The Future Is All Guesses And Bets

Jeffrey Madoff: This is Jeffrey Madoff and welcome to our podcast called Anything And Everything with my partner, Dan Sullivan.
 
Dan Sullivan: Do you have a big treat on your hands? Because in the next hour, we're going to talk about anything and everything. We don't know what's going to happen. This is all guesses and bets what we're doing. And I thought I was a big guesser and better, but I've met my match.
 
Jeffrey Madoff: Well, we can guess about that. You know, the guesses and bets phrase, which I love, you know, it relates so well to entrepreneurism because all new businesses are guesses and bets. And I'm wondering, do you think that when you start talking about things like, how do you know there's a market for it? What kind of price threshold is there for it? Do these kinds of questions help us make better decisions or does it just make us feel more confident about the decisions that we're making since they're inherently uncertain anyhow?
 
Dan Sullivan: Well, first of all, I think guessing and betting is a capability. If there's a difference between entrepreneurs and other people, I would say that entrepreneurs generally do a lot more guessing and betting than, for example, just to compare, someone who's employed, you know, has a job, and they had a guess and a bet that this would be a good job for them. But I think once the employment takes part, that they're in the job, they have a sense that now I don't have to guess and bet anymore about my paycheck. And I think entrepreneurs, by the very nature of the activity, that the income has to be constantly created. There's no guarantee that it's going to continue. It may not continue in the way it's been continuing. I may have to find out some new approaches. I may have to explore new opportunities. And I think entrepreneurs, they have a makeup that makes them want that activity more than something that seems like a guarantee. And I would say that entrepreneurs are more comfortable with uncertain times than other people who are employed, just by the nature that they approach uncertainty from this standpoint. In uncertainty is opportunity, and people who are employed, in uncertainty there's danger. I think there's a difference between opportunity and danger, and how people approach uncertainty.
 
Jeffrey Madoff: Well, I think if you're looking for a job, that distinction is greater because you think, you know, I'd like to have a steady paycheck.
 
Dan Sullivan: Yep.
 
Jeffrey Madoff: And so your guess and bet is, which is much more of a guess and bet than what we grew up with, that you'll have that job. But even those companies such as Amazon have shown us that Facebook too, or Meta, that, you know, it's not stable anyplace.
 
Dan Sullivan: Yeah I was just reading Washington Post, they fired 300 people. My sense is that we've entered into a period, now I don't know if this is unique in human history, I've done a lot of reading about the crossover between the agricultural economy and the industrial economy, beginning of the 20th century, late 19th century, early 20th century, and there was certainly an enormous amount of uncertainty in the marketplace. So I don't know the answer to that. But I have much more certainty of cash flow at this point in my entrepreneurial career than I did right when I started coaching. You know, that was month to month. Was the money gonna come in? And now, at the beginning of the year, we kind of know where 50 to 60% of the cash flow is gonna come from.
 
Jeffrey Madoff: Yeah. And you've also been in business for 45 years?
 
Dan Sullivan: I've been in business for 52 years, but the company as it exists, this is our 37th year. So there's a certain predictability about how things are going to go about. All of our fees come up front and there's no refunds. So we can tell by the way that things are coming in and we work towards this. You want to have predictability.
 
Jeffrey Madoff: Yeah, now, and I think things are predictable until they're not. You know, I think that's true with the stock market. It's true with the weather. You know, it's true with a lot of aspects of life that they may seem predictable or more regular, if you will, which also relates to bowel movements, and both can have a lot of shit. I had to go around the block for that metaphor. I don't know if it was worth the trip. But I think that it's interesting because I think we fool ourselves into thinking that we're making the right decision when we don't really know, but we're making the best decision we can make with the knowledge that we have.
 
Dan Sullivan: Yeah, I think we can know that. Yeah, and it all depends on what your risk tolerance is, you know. The project that you've been on now, you know, since you got the idea that the life of Lloyd Price would make a great musical, if you combined his life story with the music that was recorded, it would make a great potential Broadway musical. And it strikes me that it's been constant guesses and bets right from day one.
 
Jeffrey Madoff: Oh, absolutely. Absolutely. And the only thing I can say about that is I knew that much. You know, I didn't necessarily know what the guess or bet would be, you know, whether it was guessing that, you know, doing the enhancement deal with People's Light Theatre, who were great partners to start, but no one could have ever anticipated that COVID was going to happen and the disruption that caused and the year and a half delay, not just for us, but for people just involved in live performance. That was a huge thing. How could you prepare for that?
 
Dan Sullivan: I have a question for you. You did this in your late sixties, early seventies, so this all happened. If you had compared yourself backwards to who you were at late thirties and early forties, do you think that you were more knowledgeable with having 30 years’ experience between your late thirties and your late sixties, that you had seen this before in many other types of projects, and therefore you could be more at ease with what you were actually doing? Because you never seemed particularly freaked out by the uncertainty of how this was going to go.
 
Jeffrey Madoff: No, the uncertainty has never freaked me out. I mean, have there been times of concern? Yeah. I mean, we did our concerts in October of ‘25 and ticket sales, even though I had been told that characteristics since COVID actually is that people buy much closer to the event—I kept getting told that, and it was a week before, and we hadn't even cracked 30% sales, but then we ended up selling out two shows. I wasn't freaking out. I think I've been through enough that freaking out doesn't do anything for you, and I try to keep as clear a head as I can, so if I have to make a decision, I mean, they're making a decision based on not only my knowledge, but, you know, the group that I put together that has the combined experience of success and longevity and sustainability in the business. And I truly believe, and this is something that hit me years ago, the big things in life, which are your health, the health of loved ones, and assuming that you can at least take care of a certain level of living and lifestyle that you're comfortable with.
 
