Explicit

Calculating Risks in a Creative Life, with Brian Koppelman

Published Sep 5, 2024, 4:01 AM

Maria sits down with the great Brian Koppelman (Rounders, Billions, The Bear) to learn about how he navigates risk in Hollywood and beyond. They discuss his methods of determining when a risk is worth taking, how to offset risk with hard work, and the time he bet big on Billions.

For more from Nate and Maria, subscribe to their newsletters:

The Leap from Maria Konnikova

Silver Bulletin from Nate Silver 

Pushkin. Welcome back to Risky Business show about making better decisions. I'm Maria Kanikova. Nate Silver is not with us today, he is on a book tour, but we have an amazing guest instead, one of my dear friends, Brian Koppleman, who is everything I mean. He is a writer, he is a director, he's a producer, he is a musician, he is an actor. He is a kindred spirit and someone who thinks about risk in a lot of the same ways that I do. Because he also plays poker. I don't know how you know him. I originally knew who he was, as many of you probably do through Rounders, people who come to Brian more recently, probably no billions before Rounders, so many other things. That's just like the tip of an absolutely massive iceberg that we'll be talking about today. Brian, thank you so much for joining me.

My absolute pleasure. And I think people now might know me from The Bear.

Ah yes, and people might know you as the computer on the third season of The Bear. I just want to point out that you have a bicycle helmet on the table, So did you ride your bike here? Since we're talking about risky decision making, we're in New York by the way, we're in Manhattan.

Yeah, we're in Manhattan. I made a decision a while ago. You know how you can come home and you're either whether you have somebody who you live with, or you talk to a lot of family member friend and they ask you if you had a good day. I decided a while ago that I wanted to be able to like understand what that meant for myself, not just leave that up to sort of an emotional thing or something that would happen in the middle of my day. So I decided, you know, if I do certain thing, if I journal, if I meditate, if I exercise, and I spend time with people that I love, I've had a good day because I've written something, I've moved my body, I've hugged somebody like those things. Well, but I don't know. Six months ago, some months ago, I decided, anytime I don't have to be on public transportation or in a cab or an uber in New York City, it's a great New York City day. And because it adds to all these other things, so and in looking at all, honestly looking at various risks, the rewards of riding a bike all the time and walking are really great. There's but there is this risk inherent in riding a bicycle in New York City. But you can really mitigate the worst of it. You can't eliminate it. You can mitigate the worst of it by wearing a helmet. Downside is you got to walk around looking like a goofball and it's really confusing, like what to do with the helmet sometimes and sometimes I put the helmet on and like there's not you know, socially, it's not great, especially if you like the older guy in the office complex or whatever and you get off the elevator still wearing your bike helmet. You know you are the fool for the day.

You're someone who's from a creative industry, right, Like you don't come from the statistical background, and yet your way of thinking aut the world. You're someone who Your poker game was the first poker game I ever saw in my life because Rounders was the only time I had ever seen poker played because I wasn't into poker. You were into poker, right. The reason Rounders to this day is like the Poker movie is because you're actually a player. You love the game. You understand the game, you went to the clubs, you did the leg work, you did the research. But I think that the way that you think about the world actually does mirror that.

So I just want to say, my creative and business partner and lifelong best friend, David Livina, and I did that. It's not just me. I just important for me to say, Well, it's right, but it's true.

It's very important for you to say. And actually I would love to ask a question about that that was a risk at the beginning of your career, to say, I'm not going to do this by myself. I'm going to have a partner, because if you think about it, like creative partnerships are fraught, and you and David have been partners for how many years now.

I mean yeah, professionally almost thirty years, and but best friends since we were kids, and I think you look back on it and yet if someone knew they were going to be able to really have this career at that time, though, you're not really thinking about downside risk other than to your friendship because your best friend like your brother, and so you're thinking about that. So you have to make you just sort of talk through a process but also we wrote that script together, and I think, you know, each of us just decide to go into it really open minded and open hearted, and it was like, let's let's write this thing together. And then as we did that, and as we felt like this creative partnership was what we'd hoped it would be, we were bringing out kind of the best of each other, it just made sense to roll in and continue. We've never had a signed piece of paper.

I was I was just about to ask that.

And you know, people will say you have to. We've signed many agreements together with other parties, meaning if a studio or network wants to engage us, we both have to sign that document, and we've signed leases, toget, We've signed many many things together. But David and I have never had more than a handshake and a hug agreement with each other.

