John McMahon (7:16)

Yeah, let's talk about that. In your book, you do talk about the fact that you're born into a lot a story, and you need to understand that story and how that story does affect you and affects your life, either in a positive or negative way. But being aware of it is so important. Can you talk a little bit about that, Doug?

Doug Holliday (7:32)

Yeah, I mean, it's funny. I think it's. To tell a story really puts a point on it. So Peter Buffett's a friend of mine, Warren Buffett's son. So Peter's telling me. So Peter says this. We're all born in someone else's. Story. And when he said that, huh, said Doug, let me tell you my story. He said, here I am, a sophomore at Stanford. The only reason I'm at Stanford is because of my last name. And he said, then my father famously announced that he wasn't going to leave the three of us anything. And that kind of sucked. And then he said, I'm there, you know, I'm doing finance and economics. I don't like it. It's not who I am. Then my mother calls a couple months later. Said, peter, your grandfather died and left you some money. Said, how much? 92,000. That day, Peter packed his car in Palo Alto, left Stanford and drove to LA to pursue his story, what he wanted his story to be, which was a musician. And Peter then did well in this, actually did part of the score for Dances with Wolves with one an Emmy. And so I was. I was telling him at one time, one of our later conversations, I said, peter, you know, in. In faith traditions, Jewish, Muslim, Christian, there's something called the blessing, where the. An adult or the elders say to you, you know, John, you have what it takes. It almost launches you as a male. I said, did your dad ever do that? And he thinks for a minute. He says, you know, it's interesting. He said, about five years ago, I was doing a show in Omaha. My father had never been to one of my shows. I look up in the back and there's my dad and Charlie Munger. And they come down and Warren Buffett puts his hand on Peter's shoulder and says, peter, we've both been successful in our own ways. I said, peter, you got the blessing.

John McMahon (9:34)

Yeah.

Doug Holliday (9:35)

So I would say to us on this call, many of us never got the blessing. Never a lot of us. Part of why we keep striving and working and accumulating is because we're trying to. We're trying to please some adult figure. You can't please some. Somebody that will never tell you you're enough. And I'd say to you, now you've got to pause and say, why the hell am I doing this? And. And look at yourself. Pause when you're lost in the woods. Step one is acknowledge your loss. Say, this is not working for me. And the problem is, if. If you don't understand this, you're going to replicate this with your own kids. The story you have seen. I said, my MBA students, how many of you grew up in raging families? There was a lot of anger and craziness. 60% raise your hand. I said, guess what? That's Going to be your family unless you take a hard look at that, make decisions to break those patterns. So, so this is not, this is not theoretical stuff. This determines your life. And if you doubt me on this notion of how these patterns that we've observed and lived into have affected us, you look at children who have been molested when they were young, you would think the last thing any of them would ever do with their own children would be to molest them. Sadly, a large percentage do. Why? Because it's familiar. Even though it was horrific, it was the way they connected with the most important caregivers in their life. So this is not theoretical. You've got to really get your head around this kind of stuff.

John McMahon (11:25)

Yeah. You talk about how some of these, some people, you know, had a career and they're lonely at the top. I was playing golf with a guy and I asked him about his dad and he said, yeah, you know, my dad was CEO of a company, you know, worked as, you know, non stop. That's all he knew his whole life. And he had tons of energy and he went, you know, 24 hours a day, seven days a week. But you know, John, you know what happened? My dad didn't retire from work. When he retired, he retired from life. He sat on the couch and less than one year later, he was dead. He had no hobbies, no friends, nothing. All he did was just work his entire life. He had no balance in that life, no meaningful relationships as you talk about in your book.

Doug Holliday (12:10)

Wow, that, that's a poignant story. I mean there's, there's so many stories like that. There was an ink study a few years ago. 3,000 CEOs of the 3,050% self reported that they're lonely and disconnected. These are, these are middle market and bigger companies. Of those 3,000, you know, 50% self reported they were disconnected. But 61% of the 50% said they're making bad decisions as a leader because they have nobody in the world they could trust.

John McMahon (12:45)

Doug, why is it that so many leaders get lonely at the top and so many leaders and sometimes it's not even the top, they get lonely and then they don't trust anybody. So they do make that. Why is that?

Doug Holliday (12:57)

Well, I think, I think you said it well, John. They don't trust anybody. And I mean this is true. I think what happens, the unintended consequences of success can be lonely and disconnected. So you can be the principal of a middle school or sheriff of a police force in a small town, and the same phenomenon is true There, you know, I don't have anybody in my life to talk to or trust and that kind of thing. Particularly with men, we're not taught. We don't have a language of the heart. So I say to men, you know, when you're out sometime and maybe you're walking or running in the morning and you see three women, typically they're talking. If you eavesdrop on their conversation, often they're talking about things that really matter. Men, by contrast, you know, I go off to play golf with Fred. Fred's wife died two months ago. So I'm playing golf, I come home and I say. She says, well, how. How's Fred doing? I said, fine. We had a good golf game. No, I mean, how's he doing since his wife died? Oh, it just didn't come up. Yeah, that is more true than not.

John McMahon (14:09)

Yes.

Doug Holliday (14:09)

You know.

John Kaplan (14:10)

Yes.

Doug Holliday (14:10)

And so I, what I say to people in our circle and Path north and others that, you know, we need to try to create a safe way that we can explore the most important things that many of us never have a chance to explore. So in my class, I frame it. It's an MBA class on meaning. And I have 10 questions you have to ask to have a life of thriving. And then I bring in rock star CEOs. I have the chairman of Johnson Johnson or JP Morgan Chase or some big hedge fund guy. And I know their story that illustrates that on risk, on failure, on relationship. And I tell you it's fantastic. But, you know, I didn't realize the most important part of that was for those CEOs. They're articulating things that they've never explored. And those students are asking them really probing questions. It's unbelievable.

