The Art of a Great Question with Cal Fussman [From the Archive]

[00:00:00] [SPEAKER_07] Every day as a small business owner feels like solving a puzzle. One moment you're cruising along and the next there's a shipping snag that has you scrambling. But here's a surprise you will like. With Progressive, small business owners save 13% on their commercial auto insurance when they pay in full. So go ahead, surprise yourself. Get a quote in as little as 8 minutes at ProgressiveCommercial.com. Progressive Casualty Insurance Company and Affiliates. Discounts not available in all states or situations.

[00:00:29] [SPEAKER_02] This isn't your average business podcast and he's not your average host. This is the James Altucher Show.

[00:00:45] [SPEAKER_06] Presenting the archive. Classic episodes that remain timeless. The raw, unfiltered conversations from the early days in which people shared their failures and showed us exactly how they rebuilt everything from the ground up.

[00:00:58] [SPEAKER_02] Do you think this ability to super connect with people and indulge in the unknown, we're losing this a little bit? And your premise is that questions and questioning, opening up someone's life almost as if you're like cracking the shell of a peanut. This is a skill that's no longer around as much.

[00:01:19] [SPEAKER_04] When you think about it, there was no Google back then. Now, just about any question you have, you could put it into Google or Quora and you're going to get an answer.

[00:01:32] [SPEAKER_04] So, if you're looking at the laws of supply and demand, the supply of answers is filled. We got answers up the kazoo. But how many great questions do we have? How many people who ask great questions do we have? There's much more demand for that.

[00:01:53] [SPEAKER_02] I want to get to the idea that questioning not only is a way of connection, but it's like this superpower. Questioning and figuring out how to dig in and open people up provides you experiences and surprises and expands your horizons. That is the superpower.

[00:02:16] [SPEAKER_02] I am so excited to have Cal Fussman, writer at large at Esquire on the podcast. And Cal, I first heard him on Tim Ferriss's podcast a couple times and I read about you in Tools of Titans. And I've been reading your stuff ever since, listening to your podcast. You've written some New York Times bestselling books. You have your column in Esquire is what I've learned. How many people have you interviewed overall?

[00:02:41] [SPEAKER_04] Overall? Overall. I never calculated that, but for people about, I guess you'd say iconic stature, probably 400 to 500.

[00:02:53] [SPEAKER_02] I'm going to have to ask you what iconic stature means. Like, I feel like you're dissing some people there. Well, no, people who everybody knows. Like, okay, so you've interviewed Gorbachev, Kobe Bryant. Of course, Muhammad Ali was a classic story that you wrote, a front page story for Esquire that you wrote. Al Pacino, Serena Williams, Larry King. Larry King, you have breakfast with every day when you're in LA. You also have a great podcast, Changing Your Questions Changes Your Life. Or no, Big Questions.

[00:03:22] [SPEAKER_02] But you say, Changing Your Questions Changes Your Life. And so, but reading your story, before I get into all the people you've interviewed and had an interview and amazing things you've learned and experienced, I remember reading, you were in Brazil traveling around the world when you were younger and you met your wife, who's still your wife. I don't know how many years later, decades later, you met your wife while you were both standing in the aisle of a bus.

[00:03:50] [SPEAKER_04] So here's what happened. So I was traveling around the world for roughly 10 years. Why? Okay, we'll take it back further. So what happened is I came to New York to be a magazine writer in about 1980.

[00:04:13] [SPEAKER_04] And there was this startup magazine called Inside Sports, no longer exists, that just came out to compete with Sports Illustrated when Sports Illustrated was in its heyday. And the guy who was in charge of this, his name was John Walsh, later went to ESPN and he was the guy who created SportsCenter.

[00:04:37] [SPEAKER_04] So he brought in an amazing group of people to get in on this magazine. And I was 22 and I basically left my job in St. Louis, packed what little I had in a little Honda, drove to New York. What was your job in St. Louis?

[00:05:01] [SPEAKER_04] I was working at the St. Louis Post-Dispatch, covering the, being the second guy on the Cardinals baseball team. I was very young. And so the plan there was for me to understand all the sports in the city and then eventually become the columnist.

[00:05:23] [SPEAKER_04] But I kind of understood very quickly that if I did, if I did that, if I stayed in St. Louis even a few more years, basically my life was fixed. I would know everything that was going to happen the rest of my life because I'd be writing a column in that newspaper every day.

[00:05:50] [SPEAKER_04] And so I got in my car and I drove to New York and Inside Sports was started by Newsweek magazine, which was a big weekly magazine back then. And I remember I got in the elevator to go up and meet John Walsh the first time. And it was a Friday at about four o'clock.

[00:06:17] [SPEAKER_04] And on this elevator, there was a lift that's stacked with cases of beer. And the elevator got off on the floor of Inside Sports. The cases of beer preceded me and went into the office of Inside Sports. And it was just a big party. And I knew like this. You got it right there. This is where I got to be.

[00:06:43] [SPEAKER_04] And then, not that day, but Hunter Thompson would come by and you'd drink with him over at the Cowboy Bar. David Halberstam, Pulitzer Prize winning writer, would come by. And so to be a young writer in this environment was the best.

[00:07:03] [SPEAKER_02] And let me ask you about that. And I'm sorry I go on tangents. I really apologize. No, it's fine.

[00:07:07] [SPEAKER_04] I'll go with you.

[00:07:08] [SPEAKER_02] But because I do, I am really curious about what that first thing you said to this Brazilian woman on a bus was. But it seems like what you just described is fascinating. So they're creating a sports magazine. But what they're doing is aggregating these great writers who technically are not sports writers. Like Hunter S. Thompson was not known. He wrote a lot about sports, but he was not a sports writer. He was this guy.

[00:07:35] [SPEAKER_02] He's this inventor, supposedly, of gonzo journalism. Right. And David Halberstam, his best book or his most well-known book is the best and the brightest about the cabinet members around the Vietnam War and the Kennedy days. So you bring in these writers and say sports. And do you think that's an interesting way to kind of build a magazine?

[00:07:56] [SPEAKER_04] That was the whole structure of it. Obviously, there were a few people who were sports freaks that were at the foundation of the magazine. But there was another writer named Pete Dexter, a novelist. Yeah. Just real talents. Pete Dexter, was he ever the editor of the Daily News? He was a columnist in Philadelphia. You're thinking of Pete Hamill. Oh, okay. Right. Yeah. Also a very talented writer.

[00:08:26] [SPEAKER_04] Pete Dexter later became a screenwriter and novelist. But these people were really talented. So when you went to the bar after the day's work, you really were pushing yourself to get the most out of yourself.

[00:08:48] [SPEAKER_02] Sounds like you're pushing yourself to drink a lot of alcohol, too. That was, too. There's beer all day at the office. And then afterwards, when you go to the bar.

[00:08:54] [SPEAKER_04] And there was a guy named Pete Axelhelm, who was a columnist at Newsweek and also a member of this cast. Great writer. And you would just be around these amazingly creative people. And you couldn't. You woke up every day wondering who you're going to meet. What great thing is going to happen?

[00:09:23] [SPEAKER_04] And I have friends, a writer named Gary Smith, who later went on to win many national magazine awards for Sports Illustrated. I met him during that time. And it was just a wonderful time for growth. Like, you're 22 and the whole city is yours. That's what it felt like.

[00:09:43] [SPEAKER_04] And the problem was, like a lot of startups, this was an artistic success, but not so commercially. And Newsweek pulled the plug after a couple of years. And it was devastating because this wasn't a job. This was a passion. And I was in on the ground floor.

[00:10:10] [SPEAKER_04] So I could walk in the office and say, hey, Cal, go to Pittsburgh, interview the Steelers. They're going for their fifth Super Bowl ring. And all of a sudden, it wasn't there anymore. And I'm looking around, and I really don't know what to do. And so, obviously, the first thing that comes to mind is, oh, I need a job. But where? Because that's going to be a job.

[00:10:39] [SPEAKER_04] This was a passion. This was life. So- Did you cry? I don't remember crying. And you know why? There was a final scene. This was like right out of a movie where a venture capitalist bought the magazine from Newsweek and ran it into the ground. And all of a sudden, there were rumors. There's no more money.

[00:11:10] [SPEAKER_04] And so people had just gotten their checks. So everybody ran over to the Chase Manhattan Bank to cash their checks. And the bank freaked out because they weren't sure that there was money in the account to pay these checks. And you had like 50, 60 people online.

[00:11:35] [SPEAKER_04] And I remember the New York Post came and was snapping photos through the windows because the bank actually locked the doors. And they went and put down drapes or whatever to try and conceal what was going on. And ultimately, after hours, somehow funding came through whatever and everybody got their money.

[00:12:04] [SPEAKER_04] And it ended up at the bar with everybody kind of laughing. So it was, you know what? There was a moment where I remember being in a bar with John Walsh. And he brought up the song, Kill All the Brave Horses. And that always made me feel really sad because that magazine was a brave horse. And it went down. So what?

[00:12:34] [SPEAKER_04] And I want to ride more brave horses. What am I going to do? So I say, you know what? I always, like, I wanted to travel. I met a woman in France or from France. And she was telling me that you could go to her town or nearby and pick grapes. So I had this, like, romantic vision in my head. And, like, go to Montpassier to pick grapes.

[00:13:02] [SPEAKER_04] And, of course, I was reading, like, Hemingway and a lot of the authors, John Dos Passos, back in the 30s and the 40s. And Europe was where they went and cut their teeth. So I said, you know, why don't I just take a little time and go to Europe and then try and figure this out?

[00:13:26] [SPEAKER_04] So I went to Europe with this friend that I mentioned, Gary Smith. And he had, it was just coming out of a bad marriage. I say bad marriage. It's just like a lot of marriages. It's not good or bad. It just wasn't the right fit.

[00:13:48] [SPEAKER_04] And so he was in this stage where he just wanted to go out and experience the world because he kind of felt all cooped in for years. And so what happened is he went out first. And we agreed to meet in Munich for Oktoberfest. But in the meantime, he went over to Italy.

[00:14:13] [SPEAKER_04] And for whatever reason, he went into a train station and bought a ticket without even knowing what the destination was. Just got on the bus and he got off. And he just started walking. And a guy pulled over and asked him if he wanted a ride. And the guy was a little crazy, but brought him into this town of Castle Viscardo.

[00:14:43] [SPEAKER_04] And within, it was a very small town, within a half an hour, like everybody in the town wanted to come meet Gary. And he spent three or four days there. And they put him up. Is that because he was just new, like a new thing? Yeah, for somebody from abroad or America to come into a place where you don't normally see an American, it's like a new show is in town.

[00:15:13] [SPEAKER_04] And so everybody in town knew Gary's name. And later, Gary came and met me at Munich. And he was telling me about what had happened to him. And he actually took me back to this place. And as soon as I walked in, it was, Calvin! And we stayed there. We picked grapes. We did some work. But it wasn't really work because you'd go to do a job.

