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

They say business and pleasure don’t mix. But what about business and friends? My dear friend Will Guidara is the perfect person to dive into this question because we're actively trying to get into business together. And, let's just say, it requires a lot of effort. In addition to being someone I love, Will is a renowned restaurateur, known for owning and operating Eleven Madison Park, once named the best restaurant in the world. He’s also the author of the brilliant book Unreasonable Hospitality and a co-producer of the FX television series The Bear. Will and I have worked together before, so I was excited to chat with him about turning friends into colleagues, the reality of friendship breakups at work, and why sometimes showing respect means we have to change the way we treat a friend. This…is A Bit of Optimism For more on Will and his work, check out: Unreasonable Hospitality The Art of Creating Fiercely Loyal Customers

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Simon Sinek?

  Here's a question I'm supposed to ask you.

• 0:04Simon Sinek?

  I can't even read it with a straight face. Should you do business with your friends? Or should you not mix the two?

• 0:12Simon Sinek?

  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?

• 0:25Simon Sinek?

  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 coworkers as well. So do friends make good coworkers? I invited my friend and occasional coworker, Will Gadera, 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.

• 1:11Simon Sinek?

  This is a bit of optimism.

• 1:17Simon Sinek?

  Having you on the podcast is like cheating.

• 1:22Simon Sinek?

  Because 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 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.

• 1:53Speaker 01

  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. And there are very few people in the world that I laugh like a third grader when I'm around.

• 2:18Simon Sinek?

  You know, one of my favorite things about us is when we fight, we find a reason to make a joke.

• 2:28Simon Sinek?

  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 as 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. It 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.

• 3:06Speaker 01

  It's like game off, game off, joke, joke, joke, joke, joke. All right, game back on. So I really need to tell you about how you made me feel.

• 3:12Simon Sinek?

  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. And 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?

• 3:53Speaker 01

  Had you talked to me five years ago?

• 3:56Speaker 01

  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.

• 4:06Speaker 01

  And then I had a falling out with my business partner. We fell out of love.

• 4:12Speaker 01

  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.

• 4:26Speaker 01

  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. Woke up a few days later.

• 4:45Speaker 01

  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.

• 5:21Speaker 01

  A few weeks turned into a few months. I 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

• 5:36Speaker 01

  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.

• 5:54Speaker 01

  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.

• 6:02Speaker 01

  And that's when I reached out to you and the idea of unreasonable hospitality was born.

• 6:09Speaker 01

  And 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.

• 6:20Speaker 01

  A, 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 a new, it would give me clarity in 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.

• 6:51Simon Sinek?

  It is not a new, 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? Like, 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, 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.

• 7:36Simon Sinek?

  They were inviting the CEO of the company.

• 7:38Speaker 01

  Yeah.

• 7:38Simon Sinek?

  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 the two were not the same thing. But the, the reason I, I bring this up is not because that's a new thought, but the idea that a friendship, that a partner, a, a work marriage, the identity of that relationship is intertwined with the business.

• 8:09Speaker 01

  Yeah.

• 8:10Simon Sinek?

  I guess the thought I'm trying to get out is like,

• 8:13Simon Sinek?

  Is that healthy? You know,

• 8:16Simon Sinek?

  because I've I've gone into business with friends where things worked. I've gone to 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?

• 8:42Speaker 01

  The friendship formed in the business. We worked together first.

• 8:46Simon Sinek?

  Okay.

• 8:47Speaker 01

  I mean, man, I don't know that there's one right answer to this.

• 8:51Simon Sinek?

  Because I think this question comes up a lot, which is, should I go into business with my friend?

• 8:57Speaker 01

  I mean, what is going into business with a friend actually mean? It's 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.

• 9:15Simon Sinek?

  Yes, and?

• 9:16Speaker 01

  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.

• 9:41Simon Sinek?

  I know a lot of people who started businesses with friends because either the friend just happened to be there.

• 9:47Simon Sinek?

  I've seen a couple of those.

• 9:48Speaker 01

  I know plenty of marriages that have started that way, too.