John McMahon (15:12)

Hey, Johnny, you talk about in your book, to define success for people should be in human personal terms, not in individual personal monetary gains. And to concentrate on the human bonds that are forged. So in some ways you talk about what you call the double bottom line. Not only doing well and accumulating, but doing good and giving back and forging human bonds.

Doug Holliday (15:39)

That perfectly said, John. And you know, it's sad because we've got, It's a muscle. We have to practice. And I mean, the data is really interesting. So Vivek Murthy, who is the Surgeon General before the pandemic, he identified as the greatest health crisis in America. Not smoking, not obesity, but loneliness. I mean, who would have done that? When Theresa May was Prime Minister of England, she appointed a cabinet level position, a minister of loneliness. It's so epidemic in that Country.

John McMahon (16:22)

Wow.

Doug Holliday (16:22)

So there's a great story. Some of you could look this up. In England, they're called chat benches. So there was an elderly woman that kept giving money to this young man she didn't know. He would call her on the phone, give her this sob story. She kept giving her money, and eventually it was a meaningful amount. It was £35,000 she had given him. So the cops broke this, went to her and said, did you have any inkling he was taking advantage of you? She said, oh, yeah, of course I did. Well, why does he keep doing it? She said this. If I didn't talk to him, I. I wouldn't talk to anybody all day.

John Kaplan (17:03)

Wow. Yeah.

Doug Holliday (17:05)

So this cop started in the park. In fact, I saw one recently when I was in London, the community, this thing called a chat bench. It's a bench that said, if you want to talk, sit here. And then people just come and they sit and they. They can talk.

John Kaplan (17:23)

Amazing. Hey, Doug. In putting all these. First of all, your unbelievable background created all these experiences and all these relationships. And I find that the most successful people on the planet, in my opinion, are the ones who've made sense of their own stories. And so when I look at the book that you. That you put together again, it's called Rethinking Success, eight Essential Practices for Finding Meaning and Work and Life, you really kind of start with helping people identify, like, their definition of success. I think the first tenet, if you will, the first practice, if you will, is the illusions of success. And we're talking about isolation and loneliness. And you talk a little bit about, you know, and it sounds kind of biblical to me, like, people are made kind of perfect in their brokenness. And I. It's interesting, throughout your book, there's. I. I see references to Solomon and. And maybe on another podcast, we can go deep on that. I'd love to. I'd love to go there with you, but it's. It really lends itself in the beginning here on the illusions of success to this. This concept of authentic leadership, which I think is a really good topic for our listeners right now, because it's getting more and more rare. I talk about your experience with authentic leadership.

Doug Holliday (18:53)

Yeah, Here. Here's the problem. Having been in Washington, so the White House, State Department, all these things you see, all these fake apologies when people get caught. If I did anything wrong, you know, I was never. It's always just dancing around it. Here's what I found. People are drawn to authenticity. They don't want you to be perfect. They to want you, but authenticity is enough. So here's an example. You know, you kind of say, you know, this thing of being authentic and really being who you are. You know, there's that whole. All that body of research done on imposter syndrome. Most of us don't feel like. Feel like we're not as smart or as capable or as rich or talented as everybody thinks we are. So. So I say that our point of identity with people is not our strength. It's not how rich you are, how famous you are, all these acolytes. It is your brokenness. So I said this to my MBA class three years ago, and now imagine this. There's a young man on the front row. I said this. There's two things I say to start the class. That was one. I said, this is going to be real, guys. We're not playing games here. We're going to get down and dirty. This guy says, professor, I've been trying to get in this class, and I finally got in there because it's popular, not because of me, but because of the content. But he says, I really want to be real. And he said, I've had a debilitating stutter my whole life, which made me live in the shadows. I never had any friends, but I was very strong academically. And he said, a few years ago, here I was at an Ivy League school, sophomore. I decided I was going to take my life. He's telling us this the first five minutes, but before I take my life, I'm going to go out and talk to some people and try to speak to them. And I'm not going to be able to put. I'm going to be a laughingstock because I can't put five words together. I'm going to do that. So he said, I went out there and two things happened. One, the more I talk, the more my stutter seemed not to be as pronounced. And the second, people started saying, wow, you think you have problems? I have this. So he started connecting in an entirely different way, an authentic way. So our class heard this. And so I said to them, me being the smart ass that I am, I said, okay, folks, so you're a class of winners. Everybody in here is so gifted and talented. But. But, you know, Clark has told us something about himself. And probably a lot of you don't want to be in a class with somebody like Clark. And so I'm going to take a break. You can go to the register and get out of this class. How many of you want to transfer? Obviously no one raised their hand. How many of you feel safer in your own brokenness because of Wood Clark? Everybody raise their hand. I said, if you know nothing else than what you just learned this morning, you will have a rich life. Because every other narrative is, I don't belong in the room because I'm not this enough. I'm not that enough. And that's a fool's errand to do it. I don't belong in any room. I don't. I started this group with John Whitehead, the legendary chairman of Goldman Sachs. We have a small group. He died two years ago, but we. The group continues up the Lynx Club, the Upper east side in New York. And we meet once a month. And everybody in that group, and these are the biggest leaders in America, have said to me privately, you know, I don't think I'm rich enough to be in here. I'm not famous. And I say to them the same thing. I said, I'm the only one that shouldn't be in here. But you guys, every one of them is comparing themselves because that's the world they belong. And so I think that there was a great story about a guy. One of my best friends is Steve Case, who started aol, one of the companies he bought. I will not mention the guy, but. But it's either Forbes or Fortune. Every year would interview this guy about how much money would make you feel secure and good about yourself. First it was 10 million. This went on for 25 years, 10 million. Then it was 50, then it was a hundred, then it was 500 million, then it was a billion, then it was 2 billion, it was 4 billion, it was 7 billion. Then at one point, he was the third wealthiest person in America. And the guy said, surely you feel good about yourself now and that you belong. You're amazing. Look at your net worth. It's incredible. What would you say? And he said, for one day, I'd like to be richer than Bill Gates, but that'll never happen.

John McMahon (23:34)

Wow, you almost feel sorry for him. Right?

