. What do you think about structured talking? Do you ever show up to a friend hangout with a list of topics to talk about?
Daniel Stillman:
Are you trying to reverse interview me Nick Gray?
Nick Gray:
Yes. Yes. You're the pro. I want to know the expert. What does he do?
Daniel Stillman:
Well, clearly you value structured dialogue. Right?
Nick Gray:
Yeah, yeah.
Daniel Stillman:
Well, I really want to start way back, which is, why did you want to undergo, undertake this project? Because I don't know if you know this, I feel like we talked about this over email, but I went to an early prototype of this formula, our friend Phil Van Nostrand invited me to a two-hour cocktail party in 2019. So, you've been working on this for a really long time.
Nick Gray:
Yes. I've been working on this for a long time.
Daniel Stillman:
Yeah. When did you first start having the conversation with yourself about, this is something I would like to do?
Nick Gray:
Literally, it was over five years ago that I had built a Google doc for my friends that was the outline of this book. And I never planned to make a book, but it was just something I did for fun, for free, for my friends to use when they moved to a new town or want to make friends. And about five years ago, I started to think, "Huh, maybe I'll make this into a book." So I've been thinking about it a lot. And I suffer from the disease of perfectionism, which is to say that, I just wanted to make the book perfect and beta tested and get it into a thousand people's hands before I came out with it. So that's why you went to a test with Philip, which is really proof, I think, if you want to tell your listeners, that is a small apartment and it is proof that you can be successful even in a small apartment.
Daniel Stillman:
It's true. And he didn't have fancy snacks or fancy drinks. He did, at the time, have an outdoor space which was pretty prime, and he was on Orchard Street. So it was a very cool apartment, which I presume you've been to at some point. So I want to go further back then, because why did you write this guide for your friends about how to have parties? Because that's-
Nick Gray:
I got so much-
Daniel Stillman:
... that's not normal, Nick. I don't know if you know this, not everyone does that. Right?
Nick Gray:
Yeah, to do that, I guess. So yeah, I've been writing and sharing on the internet for over 25 years and I got so many benefits myself, from hosting parties. I saw other people get benefits from hosting parties that I think, just like you know the benefit of conversations, I know the benefit of building a network of acquaintances. And I found that I was able to launch my business, have success through those relationships I built up in hosting these parties. And after I sold my business, I was like, "All right, this is my next thing. I want to give back. I want to share that with others."
Daniel Stillman:
It's such an interesting journey to undergo. Why that? You're like, "This is going to be my windmill. I will tilt at this windmill. This is the horizon." I'm sure you could have done many things and you do other things. This is the thing that's so fascinating to me, because recently I wrote an article about what we should do when we think about taking on a new project, because this is something that we are all faced with all the time. And, what made this light up for you?
Nick Gray:
So for me, I think about how much value I can give. What will have the maximum amount of value? And I have found that hosting a party, when I can actually get somebody to host a party, I get to talk to people afterwards. And the level of satisfaction and success and how proud they are and the sense of accomplishment from leveling up in a life skill. Something fun that I like to do is I like to teach people how to juggle. And about 50% of people I can teach how to juggle in less than five minutes. The other 50% will take me hours and I'm not able to help them because I'm not that patient. But about 50%, based on how I see them throw two balls, I can know, "Oh, you can immediately learn how to juggle." And I love teaching people how to juggle because they get that sense, that feeling of accomplishment.
Similarly, with writing this book and with making this my mission, I said, "Wow, this is truly something that, number one, I'm an expert at. I've taught hundreds of people how to host a party and I personally have probably hosted a thousand parties now, and I've learned a specific formula that can make a gathering very, very successful." And I just said, "Yeah. I think if I'm going to write a book, if I'm actually going to share a detailed set of instructions and knowledge and lessons learned, that really is the only thing that I could truly write about that gives massive amount of value." That is my why of why I chose this topic and why I'm obsessed with this goal and, gosh, why I'm spending so much time on it, which is kind of ridiculous.
Daniel Stillman:
It is amazing. Well, so I want to talk about this pursuit of perfection and go back to structured dialogue because it's interesting. You've been interested in structured dialogue for a really long time. Do you have a sense of when you started to be aware of, to understand, to be interested in structuring how people get together?
