Major General Dan Caine, Randall Stutman, Robert Greene, and Jeni Britton Bauer on Becoming a Great Leader | This is The Truly Inexcusable Thing

Ryan reads today’s daily meditation and looks back at some of the best interviews from the Daily Stoic Leadership Challenge. Ryan talks to Major General Dan Caine about the importance of defining success before you set out to try to solve a problem, Randall Stutman about the important distinction in being subtle and being manipulative, how great leaders see themselves as stewards, not owners, Robert Greene about their experiences and lessons learned from watching American Apparel’s unhinged CEO run a publicly traded company into the ground, and Jeni Britton Bauer about how she thinks about the tension between being efficient and having the highest standards. Sign up for the Daily Stoic Leadership Challenge: dailystoic.com/leadershipchallenge → We hope you join us in the 2022 New Year New You Challenge. It’s 3 weeks of actionable challenges, presented in an email per day, built around the best, most timeless wisdom in Stoic philosophy. Just go to https://dailystoic.com/challenge to sign up before sign ups end on January 1st! Reframe is a neuroscience based smartphone app that helps users cut-back or quit drinking alcohol. Using evidence-based tools, techniques and content, Reframe guides users through a personalized program to help them reach their goals. To learn more go to JOINREFRAMEAPP. COM/stoic and use the code STOIC for 25% off your first month or annual subscription. Download Reframe on the App Store today. LMNT is the maker of electrolyte drink mixes that help you stay active at home, work, the gym, or anywhere else. Electrolytes are a key part of a happy, healthy body. As a listener of this show, you can receive a free LMNT Sample Pack for only $5 for shipping. To claim this exclusive deal you must go to drinkLMNT.com/dailystoic. If you don’t love it, they will refund your $5 no questions asked. Trade Coffee will match you to coffees you’ll love from 400+ craft coffees, and will send you a freshly roasted bag as often as you’d like. Trade is offering your first bag free and $5 off your bundle at checkout. And, this holiday season, give the coffee lover in your life the gift of better coffee too, with their own personalized gift coffee subscription from Trade. To get yours, go to drinktrade.com/DAILYSTOIC and use promo code DAILYSTOIC. Take the quiz to start your journey to the perfect cup. Sign up for the Daily Stoic email: https://DailyStoic.com/dailyemailCheck out the Daily Stoic Store for Stoic inspired products, signed books, and more. Follow us: Instagram, Twitter, YouTube, TikTok, FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. 📢 Share | ⚙️ Manage Subscription

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

• 0:03Ryan Holiday?

  Welcome to the Daily Stoic Podcast where each weekday we bring you a meditation inspired by the ancient Stoics, a short passage of ancient wisdom designed to help you find strength and insight here in everyday life. And on Wednesdays, we talk to some of our fellow students of ancient philosophy, well-known and obscure, fascinating and powerful. With them, we discuss the strategies and habits that have helped them become who they are, and also to find peace and wisdom in their actual lives. But first, we've got a quick message from one of our sponsors. This is the truly inexcusable thing. Seneca once said, quoting Fabius, that the only inexcusable

• 0:48Ryan Holiday?

  thing for a commander to say was, "I did not think that could happen." And of course, he is right. The job of a leader is to be prepared, to have a plan, to anticipate all possible and probable outcomes. Whether it's a military campaign, a creative project, or a business negotiation, this is why the Stoics practiced "premeditatio malorum", and made a point of always doing their hard-winter training. But in truth, what is worse than not doing the training, what is worse than even saying, "I did not think it could happen", is saying, "Oh, I didn't think that could happen again." And yet, that is something that people have found themselves saying throughout this pandemic. It is something

• 1:30Ryan Holiday?

  that past leaders have also said in other times of uncertainty and difficulty. As if there was no such thing as variance or double-dip recessions, as if it's not possible for bad things to get worse, as if something you fixed once can't come undone or reoccur, as if 100-year storms only happen once every 100 years, as if the roulette wheel can't hit double zero again on the very next spin, as if some people or places don't get freakishly unlucky, as if the person who wronged you and got away with it isn't now actually more likely to do it again, even if they have assured you otherwise. You have to be prepared,

• 2:11Ryan Holiday?

  always. You cannot let your guard down. As they say, fool me once, shame on you. But fool me twice, it's on me. If it's something that can happen, it can happen to you. And more urgently, you have to understand if something can happen to you, can happen to you again.

• 2:35Ryan Holiday?

  Hey, it's Ryan. Welcome to a very special episode of the Daily Stoic Podcast. I think one of the absolute best things that we've created here at Daily Stoic was this Daily Stoic Leadership Challenge. We've been doing these little challenges here and there. And as you know, we've got the New Year, New You Challenge that's, that's rolling now. And we'd love to have you join us if you haven't already. But I think the best one, that the best and biggest one, different than the others we've done, is this Daily Stoic Leadership Challenge. It's longer than the others. It was six, maybe nine weeks of like daily content on how to be a better leader. And the truth is, while not all leaders are Stoics, all the Stoics were leaders in some way.

• 3:19Ryan Holiday?

  This is the distinction in the ancient world between the Epicureans and the Stoics, is that the Stoics jump into the fray, the Stoics lead or active in public life, and the Epicureans run away from that. And so I really wanted to see what the Stoics have to teach us about leadership, because they weren't just small-time leaders, anyway. Marcus Aurelius is the head of the biggest empire in the world, Athenodorus, Arius Didymus, they're the advisors to the first emperor of Rome. The Stoics advise kings and generals. Pompey, when he goes out on one of his, his campaigns, he stops and sees Posidonia, right? One of the early Stoic philosophers. So the Stoics were always coaches of leaders or leaders themselves. And I think this challenge is one of the absolute best things we've ever done.

• 4:04Ryan Holiday?

  I'd love to have you join us. You can sign up at dailystoic.com/leadershipchallenge. But in today's episode, I wanted to bring you some, some quick excerpts, some of the best lessons from the leaders that we interviewed as part of this series. Normally, the challenges are, you know, lessons from the Stoics, lessons from me. But in this one, we did leadership deep dives on each of the weeks with great leaders, right? And we, we talked to them about how they apply Stoicism to whatever it is that they do. We, we talked to Major General Dan Kane on how to become a great leader. He was the first plane in the sky on 9/11. He's had success in the business world. And of course, leading men and women into battle. And so our, my interview with Dan Cain is great.

• 4:49Ryan Holiday?

  Couple of weeks ago, we gave you an excerpt from the Randall Stutman interview. Here's Randall Stutman, one of the great CEO coaches of our time, talking about how to be a lifelong student of leadership. And then the one and only Robert Greene, who of course I wanted to talk to in this challenge, because if you don't understand Robert's thinking, Robert's understanding on power and political dynamics, you're not going to be successful in the, the political workplace that, that simply exists and has always existed. And we talk about he and I's personal experience, watching American apparel implode. And then we talked to Jenny Britton Bauer, the founder of Jenny's Ice Cream, not just

• 5:33Ryan Holiday?

  a great American small business success story. The President of the United States's favorite ice cream is the ice cream she made in her shop in Ohio, and it now has locations all over the world. She came out a couple of weeks ago and I got to see her in person as well. But we talk about how to be efficient, first having high standards. And clearly she's been through all sorts of adversity. Imagine running a retail shop or a food shop in the midst of this pandemic. And that was only the most recent adversity for Jenny's Ice Cream. So, great interviews. I can't wait for you to listen. And of course, if you haven't checked out the Daily Stoic Leadership Challenge, I'd love to have you. I think it's one of the best things we'll, we've ever done. And I'd love to, to see you there in it.

