Hosting Transformative Dinner Parties - Andy Ellwood

Josiah: 0:00

In this episode, we're going to look at how to host great dinner parties. Dinner parties? That's right. On this show, we talk about hospitality as a business, but I want us to become really good at living a hospitable life in our personal lives as well because the personal-professional divide isn't as clear as you might think, and if we get really good at doing this personally, we'll get good at providing hospitality professionally as well. To do this, we're learning today from Andy Ellwood, an executive coach, whom we met in prior episodes.

What makes a great dinner party? How much structure is involved?

Andy: 0:57

Yeah. So my favorite dinner parties are ones where people are comfortable saying, yes, I'll come, but they're not fully aware of everything that's going to happen. They're not fully aware of who I was going to be there, and I think that there's something about anticipation that I really love. I will send a text to three people that don't know each other and be like I'm sending this text because I think the three of us, the four of us, need to have dinner sometime. I'm not going to explain why. I'm just going to ask you to trust me, does this night or this night, work better for you? And it has turned out that turned out to be one of my favorite dinners of all of last year. It was three people that literally have. I know for a fact they would never, ever have met each other, right, but now, like the four of us are on that, on that text chain, and like there's a pretty consistent conversation happening about the topic of that evening, I host something called gentlemen's dinners with a buddy of mine and you know, and we've just found, that men specifically, well, men are idiots in general when women are around and that sometimes you just need like space to not like "guys be guys" but guys to have the opportunity to have the full range of who they are, right, and especially in New York City where we've got really tough exteriors giving guys the ability to ask questions of other guys who are similar, like circumstance, and it's incredible how much vulnerability can happen when the setting is correct. So there's gentlemen's dinners. My friend, John, and I started them and then we were fortunate to have a restaurateur named Carlos, become kind of a third co-host with us. So John and I started the first one in May of 19, and we've done 35 of them since, and the way we set it up was John invites three people he knows I don't know, and I invite three people I know he doesn't know, and we sit down for dinner and I cook. I got bored during the pandemic and I built an outdoor kitchen in my backyard so I've got my smoker, my pizza oven and my barbecue grill. Oh my gosh, it's a dream, yeah, and in the West Village it's a pretty special thing to be able to have that, you know, have the space to do that. But when we, you know we all get together cocktails, mix them in England, and before we sit down, I kind of explain the rules and the rule and I put this in the email which is in the invite also like restate it, but which is when you go find your seat, sit next to somebody you don't know, as best you can Not hard and fast, but like we don't put place cards out like saying you should sit next to somebody, just grab a seat next to whoever. And it's interesting to see kind of how that dynamic happens. We never have more than 12 people, so it's there's some. Well, I say, you know this person, okay, let's switch. Fine, but then the rule is that once the appetizers are served, we move into what we call a Jeffersonian conversation, which is one conversation for the entire rest of the night. There are no side conversations. You cannot whisper to your neighbor. If you say something, the entire table has to be able to hear it, and we do that until dessert is cleared.

Josiah: 4:15

And what does that do?

