Building a Network, Hosting Cocktail Parties, and the Importance of Hobby Projects with Nick Gray

Nick Gray has scaled and sold mutliple businesses. He’s the founder of Musem Hack, which started as a fun way to engage with art and artifacts and then grew much bigger than he ever imagined. He was also an important part of growing and selling a business his father started.

Today he does a lot of things. He’s always sharing his adventures and experiences online and in his newsletter, which I personally really enjoy reading and following. Most relevant to my life and our conversation, he’s been developing a method for hosting parties that I’ve been using. And it’s been a blast.

We’ll get into all of that in the interview, so I don’t want to spoil it here.

But what I do want to say is that I really like Nick. He’s approachable and open. He has a comfortable and genuine air about him, that I really appreciate. He’s the kind of person who makes you feel at ease. And I’ve really enjoyed getting to know him in this conversation and beyond.


Listen in here:

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Resources Mentioned:

Nick Gray’s Blog

Resource: How to Host a Party

Resource: How To Host a Happy Hour Event

Resource: How to Plan A Networking Event

Book: The 2-Hour Cocktail Party book

Software Generated Transcription:

Dan

Nick, thank you so much for joining me. Welcome to the Meaning Movement Podcast. So great to have you here with me.

Nick

Awesome. Thank you. Hello. I’m happy to be a guest.

Dan

Well, the question that I like to start with, I always start the podcast with is how do you begin to talk about the work that you do in the world.

Nick

I’ll tell you about Museum hack and all that stuff, but I want to know how have your parties been? That’s how we started talking. And that’s why we said, let’s have a conversation to talk about all these cool things that you’ve been experimenting with your wife.

Dan

Yes.

Nick

With your local community.

Dan

Yes. I love it. The parties have been awesome and are one of the first reasons that we connected because I think my business partner pointed out something that you’d done. Hey, check this guy out. I got on your email list and you just hosted a dinosaur party. I thought that was so awesome. I have kids, but it wasn’t a party for kids, which I thought was especially awesome. It was just you and your friends having fun, talking about learning about dinosaurs. That’s right.

Nick

I hosted a party for adults, an adult dinosaur party. I think we all could use more dinosaurs in our lives. My friend said that dinosaurs are like the gateway drug to science. And I thought that was pretty cool.

Dan

I love that. I love that. I’m vegetarian. And a friend of mine said bacon is the gateway meat for vegetarians eating meat. When you’re talking about gateway drugs, that’s just what comes to mind.

Nick

I love it.

Dan

Yeah. We’ve been following your method, throwing party — two parties in planning our third, and it’s been so much fun.

Nick

I would love to hear about it. For those of you wondering, you’re like, what is Dan talking about? My method. I have a method that hopefully on this podcast I’ll tell you more about later, a method that’s a step-by-step formula on how you can host a two-hour cocktail party. But first, I want to know from Dan, let’s talk about okay, because I talked to you after your first party. I guess that’s just to be real and sort of natural. How did your second party go? What went better? What went worse? What do you want to work on, or just what are you noticing for your guests that I guess just set it up. What are you doing? Yeah, totally.

Dan

Yeah. So maybe we should just talk about the format a little bit because it is a little bit different of a party. So it’s a two-hour party. There are name tags. There are ice breakers. We tell everyone in advance that there are going to be name tags and ice breakers, which I think there has been no push back about either of those things.

Nick

Good.

Dan

Which has been great and kind of serendipitously when we were starting to plan our first party in that planning process, we had another party that was already scheduled, which is our Christmas sing-along. My wife and I, our musicians, and something that we do every year, we invite friends over. It’s really silly. We just sing, play music.

Nick

And that sounds fantastic.

Dan

Actually call out Christmas Carol. It’s really great. You should come sometime.

Nick

I would love to.

Dan

And we’ve never used name tags, but we had already read that part of your book, which will talk about your book about the name tags. And then so that was like in our heads, but we hadn’t done it. And after the party, Stacia, my wife, was like, I think it would have been better if there were name tags. And so we’re already kind of thinking about that framework. And so I’m sure at our next Christmas sing-along, we’ll use name tags. But yeah, so it’s different in that there’s more structure, 2 hours. It happens on a week night. So it’s not competing with Friday night, date nights or other exciting things people have in their lives. The easier thing to say yes to. Sometimes it’s complicated with kids and babysitting, but people can usually plan ahead. And that’s basically the basic format. Am I missing anything?

Nick

You’re not missing anything. I’m imagining if one of your listeners is like, there’s name tags, there are ice breakers. Wait a second. This is an MLM. Dan. And I can promise you this is not an MLM.

Dan

There’s no pitching at all.

Nick

No pitching. The reason that I believe that more people should host more events is to make more connections after we got to dust off the COVID cobwebs. And this is a formula that can help you to meet people and sort of connect. I mean, I can talk about the nerdy science behind the value of weak ties and loose connections, but I’m curious for you. Let’s just start with what types of people are you inviting to your party?