Nick Gray:
In hosting my parties... So I lived in Williamsburg, Brooklyn when I first moved to New York, and I didn't have a lot of friends. When I first moved to the city, it was for the express purpose of building friendships. I worked in the majority of my 20's in a family business, helping my dad grow a company from the basement of our house into a much larger organization. And I'm so thankful for that time but also, I literally lived and worked with my parents every single day of the week. A fun Sunday for me would be to wake up early, go to Waffle House, and then go to the office where I had the whole office to myself and get work done. Right? It wasn't healthy from a social perspective.
So I moved to New York, I think maybe I was 26 or 27, and I said, "I'm really going to work on making friends." And this is what helped, was a little challenge. My roommates in college had moved to New York and they were very successful. And I sort of felt a sense of rivalry or a feeling that I didn't want to live in their coattails, that I didn't just want to ride and mooch off of their success. And I said, "I'm going to make my own friends. I'm going to learn how to meet people." And I'd go to things like networking events and I just wasn't successful at those events. So I said, instead of going to bad parties, I'm going to bring the party to me. And I learned, through a series of experiments, that by adding a little bit of structure to those parties, I could make them much better for other people, which would then help me make more friends.
Daniel Stillman:
Yeah. Well, let's talk about minimum viable structure. What kind of experiments did you start with? When you think about your early experiments in partying, what was the spark for you to say, "Oh, let me do, blank." What was an early prototype that you ran?
Nick Gray:
Now, one of the key elements of the Nick Party Formula, which is N-I-C-K, name tags, icebreakers, cocktails only, and K stands for kick them out at the end. The N, which is name tags, has become something so natural to me that I don't even think twice about it. But your question made me think, "Gosh, what was it like the first time I used name tags? Why did I use name tags?" And I tell you, I meet so many people, I host so many events that, maybe this has happened to you, people know your name and you... I'm very bad with names or I'm someone who is bad with names at times. And so I said, "I'm just going to start to use name tags from my own need and want, that I don't remember them." And then I saw how much it helped other people. Constant experimentation and then reflection afterwards of who were the best guests? What were the best activities? How did that go? How do I think about that? That's something I'm very, very intentional about.
Daniel Stillman:
So what's so interesting to me about your book, and it is a really, really interesting book, is that-
Nick Gray:
Thanks for saying that.
Daniel Stillman:
So I don't know if you're aware of her work, I've had my friend Kat Vellos on the show, she has written a book called We Should Get Together. And it's about the friendship epidemic, or the lack of friendship epidemic. And you probably know, and many of our listeners probably know some of the statistics, actually Casper ter Kuile talked about this too. He wrote a book called The Power of Ritual, and he talks about how Americans, as a whole, lost one friend on average. Most people, if you asked them, "How many people can you talk to?" And I think you read about this in your book too. Everyone just has fewer people to go to.
And there's this idea, Casper's book is more general, it's like, "Hey, ritual is important and here's the power of ritual and creating ritual. And we lack it, and religion used to provide it and it doesn't anymore." Similar, I think, Kat does have recommendations, but they paint a palette of problems and options and opportunities. And what's fascinating about yours is that it's a bullet. I think it's a really good silver bullet, but it's such a specific, well-polished, well-honed bullet to solve some of these challenges of loneliness and disconnection. And you've stripped so much complexity out of it, you've made it so streamlined. It's such a different approach.
Nick Gray:
So, I like that you said that. And I don't feel that that's an insult, that it's one bullet-
Daniel Stillman:
It's not.
Nick Gray:
Right. It's not, right?
Daniel Stillman:
No.
Nick Gray:
Because my book is very targeted. And one of the biggest things I worry about is people like yourself or people like Kat, who you said, reading my book, which may seem like very elementary-level advice. "Here are the supplies to buy. Remind people to take their shoes off. Put a candle in your bathroom." Right? These are very, very elementary pieces of advice. But what I've learned in talking to hundreds of people, is that nobody teaches the basic skill of hosting. And there's a lot of books, I'm sure you've read Priya Parker's, The Art of Gathering, an absolute classic, that in my mind is written for experienced hosts. It is a very theoretical book that talks about the theory of why we gather.