[00:15:41] [SPEAKER_04] And after an hour, let's drink some wine. Another hour. Time for lunch. It was really joyous. And I just fell in love with this idea of waking up in the morning and not knowing what was going to happen. I had a taste of it at Inside Sports.

[00:16:10] [SPEAKER_04] But this was 24-7.

[00:16:14] [SPEAKER_02] Do you think you can achieve that sort of feeling or do you try to still achieve that sort of feeling in daily life? Because now you have more of a routine with family and work and so on. And as you get older, of course, we get, I don't want to say addicted to routine, but we get used to the routine that we're in. And it's a little harder to kind of just travel around without the responsibilities and so on. But do you think there's a way to still kind of create that feeling of every morning I wake up? And what a surprise.

[00:16:43] [SPEAKER_02] The sunlight's coming through the window. And what will happen next? That is an awesome question.

[00:16:52] [SPEAKER_04] It's an awesome question because it's something to ponder with the intent of, wow, could you do that? Now, in New York, 100%. In LA, 100%. In St. Louis, Missouri, I'm not sure. Maybe. You're really down on St. Louis. No, I love St. Louis. That was the point.

[00:17:21] [SPEAKER_04] I loved it so much that I was scared. If I don't leave now, I'll never leave because I did love it. And it was one of those situations where you know, okay, if I'm writing a column in the daily newspaper, there's basically that's, if you're a newspaper writer, that's as high as it's going to get in St. Louis.

[00:17:50] [SPEAKER_04] And you're going to just do that five times a week or four times a week. And that is going to be your life. So could you do that and still wake up every day not knowing what was going to happen? Much, much harder there, I think. New York, I think you can go a whole life.

[00:18:15] [SPEAKER_04] And I actually did this at the end of a long trip I'll tell you about. But I came back to New York after 10 years of traveling without knowing what was going to happen when I got up. And I started walking the streets of New York. I had a map and I would just take a magic marker and draw it through the street as I walked through it. And I just literally just walking, not north to south.

[00:18:45] [SPEAKER_04] Every day I would wake up and just go to a different part of the city and walk.

[00:18:49] [SPEAKER_02] And this is not necessarily when you would be what is considered young. Because if you had spent a couple of years at Inside Sports and then spent 10 years traveling, you're probably 35 or 36 at this point.

[00:19:03] [SPEAKER_04] That's correct. I was about, let me try and get the exact date. I think I was about 30, maybe 34 or 35. Yeah. When I was walking the streets. And that was right before I ultimately married the woman that I met on the bus. So what happens is I start traveling around.

[00:19:31] [SPEAKER_04] And my friend, this is to show you like where our minds were at. And I'm sure you're at the hunger for new experiences. Because we're also connecting how the more new experiences we have, the more we can write about. I'm certain it's not much different in comedy. You get more experiences. You have more places to go and have fun with.

[00:19:57] [SPEAKER_03] Sure.

[00:19:58] [SPEAKER_04] So I just became addicted to this feeling of getting up in the morning and not knowing who I was going to meet. Not knowing where I was going to stay. And don't forget, there's no cell phones back then. You, I would, I would get on a bus.

[00:20:26] [SPEAKER_04] And after a while, I became very good at this. Where I would be, buy a ticket without knowing where it was going. I'd get up the steps and start walking down the aisles. Looking for an empty seat. And as I'm walking down the aisle, I know this is a crucially important decision.

[00:20:56] [SPEAKER_04] Because I got to find somebody just by reading their face or the way they're sitting. I got to know, are they interesting? Will they trust me? Can I trust them? And then I have to make a decision after seeing all those faces. Okay, which seat am I going to choose? Because I have very little money.

[00:21:22] [SPEAKER_04] And so I couldn't keep this trip going by spending night after night in a hotel. I basically had to sit down next to somebody and start a conversation. And often in a different language. Or when I say a different language, they're speaking a different language. I'm maybe speaking English or fragments of this new language. And we're communicating with our hands, do charades.

[00:21:51] [SPEAKER_04] And by the end of the trip, I needed that person to invite me home. Because other than that, I had no place to stay. And so what happened is this took me to places I couldn't have imagined. And then when I got there, the same thing that happened to my friend Gary in Italy would happen. They immediately would start calling their friends and their relatives to come and meet me. And a party would break out.

[00:22:21] [SPEAKER_04] And the party might go a day. It might go two days. People who are at the party may say, come to my house. And then have their friends come to meet me. And this is how I got passed around the world.

[00:22:39] [SPEAKER_02] Do you think this is a skill set that this ability to kind of almost super connect? So there's two things that are happening there. One is you're indulging almost in trying to see how little you could know about how your experience is going to unfold. So you don't know where you're going to go, where you're going to sleep, how you're going to make money, who you're going to talk to, what friends you'll make, and so on.

[00:23:07] [SPEAKER_02] So you're almost trying on purpose to know as little as possible. Whether you realize it or not, it's almost like you said you were addicted to it. This is not knowledge. Now we have so much knowledge, it's hard to have that feeling or to replicate that feeling. The other thing is now if I want the equivalent of walking down the bus trying to find a place to live is I'll go on Airbnb and make a connection there and connect with someone. Oh, I don't have a lot of money. I'll just do it as cheaply as possible. You can go as cheap, as expensive as possible.

[00:23:36] [SPEAKER_02] So, or Craigslist or whatever.

[00:23:40] [SPEAKER_04] And not only that, but if you walk down the aisle on the bus, maybe the person sitting next to the empty seats got earbuds in.

[00:23:51] [SPEAKER_02] Yeah. Right.

[00:23:52] [SPEAKER_04] It wasn't like that.

[00:23:53] [SPEAKER_02] Right. People don't need to connect with you now or they don't want to because they're already connecting to some inter-world.

[00:24:03] [SPEAKER_04] Or an outer world that they want to connect with.

[00:24:06] [SPEAKER_02] Yeah.

[00:24:06] [SPEAKER_04] I mean, maybe they're listening to your podcast.

[00:24:09] [SPEAKER_02] Right.

[00:24:09] [SPEAKER_04] And they don't want to be interrupted.

[00:24:11] [SPEAKER_02] I'm preventing you from living. So, so, so like these are skills. Like, so like I remember reading, you know, or listening on the Tim Ferriss podcast, you would, you would try to find the grandma. Essentially, you can ask what's the best way to make great goulash. And that would build the whole story and everything. But do you think this ability to kind of super connect with people and indulge in the unknown, we're losing this a little bit.

[00:24:38] [SPEAKER_02] And your kind of premise is that questions and questioning and opening up someone's life, almost as if you're like cracking the shell of a peanut. This is a skill that's no longer around as much. It's still always going to be around, but it's not around as much.

[00:24:56] [SPEAKER_04] I agree with that. And I also think that what happened is interviewing went to television and it stopped becoming interviewing. What we think is an interview now is often a confrontation because what makes news is some kind of back and forth, some kind of crossfire.

[00:25:28] [SPEAKER_04] Whereas when I'm sitting down with somebody, I'm not trying to play gotcha with them. I'm not trying to prove my point over theirs. I'm, I want to listen to what they have to say. You're not going to get that on Fox or MSNBC anymore.

[00:25:50] [SPEAKER_02] Well, not only that, they're, they're only in three minute clips. So like, so Steve, the podcast producer here, his last job was TV. He was producer of Good Morning New York, which is the top rated morning show in New York. And Steve, what's, what's the difference?

[00:26:07] [SPEAKER_01] Yeah, it was like three, it was like three minutes and it didn't give you a lot of time to get in depth, you know, with the person over there.

[00:26:13] [SPEAKER_02] That's every interview on TV now. It's just three minutes, no depth.

[00:26:16] [SPEAKER_01] And I think you two were speaking about it too. Like James doesn't necessarily need notes and cards because he doesn't have to feel like, oh, I only have three minutes or four minutes. I have to make sure Cal is plugging this or getting that.

[00:26:28] [SPEAKER_04] Oh, well that, yeah.

[00:26:29] [SPEAKER_01] It's more expansive, you know.

[00:26:31] [SPEAKER_04] You know, it's an excellent point because what's happening now is you, if you've got the producer putting something on a teleprompter or, or, or a card saying you've got to hit these points and you've got the guest or the subject coming onto the interview. You prepped by a public relations expert, get these talking points across.

[00:26:57] [SPEAKER_04] Basically there's no real free flow back and forth. Everything has been scripted.

[00:27:04] [SPEAKER_01] Yeah. It's not a conversation and it's transactional.

[00:27:07] [SPEAKER_02] So, so, so, so again, like the art of questioning has been almost replaced by, you know, the, the, the sort of glut of media and attention gathering material that's all over the internet. So, so, so, so, and, and, and again, that, that loss of human connection that that that's in the internet, not, not blaming the internet. It's just this evolution of, of communication.

[00:27:33] [SPEAKER_02] And, uh, you know, the art of questioning also is this way of, uh, of really opening up and connecting directly to people instead of over an online means.

[00:27:42] [SPEAKER_04] And on, on, on top of that, what's happened is because people can now measure, uh, how many times like a certain person is being clicked upon. Uh, the producers are then noticing, okay, this person gets 4 million clicks. This person gets 200 clicks.

[00:28:07] [SPEAKER_04] Uh, the person with 200 clicks, that's an interesting story, but we're going to have better business if we go to the person that gets 4 million clicks. Even if there's no story there, let's just follow him. Let's just follow her. And maybe something will happen, but it doesn't even need to happen because as long as a person says something, 4 million people will be attracted to it just because they will follow.

[00:28:36] [SPEAKER_04] So everything that, that celebrity does. And so what happens is we stop looking so much for the interesting story and are just following the people that everybody knows and will click on. And so that's even, it provides even less of an opening, uh, for good questions.

[00:29:04] [SPEAKER_02] Right. Like it, it becomes your, it used to, you know, your self-worth becomes the number of followers you, you have. Like people kind of, because, because we always sort of put ourselves in a hierarchy just by being primates that has become the hierarchy. People tend to put themselves in or media tends to put people in or whatever.

[00:29:26] [SPEAKER_04] That's the top of the food chain.

[00:29:28] [SPEAKER_02] Right. As opposed to even things like, I don't know, there's no, there's no other metric of quality really. Like quality has gone down the tubes and replay and is replaced by likes. Uh, but I, but I want to get to the idea that questioning not only is a way of connection, but it's like this superpower.

[00:29:48] [SPEAKER_02] Like questioning and, and, and kind of figuring out how to, how to dig in, open people up that provides you housing and income and experiences and surprises and expands your horizons. Like that, that is the superpower. That's like your mutant superpower.

[00:30:07] [SPEAKER_04] Yeah. I, I think it is.

[00:30:09] [SPEAKER_02] And if you were, if this was the Justice League, you're like question man.

