Why Risk Takers Build the Most with Doug Holladay, Author of Rethinking Success

0:00John McMahon: The most accomplished who have actually done so much better than their parents and they're sitting on some, however you measure success, some kind of success. What they want to do is protect their children from the very things that made them amazing. Everything in modern society now is creating guardrails so our kids can't figure out life. So we are protecting them from the very pain, setback, hurt that could make them a LeBron James or could make them a Howard Schultz. Welcome to the Revenue Builders podcast, a weekly show featuring B2B sales leaders and executives. hosted by five-time CRO John McMahon and force management co-founder John Kaplan.

0:53John McMahon: The show takes guests in the barrel behind the scenes with the people who've been there, done that, and seen the results. Revenue Builders covers best practices for scaling and growing your business while sharing the pitfalls to avoid.

1:08John Kaplan: Today's guest is Doug Holliday, who's back with us for the next installment in our series on his book, Rethinking Success. In our last conversation, we explored humility and the art of letting go. This time, we're looking at two practices that build directly on each other, defining success and failure for yourself and inviting risk into your life. If you're just joining the series, Doug has had one of the most varied careers out there, public service, international finance, private equity, and now he's the founder of an organization called Path North, where he helps CEOs and business owners broaden their definition of success.

1:50John Kaplan: In this conversation, we ask the question most sales leaders never stop to ask. Whose scorecard are you actually playing by, and why do the sales leaders who take real risk, not reckless ones, but real ones, end up building the most. These conversations with Doug are so good. Let's take a listen. So Doug, it's so great to have you back. Today, we're going to continue with thoughts on the incredible book that you provided, you know, the world in rethinking success. And we're going to Talk about chapter six and seven today, which is around defining success and then failure for yourself and also the concept of how risk plays a significant role in that.

2:51John Kaplan: You're such an amazingly talented individual with an incredible story. you know i don't know if i've ever asked you this but like when you were growing up i know what you've done when you were growing up how was uh success defined for you when you were growing up and and how did that manifest itself into what happened for you well it's

3:14John McMahon: interesting my sister and i if you met her we're almost bookends i mean she's been in fashion with Vogue and raised her family in San Francisco. But she's definitely out of the box, like me. And I think we've talked about it. We had a father who was a finance guy. He was a trained accountant, all that, really in the box. But he had a creative streak. But my mother was kind of this magical, you know, visionary dreamer, just believed that anything is possible. Every breath I took was the greatest breath anyone's ever taken in their life. So, I mean, it was like having my father was very much achievement-oriented in a traditional way.

4:04John McMahon: My mother is very much unconditional. You are the greatest, smartest, best, everything. So you had this funny kind of combination where both my sister and I were high achievers, But we also love people and we we understand the most important thing of life is connecting and knowing people and and and going there. And we both always took crazy risks. Like recently, she told me that her husband freaks out over this. She went to go to the Madonna concert in San Francisco. This is typical of my sister. So she said, there's no way I'm paying two thousand dollars for a ticket. So she says to her husband, let's go down there in San Francisco, and I'm going to have a little sign that says I'm willing to pay$450 for a ticket.

4:57John McMahon: Her husband says, there's no way I'm doing that. So she goes down by herself with a ticket or with a sign. And a woman comes out and says, hey, my daughter's sick, and I've got this ticket. So she sells her the ticket. They go there. my sister then was going to Italy for a month to do all her fashion stuff and she takes women to all those couture places and all that so the women now is one of my sister's best friends but that's fairly typical of how she rolls it's almost like instead of saying you know why shouldn't we do this it's always why not well yeah if you want to do it let's Let's just do it.

5:41John McMahon: Just show up. And it typically works. And so so that was the that was the world I grew up, grew up in. He was much harder on my older sister than me. She was kind of a math nerd, even though she was beautiful and homecoming queen in those days in college and all that. but they would work on math equations late into the night. He kept saying to her, you know, good looks are only going to take you so far. You've got to really do the work and all that. He kind of thought I was a ne 'er-do-well because I didn't have to work that hard. I could get pretty good grades. And he just felt like everything kind of broke my way.

6:32John McMahon: and uh it it frankly sometimes it bothered him he says you know it's you you somehow it always turns out so yeah so you when when we dig into this chapter there's a theme of many of us are

6:53John Kaplan: playing to a scoreboard we didn't choose yeah yeah and um that's deep and when i think about our audience, there's a couple of themes in this section I'd like to talk about. First of all, that scoreboard you didn't choose, like when do you realize it? And my hypothesis is the earlier you realize it, the better life you'll have. And so many of the leaders that I spend time with, I asked them a simple question about what's your exit strategy. And it's a simple question. If it's an entrepreneur, if it's a business owner, it's a, you know, you'd expect them to have an exit strategy. And I'm amazed at how many people don't have an answer.

7:46John Kaplan: So they're in a race. And none of us are really built that way. If we said to ourselves, no, I'm competitive. I know what the start line is. I know what the finish line is. I know what the metrics are. But when you ask them that question as it relates to kind of like your life, why is that, Doug? Why do we seem to be running at a scoreboard we didn't choose?