I wanted to write the book for someone who's never hosted a party before. I want to write a book to take someone from zero to one, to encourage a whole new generation of hosts. And I'm hoping that that's what I'm doing. Turbo hosts, people who host already, yes, they can absolutely learn some interesting things from this book. They'll blaze through it in half an hour. But I also love hearing from people that are like, "Dude, I read your book three times. I highlighted it. My party is in six weeks, I've made all these notes." I literally had a guy who read my book... Yes, thank you. I see on the video, Daniel's holding up a book with a bunch of notes in it. I heard from some-
Daniel Stillman:
Well, because I am a highly experienced gatherer and I still read it being like, "Huh, that is in the weeds. Those are some interesting choices. I don't agree with all them, but those are interesting specific points of view." And I think there is something useful about, as you say, Priya's book is way up in the abstraction level of the why. And yours is...
So sometimes I talk about this, there's a classic thinking tool called the abstraction ladder where you talk about why, intention, with how. And you say, "What are we here to talk about? Gathering. Why do we gather? What are all the reasons why it is important to gather?" And then it is also important to talk about the how, and why is not more important than how. And people need to be specific at some point and concrete about, well how do we gather? Let us actually talk about the nuts and bolts of it. And putting sticky notes into bowls so that you don't forget to put certain things out is a great hack. It's a great reminder. I read it, I was like, "I do do that sometimes and I'm going to do that more often." And good hosts do that, because then you don't forget to put the cheese out.
Nick Gray:
So a lot of my book is about trying to create the MVP, the minimum viable party. Because I believe that the biggest benefits come to those who can make hosting a habit. Now I could have written a book about how to throw the craziest party and a step-by-step guide and, "Do this party to blow your friend's minds." But the reality is that people would read that book and they'd host that party exactly once. Because afterwards, they'd be stressed, they'd be frazzled, their home would be a mess and they'd be hungover the next day. I have found that if you can make hosting a habit, it will truly change your life. And I tried to break it down into the process. I'm looking at that ladder of abstraction and at the very bottom, the bottom tier says process level. That is what my book is 95% process. You're exactly right.
Daniel Stillman:
So it's very interesting because sometimes new ways of doing help us think and be differently. There can be that transformation of, "Here's how to do it." And I think it will open up things for people. I want to really zoom in on this idea that... So, you mentioned serendipity and serendipity has been one of these words that has been lighting up and expanding for me. Specifically, this term about building serendipity engines in our lives. And so, because doing a party once will not be the engine you're talking about. So, a minimum viable party is not doing a party. In a way, what is the viable party habit in order for it to become an engine of serendipity in someone's life, do you think?
Nick Gray:
Well, and how you can take it to turn it into an engine of serendipity is by always having your next party scheduled on the calendar. Why is that helpful? Because today's Tuesday, as we record this, you go out tonight, you meet somebody interesting either at the line in the grocery store, on the subway, at a party, at a friend's house. What is your next step of action if you think somebody's interesting? I got to be honest, these days it's very rare that, besides me inviting them to a party, that I would say, "Hey, we should really have dinner sometime." That is a reach for me and, I think, for many other people. It requires a large level of commitment, vulnerability, scheduling is difficult.
But what I found from living in New York for 13 years and meeting thousands of people, was that I could invite them to my party and it was a very easy invitation. By the way, that's why I call these cocktail parties. It's not about the drinks. I don't drink alcohol myself. I don't know how to make a cocktail. But the phrase cocktail party encapsulates a social construct of a lightweight gathering where you'll have a lot of little conversations with minimal commitment, where you can bounce. You don't have to be there like a dinner party, you're trapped, you're stuck, that's three hours.
Daniel Stillman:
It is much harder to get the check early if it's not working or if it's awkward. It's a high commitment space. So I love this idea, and I agree with you, that having your next party in the calendar is a way to continuously invite people into your circle if you want to. Do you have other intentional engines of serendipity in your life that you could identify?
Nick Gray:
For sure. I send a friends newsletter irregularly that began as just a simple BCC email to my friends. Maybe I send it quarterly or once a year. And I got that from my parents, who grew up in the Air Force, and their friends would move and get stationed at new bases. So they'd send these annual cards with life updates to all their friends that they had met. And I started doing my own version of that to my friends, maybe quarterly, maybe yearly, just what I'm up to, some cool books I read. I tried to add value. But that friends newsletter for me is definitely a serendipity engine.
And it's different. Because now, these days people are like, "Oh, you should start a newsletter." The problem with that is you start it around a topic and ultimately you get bored with that topic. It becomes a responsibility, not an opportunity. When I keep mine to a friends newsletter... I think everybody should have a friends newsletter. When I keep it to that idea of what I am interested in, for people that I know, yes, the audience is smaller, but I maintain the consistency. So I think that's one that I'm excited about.