• 9:52Simon Sinek?

  You know, the lucky roommates club kind of thing. And you know, a friend you trust and who wants to build it with you. But I've 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.

• 10:08Speaker 01

  Yeah, I mean, when does it succeed versus when does it fail and not to continue?

• 10:11Simon Sinek?

  Well, it's not a question of the business succeeding or fail, but sometimes that friend peter principles out. Like, they were hugely valuable emotionally and skill set from zero to one, but don't have the skill set to go from one plus.

• 10:25Speaker 01

  Yeah.

• 10:26Simon Sinek?

  And so this is the dirty truth about business, which we don't talk about. But but sometimes you do have to fire your friends.

• 10:39Speaker 01

  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.

• 10:49Speaker 01

  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. But sometimes it's because one person has outstayed their, their value. 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.

• 11:20Simon Sinek?

  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.

• 11:31Simon Sinek?

  Emphasis on the brutal. There's a brutal honesty about ourselves. And you and I, in a moment of tension where we're, 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? How did you learn that?

• 12:17Simon Sinek?

  Cause you and I will say, it's my ego and we'll back away from the argument.

• 12:21Speaker 01

  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.

• 12:29Simon Sinek?

  Two separate things, yeah.

• 12:30Speaker 01

  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, you're confident enough in yourself to make a mistake and admit to having made one. But I'd also say.

• 12:58Speaker 01

  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 gonna hold on to one another. We are friends and we're not gonna let, like, I will not let you go and I know that you're not gonna let me go.

• 13:16Simon Sinek?

  No.

• 13:17Speaker 01

  And so in a moment where if you say, is that your ego? If I lie.

• 13:21Simon Sinek?

  Yeah.

• 13:22Speaker 01

  Now there's a rupture in our friendship that's gonna 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, I care enough about this person to do what I need to do in order to preserve and pursue this friendship.

• 13:42Simon Sinek?

  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.

• 14:11Speaker 01

  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.

• 14:23Simon Sinek?

  And 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. Business partners, close friends, romantic partners, like however you want to define that.

• 15:00Speaker 01

  Yeah.

• 15:00Simon Sinek?

  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. It's disrespectful.

• 15:45Speaker 01

  Yes.

• 15:46Simon Sinek?

  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, 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, we balance the line. We sort of, we play the teeter totter of being myself,

• 16:30Simon Sinek?

  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.

• 17:05Speaker 01

  I 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

• 17:21Simon Sinek?

  Exactly.

• 17:21Speaker 01

  curse words fly.

• 17:23Simon Sinek?

  Exactly.

• 17:23Speaker 01

  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.

• 17:37Speaker 01

  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. You'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.

• 17:55Simon Sinek?

  Yep.

• 17:55Speaker 01

  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. And the same applies in friendship. And chicken or the egg on this one is, do you stop being vulnerable because you're not confident?

• 18:38Speaker 01

  Or you tried being vulnerable with the wrong person? Like you took the wrong risk?

• 18:46Simon Sinek?

  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.

• 18:58Speaker 01

  And that's when they start living their public persona in their private lives.

• 19:01Simon Sinek?

  That's where 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. But 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 romantic partner. And the times where you, it 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.

• 19:41Speaker 01

  Yeah.

• 19:42Simon Sinek?

  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.

• 19:53Speaker 01

  And by the way, your ego would have then

• 19:57Simon Sinek?

  Maybe even five years.

• 19:58Speaker 01

  probably yell at me for even asking the question and the relationship would have really taken.

• 20:02Simon Sinek?

  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.

• 20:12Speaker 01

  Gosh, I love that.

• 20:14Simon Sinek?

  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 told you 100 times.

• 20:23Speaker 01

  It's not about the toothpaste.

• 20:24Simon Sinek?

  It's not about the toothpaste.

• 20:27Simon Sinek?

  And the problem is, is we don't listen to the volume. We listen to the words and then we get defensive 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.