You know, to me, the really big questions are those things that tie in more to the most important relationships in my life. You know, the concern for good health, you know, and taking care of yourself. You know, our friend Joe, when he made that switch and concentrate a lot more on addictions. I think he wanted to help other people based on what he had gone through and maybe helping them shortcut the issues they're dealing with. And I think that if you have a lot of experience, whether it's in something like that, in working with entrepreneurs, I mean, with the play, what I knew about COVID was, well, we're all affected by this, you know, in terms of in theater and so on. We're all affected by this. So it's not like all of a sudden a bad decision I made gave everybody else an advantage or whatever. It was, everybody gets affected by that thing. So I don't tend to get freaked out, but I do go for solutions. And I do seek what I believe to be wise counsel in making those decisions.
 
And I think that we're all going to screw up sometimes. you know, that's going to happen. And the question is, how do you recover from those problems or mistakes or obstacles that you couldn't or didn't anticipate? So I do hope, just to finish answering your question, that 30 years later, you know, when you go back in time and then ask me about those 30 years, I would hope that I've gained not just knowledge, but wisdom that informs the decision-making and the processes that I go through. And that would be a sorry statement if I thought I knew everything at 40 and now at 77. You know, I know everything, so I haven't really questioned myself for the last 30 years. Although I certainly know people that do believe that about, or at least try to convince others.
 
Dan Sullivan: Yeah, the thing that I've really been interested in was, I mean, there's two types of uncertainty. There's uncertainty because that which you thought was predictable has turned out not to be predictable. But there's another thing, you're actually doing new things that you've never done before, and there's uncertainty attached to that. And of the two, I prefer the second.
 
Jeffrey Madoff: Well, I prefer the second also.
 
Dan Sullivan: But if you stop doing new things, then you're left with the first.
 
Jeffrey Madoff: Well, that's right. That's right. You know, I think that not knowing, being open to new experience, I guess what I'm coming to is that I think that businesses have more in common than they do different. So the leap to theater from doing the kind of productions that I did, there's a lot of similarities. And being aware of those similarities or being able to connect those dots so I can recognize the patterns of what's going on, there's an awful lot of overlap. So nothing seems so foreign. I can see antecedent similarities to it through the things that I've been doing over the last 45 years in production. Does that make sense?
 
Dan Sullivan: Oh yeah, totally. We're both theatrical in our approach to our businesses. We have been from the beginning.
 
Jeffrey Madoff: Mm-hmm, true.
 
Dan Sullivan: Yeah, I mean, I think the reason why we wrote the book is because we've been living the book for the last 50 years.
 
Jeffrey Madoff: Well, truth be told, the real reason that we're doing the book is because when you and I were doing a podcast about a year ago or so, and you asked me about how I approach hiring, and I gave the answer, and you went, whoa, there's a book here. And fortunately, you were right. You know, that's great. And I think that the wisdom to make that call, it wasn't just an exclamation. I think that what informed that was the books that you've done before, the market that you know that's out there for entrepreneurs, all of those kinds of things. And so the wisdom, which I think knowledge without wisdom is information. But wisdom allows you to make the best decisions. So I think that your recognition—call it pattern recognition. You had your Who Not How, or Gap And The Gain. And so when you heard casting not hiring, there was a resonance there. And when we talked about the experiences of entrepreneurs and not building a staff and building an ensemble, not interviewing, but auditioning, how collaborations can be fruitful. taking the theatrical model rather than the business mode—in all of these things, I think that both of us were able to build on that initial idea based on the wisdom that we've gained in the past few decades.
 
Dan Sullivan: Yeah, and I think the thing about it, at the same time, we were doing that when a whole new technology was being introduced into the world. One of its impacts is to eliminate the usefulness of jobs. A job is kind of like an algorithm. You know, your job is to do this, and there's a method to it, and in this situation, you do this and this and this and this. There's a predictable pattern or system or process that's involved in every job, and it just happens the new technology is very good at automating those type of processes. And therefore, the way someone can make themselves safer in the marketplace is that they're using their intelligence, they're using their experience to spot new things that need value created, new solutions are needed. And that's like improv. And if you don't like doing that, well, then there's going to be a lot of discomfort, there's going to be a lot of risk, and there's probably going to be a lot of bad experience, because the technology now eliminates—I mean, the technologies of a century ago eliminated physical labor, now we're eliminating mental labor.
 
Jeffrey Madoff: And I think that there are significant problems with that. And I think that AI is a fantastic tool, which as we've spoken about in the past, you've got to vet the information, you can't assume it's all correct and all of that sort of thing. But before we started recording and you were talking about AI isn't being forced on us, people are adopting it really fast. There's two pushbacks I have on that. One is without the foundational aspect of the internet, that's something that, you know, facilitated the opportunity for even a more rapid spread of ideas. So I think that without the internet, this would have been one idea among many and whether or not people heard of it in a timely fashion or adopted in a timely fashion or whatever. But now everybody's kind of plugged into that switchboard anyhow. And then whether you're using Gmail or whether you're searching on Google and you get Gemini to do the search, there's a lot of things that the blanks are already filled in. So you can respond to an email, respond to this or that without thinking. And I think that can be dangerous.
 
And I think that, you know, one of the people that I interviewed, Victoria, her idea of human-in-the-loop technology, and she's in financial services, she said, you know, because 95% accurate's not accurate enough. And that creates problems. We have to be more accurate than that. And I think that human in the loop to moderate, to keep the eye on things that are new, that haven't been identified before as such, you're not gonna get good information about that through the nature of what AI does. And what it does really well, and it'll do more things really well, but at this stage of its evolution, there are opportunities that are created. Most of the opportunities that I see being created are people trying to sell other people on their knowledge of AI and how your business can't live without it. And so here's what you should be doing. And I think that that's, I don't know that there's, I'm sure there has been intelligent discussion, both pros and cons of the potentials of this. And I'm talking about without the hyperbolic, this is the best thing, utopian, or this is the worst thing, destruction aspect. But, you know, how do you use that tool in the best way to net the best results?
 
Dan Sullivan: Well, one thing that is apparent to me is that no technology is self-coaching.
 
Jeffrey Madoff: Explain what you mean by that.
 