So you've never actually talked about and said this is going to be a fifty to fifty partnership.

And yet well we've said those words to each other, everything's fifty to fifty.

Of course, we've never written it down, never.

Written it down. In fact, I think those conversations we didn't even email that to each other. I mean that was just like, we're fifty to fifty and everything, and they would it was.

My mind is breaking right now, by the way, at that level of trust. Right, you know the types of topics that I write about, right, Yeah, you know. I've written about con artists. My next book is about cheating, and I have just come across so many instances where that just sours. And you've been doing this for thirty five years, You've never had a written piece of paper. You took that risk, and yet here you are. You're just such a beautiful testament to like the fact that not everyone sucks and that there's actually there are humans that you can take this risk with. But there's part of my mind. The reason I said my brain is breaking is because I would think that someone like you, who I respect so much and you're so smart, and you're so smart about these risks, I would think that you would say, you know, just in case, let's just sign this little piece of paper.

I understand that way of thinking, and I would advise I might advise somebody, but I think if you can try to silence the voices that aren't your own inside you, right, if you can try and actually listen to the truth, you kind of do know, like your body kind of knows. Not in a woo woo way, I mean your instinct knows because of your brain sending these signals. And if I think about what the battle in life is, it's to become comfortable in your own skin. Because when you are able to have these moments of them and they're fleeting, and then maybe as you live a little bit and you work on it, they can last longer. But if you can get to a place where you have moments of actual calm, moments where you can actually listen to the best part of yourself, most alive part of yourself, you know when you need a piece of paper and when you don't. And especially for someone who studied consure, so now, well, I don't want to This is a proby Privo caster because I don't want to. I don't want to become willis shown in The Princess Bride and use search a logic. But it is true that if you know about cons it's easier to con you on a surface first level, meaning if you're someone who thinks, oh, I know what the wise guys do, then it's very easy for a wives guy to use that and play you sure, but I'm not talking about that kind of situation. But basically, I think David and I knew enough about each other to trust each other. And it wasn't a thin knowledge, it wasn't a quick knowledge. It was we had been through enough things and been there enough for one another and knew that that was the primacy, was to do right by the other person. Our wives were incredibly supportive, and nobody ever would have thought about those risks other than, like I say, to the friendship, but writing rounders are such joy. And then the way that it all came together, that we just knew we were off and running it, and it was actually David who had the inflection point. We finished the script and he sent it to a young manager in LA and the manager said, I know you wrote this with a partner. I can spin it one of two ways, and Dave said, no, I spin it like I wrote it with my partner and we wrote it together, not like that guy. I know about poker, And what I see is like this is we did this together, and I wanted to reflect.

That, Yeah, and that's amazing, and that actually, I think is a really important reminder for listeners of our podcast. Because we always talk about the herd statistics and kind of those types of things, and so it is a good reminder that the human element is very much a part of it, you know, And that's I mean, I'm a psychologist, Nate's the numbers guy, so to me like that, that is an important thing to have in the back of your mind because it's so easy to get lost in the numbers, in the statistics, and it's it's really good to have that sort of a reminder.

You can't be in the art. So but if you're in the arts, So what you said is true.

You went into the arts.

Yes, what you said is true that on the one hand, you know me as your friend. You understand that I've made a study of strategic thinking, that I can read people, I can read situations. But when you make a decision that you won't be happy unless you're in the arts, and for me, it was you know, I knew if I at a certain point in my life, like if I didn't try, I wouldn't be a good father or husband. And because I knew that I would have turned bitter, and that if I turn bitter, you know, I knew if I let the kind of a creative block happen, it would be like a creative death, and like any other death, the toxicity would lose onto those I love. Then I just didn't want that. So I think there are times where you have to turn off rationality and reason in a way that you can make function for your life. So you know, so as I hear people like Scott Galloway, who's a smart guy but with say it's not about what you want to do. You got to pick something you're good at, and well, I disagree. I think figuring out what brings you joy, Like guess this thing I said about where you're working from the most alive part of yourself is valuable. But like, I didn't quit my job to write the first script. Somehow I was, I think lucky enough to figure out, well, if I just take two hours a day and really give it everything I have for those two hours a day, I don't have to put all the pressure on myself that I've quit my job or that I've put my family in jeopardy. I can just work. And I knew then, Okay, I feel really alive doing that. I'm going to keep doing this whether this thing sells or not, whether we can make a career out of this or not, And in fact, doing it allows me to do my job in a much better spirit, more effectively than when I was doing it and daydreaming about being something else. So I could not make it an all or nothing proposition. I could mitigate certain parts of the risk so that I didn't have to think about the risk.

