Should You Work With Your Friends? with my friend Will Guidara

0:00Here's a question I'm supposed to ask you. I can't even read it with a straight face should you do business with your friends or should you not mix the two the reason Will and I are laughing is because we're talking about doing a business together and we had a huge fight about it before we got on the podcast and now we're asking should we even be doing this if you've been listening to this podcast you'll know that friendship is at the top of my mind lately We trust our friends. We can rely on our friends. These are essential attributes for co-workers as well. So do friends make good co-workers?

0:41I invited my friend and occasional co-worker, Will Gadara, to talk about if it's a good idea or not for us to actually work together. Will is the author of the New York Times bestselling book, Unreasonable Hospitality. He's also a producer and writer on the last season of the Emmy-winning show, The Bear. And prior to that, he was the co-owner of Eleven Madison Park, which at one point was named the best restaurant in the world. But above all, he's my friend. This is a bit of optimism.

1:17Having you on the podcast is like cheating.

1:22Because you're one of my male friends that I say I love you to. you know and the love i have for you is real and permanent and the reason i say having you on the podcast is cheating is because i feel like it's too easy like i i can talk to you forever i always learn something from you you always make me laugh and my friendship with you means more to me than many things dude the feeling is mutual by the way the last two things I always learn something from you as well. When I'm wrestling through a new idea, you're one of my favorite people in the world to talk to about that idea because I was in the conversation understanding it more clearly than I did at the beginning.

2:10And there are very few people in the world that I laugh like a third grader when I'm around. You know, one of my favorite things about us is when we fight, we find a reason to make a joke. And the only reason I know this is because five minutes before this podcast, you and I were on the phone having a fight that ended up us hiring to apologize to each other because we had to get on the podcast. But the thing that I found so enjoyable is not only do we want to get to resolution when we fight because we don't want to hurt each other and we don't want to be the person that hurts the other. We really like it.

2:53It hurts me more that I hurt you than you were hurt. You know, but if the opportunity to make a joke arises, even if the situation is not does not call for it, we cannot resist. We have to make the joke. It's like game off, game off, joke, joke, joke, joke, joke. All right. Came back on. So I really need to tell you about how you made me feel. Exactly. It's like serious, serious, not serious, serious, serious again. Exactly. You are one of the most talented people I know. And my favorite thing about what's happening to your life is that you were a famous restaurateur, I guess you still are a famous restaurateur, who your career has made an unexpected turn where you probably will never own a restaurant again, if I had to guess.

3:34And you are now a guru, a thought leader teaching us how hospitality works, but more importantly, how to treat people, which is what ultimately hospitality is. Did you think you were going to be a restaurateur owning restaurants for the rest of your life? Or did you always kind of know that your career had a second act? Had you talked to me five years ago? Is it five years, six years now? I would have told you that I will always live in New York City and I will always own and operate restaurants in New York City. And then I had a falling out with my business partner. We fell out of love. and after some time it became clear that splitting the company and the process of figuring out how to split it was well in essence tearing apart the very thing we'd spent all that time building and in a revelation like a cinematic style revelation one day i was like no the best thing for me to do is sell him everything that happened to be two months before COVID that I signed on the dotted line, the contract to sell.

4:41Woke up a few days later, after a few days of some celebration, right? I sold a company, that's a big deal, with a full-on identity crisis. Who am I? Who is a restaurateur without any restaurants? And frantically, aggressively started raising money and putting together a team and going out to sign leases. And literally COVID started one week before I was set to sign three restaurants and an office leases in New York City. Then I went up to the country, to our house up there for what I thought was going to be a few weeks, right? Like all of us did in that moment. A few weeks turned into a few months.

5:22I was kind of keeping all those deals warm. And then one day I decided to just stop. Because I think for many people, COVID gave us, in spite of the loss of life and financial suffering and loneliness and isolation, most people that I know of can point to one thing that they consider to be a gift that COVID gave them, a shifting of perspective. And for me, it gave me the gift of just stopping. and rather than running back to do what i'd always done it gave me the gift of taking the time to decide what i wanted to do next and that's when i reached out to you and the idea of unreasonable hospitality was born and i i wanted to write the book because well we'd been talking about it for a while and now i finally had time and space to focus on it but for two important reasons.