Dan Sullivan: Well, no technology explains to you how to use it. And the reason is because it was created by people who are already very skillful at it, and they've lost touch with people who aren't skillful. You know, I was thinking of a previous technology that would sort of resonate with what people are going through right now. And it's a technology, but it's more a capability. And that is literacy. Literacy. I'm reading this whole series of historic novels that take place in the British Navy in the early 1800s. And it's very, very clear that your upward ability to move in society was a function, could you read and write? Well, the printing press had been created 400 years before that, you know, a good three and a half centuries. So even over a space of about four centuries, literacy had not really caught on yet. It was just starting to catch on that you really had to learn how to read and write, you know. Well, I think if you use AI, you know, you're really going to have to learn how to use this if you expect to go upward. And we're in the very, very early stages of that process.
 
Jeffrey Madoff: Yeah, and one of the things that I do when I use AI, I mean, I really dislike the fact that I'm getting these, you know, pre-digested responses to emails that I could just, you know, click it and send it. And I think that like anything, if you stop exercising a certain muscle, it atrophies. And I think that there's a lot of potential for atrophy. And I think that it's important to engage with a subject in a way that allows discovery and growth rather than just, oh, this makes it easier. And then you click without thinking, which it seems to me a lot of people do.
 
Dan Sullivan: But it seems to me … are you doing that?
 
Jeffrey Madoff: No.
 
Dan Sullivan: Okay, well, you're the one human you can have an influence on.
 
Jeffrey Madoff: Oh, that's right. I actually had an influence on my cousin, who forwarded me these things, and I sent him the sightings and the verifications about what we were talking about, because he had just forwarded an email, basically because he agreed with it. But it wasn't about vetting anything. It was about, you know, oh, this supports my point of view and you just send it without checking whether or not it's even true. But one of the ways I use AI is I will actually ask it, if you were creating a prompt to ask you this question, how would you phrase the question?
 
Dan Sullivan: Yeah, I do that too. And that can net some interesting answers. But they're contextual. It's not content-based, it's context-based. I mean, AI will be as smart as you require it to be. In other words, if you just want content, it'll just give you content. But if you ask a question that gets a response that you're really dealing with an intelligent partner, AI will do that. It'll be smart or stupid as you want it. It's probably as smart or as stupid as the user. You're simply getting a mimicry back at the level of intelligence that you're operating at. If you're asking really multi-dimensional contextual questions, it will respond to you because it has all the patterns. You know, it has access to all patterns of thought that are in print, you know, that it can actually do that.
 
So my sense is, I had an experience about three or four weeks ago, and I think I told you about this, but I have a thinking tool that I created, which is called the Fast Filter, and you state the best result, and I'm doing it in the second person personal, so I'm talking to a you, who's the reader. I set up my chapters this way. And then the best result is an individual who's really smart, who's really ambitious, who's really, really growing. And I'm saying in my thinky-do, you're doing this and this, and here's five ways to prove that you're actually doing this, okay? And then to counter it, I have backup writers and I have editors. I create a negative statement where the reader is really stupid, has no ambition whatsoever, and just abruptly, Perplexity, the platform that I use, said, we cannot respond to this request because we don't want to be making statements that people are stupid or lack ambition and everything. We don't think that's good. And I said, well, over the last two years, you've done it about 300 times, and you didn't have any problem with it. And it came back and says, no, but we have new safety rules. And this violates our new safety rules. Okay. I said, okay. It's your platform. You can, you know, they're your rules.
 
So anyway, next Fast Filter, I do the best. Then I get to the worst. And I say, now, I want you to read the best paragraph, the best result paragraph that I've read here. And I want you now to create a paragraph, same style, same voice, same structure, with just the opposite meaning and message, then the best result. Just like that. Okay. So it was, and then it started saying, do you want me to make this message even more cynical than you've voiced it? And I said, yes, yes, make it more cynical. And then it says, do you want it to sound more depressing and demoralizing? And I said, yes, I would like that.
 
Jeffrey Madoff: So what happened?
 
Dan Sullivan: I got exactly the same result as I was getting before. But I wasn't the one that used the word depressing. I wasn't the person. So they said, we can ask you a question. Okay? And we're not responding to your negative request. So there's something in the legality of what they're doing. My sense is that they're facing lawsuits, and they don't want to be on the hook that they encouraged someone or they went along with someone's writing negative messages. You know, it's a very nuanced thing that's actually happening. But it was interesting, just my understanding of how this technology is working, that they had found a way of answering my request, but not in the way that I had originally presented it.
 
Jeffrey Madoff: Yeah, or they're hoping to avoid losses.
 
Dan Sullivan: Yeah, I think we're very close to where there's going to be real legal, you're going to start seeing lawsuits about AI. And I think it's going to become a major political issue. I think that the party that grabs a hold of this and is going to have a long run with it in the same way that the Democrats were the ones who grasped the entire social impact of industrialization and the Republican stint. Starting in the 1890s, it was the Democratic Party in the United States that, you know, really, really got in touch with what was happening to industrial workers and the Republican stint.
 
Jeffrey Madoff: Yeah, and I think that when you have something that can disseminate information so quickly and appear to answer questions so accurately, it's incumbent on the user, or to use that phrase, you know, if it's being done by a business or whatever, the human in the loop, that I think it would be a good idea not to censure speech, but to know how to vet information.
 
Dan Sullivan: Yeah. But you bring up the case, people are just accepting the answer. Well, I know a lot of people who do that person to person. They just accept the information without any experience.
 
Jeffrey Madoff: Well, sure.
 
Dan Sullivan: Yeah. So my sense is it's not AI that's doing that. It's the user of AI is being undiscriminating. They're not discriminating. They're not discerning.
 
Jeffrey Madoff: Well, this is a tool that allows them to do that on a much larger scale. It's one thing if you're just talking to your neighbor. It's quite another thing when you're addressing tens of thousands, if not millions of people with something. So there's a difference in impact. And I just think that knowing how to, it would really be interesting, this just occurred to me, to hear the decisions about the atom bomb. We know certain things that have been paraphrased and so on, but the moral questions that arose from do we drop the bomb or not, how many potential lives do we save by doing that as opposed to prolonging the war, all these kinds of things. And what I'm saying is that on the big questions, I'm not talking about if you're writing a new marketing copy, but in the big questions, there needs to be questions and there needs to be discussion about what that is. And I think that anytime there has been something really major, I don't know what there is now to kind of put the brakes on certain things until we know more than we know. I don't think there are. And as you said, I mean, unscrupulous people are gonna game any system you set up.
 