Dan

Yeah, that’s a great question. So it starts with just friends, people that we’d like to spend time with necessarily have as many excuses, too. We usually have a handful of those folks, and then we then are looking at who are the people that we just want to get to know more, that maybe we only had a few interactions with, that we’re curious about, that we just want to hang out with.

Nick

Right.

Dan

And it creates a great contact for that.

Nick

So that’s really good. I’m going to jump in because you’ve identified two buckets of people here that these parties are perfect. The first bucket is the group that you said, people that we want to hang out with more who we just don’t get the chance to see as much. This is the coworker that you bump into. It’s like, oh, we should get a drink sometime. We should get a drink sometime. And both of you leave that interaction knowing the unfortunate reality is we will probably never get a drink together.

Dan

Absolutely. So one of the invites that’s out for our next party is a young woman that we reconnected with who was my wife is a musician and educator, and this woman was a nanny to one of her students. And we would like half a lot of interaction with her. And she seems super cool, but we just never had any context to interact. And then we bumped into her the other day, and then again, just a great connection. But then all of a sudden we have a next step. We’d love to spend some more time with her.

Nick

Yeah.

Dan

But it’s also like it would be weird to be like, hey, do you want to come and have lunch or something? Because that doesn’t work in our lives as much with kids and everything else. So it gives a great easy yes next step.

Nick

Yes. And you perfectly identified it when you always have your next cocktail party, when you’re hosting a cocktail, it makes it so easy to invite somebody and it makes it so easy for them to say yes, to think about how imposing it’s kind of a big deal to ask somebody to go out to dinner with you. That’s a big ask. That’s a heavy lift. It’s two or 3 hours out of your time. It’s their time. People have all these things. Anyhow, why should one of your listeners host one of these parties? Because it makes it easy for people to say yes to. And in the time that it takes for you to watch a movie, in 2 hours, you can connect with 15 other people. You can connect with 15 people in your life. So the first thing that you said is it gives you a way to kind of connect with those people that you would like to see more of, but you just haven’t life gets in the way. It’s not to say that they’re not important. It’s just that everybody’s busy. It is a lot to ask to do a block of dinner and it’s so hard to schedule, a cocktail party is so easy.

Nick

The second group that you said, I think, if I remember correctly, is people that you’re curious, that you want to get to know more, that you’ve bumped into them once or twice and you’ve seen them and you’d love to get to know them. But I think, like we’re saying it’s a big ask to be like, hey, do you want to have dinner? Because that’s really the only what else would you do if you met somebody cool and you want to get to know them better? What’s the step from one thing to the next? I don’t know totally.

Dan

Well, there isn’t a natural context in our culture, in the life that I lead to make those kinds of connections happen. I think of the times in my life when I had the most community, which is College is great because there’s people everywhere and you’re always having serendipitous connections and you’re eating meals, and so then there are people there that you can eat meals with and, like all of these things. But now I’m a parent. I’ve got three little kids, I work from home and I have a lot of friends, people that have collected along the way. But then I don’t get to see them unless we set up really intentional time, which is great. But then also it’s just hard to schedule and everything. And so what I love about it is that it reintroduces, maybe a context for those just small little interactions along the way.

Nick

Right. It’s that lightweight sort of connection. All right. I won’t hard sell it for your listeners. I’m not going to force them to say they should do it. I want to hear more about your stuff. Okay, so those are the type of people who you invite. You hosted the first party. Going into the first party, what type of hesitations or questions did you have? Or can you just talk about that?

Dan

Totally. Yeah. So I think going into it, one of the big things for me is, like, actually doing ice breakers. How awkward is this going to feel to do an ice breaker?

Nick

Right.

Dan

It takes a little bit of leadership of you stepping in, really owning that host role, saying, OK, everybody, we’re going to do this. Even if maybe people have different feelings about whether or not they want to talk or whatever, you just got to do it. And so going into that, that was definitely a reservation. Didn’t want my friends to think it’s weird, right? But it went super smooth and everyone really had a blast. And one of the guests who lives on the south side of the city, I’m on the north side of the city. The next weekend, we already had plans to see them, and he was like, hey, let’s host a Southend edition. He has a big house. My house is really small. It would be a great place to host a party. So I’m sure at some point in the next couple of months, we’ll do a Southend edition of a Cumberland cocktail party.

Nick

That’s the greatest compliment. When somebody says that you hosted such a good party. Now, I want you to host it now with me.

Dan

Yes, exactly. I loved it. And also it creates a cool opportunity for me to get to know more of his friends as well. There is a lot of good overlap, but then there’s a lot of new people that I could meet that should be really fun. I’m curious if you have experience co-hosting.

Nick

Yes. Oh, my God.

Dan

We’re talking about, like, this is next level. I hope the listeners are ready. We’re already at level three or four or five of black-belt cocktail parties here.