8:10John McMahon: Yeah, I mean, I think you raise a great point. And I've seen that up close and personal with so many of the leaders that I've interacted with, that they have been successful. I contrast the difference between the how and the why. The how is all these things that are metric oriented. And they're easy for men to understand. Okay, you work hard, you make the team. You work harder, you do better on the team. You know, it just seems like it works that way most of the time. But the problem is when the how keeps succeeding and then we all get to a point where that how stops and you've got to then ask the awkward question of why.

9:00John McMahon: What's my why? And we have never been trained in the why. We now we used to be when you look at, for example, in liberal arts colleges up until probably the early 50s, liberal arts college, the most important thing that went on was the last day for seniors where the president of the college would would deliver something they called the last lecture. In the last lecture, the president of the school felt like it was his job to say, okay, we've equipped you with the technical things to succeed in the way the world is going to serve life up for you. But that's not the most important thing. It's the kind of person you become.

9:46John McMahon: It's your why. It's your purpose in life and all that. They used to do that because they saw the integration. This is why most of us that grew up in a certain era, when you went to college, I went to Chapel Hill. The first two years of college were all about broadening your view of life. So you had a larger aperture. So in other words, you take languages, you take philosophy, you take English literature, you take history. Now I teach at Georgetown. What do you do? You apply to the business school. You apply to the School of Foreign Service. So day one at 18, you're supposed to know what you're supposed to do with your life.

10:32John McMahon: And you're taking business courses. The messiness of having, the only school I know that still does what Chapel Hill did when I was there is Columbia University. The first two years, you still have to take what they call the core curriculum. Because they feel like to be a good leader in anything, you've got to be grounded in certain traditional ways of thinking about your why. so so so it's not surprising that people are are confused because eventually we get to that point and i have this new yorker cartoon with this guy on his deathbed with all these wires hooked up to him and tubes and he's looking over at the nurse and he says i should have bought more crap you Of course no one's going to say that.

11:27John McMahon: But no one prepares you for how should I think about this last chapter? What does that look like? There's a great book I read in the 90s called Die Broke, and it was really interesting. It was a financial planner in New York City who always puzzled. I'm dealing with the most wealthiest people in the world, and none of them feel like they have enough. And the reason was they never calculated they were going to die. So he would go to see them. So a guy 75 says, OK, when do you think you're going to die? I don't know. 85, 95. Let's do it crazy. Let's say 95. OK, 95. Great. Now let's work backwards.

12:17John McMahon: There's no way you can spend all this money. so why don't you figure out how to die broke in other words bless the people that have blessed you that that tutor that you had that sixth grade teacher that that your kids instead of leaving themselves create memories go on great vacations with them you know empower them now while you can work with them. So it was a very interesting thing because he felt like the reason they never really dealt with this, because most people were in fantasy land that they're never going to die. And they just kept thinking and thinking. And it was like, so once they had the courage to put a number on that, then you said, okay, you've got 15 more years.

13:12John McMahon: What do you want to do with those 15? So they are unbelievable.

13:17John Kaplan: Well, you're hitting a real chord for me. I just read a book by Jimmy Johnson. I wasn't expecting to, I don't know how, it popped up on my Kindle. Jimmy Johnson, the coach. Yeah, for Dallas. Dallas and Miami. And I wasn't really a big fan of his. And like, I was watching him. I found his book so profound because this lesson that you just shared with us, he calls it QT, QTL quality time left. Yeah. If you remember, he abruptly left. Yeah. Yeah. He abruptly left the Dallas Cowboys. And then he did what I think he came back and he coached the Miami Dolphins, I think. and Wayne Heisinger had a huge impact on him.

14:08John Kaplan: It's actually his boss that introduced him to QTL and he could tell that Jimmy Johnson had no plan. And it was really around the concept of death. Wow. Like the concept of death, he never went to a funeral his entire life. The first funeral he went to was his mother's and he was wrecked by it. And he was probably in his 60s or 50s and he was wrecked by the, and I just, you know, so Q2, QTL, I actually have it written down on my desk now. It's profound for me because I'm 63 years old. And although I feel blessed because of some circumstances in my life, I don't really fear death anymore. Used to badly, but I don't fear death anymore.

14:54John Kaplan: But the concept of quality time left.

14:58John McMahon: Oh yeah.

14:59John Kaplan: Would I really be doing this Johnny and I talk about in this podcast One of the reasons why we continue to do this Because we like spending time together We love spending time with you We're going to spend time So quality time left is Something of a real It's really important

15:16John McMahon: I take it another step I'm shocked at how many people Have not with their children Had these kind of conversations So I just came back from Three days with my two oldest boys We do this every year where we just go through everything. It's an inventory. I want them to know, I don't want any surprises. I've done things like, okay, let's drill down on everything from a medical directive. I don't want a team doing this, guys. My older son's making the decision. You can give your points of view. But the last thing we need is to have a debate about, well, there's going to be a new medical advance. So don't pull the plug on that.

15:57John McMahon: I said, you guys need to, I've had a great life. We don't need to do anything crazy. So we have these kind of conversations about everything. And it's not like a depressing conversation. It's kind of liberating. I want them to know how I think, what I care about.