Dan Sullivan: Well, and I'm discriminating. People are going to buy anything that unscrupulous people sell.
 
Jeffrey Madoff: Yeah, that's right.
 
Dan Sullivan: Yeah. But that's been true since forever.
 
Jeffrey Madoff: Oh, absolutely. Yeah, absolutely. But, you know, I totally agree with that. But I think that as more and more people have access to these tools, raising the questions and having informed discussion about them is an important thing.
 
Dan Sullivan: Yeah, we don't know how they're using them. I mean, there's no way of knowing how people are using. Some people use them to organize their hobbies. Some people use …
 
Jeffrey Madoff: Oh, yeah.
 
Dan Sullivan: No, I mean, the getting information, my sense is the same biases that condition someone's doing research before, I think the same biases are still there if they're just using a faster tool.
 
Jeffrey Madoff: I agree. And the question is, how do we recognize …
 
Dan Sullivan: Well, who is we?
 
Jeffrey Madoff: How does the public, how do users, how do consumers do that?
 
Dan Sullivan: Individually and differently with each person.
 
Jeffrey Madoff: And are we better off if people are making decisions that have been questioned and pushed back as opposed to just accepting whatever you get as truth because you got it? Because it's on the internet or whatever.
 
Dan Sullivan: So I think people is an abstraction here. I think each individual is probably responding quite differently, you know, because they're relating it to different experiences and all experiences are subjective and unique. The main problem here is that it's so fast.
 
Jeffrey Madoff: And why is that the problem?
 
Dan Sullivan: Well, in the same way that movies were a much more powerful medium of communication than still photographs. I remember Matthew Brady, who was the great Civil War photographer, after the battle of, I think it was the Battle of Vicksburg, which was just in Pennsylvania. He had his photographers out, and they were photographing the aftermath with the bodies laying across the field in ditches. And he put on a great exhibition in New York City of just showing these photographs. And the lineups were around the block for the better part of six months, because people had just never seen an actual depiction of what war was like afterwards and everything like that. And this had an enormous impact on people's thinking about war. But World War I, which was the first real videoed movie photography thing, was in spite of the censorship, you know, I mean, these films, but they got through to the public, you know, two years later, three years later, and they would see the damage, but they were watching movies. They weren't looking at individual photographs, and the impact, it was much greater, and it was the speed. It's a lot easier to fool people with a movie than it is to fool them with photographs, because of the speed factor. It seems like it's real. You could have a research project where people go out for six months and they bring back an amount of research and it's presented, it's got a point of view, and a search that takes five seconds and it brings the same amount of information to this. What seems more magical is the speed with which it happens.
 
Jeffrey Madoff: No, I agree with that. I think that individuals aggregate. Depending on, of course, what one's purpose is and how you're using things, whether this is just something that affects an individual, they purchase something maybe they don't need. Or they purchase something that's great. But I'm saying the more people learn how to distinguish between the two, the better off we are. That's what I'm saying. And will we ever escape that kind of drifting? No. I think that's been here forever and it will be, but if there are ways that people, there are ways that people can be better informed in the decisions, whatever it's about, whether you're buying a car or whether you're voting for a political party or you're doing research. We have tools, as you said, that do it faster than ever before, but it isn't just a dialogue between two people in certain aspects of the usages we're talking about. So I think I always go back to critical thinking in context.
 
Dan Sullivan: How is this different from newspapers? How is what's happening now any different from the newspaper trade, which was at its greatest 100 years ago, much more influential 100 years ago than they are today? How is it any different than what was going on there?
 
Jeffrey Madoff: How do you mean what was different?
 
Dan Sullivan: Well, it doesn't seem to me that the danger is greater with AI than it was with newspapers. People still aggregated, and they talked about things. And in some cases, they were being misinformed, and it spread through the entire population. And in other cases, it was accurate. It doesn't seem to me that it's a difference of kind. It may be a difference of degree, but it's not a difference of kind. It's always been there since we had mass communication.
 
Jeffrey Madoff: Yeah, and I think going back to your point before, which is correct, speed. You can get a lot more in front of a lot more people a lot faster. And so I think that that's the thing, and things happen so quickly, and a lot of people don't necessarily know how to discriminate between the two, which has also always been the case. I'm not saying that it hasn't been the case, and I'm not saying that people being fooled or misinformed or whatever is a new phenomenon. It's just that we've been able to speed up that process tremendously as a result.
 
Dan Sullivan: You know, what hasn't speeded up at all is people can only think about one thing at a time and it takes time. So our ability to process information hasn't improved at all. Okay, it's constant, because our brain can only think one thought at a time. Now, they can get overwhelmed by the tsunami of information that's coming in, but then they just cut off thinking altogether. People just say, I think it's all bullshit, and then they go there. So I'm just not seeing, you know, is the danger any different today than it was at a previous time? I don't know, and I don't know how you actually compare it.
 
Jeffrey Madoff: First of all, I think it's an interesting question. How do you vet information? I think most people look for the simplest solution, which is that one message that they can then send to several thousand people at once. And, you know, just things get out there quickly, much more quickly than they did before. The intent of the individual, I think we both agree, is no different. Everybody wants, whether they're buying something that's going to increase their income or make them more attractive to the opposite sex or the same sex, all of those things, the selling and marketing fundamentally have not changed. I think what has changed is how quickly information can get out there and be disseminated. And so I just think it's important. If you're going to pass it to anybody aside from yourself, I believe it's the importance of vetting something, not accepting things out of hand and just passing them on. That's all. When I say that's all, that's not small.
 
Dan Sullivan: No, I'm just saying that I think in your case, in my case, all we can do is make sure that we do that.
 
