Is Luck All In Your Head?

Dan Sullivan: Hi, everybody. This is Dan Sullivan and this is “Anything and Everything” with my partner, who I got to spend some time with. Usually it’s strictly Zoom, but we were able to be in Arizona for three or four days at a conference. So this is Jeff Madoff, and the man of many talents, has a great project that Babs and I are enormously interested in. It’s a new Broadway-bound musical by the name of Personality, about the life of Lloyd Price, who was the great crossover artist who really, really launched rock and roll in the early 1950s, which both of us were actually on the earth to witness, Jeff.
 
Jeffrey Madoff: Yes, we were barely sentient beings at that point, but we were there. Rumor has it that I left my mother’s body tapping my foot to a rhythmic beat.
 
Dan Sullivan: Yeah.
 
Jeffrey Madoff: But you know mentioned we were just at a conference. We were talking before we started recording about some of the components of success. And you made an interesting statement, which was about luck. What is your perception of that, and how does that relate to being successful?
 
Dan Sullivan: Well, I think, this is my personal philosophy, so in my case, I can certainly say that I think that 50% of what I now count as my success in life is certainly because I was lucky at the beginning, because I won’t say I had perfect parents, but I had perfect parents for me. I’m one of seven—unusual birth order: I have four olders, big gap, there’s me, big gap, two others, so I was kind of an only child in the middle of a big family, which had enormous benefits because I got to spend my first five or six years just one-on-one with either my mother or my father together. Grew up on a farm. I had no playmates whatsoever until I started first grade at six. And very, very healthy, I’ve been healthy and fit all my life. Was born with a good enough brain that I could become successful.
 
And I was born in the generation before the Baby Boomers, so the Boomers, generally the year given for the biggest generation ever is 1946, and I was born in 1944. So up until that time, I was in the first generation that was smaller than the generation before, which meant that when you got to school, the teachers had massive amounts of time for you, and the resources that were available were more than enough in the 1950s. I grew up in the 1950s, and it was a boom-time in the United States. Then when I graduated from high school, there was more than enough jobs.
 
So it’s been a very, very abundant life. When you’re born and what the conditions are, when you’re born and what accompanies you throughout life I think it’s a roll of the dice. So when I hear about people successful, you’re a self-made person, well you are, but you have to realize that you could have been born with less resources. You could have been born with less opportunity. So I feel that I have very, very good luck. But the other component, so there’s a second component to that, so that’s just my answer to the first part of your question.
 
Jeffrey Madoff: Well, I’ll give you a quick story about what you said. I was doing a documentary on Brooke Astor, who was the cornerstone of philanthropy in New York, Metropolitan.
 
Dan Sullivan: Of the Astor family.
 
Jeffrey Madoff: That’s right.
 
Dan Sullivan: Yeah.
 
Jeffrey Madoff: And we went to a halfway house. She was going to drop off this coat to this woman there. We went to the woman’s room, and this is run by two Franciscan Brothers, and there was a shot of her as a young woman on horseback jumping over a hedge. She went to Choate. She was clearly from some wealth. And Brooke gave her a coat, and she put it on and thanked her and Brooke hugged her. Then when we left, all of the people from the halfway house gathered in the bottom of the stairs and hugged Brooke, and it was beautiful.
 
We get into her car, start shooting, and I said, “Now where did you meet this woman?” She said, “I was going down Fifth Avenue, and she was rolling in the street, bellowing, screaming.” She had been broke. Her husband was a doctor of some means, but when he got sick, all the insurance had run out. It broke them and she lost it, ended up in this halfway house. Brooke rescued her. And I thought that was pretty amazing.
 
And then, Brooke looks the other way out the car window. And I said, “You seem to be very comfortable in that situation and with these people. And you seem to have a compassion for them that is very touching.” She looks back out the window, then she comes back and tears are streaming down her cheeks. And she said, “There, but for the grace of God, go I.” And she realized oftentimes there’s very little separating people, the good luck and the bad luck, and where you could have ended up. And I thought that that empathy and compassion she had was just beautiful. What it made me wonder though, and I didn’t ask her this question, but I’ll ask you is, what is luck?
 