6:19A, I think one of the best ways to learn is to teach. And I figured if I could spend really intentional time putting words to the things I really believed in, it would make me better at embodying those things and whatever my next chapter ended up being. But also I figured through walking down the road I'd just been on anew, it would give me clarity and what I wanted to do next. I didn't know that the book was going to be the beginning of what I wanted to do next. It is not a new idea to say that too many people intertwine their identities into their professions. You said it. What is a restaurateur without a restaurant?

7:00Like my identity is a restaurateur or a lawyer or a doctor or whatever your chosen profession is, a true career if you're no longer that thing. I know the CEO. He was the CEO of a big media company and he left his job and there was some big fancy Hollywood party and he wasn't invited. And a friend of his happened to be over at his house that day and be like, hey, did you get your invitation to the party? And his friend goes, yeah, of course. And he goes, I didn't get mine. I wonder, maybe it just got lost. It never occurred to him that he was, for all his years of going to that party, they were never inviting him.

7:36They were inviting the CEO of the company. And he's no longer the CEO and the invitation will go to the next CEO. It never occurred to him. And because his identity was so intertwined with being the CEO of the company, he couldn't understand those two were not the same thing. But the reason I bring this up is not because that's a new thought, but the idea that a friendship, that a partner, a work marriage, the identity of that relationship is intertwined with the business. Yeah. I guess the thought I'm trying to get out is like, is that healthy? You know, because I've gone into business with friends where things worked.

8:19I've gone into business with friends where things didn't work. And I've gone into business with friends where it absolutely destroyed the friendship, whether it was successful or not. And I've gone in the other direction where it had no impact on the friendship. Maybe the friendship even got better, whether it worked or not. So is it conditional on the friendship? Were you friends first and then went into business together or did the friendship form in the relationship, in the business? The friendship formed in the business. We worked together first. Okay. I mean, man, I don't know that there's one right answer to this.

8:51Because I think this question comes up a lot, which is should I go into business with my friend? I mean, what is going into business with a friend actually mean? It's effectively signing an agreement to commit yourselves to one another and help grow an idea together, which, by the way, is not dissimilar to marriage. Yes, and? Well, I mean, I'll play it out just for argument's sake. Ideally, you're friends with the person that you marry in addition to being lovers. And then one day you decide to get married and you're signing an agreement to commit yourself to them and them to you. And in many cases, then you have a child and you are committing to growing that idea together.

9:41I know a lot of people who started businesses with friends because either the friend just happened to be there. I've seen a couple of those. I know plenty of marriages that have started that way too. You know, the lucky roommates club kind of thing. and a friend you trust and who wants to build it with you. But I've also had this conversation with people, which is if you truly want a business to succeed, sometimes you have to get used to the idea that you may have to fire your friend. Yeah, I mean, when does it succeed versus when does it fail and not to continue? Well, it's not a question of the business succeeding and fail, but sometimes that friend Peter principles out.

10:15Like they were hugely valuable emotionally and skillset from zero to one, but don't have the skill set to go from one plus. Yeah. And so this is the dirty truth about business, which we don't talk about. But sometimes you do have to fire your friends. Sometimes you have to, or sometimes you stop choosing one another, right? In the same way, like you hear this marriage principle all the time. And the secret to a healthy marriage is to wake up every single day and choose that person. And it's an active choice, right? It's not a passive thing. You re-engage in the relationship every single day. And I think, listen, friendships in business, they end for different reasons and in different seasons.

11:07But sometimes it's because one person has outstayed their value. you, sometimes it's because they no longer are prioritizing one another to the point that they're willing to fight through what is necessary to make it work. You and I do something that I think most friendships don't, which is there is a brutal honesty, not about the other, although that happens too.

