"No matter what your age or your life path, whether making art is your career or your hobby or your dream, it is not too late or too egotistical or too selfish or too silly to work on your creativity."

-- Julia Cameron

Brian Koppelman's career as a filmmaker is like his first movie; Rounders. He wins with good hands. He loses with bad hands. He loses with good hands too. He bellies up to the table, gets a break, and shows up the next day.

Life, wrote Scott Adams, is like "A reverse casino. In a casino, if you gamble long enough, you're certainly going to lose. But in the real world, where the only thing you're gambling is, say, your time or your embarrassment, then the more stuff you do, the more you give luck a chance to find you."

Koppelman was the guy that studied poker odds and won a big pot. He worked on Rounders, Knockaround Guys, and The Illusionist. Then he lost or broke even on a bunch of hands. In a sense that's all that could have happened when you finish a movie like Oceans 13 which starred Matt Damon, Brad Pitt, and George Clooney. When Runner Runner came out, Koppelman told his friends not to see it. When his role on the television show Vinyl fell through he was gobsmacked. When he gets stuck writing Solitary Man he gets really stuck.

Then, he starts Six Second Screenwriting Lessons on Vine. He starts podcasting. He starts writing Billions.

Koppelman's film career mirrors a successful poker career. Don't blow up. Play games you can win. Get back to the table. Ditto for how Billionaires make actual billions. Just like financial capital, Koppelman has compounded career capital due to small investments; in projects and with people.

David Levien is Koppelman's best friend (since he was fourteen). He's a crucial supporting character here. Part of the reason this is about Koppelman and not both is because Koppelman puts out so much material while Levien does less. Ditto for Amy Koppelman. Brian gives her a lot of credit for the initial nudge and continuing support. When asked for advice, Brian's first suggestion is to marry someone who supports you.

Brian Koppelman will be our subject but he hasn't done it on his own.

One programming note; all unattributed quotes are from Brian Koppelman.

Ready?


Career Timeline

1998 - Rounders

2001 - Knockaround Guys

2003 - Runaway Jury

2003 - The Street Lawyer

2004 - Walking Tall

2005 - Tilt

2006 - The Illusionist

2007 - Ocean's Thirteen

2009 - The Girlfriend Experience

2009 - Solitary Man

2013 - Runner Runner

2013 - Vine series, Six Second Screenwriting Lessons

2014 - The Moment podcast

2016 - Billions S1

2007 - Billions S2

2018 - Billions S3  


Table of Contents

Career Timeline

Introduction

Awaken the Artist Within

Writing Rounders

Middle Movies

Solitary Man, on screen and on stage

Runner Runner

Vining and Podcasting

Billions

Career conversation

Reading List

Sources


Introduction

This research began with Billions but can't start there. Like personal finance, career capital is made one moment at a time. Koppelman’s story for us begins in 1996 and he’s about to turn thirty. He has a young child. He's making good money, enough to buy dinner for friends. But, something's not right in his life.

Koppelman describes his situation as toxic. If you aren't the kind of person you want to be to yourself, you won't be the kind of person you want to be to others either. Koppelman started smoking at twenty-nine years old. "Who starts smoking at twenty-nine?" he admonishes his younger self.

Though he has some financial success, his career isn't what he'd hoped. "I remember sitting in my office, smoking a cigarette. I was fat and miserable. (Musical) Artists were calling me from the stores they were playing in because no records were there." Koppelman made promises he couldn't keep and felt awful. Our thirty-year-old protagonist looks in the mirror and sees an overweight smoker who doesn't like his job and isn't the hero he wants his son to see.

"Change happens when the pain of staying the same is greater than the pain of change."

-- Tony Robbins

Awaken the Artist Within

Koppelman's wife Amy planned a birthday party. First it's family and friends then it's friends and poker.

Getting married young, to the right person, "that's just luck, largely luck." How so? "When I was thirty and completely miserable with my life, Amy my wife, completely cleared out the storage area under where we lived and said, 'You're going to do this. I'm gonna handle this first year of Sammy's life. If you have to write in the morning and go to work and then go out and research - you can do this.'"