Dan Sullivan: Well, luck is circumstances, for one thing. It means a great deal who you’re born to. I don’t mean whether they’re wealthy or whether they’re famous or anything else, but first of all, do they think that your being born is a good thing for them?
 
Jeffrey Madoff: Right.
 
Dan Sullivan: I think that’s one thing, it’s just what their general approach is to the fact that you were born to them. For me, I think it was probably a good time in my parents’ life because we’re blue collar, and not poor blue collar, but “just enough” blue collar, grew up farm country and that. And you never had a sense that you were deprived, but there was just the amount of money that was necessary to be clothed and eat, but you know it was close to the line.
 
But I always had the sense that my parents liked me. And I won’t say they were especially interested in me, but I always had a sense that they meant well for me. And I think that takes a lot of burden off your life, just the fact that the two most important adults that are responsible for your early life said they basically like you. And they were very good-willed, and they’d come from two families that were not good-willed at all. They come from big families and they’re both fifth children, so I share that with them, that I am the fifth child of two fifth children. And I never really thought about that till long after I was gone. I never zeroed in on that.
 
But my father, because he had four kids before the Second World War started, he was exempt from the draft, but he went to work in a war factory, actually really interesting, and it was in Cleveland. Jack & Heintz was the name of the factory. And there’s some interesting stories written about this factory, and they made gyroscopes for the fighters and bombers, the thing that kept the airplane on an even keel. But the government just threw money at these factories, so they had enormous benefits for their workers. They had food all the time and you got free meals when you went there, and it was double pay for overtime and everything.
 
So I think it was a good period economically for them, and they saved a lot of money and they bought a farm right after the war was finished. But I just had a sense that I was born during the period of time when my parents had things a lot easier going for them.
 
So what is luck? Well, it’s a roll of the dice, I think. Some people never know why they were born. They don’t have any idea what life was supposed to be about. And I was given enough freedom and enough time that I was able to develop a pretty confident sense about who I was and what I was good at and what I was interested in. So I count the conditions into which I was born really lucky.
 
Jeffrey Madoff: It sounds like a simple phrase, “My parents liked me.” But it’s not so simple, because we both know people that are quite damaged in one way or the other because they never felt they had that parental love or caring that you were talking about.
 
Dan Sullivan: Yeah.
 
Jeffrey Madoff: Which is, I think, huge. I believe so much goes back to basic issues, and then how your life manifests itself, how you deal with those things. And my parents were solidly middle class. They owned their own business. My mom and dad were both entrepreneurs. And when they were going through difficulties financially, and they did, but I didn’t know about that till way after I had moved away from home and gone to college and I was a young adult and talked to them about that. That was the only life and context that I knew. So we were always well-fed, always well-clothed. It didn’t seem... Nothing extravagant. We didn’t do family vacations or anything. And I still don’t. I’m pretty bad at that. But I think that we only know what we know when we’re kids, and our only frame of reference is the context of the family we’re born into at that point.
 
So I think that that’s interesting. But I think, and I’m curious of your opinion, I think the nature of luck and how that manifests changes as we get older. You’re talking about the basics, born into a family that cares about you, that loves you and you have freedom to express and do. Then we get it into adulthood, and those of us who either start their own businesses or go to work or whatever, I think luck takes on a different meaning. And the kind of, it’s not even a metaphor because it exists, let’s call it “the Las Vegas factor of life” when you talk about the role of the dice. And what do you think luck becomes as you get older and as you’re pursuing your career and trying to make money?
 
Dan Sullivan: What I’ve noticed is how long do you remain a child?
 
Jeffrey Madoff: That’s interesting. That’s good. I like that.
 
Dan Sullivan: And I know 50- and 60-year olds who never left childhood. There’s a sense of entitlement. When we’re children, we’re given a lot of things. You go through a week and you get a bill for the meals. That’s not a good childhood.
 
Jeffrey Madoff: No.
 
Dan Sullivan: But there is a sense that you’re not an individual on your own with a lot of people. And I really saw it during COVID, that a lot of adults just responded like children. They didn’t really get a grip on, “Look, circumstances are changing. You probably have to change your strategy. You have to change your approach. You have to organize.” And I think that people who are not entrepreneurs and are used to employment and they’re used to somebody else creating employment for them and creating income for them, when they’re confronted with something like that, my sense has been that they’re more worried because they actually have far, far less control over their future. You and I have control over our futures.
 