16:16John Kaplan: As long as it's healthy. So you're talking to a guy that used to carry eight names in his wallet. So if he died, my wife didn't have to search for friends. Oh, God. who was going to carry me as a pallbearer. And that was just, you know, that was my own anxiety of, if I don't have eight friends, you've got to search around for eight friends at the end of my life. That's a true story. Yeah.

16:41John McMahon: That's a true story. That doesn't help me. The tragedy is they have this thing now where people have to actually hire pallbearers because they don't have any friends. See? I was ahead of my time. It's unbelievable. It's it's these things are just so crazy. And but I think there's a fear of it. It's almost like, you know, the death things are part of it. It's almost like the things have brought you meaning. So you think about particularly for men that worked, the closest thing they had, the relationships, authentic relationships was in the workplace. So all of a sudden that goes away. They don't know how to do it.

17:27John McMahon: So I tell my class this fictitious story. I said, OK, so so Bob's wife died two months ago. So, you know, they've been married a long time. So I say to my wife, hey, I'm going to go play golf with Bob today. Oh, that's fantastic. I'm so glad you're going to spend that time with Bob. So I go play golf with Bob, and it's a beautiful day. So I come back my wife. So how did it go? Oh, great. Beautiful day. Oh, my gosh. We had the best time at the club and saw some old friends. How's Bob doing? What do you mean, how's Bob doing? This is your best friend. His freaking wife died two months ago. Oh, it never came up.

18:11John McMahon: Now, every man knows exactly what I'm saying. And every woman would be aghast. Yes. The idea of a woman spending four hours with their best friend and never discussing the fact that their spouse died is like unconscionable to them. But for men, that's dangerous territory. I might have said to Bob, you okay? Yeah, I'm good. You good? Great. That's about as far as we get.

18:42Doug Holladay: I want to talk to Cap about some of those things, but when he's always in the woods searching for his golf, it's hard to have those conversations.

18:50John Kaplan: So, Doug, you pick people to play golf with that are going to build you up. Not me. I'm so terrible.

18:58John McMahon: Okay.

18:58John Kaplan: No, but they're going to support you, and John's just hurtful. So I don't know where that comes in in your chapters. Well, we'll put him on the spot and say, what is it about you that, Max, you've got to win?

19:13Doug Holladay: No, let's switch gears a little bit. In your book, you do talk about this landmark study that was at Boston College by a researcher. I think her name was Karen Arnold. And she wrote a book, Lives of Promise, where she tracked 81 high school valedictorians for 14 years after their graduation to see how their academic success translated to success later in life. Right? Yeah. Very well put. They were very competent. They worked hard. But none of the valedictorians grew to become very successful in their field. And you might ask why. And what the book said is that valedictorians typically succeed by playing it safe, you know, conforming to expectations and prioritizing, you know, high grades and test scores over, you know, any like passionate success in any one area.

20:12Doug Holladay: Right. So they kind of. They generalists and they basically are trying to please every teacher across all these different subjects. But in the real world, success often rewards deep specialization and risk taking versus broad compliance and pleasing everybody.

20:34John McMahon: Now, you've articulated it so, so beautifully, Mac. That's exactly the thing. It's the very thing our parents, everyone celebrates in school, but it's the very thing that doesn't equate to success in life. You know, I remember talking to a guy who's a billionaire I went to school with. And he said, well, all you guys got great grades. And I was just screwing around and was a C - student. And I eked out of Chapel Hill. But, you know, I was a risk taker. I built companies and did all this crazy stuff. But so, you know, we don't reward that. And I think it's a tragedy because you look at kids like you take kids, high risk neighborhoods and all some of these kids that have developed drug empires, for example.

21:26John McMahon: Do you think that's the same gene that's this an entrepreneurial gene, but they haven't had an outlet for that? So you kind of feel like if our schools did more of that, celebrating entrepreneurship, risk taking, you know, trying things. And there were little things when I was in school that I would try. You know, you had theater, you could try to play a musical instrument and there were people there that would teach you. And you just tried things. You weren't going to be great at it, but it was a way to not just conform and be in that thing. Now everything is geared to one direction. You know, in the seventh grade now, I want my kid to go to the Columbia University Summer School for film because that'll look good on the resume.

22:22John McMahon: So we're teaching these kids. It's all about building resume, resume, resume. Right, right. And by the time I get them, these MBAs that are average age about 29, 32, I mean, they're kind of burnt out. They're just tired of being on this Pavlovian kind of cycle of just chasing, chasing. And they're feeling kind of lost and empty. And, you know, it hasn't delivered what they've done. So one of the things I asked my class sometimes said, how many of you had a passion growing up that you really loved and name it? Oh, I like the tap dance. Oh, I like to do creative writing. I was in musical theater.

23:04John McMahon: They all start naming stuff. I said, how many of you are still doing it? Maybe two or three out of 40. Why? Why? Well, I was busy chasing what's really going to equate to success. And I said, wait a minute. These things that fed your soul when you're playing the piano and you love doing that when you were 10. Didn't that feed your soul? And then I say, well, some of you vow to me that you'll re-engage with that thing you loved. Look, if you just re-engage it for an hour a week, do you think that'll make you a better version of you? I think so. so it's funny how I'll get notes back says hey I tried out for a musical theater part in my community it's really a blast and they're they're really rediscovering the things that really bring them joy and but this is another thing Mac that's really interesting on this whole thing so I was reading this article by a New York Times uh reporter who you know repeatedly Oddly, people in Nordic countries report that they're the happiest people in the world.