Yeah, I think that's a really important lesson. Let's take a quick ad break and then we will come back to talking about why sometimes to take the biggest risks, you need to actually not take the risk that other people talk about. So, Brian, I think that that's an incredibly important point. I also so did not quit my day job when I was working on my first book. I knew that I wanted to write. And you know, the advice I give to young writers when they ask me is I'm like, unless like you know that you can't not do it, don't do it because if you don't have that fire, it's a shitty way of making a living. Right you don't have I mean, so you're in the director's guild, the writer's guild, so you have health insurance, but you know, if you're just becoming a freelance writer, no health insurance, no W two like no security. I have to plan for like a year ahead because I might have a month where I have an insane amount of income and then a month where I have zero income right where I just don't make anything, and I don't know if I'm going to you know, I can't. It's to this day, right, I have this kind of variation in what I earn, and so I have this, like I have to have this in savings, I have to have this. I have to have this, like I need to know that I can pay my mortgage for.

The next because you're making this big real yes.

Because I'm making this big risk. And when I was working on my first book, so I went to grad school for psychology and everyone's like, Oh, that's amazing. You wanted to be a professor. I was like, no, I wanted to be a writer. I did that so that I had the stability and the brain space to be able to work on my first book. And that's why I went to grad school.

Yeah, it's funny. I don't think about it in the terms of de risking, but it is. You can take this giant risk if you can find ways to d risk along the way to it. But you know, you're you can be in the Writer's Guild, but to keep your health insurance, health insurance the whole time, so you can, I'm saying, I can, I can. I know you're I could have now. Yeah, you know we sold Rounders in nineteen ninety seven. Wow, so like so since then, Yeah, it's amazing, But we managed to stay in the whole time and to you know, always have it, but you have you're aware of it. In the years that are bad, you're really aware of being able to work enough so that you get credit for that core so that that goes toward your health and benefits. And then if you're in it long enough, you have lifetime. But it you know, takes twenty years.

Yeah, And I think that those are all important things to realize. So you knew that you wanted to be in a creative field, and a creative field is an incredibly These aren't the risks that we normally talk about on this show. But I think it's so important to realize that you're taking huge risks and the things that so Rounders you wrote on spec so for people who don't know what that means, you weren't paid.

Well we had there's a yeah, we weren't. But there's a great little story that's perfect for this show, which is because I was in the music business before that. I knew some people who were attendant to the movie business. And Dave and I had the idea for rounders, and he met somebody who we told the idea to a director producer, and that director producer offered us five thousand dollars, and Dave was bartending and offered us five thousand dollars.

I bartended too.

Yeah, five thousand dollars if we would write the script and then he and his partner, the director producer guy. He and his partner would own half of the script. So if we then wrote the script and they were able to sell it, we would split it fifty to fifty. And there was all this other stuff. Oh no, well, it was very exciting. You know, someone offered money, and David had been wanting to do this and he met this person, and you know, he'd wanted to have a career at this. I came through it a little later, but I knew someone who worked. I knew someone who connected me to a woman named Rachel Harvitz, who was at Fine line, which is part of a new line. She's a great Academy Award winning producer now, but at the time she wasn't. She was an executive at a company and her brother was in the Beastie Boys, and her dad he's famous playwright, oh dad, And yeah, but Rachel's super smart. And I smoke got a meeting with her. David and I went up and met with her, and she's like, tell me the situation, but don't tell me your idea. Just tell me the situation. And we told her the situation and she said, Okay, well, I can tell that like the twenty five hundred bucks would be good for EACHU coppleman. You need it less you have a job, but I could see that it would be like a good thing. But I'll tell you this, if with you all having done nothing and having no track record, you have a story and an idea that somebody who also isn't someone who's like filled with money, they're not a huge person. If they're willing to give you five thousand dollars, you should risk losing that five thousand dollars and write that script on spec because if you then sell it and you guys control it, you'll have a whole career. And we left her office and just looked at each other and went, well, that's what we're doing.