Jeffrey Madoff: Do we?
 
Dan Sullivan: But we’ve chose at a very early age to do that.
 
Jeffrey Madoff: Well, or believe we have that. But do you think we really do?
 
Dan Sullivan: Sure, because you believe it.
 
Jeffrey Madoff: Okay. Uh-huh.
 
Dan Sullivan: I think it’s in the belief that you do. If that’s your belief, then that’s your mindset and that’s your behavior.
 
Jeffrey Madoff: Right.
 
Dan Sullivan: So my sense, your belief about who you are and what the future holds for you, really, really determines the mindsets with which you approach it. And also, the mindsets translate into behavior, what you can be counted on to do all the time.
 
Jeffrey Madoff: That raises a really interesting point to me. I think that you’re right.
 
How much of one’s belief or confidence, and I’m not even sure how to articulate this because I think there’s things that you learn and there’s a lot of things that you don’t necessarily need to know how to do, and that’s a tip of the hat to Who Not How, your book with Ben Hardy. But I think that there’s something really interesting there when you believe that you can accomplish something, with frankly, no real world support initially that tells you you can. So you make that leap of faith, if you will, that, “I can do this.” Now that can be delusional or that can be true. But I’m wondering, what do you think, because you’ve dealt with so many entrepreneurs, what do you think that gap that they have to leap is between self-belief and behaviors as you said, and action to bring those dreams you have to life?
 
Dan Sullivan: There’s probably a book in this as I go into this, but for some reason certain individuals are self-defining. In other words, what other people’s opinion of them is might be useful information, but it’s not of central importance to them, that they have a certain sense of who they are. They have a sense of what they’re capable of doing. They’re having a sense that, “It’s a brand new situation and I don’t have knowledge about it. I don’t have experience of it, and I don’t have a reputation. And what I’ve done before, it doesn’t necessarily get you paid in this new situation.” They have a sense of how they’ll go about succeeding in a new situation.
 
One of the things I often talk about is that there’s very much of an immigrant quality about the mindset of entrepreneurs. The statistics are plentiful that tell you that immigrants to the United States over the course of a lifetime do about twice as well economically as native-born Americans. And I said, “Well, the reason is that they only allow you a certain amount of baggage on the plane. So you have to choose to leave a lot of things behind, because you’re not going on a trip, you’re going on a life when you do that. And you leave behind relationships, you leave behind connections, you leave behind a lot of meaning that meant somewhere back there, but it doesn’t mean anything in the new place. So you get there and you know have no references, you have no reputation, you have no credentials. But what you do is that people need people who are useful. And so, you look around for ways of being useful.”
 
So I think that entrepreneurs, the homeland that we live in, for most people, 95% of all people who work in their life, do it as an employee in one description of that or another. And entrepreneurs are immigrants. They don’t come from the employment world or they leave the employment world behind like they’re leaving a country behind. They’re leaving all the meaning of employment behind, and you’re going into a strange new territory.
 
So the answer to the question that you asked, “What is it that creates this common belief?”, it’s that “It doesn’t matter where they put me, I think I’ll figure out how to succeed.”
 
Jeffrey Madoff: Which is survival.
 
Dan Sullivan: Yeah, well survival first. But then, you tell stories about creating your own place when you were younger than 10 years old and having audiences and creating the movie experience for them in the basement of your house. And I have a lot of that. I have a lot of that of self-employment in my teens, not so much because I was still on the farm.
 
Farm experience was great because you knew you had a role, and the role was important and you had to do your role. And I think that was very useful information at a very young age. I think the biggest problem that children have today, no matter how much their parents love them, children know pretty quickly that they’re an expense.
 
Jeffrey Madoff: Yeah. It’s funny, I was walking my daughter to school, she was in third grade, and my kids had gone to a Montessori preschool before that and they were in private school. And as we’re walking, she looks up at me and says, “Dad, do you know that you have spent more than half a million dollars on Jake’s and my education so far?”
 
Dan Sullivan: This is third grade.
 