Jeffrey Madoff: Yeah, and if everybody did that …
 
Dan Sullivan: No, no, but there is no everybody. There's just you and me. Because I don't know who the we is. Is there a group of you that gets together that talks about this? I mean, I don't know what the control factor here is that you could ever change it.
 
Jeffrey Madoff: I don't know either. I think, again, that's why I think that asking those questions can make a difference.
 
Dan Sullivan: Well, I think it makes a difference for you.
 
Jeffrey Madoff: Of course.
 
Dan Sullivan: It doesn't make a difference for any abstract we. I just don't know who the we are here. So far, there's only been two of us on the podcast since we started.
 
Jeffrey Madoff: Well, that was the criteria we set up at the beginning, because we wanted two forces that were aligned in terms of, you know, and it's interesting, we're aligned on the importance of informed debate, of context, of critical thinking, of those kinds of things. Doesn't mean we're going to reach the same conclusion.
 
Dan Sullivan: Well, it also doesn't mean that I'm trying to influence someone else by having the discussion. You know, I'm more and more improving my own ability just to think things through in such a way that I've got a fairly accurate read on what's going to happen next.
 
Jeffrey Madoff: I think a by-product of being informed is that, hopefully we're making decisions that are better decisions as a result of the information that we consume and all of that. So none of these are simple questions in terms of we do this. It's not even a question of, well, this is about if you and I were just having private correspondence, and hopefully somebody's listening to this besides you and I. I think that these are not new questions. There's just new technology to bring other conditions.
 
Dan Sullivan: I think they are simple questions. It's just that the answer is hard.
 
Jeffrey Madoff: Right. That's what I'm saying.
 
Dan Sullivan: The answer is difficult. The question is pretty straightforward.
 
Jeffrey Madoff: Right. It's finding the answer. Agreed.
 
Dan Sullivan: I think part of the reason is that the further away you get just from the person who is asking the questions, the more difficult the answer gets, because I think, it isn't like there's one good way of doing it and then everybody else is doing the bad way of doing it. I think people are using the information they need to live their life. They're acquiring the knowledge they need to live their life. And I don't think there's any broad sweeping movement among people that takes them too much further than leading their life. What kind of life do they want to lead?
 
Jeffrey Madoff: That also leads to a lot of big questions. And again, the questions are the easy part. The difficult part is, what's the answer? What do I do with that information? Does it even make a difference?
 
Dan Sullivan: Well, for example, our last three podcasts before this one were on happiness. And the topic came up that there are polls that for the last 50 years, people have not gotten any happier. And I say, well, who did the polling? And what were the questions and how did they frame it? What were the questions and who did they ask? You know, who did they ask? So that in itself, 50-year polling is saying maybe the person wanted to prove that over the last 50 years, people haven't gotten any happier. So they just selectively pick the people who agree with that particular thesis.
 
Jeffrey Madoff: Yeah, again, I don't disagree with that. But what you're bringing to bear on that, which I think is the good part, was critical thinking. You're asking a question of, how did you arrive at this conclusion? What's the criteria for making the decision that you reached? Well, who was talked to? Yeah, I agree with all that.
 
Dan Sullivan: Yeah. And one of the things that's interesting along those lines is they're discovering now, it's applied to doctors in medicine, it's applied to lawyers in the areas of law, that, for example, they find that automated diagnosis machines in medicine do a better job of getting to what's actually going on with the patient than a live doctor asking the questions. You know, for example, I've seen demonstrations of this where, first of all, doctors are authority figures. Lawyers are authority figures. Okay. So the doctor asks the questions and the person gives an answer and the doctor says, phew, wow. The patient will just immediately change all their answers just because of the doctor's reaction. So they find that automated polling, for example, where you just have to hit numbers on your phone, are much more accurate than a live interviewer phoning a person, who are they in favor of, and everything like that. So the whole point, you know, it's Heisenberg, the German philosopher, it was called the Heisenberg Principle, and he says the experimenter influences the experiment. And I think that's true. So all polls are necessarily almost subjective.
 
Jeffrey Madoff: Well, as we know, I mean, you can only talk about the accuracy afterwards. And oftentimes that ends up being a platform for excuses as to why these two polling groups reached diametrically opposed answers and were supposedly sampling similar groups of people.
 
Dan Sullivan: Yeah I'm just saying that one of the great uncertainties about the discussion of anything that we're dealing with subjects that are largely subjective, like there really isn't a lot of objective knowledge out there.
 
Jeffrey Madoff: I mean, that gets into an interesting area, too. And I want to go back to the question you asked me and ask you, which is, and I'll frame it more in the world of entrepreneurs. Can a 30-year-old entrepreneur be as wise as a 70-year-old, or is there something about living through decades and having more experience that makes that, what does the 70-year-old bring to it that a 30-year-old doesn't have, or vice versa?
 
Dan Sullivan: Well, I think that if wisdom was a matter of experience, I would say probably not, that the 30-year-old isn't as wise. But I think that there are people who are born wise, and I think there are people who aren't wise who are 70 years old who practice not being wise for 70 years. Yeah, I said, you know, stupid old people really practiced.
 
Jeffrey Madoff: And decades to practice. That's right.
 
Dan Sullivan: Yeah. They doubled down. So it's hard to tell. I would say how I related to entrepreneurs, I don't use the word wisdom, but I do use the word common sense, you know, that they have a better sense that they know what they know, but they know there's a lot that they don't know. And so they're open to that possibility. I just may not know what's going on here. And I think that's an attitude which is probably they're young and it gets better as they get older. I know I'm way, way practically smarter at almost 82 than I was at 32.
 
Jeffrey Madoff: Yeah yeah yeah. It’s interesting. Is it smarter or you see things differently?
 