Daniel Stillman:
That's awesome. Any others that come to mind?
Nick Gray:
I've been experimenting with using social media more, short form video on certain platforms, tweets on Twitter. I haven't seen the benefits that some of my friends share, that once they go viral. I'm probably seeing stuff, but at the moment it feels more like a waste of time.
Daniel Stillman:
Really? Because you are really active and super intentional about creating stuff on Instagram. I look at your posts and your stories a lot.
Nick Gray:
Yeah, I'm trying. I love doing my stories. I love doing my stories. I was reflecting on this with a friend and they said, "Oh, is there any downsides to sharing as much as you do?" And I said... Well, let's take you here for an example, Daniel. I don't know if you've commented on any of my recent posts. You might look at them but if you don't comment, I don't see them. And so many of my friends, I believe, have a relationship with me as a viewer. And so that would be something that's a little different. Yes, I get recognized when I go out. I actually, oddly, get recognized on the street sometimes. It's great and it's flattering, but also it's like, I don't feel that it's a two-way street and sometimes I wish it was more two-way.
Daniel Stillman:
Yeah. Yeah. So I mean, then this becomes a question of how do you get somebody from the sidelines of your life into the center? Because the parties are just the beginning presumably, right?
Nick Gray:
Yeah. Yeah. The parties are the beginning, but they're also better than social media. I do feel really strongly on the power of gatherings. I believe that the purpose of these parties is almost like you're auditioning your friends, and you're auditioning who you want to spend more time with. A party is a chance for you to gather 15 to 20 people and to afterwards be able to say, "Oh my God, I forgot how much I love Dan. Dan is hilarious." I'm going to follow up and say, "Dan, what are you doing this weekend? I want to hang out. Let's try to do something." Right?
Daniel Stillman:
Yes.
Nick Gray:
And so I love parties for that opportunity to reconnect with acquaintances, to look at new people in our lives and to think about who we want to surround ourselves with.
Daniel Stillman:
Yeah. It is like taking that serendipity and just pushing that flywheel and getting it revved up and going again.
Nick Gray:
The serendipity flywheel. That could be a good article.
Daniel Stillman:
Totally. Well, so one thing that I really thought was so interesting in the granular level, the super how level of your book, that is connected to this idea of serendipity, was the language around growing your guest list. And being really specific around, you can bring a friend versus invite a friend.
Nick Gray:
Yes.
Daniel Stillman:
Can you talk a little bit about experimenting around that language? Because it was intentional.
Nick Gray:
Yeah. So many people who read my book want to grow their network. They want a new set of friends, they want to meet new people. Maybe they have the same friends that they do the same things with, but they wonder how their life could be different if they had more entrepreneurs, more writers, more podcast hosts in their life.
Daniel Stillman:
Let me tell you, having more podcast hosts in your life, definitely an improvement.
Nick Gray:
Game changer.
Daniel Stillman:
Game changer. Invite us to your parties.
Nick Gray:
Absolutely. They come with agendas for one, and you know there'll be show notes afterwards.
Daniel Stillman:
We may make a visual map, there may be stickies. Yeah, it's possible.
Nick Gray:
Right? There could be stickies, a visual map, which was awesome by the way. So, thinking about how you really meet new people. And one of the things that I'll hear from people is, "Look, you say in your book you need to have 15 to 20 people. I know about eight people. I know enough for a dinner party but not for a cocktail party this big. How do I get more people to come?" And one of the easiest ways is to ask all of your people, or some of your close friends, to bring a guest. Now I found through experimentation, that that is a very different ask than ask them to invite a guest. Inviting a guest is a simple act of, "Hey, yeah, I'll share the link to it." Bringing a guest expresses intent and action and results. Bring someone with you. Success is that you show up with someone. Inviting a guest, they could say yes or no.
Even in my own experience from hosting hundreds of parties and knowing thousands of people, I still only have at most a 50% success rate with inviting someone and them actually showing up, and that's like on a good week. Why is that? It's not because my parties are bad or they don't like me, well maybe it is, but people are busy. People have things going on. And so I tell people, make sure that you tell them to bring a guest. Ask them, "Who are you going to bring? I'd like to get a head count." And doing that, I think, is very helpful way to grow your guest list and start to meet more interesting people. I have one other master pro tip that I've never shared before that I can share with you because you're into this stuff.