Amy clears the slate and David gifts a book, The Artist's Way by Julia Cameron. Brian also reads the Tony Robbins book, Awaken The Giant Within. These confluences become a rallying point.

"David gave me The Artist Way and said, 'this will help you get unblocked.'"

"The Artist's Way by Julia Cameron was enormous for me. In doing morning pages, I freed myself from all this other stuff, from the curse of perfectionism."

"My first child was born and I wanted to be the kind of dad to tell his kid to chase his dreams, to do anything, and I realized I wasn't. Tony's book (Awaken the Giant Within) kind of throws the gauntlet at you. If you aren't living the life you want, why not and how can you?"

The books and storage space work reframed how Koppelman viewed the world. He believed people were born with talent. "I saw classmates get singled out for their abilities...I would think they were funny from birth."

Divine creativity is an easy story to tell and digest. IDEO marketing head, Tom Kelley, tries to teach people creativity. Most people think creativity is something you are or you aren't. Most people think creativity is like height. Most people don't realize creativity is like hair color, with some work you can change it. Kelley knows this because Kelley was one of those kids. He thought people were naturally talented. This is what he advises people:

"Of course you can't draw if you haven't taken drawing lessons. You can't play the piano either. Who thinks you can play Mozart's concerto without taking piano lessons? Nobody. Drawing is the same way."

Koppelman switched his view of the world from; you are the thing - to - you become the thing. During this time he also concludes, there's no such thing as experts.

And with hindsight this lesson was obvious.

"In the music business, I watched experts be wrong over and over again. That taught me there's a value in listening to the experts, hearing their reasons and dispassionately evaluating the reasons."

Before his thirtieth birthday, Koppelman worked in the record business. His first major signing was Tracy Chapman. He noticed her because he was involved in the South African divestment movement and wanted folk singers for some rallies.

He asked her to sign a record contract. She said no. He asked record labels to sign her. They told him no. Why, he asked. She won't sell they said. Eventually Chapman signed with Koppelman and eventually a record company took the plunge but not before Koppelman learned a lesson.

"I realized the experts don't know any better than I do. They're all scared and when something touches that special place in them their instinct is to run from it."

This makes sense he reflected.

"In the short term, gatekeepers and experts only get fired for a wrong Yes. A wrong No takes a long time to come down against them."

It's the difference between owners and employees. Owners are incentivized to think about the long-term health of the business. Employees are incentivized to think about the near-term health of their career. Here's how Rory Sutherland of Ogilvy and Maher explains the lesson Koppelman learned:

"There are lots of cases where you need to signal something, by making a decision - and it may be the rationality of the decision - actually prevents you from making a better decision. If I pretend everything is logical, it may not be a really good decision but if things go wrong no one can blame me, is an extraordinary form of corporate insurance."

It dawned on Koppelman there were two kinds of feedback and led to him "dispassionately evaluating the reasons."

It's with this view of experts that Koppelman and Levien begin to write Rounders even though Koppelman wasn't a writer -- yet.

"I believed if you did the work you were the thing and as soon as I believed that my life changed."

Morning pages and skepticism of experts kept him moving forward. He was also about to catch a big break.

Writing Rounders

In that basement storage room with one chair, David and Brian start to write Rounders. "We had a stack of books that were about poker and the language of the game and at night we'd go to these games and collect data." Six days a week, two hours a day, the duo would write.

Brian would get up, write for two hours, go to work, go home, and maybe go out to the poker clubs for more research. This wasn't ‘research' it was RESEARCH. "I didn't go out drinking," Koppelman explains. Deep research - like the fleece vests in Billions - is a foundation for Koppelman's and Levien's work.

What they explicitly knew or implicitly stumbled upon was an insular world. "I've always loved insular groups of people with their own languages, signals, symbiotics, and ways of communicating and being." At the poker clubs, they toiled to learn the language, the nicknames, and the stories.

They also used pieces of their life. Koppelman had attended law school but never practiced. However, one day while walking past Fordham his wife said, "but that character in Rounders never would have shown up if you hadn't met that professor at law school."