• 20:42Speaker 01

  Yeah. And then, by the way, I have the courage to say,

• 20:47Speaker 01

  I feel like there's something more at play. Can we talk about it?

• 20:50Simon Sinek?

  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?

• 21:07Speaker 01

  The 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

• 21:24Speaker 01

  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.

• 21:30Simon Sinek?

  The examples have to be specific.

• 21:31Speaker 01

  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 B, gosh, there is this little thing that I do that is totally grating on this person and it's so easy for me to stop doing it. And the impact is profound if I can.

• 21:52Simon Sinek?

  Okay, what do people not understand about friendship breakups?

• 22:00Speaker 01

  Oh, man, what do people not understand about friendship breakups?

• 22:07Simon Sinek?

  It's so big, that question.

• 22:09Speaker 01

  It's such a big question.

• 22:11Simon Sinek?

  I'm so glad you have to answer it and not me.

• 22:13Speaker 01

  Also, posited in the negative, like, what?

• 22:16Simon Sinek?

  I know.

• 22:19Speaker 01

  I think that people are much lazier and more passive

• 22:27Speaker 01

  in friendship breakups than they are in, like, romantic relationship breakups. And

• 22:35Speaker 01

  in being so are undermining the unbelievable importance of valuable friendships in our lives.

• 22:44Simon Sinek?

  Yep.

• 22:44Speaker 01

  And we've talked about this all the time. How

• 22:50Speaker 01

  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. And 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.

• 23:18Simon Sinek?

  Yeah.

• 23:19Speaker 01

  I mean, you think about some of the closest friends you have in your life.

• 23:24Speaker 01

  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. Like, it's a bizarrely counterintuitive thing.

• 23:42Simon Sinek?

  I 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.

• 24:01Speaker 01

  Yeah.

• 24:03Simon Sinek?

  And so we go through the excruciating pain of ending those relationships because we have to unwind a contract.

• 24:10Simon Sinek?

  Wait, there's no unwinding a contract in a friendship. And so we can, we can get away with being lazy or avoidant.

• 24:18Speaker 01

  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.

• 24:28Simon Sinek?

  Yeah. 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.

• 24:39Simon Sinek?

  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 happy in this 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.

• 24:57Speaker 01

  And by the way, sometimes like intentionally going to end a friendship is the best way to save it.

• 25:03Simon Sinek?

  I've tried so many times to end my friendship with you.

• 25:07Simon Sinek?

  And I just end up closer and closer.

• 25:09Speaker 01

  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 he just needed to hear that. And 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.

• 25:52Simon Sinek?

  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. And it's really quite dismissive. To assume that somebody's fine with bad behavior.

• 26:23Speaker 01

  Yeah.

• 26:25Simon Sinek?

  Or dismissive behavior, or being deprioritized constantly. Occasionally, it's acceptable, but constantly, it's not acceptable. And I'm guilty of it. I, there's one friend I have, 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.

• 26:44Speaker 01

  Hmm.

• 26:45Simon Sinek?

  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. And it got to the point where it was so unbalanced that I felt like such an asshole.

• 27:03Speaker 01

  Yeah.

• 27:03Simon Sinek?

  Because she kept showing up for me in my, 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.

• 27:15Speaker 01

  Yeah, or stop taking.

• 27:17Simon Sinek?

  Or stop taking. Yeah.

• 27:18Speaker 01

  And it's not a behavior, that, that amount of dismissiveness is much less prevalent in marriage or in work or. 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?

• 27:34Simon Sinek?

  Right.

• 27:34Speaker 01

  I'm not saying you should, like.

• 27:37Simon Sinek?

  You can't get away with it. You can't get away with it. The, the, uh, friends, I, 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.

• 27:56Speaker 01

  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. And by the way, depending on your bandwidth and how much you have going on in your life, whether you have kids or a job and how busy you are in work, that list is going to be longer or shorter. But you need to have a group and it should only be enough people on that list that you can actually give them the time the friendship deserves. That you call really, really good friends, because if you don't, I just think there's way, way too many things that you're missing out on.