Nick

Black-belt cocktail parties. Look, let’s zoom out for a second. Why should you host a cocktail party. Why did Dan want to host a cocktail party? Why am I obsessed with this? Because I’ve gotten lucky. I’ve started and sold two businesses, and I now get to work on something that I’m truly passionate about. And it’s these stupid cocktail parties. I say stupid because everybody tells you, like, make a business start on something that’s going to make money. And I say that too. But I am so passionate about these parties and events. And by the way, it doesn’t have to be revolving around booze and alcohol. Dan can speak about that, but I don’t even drink alcohol. But I call it a cocktail party because that name, that phrase cocktail party, mentally holds the space in people’s mind that it’s something easy to show up to, that it’s not a strong commitment, that it’s not super formal, that it’s super casual. And so these events that Dan has been hosting are these two hour gatherings of friends and acquaintances where you mix up the groups. Part of the purpose of this is to introduce your friends to other friends.

Nick

And I guess you may have seen or maybe you could talk about that. Dan, what has it been like? You have probably seen some of your friends, meet some of your other friends and maybe make some new connections?

Dan

Yeah, totally. Absolutely. Yeah. I don’t know yet as far as how much those connections have left the room, but lots of really great energy happening between two people that have never met. I just remember walking into a conversation. I can’t remember what the topic was, but two women in my life who had no connection at all just really energized having a really fantastic conversation about something that like some shared interest. I don’t know. It’s like something like The Bachelor or something like that. I don’t even know. I had no idea that either of these people were into it, but they’re like, totally, totally. Like they were like, next level into it. It’s just so fun to facilitate that kind of connection.

Nick

The structure and the activity. Like Dan mentioned, doing these rounds of ice breakers. And to put it in context, this isn’t a complicated ice breaker. One of the first ones I recommend folks do is just to say, what’s your name, what do you do for work? And what’s one of your favorite things to eat for breakfast? What are we doing with that? You’re just getting people to go around the room and sort of sound off and say who’s in the room and just talk and create the opportunity at this party for someone to go up and introduce themselves and make a new conversation. These events are meant for people to have a lot of new conversations, to meet new people. And when you do this, you’re going to become seen as the person amongst your friends that connects other people. You’re going to get invited to stuff. Like Dan said, someone will ask you hey, can you help me host this? You’re going to meet new people, get exposed to their networks and friends and connections. So that’s the gist I’m hyped about this. I can talk about whatever you want.

Dan

I love it. Well, just one more just kind of tidbit about it. That question is the question that we’ve begun both parties with probably always will begin parties with that one. The second question that we asked was about city hacks. I love that it was one of the ones that you suggested, what are the best city hacks that you have? Things that people might not be taking advantage of are ways that you’re able to use the city in ways that people might not know. And those two questions combined, the city hack, one in particular. People are taking notes. People felt like they left with a new understanding of how to go about doing things in the city.

Nick

Right.

Dan

So that was like almost a month ago now. Just last week got together with one of my friends who’s at that party for his birthday, he invited my wife and I to go and get breakfast burritos with he and his girlfriend. And we went to a place that someone had talked about as having their favorite breakfast burrito. And so we went to a place that had been talked about at the party and then had come to find out that they’ve been going dow the checklist of everything in the city that was listed at that party has been their mission to try it all. It’s just so fun to see just how these conversations have bled out into their lives and how they’re spending their time, which is just really fun. I thought you would enjoy hearing that as well.

Nick

I love hearing that. I would have challenged you to say that those relationships, I don’t know if it’s made itself sort of outside the party doors. That is an amazing like when has somebody hosted an event and people are one taking notes during your home cocktail party and then they leave with an actionable to-do list. They’re like, damn. These people, your friends, Dan left your party making their lives better with new ideas and new things. And I think that’s just so powerful. And I love that you chose that question. I just want to know from a structural what are we doing there with those two questions? What’s one of your favorite things for breakfast? Why would you ask that at a party? That’s so silly? Why would anybody care about that? The reason is because that’s a green level round of ice breakers. That’s an easy question that people don’t have to think about. They’re not like, oh, my God, what’s my favorite book? Or I hate when people ask, like, what’s the worst first date that you’ve ever been on? How depressing? Let’s go around the room and tell bad stories of bad dates.

Nick

That can be funny amongst close friends when you can laugh. But I like what are called green level ice breakers, things that do not require people to think a lot, that are not like you’re not going to judge somebody if they say.

Dan

What do you have for breakfast.

Nick

A bowl of blueberries and honey. Right. You’re not going to judge somebody. You’re not going to be thinking people aren’t going to feel judged. And it’s just an easy way to loosen up the room to get people comfortable. So that later, an hour later at the party, when you ask them, what’s one of your best city hacks? What’s an example of a city hack, a great restaurant that you enjoy, a secret library that nobody knows about, a cool cocktail bar. When you then ask that question, people are warmed up, they’re ready to talk. They’re more ready to share. So that’s when we talk about doing ice breakers at this party, it’s basically two or three of these ice breakers, and they’re spaced out over about 35 minutes. At your party, Dan, are you doing three ice breakers or do you do two? So do you do that first one for your first group or do you wait or what do you do?