With background details from underground poker scenes and law school, the duo was ready to sell their script. Every studio passed. But, like his experience with Chapman, it makes sense why. Employees tend to think like careerists. Years later Koppelman advised:

"You know, as the person doing the thing, it's very hard for it not to be wounding because when you invest so much in creating it's very hard...It's easy to believe their judgment is right because on her business card it says vice president...But most of the time they don't fucking know."

Miramax eventually buys it. John Dahl directs it. Now, Dahl could have been another gatekeeper. He could have been another so-and-so title on a business card. But he's not and he teaches Koppelman another lesson.

Originally the script had Phil Hellmuth in the role that would go to Johnny Chan. Koppelman had written it this way because he once shared a table with Hellmuth. Dahl suggests they change it.

 "At first I wanted to say ‘No' but then Dave and I went away and tried it. Which I think all writers, all creators...should try. Because our ego is inextricably invested in our work, our initial reaction is often anger and it crowds our thinking."

The movie worked better Dahl's way. Koppelman reflected, "If you can train yourself to take the constructive criticism in, and go away and wait until you're calm and dispassionately look at it you will be able to make a better quality decision."

Koppelman's calm and dispassionate version shows up twenty-four hours later. This is part of a game he plays with himself. He has to believe he's capable - and successful - in writing the greatest thing ever. Each stacked page is the greatest thing since sliced bread. His actors wear outfits to fit their characters, and this brief confidence is the writer's wardrobe.

Koppelman also learned how to work well with others on a set.

"John Dahl is an incredible senior officer. As director of the film he could have insisted, but he did the opposite. He said, ‘Why don't you guys try it?' We went back and we did it and it was immediately clear to us that it was the right choice."  

"During the watching of the movie it was so clear that showing Mike's hole cards was better, even though the scores were identical (from the audience) we agreed with John."  

With a well-researched script, a generous director, and Matt Damon, Rounders catches a lucky break; the poker boom. With hindsight, it's apparent that the hole card camera, Chris Moneymaker's success, and unregulated online websites all helped poker enter the collective conscious. Sometimes it's better to be lucky than good.

He followed Steven Pressfield's advice to "put your ass where your heart wants to be." Koppelman made it! Maybe.

Middle Movies

Professor Cal Newport has a theory called career capital that states; rare and valuable jobs require rare and valuable skills. Great teachers choose their district. Great coders work from home. Brian Koppelman now has career capital and writes, directs, and produces movies.

Through 2007, Koppelman participated in Knockaround Guys, Runaway Jury, The Street Lawyer, Walking Tall, Tilt, The Illusionist, and Ocean's Thirteen. For some projects, he and Levien punched up the script over a month. For other projects, he was committed.

Koppelman continued to do a lot of research. Even though he had made Rounders, he still heard ‘No' a lot. "If you trust your own R&D, it will give you tremendous strength when you come up against the monolith." Like when selling a movie set in the 1800's about an Austrian magician. Koppelman and Levien produced that movie, The Illusionist, in which Paul Giamatti co-starred.

They also make Knockaround Guys. Brian knew it wouldn't be huge, but for some people, it would be great. That was okay for him. A great niche movie is better than that a shit wide release.

Koppelman has spent the last dozen years making movies. He's done well professionally. Yet, careers aren't up and to the right. Nothing is. He's about to enter a career trough.

Solitary Man, on screen and on stage

In Solitary Man, Michael Douglas's character tells his daughter not to call him ‘dad' in public because it's harder to pick up women. Koppelman saw this happen to a friend, and "I went home and wrote twenty pages out of anger."

He showed the script to Dave, who told him that he had to write this one solo. Koppelman worked on it in his free time, but he got stuck. During this time he also tried stand-up comedy. It was a way to face his fear.

These projects were cathartic. They were challenges to Koppelman from himself. Can you write this movie? Can you last on stage?