That's such great advice. You're you're so you know that the role of luck is something that I think about a lot. Of course, that I think is so crucial. What a lucky kind of moment that that that you had that connection and that you had that conversation, because your career would look so different if you had sold fifty percent from the get go.

Oh for sure, it would have been a different ways. And now that interestingly, because Dave's instincts are great to the person David met ended up becoming a very big person in Hollywood, and we have a great relationship with him. So Dave did spot up on somebody who was going to go the distance, but all of our careers would have been That guy then went and directed a small movie where the actress in it got nominated for an oscar and his career was off and running, and we've often thought about sort of how it all would have gone, could have gone differently. So there's the luck element, but also truly it was a risk question. Yeah, it was like you know, and yeah, I remember was like, well, you guys could get ten grand, you know if you counter, but I wouldn't counter. No walk away.

Yep.

It's a hard piece of advice to give, by the way, for sure, a hard piece of advice to give, having been as you have on any other chair. But we were so grateful and I never miss an opportunity to thank Rachel for giving us that advice.

It is. It is wonderful advice, and I think that it's advice that everyone can hear at every single stage of their career because that power to like to realize that you can walk away, that you actually have the risk, but you have the downside, but you also have the upside.

Yeah, it's important to say, like both Dave and I had college paid for and I think that that's a huge advantage that we had. We and I can never And that's not sort of like that's something I've thought about and said for a long time, sort of before it was in vogue to have to always sort of explain away these parts, you know, just but it is just the fact, sure my father was able to pay for college for me. That gave me, when you talk about luck, that gave me the ability to make decisions, yeah, based on a series of things that were quite different than if I had one hundred thousand dollars worth of debt that I had to satisfy. I did right, and that shapes certain decisions, right and absolutely so for me. That gift, it's a huge gift, is a gigantic advantage.

You know, we talked about earlier, not on this pod, but when you and I were just having a conversation. You had asked me about having gone to Harvard, right, and whether you thought that it still had some sort of cachet, some advantage because things are changing so much. And I thought about that question after you asked me, and my answer is that it depends on who you are. For someone like me, yes, it does. Because I wasn't born here. I'm generation zero, I knew nobody. You know. I'm an immigrant, like I'm a Russian Jewish immigrant, right, and having that degree confers a certain kind of it. Just it gives me a check mark that I wouldn't otherwise have that gets me through the door. How did I get into television? My first job in television was as a producer. Well, I didn't start as a producer. I became a producer for Charlie Rose, and that was, you know, that was my kind of before I went to grad school. And the only reason I was able to get that job was through the Harvard Network because there were Harvard people working at Charlie Rose who picked my resume and got me that interview, and then you know, I got in the I.

Think it's magic. To me, those are still magic words. But I'm fifty eight years old, so I know that. You know, I didn't go to Harvard, but I there are certain words in our in the world, in our language that are magic words. Whether they should be or shouldn't be as a different.

That's a different question. But your question to me was are they still And I think for me they were, and they enabled me. I had I had student loans, right, I had no money. I grew up poor. Like my parents had to leave everything behind when they came here, including their passports. Right we had we got political asylum when we came to the United States, And like, I grew up actually poor, and I didn't realize that because my mom is the most amazing person and like never made me feel like we were poor, but we were right, and so I they always supported me and when I said I want to be a writer, Apparently I told them I wanted to be a writer when I was five. I don't remember this, but I wanted to be a writer my entire life. But when I was in college and I kind of went back and forth. I went through recruiting, corporate recruiting, and got jobs as a consultant and an investment banking because I was so nervous, you know, to because I didn't know anyone. I hadn't I was never able to do internships in the summer. I had to work because I made it to be paid, so I didn't have those legs up that you know, people who are able to do you know, Harper's internship and when you go up.

When you got to Harvard, because I remember I was walking one day with my son and like five of his friends at Harvard, and one of his friends was the first not only in his family, but in his entire high school. He was the first person to apply to one of the four those four schools at Princeton, Stanford, Harvard, MIT. And he's like, they didn't even know how, he said, And then a bunch of these young men and women walked ahead and I was standing back with this other kid and he was like, I'll never catch up. And I was like, they're not that far ahead, and he was like no, no, no, I met geographically like they were going to the Hong Kong and I was like, no, no, they're just over there and he's like no, no, no, I mean, how do I catch up?