Jeffrey Madoff: Just third grade, yes. And I said, “I’m painfully aware of it, and I would love to have some indication that it was worth it.” And she said, “Well, Dad, in this highly competitive world out there, you wouldn’t want Jake or I to go out there unprepared, would you?” And I said, “All right, be quiet. We’re almost at school.” And the funny thing is, she dropped out of college after her first year and has built a very successful career.
 
Dan Sullivan: Yeah.
 
Jeffrey Madoff: And my son stayed in school because he had a real mission. And he completed that mission and is also entrepreneurial, well as you know, as a matter of fact. So it’s really interesting, that child’s perception. But I really liked what you said about the choices that people coming to this country have to make, because it’s both a metaphor and a reality at the same time. You’ve got to leave the baggage. You’ve got to decide what’s most important for you to bring because there’s only so much you can bring. And I think that that’s really fascinating, because that’s kind of true throughout life.
 
Dan Sullivan: Yeah.
 
Jeffrey Madoff: You have to make choices and so on, and I think that’s critical.
 
Dan Sullivan: Yeah. It’s really, really interesting. I think you know who he is, but this isn’t about the person, it’s just about he has an interesting story to tell, Chuck Woolery, who is a famous-
 
Jeffrey Madoff: He was a game show host, right?
 
Dan Sullivan: ... Game show host.
 
Jeffrey Madoff: Yeah.
 
Dan Sullivan: He was involved in seven very, very successful game shows over a 40-year career. I met him through a friend of ours, and we were talking, and I said, “Boy.” I said, “Probably one is really great, if you get one. You’ve had seven.” I think he might be from Ohio, or he is from Kentucky, I think he’s from Kentucky. And he grew up in the country and, you know, a farm kid in the country. And he said, “I had a really unique technique.” And he said that, “I know that if you stay with something successful for too long, you lose your skills for doing anything else.” Okay? And so, he said that, “There was a time period when I said, ‘I’m right at the point now where this is enough of this success, and now I have to go out and create another success.’”
 
And what he did is that he always, when a new venture came along, he always went back to basic pay. And he said, “We’ll get paid if it’s successful.” So when the producers came to him, they always could come to him because they knew that if they were starting something new, he would be as a little economic burden up-front as he could be. And he said, “And there was some magic in that,” he says, “where you say, ‘Look, we’re in this together. I don’t know if this is going to work, but you don’t have to guarantee me success before we have success.’”
 
Jeffrey Madoff: Now, did he do that in exchange, ask for a part of the business?
 
Dan Sullivan: Sure, sure.
 
Jeffrey Madoff: Because, “In it together,” you’re really not, unless you’re also an owner and sharing in the risk, too.
 
Dan Sullivan: Yeah. And no, some of it, he would put money into it, too. So he just had this winning formula: “Don’t be a burden when something new is starting.”
 
Jeffrey Madoff: Yeah, it’s great.
 
Dan Sullivan: So you could say he was lucky, but that seems to me a skill of almost attracting luck.
 
Jeffrey Madoff: Well, and luck is also, I believe like as the phrase, a roll of the dice. It’s a numbers game. It’s rare, but it happens that people are lucky the first time out. Sometimes it takes a few times to get lucky. It’s not a guarantee.
 
Dan Sullivan: Yeah. Joe knows this actor, Glenn Morshower. Do you know who Glenn Morshower is? He was on “24” with Kiefer Sutherland. If you saw him, you’d know him because you’ve probably seen him 20 or 30 times. But he’s just one of those actors that, “What’s that guy’s name? And what’s that guy’s name?” And you see him, and there’s two parts to what I just said: You don’t know his name, but you’ve always seen him. Okay? And actually, he’s been acting now for 50 years and he’s never gone through a year unemployed. He’s never gone through one year as an actor. When you consider that 90% of actors spend 90% of their careers unemployed, that’s a major feat.
 