11:31Emphasis on the brutal. There's a brutal honesty about ourselves. And you and I, in a moment of tension where one of us is digging in for some reason or another, the other person will ask, is this your ego? And the default answer for anybody else being asked that question is no, even if it's yes. What I think is the lesson here is when one of us says to the other, is this what you actually feel or is this your ego? And the other person will say, it's my ego. There's a vulnerability, even in extreme tension. I guess where I'm getting at is like, how did we learn that? Have you always been that honest about yourself?

12:14How did you learn that? Because you and I will say, it's my ego, and we'll back away from the argument. I mean, in the conversation we just had, I think that came up twice. In one case, the answer was yes. In the other case, the answer was no. Right? About two separate things. Two separate things yeah i i think that okay a ideally as you get older and you become more self-assured you're able to actually say gosh you're right this is about my ego and this is not rooted in the right place without fearing that you will lose the other person's respect for having made that mistake you're confident enough in yourself to make a mistake and admit to having made one.

12:55But I'd also say, okay, going into the phone call we just had, we both, whether it was an active thing today or it's invariably an active thing generally, have made the choice that we are going to hold on to one another. We are friends and we're not going to let, like I will not let you go and I know that you're not going to let me go. No. And so in a moment where if you say, is that your ego? If I lie, now there's a rupture in our friendship that's going to be hard to repair. And it's just the older you get, the smarter you get, I think, more often than not. And it's easy to just make the choice.

13:34I care enough about this person to do what I need to do in order to preserve and pursue this friendship. Confidence. You have the confidence to admit your own failings. And the question I'm asking myself is what comes first, the confidence to be vulnerable or the skill of being vulnerable that leads to confidence. And I'm just thinking about my own experience. I don't think I worked on my self-confidence in order to be vulnerable. I think I took the excruciating risks to be vulnerable and it ended up helping me build my confidence. Yeah, I think I'd agree with that. I mean, you could argue in one sense, one begets the other, but there are plenty of people that become more confident that never become more vulnerable, but more often than not, vulnerability leads to confidence.

14:23And I think it's unfair. I think it's unfair to human beings to say, ah, in order to have successful, vulnerable relationships, friendship, business, marriage, first you have to work on your confidence. Because at the end of the day, the thing that makes us fall in love with each other is the fact that we can be insecure and we can be, like nobody is purely confident. We all have insecurities and anxieties. And sometimes it's because they're deep seated And sometimes it's because I had a bad night's sleep. They come and go. I've been thinking about this a lot lately, which is how we present ourselves to the world versus how we present ourselves to our partners.

14:56Business partners, close friends, romantic partners, like however you want to define that. In private, intimate spaces, right? And there's much talk, especially on social media, about living your true self out loud, right? Whatever that means. And I'm not sure that's 100 % true. I don't think you should lie to the world. I don't think you should present yourself as something you're not. However, we have to bend and mold ourselves, code switch for the situations that we're in, in order for society to function, right? I like sitting down in a chair and being comfortable. This is me, right? I can't do that if I'm having a first meeting with somebody.

15:43It's disrespectful. Yes. I like putting my feet up on a desk. I can't do that if I'm interviewing for a job. And if somebody says, why are you putting your feet on my desk? You're like, just being myself, just being my true authentic self. You don't get to say that. Like we make different jokes depending on the company we're in. We have different levels of formality depending on the company we're in. We push back differently depending on the company we're in. In other words, if we were all just ourselves all the time, every stable institution would just society would stop working. So because we're never truly, truly, truly our full selves in public, because it's not you can't really be you.

16:25We balance the line. We sort of we play the teeter totter of being myself, but also being socially being a functional member of a civilized society. it's those intimate relationships when I'm in private that all of the society's expectations can be ripped away. And those places I can be my true authentic self. And if you have intimate relationships where you cannot be your true authentic self, that is where confidence starts to flail. You have to have some place you can do that. You're playing a public persona in a private relationship, that is where the moist air of bacteria grows. The bacteria of insecurity.