Yeah?

And I went did you have that face? He's like because there he goes. They all have just and they were of wide, you know, very I mean, my son was the son of two New York writers and it was like before the show, like, you know, and some of the people that he knew there were you know, multi generational, sure wealth and so it you know, counts and things like that. But still they all had a language. Yeah, and this young man didn't have that language. And he literally said to me like what do I have?

Yeah?

And this was freshman year and by the end, he of course had it. But did you feel that at all?

Absolutely? And once again I'm going to say thank you mom, because I remember my freshman year I took a class and this was a totally different context, but I think it gets at the heart of this. I took an intensive Italian class for Romance language speakers, and I spoke fluent French, so you needed to speak you know, some And there was a kid there who spoke Italian because he had trained at Juilliard. He already had a degree from Juilliard as an opera singer. But he didn't know that grammar like he so he was in it. And you know, it was a tiny class, and you know, grades matter. I went to Harvard, right, Like, I'm really competitive. And I was talking to my mom and I'm like, it's so unfair. You know, I can't like, how do I you know, there's this kid and like, and she looked at me and she said, I never want you to say that sentence again. And she drilled it into my head. That's saying that's so unfair. That word unfair should not be in your vocabulary. She's like, life is fucking unfair. Deal with it. Don't worry about that kid. You work your ass off, you compete against yourself, you do what you need to do. Yet it's unfair. Yes, they have advantages that you don't have. My college roommates, who are now my best friends, had money, right, I had no money. I couldn't I couldn't afford like we would do like they would do during like parent weekend, like they would go to dinner and they'd invite me with their parents, and we couldn't go because the restaurants were too expensive for my family. And I never said that to them. And if they're listening to this right now, they're probably going to be horrified because I've never told this to them. And these are my closest friends in the world.

They figured it out by now, probably.

Probably, but we couldn't afford it, Like that's why I never went to those dinners. And there were so many, you know, so many things. And then when I wanted to be a writer, and I admitted to myself that I wanted to be a writer, because I didn't at first, and then like I secretly applied to the fiction Summinar because it was an application process and I didn't want anyone to ask if I'd gotten in or not. And then after I got in that I could talk about it.

Yeah, that's such a scary thing, and that's it. So that's a giant risk. Absolutely one of the things people don't talk about a lot. And I think this stuff applies, you know, I mean, I would say, the risk of coming on this podcast and talking about this kind of fuzzy stuff versus the sciencey stuff is I know that some listeners all may be sort of not why they're interested in this pod, right. Absolutely, I listened to this podcast because I'm a geek about like learning out behavior and risk. I love it. Decision making is really like the such the most important thing, but a big risk. But it is. But I think this is broadly applicable because a huge risk to your own self image is a huge risk. Yes, and we have to be aware and so often well we will not tell ourselves that, but we won't take the risk, so we will downplay it. It's like I was talking to a group of salespeople. I was speaking at some company, you know, a big company, to a group of salespeople, and I say, like, is this true? I have a feeling this might be true because I can relate it to my own world and a job I really want it. I said, is it if you have a really like the day to day if you're a top worker, if you're if you're you know, the top of your field, the day to day meetings you can sell you know, one hundred units of something to somebody. It's it's very easy to do thorough, incredibly deep preparation, but when you have a giant opportunity to present to something where you could sell ten thousand units, it's harder to not procrastinate. It's because if you put everything you have into it and it doesn't work, you are crushed. And all these people agree that it's the bigger the opportunity, the harder it is to actually put the work in ahead of time, even though the reward is the greatest. But there's this feeling about that, and so we have to recognize. I think this is one of the things about behavioral economics in general decision making. Seth Godin talks about the choice and a decision, and like most things are choices, but anything that you recognize as a decision is worth taking some kind of inventory to figure out what is what you're adding up that you're not realizing you're adding up in the process of making that decision. Figure it out. You're stacking a bunch of stuff on the table and it's a seesaw, but you know you might not be able to see out of your peripheral vision, but turn your head and actually look at what's on the both ends of the both ends of the seesaw, and no, it's hard to do this. That's why journal. Like one of the things about morning Pages is if you do morning Pages enough, you find out what you really want. You find out what really matters to you. Same with meditation and the reason. So some of this stuff sounds like anti scientific, but it's not. All these things become to me their data generating things. They help you figure out, kind of like where you are on the hand, if I can return it to poker. And you know when you asked me about poker. At the very beginning, I lost a bad I lost my whole canteen worth of money when I was in fourth grade and Sleepway camp the first time I learned to play poker. My dad had a carouselo chips at home, but he didn't teach me to play. And we played at camp and I lost everything. I had, like thirty bucks to get me through the whole summer, and I lost all thirty dollars and it I was like, I want to learn that game. I want to understand that game. And it was slow coming. Like that experience happened a couple of times because you know, you can learn the game, but then you still have to But at a certain point, I just became really, really fascinated by all the different things you had to be able to stay aware of in order to become decent at poker. And it was fascinating to me, and it was a way gambling is not great for me into any other kind of gambling. Poker I've always been able to keep as a separate thing, and it just brought me a tremendous amount of joy to think through those problems to be most most things in life, it's don't allow you to get to that place where you're hyper present. And yeah, if you know how to think about poker, I'm not great poker player, but if you know how to think about poker, you have the ability to be hyper president at the poker table. And that's a gift.