• 6:18Ryan Holiday?

  You can sign up again at dailystoic.com/leadershiplchallenge. Here's me talking to Major General Dan Cain. I wanted to start with, with nine 11 being, this is the 20th anniversary. You know, we've talked to a bunch of interesting leaders in the course of this course. And they've been through some crises and difficulties, but nothing quite like being one of the first planes in the sky on nine 11. So could you maybe walk us through that day and what that was like?

• 6:56Speaker 01

  Of course, yeah, it's it's hard to believe it's been 20 years, you know, last weekend and

• 7:06Speaker 01

  it's just strange to look back on that. On September 11th, 2001, I was actually stationed here in Washington DC out at Andrews Air Force Base. I was flying F-16s. I'd been to the Air Forces Top Gun School where we don't play much volleyball. We mostly focus on on getting better as tacticians with a little bit of jest towards my Navy brothers and sisters. And, you know, we had just gotten back as a squadron from out in Las Vegas in Ellis Air Force Base where we were getting ready to deploy. And, you know, that Tuesday here in Washington was a beautiful

• 7:50Speaker 01

  and gorgeous day. And I was not scheduled to fly that day. I was originally sort of running the flying operation for for the squadron as the chief instructor and tactician. And, you know, as we came in that morning, we obviously had had no idea what we were going to face. And we were in a meeting at the squadron, just a training meeting, when one of our young intelligence professionals came in and said, "An airplane has has just hit the World Trade Center." And of course, my first thought was, "It's a small civilian airplane. This couldn't

• 8:29Speaker 01

  be." And, you know, we all, as you get older, as leaders, you start to develop that spidey sense of just something's not right. And I felt that. Got up, walked into our squadron lounge where we had a big flat screen TV. And and remember, I still get chills today, even remember clearly the helicopter news shot showing the first tower burning when when the second airplane flew into the picture and hit the building.

• 9:10Speaker 01

  Silence, could have heard a pin drop and we sat there for what seemed like a long time, which was probably just a very few seconds. And I, I went to the, to the desk where we had all of our communications gear and I picked up the phone and called the Secret Service and said, I don't know what's going on. What do you need us to do? We had a relationship with the Secret Service in Washington because we flew out of the same airfield as the president. And the next phone call was the White House saying, get anything you can airborne.

• 9:48Speaker 01

  The nation is under attack. And right at that point in time, my boss Brigadier General Dave Worley walked in and I handed him the phone and I said, hey, sir, this is, this is for you. And we went and got ready to fly. And it was myself and a wingman and there were two other folks as well. And we got our, got our gear on and, and went running back to the ops desk and, and, and met General Worley. General Worley read us the rules of engagement for defending the National Command Authority. It was very liberal and it was on us. And, you know, when

• 10:31Speaker 01

  you think about leadership for the folks on the, on the, on the call and on the video here.

• 10:38Speaker 01

  I will never forget what then General Worley said to us. He's just read us the rules of engagement, which are extremely liberal. The decision is clearly mine. It's the cap commander, the mission commander over the Combat Air Patrol. And he reads us verbatim and then he pauses and he looks at us and says, hey, Dan, look, I don't know what you're going to face out there. I think you're probably going to have to make some very difficult decisions, but here's what I want you to know. I trust you. You're going to do the right thing.

• 11:12Speaker 01

  And no matter what, I have your back. And you want to talk about saying the exact, exact right thing at the exact right moment. Uh, we ran to the jets and scrambled and, and you know, we're flying that morning. Uh, we took off, I think, right around the same time that the real heroes or some of the real heroes of that day, the passengers of Flight 93 were, were assaulting inside the airplane, knowing full well what they were facing, knowing what had happened in New York City. And yet finding the courage um, to, to step up.

• 11:55Speaker 01

  Um, not having taken the same oath that we take to uphold and defend the Constitution, but knowing that their nation needed them to do something. So flew that the rest of that day and a lot of intercepts and a lot of sort of keeping, keeping airplanes away from downtown Washington. And our squadron flew for the next 45 days after that. And I deployed pretty quickly overseas to, uh, to start fighting Al Qaeda.

• 12:24Ryan Holiday?

  Well, to bring all that together, I, I think there's a couple of interesting themes. So one, which is, uh, open lines of communication. I think it's pretty incredible that you're just sort of very quickly on the phone with the White House. I was reading a, a book about, uh, Admiral Rickover recently, and I didn't, I, they just sort of mentioned it offhandedly. But I guess for, maybe it's still the case or, but it was the case in the, during the Cold War, that every, uh, commander of a nuclear submarine could directly call the White House. Like there was just a phone they could pick up and the, it would ring at the president's desk. And, and so I think sometimes we think these, these organizations are huge and there's this massive chain of command.

• 13:08Ryan Holiday?

  But at the top, it sounds like, uh,

• 13:11Speaker 01

  Well, we didn't call, they called us, um, just to be clear, you know, I called the Secret Service.

• 13:16Ryan Holiday?

  But that's what I mean, that's what I mean.

• 13:18Speaker 01

  Yeah, yeah, yeah.

• 13:19Ryan Holiday?

  Is, is that at the, at the end of the day, the really elite operators have to be completely flat. There has to be open lines of communication and flexibility there.

• 13:29Speaker 01

  And flatness is something from a leadership perspective that we value greatly. Certainly, I value greatly, and I drive the organizations that I'm blessed to lead or be a part of towards that flatness. I think as leaders, if we don't understand what is happening at the edge of the empires that we're blessed to lead, serve, and help with, then we can't possibly understand what's really going on. So, flatness is a key to that.

• 13:58Ryan Holiday?

  Yeah, because often, you know, I think especially at the lower levels, you can be like, "Well, I pass this up the chain and something will happen." But I think it's interesting that you called the Secret Service. You didn't sort of wait around and say, "Let's see if somebody needs me, and let's wait to see where this goes." You sort of used the contacts you had on that day to sort of say, you know, "What do you need from me? What can I contribute? What's going on?"

• 14:25Speaker 01

  I think we've got a responsibility as leaders, at whatever level you're leading at, to be proactive and not reactive, to realize when there's a white space and lead your organization or yourself towards that white space to improve the overall effectiveness, efficiency, combat, whatever kind of organization you're leading, and move towards the problem.

• 14:51Ryan Holiday?

  Well, and that goes to the passengers on Flight 93, which you texted me a transcript of that sort of call on 9/11, which I was, it always sort of gives you the chills to read. I think the idea that, yeah, they weren't sort of technically leaders in any way. It was, you know, a handful of people talking on, you know, phones on airplanes, which I think younger people don't even remember was a thing, that you could swipe your card and get a handset out of the back of a seat.

• 15:25Ryan Holiday?

  But they sort of anointed themselves leaders and it was, I thought was remarkable is that you have this 911 operator relaying information from all over the world, sort of that all these people involved, although they had no official authority or even official obligation to do anything, took it upon themselves to say like, look, we might not be able to solve this thing, but we cannot contribute to the problem. We cannot make this tragic event more tragic and we're going to try to do something.

• 15:59Speaker 01

  And I, you know, I just, I think about him every day, right? And, and when, and that is real courage, knowing what is going on in the United States at that point in time and having the intestinal fortitude, the bravery to stand up and go forward, knowing is just an incredible example. You know, America started to fight back immediately and they were the first steps, the firefighters that headed up buildings were the first steps. You know, the people at the Pentagon were the first steps. And out of this tragedy of

• 16:39Speaker 01

  September 11th, we can find incredible goodness on who we really are as a country. And I hope we just always take advantage of those, those examples moving forward.