[00:30:15] [SPEAKER_04] Yeah. I, but you know, the, the problem with that is I'd have a costume with a question mark on it.

[00:30:21] [SPEAKER_03] And you look like the Riddler.

[00:30:22] [SPEAKER_04] I was already taken by the Riddler. It's, it's, it's an interesting thing because the more that I think about it, the more that I see like what questions can do for people. You, you can show your intelligence by asking a question.

[00:30:42] [SPEAKER_04] I, I remember when I was a freshman in college and I, I was on a path to be a sports writer and I went to the University of Missouri, which has a big journalism program.

[00:30:57] [SPEAKER_04] It was so competitive that there were in this little town of, oh, they, they couldn't have had more than 50,000 people, but there was a town newspaper. There was a journalism school newspaper and there were two university newspapers.

[00:31:24] [SPEAKER_04] And, and so there was so much, so many people were going there to be journalists. It was so much competition that everybody wanted to be the person who wrote about the University of Missouri football team because it was the biggest, most eyeballs are on that.

[00:31:47] [SPEAKER_04] And when I went as a freshman, I realized, you know, I was going to have to wait like years in order for the seniors to graduate and then the juniors to move on and graduate. And by the time I was a senior, then I could get in the locker room and practice the craft. And I just, I was ready to get in the game.

[00:32:09] [SPEAKER_04] And so I went with the older reporters in the same car where they drove to these away games and just sat in the stands. And I watched the games. It's because I want to be close to it.

[00:32:29] [SPEAKER_04] And around the fourth or fifth game, there was a big upset that Missouri had pulled off on the team from Nebraska, which had a national championship winning coach and a great, powerful tradition. And I just felt compelled. I had to get in the locker room. There were questions I had to ask.

[00:32:54] [SPEAKER_04] And so I looked down and I saw there was a photographer from the school newspaper I was working at. And he had a press pass dangling around his neck. And I thought, well, he's not going to go in the locker room. He's done taking pictures. What if I got his pass? Would that let me in the locker room? Then I could ask my questions. So I got down to the field. He said, sure, I'm not going to use the pass. Put it around my neck. I got in the locker room.

[00:33:23] [SPEAKER_04] And I can remember looking around and there were all these people that I wanted to be. They had the job that I wanted. And they're asking the coach questions. And all of a sudden, out of nowhere, I had this one question and I just asked it. And there was silence.

[00:33:51] [SPEAKER_04] And the coach, like you could see his eyes go up in the air. He was really thinking about the answer. And then he started to answer. And I saw everybody. This was the days before tape recorders. Everybody had their pads out. They were busily writing his answer. And I knew in that moment, two things that happened. One, the coach had respected the question and given a good answer to it.

[00:34:21] [SPEAKER_04] And two, I looked around and thought, okay, now I'm one of you guys. And from that moment on, I had a very different confidence.

[00:34:31] [SPEAKER_02] Right. And what you showed there is that the art of asking a good question creates a career rather than necessarily knowing all the facts. So people sort of feel like, oh, if I know all the facts, then I have a career. But actually the art of knowing what questions, like science is all about, people don't realize science is not about knowing the secrets of the universe. Science is about asking the right questions about the universe and then testing those questions.

[00:34:59] [SPEAKER_02] And so it's really the questions motivate the career rather than having all the information, which changes constantly and is wrong constantly and so on.

[00:35:08] [SPEAKER_04] And I agree 100%. And when you think about it, there was no Google back then. Now, just about any question you have, you could put it into Google or Quora and you're going to get an answer. So if you're looking at the laws of supply and demand, the supply of answers is like filled. We got answers up the kazoo.

[00:35:36] [SPEAKER_04] But how many great questions do we have? How many people who ask great questions do we have? There's much more demand for that, I think.

[00:35:50] [SPEAKER_02] Take a quick break. If you like this episode, I'd really, really appreciate it. It means so much to me. Please share it with your friends and subscribe to the podcast. Email me at altitra at gmail.com and tell me why you subscribed. Thanks. Football is back and I actually care again. Not in a, I need a second income way. In a, this makes Sunday more interesting way.

[00:36:20] [SPEAKER_02] PrizePix is doing their best offer yet. New users who sign up get $150 in lineups if you win your first $5 lineup. That's it. Win the first $5 lineup, you get $150 in lineups. And they're available nationwide now. What you on this football season? I'm on Kenneth Walker. He shared the backfield in Seattle, then was MVP in the big game, and Seattle let him walk to Kansas City. I took more on his rush yards. He's playing like a guy who wants them to remember that decision. He's my guy.

[00:36:50] [SPEAKER_02] He's on PrizePix. They're going crazy in stack September. New promo every day. Guaranteed picks every Sunday, plus profit boosts and daily discounts. You pick two to six players, more or less on projections like pass yards, rush yards, fantasy score, same app, any sport. Simple. Injury reboot if a guy goes out in the first half and doesn't come back. Live box scores. Copy popular picks in one tap.

[00:37:15] [SPEAKER_02] Download the app today and use code Altature to get $150 instantly in lineups if you win your first $5 lineup. PrizePix. Run your game.

[00:37:39] [SPEAKER_08] You're listening to this podcast, so I know you've got a curious mind. Here's a helpful fact you might not know yet. Drivers who switch and save with Progressive save over $900 on average. Pop over to Progressive.com, answer some questions, and you'll get a quick quote with discounts that are easy to come by. In fact, 99% of their auto customers earn at least one discount. Visit Progressive.com and see if you can enjoy a little cash back. Progressive Casualty Insurance Company and Affiliates.

[00:38:07] [SPEAKER_08] National average 12-month savings of $946 by new customers surveyed who saved with Progressive between June 2024 and May 2025. Potential savings will vary.

[00:38:18] [SPEAKER_07] For a small business owner, every day is full of surprises. Some great, some not so great. Like when a client cancels their order at the last minute. But here's a surprise you will like. Progressive provides small business owners with 30 customizable coverage options to help keep their business going strong. So go ahead, surprise yourself. Get a quote in as little as eight minutes at ProgressiveCommercial.com. Progressive Casualty Insurance Company and Affiliates and third-party insurers. Coverage is not available in all states or for all vehicles and coverage selections.

[00:38:48] [SPEAKER_02] I read that when you're, and again, I just want to emphasize, you know, you're one of the great interviewers of all time. You've, in every field, you know, we mentioned a couple of names already. Gorbachev, Serena Williams, Kobe Bryant, Al Pacino, Robert De Niro. You've interviewed people from every walk of life and built a career out of it.

[00:39:14] [SPEAKER_02] And, you know, again, this has kind of created a whole career for you, this ability to ask these questions. But before an interview, I read, you sometimes write down 100 questions you might ask, but then you throw it all out before the interview. Right.

[00:39:30] [SPEAKER_04] Because what happened was I was doing an interview with F. Lee Bailey. The lawyer. The lawyer. And I went into that interview, it was Esquire had started this column called What I've Learned, which is wisdom in the words of extraordinary people. And I had a sense that I was going to be good at this.

[00:39:56] [SPEAKER_04] And so I wrote out my questions for F. Lee Bailey and put them all in a little book. And I had this little book in front of me. And I learned a lot in that hour and a half. And one of the things that happened was he looked at the book of questions. And I could just see. Disdain.

[00:40:24] [SPEAKER_04] There was, I don't know if disdain was exactly the word, because it was sort of an arc between disappointment and disdain. Like he wanted something better. And there was a little disdain. And, you know, that's the best we're going to have here. And I'm working through this question.

[00:40:54] [SPEAKER_04] Finally, he told me this story. He said, you know, when I'm in court, I never use a piece of paper to ask witness questions. Often what I do is I'll say, James, tell me, did you order? I'm just approximating this.

[00:41:23] [SPEAKER_04] Did you order a vanilla milkshake on March the 3rd of 2004 when you were on 84th Street in New York? Now, of course, you're going to look back at him and think, what does this milkshake have to do with the case? This case is about a bank. And you're thinking, did I order the milkshake? I don't.

[00:41:53] [SPEAKER_04] I don't. And then you say, no, I don't know. I don't know. And then Bailey would go back to his desk and take out a piece of paper and say, well, you know, I noticed in this deposition that you said that you did, in fact, order a vanilla milkshake on that night. And he would put the paper in front of the witness. Didn't you, James?

[00:42:22] [SPEAKER_04] You look at it. Yes, yes, I did. In fact, I remember I had a vanilla milkshake that night. And didn't you, James, didn't you drive a Toyota between New York and Akron on the 5th of July of 2009? And did I have, it was a rent-a-car.

[00:42:52] [SPEAKER_04] Was it a Toyota? I don't know. And he'd pull another piece of paper and he'd put it in front of you. Yes, yes, oh yeah, I did. I drove and I rented that Toyota. And James, didn't you sign the paper in that bank that basically admits guilt?

[00:43:17] [SPEAKER_04] And the witness would be flustered and say, yeah, yeah, I did. Even when he didn't do it.

[00:43:25] [SPEAKER_04] So he would, in Bailey's mind, he would trick a witness who was crafty and was obfuscating the truth and use this tactic to get him to admit the crime or to settle out of court, whatever it was. And so after he said that, I realized, okay, I got to pitch the book aside.

[00:43:55] [SPEAKER_02] Because without the book, what he's showing the witness is he's got this confidence of he knows the facts. He only needs the paper to prove to the guy who actually did the action the facts. He knows the facts without the paper. So it's kind of this weird power to not have the paper in front of him.

[00:44:15] [SPEAKER_04] That's right. And it goes beyond that when I think about it. When you're interviewing somebody, like both of us, we're looking each other in the eye. Neither one of us has papers. We're equal in a sense. When the reporter goes in with the sheep of questions, it's not really equal.

[00:44:34] [SPEAKER_02] Yeah, it's like a status thing.

[00:44:35] [SPEAKER_04] One person's got questions written out and the other is in the dark as to what the questions are going to be. And so in a certain way, it makes it fairer. It makes it more comfortable, I find. Because I noticed when I did have questions written out, it was before I tossed the questions away.

[00:45:02] [SPEAKER_04] Like you would often see people like leaning over to see what the question was. And so it makes it much more comfortable to just have a regular conversation.

[00:45:12] [SPEAKER_02] Yeah. And which builds on the connection. And also it kind of emphasizes your—it's improv. It emphasizes your creativity and your willingness to connect with the other person. Which I'm going to finally circle all the way back to my first question, which is, what question did you ask this beautiful Brazilian woman on a bus that led to a decades-long marriage?

[00:45:39] [SPEAKER_02] Like I can't imagine—like I see, you know, beautiful people all the time. I would never walk up to them and then ask some question that would create a decades-long marriage.

