Season 03 Episode 01
Will Guidara, Unreasonable Hospitality

Coining and striving for unreasonable hospitality

Chris Allen: Hey, I just want to welcome Will Guidara to The Entrepreneur’s Studio.

Will Guidara: Thank you so much, man.

Chris: How are we doing today?

Will: I’m so happy to be here, sincerely. Thanks for having me.

Chris: Yeah, you bet. I will say when the chance to have you here was on the table, I thought, “OK, well I have a lot of questions for this guy,” because I did get a chance to meet your wife [Christina Tosi, founder and CEO of Milk Bar] and have an extended conversation with her. You did come up a few times, so I was like, “This is pretty cool to sit down with Will.”

Will: You already got the better interview with her, but I’m happy to play backup.

Chris: I know, but she’s competitive. You know what I mean? You’re going to take it up a notch. She’s going to come back for round two. Super good.

Well, Will, you’ve been in the restaurant industry for a while. Since the age of 13 you’ve worked with the likes of Danny Meyer who’s sat in that seat. You’ve owned numerous award-winning restaurants, but you seem to be most known for and you get most notoriety for this idea of unreasonable hospitality. So talk to us about the core motivation behind that idea as an entrepreneur.

Will: Yeah, so my restaurant, Eleven Madison Park, the one I’m most known for, was named the number one restaurant in the world in 2017. I always like to say that the idea of being the number one restaurant in the world is an honor and also a little absurd. How can one restaurant be ranked number one out of however many hundreds and hundreds of thousands of restaurants? But what the list acknowledges is the restaurant that’s having the greatest impact on the world of restaurants at any given time. Our first year there was actually in 2010 and we went to the awards and I was all fired up and the awards themselves are not dissimilar to the Oscars, right? You go there, you put on your fanciest tuxedo, you’re in this room that’s larger than life. That room is filled with your heroes.

For me, they are the chefs I’d wanted to meet over the course of my entire career, but it’s very different from the Oscars in one very significant way. If you’re nominated for an Oscar, when they get to your award, you’re desperate that they call your name right here. If you’re in the room, you’re one of the top 50 restaurants, you just don’t know where on the list you fall until you get there. They start at 50, they count down to one. Here, you’re desperate that they don’t call your name for as long as humanly possible.

Chris: That’s interesting.

Will: And I remember we had assigned seating. I like to gamify everything in life. I actually think it’s one of my superpowers as a leader. I don’t care how much you like your job, we can all agree it’s more fun to play than it is to work. It’s so true. But if you’re creative enough, if you look closely enough for the opportunities that surround you, you can figure out how to make work feel like a game. And I think when you do, it’s transformational, because, well, people over the years have always asked me how I challenge my team to get better and better and better. And I always say, “Well, I didn’t. I just made our work feel like a game — and one we all really enjoyed playing. And anyone who’s ever played a game that they like playing, the more you play the better you get.”

Chris: So true as well.

Will: So we had assigned seating and I was looking at where we were sitting relative to where the people who had come in number one through five the year before were sitting to try to guess where on the list we were going to fall. I think I guessed number 35. They started the countdown and I’m sure there was some amount of the normal “Welcomes” and “Thank you for coming.” But all I really remember was the big, debonair British MC saying, “Coming in at number 50, a new entry from New York City, Eleven Madison Park.” I was like, “Shoot!”

It was pretty embarrassing. I was pretty angry. People always challenge my perspective there. They’re like, “Hey, you’re one of the top 50 in the world, why are you focusing on the fact that you’re in last place?” And well, it wasn’t a choice. I was genuinely angry. But I think perspective is everything. Have you ever seen “The Last Dance", the documentary about Michael Jordan?

Chris: Oh yeah.

Will: You know how he would, like if someone accidentally bumped into him, he would pretend they did it on purpose just to fuel his competitiveness? I think in this day and age, we’re so focused on mental wellness and positive perspectives that sometimes we overlook the power of anger and leaning into it and using it to fuel you. Not that we should ever sit in those emotions for too long… so I was pretty angry and it fueled me, but ultimately, that night I got to a place of acceptance. First, the idea that, OK, being number one is about impact. And when we got there, we were really excellent. Our food was some of the best in the world. Our service was as close to technically perfect as possible. Our dining room was one of the most beautiful out there, but those are the reasons we were on the list. We hadn’t actually done anything impactful.

The restaurants that topped that list before us did so by being unreasonable in pursuit of product. That night I chose to pursue a path where our impact was going to come from being unreasonable in pursuit of people, that we would push the envelopes of excellence in hospitality simultaneously, that we would continue striving for excellence, but we would also choose to be creative and intentional and unreasonable in pursuit of how we made people feel. For me, that’s what unreasonable hospitality means. It means you’re going to be creative, intentional, relentless, and unreasonable in pursuit of relationships, in pursuit of relationships with the people you work with and then as a team, collectively, in pursuit of the relationships with those you serve. Because I think if you do that correctly, if you consistently and meaningfully invest time, energy, money, grace into your relationship capital accounts, the opportunities that will invariably lie ahead of you are limitless and nothing short of extraordinary.