• 16:52Ryan Holiday?

  Yeah, you know, it's, it's almost easy to celebrate the firefighters and the police officers, but, but there were also the office managers and the employees and the people who had, you know, they worked in this enormous office together, but they'd never met before and, and again, had no real obligation to anyone but themselves and decided, hey, I'm not leaving anyone behind or hey, I'm going to do what I can here. You know, that, that is also what leadership, leadership isn't this thing you get promoted to necessarily. It's also what you do in moments of crisis.

• 17:27Speaker 01

  Absolutely, absolutely. And it's, it's, you know, we're, it could have been a lot worse that day had they not, had those people not evacuated the towers and, and those people stood in the, in the stairwells, helped other people get down there, people in the Pentagon, it could have been a lot worse.

• 17:45Ryan Holiday?

  Or that plane, you know, flight 93 could have crashed into the White House or the Capitol building.

• 17:50Speaker 01

  Would have been much worse.

• 17:55Ryan Holiday?

  And then when I think about leadership, although thankfully you didn't have to, it strikes me that what your commander was talking about was the idea that within the latitude that you had been given, you would have, you, you potentially would have to make some very hard decisions in the moment, which is also, you know, something we've talked about, but sort of the definition of leadership to me is, you know, can you make hard decisions with limited information and limited time?

• 18:28Speaker 01

  Yeah, you know, and as I reflected on that day, and look, we just did our jobs. We, we, we, we just did our jobs and thankfully we didn't have to make the decision to shoot somebody down. As I reflected back on that day and, and folks have asked me, you know, were you, were you scared or what, or what was going through your mind and whatnot? I mean, of, of course, but overwhelmingly the thing that, and I'm grateful for this experience in some ways as a leader. My largest concern was not to miss somebody and not,

• 19:10Speaker 01

  and not to be able to prevent or be unable to prevent an airplane going into the White House, going into the Capitol. And, and that drove everything. And as I didn't realize that at the time, I was younger and a captain, you know, a young captain. But as I've reflected on that over the years, I'm grateful for that and other situations like that where I, I built some trust and confidence in my own instincts as a leader to be able to make difficult and complex decisions with limited information in short amounts of

• 19:50Speaker 01

  time. And, and that is something that, that I've, I've, I've learned to value greatly in my life.

• 19:57Ryan Holiday?

  Yeah, and it strikes me as similar to the idea as we talk about sort of different organizations and how they're structured, that what your commanding officer did there was give a really clear sense of what sort of commander's intent was. Like, he was like, "This is what you're being tasked with. These are the legal constraints that you have to operate on. Here's what I expect of you." And then he said, "The rest is your call," right? He sort of trusted that your training, your judgment, your conscience, you know, your sense of duty would take care of the rest.

• 20:39Speaker 01

  Absolutely. And clarity of guidance, especially in today's day and age, and how you think, develop, and then articulate that guidance is so important to organizations, and so important to leaders to get it right, and get it out there, and stay consistent on what that guidance and intent looks like. Because in the end, what that drives towards is what is the culture that your organization is going to embrace, and how are you going to move the organization from where it is now to where it probably needs to be? And

• 21:18Speaker 01

  Gerald Worley, who tragically, in a horrible story, after he retired, was volunteering with his wife at Walter Reed Army Medical Center, and they passed away in a Metro Rail accident in Washington DC, instantly killed the two of them together. And so I

• 21:39Ryan Holiday?

  I didn't know this.

• 21:40Speaker 01

  Yeah, I went to see his grave over the weekend and talked with his family. But getting that clarity, guidance, and intent right, and then being consistent over and over and over again on what that culture has to be in order to achieve that end state, is really important. And a lot of that comes down to sort of boiling it down to the ability, in my mind, to understand what is the situation, the context, the resources that you have, and then bringing those elements together into guidance and commander's intent.

• 22:21Ryan Holiday?

  Here's me talking to Randall Stutman. So you talked about this idea of giving up power to keep power. One of the ways I've seen you do this, you've talked about it.

• 22:34Ryan Holiday?

  Maybe it doesn't seem like giving up power, but it is. I think so often people think the leader is in charge. It's all about the leader. The leader's the main person. That's who we're all behind. But you've talked about this idea that a leader is a fan, that you want to be. What was it? You wanted to be a great fan or unconditional fan? Walk me through your, your sort of, it's not quite cheerleading, but talk to me about how a leader is a fan and supports the people who work for them. I found this really interesting.

• 23:03Speaker 02

  So that's really the magic or the foundation of inspiration and motivation. Right? I mean, people get inspired and motivated by lots of things. But the one thing that everyone wants more than anything else is the people that they respect and admire rooting for them, cheering for them, clapping for them, right? Wanting them to succeed. What it means to be a fan is I will do anything for you to succeed. But I'm going to be honest with you. I'm going to be, I'm going to hold you accountable. Our relationship has nothing to do with your performance, but I am here to help you succeed and I want you to succeed. And I'm going to do everything in my power to do so. I'm not going to put up hurdles. I'm not going to, you know, create a gauntlet for you. I am going to simply root for you and I'm going to demonstrate. Me saying I'm your fan means nothing, but I'm going to demonstrate to you that I am

• 23:48Speaker 02

  in your corner and I am trying my best to help you succeed in every way you want to succeed. And when you have that in your corner, it's wind, wind at your back and you'll do anything for people that are great fans of yours. And we all want parents and coaches and teachers that are great fans. And many of them aren't, unfortunately. They just don't have that in their head. In fact, they think it's about demand and challenge and a lot of other things, of which there's places for those things. But, but at the end of the day, the composite view, are you, are you rooting for me? Are you my fan or, or, or less so? And, and my ability to stay committed and loyal to you and reciprocate that support is a function of how you demonstrate it to me.

• 24:31Ryan Holiday?

  Yeah, we told the story in the daily dad email a few months ago about Jim Vavano, the basketball coach. His father, Vavano, as a kid, had said to his father, "I think I want to be a basketball coach. That's what I want to do." And so the dad says, "Yeah, sure. That sounds great." You know, and he thought it was the end of the conversation. The next day, Vavano's father calls him into his bedroom, and there's a suitcase packed on the bed. And Jim says, "What's that?" And his dad says, "That's my suitcase. It's packed and ready to go for when you when you coach in the Final Four." And I can just, it gives me goosebumps to think about that, to think about what that must have meant to a kid, right? That

• 25:15Ryan Holiday?

  your dad would do a demonstration so, sort of so clean and simple and earnest that like, "I'm in your corner, and I want to help you be successful." It's just a beautiful thing.

• 25:30Speaker 02

  Beautiful is exactly the right word. It is beautiful. Right? And when you have that, and you experience that level of fan-ness, and you want to do it for other people, and by the way, that's your job as a leader. And if you can't be my fan, you should not be leading me. Okay? And by the way, if you can't be my fan, and I'm your child, right? Or I'm your spouse, you shouldn't, you shouldn't have gotten in this contract with me. Sure. Right? And so that's your job. And good days and bad days. Now, most of us can be fans when things are going well. Right. When good grades come home, when the marriage is, you know, wonderful and so forth, when the team is performing. The question is, your job is to be and show fan-ness, right? Independent of good or bad outcomes, right? Your job is to be that fan, because that's what leadership, in some aspect, not all of leadership, but

• 26:15Speaker 02

  some aspect of leadership called motivation, inspiration, that's what it requires. And the more that you can develop the behaviors and the routines of fan-ness, of which we know, like, 48 of them, that we've been able to uncover, then the more you'll be able to demonstrate that to people, and create and motivate and inspire people without having to know exactly whether they're coin-operated, or whether they like, you know, to be threatened, or whether they really like autonomy, or they want mastery, or they want purpose, they want higher, like, I like all those things. But I want a universal, where I know that I'm going to show up anytime, any day with anybody, and I'm going to be more inspirational and motivational, and I know it's fan-ness. And if I can demonstrate fan-ness, that's what gets produced.