With practice, Koppelman's standup routine became good enough. One-third of the nights his jokes bomb, one-third of the nights his jokes land, one-third of the nights his jokes kill. In much the same way that jokes get tested, refined, tweaked, adapted and a comedian will stumble upon the solution, Koppelman unclogged his Solitary Man script

"I sent it to a friend of mine and he said, ‘What are you planning to do?' I mentioned why I was stuck, that there's this one thing that should happen, and he said, ‘Here's why that shouldn't happen.' As soon as he said that I had a eureka moment and I wrote the rest of it in three weeks."

In another interview, Koppelman says the eureka moment happened on a crosstown bus and "I wrote it down in a little black notebook I always carry with me." For those curious, it was the return the shirt scene.

With a finished script, Koppelman just needed to talk to the gatekeepers - again. One told him the movie couldn't be made because of a foreign rights contract issue. "So I looked into how foreign sales are done," and Koppelman did the work on it.

Koppelman is still figuring things out. That do your own R&D mentality was expressed in his preparation for the 2018 Masters golf tournament. “I’m going to prepare enough to defend myself from my own insecurity.”

Solitary Man was a mostly typical movie shoot. We'll only point out the last scene.

"I remember standing there with Soderberg who produced the movie and got Michael Douglas. He said 'You're going to have a huge, instinctive pull to protect yourself and shoot an ending that's different. You're going to want to cover, do not shoot another ending because if you shoot another ending someone is going to force you to use it. Don't do it.' I remember being there on the day and the assistant director coming up and going, 'Do you guys just want to  have him do another?' And my insecurity rose up and I almost did it and Levien said 'No fucking way.'"  

We are excellent planners in the abstract. Back seat drivers know it all. Monday morning quarterbacks are brilliant. Stock market commentators never lose money, and so on and so on. What works better than hindsight *I told you so* is foresight and design.

Koppelman was fortunate that Levien stepped in but there are ways he could have designed a way around that situation. He could have written a letter before shooting. He could have had Soderberg call. He could not have been on set at that moment.

Psychologists like Daniel Kahneman refer to our brain as having two parts; System 1 and System 2. Writers like Maria Popova characterize it a bit more; John Watson and Sherlock Holmes. Whatever the analogy, our long-term hopes and short-term choices don't always align. Koppelman understood this when he committed to two hours, six days a week in the storage space with one chair. He underestimated this during the final scene of Solitary Man.

Koppelman controlled Solitary Man (mostly) from the first word to the final scene. Runner Runner he did not.

Runner Runner

The movie premise, from Rotten Tomatoes: "Richie, a Princeton college student who pays for school with online gambling, bottoms out and travels to Costa Rica to confront the on-line mastermind, Ivan, whom he believes has swindled him. Ivan sees a kindred spirit in Richie and brings the younger man into his operation. When the stakes get incredibly high and dangerous, and Richie comes to fully understand the deviousness of his new boss, he tries to turn the tables on him."

The score, from Rotten Tomatoes: eight-percent fresh.

Koppelman didn't promote it, to anyone, not even his friends. Runner Runner was "the lowest point in my career." But in the depths were lessons.

First, it reinforced the idea of alignment and additive crew. Koppelman and Levien are aligned with each other. "We are both keenly grateful for what the other person brings." It's the same thing with the actors. When one interviewer asked about the kind of look Damian Lewis gave during one scene in Billions, Koppelman notes that, no, he doesn't write that. That kind of thing is what you hope the actors will add.

Second, Runner Runner proved, "you get in trouble when you sell things in advance." This lesson they got twice. "The lesson we learned from a bunch of television experiences was, we would not sell a pitch. We would write a script on spec and they would have to say they would make it or not."

Like a short stack in poker, Koppelman's career stack is down. But career stacks based on skill and luck, and worrying about luck is a waste of time. "Instead of sitting around and saying ‘the movie business won't hire me, the television business just fired me,' instead what I could say was, ‘we just wrote three pages today, tomorrow we're going to write seven pages."