Dan

Yeah, we’ve been doing three. So we’ll do the first one 10 minutes or so into the party, which most people have been there. Maybe there’s one or two guests that are still haven’t arrived. But yeah, the party starts at seven to nine is what we’ve been doing. And it starts at seven. First round of ice breakers, like seven to ten. Then we just go and then we do three over the course of the evening.

Nick

Cool. All right. Great.

Dan

All right.

Nick

I feel bad. I feel like I’ve maybe hijacked this interview. So I’ll shut up now. I’ll let you ask your podcast. I’m happy to be a guest.

Dan

I will talk about this all day. Yeah, I love it, too. And really, I was looking forward to this interview because I want to have this conversation with you because more so than most guests, maybe all guests. I feel like you’ve had such an impact on my life because of this, because we’ve been doing this. And so one. Thank you. I want to say that this has been such a fun experience for me and my wife and will continue to be. But then also just because I want to share this with my audience. Awesome. So I’m having a great time. I think our listeners will as well. One question I think it would be interesting to hear your input on is who should think about hosting a cocktail party?

Nick

That’s a great question. Who should think about who can benefit from hosting a cocktail party? You are very unique in that you and your wife know a lot of people. I get the idea from what I’ve talked to from different groups. So there are two types of people, I think, that can really benefit from hosting an event? One is somebody who knows a lot of people from different groups in their life, and you don’t get a chance to see those people, but you’d like to spend more time with them. Okay, so that’s one. The second, though, I will say it’s a little bit harder, but the benefits may be larger and that’s somebody who’s new to town or that has recently gone through some sort of a social transition, that could be a breakup, a divorce, or you’re moved to a new town and you are looking to create new connections and meet people. And why is this important for you to host an event? Because the best way to make new friends, new connections, new relationships, is to start off by adding value. What do I mean by that when you ask somebody, hey, can I go out to coffee to pick your brain and learn more about your job?

Nick

You’re starting the interaction, asking for something from something. Actually, if somebody reaches out to me, no offense, can I pick your brain? Like I’m busy? I don’t know about that. But if you’re like, hey, I’d love to invite you to an event where I’m going to bring together a bunch of random people and friends and you’re going to meet new people and have exciting conversations. That is a way that you can add value. Does that second group resonate with you at all? How would this party work in your experience? Would this work for somebody like that? And I’m open to feedback, so don’t feel like you have to agree with me.

Dan

Definitely. Actually, I listened to your interview on Build to Sell yesterday as I was just getting ready for this conversation with you. And at the end of that interview, kind of mentioned a little bit about parties and he said something about starting a business. And I remembered when my wife and I started our photography company, like ten years ago or so, I was wrapping up grad school. I’ve been doing photography, but we hosted this big called a big party. It was a big party. There’s probably 40 or 50 people there.

Nick

That’s a big party.

Dan

We call it a photo mixer. And I was doing headshots. We had this headshot booth and then we had lots of different components. I won’t go into all the details on that, but to this day, I go on LinkedIn and I still see photo. We use this very distinctive yellow background, still see photos that I took on that night, like in use actively in my network. And I cannot tell you the number of the amount of business that came from hosting that party. People who may have knew them from grad school, but they didn’t know that I was a photographer. I wasn’t studying photography. I was studying culture and leadership and psychology. And so it kind of asserted me, gave me a platform, I guess, to be in that photographer role and, like built our network because they were inviting friends of friends. And I think tons of value that was added as basically giving away headshots for free and plus all kinds of other great stuff and all these things. It doesn’t exactly fit the template of what we’re talking about here. But what it does is it gives you a platform for meeting people and for talking about what you’re doing and in a non sale-sy way.

Dan

So creating a fun atmosphere, adding value to people’s lives and talking about what you do. And I’d be really curious for someone who’s listening, who’s in a transitionary phase where that’s they’re looking for a new job or transitioning careers. I think that hosting cocktail parties would be a great way to get a new job. Not that you’re hosting a cocktail party and saying, all right, come to my party, I need a job. But just to say when you go around the room and everyone’s talking about what they do and you’re just saying, I’m kind of looking for my next thing. Here’s what I’ve done. I’m trying to figure it out and boom, go on to the next thing. But then you’re also connecting with new people, and then they know they have that in their brain that, hey, Nick’s looking for a new gig or whatever, and I might know somebody who he should connect with. And I think it could be a really great way to pivot, I guess you could say.

Nick

I think you’re exactly right. I talked about this in my book. There’s a guy who moved to Little Rock and he didn’t know a single person in town except for his wife’s family. He didn’t have a new job there. He didn’t know anybody. He didn’t even know somebody he could call up on Friday night for a beer. And he started to host these events. And we’ll talk later. How do you go from not knowing anybody to now? He hosts these events with a long waiting list. He got an amazing job. And he says, though he says, it’s not like I hosted my first party and I immediately got this VP level job the next week afterwards. Right. It takes time. You host a couple of events, you meet people, one thing happens to the next and it happens eventually. It happens organically. You’re not trying to sell—people can see through that immediately. Right. But what I love about your event, Dan, that you hosted this headshot party is you started out by adding value. You hosted a party where you gave people these free headshots that they continued to use ten years later, never mind if they’re still using that photo.