• 28:39Simon Sinek?

  And, but I also find busy people are patient with busy people.

• 28:42Speaker 01

  Yeah.

• 28:44Simon Sinek?

  And it's not a question of how much time is committed, although some, actually, let me, I'm gonna take that back. Every friendship has its own currency. Like you and I, when we are together, we are all in, whether it's for 20 minutes, or an hour, or a day. Like you and I are very intense and very intentional in whatever interaction we have. But you and I can go months without talking. But it doesn't affect my feelings for you. So time is, quantity is not our currency, quality is our currency.

• 29:15Speaker 01

  Yeah.

• 29:17Simon Sinek?

  For other friends I have, quantity is the currency. Like, I like seeing them a lot. They like seeing me a lot, and it, or we talk a lot. And if that falters, one of us will say something's wrong.

• 29:28Speaker 01

  Yes. By the way, and then similarly with us, if we hung out and didn't go very deep at all, one of the people would say, hey, what's going on here?

• 29:39Simon Sinek?

  Right, because depth, depth is our, is our currency. And so you, if you and I are superficial, one of us is, is gonna either say, is, are you mad at me, or is something else going on in your mind?

• 29:50Speaker 01

  By the way, I think busy people are patient with busy people. And I also think busy people are normally the people that always make the time for the things that matter more than people that are not busy, in my experience.

• 30:01Simon Sinek?

  Ah, that one I don't, that, let me think about that for a second. I mean, look, I'm my most.

• 30:05Speaker 01

  I mean, there's that adage, if you want to get something done, ask your busiest.

• 30:09Simon Sinek?

  Right, ask a busy person, right. Here's a question I'm supposed to ask you. You're gonna, oh, this is so funny. You ready?

• 30:21Speaker 01

  Yeah.

• 30:22Simon Sinek?

  You're gonna laugh.

• 30:24Speaker 01

  Right.

• 30:25Simon Sinek?

  I can't even read it with a straight face. Should you do business with your friends, or should you not mix the two?

• 30:36Speaker 01

  We already covered this one.

• 30:38Simon Sinek?

  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, before we got on the podcast. And now we're asking, should we even, the question I'm asking is, should we be doing this?

• 30:51Speaker 01

  I mean.

• 30:55Speaker 01

  Well, yes, I think I I don't think that's I don't think it's binary.

• 31:02Speaker 01

  That's like saying, should you get married or not? It depends on who you are and who the other person is and how you're going to navigate through it.

• 31:11Simon Sinek?

  I think, for example, if you have no money, you shouldn't make a choose a business partner who's a multimillionaire.

• 31:19Speaker 01

  So there's a power imbalance.

• 31:20Simon Sinek?

  Because one of them is hungry and one of them isn't. And the level of commitment they will give to the business will be very, very different. It'll breed resentment. And so what I've learned, having successful and unsuccessful experiences in business with friends, is the motivations have to be similar and the very clear expectations set early on, because we will make assumptions about the other person's commitment. And you and I, again, are pretty good about that. We will, you and I have had blunt conversations, say, listen, and it's not personal. It's just like, hey, listen, I need you to manage my expectations. What realistically do you have time for in this? Because I'm going to go all in. I'm okay if you're not all in, but I need to know you 10% in, 20%, 50% in. And

• 32:04Simon Sinek?

  by the way, that number can change, but you got to tell me.

• 32:07Speaker 01

  Yes.

• 32:08Simon Sinek?

  And I think you can go into business with friends so long as everything's on the table. Don't leave anything up to assumption.

• 32:16Speaker 01

  And.

• 32:18Simon Sinek?

  Is that fair?

• 32:19Speaker 01

  I think that's 100% fair. And I'd also add this. You can't stop being friends. You don't replace the friendship relationship with a colleague relationship. You now have two relationships.

• 32:37Simon Sinek?

  That is true and underappreciated. Let's go down that rabbit hole. You're dual hatted.