• 26:59Ryan Holiday?

  Here's a situation I saw someone mention, but I've struggled with it myself. What do you do? I found myself, especially with some young people that I've hired. I found myself saying these words like, I can't want this for you more than you want it for yourself. So what do you do when you are a fan of someone? You do want them to be successful. You are rooting for them, but they seem to be stuck in some sort of trap of self doubt or fear or laziness or entitlement. What do you do when? How do you get people to rise to their level of potential or excellence?

• 27:39Speaker 02

  So you shake them up, but shaking them up doesn't, isn't necessarily a negative. Right? There's lots of ways of shaking people up. Like sometimes it's around, it's about putting them in the right context so that they're able to succeed at a higher level. Like, for example, you probably know this, but I work with lots of college golf teams. And one of the things I like to do is I like to take the teams a couple of weeks before they, you know, have a big tournament. I like to put them on a course that everyone's going to shoot 63 on.

• 28:04Ryan Holiday?

  Yeah.

• 28:05Speaker 02

  Like the whole short course, it's easy course, and they're all going to just shoot this really low number. Okay. And then they go like, wow, like that felt really good. Damn right. Okay. And by the way, it's not going to be like that in a couple of weeks. So that's the last time we're going to do that. But I want to pump you up. I want to, I want to shake you up. I want to, I want to get your confidence as high as I can get it as an example. Or it might be that I just need to put you in a situation where you can demonstrate your skills and your skills will be more rewarded, not just by me, but by other people. You know, you'll be able to compete in a different way. Or, I mean, there's so many ways that I would probably try to shake somebody up. It would depend on that context. But, but at the end of the day, that's what's going to be in my head. I want, I want to, I just want to just, you know, just to give you superlatives and try.

• 28:49Speaker 02

  I want to shake you up. I want to, I want to create a context by which you can come to see yourself differently, or at least see yourself more like I see you, which is very capable. I'll tell you this, I give you an example. I have a very talented person in our team. And for whatever reason, she goes in and out of confidence, in and out of confidence. And, you know, I've tried lots of different things. Well, I had a very honest conversation with her the other, you know, about two or three weeks ago. And she was shocked by it, by the way. And I'll tell you how it ended up. But what I said to her, I took a chance and I said, you know, I feel insulted by you. And she said, what do you mean? I said, I have all this confidence in you more than you have confidence in yourself. But what you're telling me when you lack confidence in yourself is that I must be stupid.

• 29:31Ryan Holiday?

  Right.

• 29:32Speaker 02

  That my confidence is unfounded, that I must not be a good judge. And I, I just, I find that insulting. She said, it never occurred to me that you could be insulted by my lack of low confidence. And I go, I, I think the world of you and have invested a tremendous amount of resource. And here you are undermining yourself and you're, and you're, you're basically calling me stupid. And she said, seriously? And I said, not completely, but mostly.

• 29:55Ryan Holiday?

  Yeah.

• 29:55Speaker 02

  And I said, you gotta stop it. And believe it or not, that was the thing that shook her up. And now she goes, listen, if, if Randall thinks that I, that highly of me, I better start getting on the, on the train. I better think that highly of me because if I don't, I'm basically not believing in him. And I believe definitely in him. And by the way, I, I like that conversation a lot because it made me feel good. Right? But, but at the end of the day, you gotta shake people up because you can't let them stay in this place where they are underperforming based on what they're, what's capable, they're capable of, because they simply lack a view or a perspective or a context by which they can assess themselves more objectively.

• 30:35Ryan Holiday?

  Well, and to go to the, go to the conversation you just mentioned, that's another example of giving up power. You're not saying, I'm the leader, I'm the boss, you need to change how you think. You're actually flipping it on its head and you're saying, you have power over me because I feel insecure or doubtful, insulted by how you're choosing to see yourself. And it's forcing them into the position of going, oh, I have to step up, be confident, believe in myself. So I can be there for Randall.

• 31:07Speaker 02

  Exactly right. Sneaky, isn't it?

• 31:09Ryan Holiday?

  Yes.

• 31:09Speaker 02

  By the way, all, all great leadership is sneaky. And, and I don't mean sneaky in a manipulative deceptive way, sneaky in the sense of its subtleties, its nuance. And the nuance that you, that, you know, that you and I are sharing, there's lots of other nuances, but one of them is giving up power. You gotta give up power to, to, to, to be powerful. And just like, you know, if you, if you hold a ball really, really tight, you, you, you, it, it, you won't have control over the ball. The tighter you control, you, you have a grip on that ball, the less control you have over that ball. The same thing's true in human behavior. The more, the tighter you hold things, the less control, the less influence and the less effectiveness you're going to have in that situation. Which is counterintuitive.

• 31:51Ryan Holiday?

  I saw someone mention this, so I'm glad you brought it up. What is the line distinction balance between sneaky and manipulative? Because there are other leaders who, you know, that they're sort of playing this game or they're trying to pit people against each other or trying to sneak this. Like, how does one sort of do the jujitsu that you're talking about without that bleeding over into a kind of manipulativeness or Machiavellianism or what have you?

• 32:21Speaker 02

  Positive intentions. Where are your intentions? At the end of the day, I can't judge you for anything other than that. I can't, I can't judge only the outcomes because, you know, those happen. Those are moderated by other things, right? And I can't judge perfectly your character, generally speaking, because that may apply, not apply in this moment. What I can do is say, from what you've demonstrated, what you said, what you did. And by asking you, what were your intentions? And how positive were they? And how much were they about you or how much were they about me? And were those, were those intentions pro-social? Were they things where you actually thought that would help? Or was this about you, right, getting your way? Because when you're manipulative and deceptive and sneaky in a negative way, it's because it's about you getting your way. Okay.

• 33:02Speaker 02

  When you're, you know, when you're clever and industrious and creative and sneaky in a positive way, you know, you're, you're being intentional in a positive way to other people. So it's all about intentions for me.

• 33:15Ryan Holiday?

  So this idea of being a student of leadership, obviously you've had now four decades of actually being in the room where things are happening. Are there any leaders you think people should study or know about, perhaps ones that they don't know? And, and what would be some, some books you might recommend to aspiring or struggling leaders?

• 33:38Speaker 02

  So, so, you know, I don't even know how, how to take that question because I hold the opposite view. I don't want anybody holding up leaders to study or emulate. And the reason is, and I want to correct that in a second, but the reason is this, we make heroes out of people and they disappoint us. Right. They're never as good or as flawless as we'd like to make them. They're always going to get us in trouble and they're always going to do things because they're human. We're all flawed. So, so it's time for us to stop celebrating people and celebrate actions and behaviors instead. You know, I'm not a big fan of Steve Jobs for, for what I know and how I know and so forth and so on. But he's, he's got a couple of behaviors that I, I teach everybody. Sure.