John Kaplan (23:37)

You do. Because the average. The data. The data says. I read this and they have. They've got all kinds of data on this. It's like the average human being, it's $70,000 a year, which is unfathomable probably to our audience that, that we're talking to. And they've statistically correlated it. That says after step, because it's. Your basic needs have been met, the exponential, it drastically goes down on your. And I know you don't. You don't call it. You call it meaningful versus happiness. We'll get into that a little bit more. This study was on happiness. Did the money make them many happier? And it stopped at 70 grand, Johnny. 70 grand.

Doug Holliday (24:19)

I mean, I, that, that's amazing, isn't it?

John McMahon (24:21)

I, I, I played golf with a guy that, whose company got taken over.

Doug Holliday (24:26)

Yeah. And you've got to work more. It looks like you just play golf all the time, Doug.

John Kaplan (24:30)

Thank you for saying that. Thank you for saying that.

John McMahon (24:32)

I'm still terrible.

John Kaplan (24:34)

Connect with that.

Doug Holliday (24:35)

And I'm still terrible to tell you that Cap was the one blame it.

John McMahon (24:40)

But Doug, I'm showing my brokenness. I'm still terrible. I'm still terrible.

John Kaplan (24:46)

And that's why he's attracting me to his brokenness, because I'm terrible at golf too. And we golf together all the time.

Doug Holliday (24:53)

Yeah, it's a humbling sport. No.

John McMahon (24:55)

So I, this guy's company had just been taken over and I'm in the cart with them. Make a long story short, in between each hole, he tells me about new condos that he bought, new motorcycles that he bought, new cars that he bought, you know, and on and on and on. And then when I got home, my wife had asked me, you know, how is, you know, he doing? And I said, he sounds so unhappy.

Doug Holliday (25:21)

Yeah.

John McMahon (25:22)

And I just thought because each time he's buying a car and then a house and a motorcycle and another car and a condo, he's doing these, buying these material things that have like a giant rush, but a week later, you still haven't fulfilled the need internally. And he was, he really sounded unhappy.

Doug Holliday (25:42)

No, absolutely. And you know, David Brooks has a great piece that you guys ought to look at if you hadn't seen it. He is a New York Times columnist friend of mine. He contrasts eulogy virtues with resume virtues.

John McMahon (25:58)

I love that.

Doug Holliday (25:58)

And yeah, it's just, it's a great conversation to have around the family table around that about what are we going to really value in our life and our family? But, but, you know, Cap mentioned something I really want to pick up on because I think it's really important, the difference between happiness and meaning. Happiness is correlated with externalities. You know, I have a girlfriend, my son got into good college. I did this, I did that and that. That comes and goes. Sometimes we're happy about these things, sometimes we're not. But meaning is what you want to go for. Meaning you can be in the most God awful situations and still find meaning. And if you doubt me on that, it's a great book written by man. Search for Meaning by Viktor Frankl.

John Kaplan (26:49)

Classic.

Doug Holliday (26:50)

Yeah, classic book.

John McMahon (26:51)

Amazing.

Doug Holliday (26:53)

You know, psychotherapist and he was in the Nazi death camps and he observed the people that survived were not the physically robust, but those who had purpose beyond that. Someday I'm going to play my violin, I'm going to meet my grandchildren. They had a purpose beyond that circumstance and all. So I think for all of us, we gotta figure out what is it? Because this is the other thing I feel really strongly. It's about trouble. Trouble is important to look at because you're either in trouble, you're coming out of trouble, or you're going in trouble. Trouble is everywhere. So it's not to be afraid of. But if you don't understand that, and the problem is with high achieving people, they did everything right. They went to the right schools, they got the right grades, they did the right thing, they went with Goldman Sachs, they did this and that. So everything is like I did it the right way. And then all of a sudden my son took his life, all of a sudden I have cancer, all of a sudden I'm bankrupt, all of a sudden I'm getting sued. I mean this stuff shows up and I said, you have to develop a philosophy of trouble because if you don't have one, it's going to sidetrack you and it's going to blow you out of the water in big time ways. So to spend time, really understand what's your worldview, how do you understand trouble? Because it's all going to happen. I mean it's just a matter of time. Some way someday we're all going to be diminished and you got to figure out, does life still have meaning when I'm in a different state, when I know I'm the strength, the power I used to have.

John Kaplan (28:34)

I really like this topic, John and Doug, because I don't think people really, you know, there's all kinds of phrases out there like embrace the suck or what have you. But there's, there's huge meaning in that because like the data that I've studied and some things that I've personally experienced in my life is they, that there's all kinds of data about post traumatic growth and, but it's just hard to remember when you're in the suck or you're in the trauma or you're in the decline that God's basically designed us with. What, what they call a psychological immune system, which basically means that the next time the suck comes or the next time the trouble comes, we actually have the equivalent of psychological antibodies. So that's where resilience comes from. So I really, really love your philosophy around that. It's. It's powerful, and people just need to hear that, like, wherever you are, wherever you are in your life, when the trouble comes or the crisis comes, it's an oper, and it seems kind of cliche, but it's an opportunity for tremendous growth.

John McMahon (29:37)

Yeah, well, Doug talked about that when we opened the session. He said most of the positions I went into, I was rarely qualified.

Doug Holliday (29:44)

Right. Yeah.

John McMahon (29:45)

I felt the same way in a lot of positions I went into. But then I had. And maybe, Doug, you experienced the same thing. I had this giant fear of failure that really propelled me to do anything I could to be successful. So sometimes, like you were referring to earlier on, our life isn't going to be perfect. And it's okay to go ahead and take a chance in life because if you will jump into that, you will find a way to succeed, and you will, in most cases, have this giant fear of failure, which really does propel you to success.

John Kaplan (30:18)

Yeah, but why do we. But why do we, the older we get, Doug, parlaying onto what John says, why do we take less risk? So that's one of the premises in your book, which is, you know, invite risk into your life. But why, the older we get, are we less likely to do that? Why? What is that?