Chris: Well, motivation clearly came out that night. You emoted about that. What was really the first thing you did where you kind of harnessed this idea of not necessarily being excellent only in the product, but being excellent in the experience and the way that people felt? What was sort of the first thing you did after that moment at the award show?

Will: So I think whenever a leader has an audacious idea, the first thing you need to do before you even try to bring that idea to life is say it out loud to your team, right? My dad gave me a paperweight when I was a kid that read, “What would you attempt to do if you knew you could not fail?” And he would always encourage me over the course of my life and my career to answer that question honestly at varying intervals and whatever the answer was to try to do that. But he’d always say that far too many people are scared to say their most audacious goals out loud for fear that if they do and don’t achieve them, they’ll let themselves and those around them down.

Nothing audacious in my view ever happens unless you say it out loud to the people you work with over and over and over again — which by the way is a risk. Because if as a leader you say to your entire group, “We are going to accomplish something” and you fail to accomplish that, it’s hard on morale, but success is a team effort. You need everyone pointing their energy and their efforts in the same direction. So I went back and got the entire team together for a pre-meal.

Pre-meal, for those listening who haven’t worked in a restaurant, that’s the 30-minute meeting we have as a team right before we open the doors and start serving our guests. Most restaurants do it, a lot of them waste it. They waste it by talking about ideas that could so easily be communicated via an email — what you’re serving, a new dish, a new glass of wine, whatever. I think a pre-meal is an opportunity for a leader to share moments of inspiration and invite the team to do the same in return. I think a pre-meal is a time for goal setting. It’s a time to talk about the how and the why, not just the what. A well-run pre-meal is when the people you work with cease being a collection of individuals and come together as a trusting team. It’s my fundamental belief that any business that is charged with serving other people, if it had their version of a daily huddle where they shared these bombastic ideas about connection and importance, it would transform customer service as we know it.

I went back to the team and said, “Hey, we are going to be the number one restaurant in the world. It is going to take time. We need to be patient in our pursuit, but we are going to do it and we’re going to do it through focusing on unreasonable hospitality.” That was my role as the leader to say the what and the why, and then it was our collective role to figure out the how. Because I didn’t even really know what unreasonable hospitality meant. I just knew that was the direction we needed to go.

The first thing we did as a group was we started interrogating the guest experience. When I say interrogating, it’s a harsh term, but that is with intention. I think people in customer service often don’t know what every single one of the touchpoints in their guest journey are because they’ve never paused for long enough to consider them. If you can unpack and discover some of the most unlikely touchpoints and then figure out how to make them a little more gracious, a little more warm, a little more awesome, you can give yourself an unfair competitive advantage because you are now focusing your energy on a part of the experience that none of your competitors have ever even realized exists. The example I always like to give is Five Guys, have you ever been to Five Guys?

Chris: Oh, yeah.

Understanding every touchpoint of the dining experience

Will: What do you think of when you think of Five Guys?

Chris: Really good fries.

Will: Really good fries. Cheeseburgers are great.

Chris: Yep, yep.

Will: When I ask that question, a lot of people will say peanuts. Five Guys has that box of peanuts.

Chris: They do.

Will: Basically, when you’re waiting for your burger to be cooked, you can put some peanuts in a little thing and eat them while you wait. Five Guys, the only fast food restaurant in the world — as far as I know, had the wherewithal to recognize that the time waiting for your burger to be cooked is a part of the experience and they’re the only people who have done anything with that. And it’s given them an unfair competitive advantage because, well, the fact that they’re doing something when no one else is doing anything is pretty profound and because waiting for your food is a part of the experience.

Chris: It is, it’s a reality.

Will: So this is a long-winded way of me saying our first pass was truly understanding every touchpoint. Because only once you’ve isolated each touchpoint do you have the capacity to elevate them. I always challenge people. Regardless of industry, if you are in the business of serving other people, find a touchpoint no one else has considered and make it a little more awesome. That’s the definition of strategy. You can’t be better than everyone at everything, so you need to pick your moves and the smallest enhancement to the least likely part of the experience can have an asymmetrical impact on the way that experience feels.

Chris: It’s powerful. Now you did just talk about Five Guys and you have a friend who has another chain of burger restaurants.

Will: I do, I do.

Learning how to lead from mentor Danny Meyer

Chris: So talk to us about the influence of Danny Meyer and your relationship with him.

Will: I will, because that’s one of my favorite things to talk about, but I’ll just say this real quick — I love In-N-Out Burger as well.

Chris: You’re not even going to say the name.

Will: No, no, no. I’m going to say Shake Shack in a second, but... Danny Meyer is one of my two greatest mentors. Randy Garutti is the CEO of Shake Shack, and he was my first boss when I worked for Danny. Randy was my general manager, and it was my first job out of college. I posted something about In-N-Out Burger on Instagram one time, and it was literally like 45 seconds later that Randy called me. He was like, “Dude, what the heck?” So publicly, I guess I’m speaking publicly right now — Shake Shack is my favorite fast food burger—

Chris: For the record.