[00:45:50] [SPEAKER_04] Okay. So here's the thing. And here's the setup to this. So all that time, I'm walking down the aisles for 10 years looking for people. If I saw a beautiful woman, beautiful young woman next to an empty seat, I would not sit down next to the beautiful woman. Because—

[00:46:10] [SPEAKER_02] Because every guy's doing that.

[00:46:12] [SPEAKER_04] Number one. Number two, look, she's not taking me home.

[00:46:15] [SPEAKER_02] Right.

[00:46:15] [SPEAKER_04] I need a conversation to happen that is going to make that person say, wow, wouldn't it be great if this guy would come home and meet my friends and I became friends with this guy? Whereas it's for a beautiful woman, she's probably being hit on all the time. And it's just very—in my case, just look at me. It is my case. There's not much chance.

[00:46:45] [SPEAKER_04] I'm not a pickup artist. So I'm not going to sit next to her and get her to invite me home. I thought. I thought. And so for years, if I met a beautiful woman, it was not that way. And I get an assignment to find the most beautiful beach in the world. That was in South America.

[00:47:13] [SPEAKER_04] And I had heard about this beach called Jete Quacoada in Brazil. It was like the most—a beach that was like no other because it had like sand dunes from the Sahara set next to crystal waters of the Caribbean. The juxtaposition of those two. Plus, it was so rustic. There were no hotels.

[00:47:40] [SPEAKER_04] I was even told when I first heard about it, they don't take money there. You—to get there, you have to go on an old-school boat and then take a mule. And you carried a sack of rice on your shoulders to trade with a fisherman for a hammock in front of their little home so you can sleep. And they would feed you too.

[00:48:09] [SPEAKER_04] So I got to get to this place. Got to see this place. Jete Quacoada. And I get to the nearest big city. It's called Fortaleza. And as luck would have it, I arrive on a Tuesday. And Friday night, the first travel agency tour of Jete Quacoada is taking place. A bus is going to leave from Fortaleza at midnight on Friday. It's going to take us halfway.

[00:48:39] [SPEAKER_04] And then they're going to have these dune buggies take us the rest of the way. Don't need a mule. Don't need a sack of rice. Perfect. Get my ticket. And I get one of the last tickets. And so I wait till Friday. I'm there at night aboard the bus. What I don't know is that that morning, that Friday morning, a Brazilian woman called up the travel agency and said, I'd like a ticket to Jete Quacoada.

[00:49:09] [SPEAKER_04] Well, I'm sorry. We're all sold out. But I got to go. Well, the next bus is going to be in two weeks. I can sell you a ticket for then. Nah, she says, I got to go today. But we got no seats. People heard about it. It's the first tour. And it's all sold out. Well, if somebody cancels, can I get their seat? Absolutely. Give me your number and I'll call you back if somebody cancels.

[00:49:38] [SPEAKER_04] Well, she gives her number, but she doesn't wait. An hour later, she calls back. Any cancellations? Guy's traveling. She says, no. Hour later, she calls back. No. Hour later. Hour later. Every hour on the hour, she's calling back. And finally, at 10 o'clock at night, the guy says, look, there's just, there's no cancellations. Everybody wants to go to Jete Quacoada. But I can tell how much you really want to go. So how about this?

[00:50:06] [SPEAKER_04] For half price, you can stand in the aisle. Great, she says. Runs off to the bus station. So I board just before midnight. I take a seat on the aisle in the middle of the bus. It's completely dark. Waiting, waiting, waiting for the bus to start.

[00:50:29] [SPEAKER_04] Just before the doors close, I see this silhouette come up the steps, turn down the aisle, and is walking, walking, walking, and stops right next to me. And I look up, and I know, like, there she is. That's my wife. You knew that. Without, I can't even see her face. And so the bus starts rolling.

[00:50:59] [SPEAKER_04] And after a couple of minutes, I look up at her, and I said, would you like my seat? Because I know. And she looks at me and says, no. And turns away. Obviously, she didn't know like I knew. And that was the start of what is now 26 years of marriage.

[00:51:26] [SPEAKER_02] So wait, so you're not really, okay, so you asked her, would you like my seat? That was question number one. Really, it didn't work. What happened next?

[00:51:37] [SPEAKER_04] Well, what was really good is that it was about a, it must have been like a three-hour bus ride. And so after about an hour or an hour and a half, the guy sitting next to me by the window stood up, and he just basically put his arms on her shoulders and said, no, no, you sit down and put her in the seat.

[00:52:04] [SPEAKER_04] And that was how we started to talk.

[00:52:09] [SPEAKER_02] So essentially, that guy was the alpha male, just completely like took control of the situation, put her down. You were the beta male. She had rejected you, but now just fortunately, you're sitting down next to her.

[00:52:22] [SPEAKER_04] Well, here's the thing. I didn't, I was certain this was going to work out, but I wasn't, my sense was, look, if I try to be aggressive, this is not going to work out. So I was just playing a long game, I think. Right. Okay.

[00:52:52] [SPEAKER_04] And, you know, I haven't really gone back to examine what was going on. I think my, my feelings was I look up to her, get, try and get a glimpse of her. And because again, you got to realize this is like 10 years of reading body language.

[00:53:17] [SPEAKER_02] It's almost like the, this period of traveling leading up to this moment, which then led to your, you know, hundreds or thousands of amazing interviews with Esquire and your podcast and other places. Because this is, this, these 10 years traveling and asking questions just to survive is almost like the, the Beatles in Hamburg where they got their kind of initial 10,000 hours under their hood

[00:53:43] [SPEAKER_02] without the world seeing, without the world judging their every moment.

[00:53:47] [SPEAKER_04] That's a great way to put it. I never thought of it that way, but that's exactly, I do tell people when they ask, they see people when I, like I give speeches, talks, and people want to know how to interview, but they're always saying like, what question do I ask? And they don't understand that I could give them the same question that I have, but it won't

[00:54:14] [SPEAKER_04] get the same response because it is, they may not ask it at the right time. They may ask it in a tone of voice that makes them, the person asked step back.

[00:54:33] [SPEAKER_04] They may ask it in a way where the inflection is not curious because if it's my question, it's really not their question. It has to come from a place within.

[00:55:04] [SPEAKER_08] You're listening to this podcast. So I know you've got a curious mind. Here's a helpful fact. You might not know yet. Drivers who switch and save with Progressive save over $900 on average. Pop over to Progressive.com, answer some questions, and you'll get a quick quote with discounts that are easy to come by. In fact, 99% of their auto customers earn at least one discount. Visit Progressive.com and see if you can enjoy a little cash back. Progressive Casualty Insurance Company and Affiliates.

[00:55:32] [SPEAKER_08] National average 12-month savings of $946 by new customers surveyed who saved with Progressive between June 2024 and May 2025. Potential savings will vary.

[00:55:43] [SPEAKER_02] So how do you think you, I mean, just in terms of, let's say, skipping those 10,000 hours or tacking it a little bit, how do you, I mean, I guess I can answer this for myself, but how do you get in touch with that inner curiosity with each guest or with the girl sitting next who asked you on a bus or the grandma who you want to stay overnight with, you know, so that you can have a place to live or Muhammad Ali or Amy Schumer or whoever it is you've interviewed?

[00:56:13] [SPEAKER_04] Well, what I've done with crowds of people is to show them that they can reboot their curiosity because very few people stop and think about what's happened to our curiosity.

[00:56:39] [SPEAKER_04] When you're four years old, you're asking your parents up to 400 questions a day, driving them nuts.

[00:56:45] [SPEAKER_02] Is that a fact, like 400 questions a day?

[00:56:48] [SPEAKER_04] At least one survey I read stated that a four-year-old can ask up to 400 questions a day.

[00:56:56] [SPEAKER_02] And what does a 40-year-old ask?

[00:56:58] [SPEAKER_04] I don't know, but it's a lot less. I think they, from what I understand, four years old is the period where you're most curious because you cannot start to articulate or most curious your questions because now you have the command of the language to articulate and you don't know a lot. So it's natural to ask why, why, why?

[00:57:24] [SPEAKER_04] What happens is you're five, you go to kindergarten and there's this role reversal where all of a sudden it's the teacher who's asking the questions and the teacher is saying, if you have a question, you don't just blurt it out. You raise your hand and wait to be called upon, which in order to make the class function,

[00:57:48] [SPEAKER_04] it makes sense, but you've already now set up a dynamic where you cannot be spontaneously curious. You now have to raise your hand and wait for the chance to ask your question. And all you got to do is just start asking teachers in schools what happens to the raised hands over the years by the time it gets to middle school. Very few hands are going up.

[00:58:19] [SPEAKER_04] Because the curiosity is like slowly beaten out of us. And if there is one hand that goes up with a curious question that makes them seem foolish, well, back in my day, this was a long time ago, that person would be mocked by the rest of the class. Can you imagine what it's like in this day and age

[00:58:44] [SPEAKER_04] where somebody can go on their cell phone and say, can you believe what this kid just did? And now it's all over the world. And so I think people may tend to keep their cards close to the best and not want to ask something that's going to get them mocked.

[00:59:06] [SPEAKER_04] And then you start to go through life and you get a job and you have a question. And there are four or five people from the job around and you start to wonder, if I ask that question, I need to know the answer to do my job well. But if I ask it, everybody's going to know I don't know the answer. They're going to think I don't belong here.

[00:59:34] [SPEAKER_04] So they swallow the question. And what you were saying before about answers having so much power, it's the leader is the one who has the answers, is the person to aspire to, not the person who has the question, because the person with the question doesn't know the answer. And so I think what's happened is we've lost this curiosity,

[01:00:03] [SPEAKER_04] but you can get it back. You can reboot it. Because if you just can think of yourself as a child again, it's still in there. It's still in there and we hardly know anything. So I've noticed what I do is I put people through interviewing exercises where for two minutes,

[01:00:31] [SPEAKER_04] they have to interview one another as if they are the boss and they're looking to make a hire. And then I give questions for the same two people to ask each other. And they can see how after my questions, how much deeper they've gone, how much more they know.

[01:00:59] [SPEAKER_02] Why is that? What do you think is the difference between your questions and theirs? Like what's an example?

[01:01:04] [SPEAKER_04] Okay. Well, one of the questions I might ask is why is your best friend, your best friend? As opposed to what did you do at your last job? That's right. And, or what's the best lesson your father taught you? Which is how you opened up garbage shop. That's right. Exactly. And you see, and the people can see after literally four minutes,

[01:01:34] [SPEAKER_04] I guess four minutes each way. So it's eight minutes. They can see by just changing their questions, how much more they know about the person, how much deeper the connection they've made. I mean, you see people crying at, at the end of somebody asking somebody why their best friend is their best friend. Because the person that didn't expect to be asked that question,

[01:02:01] [SPEAKER_04] maybe something was going on in their life at just that time that was really difficult. And their friend came in and really helped them out. And all of a sudden that just flew to the surface. Well,

[01:02:15] [SPEAKER_02] it's like your, your experience with Gorbachev where you ask him, you know, he's expecting you to ask about like Reagan and nuclear politics and you were pressed for time. And you suddenly asked, what's the thing you learned the most from your father? And he tells you this really kind of sad, almost tragic story about his father being shipped off to World War II. And he has this memory of eating ice cream the moments before.