Doug Holliday (30:37)

Well, to begin with, it's almost like when you're playing a game. Like, you would never go on a basketball court and say, the purpose of playing this game is to not get hurt. Well, you're probably going to get hurt if that's what you're doing. And the problem is, as people get older, you realize their world gets narrower because they're afraid. And when you're afraid, you tend to crawl inside yourself and isolate yourself. So I'm not saying risk will look the same that it did when you were 25, but it should have many, many characteristics where you're, you know, if you've never been to an opera, maybe you say, I'm going to go to an opera.

John Kaplan (31:21)

Yeah.

Doug Holliday (31:21)

If you've never talked to a homeless guy, maybe for the first time you talk to him, what's your story? I mean, yeah, there are little ways you could do this, and it changes your life. You know, I was. I was flying to London recently. I was in Dallas, and I was walking, and there was a woman from Sudan with a hygiene on, just slits for her eyes. And she was really struggling, had a big suitcase, two tiny children. She was struggling with them all. And I was struggling in my mind because I'd been around a lot of my Muslim friends and all, but I also knew she was the most rigorous form of. In the Muslim faith is in Sudan. And I didn't want to put her in an awkward place because I wanted to take her suitcase to her. To her gate because she was struggling. But I thought I'd go as far as she would allow me. And first she was uncomfortable, and I said, can I just take the suitcase? And then she was struggling with the two kids, so I held the hand of the little boy as we went down the elevator. I could tell she felt more and more comfortable. And it wasn't like we were laughing and joking. It was just that she wasn't freaking out. And we got down, and then I, you know, we got on the tram, went to her gate, and I, I took the suitcase over to her gate, and I could see there's a lot of women very, very observant, dressed like her. And I, I, I was very formal, and I said, thank you for allowing me to be a little bit useful, and then walked away. And I thought, you know, did that change my life? No. But did it give me a. Did it force me to think differently for 10 minutes? Yes. And I just think these miracles are every place waiting for us to, to just unwrap them. I mean, they're every place. It's. It just, you know, I had, I told the story in the book. I had this guy. I'd go up to Portland, and I'd see this same homeless guy in front of Rite Aid every time I was up there. And I said, oh, my gosh, I don't want to talk to this guy. And I struggle. And I said, finally, I'm going to ask him his story. So I asked the guy's story, and he said, well, I was a seasonal worker. I'd go around to different parts of the west coast in Mexico, and I would. I would pick fruit. And then I hurt my back. The last thing I want to do is be out here begging, But I can't work. I don't have health insurance. So when, you know, somebody's story, everything changes. Everything changes.

John Kaplan (34:09)

Yeah.

Doug Holliday (34:10)

And that's what's so powerful about probing people's stories. I, you know, I. There's this family I'm really close to, and the son was a great athlete. Heisman trophy winner, actually. And his father and I did not get along. I mean, it was kind of oil and water. I mean, I'm a free spirit. And this guy was definitely rigid in the box. So I was going to a game, and I came in the night before. Next morning, I go to breakfast, and no one's in the hotel but him. And that. That in the breakfast room. I said, oh, my gosh, he doesn't want to sit with me, and I certainly don't want to sit with them. So I'm there. And then I said to him, I said, bill, can I sit with you? He said, yeah. And I said, bill, I've been always curious about your story. So he tells me this, and in five minutes, my whole view of him shifted. He said, well, Doug, I grew up out in the Midwest, and I found out a secret in our family. Not twice 39, but the secret was my father in this small town, had another wife and family. And. Unbelievable. So I asked him, I said, so, Bill, how did this affect you? And here's where it was like a light went off. He said, all I want in my life now is black and white and clarity. Because I knew my whole life something is fricking wrong. Yeah. So I get him now. And I went from resentment of his rigidity to compassion. I get him now. I get him. So once we bother to know somebody's story, life changes. And a lot of us haven't done that with our spouse. We haven't done that with people that we're close to. But it changes us. Everybody is what they're like because of the sum total of all the craziness and goodness that they've experienced in life.

John McMahon (36:11)

Yeah.

Doug Holliday (36:12)

But once you understand that powerful.

John Kaplan (36:15)

There's that saying that, you know, my dad used to tell me, I remember coming home one day and I was telling about this kid that actually, I guess it was kind of borderline bullying, if I'm being truthful. And I was horrified about the story of this kid that I was not very open with. Or my father said to me, said, hey, John. He said, know this. And it's one of the greatest things he ever taught me. He said, everybody has a story. Everybody has a story. And the most successful people in life will be the ones who understand and let people tell their stories. And I've never forgotten that. I was probably less than 10 years old, and me and that kid today are very good friends. Oh, very good friends.

Doug Holliday (37:07)

You know, you talk about. How do you translate that into the workplace? I think one way you can do it is, like, if somebody has a group of 10 people that they're responsible for, you do something as simple as this every week. When you start your staff meeting, say, today we're going to hear from John. He's going to tell us how he grew up, what he thinks affected his life.

John Kaplan (37:34)

Love that.

Doug Holliday (37:36)

All of a sudden, I understand John in a different way. Oh, my gosh. I didn't know you had an autistic son. I didn't know this. I did that. I'm on the board of a big REIT down in Orlando. And I was, I was there and I was sitting next to this woman who's a lawyer, and I said, you know, I've never asked you about your story. And she has two severely disabled kids, too. And it's like massively disabled. And I thought, wow, I now have a different view of how she has to survive every day and this problem isn't going away. And. But once you know, that, boy, do I have a different. It's like Marcel Prowse said, the key is not just to see, but to see with new eyes. Knowing the story enables you to see with a fresh set of eyes things that have been, you know, standing and right in front of you.

John McMahon (38:34)

Yeah, and right on that. Doug, earlier seen with a fresh set of eyes. Earlier, you touched on the pandemic. And you know, this isn't just business people. Now, the pandemic really forced a lot of people to look within themselves and in many cases reevaluate where they were in their lives. So people moved, they changed jobs, they changed careers, discovered new sports, new hobbies, and reevaluated what was meaningful in their life. So in some ways it was a double edged sword. But why did it take a pandemic to force so many people to discover what's meaning? What do you think?