Andy: 4:18

The way that I've explained it is there are so many amazing perspectives at the table that it would be a shame for the gem of the night to happen in a side conversation. And what it causes people to do is to truly listen to whoever is speaking, not think about the funniest quip they can say, or the side under-the-breath comment to make their neighbor giggle, but it causes an entire group is all feeling the same thing at the same time, and the depth with which that drops strangers into community with one another has been really incredible and it's been so much fun to be able to see this and host 35 of these over the past four years to see some very, very successful men in New York City get really, really vulnerable, with some guy who just moved to New York it's 28 working on a start and they're like but I don't understand how, how does that work? And just a variety of perspectives. I think the youngest person that's ever come was 24 and the oldest person is 76. I think in the 76 year old he was like the musical agent for Van Halen. I mean, just like incredible. We've had some of the craziest people just who happened to be in town and so he was like, oh my gosh, I'm going to this dinner, can I bring some? And so we're like, sure, absolutely. And then we didn't really know who they were. But then they start telling us their story. We're like, oh, wow. But what's interesting is again almost going back to what we talked about with a leveling of the playing field at an offsite, because everyone is playing by the same rules and there's no hierarchy of host or this person is the loudest. Everybody is really actually curious about what everybody says, and without actual intentional pointing, hey, you haven't said anything yet. Do you want to say something? Everybody speaks all I mean. I bet if we timed it it would be. Everyone would have had the microphone for about the same amount of time, and it's really interesting. And then after dessert breaks, what's interesting? Like all right rules are broken, blah, blah, blah. We stay in a Jeffersonian conversation for probably another hour or two. Usually, Cigars are brought out. After dinner, drinks are brought out, and people they genuinely want to hear they generally don't like no one wants to miss the thing that somebody else might say. And so it's been really cool. And to kind of give you another kind of lagging indicator of how meaningful it's been is every single person who's ever attended a gentleman's dinner. I have all my spreadsheet that I keep like which, which ones were they invited to, which ones did they attend, and so I kind of have a good idea. So that you know, because we only can have eight people come if there's three co-hosts, that means only five people can. Five people can come, and we're trying to bring new people in also, right? So we started doing, is we started doing quarterly happy hours where anybody who's ever been to a gentleman's dinner can come to this happy hour. One of the 105 people that have ever come to a dinner with 65 guys show up at our last happy hour and the only thing they have in common is that they've attended a dinner. Wow, that's crazy. And they're like well, if you've attended a dinner then we must be like brothers Right, and everybody lives for the most part in downtown Manhattan and some people come in from Jersey, some people come in from Brooklyn, some people come in from Westchester, but we run into each other in the neighborhood all the time. Now, several people own restaurants in the neighborhood, some people own shops in the neighborhood, other people are doctors in the neighborhood, other people are small business owners and it's just really fun to see the way that community is kind of built. We really built it through the pandemic in a fun way and it's been fun. And so we love rolling up and kind of supporting the local businesses and be like hey, we've got 65 guys that would love to try your new restaurant out. Would you be open to us coming in? And they're like yeah, we'd love to have you. We pay, we're not asking for a drink or anything, we just want to make sure that they have the space that if we all roll up. But it's also really fun because we've been able to support local businesses through the pandemic and just by saying, hey, we're going to use support on a neighborhood, we're going to support you, and that's been a lot of fun to be able to kind of be one of the regulators of that crew.

Josiah: 8:46

Well, it's awesome to hear that story, Andy, because everyone talks about community and relationship building. I think there's two things that stand out to me as you're walking through that story. One is there's the person-to-person connection. Right, it's you texting a friend, it's you kind of getting to know that person initially and then taking the first step to make the connection to others. And then the second is structure, and I think people say clear is kind and there's something about people stepping into this environment where there's structure, you're providing guidance and maybe people are able to open up through that.

Andy: 9:16

Yeah, I think I don't remember what psychology study was, but if there are two playgrounds, one has a fence around it and one doesn't, and you take the kids to the playground that doesn't have a fence around it, it's just a playground in the middle of a field, most of the children will stay on the area designated as the playground right, like wherever the rocks or the platform are right for that playground. That's where they're like oh, this is where we play. But if you put a fence around the playground, you know 10, 15 feet outside of it, they will play in the grass all the way up to and, if not, on the fence. Those constraints give us comfort to know how far we can explore, how far we can go before we bump up against something. And there are definitely times where it's important to go beyond the constraints and things on those lines. But for you know, for something that's as innocent as a dinner party, as innocent as kids on a playground, it's a lot of fun to know. Hey, this is, if this is your first time, this is what it's like to be here, and that levels the playing field for everybody by knowing everybody else is playing by those rules and there being some sort of secret code about well, you know, every, every time he says such and so we have to take a drink Like everybody's on. That is on that same playing field, and I think that's sort of the magic.