Daniel Stillman:
Oh, I am.
Nick Gray:
So I have a Facebook group for people that have read my book and then hosted their second, third, and fourth parties. And I keep track of everyone who hosts one party, but then if someone actually builds this into a habit, I create a free group on Facebook just to share ideas. And someone was asking, "Hey, I'm really struggling with how do I get more people, more new people to come?" And I remembered the most successful thing I ever did. I said, "Look, I've experimented with a lot. Sending surveys afterwards, asking them to bring a guest. The number one thing I've ever done was the most aggressive thing." And it was the following. I stopped the party after I'd ran one or two rounds of icebreakers, so people knew that I'm a good host and I host a good event, when there was good momentum...
Actually I think I did this towards the end of the party. So everybody was having a great time, they knew that this was a good event. I stopped the party, I turned down the music, I said, "Hey everybody, I need five minutes of your time to help me. I'm trying to meet new people. The reason I host this party is to meet new people. So I'm going to ask you to write down someone's name, write down your own name and someone else's name." Then I passed out index cards and pens. I said, "Write down your name at the top and write down the name of two interesting people who I might be able to invite to one of my next parties." You don't have to write their contact info or anything. I'll follow up with you with an email that you can forward to them and if they're interested, then maybe they can reach out to me.
I passed those note cards out to everybody, they wrote down two names. I got so many referrals because the next day I sent them a nice message. I said, "Hey Daniel, thanks for coming to the party last night. Here's the group photo. You mentioned that I could maybe reach out to John Smith and invite them to the party. Would you mind forwarding them this blurb?" "Hey, my name's Nick. I live in New York. I host parties where I get together interesting people. We have name tags and icebreakers and it's two hours long near Washington Square Park. Write me back if you want to come." It was an easy message with the group photo that they could forward onto somebody. And doing that, in the moment at the end of the party to get the names, was the single most effective thing I've ever done to absolutely amplify all the invitations to my parties.
Daniel Stillman:
Yes. Now, I'm assuming that you didn't put that in the book for reasons.
Nick Gray:
Yes, yes, yes. It's advanced. It's an advanced level thing and my goal with the book is simply to get somebody from zero to one.
Daniel Stillman:
And I think that's so interesting that everything we make is our choices. There's choices inherent in everything we make. And I love that you were really clear and intentional on the zero to one, that you want everyone who feels like they want more connection in their life, that this is one clear action that they can take, which is making a party happen in their lives. And I want to just talk about something that we haven't been specific about, which is the fact that the name of your book, I'll say it in the introduction and this will seem repetitive now that I'm saying it now, and this is a weird meta moment, but it is a two-hour cocktail party. It starts at 7:00 and goes till 9:00, or starts at 6:00 and goes till 8:00. Or I suppose it could go from 8:00 till 10:00 if you're nuts and you hate your friends. And it's in the middle of the week because that's a day when people can actually, you can get people's time. Nobody has anything to do on a Tuesday or a Wednesday.
And the power of... And I think I sent you this on Instagram. Somebody had a sign, it was a cartoon where it was like, "Please leave at 9:00 PM." Knowing that there's a clear ending, where did that inspiration come from for you? Saying, "Look, it's not 90 minutes. That's too short. It's not two and a half hours, it's not three hours." You're like, "Here it is, two hours." What are you optimizing for and what are you sacrificing in that choice?
Nick Gray:
I'm optimizing, first and foremost, the number one thing that I've found that will guarantee the success of a party is simply the number of people. If I can get someone to have between 15 and 20 people to show up and they follow my rules and foundations, I almost know that their party will be a success. Why is that? Because the number one thing that will make a party a dud is if they don't meet the critical mass. A cocktail party works when you have the energy in the room that is exciting to walk around. That gives you the opportunity to meet new people and also a little bit of FOMO that you know you won't be able to talk to everybody. When you have a two-hour party, it's easier to say yes to, first and foremost.
Second, we host the parties only on Monday, Tuesday, Wednesday nights because those are non red level days that aren't socially competitive. A two-hour party also almost guarantees that you'll end it when things are going well. And what I found was that when I end it going well, people are ready to come back. They want to come back. They can't believe that it's being ended early, in their mind, and yet they thank me for it afterwards. "Oh my god, thank you so much." I'm seen as a host who brings leadership to the scheduling. So those types of things for me make it easier for people to say yes, they're happy when they leave, they thank me for it. And also frankly, I like my sleep. I don't want to go to bed at midnight when my house is a mess. I want to go on with life. I don't know, it's a very type A way of hosting parties.