Will: I just want to make that clear, for the record. So Danny Meyer gave me the foundation upon which I’ve built everything. I think when you’re coming up and you want to pursue a path, you need a hero to look up to. You need someone who has achieved not only success but notoriety in that field so that you have someone who one day you want to be like. And Danny was that person for me. He was that person for me because he was the first person who took all the creativity that chefs have long been celebrated for putting on the plate and invested that into the way those plates were served. Danny showed me that, yeah, there was a world of opportunity in flexing the rules around how to make people feel seen when they walked through the doors and into your room, but he taught me so much.

I think one of the biggest lessons though is the power of language and the need to, with great intention, articulate what you believe, what your non-negotiables are, what your core values are, because until you’ve come up with these short, succinct little ways to articulate what you’re trying to achieve, it’s impossible for everyone in the company to be rowing in the same direction. I mean, Danny had all these isms, right? Charitable assumption, the idea you should assume the best in people and don’t jump to conclusions. Another way of saying it is don’t say the thing before asking the question. Seek to understand before jumping to judgment.

The swan, this idea of how in any service industry, we should be kicking below the surface like crazy people to try to be the most efficient and the most excellent, but on top of the water, we should look graceful like we’re just floating over the water. Some of my friends who graduated from college and I went to the hotel school at Cornell [The Nolan School of Hotel Administration at Cornell University]. We were all in various restaurant or hotel companies and would call our companies cults because we had all these shared language things, these isms. But I’ve come to believe that those who call one company a cult are generally working in a company that has not invested as much time or energy into their culture.

Chris: True, very true.

Will: And so Danny taught me that words matter and a leader, a great leader, has so many responsibilities, but one of those is taking the time to truly articulate to their team what they stand for while being consistent in upholding those values.

Chris: Something else I thought was really amazing — and you being here is kind of an embodiment of that, but when Danny sat in the seat and talked about this idea of building teams and building culture, one of the things he spent a lot of time talking about is his idea of having one restaurant and being excellent, but reaching a point where he realized there was nowhere for people to go. He had built these teams and built this excellence and there was nowhere for them to go. So he was like, “I’ve got to break out and give these people a place to go.” Is that something you experienced, where he created space for you to be more than what you were when you started with him?

Will: Oh, for sure. I mean, Danny, especially in those early years, he was really good. I got there in 2001, so I mean Danny had just one restaurant for a really, really long time. By the time I got there, it was starting to grow a little bit, so when I got there he had four restaurants. And it was difficult to find yourself feeling complacent there. Yet at the same time, he created such appropriate environments within each restaurant that you weren’t thinking about your next step, the moment you started the one before it. I think that’s one of the issues a lot of companies have, especially generationally as people are increasingly impatient and always focusing on what’s next.

The problem you can find yourself in if you’re in a growing company is that people are so focused on their next promotion that they never give themselves the time to bloom where they’re planted. I think what Danny did really, really well is create this balance between knowing that as long as you worked there, if you excelled, there would be opportunities for you to grow. But also instilling in all of us this understanding that we should be audacious in our ambition, but patient in our pursuit. Knowing that until you see all of the seasons pass in one role, it’s not even appropriate to begin thinking about where you want to go next. Because I think if you have one foot in yesterday and one foot in tomorrow, what’s the adage?

Chris: You’re missing the now.

Will: Yeah, you’re missing the now. I think that was a balance. He was very, very good at striking culturally.

Chris: Now let’s bring you all the way back to when you made your first move after the 50th place on a really remarkable list.

Will: Last place.

Redefining what it means to have a memorable meal

Chris: Yeah, I can see you’re competitive. Then walk us up to where’d you land in 2017 to get that number one spot? What were a couple of the stops along the way that got you there?

I do like this idea of radical reinvention. You’ve brought up the unreasonable hospitality foundation that you operate from, but what do you accredit or attribute to your getting to number one?

Will: Yeah, so the real breakthrough moment came about a year and a half after those awards, the first time we were there. This has become a legend a little bit because I’ve told this story a bunch of times, but it was about a year and a half later, and I was in the office doing emails during lunch service. I got a call from the maître d’ saying, “Hey, we’re getting killed out here. We need some more hands.” So I went out and just started clearing tables. By the way, as the owner of that restaurant, one of my favorite things to do was clear tables. I think it’s just a beautiful sign to everyone on your team that it doesn’t matter what position you hold, you are going to do the thing you are asking them to do, and you’re going to do it better than everyone else too, right? Danny used to say, “Show your fire. It doesn’t matter what leadership role you’re in, you better make sure that at varying times you’re stepping in and reminding people how you got the job you currently have.”

Chris: Powerful.

Will: I found myself clearing appetizers from a table of four foodies. They were Europeans in New York on vacation who were just there to eat at restaurants, and this was their last meal. They were literally heading to the airport right after their meal to go home. And while I was at the table, I overheard them talking and they were going on and on about the amazing trip they had and talking about Per Se and Le Bernardin and Daniel and Jean-Georges, all the great restaurants. And now they were at Eleven Madison Park. Then one woman jumped in and said, “Yeah, but you know what? We never had one of those hot dogs from a street cart.”