Absolutely No people laugh at me when I say that. I became much more zen when I started playing poker because it just it put me in that state. We'll be back in a minute. So now, if you extrapolate from that, you you know, you took a huge risk gun rounders, and we talked about that and it kind of led to this whole career. But as you and I have also talked about it, it's not like your career has been like easy going and like oh like after rounders, everything's great, we can sell everything, everything works. I have money, pilon in you know, live in the high life. Right That's that's not how it works. And so I'm very curious to know whether there's a point in time where kind of you took And right now I think nobody can dispute that you're incredibly successful.

Thank you.

So I think you're welcome. But it's very well deserved and very well earned through a lot of hard work. So it's not like you went you know, from zero to I think that, but right now I think that that's kind of that's that's what.

You don't No, I'm listening well lifef like I mean, well, honestly, if life tg anything, the moment you kind of think you're safe, you're not safe. Of course, I never am able to quite say yes, because at the moment I'm not worried about you know, like, getting to pay off your mortgage is a really big deal. I was able to pay off my mortgage.

Congratulations.

No, that's a giant thing in life. Yeah, because they can you know you, yeah, probably can't take it away from you anymore. But right before the show Billions, I mean, I thought we were gonna have to downsize and sell our apartment, and I wasn't sure if I was gonna be able to pay our mortgage. So you know, you never you just never know.

It's I think that's really important, And that's a point that I always make, like, was that a moment where you actually had to kind of think about risk differently? Think about kind of what tell me about that and about that decision making process, and kind of where where you were before before you sold the show, and kind of how you thought about it, how you broke it down.

We had had giant failures. We had written a movie that bombed, and we were supposed to make a television show, and through a series of things, we before we even started, we got fired and an agent called us and said, I just want you to know you're unhireable. And I was like, did you have to make that phone call? We realized it by the no phone call when you called, I thought maybe I was going to get hired, you know, And just I remember this phone call from this agent, and it was in Central Park in the winter, and I was sitting on a bench in Central Park when I got the call and it was snowy and gross, and I just remember it was such a good punch.

And this is a bad scene.

It was terrible.

Yeah, unbelievable, too many, too many negative.