[01:02:41] [SPEAKER_02] And that kind of really is such an important answer because it triggers for him, the tragedy of war and why he wanted so badly to end the Cold War. And it becomes an important question. This, this almost off the topic question.

[01:02:55] [SPEAKER_04] And, and what happens out of that, which people don't realize because you have to be seated in the room and watching this, the subject respond to that question. But when it's, when they're done, they want another question like that because you took them to a place that they're really glad they thought about. They, they would have never had that thought if it wasn't for your question.

[01:03:26] [SPEAKER_04] And once, their mind has been flipped that way, they want to talk to you. I had this experience. And I can't reveal the person, but I was just interviewing somebody who's like one of the most famous people on earth. And quite similar. I asked this person.

[01:03:49] [SPEAKER_04] I asked this person a question that they had never told the story and they'd been asked 10 million questions in their life. And you see the reaction on the person's face. And you see the reaction on the person's face. Like, wow, I've never told that story. And when you can ask that question, you get back the respect and they will lean in and they'll,

[01:04:16] [SPEAKER_04] they'll want to give you better answers because the better question will get the better answer. The question that is can generally gets you a canned answer. Yeah. It's simple formula.

[01:04:31] [SPEAKER_02] So I'm going to ask you a question related to the best friend question, which is you have breakfast every day. When you're in LA at home with your family, you have breakfast every day with Larry King. So how did that happen? So I went to, and he's one of the greatest interviewers of all time, obviously. Yeah.

[01:04:52] [SPEAKER_04] And I had met him when I did, went to do an interview with him for Esquire. And then years later, he was doing his soup to nuts autobiography and we connected on that. And so I helped him write that book. And when I went out to interview him for that book, he said, meet me at breakfast. He starts his day every day with breakfast back then. He's at a place called Nate Niles.

[01:05:20] [SPEAKER_04] It's kind of a famous deli in Beverly Hills. And so I walked in on day one and he had a lot of friends around him. Everybody was over like 75 at the time. And I just would come to breakfast every day. And then afterward, I would be able to interview him for the book. And so it became a habit.

[01:05:45] [SPEAKER_04] And I would say about the book was done maybe 10 months later. And by that point, we had just been going to breakfast every day that it couldn't just end. We were friends.

[01:05:58] [SPEAKER_02] So what have you learned from him about interviewing? Because obviously, like let's take the great interviewers out there. And a lot of times when you say this list of names of the great interviewers out there, people, there's a lot of mixed reactions. Because often these people are not, I don't know why, interviewers, like the best interviewers out there are almost considered like a tier down from like the best intellectuals or reporters. But like, if you look at Larry King, Oprah, Howard Stern,

[01:06:26] [SPEAKER_02] these are the greatest interviewers in history, but they're not, they're somehow not considered in the same level of, of the intellectuals of the world. It's the ones with all the answers, even though they're the ones getting all the answers.

[01:06:38] [SPEAKER_04] And there's a great reason for that, because oftentimes intellectuals will have trouble making the connections in order to get answers. Larry is salt of the earth. He can talk to anybody. And not only that, but you sit with him at breakfast and everybody does come over, including like six-year-old kids. And he will connect with everybody.

[01:07:07] [SPEAKER_04] You think of Oprah and you're really lifting the level of genius because, not above Larry, it's just in her, what she did was like being an Olympic diver, doing a dive that has a higher degree of difficulty factor because,

[01:07:32] [SPEAKER_04] like Larry is sitting at a desk and he's got a guest and a mic between them and TV cameras. So Oprah is on her couch and got a guest and there's TV cameras. But there's also an audience there that she's playing off, which as a stand-up comedian,

[01:07:56] [SPEAKER_04] you know that's going to completely affect every moment in the room. Right. So she's got a producer in her ear, an audience in front of her, cameras coming at her from multiple directions, plus connecting with the guest. Now that's pretty amazing, I think.

[01:08:20] [SPEAKER_04] And at the same time to maintain that place of connection with anybody else who's at the seat, whether they are a billionaire or whether something tragic happened in their life and she's revealing the story. That's pretty amazing.

[01:08:44] [SPEAKER_02] I like how you refer to it almost as like this Olympic level effort because when I see your interviews, what impresses me and particularly as, you know, when preparing for this podcast too, it's, it's, I see who you're about to interview, you know, when I'm looking down the list of articles or podcasts or whatever, and I'm thinking to myself, okay, what question is he going to, I'm not thinking of them. I'm thinking of what question is Cal going to ask to open them up? So like with Dr. Dre,

[01:09:15] [SPEAKER_02] you know, I, I, I'm now spacing on the exact wording of the question, but like, you know, how many, how many hours did you stay awake for your longest in, in a row before, for your longest project? Cause that sort of, is this weird question, but it sort of shows how passionate or hard work it is. It's going to reveal something a little deeper than just a number.

[01:09:37] [SPEAKER_04] And, and not only that, it's, it's a question that he's not going to shy away from. Again, he's going to think, wow, what is the longest I ever stayed awake to finish a project I was passionate about. And now he's got to run all the different experiences through his mind. And that's probably going to make him feel good because there's going to

[01:10:04] [SPEAKER_04] be a lot of successful moments in there. There's going to be a lot of overcoming and triumph. And, and then he's got to settle on, I think it was 79 hours. 79 hours is the longest.

[01:10:23] 72.

[01:10:24] [SPEAKER_04] 72. Okay. 72 hours.

[01:10:27] [SPEAKER_02] Not, not to embarrass you, correct your own, your own interview. So,

[01:10:33] [SPEAKER_04] and he's basically saying, look, when I'm doing these projects that I'm passionate about, I don't even think about going to sleep. It's just about getting it done and being in the moment with it. And what happened to me was after I got up to speak for the first time, I don't know if you know the organization Summit.

[01:11:03] [SPEAKER_04] Yeah. They, it's an entrepreneurial organization. They have events around the world. or two, two or three years ago, they did it on a cruise called Summit at Sea. And you get entrepreneurs from around the world come in and great speakers. And this last year they did in LA, Jeff Bezos was there. It's, it's really high caliber people that you can go hear.

[01:11:30] [SPEAKER_04] And so I got asked to go and speak about decoding the art of the interview. And I'm thinking, you know, you have, you know, CEO of Google there who, who's going to come see me. But I figured, you know, it was a free weekend in the Caribbean. The hell. So I go to speak. And when I arrive, the room is packed. Not only is it packed,

[01:12:00] [SPEAKER_04] but there are people crunched to the back wall. There are people sitting cross-legged in the aisles. And there's a long line out the door. It's like being a performer. And I had never really given a speech before. And when I got done, it was standing ovation. And I was like stunned. And I couldn't, I'll be completely honest.

[01:12:27] [SPEAKER_04] I couldn't understand like why there was this attraction in the first place. And it took me a minute. Because a long line of people were waiting to meet me afterward. And they were all entrepreneurs. And they wanted to know what questions can we ask to hire better?

[01:12:54] [SPEAKER_04] So I was like speaking to the perfect crowd. Because they, all you have to do is make one bad hire. And you could blame it on the hire, but it's really your fault. You interviewed them. You should have known. And so all these people knew that. And they wanted to know how they can improve the way they interviewed.

[01:13:21] [SPEAKER_04] And so one of the first people came up to me and said, we're this startup company. We're filled with passion, my partner and I. And we can't seem to hire people that are as passionate as we are. What questions can we ask to figure out how passionate they are? So I said, just tell them the Dr. Dre story. And the question applies to any business that's looking to hire passionate people.

[01:13:51] [SPEAKER_02] I feel like you should write a book like Cal Fussman's 100 Questions. And again, you said earlier, you could take your questions, give them to someone else, and they could get, do it completely wrong or have, it's all that. And I, you know, there's kind of an element of the 10,000 hours that still requires actually doing something and enduring through it and, and having the experience and so on. But I feel like your questions are so interesting that just get writing the book,

[01:14:19] [SPEAKER_02] Cal Fussman's 100 Questions will help people to kind of skip a level.

[01:14:26] [SPEAKER_04] Well, you know, I am going to work on a book and it's a great concept.

[01:14:32] [SPEAKER_02] Cause you can take like, here's Dr. Dre's questions. Here's the question you asked Kobe Bryant. Here's the question you asked Amy Schumer. Wow. This is smart. I'm glad I came here today, James. That's free. I don't charge for any of my ideas. So I would read that cause I want to know. Wow. That's amazing.

[01:14:52] [SPEAKER_04] You know what? I'm going to really give that some serious thought. I was, I was in the process of putting together a book proposal, but what you just came up with is much simpler.

[01:15:03] [SPEAKER_02] And then it's a format too. It's like, don't sweat the small stuff. And then they, then the guy wrote, don't sweat the small stuff for kids. Don't sweat the small stuff for parents. Don't sweat the small stuff in relationships. Then you can like, Oh my goodness. On a first date. Alpha was a hundred questions for kids. Because like when you talk to, like when I talk to my kids, they don't want to answer questions. It takes a while for them to open up. Like if I just say how school, they block me out completely. I have to ask like, I'll give you a great example.

[01:15:28] [SPEAKER_04] I'll give you, and I'll give you a great example. This is a really good idea, James. Thank you. You're welcome. Go for it. So there's a Nobel prize winning scientist who was asked, like, was there a difference between the way you were raised and the way other kids were raised that enabled you to win a Nobel prize? And he said, yeah, there was. What was it? Well,

[01:15:58] [SPEAKER_04] when I was a kid going to school, the other kids would come home and their parents would ask, what'd you learn in school today? And all the kids would say, nothing. When I got home, my parents would ask me, what good questions did you ask in school today? And it's just by changing the question,

[01:16:29] [SPEAKER_04] you can change somebody's life because now the kids got to be thinking when they go to school, what is, what is my question of the day?

[01:16:41] [SPEAKER_02] That's so funny. It reminds me of a little bit, Sarah Blakely, you know, the founder of Spanx.

[01:16:48] [SPEAKER_04] That's my favorite podcast that you did.

[01:16:51] [SPEAKER_02] Oh, thank you so much. Man, that was great. She was so great and so inspirational, but, but, and she said when she came home from school every day, her dad would ask her, what did you fail at? Right. And I thought that was very interesting. Yeah. And changing the question changes lives.

[01:17:05] [SPEAKER_04] And, and then she went around door to door selling fax machines or something. Yeah.

[01:17:10] [SPEAKER_02] Something like that in years.

[01:17:12] [SPEAKER_04] And so what a way to accustom somebody to pushing on through failure.