Dan Sullivan: Well, you've practiced in hundreds of situations and you have a sense of how far you can go with any venture before it's not worth investing in anymore. What increases with really, really smart entrepreneurs is the ability to say no to things they would have said yes to earlier. For example, I make up my mind about people much quicker today than I did 50 years ago. I get involved with far fewer projects because the projects just don't take me where I thought I would know. You're asking about entrepreneurs because I think entrepreneurs, at least the entrepreneurs in The Strategic Coach Program, are learning at work for a much longer period than most people who aren't entrepreneurs, which makes sense, because they're taking on new projects, new relationships, new opportunities on a continual basis. I just think they have vastly more practical experience than people who, you know, went to college, came out, got a good job, were in a situation, didn't own the company, you know, they were simply paid employees, their salary went on, they knew the industry they were in. I think that if you compared the learning experience, the trial-and-error experience to the entrepreneur, it could be a hundred times greater than a corporate executive.
 
Jeffrey Madoff: Well, what I wonder about is that there are entrepreneurs that are brilliant at certain strategies for business, but that's sometimes, and not infrequently, coupled to the need to be right, even when the problem would be best solved or approached with collaboration or accepting ambiguity or something like that. And I think in some cases, being smart can become a liability. Because you can also think about all the things that could go wrong, which will cause you not to do it. And there is some truth to that phrase, ignorance is bliss. And do you see that with any of the entrepreneurs that you coach, or just that you've been exposed to over the years, whether they've been a part of Strategic Coach or not, that need to be right? Oftentimes gets in the way of progress, but it may not get in the way of making money. You know, it's just how they work with people. And I think also, just to tag on response to what you were saying, I am saying no to more because I only want to do what I want to do and, you know, can do that. And I think that's good, but I'm also aware that I am older and my time is more valuable than it ever was. Does that play into your decision on that too?
 
Dan Sullivan: Yeah, I think there's a lot of different factors and they would resist learning new things. And if they're resisting learning new things, they'll drop out of the Program. So they won't be in the Program for very long. We're constantly asking them to look back at their experience and what did they gain from their experience. And if you put this experience together with that experience, do you see anything new? And they do. And if they don't have that experience, they don't renew. They just don't renew in the Program. So I think the majority of my experience is people of 20, 25, 30 years who are just constantly learning. And constant learning requires that you realize, I wasn't looking at this properly, and now I'm looking at it in a better way. If you have that flexibility of thinking, then probably their main point isn't being right. Their whole point is being continually successful at adapting. It brings up Darwin's survival of the fittest. Well, they're not fittest. They're adaptable. When circumstances change, they change, you know. I think they're much more open to seeing unpredictable change as a positive thing than a negative thing.
 
Jeffrey Madoff: You know, I remember when most of my work was film-based. And I loved working with film because video allowed you to be a lot sloppier, because videotape was much less expensive than film. They didn't have the same processing costs and all of that kind of thing. However, there were many of the cinematographers, when this was really beginning to take root, you know, shooting with video cameras rather than film cameras, was really starting to take root in the probably late ‘80s into the ‘90s and beyond. And now, you know, Spielberg's one of the few or Paul Thomas Anderson, some of these filmmakers who really want to use film. And what's interesting is that film is a much more challenging medium to use well. And video was started as an engineer's medium.
 
But to get to the point I wanted to make is that there were a lot of cinematographers I knew that did not want to learn video. They had their film cameras. Part of their package and part of the revenue stream was that you hired them and rented their equipment, which was fine equipment, but they were using film when others wanted to use video. And they got frustrated and even angry at the fact that the principle technology was in a state of flux and going to be changing. And it was clear that you couldn't unring that bell. And so the smart thing to do would be adapt and learn how to use video and use the talents you have. Like all the video people I ever hired had film backgrounds. That's not going to be the case anymore because the years and the technology have progressed so much, but going back to then, because they knew lighting better. And so the cinematographers knew lighting so much better than video.
 
But I said to those cinematographers, well, I'm not going to learn video, it's bullshit. I said, you know, that's temporary. The technology is going to get better and better and better. And if you don't use it, unless you're in that very rarefied air, you're going to not get the job. So you got to decide, it's not just a question of a particular job. It's a question of your career. Do you want to keep doing what you're doing because you're aging out of it in terms of your ideas?
 
Dan Sullivan: Yeah. They weren't adaptable.
 
Jeffrey Madoff: That's right. Stubbornly. So, you know, so then you just find all the things wrong with it.
 
Dan Sullivan: Well, then if you take a look at what else is happening in that person's life, that's making them unadaptable in this part of their life.
 
Jeffrey Madoff: Like what?
 
Dan Sullivan: You know, their personal life. Their health may not be as good, and they don't have the energy to learn something new.
 
Jeffrey Madoff: Or the desire.
 
Dan Sullivan: Or the desire. Maybe they've already achieved what they want to achieve, and they've got enough stored away that they can take a risk at not learning.
 
Jeffrey Madoff: True, that's true.
 
Dan Sullivan: Yeah, from an outside standpoint, we definitely can spot an adaptable person from a not adaptable person.
 
Jeffrey Madoff: Yeah, and it's interesting how that manifests.
 
Dan Sullivan: I mean, you see it very definitely in putting a theater production, actors who are adaptable to a change in approach from one day to the next. You did it this way yesterday, but we have to do it this way. And the ones who can adapt to that 24-hour change stay employed and the ones who don't aren't employed.
 
Jeffrey Madoff: You're right. And one of the things that happens during auditions is Sheldon Epps, the director, will give somebody direct, they do a scene, I'll have him read it, and then he will give them direction on, you know, he said, I'd like you to try it this way. And they'll give him some other direction. Many people just do the same thing again. And so one of the things that you want to find out, whether you're in theater or entrepreneurs, that's right. And this person take direction and they actually act on that direction. So you hope that you are weeding out those people before you get to the booking them stage, because it's only going to create ongoing problems. It's interesting in those worlds that have changed so much and how that medium has changed. But those who adapted have done well because they had a big record to start with in terms of their resume and the work they've done and so on, which was great. But instead of applying that to what they did, they felt this negated everything they had done. And for whatever reasons, including the ones you mentioned, they aren't interested in changing.
 