It was like that moment in a cartoon where the lightbulb goes off over the character’s head and they’ve had a good idea. So as calmly as I could, I walked back into the kitchen, dropped off the plates, and then literally ran outside to the street corner where one of the hot dog carts lived, and I bought a hot dog, ran back inside, then came the hard part convincing my chef to serve it in our fancy restaurant.

But I asked him to trust me. I told him it was important to me. That second line was a big one. We talked about this earlier. If you are lucky enough, which I was at that time, to work alongside an entire group of like-minded people who are passionate in wanting to be the best at something. I mean, my gosh, that’s a blessing. Because I can all but guarantee every single person listening to this has had the experience at some point in their lives of caring more than their colleagues. And it is one of the most soul-sucking feelings.

Chris: It’s very lonely.

Will: So once you get to a place where you’re surrounded by really passionate people, you better not lose the perspective where you stop appreciating that, where you start taking that for granted. That said, when it is the case, there’s always going to be tension. Because if you work with passionate people who agree on wanting to be the best, you’re going to constantly disagree on what it takes to become the best. So we had a ton of tension in our restaurant all the time because we’re all really passionate and competitive and we all wanted to be the best. And we all came from different walks of life. We had different ways to navigate through the tension.

If you and I were ever arguing about something, either one of us could just say at any point, “Time out, switch sides,” and then I’d have to argue your position and you’d have to argue mine. What you very quickly realize is most people just want to be right. And the moment I start arguing a position that just moments ago I was arguing against, now I want this position. If that didn’t work, you could say, “OK, time out again. Third option,” which meant, “Hey, if neither one of us has been able to convince the other person, maybe we just don’t have a good idea on the table yet and maybe we need to work together to come up with something different from either of our perspectives that’s actually better for the business.” Or if that didn’t work, someone could just say, “This is important to me,” and that meant, “Hey, this is more important to me than it is to you, and so I should win this one,” which I do believe to be true. There is the underlying rule though that no one should ever be abusing that “this is important to me” card.

Chris: It takes trust.

Will: Anyway, so we cut the hot dog up into four perfect pieces, added a little swish of ketchup, a swish of mustard, and a perfect little scoop of sauerkraut and relish to each plate. And before their final savory course, which was a honey-lavender glazed Muscovy duck that had been dry-aged for two weeks, I brought out what we in New York call a dirty water dog to the table. The simple little gesture changed everything about my approach to restaurants because they freaked out. I mean, I’ve been serving food my entire life, millions and millions of dollars, foie gras, Wagyu beef, caviar. I’d never seen anyone react to anything I served them like they did to that $2 hot dog.

Athletes go to the tapes when they’ve had a bad game to see what they did wrong. They don’t go to the tapes often enough when they’ve had a good game to see what they did right to make sure they keep on doing that thing. That’s how you take these little moments of organic brilliance that happen within a business and grab onto them and hold onto them and put systems behind them to make sure they become a part of the fabric of your organization. It almost breaks my heart to think about how many amazing things just kind of fluttered away because no one had the wherewithal to recognize that those were game-changing things they should grab onto. So I went to the tapes on that hot dog thinking, “What happened so that it could happen again, and what do we need to start doing as an organization in our culture to make sure it would start happening all the time?”

The first thing was that it required being present, which is kind of an overused kind of woo-woo thing these days, but I think it’s imperative in hospitality. For me, being present just means caring so much about the person you’re with that you stop caring about everything else you need to do. With our phones, with to-do lists, with the ever-increasing number of distractions in our lives, I think we have a real hard time slowing down for long enough to actually listen to the people around us and in doing so hear from them the things that will bring them the most joy. Had I been focused on efficiency at that moment, I would have, while I was clearing their plates, been looking around the dining room to figure out what table I needed to go to next and would’ve missed out on that opportunity. But instead I was present. So I picked up on that line about the hot dog.

Second, it required the notion of, hey, if you want to be the best in anything, you better take what you do seriously. Also, we all need to stop taking ourselves so seriously. Brands are very, very important, right? I’m sure there’s an awesome marketing team in this company that spends a ton of time thinking about your brand and justifiably so. That is your bumper sticker to the world. But far too often, the brand starts telling you whether or not you’re allowed to do certain things to make other people happy. And when that happens, the entire equation is out of whack. A hot dog in a four-star restaurant is sacrilegious, but look how it made them feel.

And then third, I mean this is one of the very definitions of unreasonable hospitality. Hospitality is about making people feel seen. And if that’s the case, the best way to do that is not to treat people like a commodity, but as unique individuals. I really believe I could have given that table the freaking bottle of vintage champagne and a Home Depot bucket full of caviar. It would not have had the same impact because it would not have been specific to them. Unreasonable hospitality is one size fits one. The greatest gestures are bespoke to the person receiving them.