24:18John McMahon: Sweden, Norway, these. So she wanted to know why. She went over and spent six months there. Here's what she discovered. It was a nation of hobbyists. In other words, if you were a quilter, you didn't just quilt 30 minutes every month. You're quilting 10 hours a week with a community of quilters. If you were an ice skater, you didn't just ice skate once a month. You ice skated a lot. So when you eventually left your company or quote unquote retired, you had a built in community. All you did is did more of what you loved. Yeah. Isn't that an interesting insight? Yeah.

25:04John Kaplan: It's a flow state. It's identifying a flow state.

25:07John McMahon: Yeah. and it's and we don't value that sometimes i get frustrated with some of my european friends because you know i'm taking another vacation i'm doing it and there's a side of me that admires that there's a side of me that says you guys don't work you know you i don't get it live that johnny and i have lived that i know it is right but but they're saying is that they work to live

25:36Doug Holladay: they don't live to work.

25:37John McMahon: Yeah, exactly. And I feel like, I see it in my two older boys who are composers and they're doing really well and doing big time compositions for the best, biggest films in the world now. But they work nonstop. They love working. It's their joy. Now, in their case, their passion is what they get paid for. And that's not a foregone thing. I feel like sometime, and I've been a part of this, a lot of people have talked about live your passion. And I agree on one hand, but I think it's frustrated some people. You tell a young person who's 20, you know, live your passion. And number one, he had no his passion is.

26:24John McMahon: But if he says, OK, I think my passion is to do X. How do I get a job? How do I support myself? So so I've come to a different paradigm. I I put two circles up. One is the things you have to do. You have to pay the rent. You have to have an apartment. You have to do all this kind of thing. Then the other circle, the things that you know make you come alive, you should pursue both. Now, if you're lucky, they might intersect and you might get paid for what you love. But it's not a foregone conclusion. And we frustrate people. I mean, I put that quote up all the time by Mondavi. He says, you know, do the thing you love.

27:11John McMahon: You'll never work a day in your life. Well, that's wonderful for him. But there's a lot of young people who told me, Doug, how do I do that? Where do I go to find that kind of job that I'm going to get paid for?

27:27Doug Holladay: You know what I also did, Doug, is going back to the Boston College study. I tried to see, because we have a lot of enterprise software salespeople on the podcast. And I tried to say, what's the sales version of that? And in a book named The Challenger Sale, they categorized sales pros, sales professionals as five different groups, the relationship builder, the hard worker, the lone wolf, the reactive problem solver, and the risk taker. And then what they found out is that the risk taker wins overwhelmingly dominated top performance, especially in complex enterprise software sales areas where it could take you nine months to a year to sell a deal, right?

28:18Doug Holladay: Because they were willing to assertively push back on clients and disrupt conventional thinking in order to deliver value for the client. Whereas the generalist, almost the same as that, uh, the BC study, those people became relationship builders. You know, they were the ultimate pleaser person. Yeah. Yeah. Valedictorian, you try to keep all the teachers happy. Right. Yeah. Yeah. The generalist or the pleaser was least likely to succeed, you know, and that's, I love that.

28:54John McMahon: I love what you're saying. That's so interesting. and it's the very thing that probably the client doesn't want to hear but if they try it to me that gets back the trust will someone trust you to take them in an uncomfortable place yes yes this is what we do sometime at path north i was thinking about you know thinking about joining you guys this morning i was thinking about in san francisco we have we've had these things called salons all over the country where you have 35 40 people for dinner at somebody's house or a club and i'll have a speaker or something but it's not about the speaker it's about the questions so in san francisco we had one of mike depady's house the chairman ceo of kempton group and the question that night was um what would your children say is most important to you and i tell you it was it was uncomfortable at first but i tell you in 30 minutes you had some people crying some people feeling connected for the first time and it was a magical night but it all was predicated on trust i'm going to take you to a place that's going to be uncomfortable but trust me you're going to be glad once once you get through this or when you start seeing that other people are struggling in the same way yeah in that in that

30:33John Kaplan: johnny in that challenger book i always struggled with that book i think it's it's it's translated in every language around the world. It's a very successful curriculum. But the one thing that I struggled with is like trying to put people in a box to say you are this or you are that, you are this. And what I found on this topic is it's more related to somebody's tolerance for failure. Meaning how do you view failure? And what does failure mean to you? And it's so related to both of these chapters, Doug. Like, it's so related to your recognition. I love what you're saying.

31:14Doug Holladay: Well, it basically said that, you know, the generalist or, you know, the valedictorian, essentially, and that if we look at both of those studies together, was trying to eliminate risk and trying to comply with. Failure is not an option for them. Whereas with the risk taker, they were embracing rejection and failure. And that rejection and failure became a key data point in their mind. Like, I got to change. And they changed.

31:40John McMahon: Yeah.

31:41Doug Holladay: Yeah. Whereas the other guys were trying to stay down that steady road, guardrails on both sides, and you weren't going off the guardrails.