• 34:18Speaker 02

  And, and I don't have to tell them they're from Steve Jobs. I don't tell them, I never tell anybody anything where they're come from because it's irrelevant where they come from. We should hold up the actions of great leaders, the judgments of great leaders. So let me tell you this, for example. Imagine that we started a dialogue together and it's something where we, we, we expect that, you know, we, we haven't been, we haven't found common ground before. This is going to be a difficult conversation. Sure. And the like, but I want to have an open and honest conversation. Imagine I say to you, okay, I want to commit to you right now that I, that I acknowledge that I could be entirely wrong about, about how I see things. I just want to start there and I'd like, you know, I'd love for you to reciprocate. I'm not going to require it, but I want to start with this place.

• 35:01Speaker 02

  It says, I, I acknowledge that I might be totally wrong and I'm doing so publicly in front of you or in front of this team. Okay. Now let's have a conversation from there. What impact do you think that has on the openness or the, or the, or the transparency of that conversation? I think it has a lot. It's very disarming. I think it's a very wonderful thing to do, especially in, in high conflict situations where, where people are more likely to dig in and be big advocates for what they believe and don't believe there's anybody else. But when you start there again about you, right? Well, guess what? You know where I learned that from? One of the few things I learned from Abraham Lincoln. But I don't call it the Lincoln thing, right? And I don't hold up Lincoln because by the way, like, you know, Lincoln's son hated him so much. He chose to end the generation.

• 35:45Speaker 02

  Right? The Lincoln died with his son because he hated his father so much because he was ignored as a kid and chose never to have offspring on purpose. Not a flawless leader. I'm sure glad Lincoln existed though, by the way, and I'm sure glad he was what he was. Probably Mary Dodd didn't, probably wouldn't agree with our general view of, of Abraham Lincoln. But there's things we can learn from people. It's time to celebrate actions, the behaviors. Instead of people, people are always going to disappoint us. They're flawed. Sure. They're always going to get us in trouble. Somebody can have integrity for 55 straight years and lose it one morning. Okay. And by doing the wrong thing and engaging in the wrong action, I can't stop that. But what I can do is stop worshiping them. And I can start holding up their behaviors

• 36:28Speaker 02

  and say, here's something I can learn and apply for the rest of my life. And it doesn't matter it came from Abraham Lincoln or Steve Jobs or wherever it came from. Okay. As an example.

• 36:41Ryan Holiday?

  Here's me talking to the one and only, the GOAT, greatest of all time, Robert Greene. I was thinking about our joint experience at American Apparel, which featured both a character of this type, but also a lot of sort of real world's hard choices, because thousands of people's jobs were at stake. There was, you know, we had some influence over this and no influence over that. Now with some distance from American Apparel, where for people who don't know, you were on the board of directors for many years and you knew Dove, the founder, quite well. You watched this company go from a tiny little company to a publicly traded company to one of the hottest fashion brands in the world

• 37:23Ryan Holiday?

  to an unceremonious exit when the board fired Dove and then a whole bunch of drama and chaos and, you know, lawsuits to this day. So as you think about that situation, how has it informed your understanding of human nature, power, strategy, and dealing with difficult people?

• 37:47Robert Greene?

  Well, it brought a bit of humility to me. So, you know, I'm not perfect and I misjudge people. So as I said, it's okay to make mistakes in life and that was a mistake. But first of all, you know, part of it, you have to understand Dove, who was a very charming person, very seductive in a way, very charismatic. And it's very easy to get caught up in those with those kinds of people. I will never let that happen again because I learned I was burnt by it. And so I kind of identified with him and I saw that the future of the company was tied in with him, which it was to a large degree. But, you know, so certain

• 38:32Robert Greene?

  signals were sent that we should have all picked up earlier on and we let it drag on a little longer and then we ended up firing him. But it's not all bad on my part because the act of firing him took incredible amount of, I'm not gonna say courage, but something similar to that because he was a friend, he was close, he trusted me, you know, and I was basically the one along with another person on the board who was pretty much responsible for that. It was very difficult. I felt like I was a traitor, like I was Judas, like I was, this is a man who built the company and I'm gonna destroy him, but it was the right thing to do because he was taking the company down with him.

• 39:15Robert Greene?

  And so, you know, I got my act together. So personally, it was humbling to realize that I misjudged people, that I, the writer of the Forty Eight Laws of Power, et cetera, has an Achilles heel, that when people are charming and seductive and complimenting you, because he loved the Forty Eight Laws of Power, it drew me in, all right? I learned from that, but I also learned that a time comes when you have to make a decision and the decision is going to be hard and there are going to be terrible consequences, consequences that I'm still living with, as you know, Ryan, to this day. But I think, you know, at some point, you have to like kind of come to terms with your

• 39:55Robert Greene?

  own, you know, flaws, which I did, and then make the right decision. So, I mean, there were a lot of things that I learned from that. I learned a hell of a lot about why business is so screwed up in America right now. It was an amazing experience, but when it came to Dove, those were sort of the two main lessons.

• 40:15Ryan Holiday?

  One of the things I think about when I think back to that time, and I wonder why it sort of took so long, like on my own part, like why, why did I sort of, I guess, I guess what I'm saying is why did I feel I was so powerless? And I know to a certain degree I was powerless, but there were things I could have said, things I could have done, decisions I could have made, things I could have dug in on and fought harder either for or against. And in retrospect, you know, what was I afraid of? Maybe I was afraid of losing my job, but that would have happened anyway, and it did happen anyway. And I would have landed on my feet and been able and been prouder of myself if I had.

• 40:55Ryan Holiday?

  So I guess what I sort of look back and I wonder why you were saying that it took courage or that it was scary to do. Why are people and maybe why were we so hesitant to make hard decisions sooner? Like, why do we, why do we push them off? Why do we lie to ourselves about them? Why don't we just do the hard thing earlier and sooner?

• 41:21Robert Greene?

  Because it's very painful. So I can't say about you, but I can say about me that I was a friend, that I had violated law number two of the 48 laws of power. I had mixed friendship with business.

• 41:35Ryan Holiday?

  Never put too much trust in friends, learn how to use enemies.

• 41:38Robert Greene?

  Exactly. So, but the thing is, people don't understand that business is not, is not just this game of who's socially, who's virtuous and who's not. It's, it's a numbers game, right? We had 17,000 employees whose future was at stake. And we had a CEO who was unhinged and he was making irrational decisions. But it wasn't black and white about firing him and being a good guy. Because what was going to take over? If your main goal was to protect the company and the shareholders, which was my job as a member of the board of directors. It's easy to fire him, but who's going to take over? The person who takes over could make the company even worse and can run it into the ground.

• 42:23Robert Greene?

  Dove was the only person who understood the brand. He was brilliant at that. So you bring in some corporate, you know, flack to take over the company. They're gonna, they're gonna make it worse in a way, which is what ended up happening. When the, you know, and I don't regret my decision at all. But ended up a giant billionaire's hedge fund took over the company. People who had no idea about the fashion industry, who were like heads of Radio Shack. Oh, right, there's a good connection between Radio Shack and American Apparel. And they made the worst decisions and they ended up destroying the company. Dove would have destroyed it anyway. But it's not just black, it's not just, oh, I've got to be brave and make the right decision because there are other people involved in it.

• 43:09Robert Greene?

  So I had to consider all of these other parameters. So in the time when I should, we should have maybe fired him earlier on. I was very wary of what would the alternative be? Because I looked around at the board and I saw people who knew much more about finance than me, but who understood nothing about the business itself. And I didn't trust that they were going to make better decisions. So, you know, when you look at the news or you read the news, your tendency is to say, this is the villain, this is the hero. But it's never like that, right? There's more at stake than that. There's more to the story than that.