And so the hot dog, that became our new true north, and in those three things we had a roadmap. Obviously change happens in a team huddle. So I got back into pre-meal and started talking to the team saying, “Hey, go out there and start finding opportunities of your own to bring these gestures to life. Be present. Don’t take yourselves too seriously. Find one-size-fits-one opportunities.” And let me acknowledge something there, I think and talk a lot about control versus creativity. Remember, this is a three Michelin star restaurant. I controlled a lot of what we did. Glasses needed to be placed so that the logo faced the guest, the silverware needed to be placed exactly... I don’t even know what this is called. For those of you listening, I’m pointing at the end of my thumb, that distance from the edge of the table, food served from this direction, cleared from this direction, tablecloths ironed, all this stuff, all these details that needed to be done consistently, perfectly.

Yet I’m also telling my team at that moment, “Go come up with whatever idea you want. I’m going to give you the permission and the resources to bring it to life.” So to that end, we added a position to the team, someone called the Dreamweaver named after the iconic song by Gary Wright. That person’s only role was to help everyone else in the team bring their ideas to life. And with the addition of that position and this newfound permission and resource-based pursuit, we were on fire. I mean, we talked earlier about some of the stuff we did, but we also did things that cost money.

A family of four from Spain was in the restaurant, parents and their children. We had these big windows overlooking the park and it started snowing. And we realized the kids had never seen real snow. Dreamweaver somehow found a store still open selling sleds, and when they left, there was an Uber SUV with the sleds in the back. They took them to Central Park for the best nightcap of all, a few hours of play in the freshly fallen snow.

Or we did things that were completely free. One time, a couple was dining with us and we learned they’d just gotten married at City Hall. They had a really big wedding planned, but the families fell out of love. There was some drama or something. This was now their wedding night. The server on her own committed herself to, over the few hours they were dining with us, figuring out what their wedding song was going to be, and we slowed down their meals so that they were the last people in the restaurant. When they were done, we brought them up into the private dining room, which was empty that night, and our team was having a party, their wedding reception. And when they walked in on cue, we put on “Lovely Day" by Bill Withers and we gave them the gift of their first dance.

We just did thousands of these things, which created this environment of electricity because yes, we were making the people dining with us feel real good, but in doing so, we were happier than we’d ever been at work because there is nothing more energizing than when you see the look on someone else’s face once they receive a gift you’re responsible for giving them. We all very quickly became addicted to that feeling.

Designing awe-filled experiences as a team

Chris: And I love that Dreamweaver is a formal position, but is this person on the floor at each service, listening? What’s a day in the life of a Dreamweaver?

Will: They’re on the floor every service. We had a team of them, but they’re not the ones coming up with the ideas. I mean, that’s the thing. I think I’ve seen a lot of people since this book came out. I’ve had a lot of people reach out to me saying, we’ve hired a Dreamweaver, we’ve hired Dreamweavers. Some of them have gotten it right, and other people haven’t, because what they do is they hire a Dreamweaver and they’re like, you’re in charge of coming up with the ideas. But that person can’t come up with the ideas. If you’re serving people, it’s the people who are serving those people who need to be empowered to come up with the ideas because they know those people better than anyone can. Better than you as the owner or the leader or the manager. And certainly better than one individual who’s meant to cover Dreamweaving on behalf of an entire company.

They’re there to execute the ideas of those on the frontline and make the ideas better. But if you delegate hospitality to an individual, not only is the hospitality going to be less curated and less appropriate and less thoughtful, but you’re also removing one of the most fundamental reasons why any organization should employ this approach. In my restaurant, the people in the dining room, the people who are actually responsible, when you go to a restaurant, your server has the most influence on whether it was a good meal or not. They have more influence than the owner or the manager. That’s your person.

And yet, in almost every restaurant, that person is just serving you plates of food that someone else created. If you double down on hospitality, you’re giving that person agency empowerment. You are now putting them in a position where they are imbuing the experience with their own creativity. You’re turning them from salespeople into product designers. And I have yet to meet a single individual who won’t give more of themselves to help something succeed than once they feel they have had a genuine hand in determining what that thing is.

Chris: So basically what you’re saying is that you created a culture of hospitality, delegating the ideation of that from this core idea of unreasonable hospitality. And then you kept doubling down on what that actually really meant and showed examples of what unreasonable hospitality meant and curated this idea that you then delegated, built into your culture, and delegated to everyone in the restaurant. And the Dreamweaver is in the delivery business. They’re not in the ideation business. They may have an idea, but the server is the one who sort of brings that to life, or somebody greeting other people at the table. It could be you, like you went to the table to clear some plates and you own the place.

Will: I mean, anyone could come up with the idea — a busboy, a food runner…the Dreamweaver still gets to be creative because you go and say, “Hey, this guy really loves, I don’t know, the movie “Sleepless in Seattle”. What can we do?” The Dreamweaver was like a thought partner and a creative partner to come up with something fun.

Chris: They can help evolve the idea into something they could actually do.