31:47John Kaplan: And it's so related to who's scoreboard. So for me, my greatest attributes of success was I was afraid to fail because I had failed. And I kind of grew up in, not to be dramatic, but I grew up around failure, let's say. I'm loving, loving situation, but failure was obvious to me. It was scary to me. The consequences were gross. I hated them. And so I spent the rest of my, you know, my teens and then my early twenties of that's not going to happen to me. and it's my definition of failure needed to adjust because, okay, I was afraid of failure, but that same failure created incredibly loving and nurturing parents.

32:40John Kaplan: The fact that I just didn't have money like everybody else did or what have you. So I had to reconcile that. So it's like your biggest strength can become your biggest weakness if you're not aware. So Doug, what I love about you and what you teach and what you talk about is the how to become aware. So like I say, it took me some freaking therapy and some freaking bad stuff happening to me. I don't want that to happen to other people. Like our audience, like how do you learn these things earlier in life?

33:12John McMahon: How do you do it? I love, boy, I love what you're saying. That's why I love teaching these MBAs. But this is another data point for us. There was a 1962 study called The Cradles of Eminence, and it looked at the lives of 400 famous people in the 20th century. You know, Henry Ford, Louis Armstrong, on and on. People like that. Roosevelt. The interesting thing was 75 % of them grew up in a very difficult, dire circumstance. It was either utter poverty, hopelessness, a non-nurturing thing. But it was the very engine that really birthed them to be great. Now, this has – so today, the people that you would name that would be along that line would be people like Howard Schultz and LeBron James, who all grew up in that kind of circumstance.

34:17John McMahon: But here's the challenge. Here's the challenge for, and this is a depressing thought to give some of our people that are listening to us, but the most accomplished who have actually done so much better than their parents and they're sitting on some, however you measure success, some kind of success, what they want to do is protect their children from the very things. 100 % that that made them amazing so the very thing that fueled their passion we're protecting them from it so so I have a woman that works for me this is a very interesting data point she has three kids she was telling me recently it's interesting even since I've had kids she has one that's 10 another one that's three she said when I first started going to the playground all the parents would come and they'd sit on the benches and they'd watch their kids play okay that's fine now that's changed the parents are doing the things with the kids because they're afraid they're going to get hurt so they're going down the sliding board with them or they're at the bottom of the slide but on the side the jungle gym they're there with them so she told me this too that is astonishing they were in la with so her husband is a big-time criminal defense lawyer and they were there with their family and they put the her the all the cousins and all go in this camp every year for a week and then the parents just hang out well there was a young person there so she's raised her kids to take risks to do things they get cuts and bruises sometimes this young counselor who was 15 year old young man reports them and says there might be some child abuse going on oh my god this launched a two-week investigation into their life interviews with law enforcement and it's unbelievable.

36:29John McMahon: And they're saying, why did they have this bruise and cut? Because they're a kid and this is what you do. But everything in modern society now is creating guardrails so our kids can't figure out life. So we are protecting them from the very pain, setback, hurt that could make them a LeBron James or could make them a Howard Schultz. And I have to tell you, as somebody like that, and I see my peers the same way, it's like, oh, my gosh, what are we doing? But we want to help them. No one helped me fill out a college application. no one helped me do any of that stuff i had to figure out everything but here's the thing and here's what i learned if you don't understand because like you're talking to a guy right now who i i used to say one i was afraid that one of my children was going to be homeless

37:37John Kaplan: and i'm dead serious it's not a joke not a and my wife i was afraid of being homeless

37:45John McMahon: yeah so my wife you're passing on your narrative she would grab my face and she would say

37:53John Kaplan: they're not you they're not you now if i could have learned that so much earlier okay so that failure for me having to show up in school without having money to buy this or whatever here's the point that i wanted to make because i love you you talk about it in the book I'm in kind of a failure situation, let's say, but I don't have the experience or the knowledge or people around me to tell me that this is not how it ends.

38:23John McMahon: Yeah. I love what you're saying. And to me, to me, Cap, this this speaks to our whole educational motif. We in my judgment, wouldn't it be amazing in the seventh and eighth grade if we started introducing these things? Hey, some of you have grown up in really hard circumstances. We just want to tell you that's not the end of the story. And let me what we're going to do every week, we're going to have one hour where during the course of the week where we're going to talk about the life of somebody that's overcome something despite adversity. All of a sudden in the seventh grade, you're putting in the mind of that young person.

39:09John McMahon: Wow. The fact that my father's an alcoholic or my mother abandoned the family. That's not the end for me. I don't have to repeat that story. I can make other decisions. But we don't give you're right. We don't give anybody any learning in that area. We don't give them any instruction. And if they're lucky, somebody will give them a book that might help them someday. But it almost requires a certain, I think, I think a certain point in your life, a certain epiphany where you either suffer greatly with a medical issue or your wife leaves you or a death of a close friend. something that causes you to say, oh my gosh, the world is not stable.

40:10John McMahon: What are my points of reference that are enduring that I have to really focus on?