• 32:45Speaker 01

  Like, okay, so you and I. If I'm having a hard time in work or with a with my dad or with my wife or whatever, if I just need someone to talk to, you're one of my people that I'll call.

• 33:00Simon Sinek?

  Yeah, likewise.

• 33:01Speaker 01

  Okay, now we started business. Now we have a whole other, by the way, like that's what we're gonna talk about. When we talk, it's normally about something going on in our lives, or we're just going out and giggling and having fun and talking about philosophical stuff. We started business. Now we have a whole nother basket of things we need to talk about. If we stop doing the first group.

• 33:23Simon Sinek?

  Yeah.

• 33:24Speaker 01

  Like, it's like when you grow a business, you can't stop being the thing that gave you the opportunity to grow.

• 33:30Simon Sinek?

  But we have learned, and I think it's important, which is you learn to compartmentalize to a degree and talk to each other differently.

• 33:36Speaker 01

  Yes, exactly.

• 33:37Simon Sinek?

  When you and I are having a business conversation, we do not, we sound like we love each other, we sound like we trust each other, we can speak to each other in shorthand, we can be a little bit irreverent, like we can do all those things that a friendship affords you, but it sounds like a meeting.

• 33:50Speaker 01

  But then we'll put our friendship hat back on and pursue that relationship.

• 33:54Simon Sinek?

  And it is very compartmentalized, and with practice, it can be very fluid. We can actually bounce between the two, but there's two distinct relationships happening that if somebody were to, you know, watch, they would hear our tones of voice sound different, even our level of respect changes. You know, like if we're in a friendship, you say something, I'd be like, that's bullshit. But if we're in a business context, I'm not gonna speak to you that way.

• 34:23Speaker 01

  Yeah.

• 34:24Simon Sinek?

  I'm gonna say, I don't think I agree with that one. I think, can I push back on that?

• 34:28Speaker 01

  It's almost what we were saying at the very beginning, the principles, our principles remain the same, but our actions will change.

• 34:33Simon Sinek?

  And we're code switching in the relationship because we have to.

• 34:37Speaker 01

  Yeah.

• 34:37Simon Sinek?

  Because, and I think that's where people make a mistake. They act like friends in the business context, or they act like business in the friends context.

• 34:43Speaker 01

  Yeah.

• 34:43Simon Sinek?

  And they're conflating the two because it happens to be the same person. It happens to be the same person.

• 34:50Speaker 01

  I mean, when we were doing the final edit on unreasonable hospitality, had any other friend said some of the things to me that you said to me then, that would, but because I trusted you to do that project with you because of our friendship, but once we were doing it, we were colleagues.

• 35:09Simon Sinek?

  We were colleagues and, and again, the friendship affords both of us a little more latitude.

• 35:16Simon Sinek?

  There's still a level of respect. You just adjust. You, you, you, I think you have to. I've hired friends to work with me. And so they, they went from being my equal to my work subordinate. And I hate the term, but there is a work hierarchy. I pay their salary. And

• 35:36Simon Sinek?

  that one is tricky. But because it's based on respect, there's still a code switching. Like when we're in work mode.

• 35:43Speaker 01

  Yeah.

• 35:44Simon Sinek?

  I do get the final word. They can push hard, hard, hard. But at the end of the day, if I say, look, this is, this is my decision. That's it. We're done. And that's it. No pushback. But when we're not at work, I have to remember that I'm not the boss. Like now we're equals.

• 36:01Simon Sinek?

  And I've gotten really good at that. But I, I have struggled because not everybody's as practiced. I can compartmentalize the two differences.

• 36:09Speaker 01

  I think anyone listening to this that is a part of a family business can resonate with everything we're saying very, very clearly. Right? It's no different. If I work with my dad, when I go to work, he's not my dad. Okay, he's my boss. And at home, he's my dad. And I'm going to engage with him differently as my dad than I am as my boss. And

• 36:29Simon Sinek?

  Yeah.

• 36:30Speaker 01

  The moment you stop doing that, you're creating either tension in that relationship or in the many surrounding relationships.

• 36:37Simon Sinek?