Joe meets him every year at Sundance. Joe goes to the Sundance Festival and he’s there, and they get together and they talk. And one thing he said, “I knew right from the beginning is that I wasn’t a star. I would never be a lead actor. I would never be on the marquee. It would never be ‘Glenn Morshower’ and everything.” And he said, “What I realized,” he said, “I got a very, very good instinct for how things looked for the producer and director of a new film. If they can, if they’re in a position, they have to go for the stars because the stars pull in the early dollars. They pull in the early audience.” But he said, “They get down to about number six on the list, and they just want to be able to pencil in names and not have to worry about it.” He says, “So I’m the ‘no worry, Number Six’ in anybody’s cast.” And he said, “I’m always prepared. I always know my lines. I’m a good person to have on the team.” And he said, “You get nothing but cooperation out of me in any presentation.”
 
Well, that’s a skill of attracting, I think it’s a luck business. I think the entertainment business, it’s like the fashion business. You may not be the fashion of the month, but in the things that you can control, make yourself a prime candidate for luck.
 
Jeffrey Madoff: I have another actor story. I think it’s really interesting, because if you say yes to something, by proxy, you’re also saying no to other things. And making that decision, I think, is really important. I have an interesting story about an actor, because what you say no to and what you say yes to are decisions that affect the other side. When you say yes to something, by proxy, you’re saying no to a number of other things.
 
I was at Ralph Lauren’s 40th anniversary party. Seated across from Ralph was Dustin Hoffman. And I approached him and told him, I had just seen him on Actors Studio. He was fantastic and generous with the actors. And he said, “Thank you.” And I said, “There’s a question I’ve always been wanting to ask you, and I’d like to ask you now.” And he said, “Okay.” And I said, “I know your first film was Madigan’s Millions and we won’t count that.” And he said, “Yeah, I don’t either.” And I said, “So your first film that put you on the map was The Graduate.” And he nods his head.
 
And I said, “You were great in that. And that was a great film. The next film you did, the character was totally the opposite, couldn’t be more different. And that was ‘Ratso Rizzo’ in Midnight Cowboy.” And he said, “Yeah.” And I said, “Was that a conscious choice, that you wanted to do something so different from that part that made you so famous in an Oscar-winning film, to show that you had range so you wouldn’t be typecast?”
 
And he stands up and he shakes my hand again, and says, “What’s your name?” And I told him, he said, “Nobody’s ever asked me that.” And I said, “Was it a deliberate calculation?” And he said, “I didn’t know I was going to get Midnight Cowboy’s script to read. I did know I was 34 when I did The Graduate, and that all I was getting was offers for romantic comedies. And I knew I couldn’t do those anymore, because I would be totally typecast and never get another part. I was too old. And I wanted to have a more expensive career. When I read the script for Midnight Cowboy and saw that ‘Ratso Rizzo’ character, I knew that I wanted that part. So yes, I knew I wanted to expand my range so I could get more jobs. But no, I didn’t know that I was going to get that script.”
 
There’s the luck part of it, right? Yeah. And of course, it had the effect that he had hoped for, because he got such a range of parts that he played because he’s such a gifted actor. But that first decision he made really early in his career to say, “No, no, no,” to those other romantic comedies and then finally say, “Yes.” And he was a very hot commodity at that point after The Graduate. Then saying yes to ‘Ratso Rizzo’ that was so different, I think that was a fantastic calculation. And I think it’s a calculation we often have to make in business.
 
Dan Sullivan: Yeah. We can have a great conversation about this for a couple hours, but the one thing I know is that you don’t get any closer to understanding why you had luck when you had luck, but you do understand that you have a method of how you approach almost anything. Okay?
 
One of the things that I found really gratifying about the COVID period as it affected entrepreneurs was the number of entrepreneurs—we had a lot of entrepreneurs in Coach who just, we didn’t see them during those two years. They just weren’t there. So probably 40% of who were in the Program in March of 2020, if we saw them at all, we didn’t see them for two years. They waited till it was over, and then some of them have come back and some of them we haven’t seen at all.
 
But the 60% who stayed were remarkable, in the degree to which they saw this as a big opportunity, going through these two years, that there was so much coming unhinged in the normal course of business that it just gave a tremendous amount of openings for new ideas, new methods, new products, and new services.
 
So it might be that the real roll of the dice is that there’s going to be a certain percentage of humans who see things that others see as danger and defeat and background, but they see it as opportunity. It just may be that there’s only a certain percentage of people who are going to end up doing a podcast talking about luck or bad luck.
 