40:18John Kaplan: So for me, this is leadership. Like anybody listening, one of the greatest skills that you could have is to help another human being be present in their suffering. and to also help them realize, in your book, one of my favorite stories is the Zen master and the little boy. And I saw that in Charlie Wilson's War. And Doug, if you wouldn't mind just sharing with us the power of really that story, and it's based on this kind of we'll see. Now, if somebody had shared that with me when I was 10, we'll see how this turns out my life would have been a little bit it wouldn't have been easier wouldn't it just would have been i would have been more aware so first share the you know i just want

41:11John McMahon: to underscore you know putting these things in because i think we we assume that younger people can absorb this at a young age look look i i you know you guys have been in my class and you see i when these kids tell these stories I come from, I think I was shocked because these are the best and brightest. And all of a sudden they're saying, I lived in a car with my mother for two years. I had to be raised by a grandmother because my parents both died. You start saying, my God, they already have experienced a lot, but what they're not getting is the interpretation of how that could be transformative.

41:56John McMahon: in their life. You know, there's a guy in Princeton. I thought this was so funny, but really wonderful. So his name is Johannes Hoffenhauser. And this guy has, you can look this up. It's called a resume of failures. So he felt like everybody looked at him. I'm a professor at Princeton. I have a PhD from Harvard, all this. Great. he said you know i realize that narrative is total bs so when it's on his resume it has of failures has here's all the phd programs i was rejected for here's all the grants i didn't get here's all the tenure you know the the interviews i had at different colleges that wouldn't hire me He just put one failure after the other.

42:49And I thought, that is great.

42:52John McMahon: Because people need to know, it isn't like you have this golden list that, oh, everything's fine for this group and the rest are losing. It's not that. It's somebody that has decided that they're going to let this pain fuel them. And they're not going to say no. And the people that I admire the most are the ones who have been fueled by suffering and hardship. And you wouldn't want that. But unfortunately, it seems like not only is it the essence of success, but it's the very thing we as privileged people now are trying to protect our kids from. And is it any wonder that they're entitled? They aren't motivated.

43:45John McMahon: They don't care about much, a lot of them.

43:48Doug Holladay: Going to that point you just made, I don't know if you guys saw the speech that, commencement speech that Roger Federer did.

43:55John Kaplan: Yeah.

43:56Doug Holladay: We talked about how in his life, he's won probably more games, more sets, more matches than any other player in history. However, he lost the majority of points. So you have to have that. Even if you're at the top of your game, you have to have this mindset that to get to the top, chances are I'm going to lose more than I win. That's really great. A lot of people don't have that mindset. They lose once or twice or three times and they throw their hands up in the air.

44:28John McMahon: Well, there's a lot of shame. There's a lot of shame. And it comes back, as Cap was pointing out, to our story. If you grew up in a shame culture where your parents are always disappointed in you or teachers or whoever, it's almost like you try to hide that stuff as much as you can. and then what I'm suggesting is instead of hiding the very things you're ashamed of if you start to share those things all of a sudden you find community and connection because everybody has stuff they wish they hadn't done everybody has disappointments that they're just surprised at

45:14John Kaplan: this point for our audience is such a home run Because if, and we talked about this before on previous ones, it's this, it's this, I learned this concept through my father's generation and my father's background is this concept of sitting Shiva. Oh yeah. The Jews have this concept of sitting Shiva, which means you're there for another individual to be around them in their suffering. You're not supposed to try to get them out of their suffering. You're supposed to be available to them.

45:53John McMahon: Well, you said entering and being present for people. Yes.

46:01John Kaplan: This is leadership. This is leadership, and I think the greatest leaders I've ever been around are the ones who can recognize suffering, and they don't try to fix the suffering for the seller. They don't try to fix the suffering for the child. They try to first sit Shiva, which means I'm going to sit with you in your suffering, let you talk about it, and then if you come to me, I'm going to give you perspective about how long that's going to be. that suffering lasts, or I'm going to share something with you about my own suffering. The greatest leaders, the most authentic leaders I've ever seen are the ones that share something with you in your moment of pain that you didn't know about them, that gave you a different perspective on how long you were going to be in the suck.

46:54John Kaplan: And I think that's a huge huge leadership attribute, huge.

47:00John McMahon: I love that. I love that because I think the typical leader and probably a lot of people listening to this, we're taught we've got to have answers. The longer I live, I feel like it's more about learning the right questions. And for me to say, what is the thoughtful question that I can ask Mac, you know, how at this point in your life, are things working the way you had hoped? What happens and see, I believe we run business meetings all wrong. For example, you have, let's say I have 10 people that report to me. So I have a huge problem. I just lost my biggest client. So, of course, I bring 10 people together and say, yeah, what are we going to do?