Vining and Podcasting

Koppelman's first Vine - the six-second videos - was, "All screenwriting books are bullshit. All. Watch movies.Read screenplays. Let them be your guide." Later he would confess that the Vines weren't so much for the viewers as the producer, himself. "Those Vines were me talking to myself, reminding myself of the core values."

Around this same time, he started a podcast. The first guest was Seth Meyers but the roll would expand to include Gabrielle Hamilton, Seth Godin, and Dave Ramsey. Kind of a hodgepodge? Yep. "I will only have guests on my podcast If I love their work, if I love their story, or if I'm incredibly interested in some moment of their journey."

Again, we see curiosity entangling Koppelman's work. Why?Because curiosity leads to interesting moments which unearth the insular groups that Koppelman loves.

Being a podcaster also exposed him to new stories and made him a better listener. But this took effort. "I had to work myself into a posture of being ready to listen."

While writing the spec script for Billions, podcasting, and vining, Koppelman also walked.

"What do I do every day to keep myself in the creative space? I journal, I meditate, I take long walks."

Walking may be the simplest and soundest act of creativity. David Benioff, who Koppelman calls one of today's best novelist, got his idea for City of Thieves while on a walk. When he was younger - and able - Stephen King walked four miles every day. Beethoven, Kierkegaard, and Dickens all walked for inspiration and perspiration. Cal Newport, our career capital developer, calls a good walk "active meditation."

In his book, Where Good Ideas Come From, Steven Johnson wrote: "The history of innovation is replete with stories of good ideas that occurred to people while they were out on a stroll."

Each walk through Central Park. Each morning page. Each meditation session. Each person who stood beside and behind him, all of these things help make Brian Koppelman make Billions.

Billions

Billions started with a bit of serendipity. Co-Creator Andrew Ross Sorkin had the same agent who connected him with Koppelman and Levien. Like Rounders being part of the poker boom, Billions took root within a certain ecosystem. "About the same time we started to get interested in the hedge fund world," said Levien, "we found our interest drawn to premium cable, the twelve episode seasonal dramas." And, Koppelman, wondered, why do we revere entrepreneurs.  "Most Americans will give you a break and wear a t-shirt with your picture on it. Why is that?"

With premium cable as the distribution and hedge funds and courtrooms as the settings, Koppelman and Levien write the pilot on spec.

In the same way they'd developed as writers they'd also developed as professionals. They wanted to create something that would get made. When you take this risk, said Koppelman, "All you're risking is time and ego."  

In a conversation with Koppelman, fellow screenwriter John August explained writing opportunities much like investors describe stocks. August asks, can I do this and will it succeed? Investors ask, is this in my circle of competence and will I make money? Thus began the research. "You want to communicate the (show's) themes in every way," said Levien, "from the way a car pulls out through the way the actors perform."

Billions is not a documentary. It's "Realistic but with heightened drama." How do you get to this point?

"We read a lot, spoke to a lot of people, visited a lot of places. When you hear stories about why people wear fleece — that they are proud of not dressing the way folks on Wall Street dress — that's an indicator of the way hedge funders think about themselves. We like figuring out the little signs and customs of an insular world so we can then put those on display for a larger world."

One interview was a dinner at their favorite restaurant but at the last minute, the hedge fund manager changed it. It was the guy's ‘usual' place and there he ordered what he ‘usually' drinks. It was expensive.

Reflecting on the meal, the duo realized it was about power. Koppelman's research is like dissecting frogs in middle school. Everyone knows that frogs have hearts, lungs, and stomachs but no one is sure what it looks like. Only once you get inside do you get it. Koppelman saw things from the inside. "I've never thought about who's going to win dinner."

It wasn't only meals, conversations, and private planes. Koppelman and Levien are drawing from their career wells.

For The Girlfriend Experience, Koppelman and Levien interviewed high priced escorts. "At the ends of the interview we'd say, is there anything that might surprise us. Out of a hundred of them, 70 of them said the most powerful client I have is the one who wants to be dominated."

That made it in the show. So did "a moment between Wags and his analyst Ben Kim revolving around the delivery of food that Dave and I witnessed in a movie studio President's office seventeen years ago."  