  And you have to be able to separate. Like I work with my sister. And when we're in work mode, we talk to each other quite differently than when we're in like brother and sister mode.

• 36:45Speaker 01

  Yeah.

• 36:46Simon Sinek?

  It's a toggle.

• 36:48Speaker 01

  I feel like the word code switching, like we're starting to gather negative connotations over time. But in this context, I think it's, what we're saying is it's a form of honestly, respect.

• 37:00Simon Sinek?

  It's a term that comes from social sciences and it's, it just comes, I learned it way back in anthropology. When I was an anthropology major in college. And it was not, it didn't have any baggage associated to it. It was just, it was just a thing, you know?

• 37:14Speaker 01

  Yeah.

• 37:15Simon Sinek?

  That you act differently for the environments that you're in.

• 37:17Speaker 01

  But in this context, like it's saying, hey, If I'm your friend and now I work for you, I do need to change the way I engage with you.

• 37:25Simon Sinek?

  You have to change the code by which you follow in how you engage.

• 37:28Speaker 01

  As a form of respect, not just to you, but to everyone around us.

• 37:33Simon Sinek?

  So one of my best friends in the world is a senior officer in the military, right? And we're irreverent to each other. We call each other in good times and bad times. He's one of my best friends. And when I'm in an office with him in on his base with his subordinates sitting around him, I call him sir.

• 37:55Speaker 01

  Hmm.

• 37:56Simon Sinek?

  Because I I show respect and I I, you know, I sometimes use his call sign as well. And people know we're familiar, but I don't overplay the familiar card because it's rude to the room and disrespectful to the rank that he's that he has. And I think it undermines his position. So I show particular deference. I would never call him sir outside of. You gotta be kidding. But like if I worked in your restaurant and you asked me to do something, I wouldn't overplay the friendship. So I'm simply making a case that switching the code by which you follow for the environment you're in, like, let's say you and I called each other Pookie. Right? That we that every time we, hi, Pookie, hi, Pookie.

• 38:37Speaker 01

  This is simply a hypothetical.

• 38:39Simon Sinek?

  Yeah.

• 38:41Speaker 01

  Just to be very, very clear, I'm speaking very closely to them.

• 38:46Simon Sinek?

  And you and I always call each other Pookie, right? And if I'm working for you now and you come to work and I'm like, hey, Pookie, it undermines and it and it creates doubt that you're giving me preferential treatment because it's excessively familiar.

• 39:01Speaker 01

  People will respect me and you both less.

• 39:05Simon Sinek?

  Correct.

• 39:06Speaker 01

  I think in any relationship.

• 39:10Speaker 01

  We make investments, like relationship capital investments. And you can draw down on them a little bit, but if you start overdrawing on those accounts, suddenly you wake up one day with, with a, with a problem on your hands. And I, I think that's not just pertaining to friendship and work, right? Like, yeah, you're going to get more latitude if you're really close. But if you take advantage of that, you're going to create real issues. The same is you do get grace from a really good friend. You can cancel on them at the last minute and they will understand. But if you do that too many times, you need to maintain a positive balance in that account. Otherwise, it's not

• 39:55Speaker 01

  an actual friendship.

• 39:57Simon Sinek?

  You know what I'm learning from this whole conversation? If there's a theme that's running through this whole conversation, it's the term respect.

• 40:05Simon Sinek?

  You have to respect the person for who they are, for what, what they are doing, what they're trying to do, in addition to being their friend.

• 40:16Simon Sinek?

  Like, I have deep, deep, deep love for you, but I also have deep, deep, deep respect for you.

• 40:23Simon Sinek?

  And because I have respect for you, how I will talk to you publicly is going to be very different than how I talk to you privately, because I want to big up you in public. Where if I talk to you that familiarly in public, it would undermine what you're working towards.

• 40:39Speaker 01

  Yes.

• 40:40Simon Sinek?

  And so my, I'm not kowtowing, I'm offering support for somebody I love. You know, it's kind of like, it's kind of like fight and private, but then once a decision is made, we all toe the party line.