[01:17:21] [SPEAKER_02] Yeah. It's, it's beautiful. But that's why these ideas, like a hundred questions for kids, we just came up with two that are, you know, life changing for both the parent and the child. Wow. Like one, won a Nobel prize. The other became a billionaire just by the way the parent asked questions. So now you have formats.

[01:17:43] [SPEAKER_04] You know, as soon as, as soon as I walk out this door, my literary agent is getting a call. Now, you know, it's, it's very interesting the way you frame this. Like how, how do you think in order to frame like that? How, like what, what, what runs in your mind that enables you to, it's almost like you saw a business right there in, and then not only that business,

[01:18:13] [SPEAKER_04] but it connects to this business and it connects to this business. Like, where does that come from?

[01:18:19] [SPEAKER_02] Also, now you're asking.

[01:18:20] [SPEAKER_04] All right. Now I'm sorry. You know what? But that's fine.

[01:18:22] [SPEAKER_02] I'll tell you, I'll tell you. One is I'm curious. I want to know your hundred questions because it seems like with each person, they're different. And so it'd be great way to, and you talk about in, in, um, I think it's your Ted talk, uh, uh, talk to the heart first and ask a question that opens the heart where so many people ask questions that are just for the mind. Uh, talk, you know, it's like what you said to garbage off as opposed to asking about nuclear weapons. You ask about his father. So you talk to the heart first,

[01:18:52] [SPEAKER_02] but now I want to think what are the hundred ways you've done to kind of like open up the heart? That would be interesting to me, not only as an interviewer, but as, as a parent, as a, uh, you know, uh, you know, in relationships and, and, and in many different situations. And so I want to know, but then I'm thinking to myself, okay, as a business, business requires simple formats that could be scalable. And so you look at, again, I start to think of what's something common.

[01:19:22] [SPEAKER_02] Don't sweat the small stuff. It reminds me of where that format was so easy for him to slice off into,

[01:19:27] uh,

[01:19:28] [SPEAKER_02] you know, he sold like what? 200 million copies of his books. Um, because the format was so simple. He had written another book prior to don't sweat the small stuff. I think it was called how to be happy, but nobody bought it. Nobody bought it. And it was when he did this don't sweat the small stuff. He created a format that was scalable.

[01:20:00] [SPEAKER_04] Well, you know, we were talking before when, when we met out in the street, uh, and I explained that I'd just been in Spain and I was looking at a Picasso,

[01:20:11] uh,

[01:20:12] [SPEAKER_04] famous Picasso piece called La Guernica. And the amazing thing about it was how in the very beginning, he did this in a month. And it basically was a reaction to a bombing of a village in the Spanish. And so it's,

[01:20:32] [SPEAKER_04] you're basically seeing heads and mothers with dead babies and all sorts of images that just make you stop and ponder man's inhumanity to man. And the interesting thing to me about this experience was his girlfriend at the time was a photographer.

[01:21:00] [SPEAKER_04] And she photographed this painting or this drawing being done along the way. And you saw in the very beginning, so many more images. They're all over the place, different kinds of images. And then as the process moved forward, the work got simpler and simpler and simpler. So at the very end,

[01:21:28] [SPEAKER_04] it was everything he wanted to communicate in the most simple form. And like you in some way did that, like in a, and it just finger snap.

[01:21:40] [SPEAKER_02] I think, uh, maybe that's my mute. I think that's your superpower, I'm simplify, man.

[01:21:47] [SPEAKER_04] Well, when, when you think of business, like you've started what? 20 businesses more. Do you think that way to start a business?

[01:21:56] [SPEAKER_02] Yeah, you have to, you have to, uh, think what's the simple, what's the simplest thing you can offer someone where they're going to say, I need this. And they might not even realize they need it. So you have to dart around with the right questions and you figure out, you know, like I was, we were talking, um, we were talking to Jim Cramer on the podcast the other day. And I asked him, how can he simplify his life?

[01:22:23] [SPEAKER_02] And cause simplification is a very important issue. And he said, well, first I would have to stop doing my TV show, mad money. And I'm like, no, no, no, that's too complicated. Then you're changing your entire career in life. Like you're stopping the TV show that made you catapulted you to fame. What would be something else? Uh, you could do. And we kind of concluded if he just wrote 200 words a month about sports for ESPN.com, um,

[01:22:50] [SPEAKER_02] he would fulfill this passionate passion in his life cause he loves sports. And maybe that would help him find the right direction of where his next passion would be at the age of 63. And so, you know, you just, it's always the smallest steps possible. And you also, you want to make life easy for yourself. You don't want to work. You don't want to work too hard.

[01:23:09] [SPEAKER_04] It's, it's amazing.

[01:23:10] [SPEAKER_02] Like he can stop one article a day for wherever he was writing. Cause he writes like four articles a day. He could just stop one. Nobody would miss it. And then once a month, he could write 200 words for ESPN.com to bring alive this passion.

[01:23:24] [SPEAKER_04] So he felt that this part of his passion had been squashed.

[01:23:28] [SPEAKER_02] Yeah.

[01:23:29] [SPEAKER_04] And it was buried underneath all this work that he was doing.

[01:23:33] [SPEAKER_02] Cause all he would talk about in the podcast was sports. So clearly the passion was there. Wow. And, but he just never thought about writing 200. No, no one's going to die. If you were ahead of ESPN.com and Jim Cramer calls you and says, can I write 200 words a month for you? You're going to say yes, of course.

[01:23:50] [SPEAKER_04] And yeah, it's not about the money for him.

[01:23:52] [SPEAKER_02] Yeah.

[01:23:53] [SPEAKER_04] This, this is simply about doing his passion.

[01:23:58] [SPEAKER_03] Yeah.

[01:23:59] [SPEAKER_04] Well, I'm coming. Simplicity has reached me like through the podcast because much more complicated. To be a writer than a podcaster.

[01:24:12] [SPEAKER_02] Yes. But let me ask you like, cause I deal with this. I feel with podcasting is great. And I get to meet so many fascinating and interesting people as do you. I mean, your, your list of guests is, is, is your, your, you're starting, but it's, it's already like such a fascinating list of guests, but you're talking to them. So people don't talk to you. They don't get your story. So writing is where you get your story out there a little bit more. And I feel both are kind of needed still.

[01:24:41] [SPEAKER_04] It's a good point. I was just thinking of it from the perspective of the amount of time that it takes for me to write something. Even if I was interviewing Kobe Bryant and I then had to go back and go through the transcription and find exactly what he said and put it down in just the right way.

[01:25:11] [SPEAKER_04] Very different from me. Very different from me just doing the back and forth. It's taped. I do a little introduction and it's on to the next. And there's something very Tim Ferriss about that.

[01:25:27] [SPEAKER_03] Yeah. You know,

[01:25:27] [SPEAKER_04] the four hour work week.

[01:25:28] [SPEAKER_03] Yeah.

[01:25:28] [SPEAKER_04] Which at the very beginning, I looked, I looked at that book and I just scratched my head. But now I'm kind of living it because when you think about it, I, I would do for Esquire one issue a year. And this is years ago, every January, they don't have a January issue anymore. The magazines are shrinking,

[01:25:57] [SPEAKER_04] but every January, the issue was basically mine. It would be filled with these, what I've learned columns where you'd get these, we're talking about the word icons, but in an issue you might have Jack Welch and Muhammad Ali and Donald Trump and first supermodel, Lauren Hutton, Christy Brinkley. Uh,

[01:26:27] [SPEAKER_04] it might be 20, 20 people of that ilk in, in the magazine. And it would take me a long time to do those interviews and put down those words in just the right order. where what I'm noticing in the podcast is I literally, if scheduling could be done where all the people are in the same city, I could sit,

[01:26:56] [SPEAKER_04] I could literally sit in one place or even move around the city. I could do four or five of these a day.

[01:27:02] [SPEAKER_02] Yeah. And what I've noticed, and you're probably noticing more people listen to a podcast and read an article. And not only that,

[01:27:12] [SPEAKER_04] but I think, I'm just looking into this and this, I'm going to ask you if you will come on my podcast and we can talk about this because you're already in middle of the, the podcast. Like I'm just getting started, but it seems to me that you have this group of people that is like highly connected to the internet, wearing earbuds.

[01:27:41] [SPEAKER_04] And they love this. There will be people who listen continuously to podcasts. And I'm thinking somebody like my dad, who's 87, he would never think of listening to a podcast. But now that I have one, now he's listening to podcasts. And if it's reaching my dad in some way,

[01:28:10] [SPEAKER_04] it's because now he knows he could listen to other people. Then I think there is a whole group of people who are not yet listening, who are going to listen pretty soon.

[01:28:25] [SPEAKER_02] Right. Like everybody has either made the decision in their lives. I'm going to read books or I'm not going to read books. So everybody on the planet has already made this decision. And with podcasts, because it is still, let's call it inning two out of nine innings. You know, there's a hundred million people commute to work every day. While they're commuting, they're not reading a book. They usually, they're listening to music or they're listening, or they have the choice to listen to music or listen to news or listen to podcasts.

[01:28:54] [SPEAKER_02] And people in the gym, I don't know how many people go to the gym every day, but they're not reading a book at the gym, but they are listening to podcasts. So there's a big audience that once they touch the world of podcasts, it's changed their commuting life. It's changed their gym life. It's changed other parts of their life. All these times, periods of time that are open to them where they never would have read books anyway. And so it's maybe fortunate, maybe unfortunate, but just people are choosing podcasts over books more and more.

[01:29:21] [SPEAKER_04] And it seems to me when I go by the magazine stands and I, you know, pick up a magazine like time and it's like 56 pages. It's, you just get the feeling that, you know, in another decade, I just don't know that, you know, these,

[01:29:48] [SPEAKER_04] these magazines are going to be out there or, you know, they just keep losing thickness, losing thickness,

[01:29:55] [SPEAKER_02] losing thickness.

[01:29:56] [SPEAKER_04] And at the same time, you know, I'm, I'm told terrestrial radio is having problems too.

[01:30:02] [SPEAKER_02] Yeah. Cause it's podcasts.

[01:30:04] [SPEAKER_04] And so I think what you may see is people who might've gone to the magazine stand in the past, people who might've turned to the radio in the past. Now they could find somebody or something they love and go straight to it. They don't have to sit and wait.

[01:30:22] [SPEAKER_02] Well, same thing with TV. You're never going to have a Seinfeld season finale again with 90 million people watching on TV. That period of television is over, but YouTube videos, like a basic viral video will have 90 million views or, you know, Despacito, we add on the writer of the song, Despacito, that, that, that song's had 6 billion views on YouTube. Like it's just insane.

[01:30:49] [SPEAKER_02] The reach of some of these more, what I call choose yourself media, which is like YouTube or, or podcasting or even, you know, blogging versus book writing. So it's there. The reach is much bigger.