Daniel Stillman:
It's very interesting. One of my favorite Shakespeare quotes... And this is from Romeo and Juliet and it goes by really fast. Most people don't remember this quote because it's not, "What light through yonder window breaks? It is the east and Juliet is the sun," which... Or "Goodnight, goodnight. Parting is such sweet sorrow," blah blah blah, all that shit. It's the scene when they're leaving the party after Romeo and Juliet have met and they've realized, "Oh shit, we're in love with someone who's from the other side." Mercutio comes up to Romeo and says, "Away. The sport is at its best."
Nick Gray:
Wait, that's a great line. Wait, that's incredible.
Daniel Stillman:
Yes. Now he's going to Google it and find out that I'm misquoting it slightly, I'm sure. But Mercutio says this to Romeo, he's like, "Look, we got to go. It's good. The party's good and we're going to leave at the peak."
Nick Gray:
Yes, that's the best.
Daniel Stillman:
Because this is peak end theory, right? Disney talks about this. People can Google peak end theory. So, ending a party at the peak is bold and it's a risky move to say, "You know what? There's more juice here, but guess what? Come back next month."
Nick Gray:
Is the peak end theory the same idea that they say that you should finish a vacation with a high note.
Daniel Stillman:
Well, so you remember the peak experience and then the last thing that happened. So this is one of the reasons why my wife and I talk about this, sometimes changing your location... Like, you stay someplace for 10 days. If you stay in two places, it's almost like you've been on two vacations because you remember, "Oh you remember we were in Athens, that was amazing, that meal in Athens." You're like, "Oh, and when we were in Heraklion in Crete, that was amazing." So you've made two peaks and you remember those two peaks and you remember both ends. And so yes, you want to end on a high note. "Away. The sport is at its best," because that's where people remember it.
Nick Gray:
I love that. In my book I talk about, briefly, how to end your party on a high note. And I talk about ending with a little bit of a cheer. And I do this often at my parties. It seems silly, it seems like summer camp, and yet it adds some finality to that moment. It adds an ending that's distinct, that's definitive and that's, frankly, so different from what most parties do. What do most parties do? Oh, people just start to trickle out, and eventually some people are the last to leave. Or the host makes some thing or some people make, "Oh, let's all go to this bar," or something like that to keep the night going. When you end it definitively, distinctly with some sort of fun activity, she talks about this in the art gathering as well, it really just sets your party apart. And I'm trying to give people a formula to host successful events. That, by adding a little bit of structure, you can set your party apart from a lot of different people.
Daniel Stillman:
You really can. And I can imagine now, your vision of the minimum viable party. We do not have so many of the institutions and organizations that allowed for gathering to be happening more regularly. I can imagine a world where everyone is just like, "Yeah, I throw cocktail parties once a month. I get everybody together." I think that's a better world.
Nick Gray:
I want that world. I want to live in that world.
Daniel Stillman:
Well, you do live in that world, Nick.
Nick Gray:
That's true. That's true. I do spend all day.
Daniel Stillman:
The rest of us are trying to get into that world with you. So one question I have for myself, personally, is do you ever find that 15 to 20 is the optimal number and if you get to more than that it's a different type of party? Do people want to always come back? How do you create variety in your list? If you're doing this monthly, what is the cadence that you would recommend to somebody, and how do you create variety of the list from party to party?
Nick Gray:
So it's a sliding scale of how often you want to host a party. I think you could host once a quarter, you could host once a year. For some people they never host and once a year may be enough for them. I talked to a guy last night at dinner who recently got out of a divorce and sold his business. He has more time and money than he knows what to do with and, for him, I said you could probably host every two weeks. You have a support staff to really do this, you know so many people.
For myself, generally the advice I tell people is every six weeks or so, you should be hosting something. And I like to invite about half regular people and half new people. And that helps mix it up. Using those words as well, there's always new people. Using that phrase when you explain it to somebody, number one, makes them feel more welcome. They're not walking into a party with established cliques. And number two, makes them not feel left out if they don't get invited again. The idea that there's always new people is something that will make these parties a success.