Doug Holliday (39:14)

It's kind of like, yeah, this one Oxford scholar by the name of C.S. lewis. You know, many of us don't know what a megaphone anymore is, but in the 30s and 40s, this is how they would. Before they had amplification, they would yell into this cone like thing and amplify their voice. CS Lewis, who's a Oxford scholar, he said this pain is God's megaphone. You know, pain, you, you hear it like, when I'm in pain, I got plenty of time to pray. When I'm in pain, I have plenty of time to think about my life. And, and so pain is a good thing because it makes you, forces you to recalibrate what's really important and it cuts through all the bs and then you have to say, wow, who, who really am I? Because we can get carried away with ourselves. I remember a guy I invested with in New York said to me one time, I remember feeling like, wow, be careful. He said, I'm financially bulletproof. I said, wow.

John Kaplan (40:21)

Before 2008 or after?

John McMahon (40:23)

Yeah. Or how about the current market? Yeah.

Doug Holliday (40:27)

Yeah. I mean, it's just. It's. It's amazing when you think of it. And, you know, there's nothing secure. And that's the thing people keep thinking. I mean, I live in these places. I'm in McLean, Virginia. I mean, somebody's building the house. It must be. We just were at dinner party. This Guy's house was 47,000 square feet. They have no children. It's a couple and Potomac. And I'm thinking, wow, what do you do with that? Where is the soulish connection? Where do you. Where do you find people and where.

John McMahon (41:02)

Do you find your spouse?

John Kaplan (41:05)

That's why it's 47 pounds. Yeah.

John McMahon (41:10)

Hey, Doug, if we switch gears real quick, can you switch gears? So you went from the business world to the White House world, diplomacy, back into private equity, and you saw so many different leaders. Were there some common traits that you noticed about the different or the greatest leaders that you met? Or were there certain traits that you saw from certain leaders that you thought, ah, I need to do. I need to incorporate that in my life? Is there anything along those lines from your. From your.

Doug Holliday (41:45)

Yes. I think the best leaders have a humility. Number one. You know, the gray and the Greeks nailed it. They said, hubris is the greatest sin when you think you're God's gift to the world. Watch it. But I think real leaders have a humility, and they're really grounded. I think on the other side there, so many of them are shocked that they've been as successful as they are. They do say I'm not smart enough or good enough, but somehow here I am, CEO of a Fortune 100 company. I don't know how this happened. So they feel like luck and fortune really were good to them. I think they also the best really take time to connect with friends, a couple friends in their life. And, you know, I have a friend, some of you might have heard of me, Ray Chambers. And Ray invented the leverage buyout. Started West Ray capital in the 70s and 80s. I mean, he's a rock star on many levels, but. But Ray is a good friend and. But Ray is really interesting. He decided he had enough at about 44. I mean, he was a billionaire, but that enough. So I remember he came up to Goldman Sachs and we were on the 22nd floor. So there was this partner there. And I said, mark, come Here a second, said, do you know Ray Chambers? And he said, oh, of course I know who he is. And I said, Mark, why don't you do something interesting with your life? We're trying to develop this mentoring points of light thing and you know, you could be great to help us. And he said, well, if I had as much money as Mr. Chambers, I would do to that. And then Ray looked at him and said, Mark, how much is enough? And you could see his brain gotta calculate. And then he said, how did you know it was enough? He said when I realized the price of making more was doing bad things to my soul, I decided it was time to leave and pivot and do other things. You know, I'd recommend. If you haven't ever read this, there's a letter that Andrew Carnegie wrote himself in 1888 at the St Nicholas Hotel in New York. It's a amazing letter. He was, he was 33 years old and he said, you know, I have passive income, this is 1888, I have passive income of 50,000 a year. And he said I'm going to work three more years. While I'm working, I'm going to have really intelligent people speak into my life, teach me things I never learned growing up. And then he said, he said money is the, can just be so corrosive and make you into something that's an ugly creature. And then he said, after three more years I'm going to get out of this. I'm going to move to Oxford and put myself under the care of some of the smartest people in the world and then I'm going to buy a controlling interest in a newspaper or something. Sounds like some of these guys today. So the question inevitably becomes here's a very self aware guy at 33, Andrew Carnegie, but did he do it? And the answer is no. He started making so much money that he couldn't give it away fast enough. So he set up the Carnegie foundation, one of the first public charities, I think it was the first and. But you know, but he always resented it when he went back to Edinburgh where he was uneducated, was part of the American dream, came over, he took, he took his mother over and they had gold carriage made and went down the main drag of Dublin. And just in his way of saying see, see what this note less privileged person could do with his life, you know. Yeah, but it's interesting even though he had all this stuff and did it make him define meaning? I don't know the answer but he was, he was moving around the right. Questions at 33.

John McMahon (46:07)

Yeah. You know, Doug on, you founded Past north, you know, again, that's a nonprofit that you started, dedicated to helping business owners and CEOs redefine success. What was the trigger in your career? What did you see in your life or other your friends lives that said, this is something that I feel I gotta do? What was it?