Dan Sullivan: Yeah. You know, I think that people do adapt. I would say the vast majority of people who do adapt do it under pressure, do it under, they're being coerced by the circumstances to change. But there's other people who just have a natural, they've trained themselves to be adaptable. So how have you trained yourself to be adaptable? In other words, if you think back, as of today you've got, probably 71 years of conscious experience. I'm discounting the first six. I don't, you know, generally speaking before six, we don't have too much of a handle on things, but you have 71 years. What have you worked on to make yourself adaptable?
 
Jeffrey Madoff: Talking to people who are using that new technology, asking them what they feel the benefits are, what the pitfalls of it are. Do they think this is going to be around or do they think that this is a novelty that a lot of people are talking about? And also talking to people who are using it and finding out what are the resistance points they have and why. Because even back then it was clear to me, and I'm going back now 35 years, it's clear to me, it was only a matter of time before video production usurped film production almost totally.
 
Jeffrey Madoff: And it didn't matter even which did I like the best. This is what was going on.
 
Dan Sullivan: The same thing happened in sound recording.
 
Jeffrey Madoff: Yeah, sound recording, that's correct. I mean, it was almost seemed like overnight the record stores, and I used to go into Tower Records and Disco Matt all the time because I was a big consumer of music. I love music. And it went down to, from having these albums with great artwork and the liner notes and all of that, to a link. I think that my adaptability was, I realized I was along the spectrum of things happening. And so I would seek to understand those things to try to make the best decision. And I always felt like the more knowledge I have, the better off I am anyhow. You know, so I think learning is inherently a good thing, but it also allowed me to make those changes. You know, when I bought my first editing system, it was linear editing, not non-linear, which is, you know, what Avid or Adobe Premiere or those kinds of things.
 
Well, it's all software now. Very few people are cutting film anymore. The guy that maintained my equipment was the person that installed all of the new, what were called Avids. Avids were the, at the time, the most innovative nonlinear editing software. And he said, I'm going to show you how the software works. And he said, I know you well enough. Your problem with adjusting to this will be nonexistent. You'll love it because you're going to be able to edit sound and pictures like you edit words in word processing. And it's not good enough yet. The resolution, you can't deliver on it. It's only for editing. And then some months later or so, he said they just released AR35 or whatever it was, Avid Resolution AR35, which was equal to three quarter inch tape. He said you can deliver on this for your clients. And now you should invest in it. And during that time, I had learned a lot about it, and it was great to work for, and much faster, and there were so many things you didn't have to worry about that were amazing. So I've always been open to those things, as opposed to looking at the problems of having to learn it. I looked at it more as an opportunity that I can learn more, come at things differently, and that opened the door for me to do different kinds of work, too.
 
Dan Sullivan: You know, what I'm seeing from your description of the cinematographers who couldn't adapt, and I've got a feeling that I haven't really talked about this before, but they had a social reality because there was a long period where cameras were kind of the same, you know, and I'm sure that movie cameras were kind of the same. Once you learned the skill, you didn't have to do too much learning to do it. You had to master your craft. But then the craft was agreed on, then you were set for the rest of your life because you have the craft. The craft is your judgment, but the craft is also your use of the technology.
 
Jeffrey Madoff: That's right.
 
Dan Sullivan: And it's almost like a guild. You started off as an apprentice, and then you went to journeyman, and then you became a master. And then you got to have a social life, an exclusive social life with all the other cinematographers and you would get together. And it wouldn't be so much about filming or it wouldn't be so much about projects. It would be, we're really special people. We're really special people. We get to hang out together and we swap stories and everything like that. But we're at the top, we're making good money. Our names are on lists, we're on short lists and we get pulled into projects. And then an entirely new technology comes along, which not only puts their craft in a question mark, it puts their technology, but their entire lifestyle of being the masters. So I think it's the real threat to identity. It's not just a threat to what they know, it's a threat to who they think they are.
 
Jeffrey Madoff: Yeah, and you know, the thing is, you saved up and you bought, you know, an ARRI 35mm or one of the other top cameras. And you are correct. The technology is essentially the same. The motors were quieter, but it was basically about putting film through at 24 frames a second, you know, and that's what it was. So your income was also impacted because the video cameras were really expensive at that time. I mean, they're still expensive, but part of their revenue stream was that they would rent their equipment package along with them. So it was redefining all of that. But those who I knew who were great, that adapted, did video better than the ones who didn't have a film background because they knew light. They knew the crew set up, and video cameras wouldn't look like they looked if they weren't trying to make cinematographers who were experienced comfortable. Like, ARRI still makes arguably the best video camera for shooting feature films, and it mimics the film cameras, kind of like how the QWERTY keyboard took over as the input device.
 
So, you know, it's really interesting. And all the greatest cinematographers I worked with, and I worked with amazing cinematographers, Academy Award winners like Vilmos Zsigmond,who, they knew their craft so well, and the majority of their craft transferred. And those other things they learned really quickly anyhow because they were just smart and good at what they did and knew what they had to do to achieve the look that they wanted. But it is really interesting is what do you do when it seems like everything you've been doing for 30 years has now been wiped out and you got to start again.
 
Dan Sullivan: Yeah. I often think it's an identity problem of who they think they are, that once they achieved a certain identity, they thought that was predicted that that identity would never change.
 
Jeffrey Madoff: I think that's true.
 
Dan Sullivan: Yeah. And there's just a point where people stop adapting. Too much work, too hard, don't have the ability. I mean, there's a point where they really stop. And there is a deterioration of the brain. I mean, we know that the brain volume goes down. And there's now ways of increasing brain volume. But there's a point where your brain just isn't what it was, you know.
 
Jeffrey Madoff: These guys, by the way, weren't necessarily old. I mean, I'm talking about people who have been doing it for 20 years, but they were in their mid-40s. So they had a long life ahead of them in that field. But I think the disruption to what they were doing, that they didn't own that equipment, that it just shuffled things around for them. I mean, they didn't rent their own equipment when they were, you know, making a feature film. Vilmos did McCabe & Mrs. Miller, Close Encounters of the Third Kind, Deliverance, he's a phenomenal cinematographer. But for him, you know, he could walk in, it was so cool, the first time I met him, we were on set doing a commercial, and he walks in, he's like looking around, he goes, okay, we need a quarter stop net on this, wasn't even using a light meter.
 