Things, that's terrible, true. And I remember exactly where I was. But here's the thing. I would walk across the park every day. We lived on the west side. My office was at the top of this bridge club with like the top floor of a bridge club on the upper side. David and I and so yeah that at this like little tiny elevator mostly walked upstairs. The final thing was up that stairs. But it was great, loved it, loved this weird thing. But every day would walk to the park and h But we were off it was Christmas, but we had started this script, and I just remember thinking as soon as we started writing it, because it was really the lowest point of my professional life, and I really did start thinking about what else how to keep this thing going. But then as soon as we started writing the script, I started just feeling better. I started being able to walk quicker instead of like just slugging it out walking through the park, you know, in the snow, I was able to kind of like march through the park, and Dave was way on vacation, and I would go through Central Park and go to our office and I would work on the script and I would send him whatever pages I did, and then he would work on it when he got back to his like wherever he was, and send me stuff. By the morning, I would have stuff from him. And I remember just working on it over this period of time and knowing, Okay, I think this might be the thing. And to talk about risks so in what you're supposed to do in the TV business. And even though we were unhirable according to the film agents, we did have a couple people in TV at television companies who would have heard a pitch from us and paid us some fee to write a script if they were interested in it. And our agent said, if you are working on something and you want us to get you in those rooms, even though you're cold, you know, the traditional thing is go pitch it. If nobody wants to pitch, they're not going to want the project, and you're going to save yourself time. Otherwise you're going to spend four or five months writing this script on spec, and the great likelihood is nobody is going to want it, and you will have wasted the time and the opportunity costs to find a way to be in business with these people, and they will. You will make some money over this time and now you'll make no money over this time period. But what David and I realized was if we wrote the script, and we wrote the first episode with andrewros Orkintwo was three of us. But Andrew was willing to go along with this idea, which was, well, write it on spec. Yes, it's possible. In fact, it's likely that nobody will want it. But the only way a writer in Hollywood can grab any power and control their future in any way is to have a piece of material that the business wants, because then you can set terms instead of having to de facto take their terms. And so we decided we're going to write it on spec so that we can create an inflection point. If somebody wants it, we can say, well, then you have to set a start date that you're going to make the show, that you have to be willing to give us the script back by this date. If you won't, we could gain momentum and kind of flip the paradigm, and we decided that that was a risk worth taking because of the asymmetrical upside, and so we did that and luckily, this wherelock comes in, like we had something that had the thing in it that made it the right thing at that time, so that all just added up in the right way, so that somebody did want it badly enough that we could set a situation up where we could put ourselves in a position to really succeed with it.

That's amazing And in some ways I love the symmetry right where the beginning of your career and this particular point which has brought you to where you are today, there are some symmetries despite the fact that you're now you know, older, wiser, more mature, etc. But that thinking and that risk calculus, it has served you well.

It's also about telling the truth to yourself. So like, yes, the agent said that to us undeniably, even though it sounds apocryphal, but it's true. I mean, I've all the email backup. But also at other times in one's life you could ignore it we had made because you look at me kind of incredulously, but we yes, I was incredulous about the fact that you mean this twenty year career of constantly making stuff that people want to make and see, like, you know, we had done all sorts of written Ocean's thirteen by them, it didn't matter. The business doesn't care. And it's a great thing to know that the business doesn't care. And so you have to make the business care. You have to create something undeniable, and you have to create a piece of work that is undeniable. Like your mother said, it's unfair. It's okay, it doesn't mean yet that's the state of play, is that it's unfair.

Yeah, I know. It's the same thing in you know, the written realm, even though it's much more fair I think the than Hollywood. And we'll talk about this in a second, but you're only as good as your last book in terms of the advance you can get and like how people will listen to you. And I always know this when I'm working on my next book, I'm like, shit, if this book bombs, then I'm not going to be able to sell the next one. It doesn't matter that I've had three New York Times bestsellers. If the fourth one is a bomb, you know, like.

I have a question that I haven't heard Nate ask you yet, or haven't heard somebody ask you and if they have, So you were in one of the best positions a human who wants to be a writer can be in, which is you were at the New Yorker. That's not something anybody ever kind of like cast aside in any way, meaning if you can say to somebody, I'm on staff writer at the New York No, no, no, the access that that gives you and the sense of security of like Harvard, I'm at the New York I lost.

My New Yorker email last year, Brian, I had a Maria Kondacove at New Yorker dot com email address that I no longer have and I wasn't even warned that they were going to take it away all of a sudden, I couldn't log into it. Really, yes, really, but I haven't written for them for years, so, like, I totally understand it.

Were you worried about that?

Though? No, no, it was No.

I don't mean about losing the email address. I mean were you worried about kind.

Of like sure, I went on book leave because in order to write the biggest bluff my last book. I had to immerse myself in that world one hundred percent. There was no other way it was going to work. I could just you know, stay at the New Yar, like do my weekly thing that I was doing, plus you know, learn poker and be able to do this, you know, understand this world. And so I kind of I made that calculated choice. And then you know, one thing led to another and I realized, you know, there are other things I want to be doing, and what am I happiest doing? That was also a question I asked myself, right, and I realized that longer for me is happier. So I'm happiest when I get to immerse myself in a book where I get to be in that world for a long time.

You know what, something we didn't talk about because what you know, so I have to vote a lot of time the last five years to songwriting, and I h it's amazing.

I follow you on Instagram.