Doug Holliday (46:32)

Yeah, it's interesting because my whole life I've had the privilege of being trusted by people that I work with, whether it's Jim Baker at the White House or Bob Rubin at Goldman or whatever it was that to be in these amazing, privileged relationships. And so after the financial crisis of 2008, I kind of felt there's so many of my friends that are really feeling lost and they want to move someplace. They're trying to. Tired of being vilified as a capitalist. The kids are getting yelled at, all kind of craziness. I said, we've got to create a community of people where we can have these really important conversations that nobody's having. What. What is the meaning of life? How much is enough? How do you raise children of privilege? All this kind of thing. So I ran it by some friends. Steve Case, the heising is down in Florida, Ben Dupont, John Tyson, bunch of people. And we started. And we started having experiences. We'd have salons. We've had 35 of them in different cities where I'll bring somebody interesting in and interview them. But we'll get people talking on a level that they've never talked a lot of time. We have trips international and domestic, but it's all toward really people getting an idea or connecting with somebody or recalibrating a life because of some experience. So we don't just take trips, we take trips that'll change you. You know. Our first international trip was on the Orient Express. A lot of people can do that, but we did it differently. We called it the Magical Mystery Tour. We took magicians with us and they were amazing. And along the way we pick up European magicians and all this. But what was interesting? Every night around the table, we talked about Tuesday, two questions in the magic motif. What are the illusions you had about life, in other words? I thought my son would do what I was going to do, whatever it is. What are the illusions you had and what are the mysteries you're trying. Still trying to figure out? And I want to tell you, they went deep. It was crazy.

John Kaplan (48:53)

It's amazing because it probably for you, it wasn't about destinations. No, it was about experiences.

Doug Holliday (49:01)

Exactly.

John Kaplan (49:02)

And that's a big part of what you write about. It's. It is not the, it's kind of not the end, it's the, it's the being.

Doug Holliday (49:11)

Yeah, yeah. That, that great poem Ithaca is really powerful because it talks about, you know, we all have this metaphorical destination in mind that's Ithaca, which is a financial number or accomplishments or whatever. And it's an illusion. And the poem Ithaca says, you know, the process of being on the journey. So that when you get there finally to Ithaca, you're old but wise in the experiences you brought to Ithaca. But Ithaca won't make you. You've already been made.

John McMahon (49:50)

That's powerful, really.

John Kaplan (49:53)

So, Johnny, we're talking about, we are talking to Doug Holiday. We are talking about some tremendous life experiences that he's had that have kind of culminated in this awesome book. Anybody listening? It's a must read. It doesn't matter how old you are. I personally think the younger the better. If I could learn, if I could talk to my 25 year old self. Joni, do you remember just a couple of weeks ago I told you that I missed that 18 year old with the duffel bag myself on a one way ticket to Boise, Idaho? Johnny and I just had this conversation two weeks ago, but there's this, this book has culminated. It's called Rethinking 8 Essential Practices for Finding Meaning in Work and Life. Johnny, I was going to do a, a recap here, but you tell me whether you're ready to pivot. Okay, yeah, let's just do a quick recap here. We started off with kind of a conversation around. Your basic premise was fortune favors the bold. And it's one of. Actually it's kind of related to one of your tenants about, you know, making sure that you always have the ability to continue to look at risk in your life. I'm not saying how much or how little, but if you don't have any in your life, it's not a. It's not a very meaningful life. I love what you said. You, you were very clear in the beginning when you said, I know what I'm good at and you're comfortable with what you're good at. And I think that's incredibly good advice. I think people that are good at things and it gives them energy. Those are the people that I have found that are the most successful people in this world is they wake up in the morning and think they're doing exactly what they're supposed to be doing. You talked about an exercise that you do with your MBA students Life in five year blocks. What did you love doing and what did people say that you were good at? So what did you love doing and what did people say that you were good at? And then analyzing the huge percentage of people that don't do it anymore and I'm really kind of sitting with that and but all of you said that these things that we're good at, they, or that we were passionate about, they get eclipsed by the money chase which I thought was very, very powerful. And then we got into a great conversation. You called it the blessing. And most people are, don't, aren't fortunate to get that blessing from people that validate us in our lives. I luckily I was, I did get that from my parents and I feel very, very fortunate and grateful. But even if you didn't get it, you encouraged us to basically create your own blessing by understanding the meaning of your own story. Our point of identity is not our strength, it's our brokenness. Our point of identity is not our strength, it's our brokenness. And connecting through our challenges is more powerful and authentic than our strengths. Is what you've learned through your experiences and what the data tells us. You hit us home with a deep one where you said eulogy virtues versus resume virtues that was very, very powerful. Happiness versus meaning. We talked about, loved how you talked about trouble in trouble or crisis is related to meaning and purpose. So you know, don't fret. There's wonderful experiences with post traumatic growth is what the data tells us. So it's an opportunity to grow and not being cliche like hang in there, you know, you can get through the suck there. The data says that there's an opportunity for tremendous growth out of the suck. Yeah, everybody has a story. Invest in letting the other person tell their story. Not, not just to see but to see with new eyes. So don't listen to that story just to hear it, but to hear it with new eyes. Johnny asked you about leadership traits. You talked about humility and authenticity and how most great leaders have this, you know, imposter feeling or they feel unworthy or you summed it up really well that said they feel lucky, they feel grateful and they're also great relationship builders. And the one of the most powerful things I heard you say, which I'm going to write a lot of these down. I did write them down. I'm going to keep them on pieces of paper. How much is enough? How many topic of conversations I have at least once a week where I either ask somebody or somebody asked me how Much is enough. And you gave the quote that said, when the price of making more begins to do bad things to my soul. Dude, that was deep. That was deep. That was deep. I'm keeping that one written down. What I miss Johnny Mac, just at.

John McMahon (54:58)

The end, you know, when he talked about being on the Magical Mystery Tour, those two questions, you know, what illusions did you have of the past? And what mysteries have you still not figured out? And you want to figure out? Those are. Those two questions will make you think also.

Doug Holliday (55:16)

They'll make you think. One thing I didn't say that I'd love to just. If I can mention it real quick, is on forgiveness, I think most of us not forgiving somebody that's harmed you, it's like me taking poison and expecting you to die. It's stupid and it doesn't work. And so we need to really do our business with that thing and say, where has there been somebody that's harmed us? I mean, we all say, oh, if. If John came up to me and said, doug, I just want to ask you forgiveness, I know I talked behind your back and that was terrible. Would you forget? Of course I'd forgive. That's never going to happen. So what you have to do is say, how do I live when I know I've been harmed? Somebody did it purposefully. How do I live? And I'd say, you're. You're not doing this for their sake. You're doing it for your sake. Forgive. Let it go.