Will: Exactly. But they can’t be the person generating the seed of the idea because, here’s the deal. Danny Meyer would always say “Hospitality is a team sport. It doesn’t matter how hospitable any one individual is on the team, it’s the hospitality of the entire team that defines your success.” And that’s true, right? No one person can influence everyone in a dining room in the same way that no one person can influence every customer in any customer service organization. But I’ve found that a lot of people say, “Well, that’s all well and good, but my team doesn’t fully embody hospitality. And so we’re not ready to take that leap.” I found that the more trust you give people, the more trustworthy they become. The more responsibility you give people, the more responsible they become. The more you extend invitations to your team to come up with ways in which they can provide more gracious hospitality to their customers, the more hospitable they become. I really do believe it’s a self-perpetuating cycle.

Hiring the right person, rather than the best person

Chris: And that is what it means to build a culture. It’s something that if you get it rolling and it starts to produce the fruit you intended for it to produce, you can step away and sort of watch the machine work on something you built.

I like the idea you shared about the more you give someone responsibility, the more responsible they tend to become. Picking those people who are investible in that way, what are some of the traits you look for and say, “You know what? They belong here and I’m going to give them the responsibility.” What are the signals?

Will: What’s interesting is a lot of the people I looked up to when I was coming up in my career would say something to the effect of, you hire for hospitality and you train for excellence, almost implying that excellence is a muscle that can be strengthened, but hospitality is something you either have or you don’t. I very fundamentally disagree with that. I think hospitality is a muscle that can be strengthened too. And I think every single person I’ve ever met has the capacity for kindness, which means you also have the capacity to be hospitable.

Chris: That’s true.

Will: But sometimes you just need to know, well first, how good it feels to receive hospitality in order to be motivated to want to turn around and pay it forward. I have this thesis that if there was a law passed, or let’s say you and I took two weeks and stood outside of a DMV somewhere in America and said to everyone who went to walk into the DMV, “Hey, I’ll give you a hundred bucks if you are really, really nice to everyone who works in there.” I bet a couple weeks later that DMV would start to feel like a pretty warm and fuzzy place. But of course, the people at the DMV are most often rude and known for being rude because no one’s nice to them.

Chris: Not at all.

Will: Hospitality is a virtuous cycle. You can’t be expected to be nice if no one’s nice to you. Now in a business, you get to prime the pump as the leader by being nice to those people, even if their customers aren’t yet nice to them in return. Then if you are nice to your people and they start to lead with generosity and kindness with the customers, then it starts to come back to them. So I believe it’s not about hiring for hospitality and training for excellence. I just think you hire people you feel a connection to and then train them and encourage them how to excel at both.

I’ll use this as a metaphor. I have a really good friend. She is 35 years old. She is beautiful, smart, creative and funny, and she wants to get married. She really wants to have kids and she is still single because she has this really long list of every single box her potential partner needs to check. I think based on the length of that list, there might be like four people in the world who would check all of them. I think we do that as we try to hire often as well. I think people, when they list requirements from an experiential perspective or a credential perspective, put so many things on those lists that they end up weeding out, filtering out some of the people who could have been perfect for that job. And by the way, in doing so, are selling themselves short as leaders, because if you are as good a leader as many people believe themselves to be, you should be able to teach or train half of the things you’re putting on that list if you have the right person who wants to learn on the receiving end of your education.

So when I am looking to hire someone, I make the list of what I need them to come pre-equipped with as short as humanly possible based on the position. Then I just sit down with them and try to get to know them. Are they passionate? Do I think they can be really hardworking? Do I trust them? And most importantly, do I want to spend time with them? And will my team want to spend time with them? If those things are all correct, then I believe we can work together.

I was in Wyoming with a group of people a couple months ago, and one of the guys who was there was a British guy named Angus who rows in oceans. So he puts together teams of four people. They get in a boat and they row across an ocean, and it’s intense. This takes 60, 70, 80 days. They row for two hours, sleep for two hours, row for two hours, sleep, I mean, this is over months. It’s insane. This is one of my favorite questions to ask someone if I meet someone who does something dramatically different than I do. I say, “Hey man, if I wanted to start rowing oceans, what’s the biggest lesson you’d teach me or you’d give me?” And he said, “Pick the right team, not the best team.”

This whole thing is he starts to put a team together 18 months before they start rowing. He said, “I can get anyone in shape in 18 months and I can teach anyone how to row, but the chemistry that exists within the four of us will either make or break us.” He told the story about how they had a race with a bunch of different people, and one of the other teams was the American team. The Americans had a ton of sponsorship and they put together the most badass group of guys with crazy experience, and he was operating on a shoestring budget and just got a few of his friends and trained them for a couple years, and they beat the Americans by 30 days because 20 days into the row, the Americans started fighting because they all had such big egos and their whole thing fell apart. So I guess the really short way in which I could have answered your question is, how do I hire? I try to pick the right people, not the best people.

Chris: So let’s wipe the slate clean. You’re doing a very new business. What is the first hire you would make? Let’s say you’re going to do Eleven Madison Park again because it has a lot of really good food, let’s just be real. But let’s say you’re wiping the slate clean. What’s sort of your first hire? And imagine you’re in the shoes of a totally new startup entrepreneur trying to break into the scene. What’s your first hire?