• 40:54Speaker 01

  A hundred percent.

• 40:56Simon Sinek?

  It's the same thing, which is there's nothing worse than somebody who publicly undermines whatever the decision is, because they disagree. You, we all had our opportunities to fight, decisions were made, now we all work. And by the way, I've seen this in the Marine Corps. The Marines look for this. When they study leaders, they're also studying followership. And they want to see if you disagree with your leader, and the leader asks for your opinion, that you will be honest about the fact that you think we should take a different course of action. But once the leader makes the decision, that you will work tirelessly to see that the leader's decision is successful.

• 41:28Speaker 01

  Well, yeah.

• 41:29Simon Sinek?

  And if it fails, you don't say, I told you so.

• 41:32Speaker 01

  Yeah.

• 41:33Simon Sinek?

  You pivot and try and find a new way to see that the team and the leader succeed. And they're looking for good followership. And I think that's what we're talking about here, which is respect. That there's a level of respect and and support.

• 41:49Speaker 01

  And by the way, just to that point.

• 41:53Speaker 01

  In every great friendship.

• 41:58Speaker 01

  Sometimes you need to lead and sometimes you need to follow.

• 42:02Simon Sinek?

  Yeah.

• 42:02Speaker 01

  If you're always only playing one role. There's something wrong, I think.

• 42:07Simon Sinek?

  Yeah. And look, at the end of the day.

• 42:11Simon Sinek?

  Like you and I had disagreements galore as we were editing your book.

• 42:16Speaker 01

  Yes, I I've said more times than I can count that you are the greatest editor on the planet. I really mean it. And like the process, I feel like just like a peek behind the curtain, the process of editing the book with Simon was this. I went over to your house, sat across the table. This is what you insisted. I had sent you the manuscript like six weeks earlier and called you and said, hey. Have you read it like really craving some feedback here? You're like, come over. So I went over to his house and for five days, read the book out loud. And by the end of those five days, we shaved 25% off that book or 20%. I don't know the percent, a big number. And the book is markedly better, markedly better because.

• 42:58Simon Sinek?

  You know why that process worked? Because if I sent you my comments, cut this, cut this, cut this, this doesn't work, move the order, change this. Now I'm criticizing a creative product, which is very personal.

• 43:10Speaker 01

  Yeah.

• 43:11Simon Sinek?

  And every creative person will take the criticism personally because you can't not. Right? Is it's hard not to. And it's cold. When we're reading the book together and I'm making observations, you're with me.

• 43:27Speaker 01

  Yeah, it was like a difference between to and with.

• 43:31Simon Sinek?

  I didn't shave 20% off. We shaved 20% off.

• 43:35Speaker 01

  Yeah.

• 43:36Simon Sinek?

  I didn't change the first chapter to the second chapter. We decided that the first chapter should be the second chapter.

• 43:42Speaker 01

  But here's the thing. This is my first book, book, book. You're a New York Times bestseller multiple times over. Yeah, I can totally understand how some people be like, yeah, but if I tell people that Simon played such a big role in editing it, then they're not going to think I had anything to do with it. And like, it's going to totally like, it's, I get that, by the way.

• 44:04Simon Sinek?

  I get it too. By the way, I, I, by the way, I've been there. I've been insecure about, is it my accomplishment? Will people respect me less if I had help? And I, I think

• 44:18Simon Sinek?

  there is a line, like my friends in the military who are now retiring and going into private sector. These people are very senior, they're badasses, and they're so humble. The business world misperceives them as insecure.

• 44:32Simon Sinek?

  Cause they're like, you, she, they're like, no, I couldn't have done anything without my team. My team is, they, they do it so excessively that when I talk to the people who they've had meetings with, I've like, how'd the meeting go? They're like, I don't know if he's got it. He just doesn't seem tough enough. I'm like, are you kidding? You know who you're talking to? And they're like, yeah, he just came across as like a little soft, like, just like, I don't know what he's, I think, yeah. And it's because they overplay the humble card. So there is a line.