John Kaplan (56:13)

Confucius, I think you. I heard you say, Johnny, Confucius says, seek revenge, and you should dig two graves, one for yourself. That's really powerful.

Doug Holliday (56:26)

It's. It's. Yes. Yeah, it really is.

John McMahon (56:29)

Well, in your book, you stress the importance of two. Actually, two things. Forgiving and serving versus resentment and accumulation.

John Kaplan (56:39)

Yeah.

John McMahon (56:40)

Yeah, I picked that up from your book. It was really. That was. That really struck me.

John Kaplan (56:45)

So while we're giving the list, Johnny, there's only one more we haven't talked about, which was Doug. It was gratitude. So I know it's a big part of your mantra, and can you just kind of bring us home on the topic of gratitude and why it's so important?

Doug Holliday (56:59)

I want to show. I want to show you something real quick. You know, it's funny how neuroscience has now validated how gratitude literally changes our brain.

John Kaplan (57:10)

Yes.

Doug Holliday (57:10)

So I've been doing this for some time now. I don't know if you read this. This is a piece of graph paper.

John Kaplan (57:17)

Yes.

Doug Holliday (57:19)

So every day I shoot for maybe four days, a week I'll write down three or four little things that I'm grateful for. They could be little things, they might be dark roast, cup of coffee, the sun shining. You know, I got a call from my son to tell me about his Costa Rica thing. Write these down. It'll end up at the end of the year. It'll be both sides, probably about 2,000 little bursts of gratitude. I then laminate it. I know this is really weird, but it reminds me of gratitude. And so I say to people, you don't have to write down what wakes you up at 3am and sucks in your life. You got that? That is always good. But you have to create space through that jungle to focus on. What are those good things that are happening to you? What are those blessings that are every place? And that changes your whole outlook if you do that.

John Kaplan (58:17)

DOUG the neuroscience. I'm a big fan of the neuroscience behind this, and this is what I learned last year when studying it, is that they now have the ability to put electrodes on your brain and they have found that by introducing gratitude. And this is amazing how God designed us this way. It is the only emotion that the human brain cannot share space with any other emotion. So the minute you introduce gratitude, depression, anxiety, anger, they disappear because it cannot share the same space. However, depression, anxiety, anger in your brain, dude, it's, it is, it's amazing. It's amazing.

Doug Holliday (59:00)

That is really great. And it is such a wonderful, you know. So if I were to say to people, how do you get started? Because a lot of us don't know how to start. I would say one, create space in your life every day. Like it might just be five minutes or seven minutes, but pause. I have classical music going on here. Sometime I'll have Gregorian chant. Just reset. If you don't reset, you're going to keep doing the same old, same old same. So you reset, you breathe, and then you write down these things you're grateful for. Then you might have something that's high minded. I read this fascinating monk named Richard Rohr, who's a Franciscan monk. He's so insightful. I'll read just a half page thing he does every day. And then I'll write down, you know, things that people I'm concerned about, things that I'm, you know, that are on my mind. And that's how I reset every day.

John Kaplan (59:56)

Will you come and visit me and my family at Thanksgiving? I want you to just sit around a campfire and tell all the stories you got. Dude, I want, I want that experience you're Amazing.

Doug Holliday (60:09)

No, I'm. I. I'm just. You know, it's just weird. You know, somebody asked me one time, when was the first time you remember a leader trusting you? Do you want to hear this story? Because it's kind of weird.

John Kaplan (60:21)

Yes.

Doug Holliday (60:22)

So I was. I was at Chapel hill. I was 18. So I'm. I'm. I had this youth group in Durham, and I.

John Kaplan (60:30)

It.

Doug Holliday (60:31)

It was very successful. Hundreds of kids would come to this. So I got a call one day from this woman in Raleigh, North Carolina, and she told me who she was, and she says, you know, my husband's the congressman from this area. And she said, my niece got involved with your program, and I don't know what you did, but her life is changed. She's on a dirt. She's got a path. She knows what she's doing. And I said, well, despite. Despite me, she found, you know, a path. Then this woman says to me, there's a very powerful guy in Raleigh. He's the wealthiest guy in the state, and he is really, really struggling. Would you spend some time with. So this guy's about.

John Kaplan (61:13)

And you're 18.

Doug Holliday (61:15)

I'm 18. So this guy would drive over to Chapel Hill every day. I mean, every Thursday. And we'd sit there and this. His long Mercedes, you know, with the sticker on the right has the sign of the Mercedes written out. And I. I'm. I'm like, everything I'm telling this guy, every cliche I've ever read, anything, and I'm. After two months of this, I said to him, greg, I. I'm sorry. I don't have anything else. I don't have a lot of life experience. I've told you everything I've thought and learned. For some reason, at that point, I stuck out my hand and I said, greg, would you shake hands with me? He'd been talking about taking his life. Said, would you shake hands and vow to me you will not take your life unless you call me first? And he hesitated. He agreed to that. So I'm 18. I lost touch with this gentleman, didn't know what happened to him. So I'm out in Vail, Colorado, skiing. I was about 42. It was really cold. Nobody else went to skiing. I said, well, I'm just going to go up one time. So I go outside, get on the chairlift. We're all bundled up. I'm sitting next to this guy, and I guess my voice is little bit distinctive. And he said, doug, is that you? This is Greg. Go bump, dude.

John Kaplan (62:39)

Goosebumps.

Doug Holliday (62:41)

Yeah. He says, this is Greg. I'm still alive.

John McMahon (62:44)

Wow.

Doug Holliday (62:46)

And we got off the thing and he said, you know, every time I was ready to end it, I thought of that. I've gotten help. I realized I had clinical depression and a very different space in my life. And I thought, so this was, there might have been a couple more earlier, but this was a big one. And I realized that I didn't have a lot to bring to anything except comfortable, vulnerable places with people's hard stuff. And that's why I've been really grateful to be a part of that.

John McMahon (63:22)

Awesome, awesome doc. How about, how about five quick questions? You ready?