Will: Well, when possible, the advice I would give people is to forget about what position you’re trying to hire for and first look deep into your community and figure out who is the right person you want to start with. Listen, depending on the company, you can start with someone in operations, someone in brand, someone in marketing, someone in finance. But man, you say, wipe the slate clean. If I ever am in a position where the slate has been wiped completely clean, I’ve messed up badly.

Chris: Yeah.

Will: Seriously. And I mean that from a human capital perspective. That doesn’t mean wiping the slate clean in one part, like OK, you sell a company and you start a new one. Wiping the slate clean in another sense of the word means you are no longer connected to any one of the people with whom you have a relationship with, and you’re starting with a bunch of strangers. If you’ve done that, you’ve made a bunch of mistakes. Because when you’ve worked with people for any sort of extended period of time, you have an established shorthand. They know you, you know them, you know one another’s strengths and weaknesses, and therefore have the ability to leverage those in each other. So I would just look around and think, “Who have I worked with in the past? Who do I trust? Who do I enjoy time with the most, who could be passionate about this idea in the same way I am?” Start with that person.

Chris: Yeah.

Will: Because man, I don’t care how good you are at being alone, when you start something, it just sucks and it’s lonely and you will be less effective. And finding someone — whether or not it’s a partner in the ownership sense of the word is irrelevant, but find one of your people. That’s the best advice I’d give.

Managing expenses with the 95/5 rule

Chris: That’s good. Well, one of the things I definitely wanted to make space for is for you to talk to us about the 95/5 Rule.

Will: So the 95/5 Rule is the way I have managed my businesses over the years, which is that I manage every expense like a freaking maniac 95% of the time. And when I say a freaking maniac, I mean there is no expense too small to be pored over in the most excruciating of ways. I’ll give you an example—

Chris: You have a knack for an attention to detail, let’s just say.

Will: I do. Well, and by the way, I actually have fun in the creative pursuit of managing expenses, which is one thing people in my industry certainly struggle with at times. They love the creative process of what plates to use and the colors in the room and how to build a wine list and a cocktail list, but they don’t derive the same amount of pleasure and the creative process of optimizing profitability. I think with just a simple shift in perspective, well, all of those things are creative. Why not find the joy in all of them? Which, by the way, what’s the point of doing anything if you’re not bringing some profit to the bottom line?

Chris: Yeah, so true.

Will: And in my world, OK, I’ll just have people over for dinner if it’s not going to be profitable. But I’ll give you an example. In a fine dining restaurant, there can never be a fingerprint on the rim of the plate. So we have these little rolls of paper towels that are dipped in water and vinegar that you wipe the plate with right before it goes out just to make sure as the cooks were finishing it, there’s not a fingerprint on it. We would cut those paper towels in half because the size of a normal paper towel was more than we needed, and it just felt like a waste to spend two pennies on each one of them instead of one penny. The cumulative effect of that change is ridiculous. But I believe if you care about managing expenses, you need to care about all of them. So 95% of the time, we’re like maniacs, which earns you the right to 5% of the time to spend “foolishly”.

And I just did air quotes for those of you who can’t see me because I actually believe that “foolish” spending is not foolish at all. That is the spending that creates the kind of loyalty that preserves, protects and ultimately grows your business. And for us, the foolish spending would’ve been the Dreamweavers and the sleds or for our team. We were really, really disciplined about minimizing expenses over time and things like that, the normal things a company should do in running a business. Yet we would throw staff parties that cost an absurd amount of money because that would be the thing people would remember. One of the ways I talk about it is if you are evenly distributing your focus on expenses, you’re going to have an efficient but completely unmemorable business. Whereas if you’re a little more aggressive in how you manage the expenses 95% of the time and just blow it out the last 5%, that is how you actually leave a lasting impression that results in the kind of memories people will never forget.

Chris: There’s something to that, right? Someone on the receiving end of an expense cut could be frustrated by it like, “Man, it’s just more cutting or things like that.” But for some reason in the culture you’ve built and tend to foster, they can live in that and participate in that because they know you are saving for an investment either in your people and the employees and experience they’re having or the experiences your customers enjoy. It isn’t just going into your wallet.

Will: Yeah, exactly. And by the way, it needs to be both. You can’t do all of it and only reinvest in the customers because, well, then the employees are like, “What do I get out of this?” It’s also less scalable, because if you don’t show the people on your team the kind of hospitality you want them to be showing to others, you’re ultimately going to be setting yourself back.

Imagining how AI could support — not replace, restaurant employees

Chris: That’s good. Well, we’ve talked about a lot of stuff, and I would say if Danny Meyer’s enlightened hospitality is your floor and let’s say your ceiling is unreasonable hospitality, what’s sort of the next generation’s version of hospitality ? What is the evolution, man?

Will: Gosh, that’s a big question.

Chris: I told Christina [Tosi] this morning, I have one question for Will. I told her, and she said, “Ooh, that’s good.”