Jeffrey Madoff: Well, it’s interesting to me because, again, going back to that phrase, and I’m always interested in where phrases come from, because “roll of the dice” also means risk.
 
Dan Sullivan: Yeah.
 
Jeffrey Madoff: You don’t know when you’re going to roll the dice, unless they’re loaded, you don’t know what that roll of the dice is going to yield.
 
Dan Sullivan: But it also means that you’re in the game.
 
Jeffrey Madoff: There you go, exactly right. You’re in the game. So then, that raises another question I think, that’s quite interesting, is “How do you know?” How do you determine when to either go all-in or to realize, “Staying in here is delusional. What I’d hoped was going to happen isn’t, and I better cut my losses and go in another direction.”
 
Dan Sullivan: My experience, if you use the play that you’re now heading towards Broadway with, and think about the judgments that you’ve had to make even doing the first script to get it started. And now you’re re-casting for the first big time where it’s a major theater city and it’s in a major theater, you’re 10 steps above where you were when you had the first group of actors just reading the script. So you’re about 10 paces up. And all the different decisions that had to be made and judgment calls that you had to make, that if you go back 25 years, you wouldn’t have had the skill to do any of that.
 
Jeffrey Madoff: I think that that’s... I’m old enough that 25 years ago I was in my late forties, so I hope I had some facility for it, but I don’t think I would be able-
 
Dan Sullivan: Well, you wouldn’t have the reputation and the connections-
 
Jeffrey Madoff: That’s right.
 
Dan Sullivan: ... that you attracted, quite apart from the cast onstage, the skill level backstage.
 
Jeffrey Madoff: That’s right.
 
Dan Sullivan: How many top, top-notch Tony Award winners, producers, choreographers, music directors, lighting directors and everything, and then the financial people who know how to put together a play and raise funds. The 25 years between—counting back 25 years before you actually started the project, the day you decided, “I’m going to move with this project.”
 
Jeffrey Madoff: Very early forties.
 
Dan Sullivan: You had developed a lot of sensors-
 
Jeffrey Madoff: Yes.
 
Dan Sullivan: ... through trial-and-error in different kinds of projects with different kinds of people. And you accumulate this feel for things.
 
Jeffrey Madoff: You’re right. And it is an interesting way of putting it, because those sensors that you’re talking about, looking back, you can kind of create a narrative to how things happened. As you’re going through it, you really can’t.
 
Dan Sullivan: Yeah.
 
Jeffrey Madoff: You don’t know yet. And so, I think there’s an ability to recognize opportunity, to know how to go after it if it presents itself, and I think that that’s something that comes with age. And I think that you’re very right.
 
But in dealing with entrepreneurs, have you ever dealt with people that you think, “There’s a ceiling to what they’re doing and it’s not very high, and they’ve gone all in and they better think of some kind of pivot if they hope to survive.” What is it that you see when that’s the case?
 
Dan Sullivan: Well, first of all, both of us have knowledge beyond our industry, whatever our industry is. Both of us are very, very interested in outside, “What are the politics of the day? What’s the economic situation of the day?” So it isn’t just experience within your particular line of work that you have available to you, but you’re getting a feel for, “Is the tide in or is the tide out?”, just generally.
 
I would say that the people who are the most consistently successful have broad knowledge of many, many different things, not just the uniqueness, not just the specialization in their particular trade. Okay? And as a result of that, you realize that what you’re doing is just, it’s important to you, but it’s not important to most of the world. I don’t care what business you’re in, that there’s 8 billion humans who get up every day and get about trying to live. And there’s a collective effect of all these people going. And you’re an insect on the windshield in terms of how important what you’re doing.
 
So I think you talk about the age, I think there’s a depersonalization that goes on. We’re both in our seventies, but I really notice that it’s nobody else’s responsibility or business that I should be successful. It’s strictly my business. I might as well enjoy the activity. And I think probably with both of us, we just like what we’re doing day by day in a way that we didn’t 25 years ago. I’m not trying to get somewhere. I’m where I want to be. I just want to expand who I get to do it with.
 
Jeffrey Madoff: Thank you for listening to part one of the podcast. Join us for part two coming up.