17:05I want to add just another layer to this though, because here's the thing. Yes, I'm not going to curse in front of kids. I will curse in front of you. I will not curse more likely than not on this podcast, but if you and I were having a drink, I'd probably let a few curse words fly. Exactly. The thing is though, these are all actions. How my posture in the chair, whether I kick my feet up, whether I curse, all this stuff. I do think we can be consistently ourselves when it comes to principles. And I know that whether you are on stage in front of 10 ,000 people or whether you and I are having a pizza in your living room, your principles are going to be the same.

17:48You're going to live with integrity. You're going to hold yourself to a certain standard of accountability. You are going to lead with vulnerability. And this doesn't change what you said but what i do think it means like as it pertains to where this started with vulnerability and its relationship to confidence i mean listen relationships are relationships the lessons we learn from those in life apply to those in work and vice versa and the most confident leaders are the ones that are vulnerable with the people on their team the longest marriages are those where one person is vulnerable enough to tell the other person how they made them feel and how they were hurt by something completely unintended.

18:29And the same applies in friendship. And chicken or the egg on this one is, do you stop being vulnerable because you're not confident or you tried being vulnerable with the wrong person, like you took the wrong risk? That's it. And the number of friends that I and you both have who are never vulnerable in relationships because they tried that and it got thrown in their face. And by the way, now they live in insecurity in their relationships. And that's when they start living their public persona in their private lives. And that's when they start living their public persona privately. And so I think I'm going to go back to what I said some moments ago, which was a thought.

19:08But I think I'm going to double down on that thought, which is we have to take the risks to put ourselves out there in intimate situations, being at a business partner, friendship, or a romantic partner. And the times where not only does it not backfire, it actually contributes to the relationship. It becomes easier to take those risks and you become more confident in saying, I screwed up or that's my fault or I don't mean to be an asshole. It's my ego that's getting hurt. Yeah. And those conversations become a lot easier. Like I think 10 years ago, if you said, is it your ego? I would have said no when it was.

19:52And by the way, your ego would have then. Maybe even five years ago. Probably yell at me for even asking the question and the relationship would have really. Yeah. There's a rule we have at work that I absolutely love. And it's incredibly true, which is if the response is above a five. it's about something else. Gosh, I love that. We use it at work, but it's really true in any, like if your spouse yells at you for not putting the cap on the toothpaste, I've told you a hundred times. It's not about the toothpaste. It's not about the toothpaste. And the problem is, is we don't listen to the volume.

20:29We listen to the words. And then we get defensive. It's like, what's the big deal? It's just the cap on the toothpaste. So you put it on, who cares? Nothing's happening, right? And a fight ensues, as opposed to saying to ourselves, this is not about the toothpaste. Yeah. And then, by the way, having the courage to say, I feel like there's something more at play. Can we talk about it? Your job is to listen to their story and to learn to respond with curiosity. Tell me how you feel. Why do you think you feel that way? Is that really true? I understand the example you gave me. Can you give me more examples to help me understand where I'm failing you?

21:07The example thing is so interesting because sometimes when I'm in a tense moment in a relationship, I'll say that, hey, can you give me examples? And the response is, we don't need to rehash it. I'm like, no, I'm not trying to rehash it, but I would like to understand what I am doing inadvertently to make you feel that way such that I can be better at not doing it. The examples have to be specific. They have to be very specific because sometimes it's a simple word and sometimes you need to trace all the way back to it to realize, A, the whole thing is misplaced, or be, gosh, there is this little thing that I do that is totally grating on this person.

21:44And it's so easy for me to stop doing it. And the impact is profound if I can. Okay, what do people not understand about friendship breakups?

22:00Oh man, what do people not understand about friendship breakups? It's so big, that question. It's such a big question. I'm so glad you have to answer it and not me. Also, posited in the negative. I know. I think that people are much lazier and more passive in friendship breakups than they are in romantic relationship breakups. and in being so are undermining the unbelievable importance of valuable friendships in our lives. And we've talked about this all the time, how with everything that exists out there about being a good leader, a good dad, a good husband, wife, whatever, we don't talk about friendship nearly enough, And yet that is the one that actually energizes you and sets you up for success in all the other relationships.