• 43:43Ryan Holiday?

  No, I'm really glad you bring that up because there's one, a very specific thing about American Apparel, which I imagine figures into your calculation. It was also about when does the people who want to do the right thing to go, what we were talking about earlier, have the leverage to be able to actually do it? And if I remember correctly, part of why the decision actually happened when it happened was that due to some financial decisions he'd made for the company, his ownership stake was diluted enough that the board finally had the power to be able to make a decision that if it, all things being equal previous, may have made sooner, but, but wasn't feasible to do it.

• 44:21Robert Greene?

  That's, that's precise of it. I'm so glad you brought that up. I, I forgot to mention that, yes. The moment it dipped below 50% to 49.9, that's when we made our decision. Because if we had done that before, prior to that, he would have fired all of our sorry asses. He would have stacked the board with his own cronies, which believe me, he would have done in a second, no matter if he thought of me as a friend or not. So yeah, we waited till exactly that moment when he had diluted his share of the company to under 50%.

• 44:51Ryan Holiday?

  No, and, and then this point about it not being sort of villain or hero. I think about this with Seneca, you know, Seneca being this brilliant philosopher who's then in Nero's court. And some of the Stoics were part of what they called the sort of Stoic opposition or the Stoic resistance who resisted Nero at every turn. But, but Nero, but Seneca was the opposite. Seneca worked in Nero's court and.

• 45:15Robert Greene?

  He was his tutor.

• 45:17Ryan Holiday?

  Yeah, and I think about there are some other ones who advised Octavian, Arian, sorry, Arius, Didymus, and Athenodorus. And in retrospect, it seems hypocritical, the Stoics were Republicans, why did they support the emperor? But they were also very aware of the costs of Rome's prior to civil wars. And they had to make a judgment call of, you know, is it, we might be morally correct, but the carnage from that moral decision would be immense. And I think when you look at the American Apparel situation, the decision was the right one, but it still didn't work out, right? Like, the thing that everyone was trying to stave off still happened.

• 46:01Ryan Holiday?

  And so, people who are maybe one of the downsides or upsides of the 48 laws of power, when you have a sense of how history works, and you have a full sense of the picture, it makes it much harder to be morally certain about what you're doing, because you know that it's more complicated than that.

• 46:18Robert Greene?

  Yes, I mean, at a certain point, the two kind of collided in an interesting manner. So, we always knew that Dove had this other side to him that was very, very questionable. And in the world today, the Me Too movement, he would have never survived, you know, past 2018, even if he had stayed on, right? Okay, but we couldn't fire him because he controlled the company, he would just get rid of us, and he would run roughshod over the whole thing, okay? And then, but we knew about his character. And so, at a certain point, when the power game switched, and he was in a weaker position, then we could get the moral high ground and fire him.

• 47:03Robert Greene?

  But then, as you say, it got complicated, because what comes after this, right? So, what comes after Nero? I mean, who came after Nero? Was it Caligula?

• 47:14Ryan Holiday?

  No.

• 47:15Robert Greene?

  No, he was before. It was...

• 47:18Ryan Holiday?

  I think like five, four or five emperors come after Nero.

• 47:21Robert Greene?

  Right, right, right. Right, and some of them weren't even any better than Nero. And supposedly, recent books have been written that Nero wasn't as evil and dark as history has made out to him, that some even people claim he was even actually a relatively competent leader. I don't know which side that is, which side to fall on there. But, you know, what were we going to do afterwards? What was the end game? Because it's great to moral grandstand and say, this man's evil, we got to get rid of him. But then you have to live with the consequences of that. Now, I subsequently got fired from the board of directors by this hedge fund, right? So it was kind of taken away from me. But for that interim period of a couple of months, I was actually in charge of trying to find who would replace Dove.

• 48:05Robert Greene?

  So it's never that simple where it's like good versus evil, right? You can take, this is a main thing in the Forty Eight Laws of Power and in Thirty Three Strategies of War, you can be the kindest person, you can have the best intentions of all, and your decisions create havoc and create the worst kind of evil, unintended consequences, right? We see that play out over and over and over again in history. So, you know, this is an example where it's not just about doing the moral thing in the simplistic way, it was about what are the consequences? What's the long-term picture here?

• 48:40Ryan Holiday?

  Well, and that goes back to this idea of courage, and I talked about this in the new book a little bit, which is, you have to have the courage just to decide and then to own your decision and the consequences of that decision. And I think that's one of the reasons that people don't do things. They hesitate because they know if they break it, they buy it, if they sign, leaders want to have it both ways, when really courageous leaders know they have to make the decision and then then stick to executing the decision with competence, as we said. But then you're going to have to own the fallout, the criticism, you know, the consequences. You can, you could have made the right decision with the information you had at the time, and it can still go horribly wrong.

• 49:21Ryan Holiday?

  You can be morally correct and still be, look like an immoral person. I mean, I think we're looking at this in Afghanistan right now. Extricating oneself, extricating a country from a country from a war that's gone on for 20 years, it's gonna be messy and unpleasant, and it's not gonna look good, and it's gonna reveal a lot of things that have, you know, predated your decision. And I could very much see why a leader would waver or change their mind under the public pressure that comes from that. But you got to, the job of being president, or leader, or CEO, or board of directors is making hard decisions and then, you know, shepherding them to completion.

• 50:04Robert Greene?

  Well, you know, people very rarely like to take responsibility anymore for their decisions, right? So as you say, they want to have both ends. They want to appear like they're doing the right thing, but not really make the tough, hard decisions. And, you know, I mean, you wrote a whole book on, a brilliant book about that. But, you know, when you take Afghanistan, for instance, yeah, that was a very ballsy thing to put a deadline on and say, look, we're getting out. This is it. We have to do it. Right? And that takes courage because he's gonna pay the consequences for that. But the way that it was done was not very thoughtful. There's not a lot of forethought into it,

• 50:48Robert Greene?

  the unraveling of it. So here you have the right hard decision, but it's not executed well. So this goes into something about the 40 laws of power and leadership. So making

• 51:00Ryan Holiday?

  Plan all the way to the end, right?

• 51:02Robert Greene?

  Yeah. So making the hard decision isn't necessarily enough, because you have to now think of what are the consequences going to be? And I'm gonna have to own those consequences. Now, unfortunately, how Biden has to own the consequences of this kind of hasty withdrawal. I don't want to play Monday morning quarterback. It was very, I don't know if I would have necessarily done better. But I talk to people I consult with all the time, and the weakness that most people have is they never see far enough. They don't game out the possible negative consequences of their great or hard, their decisions, right? They see only, I do this, and this will result. Whereas there's this, and this, and this, and all these other

• 51:44Robert Greene?

  possibilities. You have to think of the worst case scenario when something happens. So when I, we fired Dove, what's the worst case scenario? It ended up, what my thought, my worst case scenario ended up happening? Which is it's taken out of our hands, a hedge fund comes in and they completely mess it up by bringing in people who don't understand the business, right? So, you know, leadership is is a much more complicated thing than people think about, right? I think they tend to simplify things too much. But the art is not just making the right decision, not just making, having the right strategy, but playing the aftermath, what will happen later, what are the consequences can be?

• 52:27Robert Greene?

  You know, you can have period victories, you can win, but you can go too far and end up kind of leaving yourself vulnerable, et cetera.

• 52:34Ryan Holiday?