Daniel Stillman:
And so it's being really intentional about the fluidity and acceleration of this serendipity flywheel that you're running and communicating to people. You're not necessarily going to come back every time, but that's great for you. Right? Because I'll invite you to the one that's going to be happening in June and it'll be a different party then.
Nick Gray:
So my worst fear is that someone coming to one of my parties listens to this podcast in advance of showing up to my party, and they show up to the party and say, "Hey I know this is an audition, how do I ace it?" I'm just like, "Oh gosh."
Daniel Stillman:
Well then, I'm sure you have an answer for them. "Just have a good time."
Nick Gray:
Yeah, something like that.
Daniel Stillman:
Well, so I want to talk about icebreakers because it's so important and I feel like they're such a divisive concept. Because there are obviously people in the world who loathe the icebreakers in all forms, and there's some people who value them and crave them. And I imagine that icebreakers had a role in your first business... Maybe not your first business, in the Museum Hack. I imagine you had to gather people and move people around and connect them. How did you get into icebreakers? What was your philosophy of and how has it evolved, of icebreakers? Because I presume early parties, maybe you weren't as adept or adroit and you'd tried some that didn't work. Like before you said, "Here it is. Here's my unified field theory of icebreakers. At 7:10, 7:40, 8:20, these are what to ask. Go." Like you didn't hatch out of an egg with that complete.
Nick Gray:
About 12 years ago, I started to lead tours at the Metropolitan Museum of Art and it was a hobby project that later turned into a big business called Museum Hack. I realized in leading those tours, which again was something I did for fun for free, that I needed to get people talking. And so just like the number one metric for a house party is how many people show up, the number one metric for success for a museum tour was, are people asking me questions? Is this an interactive tour or am I just the sage on the stage who's performing? And I knew, or at least from my own experience I found, I needed people to talk and ask me questions. That massively made the tour that much better for me and everyone else involved.
To do that, I needed to get them comfortable talking in an art museum, which can be an intimidating space. And so very quickly in the first 10 minutes of a tour, I would lead a round of icebreakers that I found were very helpful simply to get people talking. The answers, I didn't care about. What I needed was for them to break the ice and start talking in the sacred space of the museum. That theory and that learnings and lessons came into all this party planning.
Daniel Stillman:
Yeah. Why do the first icebreaker so early in the party? Because I know in your agenda, it's almost right out of the gate, right? It's pretty early in. Everyone is not necessarily even going to be at the party yet. And as an experienced facilitator, I still felt awkward breaking the frame of the traditional party. Which is, things are just kind of happening and everyone's kind of on their own. And to bring in structure early in the party, breaks the pattern and shows people a different sort of thing is happening here. I actually think it takes guts. Even as an experienced facilitator, I'm like, "Oh my God, this is not the place for me to be doing this." So, why do it? And, why do it so early?
Nick Gray:
So as an experienced facilitator, you may appreciate my reasoning on this. Many of my readers have never hosted an icebreaker before. In fact, they're terrified about the idea of leading an icebreaker. And so that first icebreaker, number one, is meant to get them out of the awkward zone. But number two, is to show them that icebreakers work and to make it easier to stop a party with fewer people, to know that when they have to stop it 20 minutes later when everybody's there, that it's going to work.
So it's for the purpose of the facilitator just as much as it is to get out of the awkward zone. The awkward zone is the zone that I describe as the first 10 or 20 minutes of a party when you haven't reached critical mass. Sometimes the people that you don't know the best have shown up early and it just is what it is. It's awkward. We do an icebreaker there to just get the conversations broken up and add a little momentum, create some excitement.
But I really do it for the hosts. I used to hear from so many people, before adding this first icebreaker, they'd say, "Oh, I did the party and then I never did the icebreaker. Everybody was having fun, I didn't want to interrupt it." And what they're really saying is, "I was too nervous. I was a little scared."
Daniel Stillman:
Have you tried-?
Nick Gray:
And so, that's-
Daniel Stillman:
One of the things I struggled with was doing an icebreaker in the round, where everyone gets to hear everyone, versus a paired or small group icebreaker. And I'm wondering if you experimented with multiple rounds of small breakouts versus circling up and having everyone go round the horn. Because it's a very fundamental tension in pushing the conversation out to the edges, versus keeping it in the circle.
Nick Gray:
Yeah. I think you're exactly onto something special, which is that breaking into small groups is a little better. People are more engaged when they can talk more. Some people don't like to talk, but they probably like that more than the anxiety of going around the whole room. The short answer to your question is, you are thinking again as an advanced facilitator.