Nick

Ten years.

Dan

I don’t know.

Nick

Maybe it’s time to throw another headshot party.

Dan

I know, right?

Nick

But meeting new people and doing this as a party, it sounds counter-intuitive, right. That I want to meet people, so I should host parties. But the thing that maybe you have realized, Dan, and you could speak to this is once you make the commitment, once you say, all right, one month from now, I’m going to host a party on a Tuesday night. When you meet people organically at the grocery store, at a soccer game, at another party, you have an easy way to get their information. Hey, I’m hosting a cocktail party in three weeks. Can I invite you? That’s all that you’re asking, can I invite you? And it’s an easy way for you to form the connection, get their email address, send them a text and invite them to your party. I think that’s one of the best things. You just start to collect people.

Dan

I love it. I love it. And it’s just so much fun. I’m definitely like love connection. My wife is a little more introverted than me, but she also because the cocktails parties are small, I think just the right number of people, the right context for extroverts and introverts.

Nick

Let’s talk about that. Can we talk about that? Because people are listening to this. They’re like, Dan is a podcast host and Nick is a crazy lunatic. Of course they love hosting parties. What did your wife think about this? Can someone who is a little bit introverted succeed or how would they do this?

Dan

Yeah, definitely. I think what it’s done for her is it’s given her the spaces for those more intentional connections. And I think also the ice breakers give a structure that takes out a lot. Like when you’re at a social gathering, a lot of energy has to go into, like, how do I find my way in to a conversation or a connection point? There’s a lot of just kind of like searching. You kind of have to float things out there, float topics. And I think the structure really helps with that. The smaller group, 15 people, makes it a lot more like a bite-sized kind of party.

Nick

Yes.

Dan

The name tags really help with that. So I think there’s a lot of things that really kind of lower the barrier to entry that people are more introverted, kind of shy away from.

Nick

I love that phrase lowering the barrier to entry to new conversations. And these events have that structure. People I found are craving structure at these social gatherings. How many parties have you been to and you don’t know who’s there? You know, you’re supposed to maybe meet some people, but you kind of leave it up to chance. Who do I bump into at the drinks table? And now I’m talking to that person. What these parties do with a little bit of structure with name tags, with rounds of ice breakers. And then maybe you could talk about the guest bios. Are you using the guest bios?

Dan

Definitely, yes. So we send out guest bios before the event. We’ll send out not everyone, but yeah, definitely some guest bios.

Nick

And the guest bios, by the way, it’s not like Forbes, 30 under 30. You’re just saying like, this is my neighbor Rob. He loves to ride bicycles and he drinks a lot of tea. Ask Rob about the last book he read. It’s giving these things to make sort of introverted or folks who are a little more shy to feel more comfortable to attend your event. And I’ve intentionally thought a lot about that. I had a girlfriend who was very she had a lot of social anxiety. And so even in setting up how we do these rounds of ice breakers, we’ve thought about saying which way the circle is going, repeating the instructions multiple times, helping people to feel slightly more safe knowing the boundaries of what’s going to happen. So there’s very few surprises.

Dan

I love that. Well, when I get invited to let’s say when like, I get invited to a lot of parties, I don’t get invited to a lot of parties. I’m a dad of three kids and it’s covid times. There aren’t parties happening really. But when I have been in the past, there’s always this question, am I actually going to know anyone there? And if not, then it’s like this could be super awkward. And so I think the structure really and the bios all that really lends itself to it. I think what I’d like to hear, I think maybe even alluded to some of workshopping of this method. Let’s just start working backwards. How did you get into this? How did you discover the Nick Gray party planning method? Right. Where did this emerge?

Nick

This whole thing started when I first moved to New York City. I lived in New York City about 15 years ago. I moved there and I did not really know anybody. And while it may sound now like I’m on the mic and I host all these parties, I tell you, the first time I went up to a stranger at a bar in New York City and had a conversation, I was shaking. I only met people in the past, if my friends knew somebody, and then I would only meet them through that or through my friends of friends. And I made the decision after, frankly, moving to New York and not being very successful socially, I said I want to be able to make my own friends. I want to have my own group. I don’t want to ride in the sort of coattails of success of my friends. I want to have my own friends. And so I had a birthday party that was coming up and I used that as my excuse for my first non-traditional party. I didn’t drink alcohol at the time. And I had a bunch of tea that I had brought back from India.

Nick

And I said, I’m going to host a tea party where we try a lot of different types of tea. And I’ll use my birthday as an excuse because in your birthday, your friends kind of have to do whatever you want.

Dan

Yeah, totally.