23:06And we are so much less intentional in our pursuit of those friendships. And intention at the end of something is just as, if not more important than intention at the beginning of something. I mean, you think about some of the closest friends you have in your life. When you think about vulnerability and the things you've experienced with them and the things you've told them. the things about you that only they know and yet they just drift away. Imagine if that was the case in a marriage. You're like, one day you're just not married and you don't even know what happened. It's a bizarrely counterintuitive thing.

23:42I think you're right. I think what people do not understand about friendship breakup is they require the same level of effort and stress and courage as breaking up with a business partner or breaking up with a marriage. They require effort. The only difference between our closest friendships and our business partnerships and our marriages is there's no contract. And so we go through the excruciating pain of ending those relationships because we have to unwind a contract. There's no unwinding a contract in a friendship. And so we can get away with being lazy or avoidant. And by the way, actually addressing it, even if it is the end of the road for a friendship, is not only an act of generosity to them, but towards yourself as well.

24:28Yeah. And I think that there's a courage that comes from leaning into it and say, I think we're growing apart. And I think we're both showing up. I think we're just, I think we're playing roles. I think we're both playing the role of friends. But let's be honest, I can't be unhappy in this friendship, and you're really happy in this friendship. there's no way that our feelings are completely opposite so if i'm feeling this unsatisfied and this unhappy i have to believe that you're somewhere around close to that feeling as well and by the way sometimes like intentionally going to end a friendship is the best way to save it i've tried so many times to end my friendship with you and i just end up closer and closer no but one of my best friends for this like 10 years ago we'd known each other since college I was just feeling under invested in with the friendship and I was giving a lot more to it than I was receiving out of it and one day I called him I was like hey I'm investing too much into this friendship and not getting nearly enough back from you and if that's your way of telling me that you're busy your life has moved on that I think we're closer than you think we are then great but can we just have that conversation so I know where we stand and And he just needed to hear that.

25:43And he's like, oh my gosh, you're right. No, this is an important friendship to me. And he, to this day, is still one of my closest friends in the world. Well, this is my big complaint about how we treat friendships or how we treat friends rather, right? Which is most of us think we're good friends and most of us are actually pretty bad. And the example that I often give is, would you cancel on a meeting for a friend or would you cancel on a friend for a meeting? Oh, but my friend will understand, you know? And to your point, which is we get lazy with our friends or ignore our friends who don't call our friends because, quote unquote, they'll understand.

26:15And it's really quite dismissive to assume that somebody's fine with bad behavior. Yeah. Or dismissive behavior or being deprioritized constantly. Occasionally it's acceptable, but constantly it's not acceptable. And I'm guilty of it. But there's one friend I'm thinking of right now, which is I'm so guilty of deprioritizing her all the time. And the reason is, is because she lets me. And the reason is, I mean, I'm an asshole for doing it, but she's constantly like, don't worry about it. It's okay. I understand. And it occurred and she never said anything to me, but she's constantly showing up as a good friend.

26:55And it got to the point where it was so unbalanced that I felt like such an asshole. Yeah. Because she kept showing up for me when I needed it most, and I kept failing. And I had to have a hard conversation with myself that you better up your game because you do not deserve the friendship that you're getting. Yeah, or stop taking. Or stop taking, yeah. And it's not a behavior. That amount of dismissiveness is much less prevalent in marriage or in work. And you can say the same thing. have you ever canceled a date with your wife or a friend back and forth or taking care of your kids in a friendship i'm not saying you should like you can't get away with it you can't get away with it the friends i think it's one of the reasons so many of us are actually worse friends than we think we are is because we can be i think friendships allow us to get away with things that to your point marriages and business relationships that just there's just no room for it for whatever reason the institution just doesn't allow for it i don't think it's possible to live a life worth living if you don't have a group of friends that you pursue constantly, that you love, that you trust, that you will do anything for.