[01:31:04] [SPEAKER_04] This, this is why it's so exciting for me to be jumping into the lake right now. And Tim Ferriss for a year, a year and a half, he was just saying, I said, Cal, do a podcast. What do you, why won't you start? And I was scared. Do you know why? Because I thought I was going to have to show up with one recorders and the microphones and hook the wires and do the audio check. And,

[01:31:33] [SPEAKER_04] and then number one, that was going to detract from my connection. And number two, I feared going through it and then checking, checking the sound and finding out I'd screw the whole thing up. And it was really my fear of technology that held me back.

[01:31:57] [SPEAKER_02] Well, you know, Tim, Tim's funny because, so Tim called me one time in early 2014. And, um, he asked me maybe a hundred different questions about podcasting. And I'm sure he did this with, with several other people. And then a few weeks later, he launched his own podcast because that's Tim's process, right? He, he goes and, and studies and learns as quickly as possible. And he tries to figure out what are the main points to make something a success? What's his, what's his 80, 20,

[01:32:26] [SPEAKER_02] what's the 20% he should focus on to get 80% of the value. And then he goes out and creates one of the biggest podcasts out there almost instantly. And then I'm the one now asking Tim for advice about podcasting. And the advice, the last, the last advice he gave me was, um, you know, double down on it, triple down on it. So, so we brought on like, Steve as producer from,

[01:32:51] [SPEAKER_02] Steve left from television to podcasting and tripled the number of podcasts per week. But then Tim goes on to do genius things with his podcast. Like I love how he, um, takes his podcast, videotapes it, puts it on some random channel on some satellite company. Right. I don't know what happened to the TV show, maybe nothing, but what he, what it allows him is it allows him to start selling the podcast on iTunes instead of just the podcast app, because now it's been a TV show. So,

[01:33:20] [SPEAKER_02] so Tim's always thinking of the frontier. He's, he's good. Well, see that, and this is,

[01:33:26] [SPEAKER_04] this is where I, I got to, I have to start thinking frontier wise.

[01:33:34] [SPEAKER_02] Yeah, but you do though. Like that's, that's how you do your, that's how you get your questions. You're at the frontier of, of that with every single guest you have.

[01:33:41] [SPEAKER_04] That, that, that's true. But the whole business aspect of it, because the other thing that's happened is for years. And from the time I went to journalism school, it was just set up for me to go out and do this work that I love. And other people, it were the Steve's of the world who took, Steve took care of everything. Steve made sure I got my check and I was happy. I go to the bar. I hang out with Hunter Thompson.

[01:34:11] [SPEAKER_04] I do what I love. And Steve makes sure the check is taken care of. Now I got Kevin, the manager, but I'm also understanding that it's pretty wise to think like Tim and to be asking you these questions, because that's what is going to help expand. And I'm really seeing, man,

[01:34:38] [SPEAKER_04] I can do so much more in, in podcasting just because I've got it down to a four hour work week. Yeah. And I, it, it was in, in the January 2004 issue of Esquire. Okay. Maybe there were 20 interviews. I could probably do that many in a week with good time management. And you know, all we need is Steve, set them up.

[01:35:07] [SPEAKER_02] Time management is, is the key. That's the, that's the hard part. Cause you do prepare, I'm, I'm assuming for every one. So that takes time too.

[01:35:14] [SPEAKER_04] Takes, it takes a little time, but I'm also finding out that sometimes you don't want to prepare too much. You want to be able to come in. Remember where you just brought that up where you go in curious. If I know everything. Okay.

[01:35:37] [SPEAKER_04] Now my questions are kind of nuanced as opposed to just basic and simple.

[01:35:45] [SPEAKER_02] Well, but I will, I had to, let's say I'm, I'm preparing for you. It's good for me to know where my trigger points are of where I'm going to be curious. Like as soon as I read about how you met your wife, I was curious, well, what was the first thing he said to, to a beautiful Brazilian girl on the bus? Like, I need to know that answer. And, and then, you know, it's also useful to know how you open up Gorbachev, because I think that's, that's very revealing about you and your whole approach and, you know,

[01:36:13] [SPEAKER_02] how you talk to Kobe Bryant and how you talk to the Muhammad Ali articles, brilliant. And how you interwove kind of storytelling with his history, with your questions. You know, so there's some preparation that has to, I watch your Ted talk. Like, so I see your general approach to, to interviewing and questions. So there's some stuff that has to get done. I listen to the 10 Ferris podcast with you.

[01:36:36] [SPEAKER_04] Yeah. And I get that.

[01:36:37] [SPEAKER_02] And so then I also know what your canned answers are as opposed to your own canned answers. So you go walking on the aisle of the bus. I know you said it before. Right.

[01:36:44] [SPEAKER_04] And, and there's, that is very good to know because you, you could have, if you wanted to move me away from that with your question, because you could have said, well, you know, he, he told that story.

[01:37:03] [SPEAKER_02] But I did, I did a calculated thinking on the spot because I've done this with other people. Uh, I would say, I know, I know the story because I listened to it on the XYZ podcast. Um, it was great. A beautiful story. Everyone should listen to that podcast and the story, but then I'll ask a follow on. But for that particular question, I thought it was, or for that story, I thought it was so integral to your process. And I don't know how many listened to that podcast you did with Tim, like two years ago or three years ago,

[01:37:33] [SPEAKER_02] two and a half years ago. So I figured, okay, tell us, I figured I made the calculation on the fly.

[01:37:37] [SPEAKER_04] And you know where we're in with this? I, I love this because I was going back and forth with this in my mind. Cause as an interviewer, if I had one page in Esquire, I want it to be what had never been seen before. I don't want anybody to look at anybody to look at until I saw that before, but Gary Vaynerchuk,

[01:38:04] [SPEAKER_04] he basically has turned himself into a 24 seven media. Mogul. I don't even know what, what word where he's got people following him and he's just putting out messaging. And it like, it doesn't even matter because if next week he looks back and say, Oh, you know, when I said last week was full of shit, this is what I believe now. He doesn't care.

[01:38:30] [SPEAKER_02] Well, there's, there's, um, there's something like Jerry Seinfeld gives this advice to comedians. Don't assume everybody knows all of your material. Yeah. Like, uh, nobody saw your last week's performance or nobody saw your showtime special. You could go up at a club and do the exact same jokes. 95% of the people in the audience will never have heard them before. So just do it. You don't have to be obsessed with turning over your material all the time. So, so again,

[01:38:58] [SPEAKER_02] like you could keep on saying the same message. Um, and that's why I figured, okay, it's no problem. If he says this story, I just don't like it. Some guests, it's so canned, you could tell they've tuned out while they're telling the story. So then I try to make the shift.

[01:39:11] [SPEAKER_04] Uh,

[01:39:13] [SPEAKER_01] right. Oh,

[01:39:15] [SPEAKER_02] I get with, with what?

[01:39:18] [SPEAKER_01] Yeah.

[01:39:19] [SPEAKER_02] I did. And he told the story slightly differently. You didn't mention the goulash for instance. Right. So, yeah.

[01:39:25] [SPEAKER_04] And, and not only that, but I think when I told it, I, it, it didn't have, I don't think it had a rehearsed setup. I think I was telling the story a little more as if I met you at a bar.

[01:39:40] [SPEAKER_02] Right. And we came at it from a different angle. Right. So, uh, uh, so, so, so I had a different kind of power, but.

[01:39:48] [SPEAKER_04] That's to this point though, is crucial because like Gary V says, maybe 99 out of a hundred people heard me give that message about hard work. And they're, they don't even want to hear it anymore. They're tired of it. They're just going to turn it off. But the one person who didn't hear it is going to lean in and he'll listen to me next time.

[01:40:15] [SPEAKER_04] Now I go back and forth because some part of me would love to just deliver fresh content. All the time, but I'm, I'm moving closer to what Gary V says about using my time to get the most of myself out there.

[01:40:35] [SPEAKER_02] I think that's true because think about the nature of advice. Like you ask these questions to people and all, I highly recommend everybody listen to all your questions that you, all your interviews, your podcasts, read your books. I don't know what specifically you want to, want to mention, but I think invite you, you ask all these questions because you want in part to improve yourself and then lives of readers. I would like to live a life more, more like, you know,

[01:41:03] [SPEAKER_02] with a little bit of Kobe Bryant's work ethic or Amy Schumer's sense of humor or Gorbachev's sense of what world peace means to him. I'd like to learn how these people achieve such, such high, you know, heights in their career. But, you know, at the same time, it's so hard to follow advice. Nobody really follows or listens to advice. So there's something to be said for repetition to get through to people.

[01:41:29] [SPEAKER_04] Yeah, it, it's going to be, it will be interesting because many things that you've said are already like whirling around in my mind. And I'm sure as I'm walking through Central Park, I, I, I'm going to be thinking about a lot of the things that you said. I don't, I don't, I don't, I don't know that you would have to repeat them,

[01:41:55] [SPEAKER_04] but I'm very curious in the hope that we do get to sit down again. And I'll be able to throw more questions at you that will enable you to expound on some of the things that you said. And it's going to take me to a deeper place. I just find, I love this whole back and forth that podcasting provides. I mean, think about it.

[01:42:25] [SPEAKER_04] Years ago, we had time in Newsweek beating the shit out of each other. Like, what are they going to have on the cover? Are we going to beat them? What's their newsstand sales? And you know what? They beat the shit out of each other. And now neither one of them is like relevant anymore because nobody was sitting around having these conversations. And thinking about where things are headed. Everybody was just out to beat each other up.

[01:42:53] [SPEAKER_04] And what I feel about podcasting is there's like this sense of community where Tim Ferriss can call you and you'll help him. And then he starts a podcast and then he helps me. It's, it's really, and I think this is why people want to get in on it. They want to listen because it will take them. Some place new. And you, here's the answer to your question. Oh, I got it.

[01:43:23] [SPEAKER_04] You asked, could you live that life? Of waking up in the morning and not knowing what was going to happen. And you know how you can do it. I could wake up in the morning and I could put some earbuds in and I could start listening to different podcasts.

[01:43:45] [SPEAKER_03] Yeah.

[01:43:46] [SPEAKER_04] Just one after another, after another randomly, just to see what, what I was going to learn.

[01:43:52] [SPEAKER_02] And there's always going to be some insight, some really interesting insight in there.

[01:43:56] [SPEAKER_04] That might be the closest approximation I could make to traveling around the world and staying in the same place.

[01:44:07] [SPEAKER_03] Yeah.

[01:44:08] [SPEAKER_04] You guided me to that answer.

[01:44:11] [SPEAKER_02] Excellent. Well, full circle.

[01:44:16] Well,

[01:44:17] [SPEAKER_02] what, what should, how do people, what should people watch or listen to or read or how do they find you?

[01:44:22] [SPEAKER_04] Okay. Well, the podcast is called big questions. And I guess, you know, the funny thing is I'm just learning how to like subscribe to my own podcast because I, I was so old school. I didn't have a Twitter account or a Facebook account until a young guy that I was fortunate to meet set one up for me.