• 44:57Speaker 01

  But if you play it in the right way, not only will people not think you're less than, they will be like, oh my gosh. This is a really confident person who wrote a damn good book and is so confident in what he did that he's willing to really shine a light on, on the person that helped him do it.

• 45:15Simon Sinek?

  And here's my favorite thing about unreasonable hospitality. I've told it to you. I say it publicly all the time. My favorite thing about unreasonable hospitality is you have sold more books in the time it's been out in one year, two years, whatever it's been. Then I have sold with any of my books in the same period of time. And your book is on trajectory to outperform Start With Why? And that makes me so insanely proud. It makes me so insanely proud that the success of unreasonable, your unreasonable hospitality is so good that you will blow past Start With Why and you will do it in a much shorter, it took me a million years

• 45:57Simon Sinek?

  to sell the many, as many books as I've sold with Start With Why. You will be there in less than half the time. And I cannot tell you how I have genuine joy for that. Genuine joy.

• 46:08Speaker 01

  I love you.

• 46:12Speaker 01

  Thank you.

• 46:14Speaker 01

  It's a multi-layered, multifaceted, thank you.

• 46:17Simon Sinek?

  I love you too, and to watch, to be a part of your second act, because I had nothing to do with your first act. I simply came and ate at your restaurant a couple of times. That was all I did to contribute to your first act. But your second act, to be able to stand alongside you, because we became friends when you were still at the restaurant.

• 46:37Speaker 01

  Yeah.

• 46:37Simon Sinek?

  And so you were my friend first, but to get to stand by you and be a part of your second act while you are a part of mine as well, because I'm doing new things and you are a partner to me in these new things. It, I guess we've just answered the question, like, can you go into business with your friends? You're damn right you can.

• 46:57Speaker 01

  You started this by saying, is this phase of my life, does he a coming or has it been a surprise?

• 47:08Speaker 01

  Yeah, it's been a surprise. And the greatest surprise ever.

• 47:15Speaker 01

  I just feel like everyone has another chapter in them and whether they actually live it

• 47:22Speaker 01

  is to be determined, but we all have it.

• 47:25Speaker 01

  It's just a matter of flipping the page and seeing what's, what's on the next one and.

• 47:29Simon Sinek?

  I will close with this, if you choose to have a second act, a third act, a fourth act, whatever act you're into or up to,

• 47:38Simon Sinek?

  you will find the courage to do that, the confidence to do that,

• 47:43Simon Sinek?

  if you do it with a friend. Because that friend who's with you, judges you zero, loves you no matter whether it succeeds or fails, whether you do it with them or do it by yourself. So long as that friend is by your side, you will find the courage to make dramatic, difficult change, dare I say it, easy.

• 48:04Speaker 01

  This has been really fun, Pookie.

• 48:10Simon Sinek?

  Oh God, I hope that doesn't stick.

• 48:15Simon Sinek?

  It's my bad. I should have picked like, "Bro." Oh my God, "Bro."

• 48:23Simon Sinek?

  It's even worse. I guess Pookie's what we're stuck with.

• 48:26Speaker 01

  Shit.

• 48:30Speaker 01

  Hey buddy.

• 48:32Simon Sinek?

  Hello buddy.

• 48:36Simon Sinek?

  Uh, I think we have to log off.

• 48:38Speaker 01

  This is fun. I'll call you soon.

• 48:41Simon Sinek?

  I love you. Bye.

• 48:42Speaker 01

  I love you.

• 48:48Simon Sinek?

  If you enjoyed this podcast and would like to hear more, please subscribe wherever you like to listen to podcasts. And if you'd like even more optimism, check out my website, simoncinek.com for classes, videos, and more. Until then, take care of yourself, take care of each other.

• 49:07Simon Sinek?

  A Bit of Optimism is a production of The Optimism Company. It's produced and edited by Lindsay Garbenius, David Ja, and Devin Johnson. Our executive producers are Henrietta Conrad and Greg Rudeshan.