Koppelman told Bill Simmons, "Billions is like an extension of all the stuff we've been writing about for twenty years."

What kind of truth syndrome do they use to get these stories? A mix of curiosity and empathy. "I'm in there to honor them...I'm not in there judging them. I'm in there with a posture to understand how everything works." We call them soft skills, but that listening muscle he's trained on the podcast he flexes in these interviews. "Who have you met that didn't want to be understood?"

Plus, people aren't all good or all bad. "The truth is, these people like all of us, are multi-faceted." Koppelman wants to write Yeah-But characters. This guy did this awful thing yeah, but he also donates to charity. This guy tried to stop Bad Guy #2 yeah, but he treats waiters like crap. Koppelman wants to write characters that "think they're in the right."

While Koppelman and Levien wrote the initial script they don't write every episode.

 

"It's up to the two of us to make sure the show sounds like the show. That may mean doing a dialogue pass on every script and keeping the lines that other people wrote that feel like the show and adding lines. But the way we found it best to get the writers to feel a sense of ownership is that if a writer on our staff starts a script, even if we've done work on the script, it's that writer's script and that writer's name goes on the script."

"In many ways," said Levien, "this show is a huge culmination for us." Circle back to their experience with John Dahl on Rounders. They're leading from the set of Billions in much the same way he led from the set of Rounders.

From the outside, it looks like a decentralized command structure. Hire good people and get out of their way.  

The Billions actors are "incredible, top flight professional actors and all you want is for them to take your characters and make them three dimensional." In another interview, Koppelman said, "I believe we have the finest cast of actors working on television today. These are people working at the very top of their game."

Koppelman wants gestalt scripts. "You write every line of dialogue they say but you hope the actors take something and make it additive - and our actors do."

On set, they'll do a table read. "If they (the actors) can't sell it at the table read it's my fault."

The goal is to make a good show. "We believe in the cardinal rule that David Chase would say to the writers on The Sopranos, which is that the most important thing is to be entertaining. We want the show to be entertaining, and we want it to allow you a range of emotions."

Career conversation

"If you do something great people will notice."  

But how do you do something great?

"If you want to be a screenwriter read a thousand screenplays and watch a thousand movies and then you will have a frame of reference for the work if you're honest enough with yourself."

Is there a shorter version?

"I've done the reps."

How do I get time for the reps?

"Say ‘No' to social obligations. I need that time."

Okay, so get to something great by getting the reps. What else?

"People often talk about following your dreams, you also have to work furiously hard." "Why do you have to be obsessed with it? Because this shit is hard to do"

If I do this will I break in?

"The truth is, if you're entering the arts there's no getting around this uncertainty. It's possible no one will ever give you permission so you have to give yourself permission to do the work. From a practical standpoint, just keep completing pieces of work. That's really the only thing you can do to feel a sense of progress."

Will this take long?

"It's been twenty years of sitting in a room, deciding to follow our own voice and finding a way to get that to the screen."

Reading List

"I read books by people who made work that I loved."

"I want information from people who aren't guessing, from people who came by information the hard way."

"You wanna read about writing? Then here's what you should do; memorize this, Conversations with Ernest Hemingway, The Big Picture by William Goldman, Kazan, Making Movies by Lumet, An Open Book, JFK, Show me the Magic, and The Films in My Life by Truffaut.

"Seth Godin’s The Dip is the best thing I've ever read about quitting."

"Here's a great book about the dedication and persistence required to become a working artist, Born Standing Up by Steve Martin."

"Joseph Campbell is a genius and his books are worth reading."

Koppelman shares much more on Twitter; @BrianKoppelman.

Sources

Koppelman is a good podcast host and guest and if you want more from him The Moment podcast is wonderful. In addition to that, I drew from; his three podcasts with James Altucher (including the one with David Levien), Koppelman on The Art of Manliness podcast, his video on YouTube with Dan Harris, his podcast with Tim Ferriss, his podcast with Marc Maron, his podcast with Patrick O’Shaughnessy, and his podcasts with Bill Simmons.