[01:44:50] Uh,

[01:44:51] [SPEAKER_04] but now like I'm all in, I'm all in on this. I feel like this, you say it's inning two, but I, it's like all new water for me. And I love the idea of going on this journey and podcasting and we'll see where big questions takes us. But I really look forward to you coming on as my guest. So I look forward to it as well. I can,

[01:45:21] [SPEAKER_04] I can learn a lot. You already made me think about the world and in very different ways. And probably one of the things I'm going to do is I'm going to take a day. I'd like to see if I could go like 24 hours of just straight listening to podcasts and see what epiphanies come out of it.

[01:45:41] [SPEAKER_02] Yeah. That sounds interesting. That would be an interesting article for instance.

[01:45:45] [SPEAKER_04] Well, you'll definitely, you know what? I'm going to ask you which of your podcasts you want me to listen to in that 24 hours.

[01:45:52] [SPEAKER_02] That's so hard because if someone asks you that question, you know, I only have guests on who I really admire, who are like heroes to me. And each one is so great. Like we can't even, if we go back, we can't even say who, they're like your kids. Who the best ones are. Yeah.

[01:46:11] [SPEAKER_04] You're not going to admit which of your favorite kids.

[01:46:13] [SPEAKER_02] But, but it's not even that. Like, like it is like my kids. Like they, they're both my favorite. And like, it's not even being insincere. It's like, I could say some guests, some guests where I really couldn't crack it open or I wasn't feeling well that day, but like just the majority of my guests, I just love having those guests. Like, like, I mean, you've done a bunch of podcasts now. Can you really say who is, who is the best?

[01:46:38] [SPEAKER_04] Well, would I, I'll make the question easier for you. who is the guest who spoke about the future and what was going to happen to it? And, and a way that would most surprise me.

[01:46:57] [SPEAKER_02] I don't even know the answers to that. Cause they all speak about, they all make me think about the future. I mean, Jay, you've probably heard a hundred of my podcasts. Oh,

[01:47:06] [SPEAKER_04] Kevin Kelly. You know what? Kevin Kelly. That's pretty good.

[01:47:10] [SPEAKER_02] Kevin Kelly. Peter Diamandis, but those are futurists specifically. So that's kind of like their job. I'm trying to think of who else like inspired me in such a way to change my future. And they're all kind of like equal, not equal. I mean, there's Richard Branson, Ray Dalio, but again, they're like, I mean, everybody again. Yeah. Every, everybody. There's no, I don't have, we, you know, we've had people,

[01:47:39] [SPEAKER_02] we've had people want to be on the podcast. Who are like famous and well-known names, but we would say no, because maybe they were criminals or they were people I didn't look up to, or they would have been so famous. We've gotten a ton of views, but it's just, I didn't want to talk to them. So, uh, cause I'm, I'm not by nature a journalist. I just want to make my life better. So, I'm, I'm, I'm, I'm, I'm in it for selfish reasons also.

[01:48:06] [SPEAKER_02] It's about me to be better and the listeners too. Cause if I'm better, I feel, you know, uh, Brian Regan was giving, he's a comedian. He was giving this talk at Google and he says, when I'm on the stage, I'm not trying to make the audience laugh. I'm trying to make me laugh. Cause I know if I'm laughing, they'll, they should be laughing. Or if they're not, it's their problem. Then as long as I'm having fun, I'm having fun. And so I figure if I'm learning something and I'm being curious and asking the questions that I want to know, then the listeners should be learning something, you know? And so that's, that's my,

[01:48:36] [SPEAKER_02] my general philosophy is like that. So, so I don't know who had the most knowledge. I just know maybe with each one, I try to get as much knowledge as possible.

[01:48:47] [SPEAKER_04] Is there something you want to know about the future?

[01:48:52] [SPEAKER_02] Yeah, but Nassim, Nassim to leave was great because I wanted to learn how to personally be anti-fragile, you know, cause I've, I haven't been to a doctor since I was 18 and I was scared to death. Like what if I actually get sick? I'll probably fall apart instantly. How can I be slightly more anti-fragile? And his advice was to, you know, take a little bit of poison each day or something like that. Wow.

[01:49:14] [SPEAKER_04] Do you know, for years I didn't go to a doctor either. And I remember going to Egypt, and I walked up to the Nile river and I just drank out of it.

[01:49:27] [SPEAKER_03] Yeah.

[01:49:28] [SPEAKER_04] And well, did you get sick? Yeah.

[01:49:31] [SPEAKER_02] I wouldn't do that. Then you have to go to a doctor. Oh man. It's a form of hypochondria to not go to a doctor actually, even if you're in perfect health. Cause I'm afraid if I go to a doctor, I'll get down some, Oh, we found something we need to do an x-ray. And now you're down the medical rabbit hole, but I probably should go to one. I mean, you should probably go to one more regularly. I don't know.

[01:49:55] [SPEAKER_04] You know what? I'm going to start. I'm starting, I'm making a lot of changes and, and that's going to be one of them. But the biggest change is to be trying to think in the way that you just explained how you frame a Cal Fussman's hundred questions in so that it steps forward. Cause like in a way,

[01:50:22] [SPEAKER_04] I think I was waking up every day trying to invent the wheel. Every interview had to be different and there's, there's something to be said for thinking ahead and creating a plan that will enable you to get the most out of your time and the most out of your life.

[01:50:51] I,

[01:50:52] [SPEAKER_04] I've always been in some way chasing the story.

[01:50:58] [SPEAKER_02] It's sort of like, um, do you know what the popular show, most popular show on cable TV is? No. I don't even remember the name of the show, but I remember the format. Guy is looking to buy a house. They show him an expensive house, a medium price house and a low price house. And that's it. That's the format. And they've sold that format to a hundred different countries. And it's, and it's, and it's the most popular show on cable TV every week, you know, next to wrestling or whatever. So sometimes like,

[01:51:24] [SPEAKER_04] you have no idea which one he's going to buy.

[01:51:27] [SPEAKER_02] You don't now, apparently he does. They already know in advance, but like, you don't know when they film, you know, you don't know as you're watching it, which one he's going to buy. And so that simple format is incredibly popular. And the format itself is sold into a hundred different countries. And so, so the agents, the managers, the production company has made a billion dollars, maybe off of this show in a world where nobody's really making money off TV anymore. That TV show wins. It's the simplest possible.

[01:51:56] [SPEAKER_04] It keeps coming back to that word simple.

[01:51:59] [SPEAKER_02] Yeah.

[01:51:59] [SPEAKER_04] Which is what Tim was trying to drill into my head for a long, long time.

[01:52:07] [SPEAKER_02] Now on podcast, like audio quality is important, right? Like you, we did notice a big increase in downloads when we went, when we moved into a production studio and started doing it there. And then there's, if you further the complexity with higher production quality, like a Freakonomics podcast, where you're going and doing, you know, interviewing lots of people and you're developing a story or doing a serial, um, that increases the number of downloads. But I don't know. I like this format where you get,

[01:52:35] [SPEAKER_02] you get 80% of the value for 20% of the work.

[01:52:40] [SPEAKER_04] 80% of the value for 20% of the work. All right. I'm notching that. I'm writing that one down too.

[01:52:48] [SPEAKER_02] and I, but I do want to, well, we'll talk about it more on your podcast. I do want to, I do want to promote all your stuff, your, your podcast, big questions, uh, your, your, your, your column and Esquire, which I wish you would do more of where you're interviewing people, all these great, fascinating people. You know, I don't, I, because I use Google, I can't even remember the name of the column. I just Google Cal Fuss and Esquire.

[01:53:10] [SPEAKER_04] It's called what I've learned, but basically I'm, I'm throwing all my, I'm trying to get my chips into podcasting. Now I'm, I'm speaking, uh, and that jives with having a microphone in front of me right now.

[01:53:26] [SPEAKER_03] Yeah.

[01:53:26] [SPEAKER_04] I'm getting up in front of crowds, speaking at corporations, uh, speaking of conventions. I mean, people have invited me to speak in South Africa to help figure out ways that they can change their questions so that they can help educate all these people that don't have the resources to get the education they need.

[01:53:53] [SPEAKER_04] And they found that they can make cell phones for very little money. And as long as somebody's got that cell phone in their palm, you know, they, they can have access to education. But as long as you think of education the old way, it's not going to change. So I never, I never thought that I would get this much out of my life through my spoken voice. It's,

[01:54:23] [SPEAKER_04] this is all, all new to me. And that's the, that's the water I'm jumping into right now.

[01:54:28] [SPEAKER_02] It's so interesting. Cause I keep telling my kids, like, like take Sarah Blakely. So I have two daughters. I want to, I said, take one goddamn day off of school where you're just going to be tested on like algebra or whatever. Come in and hear me talk to Sarah Blakely, one of the most impressive women in history. Yeah. And hear her story. But we're so programmed to go to the standard education. They just didn't do it. Oh man. That's a, that's a disappointment for me.

[01:54:58] [SPEAKER_04] But you know, there's still time.

[01:55:00] [SPEAKER_02] There's still, there's always time. It's time for you and me. Where, how old are you?

[01:55:04] [SPEAKER_04] I am 61.

[01:55:06] [SPEAKER_02] You're 61. You look a lot younger. I thought maybe you were younger than me. So, uh, there's still time for, for everything.

[01:55:13] [SPEAKER_04] I, I feel like this is the beginning of act three. And I, I can be able to get so much more done so quickly that it's like, I'm going to take the next 10 or 20 years and do more out of that. Maybe the next 30 years and do way more than I got done in the last six decades.

[01:55:43] [SPEAKER_02] Yeah. Cause now, you know how to be efficient, productive. I mean, let me ask you a question. 61. I just need to know how many days a week do you have sex with your wife? I'm just kidding. I don't know. And Howard Stern territory. So, okay. Cal Bushman. Thank you so much for coming on the podcast. I look forward to coming on yours. We're going to be out in LA in April, right? April. Yeah. We'll figure it out then.

[01:56:12] [SPEAKER_04] I'll have my wife there and she'll answer your question. All right,

[01:56:15] [SPEAKER_02] good. Thanks so much.

[01:56:17] [SPEAKER_05] And welcome to Pluto phone. If you know the name of the movie you'd like to see, just stream it for free on Pluto TV, where all your blockbuster favorites are landing all summer long. Catch Anchorman, The Legend of Ron Burgundy.

[01:56:41] [SPEAKER_01] Fantastic.

[01:56:42] [SPEAKER_05] The Matrix Trilogy. Welcome to the real world. Mean Girls.

[01:56:46] [SPEAKER_01] Shut up.

[01:56:47] [SPEAKER_05] Titanic. I'm the king of the world. And so much more. For showtimes, press nothing. They're free 24 seven. That is so fetch. On Pluto TV. Stream now. Pay never.