Nick

And so I use that as kind of an excuse. And I invited some of my close friends from College and people I knew I call that my core group. I knew that they would show up. I knew that they would RSVP. And after I had invited them and got them to RSVP, then I felt more comfortable inviting some of these other people that I didn’t know as well who maybe would then come. So that’s how I got started with wanting to build my own social group in New York City to make my own new friends. And that has become really a secret superpower that allowed me to build up a lot of people to help me beta test what turned into a multi-million dollar business that I launched called Museum Hack, which did renegade Museum tours, first at the Metropolitan Museum of Art in New York. And then we grew it to many cities, and we had lots of employees and all that stuff. It was a wild ride. That is where it all started.

Dan

I love it. I love it so much. So let’s just keep rewinding here and maybe zooming out a little bit on your career, on your work. I have many questions for you, and we don’t need to get into all the nitty gritty details of Museum Hacks and the exit or anything like that. But I think what people here are always curious about and interested in is how you make the choices about what you’re going to give your time to, how you choose. Because we know that career paths for very few people, very few people have very linear career paths. It’s often squiggly and have circles and loops and whatever. And so I think that’s kind of where I want to zoom in on is okay, so you moved to New York. That was before you started Career Hack. What were you doing at that time in your life? And I know you’ve exited multiple businesses, and I don’t even know what the other business was before or after. Maybe just give us a timeline and that might be a good place to start.

Nick

Yeah, sure. I think about my life. I’m 40 years old now, and I think about my life on decades, almost that in my twenty s, I was largely working for our family business. My dad started it in the basement of our house. And after College, through a weird circuit of events, I moved back home. I tried to start a software company, and it didn’t work out. I moved back home kind of tail between my legs. And my dad was starting this business, and I figured I’d help him out for a few weeks. He was making aircraft, electronic equipment. You know that map that shows you where the plane is flying across the country? He made a version of that map for small jets.

Dan

Love it.

Nick

Yeah, it was very cool. I thought I’d help him out. And I ended up helping him hire his first employee and started to do marketing for his company. Started to do hiring and what I thought I’d be helping him out for a few weeks, then turned into a few months, and then it turned into a few years, and we grew that to about 70 employees.

Dan

Wow.

Nick

That’s really what I was doing in my twenties. And that’s what took me to move to New York in the first place.

Dan

Wow. Got it. So then, as you were starting Museum Hacks, were you still working at that? Working for that company?

Nick

Yes.

Dan

Leading that company.

Nick

I started Museum Hack as a hobby project, working on nights and weekends, saving up some money so that when I was ready to leave and work on it full time, which I never would have considered this Museum Hack being a full time job. It truly was just a labor I love. I did it for free. And what was I doing? I’d invite my friends basically to come to the Metropolitan Museum of Art with me and drink alcohol and run around and I’d show them my favorite stuff. And that’s how it started.

Dan

If you could contrast a Museum Hack tour with a traditional Museum tour, can you give me the contrast? What’s the difference?

Nick

Most Museum tours, you’ll see two, three, four pieces of art, maybe over an hour, and it will be through the lens of a narrative arc of art history and importance. On a Museum Hack tour, you’ll see 15 to 20 objects. It’s incredibly fast-paced, and we’re kind of just showing you the coolest stuff that’s in the museum’s collection. It’s like an unhighlights tour. We’ll talk about how much a piece costs. We’ll talk about how it was acquired. We’ll talk about things that are the worst pieces in a collection. Why do they have this? Why is this even on the wall? This is stupid. Why is it here? And speaking about art in that way, I think, was something really new that people weren’t used to. And when we launched the business, it was rather revolutionary in the Museum world.

Dan

Yeah, I love it. I kind of had this moment as I was listening to that interview and Built to Sell, which if people want to go dive deep into the business and everything, I think we don’t need to have that conversation here because I can just direct people over there to the business mechanics of it. But had this moment of like, picturing someone running around talking about art, and it feels like in a really personal way. And I feel like that’s maybe one of the differences, at least for someone who hasn’t been on the tour, on a Museum Hack tour, that it’s like this is important to me. I like this piece because of X, Y, or Z. And then thinking about someone going back to that Museum after having been on a tour and then going to see those pieces and kind of relaying this story and how meaning and purpose and significance, all these things that I think about a lot about this podcast talks about a lot and how much those things are conveyed, I guess, in a person-to-person contact way that something like Museum hacks really allows for that kind of transfer of experience in ways that a traditional tour doesn’t seem to.

Dan

Does that resonate with you?

Nick

Absolutely. And it’s why none of our tour guides worked off a script. They had to build their own tours. They had to talk about the things that they liked. I said, look, I can tell you my favorite things. Maybe some of those will be your favorites, but I can’t give you a script because you have to talk from your heart. You have to speak about the pieces that you’re passionate about.