John Kaplan (63:28)

Rapid fire questions, Doug.

Doug Holliday (63:30)

Oh, I was going to ask you five.

John Kaplan (63:34)

No, we don't want to answer any questions after what we just heard, buddy. We got a brush step on our.

John McMahon (63:39)

Answers about your ideal day off of work, Doug.

Doug Holliday (63:43)

Well, I think work should be an expression of who we are, so it should energize us. So I kind of feel a lot of time, I'm always playing and always working, so it's not a big stress to me. But, you know, maybe bike, biking, maybe. I, I'm a collector. I love art. I love doing all kind of things like that, kayaking, things like that. But I, I'm not a big guy. Like, okay, I'm going to go down to the Bahamas and do this. I, I kind of, I'm pretty content wherever I am, you know.

John McMahon (64:20)

Awesome. How about your favorite meal?

Doug Holliday (64:23)

Favorite meal? I still am crazy about Italian. You know, I, I, I, I love Italian and I love these family owned Italian. But I love the, I, you know, I love old classic movies, particularly 1938-42. And I love In New York. I've got an apartment there and there's a Great one on 30, 38th and park called Rossini and I love it. I feel like the mafia could come out any minute and it's awesome. I love that. I love, I love Chianti and Amaroni wine. I love, I love all kind of ones. But yeah, so I think, I think Italia would be a big one for me.

John McMahon (65:02)

Yeah. And what about you? You have a favorite movie of all time.

Doug Holliday (65:08)

I think the Letter with Bette Davis is one of them. That's about 1939. Awesome. Because I like the black and white, the way they use shadows.

John Kaplan (65:18)

Yeah.

Doug Holliday (65:18)

How they use the music juxtaposed to the black and white shadow. So that's, that's a powerful, really powerful movie. Yeah. My favorite, my favorite musical though is My Society with Bing Crosby, Louis Armstrong, Frank Sinatra and Somebody else. Anyway, that was like 1954. It's amazing. It was a remake of the Philadelphia Story, which is made with Katharine Hepburn and Spencer Stewart, but it's a great story.

John McMahon (65:54)

How about you have a favorite concert you ever been to?

Doug Holliday (65:59)

You know, my boys are musicians, and so, you know, we had the best time. We went to Coachella a couple years ago. I love Neil Young. Love Radiohead.

John Kaplan (66:11)

Wow.

Doug Holliday (66:13)

Pink Floyd is killer. Oh, my God. So, you know, it was Mick Jagger. They were all there. Paul McCartney. It was.

John McMahon (66:21)

That was the desert trip. That was the desert trip. I went there with my daughter.

Doug Holliday (66:26)

Oh, did it. Oh, my gosh. The who?

John McMahon (66:28)

Paul McCartney, Neil Young.

Doug Holliday (66:30)

Oh, it was on. I don't think they're doing anything.

John McMahon (66:32)

Rolling Stones.

Doug Holliday (66:33)

No, it was so. And we were in the mosh pit, which. Other than standing for about 12 hours.

John McMahon (66:41)

All right, one more. Doug, do you have a favorite charity or.

Doug Holliday (66:45)

I was on the Morehouse Board. I was on the Morehouse College Board, which is African males in Atlanta. Martin Luther King went there for. I was that for 14 years. I was blown away how it changed my life to be a minority. And again, putting my. I always try to put myself in positions where I'm a minority so I can learn, whether that's with Muslims or any. Any group that.

John McMahon (67:10)

Where.

Doug Holliday (67:11)

I just need to figure out what this will do to me. It was great being on the board, being one of the few white dudes there, and that was great. So I. I think what they're doing with young men is extraordinary. It's. It's incredible.

John Kaplan (67:26)

Do they have a foundation like Morehouse College? Is there a foundation?

Doug Holliday (67:30)

Yeah, they. They have a. I mean, by comparison to a lot of the Eastern schools, it's not huge, but they do have. They do have meaning.

John Kaplan (67:38)

Can you donate into. Can our. Can our listeners contribute to it? Is there. We'll put it in the show notes.

Doug Holliday (67:44)

Yeah, yeah. They have an endowment, no question. It's really, really good. Per.

John McMahon (67:50)

Well, Doug, we are honored, and I'm really grateful to have had you on the podcast, and I know our audience is going to really take a lot out of this, so I want to thank you personally for being on. And I'm very.

Doug Holliday (68:04)

Thank you, John. I. I love what you guys are doing. I mean, you're doing something really important, a probing this side of life, because either people aren't comfortable with it or don't know how to do it, and you guys are both. Now, make sure you tell Cedric. Everything I learned came from him.

John Kaplan (68:22)

Amen.

Doug Holliday (68:23)

Particularly when we had the second bottle of wine in Italy.

John Kaplan (68:27)

So that's. That's a. That's a tip of the hat to our friends at MongoDB and Cedric, who actually turned us on to not only you, but your book. And again, the book is called Rethinking Success. Eight Essential Practices for Finding Meaning and Work in Life. We're honored to have spoken with you. Doug Holiday, you are amazing. Thank you for taking the time. You didn't know us. And you didn't even know there was a connection to our friends at MongoDB.

Doug Holliday (69:00)

No, it's great. Another time I'll tell you about Dev. What? I asked Dev to read you the poem I made him write.

John McMahon (69:07)

Okay.

John Kaplan (69:09)

Awesome. Doug, we're so grateful that you were with us.

Doug Holliday (69:12)

Thank you, guys.

John Kaplan (69:13)

Thank you for being here.

Doug Holliday (69:13)

I'd love to get with you guys at some point. So let's figure out how to do that sometime.

John Kaplan (69:17)

Well, you come to Thanksgiving, and then Johnny's coming, too. I want more stories.

Doug Holliday (69:22)

I can only stay a month. I wish I could stay longer.

John Kaplan (69:25)

And thank you, all of you that are listening and continue to listen to revenue builders.

Podcast Host (69:32)

Thanks for listening to today's episode. Be sure to check us out@ForceManagement.com.