Dan Sullivan: He had a total field.
 
Jeffrey Madoff: That's right. Yeah. Yeah. And it was just cool to behold because he wasn't showing off.
 
Dan Sullivan: No, he's just been doing it that long. He was that good.
 
Jeffrey Madoff: Yeah. Yeah. Which was a pleasure to work with. It was cool.
 
Dan Sullivan: Yeah. He just had many more dimensions to his craft than other people did. The one example that's used just how great great people can get was the filming of the jazz album, Kind of Blue. You'll love that. Miles Davis. And it happened in New York City. It happened on two days. And he brought all these famous, the very top musicians. And they started off and he had some sketches on a sheet of paper. And he says, I do this and then Cannonball, you come in here. And he had them all. And he says, I'll just start in there and I'll just nod to whoever goes next. And these were all different instruments. And he did it, and they did a whole day. They went out and did whatever jazz musicians do at night. And then they came back the next day, and he got finished, and they went through. He says, yeah, we got 11 cuts here. He says, I think this is good. And that was it. But each of them had 40 years of doing riffing, you know, adjusting to different situations. And they had all played with each other over those years. So they just had this vast knowledge. And it's the number one selling jazz album of all time.
 
Jeffrey Madoff: Well, it's fabulous. Lloyd's wife, Jackie, dated Miles Davis before she dated Lloyd. And she has very good friends with Miles. And my favorite band, I've told you about Dan Flaremo, big band. He's so brilliant. He did this whole thing about Kind of Blue, mashing it up with the Who. So he starts off with the Who music, which is, “I Can See for Miles,” that then segues into “Kind of Blue.” And it's just such a wonderful ride. It's just fantastic. Yeah, I think that Miles Davis is a good example because he did jazz and then he was one of the first major jazz musicians to do fusion. And because he was such a creative artist, there were some that, of course, felt like he was somehow a traitor because he was doing that, just like people thought Bob Dylan was a traitor when he played electric guitar. And it's so interesting, the people that are fans, you would think would be open to the person that they liked innovating and doing things. But, you know, they get very stuck in their expectation.
 
Dan Sullivan: Well, when you're too much of a fan, you become a fanatic.
 
Jeffrey Madoff: All true fan addict. That's right.
 
Dan Sullivan: If you keep it at three letters, it's okay. But it's an interesting thing. And my sense is that 10 years from now, how people adapted and used AI will be seen as very different from how it's being predicted right now.
 
Jeffrey Madoff: Well, I'm sure. I mean, because that's almost always the case.
 
Dan Sullivan: Yeah. And for example, the top six AI companies, you know, NVIDIA is one of them, and then Google's lost $1.4 trillion in market valuation last week on the stock market. You know, they're appraised valuations. And the reason is the article says what they thought was going to happen quickly isn't either going to happen at all or it's not happening as fast as they bet. So, you know, like everything else, like everything else. But a lot of good will come out of it. You know, it's like, remember the subprime real estate market? You know, ‘08, ‘09. And everybody says, what a scam. But three million actual houses got built during that period in record time. And they're all houses that people need today. You know, so whenever you have this boom situation and anything, a lot of really neat stuff gets created whose value is not seen until afterwards. Yeah, sometimes long afterwards.
 
Jeffrey Madoff: Yeah, I think that that is more the rule than the exception. I think that the rule is that things take longer, are more expensive, and, you know, the payoff comes further down the road than people hoped. But everybody focuses on how they can become a billionaire at 32. And, you know, chances are really high that's not gonna happen.
 
Dan Sullivan: Yeah, or who we think are going to be the winners and losers, it turns out differently.
 
Jeffrey Madoff: Yes.
 
Dan Sullivan: It just turns out differently. You know, the online shopping, well, it turns out the people who had great bricks and mortar businesses actually weathered the storm with online. I mean, you know, Walmart has done very, very good with online shopping, and they were the bricks and mortar. Yeah. So the big thing is, it's all guesses and bets. It doesn't matter what comes along, it's all guesses and bets.
 
Jeffrey Madoff: Yeah, I mean, the brick and mortar that was their appearance, in a way, was Sears. Sears was like, Sears has everything. That was their slogan. But they didn't adapt, and basically they don't exist anymore. And then I think it was just last week that Walmart hit a trillion-dollar valuation. So it is all guesses and bets. And you say that's our takeaway for today?
 
Dan Sullivan: I think that's it, yeah. It all comes back to guessing. Anything is a guess and a bet and everything is a guess and a bet.
 
Jeffrey Madoff: So all is a guess and a bet.
 
Dan Sullivan: Yeah. I loved your film story. I think that's really great. I'm reading a story now in the British Navy. They've gone from sailing ship and they're bringing in steamships. The skill required to sail a great sailing ship is 20 times the skill needed to sail a steamship. Because the steamship doesn't care what the wind is, steamship doesn't care what the waves are, steamship doesn't care about anything. And so the skills you need on a steamship are basically just make sure you got enough coal. You had all these incredible skills, people who can work with the sails, and it was just a huge drop in skill level with the new technology. And they could go much further. They couldn't go as fast at the beginning, where the top sailing ship could do 14 knots an hour. The top steamship could go about seven knots, but they could do it hour after hour for the next three weeks and the sailing ship couldn't. But it's really, really interesting. And they're having these discussions, you know, how sad it is that we're losing all this skill. And, you know, we used to have honor in our profession and everything else. What's the honor of being able to put coal into a furnace? But you could just see that that technology has that de-skilling quality. And I'm sure AI is doing that right now.
 
Jeffrey Madoff: Yeah. And it's an interesting lens to view it through. Thanks for joining us today on our show, Anything And Everything. If you enjoyed it, please share it with a friend. For more about me and my work, visit acreativecareer.com and madoffproductions.com. To learn more about Dan and Strategic Coach, visit strategiccoach.com.