  For the last two years, we've been doing this thing that we call the Daily Stoic New Year, New You Challenge. It's 21 actionable challenges, one per day, built around the best Stoic wisdom, but for what? How to be better in the new year. This is the time when we start to think about what we're going to do next, where all the time went, what we wish had gone differently or better, how we're still struggling with this or that, how we'd like to to stop doing this or that. And that's what the New Year, New You Challenge is all about. It's my favorite thing that we do, and it's three weeks of actionable challenges presented in one email per day, built around the best, most timeless wisdom in Stoic philosophy.

• 53:16Ryan Holiday?

  It should help you snap out of this trance we've all found ourselves in and help make 2022 your best year yet, no matter what's happening in the world around you. Go to dailystoic.com/challenge to join us. I'd love to have you. I'm challenging you to join me. I can't wait to see you. Dailystoic.com/challenge. And here's me talking to my friend Jenny Britton Bauer. I was gonna, I was gonna ask you, and, and, sorry if I missed anything, but, so, so the first business, what is it, screams, ice cream? It doesn't work out, right? So, so walk us through some of the lessons that you took away from, from that. I imagine that must have been a bitter pill to swallow and not fun.

• 54:03Speaker 04

  Yeah, it was because I had a business partner and she was a wonderful person, but we didn't have the same, just we didn't share the same opinion about the business. And we had this agreement that we were like 50 50 partners. And then we were going to like, close that one and then grow and then go start another company or, you know, get out of the farmer's market and go do it bigger or something. I don't know, you know, even though we had totally failed in the market, we were going to like restructure and go figure it out. And her parents were going to give us money to do it and whatever, whatever. Well, like she wanted to, she didn't want to like share, you know, give me like my side of the company, even though I had worked every single day. I knew she had never worked at the company. It was all my thing, all my ideas, all my flavors. The whole original concept was mine.

• 54:45Ryan Holiday?

  Yeah.

• 54:46Speaker 04

  And so I had to walk away from her and that, and they were going to still do it. And so I literally like, like just walked away thinking that was the end and that they were going to take all my ideas and do it. And when I say they, it was like, there were three of us. This other guy, food scientist had come in and he was awesome. He was our age and we were just all three going to do it. We couldn't figure out the partnership. So it was really hard for me in that way. And I had to like sort of start over and I thought, well, she's going to do it. And, you know, that was the risk that I took and I just need to go and do something different. Well, I didn't see her do it after a few months. And so then I started working on a business plan, but the whole time I thought, well, they're going to launch something soon and I won't be able to. So, um, but, you know, they didn't because they didn't know how to do it like I did. And, um, and so I started working on a business plan and figured it out and got back into

• 55:30Speaker 04

  business and, uh, in the back in the North Market in 2002. But yeah, it was hard. It was hard and a couple of reasons too. I mean, that and also just you, you think you're doing things right and then it takes some reflection. I mean, it takes a year or so of reflection to realize all your mistakes so that you can then fix them, you know? And what I did was I started thinking about what brought me back to other businesses. And I realized the only thing that brings me back was the, what I had the last time. And at Scream, I was always making new flavors every day or whatever I felt like making or whatever was in the market. I didn't have any like consistency. And so that was the big problem. One of the big problems at Scream, the biggest one, when I, when I learned that, then I came back as Jenny's and had like signature flavors and always had them in stock. And then that brought people back.

• 56:12Ryan Holiday?

  Yeah, that was one of the things we talked about with Robert Greene, who I know you and I have talked about before. It'd be wonderful, of course, if like you just, all business was, was having a good idea, being really passionate about the thing. But of course, then there's also dealing with people and partners and investors and I'm sure landlords and suppliers. What is, what has your experience been just sort of having to figure out like the political side of things, the interpersonal side of things? Like, I'm sure you'd rather just, you know, be with your flavors and your ideas and your

• 56:52Ryan Holiday?

  customers, but you know, there's a lot that goes between, that gets in between us and the thing we really like doing as leaders.

• 57:01Speaker 04

  Yeah, and I mean, that's, you know, yeah, it's, that's the hardest part. That is the reason that I love, I was just saying, I love the word company more than business because business is like the structure of disciplines, whereas company means that you're not alone, it's your fellowship. And so when, whatever it is that you make, it's, you, it's determined by that, the, the strength of your fellowship. And, and so it is, it's like really where all the work has to go is in the people that, that are supporting you. And if you're sort of a creative founder, the more, I, I, this is going to sound, it's, I have two ways of saying this, I mean, the more support you, support you have, you know, people who can lift up and support you in the ideas, the better you'll be. However, you also have to have people, the same people have to be able to challenge you, you know what I mean?

• 57:45Speaker 04

  So it isn't like just yes, yes, yes, and you know, like we'll go do this. I mean, it has to be a group of people who like support the ideas, not just, you know, the human or whatever, but like, and then you have to earn, you know, your place at table and support them back and all this stuff. But it really is about, it's about people before it's about anything else because you can't make. You can't make a great ice creams unless you can actually deliver it.

• 58:05Ryan Holiday?

  Yeah, sure.

• 58:06Speaker 04

  That works. So

• 58:07Ryan Holiday?

  Yeah.

• 58:08Speaker 04

  All the things that are, but yeah, you know, I mean, law and fairness and all that stuff. It gets in the way. It's tough. You know, but um, but you know, honesty and just bringing it in. You know, I find negotiation isn't really that hard because you just, you just, you know, you always willing to walk away and just, and just, and just put everything on the table. This is what it is. Honesty.

• 58:28Ryan Holiday?

  I'm curious in a business like yours, is something I've sort of experienced with Daily Stoic too. And I think it's more of an issue today than it was, let's say, 20 or 30 or 40 years ago. Because customers want it. And then also, I guess we have more choice, but like, you know, it would obviously be cheaper and more effective, but let's say efficient, for you to, you know, use, let's say, lower quality ingredients to not care about sort of the ethical side of things. Right? I think one of the important parts about Stoicism is it's not just a framework for like, how do you achieve success? But it's also, how do you achieve success within sort of a, a set of boundaries, sort of ethically, how we relate to the planet, how we relate to other people?

• 59:13Ryan Holiday?

  How do you think about, I've got to imagine the kinds of ingredients you do, the sort of commitments you have, the certain kinds of quality and freshness and, and, and all of that. I imagine that costs you in a lot of ways, right? And, and how do you think about, you know, the balance between staying afloat and, you know, your sort of, your absolute highest standards? How do you think about what's non-negotiable and all of that?

• 59:42Speaker 04

  Yeah, I mean, I, I often think about a company kind of as a garden, you know, and you have a limited resources to, to make that, that garden beautiful. And, you know, over one, one side, it's lush and green and gorgeous. And on the other side, it's wilting and, and drying and, and dying. And, you know, you're always, and then there's everywhere in between, and you're always trying to stretch your resources and do everything you can. I mean, obviously, you know, there's no such thing as just this perfect Eden of a company. You know, you're, you're always like, you know, putting out that fire and then, and then running to that one. But I do think that, um, Like we're a certified B corporation. I think that that matters so that we, you know, it helps us focus.

• 1:00:20Ryan Holiday?

  What does that mean exactly?

• 1:00:21Speaker 04

  It means that we're certified by a third party called the B lab for environmental accountability and sustainability and a whole bunch of other issues like pay, fair pay and diversity and all sorts of things. And so you get a number every year and you're expected to grow that number. And that helps, I think, a lot because it gives us, well, first of all, it sort of puts that in our scope of and gets that gives us like a plan of, and you can choose, you can't do everything, but like, and it also shows, because right now it's like, everybody wants to say that they're, you know, this good company or whatever, but it really can show the world that, you know, what we're trying to do. I think we would be doing this whether or not we could get certified. In fact, we were, and then we decided to get

• 1:01:06Speaker 04

  certified and we applied and made it about 10 years ago. But I do think that like, you know, it's one of those, it's one thing to say it and it's another thing to do it.