Dan

I love that so much. I mean, that’s like the real substance. What this podcast is about and what these conversations are about is, like what is meaningful to you and why is it meaningful to you, which maybe is a good transition point to like, I want to hear from you. Like, how do you navigate those questions in your life? Maybe some of the good way to answer that is when have you been in a place where you’ve had to make a choice of, this is what I’m going to do, and this is why I’m going to do it. You mentioned a couple of transitions already moving back home, transitioning to New York City. But I just want to kind of get inside of your head about how you think about what you’re giving your time to and the purpose and meaning behind it

Nick

For those major life decisions, for example, why did you sell your business? Why did you leave New York City? Why did you break up with your girlfriend? For any major decision like that I feel like there’s a thousand reasons that play into those things. I really struggle with buttoning up. Why did you leave New York City? So let’s take that as an example. I left New York after living there for 13 years, and I really struggled with trying to come up with the answer to that. And I’ll tell you something, I used to tell people the factual reasons. Right. And try to go down through a list of bullet points.

Dan

Right.

Nick

This reason, that reason. That reason that the other. And I was talking to somebody who was a speech coach, and she said, oh, that’s depressing. She said, that’s gross.

Nick

She was like someone’s asking you this casual question and you’re going into these really deep, gut wrenching answers. She’s like, boring. And the root of your question was, how do you think about those transitions? How do you think about working on the things that are important to you? And I think about what’s the story that I want to tell what’s the story that I’m writing for my own life. What is that? I talked with my ex girlfriend and we met series of events. But basically it started with I slid into her DMs on Instagram and I invited her to a petting zoo party that I was hosting. I was hosting a party where I had hired a petting zoo.

Nick

Which, by the way this is not featured in my book. I’m not going to suggest people to host a petting zoo party, but actually it’s legit. Really good party. And I’ve dated people before and they ask, oh, how did you meet? And if we met on a dating app, the next question was always, which app did you meet on? And that’s a fine question. That’s an easy and people want to know that, but it doesn’t really lead itself to someplace in a conversation. And so we would instead say, oh, we met on the dating apps, and then we had this incredible first date where we went out and we did all these amazing things and we talked about it. It was a real thing that helped tell a better story than, oh, we met on an app. Which app did you meet on? We told the app and the conversation ends. And so I try to think about that a little bit is what’s the story that I want to tell and what brings out the best in this experience? Does that make sense? I don’t know.

Dan

Yeah, I think that does make sense. And I think that it makes sense. I love also he said, why did I leave New York City? It was a billion reasons. And I’m sure that moment, there could have been times when you’re like, oh, should I leave? Should I not? Ultimately, you decided to leave. And maybe that was a good decision, maybe that was a bad decision. It just is what it is. But I think so often with these things, we’re both like looking forward to try to decide what our next move is going to be? Listening to a podcast like this, trying to hear from someone like yourself about how you made these navigated these things in your life. But then also knowing that the answer really lies behind us. And by looking back, we can say, oh, this is how I can tell the story that’s cohesive here’s the thread that I can find through my life that I can tell narrate the story in that way. So in some ways, I guess I’m saying it’s an impossible question. I kind of need to recognize that. But at the same time, I think it’s an important question because it’s the question of what does it mean to be human?

Dan

How do we navigate this existence?

Nick

I like that. I like that a lot.

Dan

Yeah. For people who are listening, who are in a stuck place, maybe they’re trying to figure out whether they need to leave New York City or not or leave their job or something is not working for them and they’re not sure where to turn next. I’m curious for you, there’s two ways you could answer this. So choose your own adventure question. One is, have you been in a place like that and how did you navigate your way out of it? Or do you have any just general words of encouragement? If you just want to speak directly to listeners who might be in a space like that.

Nick

The first thing I want to say is that I learned this from a guy named Dan Sullivan at their strategic coach. Dan Sullivan always said, make your future bigger than your past. And as we think about our future, we often think about it in the context of our past and where we’ve been. And I always like to think like, how do I make my future bigger than my past? So that’s the first thing I’ll say. The second thing is I just want to acknowledge the realities of people making these hard choices. People that have mortgage payments, that have kids in school, that have a car payment, that have the realities that are holding them back. And those are very real and they are not something that I want to just say quit your job and start something that you love and that you’re passionate about. Here’s the reality of what I did. I worked on Museum hack on nights and weekends for probably two years until I really had the guts to leave my family business and work on this full time. I saved up money. I really didn’t do it until people were begging me to do it.

Nick

And they were just saying, you have to do this. Does that mean that I was a coward, that I should have done it sooner? Maybe. But it’s what I needed to know that it was truly the right thing. So I don’t know. That’s probably not bold or it’s not assertive, but for me, I really worked on this on the spare time until I had enough money saved. Up until I knew that it was right for me. I worked on it like a hobby. Like a hobby that I was obsessed with, obsessed with building the best possible product that I was so proud of for my friends. I started with what I would be proud of, not what could make the most money.

Dan

Yeah. Well, I think that’s a really important distinction because you had your day job, which then gave you the freedom to make it the best possible rather than that was the goal was make it as good as possible rather than make this pay me. And those are two different things. And I think ultimately, by making it the best possible, it probably resulted in you getting paid more because you had a better thing to sell. Right. But if we jump into let’s do this thing that I love and make it pay me we might be putting the cart before the horse in some ways. And I think that’s what’s kind of left out of the narrative. Like bet on yourself, go do your big thing, because sometimes you need more freedom. You need more permission to not pay the bills in order to make it what it needs to be.