47:57John McMahon: OK, 10 people are there. The two people that always talk the most are going to come up and they're going to have ideas and blah, blah, blah. And we're going to be right back to where we were. What if we change the narrative and we said instead of trying to find the answer, let's all take 10 minutes, write down two questions that are going to help give us insight into how we lost that client and how we can get them back so everybody this little meek woman that never speaks writes her two questions so everybody has a question or two all of a sudden the conversations enlarge and guess what we're going to have a better outcome but when we just are looking for answers it's always going to be the know-it-all who was the valedictorian everybody said you you're the smartest you got and it's going to be the same old thing every time yeah doug one of the other things you talk

48:58Doug Holladay: about in your book is that um this is drd4 variant of the oh yeah receptor d4 gene and it's been nicknamed uh the explorer or the wanderlust gene and like a hundred percent of the population has it. And the reason I think you mentioned is it blunts the dopamine receptors, make them less sensitive to dopamine. And dopamine's a neurotransmitter that is linked to motivation, attention, and reward. So when people have this gene, their dopamine is blunted, and they require more risk and more uncertainty in order to feel the same sense of reward as a normal person yeah yeah um so there are some people that are born with a risk oh yeah right i think i was the guy that climbed you know uh yosemite climbed you know that rock wall with no ropes oh yeah I was going to say, I met that guy and I talked to him afterwards.

50:12John McMahon: And we were out in California and he's climbed unimaginable things that are unclimbable. But he does it without ropes. Now, he was telling me that all of his climbing partners have died. Yes. And he's married and his wife keeps saying, when are you going to stop this? his view of his life is if I stop doing this, I'm going to die. Yeah. So he's almost defined himself by this adrenaline he gets from doing this crazy thing, even if he dies. So it's a very, I mean.

50:52John Kaplan: It's a fine line. It's a fine line. We're all examples of our biggest strength can become our biggest weakness if we're not aware of our strengths and weaknesses. That's the message that I continually get from your book. We're all in a situation, if we don't have the ability to be self-reflective about where we are and what's going on. For example, for me on risk tolerance, for me, John Kaplan, I got Katie barred the door. I've got all kinds of examples. I packed my bag and I went to Boise State one-way plane ticket with a duffel bag that's because it was me and and i thought i was alone and i didn't well then you get a family and all of a sudden my wrist tolerance changes i'm still the same john caplan but now i have others in my crew yeah and it's like and i was lamenting i used to say to my wife where the hell is that guy that freaking had one duffel bag got on a freaking one-way And she was like, she was, she's constantly telling me, like, you got to be really grounded in where you are right now and have an understanding.

52:05John Kaplan: It's not that person is lost. It's that person's still there. You just, you're responsible for more. Yeah. It's this constant struggle of knowing where you are right now.

52:16John McMahon: Well, you, you said at the beginning of this, Captain, you know, how, how at a younger age do we become reflective? And I'd say if I were the listeners, I'd write down this Socrates quote and I would read it every day for a month. And it says the unexamined life is not worth living. So good. Now, the question is how we're in an age that doesn't examine. We're moving so fast. And part of that is the pain of of doing the work of going deep. But I'll tell you, listeners, you're not going to die if you start looking at your stuff. your why it might it's going to raise some awkward things and all that kind of stuff but don't you want to know it don't you want to be just be curious about your own life and if you have relatives that are still around parents or grandparents or uncles and ask them questions because so much of your narrative was shaped by all that that system of that web of relationships that were around you.

53:23John McMahon: But most of us don't take the time when we're young to really pause and consider. And that's the unfortunate thing. And because we don't prize that. We prize, you know, and you guys are in the tech world, move fast and break stuff. You kind of say, you know, that's the mantra. But you also say, wait a minute. What's going on inside of me? Because that someday I'm going to have to deal with me. Why don't we start the process a little bit now? Start to really do some reflection. You're not going to die. And particularly if you do it with some other people, you know.

54:08John Kaplan: You know, part of it is this. What I learned through my own struggles in life is that you are you view those struggles with whatever glasses you had on when. And so a lot of my stuff comes from my younger self, let's say 10 years old. Well, those glasses on a 63-year-old, when you take the opportunity to put those glasses on, you're like, the world doesn't look like that. But we're stuck. The problem is we get stuck at the time of the experience. So if I was 10, I'm 63, and I still feel like that's happening, but it's not reality. And the only way around that is to, and I don't mean to be prescriptive to people.

54:53John Kaplan: I just want to give them spirit. If you can sit with yourself every morning, I've told Johnny this, I sit every morning for about 15 or 20 minutes and I just ask myself, who's here? Sometimes the 10-year-old kid, scared as hell, and then Johnny and I joke about there's this 13, 15-year-old edgy, there's this edgy kid. and don't forget about squeaky that's right that's squeaky it but what i do is i just who's here today because it's gonna determine what the hell's gonna happen during the day if i wake up and the freaking scared 10 year old kid is running around i'm gonna i'm gonna project that those challenges with that little 10 year old kid or the pissed off teenager yeah yeah i think if i could just give anybody any advice on this is to sit quietly with yourself every morning before you get going and say, who's here?

55:50John McMahon: That's a great, great line. You know, Saturday night, I was, I was at this dinner. It was a guy's birthday, very wealthy guy here in McLean, Virginia, and we were there. And I'm at the table with him and this other guy, well-known guy says, So, Doug, you spend a lot of time thinking about what's going on with men and leadership. Why do men, what's wrong with them? What's going on? And I'm thinking, I don't know. I didn't know anybody at the table except the birthday boy. And I knew this other guy. And it was like, it's funny how when I laid out a couple things, I'll just say, well, I'll just suggest a few things.