• 1:01:16Ryan Holiday?

  Sure.

• 1:01:17Speaker 04

  And then the other way I think about this, yeah.

• 1:01:19Ryan Holiday?

  It's another thing when you're, when you're like getting a quote on something and you're like, hey, I want to make this in the US. And you're like, but let me get a quote and see what it costs to make it in China or whatever. And you're like, oh, it's four times as expensive to do it the way that I want to do it ethically, right? And then you, then you realize that these, these questions, whereas like as a customer, as a writer, as a outside person, these are all abstract ideas. And of course, you know, one is preferable to the other. But then, yeah, as a leader, you have to make those actual hard decisions of signing the checks.

• 1:01:54Speaker 04

  I mean, we, like I mentioned, a hundred million dollar company, we have an $800,000 marketing budget total. We are like, we're a creative company and that includes like pay, you know, like our team. We have a really small team. We don't overspend, we don't really spend very much on marketing at all. It's word of mouth, it's product, it's all of that. And that's, that, you know, I think that, yeah, there are trade offs. And for us, it's like, you know, well, we better be the most creative then and, and get some attention that way or whatever, so that we can bring people in. And you'll notice too, if you get our, get to our shops, they're very simple. They're not overly like, we don't even really work with, I mean, we just design our shops. We design and build them. They're not like fancy or super, super branded or whatever. They're all a little different.

• 1:02:35Speaker 04

  And so, yeah, I mean, you know, it's really for us, it's about ice cream and people. And then, of course, you know, I mean, I think, I think when I think about ice cream, I think the experience. So it's service, ice cream and art and design. And then everything else that we do all of that in-house and everything else is, you know.

• 1:02:51Ryan Holiday?

  Wait, I think people, I think, I think it's a really important point, which is that. Yeah, like when you look at a company that, you know, outsources their labor or uses really cheap ingredients. And, you know, a lot of them are publicly traded. So you, you look at them and you go, well, you know, they're paying a fraction of what we pay to make their product. But their margins still aren't great, like their margins aren't amazing. What, what is it? And you realize, oh, they're, the margins are eaten up in their enormous corporate headquarters. Or, you know, their celebrity ad campaigns. And so I think as a leader, you have to figure out like, here are my non-negotiables. Like, here's what I actually care about. This is what's going to be the biggest line, the items on our P and L.

• 1:03:35Ryan Holiday?

  And then we're going to have to make steep cuts, as you said, in marketing or in, you know, how fancy our office chairs are. Because one is much more important to us than the other.

• 1:03:47Speaker 04

  Yeah, and you know, I, I, I mean, I really, really, yes, I, I agree with that. If I would have taken money earlier, we would be a very, very different company. I mean, I probably would have, you know, pitched us building some kind of, you know, big production facility with like, you know, grass on the roof and cows grazing. I mean, I don't know, you know, like the place, like you could bring a family in a school bus and whatever. You know what I mean? Because I thought like, that's what we needed. I, I would have just done things so differently. But instead, we just did it in a really scrappy, really, really scrappy way, taking out loans, you know, from the SBA until about 2016, when we finally took on partners. But, you know, that was a long time for us to build that brand.

• 1:04:27Speaker 04

  And we still just are really, really, really scrappy, as you know, and like, I just feel like you can't, if you're doing, you know, I, I like to call myself a start small and build entrepreneur. And that's sort of in contrast to like pitch and launch, you know, start big and build. The idea that like if I would have done that is this as a pitch and launch company, it never would have worked. Like even if people had been like, yeah, you know, I think ice cream could make a huge comeback in America and American ice cream could be the best in the world when done properly and blah, blah, blah. And I think that is a really big opportunity, even if we could convince somebody of that, like just building the community around what that ice cream is and around $10 a pint ice cream, like it's been such a challenge. It's been like that's that needed all of this time in order to build everything. And that's, that's why it's like, it's like a snowball. Now it

• 1:05:11Speaker 04

  keeps going, but, um, but it took all, all of that, you know, you can't, I don't know, it's just, we, we grew kind of like scaled up the stuff that, that worked and then like things that didn't, we left, we left behind. And that was a slow process versus like trying to like, figure this out and then launch and then, you know.

• 1:05:32Ryan Holiday?

  I think that's really, I think that's really important. You should, people should do some, I, I think most personality tests are bullshit, but you should kind of figure out that, are you the kind of CEO that wants to be sort of hands on and making stuff? Or are you the kind that's really great in meetings, really great raising money, really great selling a vision? Because they're not the same thing. They're sort of a maker and a manager type, like which are you? And like, if you're a maker and you sign yourself up for what's primarily a sort of a management style business, you're going to be very miserable. If you're a management style, but you know, management style, but you actually have to go make the thing, you've also probably promised something that you can't possibly deliver. And so really knowing sort of what your strengths are and also like how you want

• 1:06:17Ryan Holiday?

  to spend your days, like what do you want to be doing? I know so many people that have had a good idea, then they've ended up sort of committing to or selling this thing and they just hate their life because it, it's actually taken them away from what they wanted to be and what they want to do day to day.

• 1:06:37Speaker 04

  And I wonder also a lot about the role of a founder in a company now because I never wanted to be the CEO, not necessarily. I mean, I believe that I brought in a CEO because I wanted someone who could build safety in the company, who would protect, whether it's jobs or law or whatever, and somebody who really, truly understood that and that they were on the hook for the safety of the company. But I think that the role of a founder in every company is different. Maybe it is CEO in some places, or visionary. I think that's a real role. But I think that there needs to be a different way of looking at some companies where there isn't just maybe the CEO at the top. I don't know if I believe

• 1:07:17Speaker 04

  in like, shared CEO, because I think it's such a specific job. But I do think that some CEOs are visionary. And I think some companies at certain point can move into having a visionary CEO when the operations are figured out and when the team is in place and things like that. But I do think that you need a visionary all along anyway. And that's maybe a role that a founder can play. But a lot of times in business, especially in the sort of financial world, sort of business, founders are kind of just not seen that way, or they're seen as like, creative and then kind of put on a boat and let out to sea a little bit. You know, like, they're just not, they're not considered part. But that goes back to, you know, founders often know their customers better than anybody else. They know their product better than anybody else, and they have a vision for it. And God, they know their competitors more than anyone else. And so there is a role in the company for

• 1:08:02Speaker 04

  founders. But I know that we haven't, just in American business, figured that out yet.

• 1:08:07Ryan Holiday?

  Demand more of yourself in 2022. And one of the ways you can do that is by joining us in the Daily Stoic New Year, New You Challenge. All you have to do is go to dailystoic.com/challenge to sign up. Remember, Daily Stoic Life members get this challenge and all our challenges for free. But sign up, seriously. Think about what one positive change, one good new habit is worth to you. Think about what could be possible if you handed yourself over to a little bit of a program. We all pushed ourselves together. That's what we're going to do in the challenge. I'm going to be doing it. I do the challenges, all of them, alongside everyone else. I'm looking forward to connecting with everyone in the Discord Challenge, all the other bonuses. Anyways, check it out. New Year, New You, the Daily Stoic Challenge.

• 1:08:52Ryan Holiday?

  Sign up at dailystoic.com/challenge.