Will: I mean, I don’t know about the next generation’s thing. This is what I’m thinking about a lot right now. And it sounds so cliche and trite, but I’m actually so... There are very few things that simultaneously terrify me and excite me beyond articulation, but that is AI and how it applies to hospitality and customer service.

Chris: Ooh.

Will: Because I think AI has the capacity to supercharge hospitality in the most beautiful of ways. I think if harnessed in the right way, AI can be the thing that takes all those things I did at a three Michelin star number one restaurant in the world and make them scalable to the point where we can start experiencing that sense of feeling so much more often in our day-to-day lives. But it completely hinges on the way it’s used because I think some companies will use it... and I’m not talking about being terrified by sci-fi AI stuff — that’s not where I’m going. But I’m talking about the fact that some companies will use AI to give humans the tools to be even more human, and some companies will use AI to replace their humans. I’m terrified of the second one, and I’m so excited to see how unbelievably connective and human we can be if we have this new tool in our toolbox.

Chris: I mean, you think about culture as a machine. Like what you’re putting into it has this outcome and output that only it can do. It’s the same thing with AI. If you feed it and train it and develop the culture or the idea or the value system, things like that, it will be able to produce things and it will sort of augment all of what we’re capable of thinking.

Will: I mean, imagine if I could be the one that trained the AI that interacted with you, when you call Verizon and are put on hold. I mean, that is a game changer. And so, man, I’m excited to embrace that and try to inform it and see where it goes from here. So enlightened hospitality to unreasonable hospitality, my answer is not actually the next step there. I haven’t figured it out yet. I’ll send you the book when I have figured it out, but the AI thing is in a world where there’s a lot of people talking about how the world is over, but I believe there is a beautiful shining light of opportunity and optimism that I think will come from it.

Rapid-fire questions

Chris: So good. I’ve asked you a lot of questions, but I have a couple of rapid-fire questions that I just have to know. Then we have a whole special set of questions we’re going to ask you with Christina here in just a second.

So here we go. Outside of New York, what’s your favorite eater’s destination?

Will: My favorite eater’s destination outside of New York is a restaurant in Seattle called Canlis, a third-generation, family-run restaurant. That is the only restaurant I know of in America that has that much history and yet is still so relevant.

Chris: All right, best New York song — is it “New York State of Mind" by Billy Joel, “No Sleep Till Brooklyn” by The Beastie Boys, or something else?

Will: Billy Joel.

Chris: OK. If you could have dinner with any historical figure, who would it be?

Will: Oh, Golly. Elvis.

Chris: Who cooks more at home? You or Christina?

Will: Definitely Christina.

Chris: Oh, I mean, she’s on—

Will: I mean, that makes sense.

Chris: She’s on Instagram a lot, cooking and baking. What’s your favorite non-sweet meal Christina makes?

Will: Oh, my favorite non-sweet... She makes this, it’s like one of our comfort dishes. She’ll do this roast chicken and this orzo with mushrooms and this creamy chicken stock kind of thing, and it’s just perfection.

Chris: You guys are lucky. Let’s just be real. What New York City street fare do you crave?

Will: Street fare, I mean, I do like a hot dog, but also just one of those rice and meat dishes from a halal cart. I think it is one of life’s great pleasures.

Chris: Yeah. I would agree with that. What’s the last book you read that you just couldn’t put down?

Will: I’m in the midst of reading “The Creative Act” by Rick Rubin, and it is good.

Chris: His stuff has been awesome recently.

Will: He’s just crushing it and just the first page, I mean, I always talk about in our conversation before how there are people who say, “I’m not that creative.” And I think it’s just utter BS, like everyone is creative and he articulates it in such a cool way at the beginning of the book. If you’ve ever just come up with a new way to get home, you’re creative. Everyone is creative and we all actually are exhibiting our inner and our own creativity on a daily basis. We’ve just been trained to think that creativity is only when you write a song or make a movie or paint a painting.

There’s a quote Maya Angelou said — I think I might get this a little wrong, but it’s something like, “The more creative you are, the more creative you become." And you can’t become creative unless you start being creative. And Rick Rubin writing that we are all already expressing creativity on a daily basis, I feel like is a really good shortcut to getting where we all have the ability to go.

Chris: Yeah, I love that. “If you’ve ever found a new way home, you’re creative.” I also like to say, “Resourcefulness is the businessman’s creativity.” I mean, it’s true, it’s—

Will: I love that.

Chris: Figuring this stuff out. Finding a way.

Will: For sure.

Chris: I think that’s really good. All right, last question. If your story were turned into a movie, what would be the title?

Will: “Christina Tosi’s Husband”.

Chris: Baking, yet not baking. I love that. Hey, well it was awesome to sit down and have this conversation with you. You are beautifully articulate, inspiring, more than maybe you give yourself credit for. It was awesome to sit and talk with you and I hope everybody listening has found a way to take the hospitality context you’re using to find it in their own context so that they can do something remarkable with their work. I really appreciate you coming.

Will: Thank you, brother.

Chris: Absolutely. Until next time.