56:35John McMahon: but everybody kind of comes at that you had one guy really defensive says hey my life's mine i'm good i'm i'm fine yeah it was like everybody they had to stake out a very strong position uh to defend why they haven't been self-reflective why they haven't done the work and i'm not accusing anybody of anything but i do know if you right down the street here is the cia If you go in there in the center, right on the floor, it has a verse from the Gospel of John. It says, John 10, 10, it says, you'll know the truth and the truth will set you free. The beginning of change is to face the truth. A lot of us want to have a fanciful view of our family.

57:24John McMahon: Oh, they were great. They're all this bullcrap. And it's really not true. So we bought into that narrative because we're afraid to talk about it because it feels disloyal. It feels all this kind of thing. But until you can face the truth of the world that shaped you, you can't move on. You're still perpetuating a lie and about yourself and about your family and all this. So I'd say to start to do the work requires some, you know, bravery really requires, you know, Brene Brown says, you know, to under to to really understand and embrace your story is the bravest thing any of us can ever do. and it really is it really takes bravery to face it because a lot of times we don't want to face that my father was an abuser or my mother had a screaming raging temper you don't want to acknowledge whatever that dark story is in your life but until you do it says in the book of Psalms the sins of the fathers are visited upon the third and fourth generation It doesn't go away, friends.

58:46John McMahon: If you're not doing it for you, do it for your kids. You don't want them to continue a narrative, and they will. So one illustration of how insidious this is, I was shocked one day to discover this. When I found out that children who had been sexually abused by an adult, many times, preponderant times, abused their own children. You would think that's crazy. They would never do that. So why did they do it? it was the closest thing they had to closeness to their caregiver. So even though it was sick and horrible, there was a weird kind of closeness. So you realize these patterns, and this is what's happening in our lives.

59:47John McMahon: Why do we keep repeating these patterns? Because they're familiar. Yeah.

59:52Doug Holladay: Even though it's called In My Father's House, and it's about all the fathers were crying. They were robbers. They were thieves. They were those types of things. And all the kids wind up doing the same thing. So unless you decide, it's almost like what I'll say.

1:00:13John McMahon: If you're lost in the woods, step one is say, I'm lost. Right. Which is hard for men. Hard for men. And then the second step is, OK, once you realize you've got a problem, OK, how do I navigate? Who are my guides? What information do I need to try to make better decisions? And there's help for that. I mentioned to your people, I've been helped by some really good, you know, good kind of workshops. So seek out these things that help you understand where you're going. I mean, Cap, you mentioned therapy and stuff. You know, just it's I think, again, certain people have a stigma about this, but it's trying to just understand the riddle of our life.

1:01:04It isn't like blaming.

1:01:06John McMahon: It's all that. It's talking honestly about your story so that you can change that story.

1:01:13John Kaplan: In my case, Doug, I had created this narrative that it was so nasty that I kept running from it. The funny thing is, it's in my head. It never goes away. And until I sat with people that could help me understand that what's in my head is not as scary as I think it is, it's really freaking powerful. But I'm telling you, we're talking like we're talking in in my 50s. Yeah. God. But I want to give people spirit. If you're listening to this and you're 30 and you're struggling with some stuff, don't wait till you're 50 or 60. You're just going to waste a lot of time.

1:02:01John McMahon: Yeah.

1:02:01John Kaplan: A lot of pain.

1:02:03John McMahon: Yeah. No, you're absolutely right. And and I at some point there's a reckoning that we all have to face. But don't you want to do it when you're healthier emotionally, physically, and you can deal with it? You just don't want to be that guy that just has all these regrets. You know, it's funny. There's this woman in Australia that she did a study about. She was a palliative nurse. So she said, probably I've listened to, you know, 3 ,000 stories of people on their deathbed about their regrets. And so many of them, the number one regret is they, rather than live the life they should have lived, they lived the life that others expected of them.

1:02:58John McMahon: That was the preponderate regret. The second one was I would have taken more risk. Yeah.

1:03:07Doug Holladay: Excellent. Doug Holiday, always special to be with you, spend time with you. You're one of a kind. We're glad to have you in our life. Likewise.

1:03:21John McMahon: Thank you. Thank you.

1:03:22John Kaplan: And Johnny, let's just plug again. Like we sometimes we forget because we've been doing this for so long. You want to get plugged in to what we're talking about and go back. We have, I think this is the fourth or fifth one that we've done with Doug. It comes from his bestselling book called The Rethinking Success, Eight Essential Practices for Finding Meaning. Is it at the end? Is it within? What is it at the end? eight essentials. What's the last part?

1:03:53John McMahon: Eight essential practices for finding meaning in work and life.

1:03:58John Kaplan: In work and life. Sorry, I got it cut off there. But dude, you're such a joy, and I'm always better after these podcasts.

1:04:07John McMahon: I feel the same way. I love what you guys are doing because you're creating space for people to think, explore, because ideas have power. Remember that If you get one idea out of this, it can be transformational. Victor Hugo said there's nothing more powerful than an idea whose time has come. There might have been an idea you heard today that for the first time, it's come. It's the right time for you to act on it.

1:04:38Doug Holladay: Amazing. You're amazing, Doug Holliday. Thank you so much. Thank you, John Kaplan. Thank you, guys. All right. Thanks to everyone for listening to another episode of the Revenue Builders Podcast.

1:05:16Don't.