Yeah, once in a while I'll say something, but like I don't know, like sort of how that I At a certain point I started writing songs. I wanted other people to hear them, and I made a decision like I don't five years ago I was like, I'm gonna write with people, and I love like Guy Clark in Town Van Zanne. I love country music broadly. I'll say folk music songs that have stories in them that that's the kind of consonance with what I normally do. I come from a musical background, you know. My first career was as an an R person producer, record producer. I've always been around it, but a number of years ago I started really taking it seriously and I decided I'm going to devote time, like I'm going to devote a day a week at least to working on songwriting, making relationships with people in that business, going to Nashville, trying to write songs with people down there with an eye toward getting some artists to sing those songs. That's like really intense use of time and also at up time, and and like the constant risk of humiliation of rejection. You know, it's like if you want to do anything, that's like you're just going to deal with rejection. And even though one gets much better at understanding rejection for what it is, it's a complete lie to say like rejection doesn't sting. It's the only difference is it stings as opposed to it, like, you know, knocking you out, but a jab still hurts.

Right.

It's no longer a right cross or an upper cut, but a jab is still like, oh, that was not fun. I didn't want to get hit in the face. But like, I just and I've thought about it a lot, like what why? What made me keep me going? Because I had off the bat. A couple of people were like, oh, well that's a good song like come, but I had I could stack up the rejections and it just this year, finally, now there's an album coming out A really big country artist named Jackson Deine caught a song that co wrote and that I co wrote. And I've had a bunch of songs get cut by people, but this is the first, like and people artists who meant a lot to me, where it was like a really big deal to me, But this is like a song getting cut by somebody who's a really big deal and they just you know, he just put out the track listing and I know that this songs on the record. We wrote it together and congratulations, thanks, But it was I cannot tell you the amount of time, just hours, days, energy, focus, heart and all mostly where the writing of the songs feels really great, but the rest of it felt really bad. But I've just learned to chase This is to the point of like the curiosity something about something about the form of that particular kind of songwriting is hard in a way that's like poker. That's that draws me to wanting to solve it. It's not really solvable, but it's an artist the same kind of artistic spark that happens when I want to and this dialogue. It's the same sort of idea of writing, but the form is strict and you have to find a way to satisfy a bunch of different things. And it drew me to even though there wasn't gonna be really money in it. There was just going to be a time suck and I will pay. And people in my life really supported it and wanted me to do it as as now it's gonna and I know it'll look Whenever we all look at someone doing something where it's like, oh, that person, how did they go from that? It always looks in the outside like God, they that person must be that must be like a lot of talent, or that must be like that's an amazing connection. Or that must and almost always it's just like they were willing to risk failure and they were willing to try really really really hard, and they're ring the most out of like a talent that might not actually be greater than someone else is. It's just like the willingness to look ridiculous and the willingness to fall on your face and the willingness to feel bad because you're called to do it, and you stack those things. You're aware of it, especially as you get older. I was aware of it, and I am aware of it, and it's just like a problem that I'm drawn to. And that's the hallmark for all the things. And that goes back to the thing I started with about self knowledge. It's like the greater risk for me is not doing those things because I'll feel bad and I won't I won't feel like I could answer the questions. You have a good day, honestly because I didn't chase those I didn't listen to that spark. But I have to listen to it. I have. That's why I do morning pages, meditate because that stuff surfaces. You want to write songs, Go do it, take the risk. What's the worst that happens? Is you hear know a lot? Okay, you'll hear no and you'll try again.

Yeah. Well I have many more questions, but I think that that is just such a beautiful place to end, so I could. I couldn't have thought of a better way to put it. Thank you so much for coming on, Brian. It's been such a pleasure.

Maria, It's my pleasure.

Thanks.

Risky Business is hosted by me Maria Kannakova and me Mate Silver. The show is a co production of Pushkin Industries and iHeartMedia. This episode was produced by Isabelle Carter. Our associate producer is Gabriel Hunter Chang. Our executive producer is Jacob Goldstein. And if you want to listen to an AD free version, sign up for Pushkin Plus.

For six seventy nine a month.

You get access to ad free listening. Thanks for tuning in only f

Risky Business with Nate Silver and Maria Konnikova

Risky Business is a weekly podcast about making better decisions. The hosts, Maria Konnikova and Nat 
Social links
Follow podcast
Recent clips
Browse 49 clip(s)