Nick

I’m thinking about your headshot party ten years ago. I’m guessing that you didn’t say, all right, strategically, I’m going to what do I need to do to generate more leads for my business? What’s the best way to do that? Well, I’ll host a headshot party. I’m guessing you probably said let’s host a party. I can do headshots. I know that. And then you from starting from a place of providing value, the business and the results came from that. They came naturally.

Dan

Yes, absolutely. 100% true. Just by starting something, not knowing where it was going to go, but trying to create something that we thought would be really fun, my wife and I. Yeah. That’s kind of where it needed to go. It reminds me in some ways of Elizabeth Gilbert in Big Magic, she talks about her writing and that she says that she would never demand. Her words, of course, are so much better than mine. She would never demand her writing pays the bills, basically, which is easy for her to say. Right. Because she’s super successful. But it’s exactly what we’re talking about here. It’s like your art, maybe your art isn’t writing. I think about art as creating a generative experience for the world, for other people to not demand that it pays you to let it be what it is. And then when it comes and I think in your experience kind of came full circle, that you made this really cool, amazing experience and then it paid the bills. What you’re saying here just reminding me of what Elizabeth Gilbert says, which was just to say I think we’re onto something. I think this is a good and important message for listeners who might be in a similar space.

Nick

And what’s the name of her book? I haven’t heard of it, and I’m going to write it down to make sure.

Dan

Oh, yeah, Big Magic, it’s called. Right.

Nick

Nice. Would you recommend that book?

Dan

Absolutely. It’s fantastic for anyone doing anything creative. It’s a great book about creative ventures, writing, creating, following the muse, or whatever version of inspiration, wherever all of that comes from. She has some really great thoughts in there about it. So recommend that to you and to all of our listeners here. Nick, like coming up on Time, which I’m so sad about because I feel like I could go on with you indefinitely.

Nick

I know I have so many more questions about your party. Did you get the harmonica, by the way?

Dan

I did. Well, we already had a harmonica. We’re a pretty musical family. So for listeners, Nick encourages people to start the ice breakers get people’s attention by making a sound on the harmonica. And I did record it. Stacia recorded me calling people’s attention with the harmonica. I’ll try to insert it. Yes, I could send you the video and I’ll insert it here into the podcast so people can hear it. I should have practiced beforehand. I know it’s not hard to blow in a harmonica, but like a couple of times it’s like just really a weak sauce harmonica performance on my behalf. And it’s not even a performance. You just got to make a sound. And it was just like I got better over time.

Nick

It’s just a sound you’re using. It like a whistle. It’s just a calming, nice sound.

Dan

Yeah. It’s a really great way to get people’s attention. They always know exactly after it happened the first thing. They always knew exactly what to do once they heard it. So it was a great way. I want to pick your brain, too, about some more party stuff, but we’ll do that. We’ll do that offline for people who want to follow along with your work and maybe host a cocktail party. Also, I love your newsletter and people should definitely jump on next newsletter, but is there anything in particular that you would like to invite people to?

Nick

I would like to invite if you’re listening to this, I have a book that’s called The Two Hour Cocktail Party. I don’t know when it’s going to come out. It’ll come out in May or June, who knows? But if you’re listening to this, if you’re a friend of Dan and you’re listening to this, I’m happy to send it to you just like I sent to Dan for free. I’ll send you a PDF copy of the first few chapters and I just want to share this. I want to share it. I’m in that phase now, like of starting a Museum hack where I’m going to work on this for a year or two. I’ll think about making money off of it later on. For now, I just want more people to experience it and try it out like you did, because I don’t know about you, but after the last two years of COVID, I miss hanging out with people and people are looking for structure. They want to gather again. And it’s what we need to make friends. And how can you become that person where people are asking you When’s your next party going to be, where you get introduced and you get recognized at your local PTA meeting or when you go out to somebody’s event?

Nick

I think by hosting these parties that I have provided a very step-by-step tactical guide that shows you how to do it and especially how to make it easy. Please visit my website and I’m sure you can find it from there. It’s nickgray.net —N-E-T. And I’m sure find it there. Say that you’re a friend of Dan’s and reach out to me that you listen to his podcast and I’ll set you up.

Dan

I love it. I highly recommend it. My wife and I have been through read the book in its entirety, put the process in place and it’s had such a positive impact as I’m sure people have known by this point in this interview. That’s something I’m really jazzed about. So thank you, Nick, so much for being on the show. Thank you for that generous offer to listeners as well. So please everyone listening, go jump onto Nick’s website and get your copy of the book. Thank you for coming on. This has been so fun. Awesome.

Nick

Thank you very much. Dan can’t wait. Join one of your parties and maybe join one of those Christmas parties. It’s a singalong.

Dan

Yeah, the Christmas sing along. It’s raucous and silly and lots of fun.

Nick

That would be great. I love to join.

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