Daniel Stillman:
I know.
Nick Gray:
You have to remember that this book was written for the zero to one and for them to manage small groups and breakouts... What I find when I break people into pairs, you lose control of the room. You absolutely lose control of the room. And so I lead this activity, it's a module I've written about, I'll include it in the show notes, called Speed Ice Breakers. It's where you pair the entire room up, you split them into two lines, have them face off and you give them all one minute per question and then one line steps down and the other steps back. And you do about 10 minutes, 10 questions. And it's actually very hard. As soon as you release the group, everybody explodes in 10 different conversations. And to get their attention, to get them quiet 10 different times is really a lot of work. And for the purpose of this introductory beginner's book, it just didn't make sense.
Daniel Stillman:
No, it makes a lot of sense. It's about creating a frame that's not hard to explain. And reclaiming the attention of the group is non-trivial.
Nick Gray:
Oh my God, it's so hard. It's so hard.
Daniel Stillman:
So, also so hard, is to finish this conversation because we've just scratched the surface. It is a universe in this grain of sand, Nick. We are coming to the end of our time though. What have I not asked you that I should have asked you? What is important for us to talk about, to touch on that we have not touched on?
Nick Gray:
Well, we don't have the time for it but I would be curious, maybe we could sort of collaborate together on an article for my blog or something. But it's exciting for me to talk about the theory and the advanced facilitation strategies. So things, like you mentioned, that I was writing down, the peak end rule. No one's ever mentioned to me about the theory and the science behind these things. That, for me, I'm just in the weeds, "Put a candle in your bathroom and remove your bath towels." And you're like, "Oh, this is this. And this is this." I'm like, "Oh man, I should hang out with you more to sound smarter." Because I'm just like-
Daniel Stillman:
You're very kind. Well, so the question I want to... And I would be so happy to have a, we call it the 202 level two-hour cocktail party. What is the biggest difference between somebody who reads this book and does nothing and somebody who reads this book and takes action? Because that is your key metric and I think it is the key to transforming, to living in the world that you want to see, which is people are more connected to the people they want to be connected to. So what is the difference between somebody who doesn't throw a party and somebody who does? And what's the difference between someone who throws a party and somebody who develops a minimum viable party habit?
Nick Gray:
So, I would encourage your listeners to think about how their lives would be different if they had a full social calendar, if people invited them out to things, if you had new friends who encourage and inspire you. And know that all of that can happen. In the time it takes you to watch a Netflix movie, you could host a cocktail party for 15 or 20 of your friends. I've written a book that lists a formula of exactly how to do it for under a hundred dollars in supplies in even the smallest of apartments.
If you see on video here, I live in basically a studio apartment. I've hosted many parties in small apartments myself. That is my goal is to reach 500 people to read my book and host a party. There is a loneliness epidemic. We're in a friendship recession, so to speak. And I know that your parties will be successful because you'll help your friends meet other friends. And bringing those people together, I found that everybody wants to know someone who brings people together. All that it takes is a little party.
Daniel Stillman:
Aw. So can I actually just tell you with the one minute we have left, my wife and I ran a two-hour cocktail party in October in preparation for this and because I wanted to gather more. I also run an annual eggnog party. This year's the ninth year I've done it, although we had to skip a couple for the pandemic for reasons that'll be obvious to some people. And this year at the Eggnog party, which was a very welcome return, my friends, my longtime friends, the ones who I have been to eight of the nine or seven of the nine eggnog parties, said, "I met some new people." And that's because we invited several people from, what we called, the Serendipity Salon in October.
Nick Gray:
Nice.
Daniel Stillman:
And for one of my old friends to say, "You really helped me meet some... I love my friends and I love my friend's friends." And if it wasn't for the two-hour cocktail party, my eggnog party, my annual bash of boozy eggnog that I make from scratch in large quantities would not be as rich and interesting. So, thank you for that.
Nick Gray:
Really cool. I want to come to your eggnog party.
Daniel Stillman:
Sure. Well, I have some leftover eggnog, so if you're in New York in the next month or so, you can just drink some of the leftovers. It's good for several months longer.
Nick Gray:
It sounds like a party. Thank you so much for having me. This has been great.
Daniel Stillman:
Nick, thank you so much for making the time. It's been a really great conversation.