#98 Brian Koppelman

Brian Koppelman (@BrianKoppelman) is back! He joined James in episode #59 and in this one they  talk about getting over your creative hurdle, the value of good partner, and how easy it is to find success.

Koppelman is no podcast newbie either, he has his own show – The Moment – which has featured guests like Altucher, Seth Meyers, and Phil Hellmuth.

Their interview begins with a short discussion about how podcasting is a different sort of interview. They comment that no one would watch them sit in a room and talk, but there’s something about the mic, your speakers or headphones, and the captive nature of podcasts that’s different. Koppelman wrote about an example of this when Jim Breuer was interview by Mark Maron on his WTF podcast. It’s a good article. Really good and I don’t care for Breuer, Maron, or SNL but read the entire thing.

In Wired, Roman Mars (another great podcaster) said “It’s weird, but I love the closeness that people feel to me and to my show. Public radio once cornered the market on the closeness. Listening to NPR became the definition of who you were. And podcasting is a hundredfold more intense than that. Podcast listeners are so, so dedicated.”

Gary Vaynerchuk suggested something similar, but in regards to marketing channels. When Koppelman does his Vine videos, Vaynerchuk would probably applaud what Koppelman is doing. The videos are short and inspirational and appeal to people in a way that an article, a longer video, or even his podcast episodes can’t. It’s like a coach bringing a player over the bench, offering a few encouraging words, and then sending them back out there. It’s all about matching the medium and the message. Podcasting is still so new though, that there’s a lot to figure out.

For one thing, it’s not a quick way to make a buck. “It isn’t clear that there’s real money in it.” Koppelman says about podcasting. Jason Calacanis (episode #77) has been there, done that. He told James he tried to start a network and it doesn’t really work. He found that you need people with established bases, fans, skills and those people don’t want to work for anyone.

But Koppelman and James continue at it and begin talking about Solitary Man, about which Koppelman say, “that’s the movie of ours that means the most to me.” In part because he was stuck on it for so long. It took over three and a half years to write and another year and a half to get funding.

Part of that struggle was because Koppelman got stuck writing part of it and had a brief interlude as a stand-up comedian. I couldn’t help but that think that part of this was advice from Koppelman’s writing partner David Levien (episode #85) who told James, “when you’re doing something creative, you have to find different ways to stay fresh.”

And each iteration, each adventure, each small story is part of the bigger one. Koppelman reminds feeling that if he didn’t do something, he’d never do it. “When you’re thirty you do think to yourself, if I were going to do it, I probably would have” he says. Carol Leifer (episode #66) thought something similar when she had a chance for her own show. She had written on Seinfeld, on SNL, and for the Emmy awards. This. Was. It. Her own show! But it wasn’t. In her book she tells the story of Jerry Seinfeld coming over during filming for the pilot and saying:

“You know, there’s not just one thing, Carol. Take the pressure off yourself. It feels like the most important night of your life , but it’s really just another night in the bigger picture of everything you do. Now, go have fun out there .”

Each thing you do is just another fence post in the work of life, and that never ends. Koppelman said that you have to “keep moving forward, it’s always scary.” This is another theme the podcasts guests have hit on, success isn’t a destination but more like a mindset. You don’t arrive, land, or end-up successful. You “keep moving forward.”

Stand-up began a change within Koppelman, partly because he was surround with good people. “There’s an incredible power in having a creative partner” he tells James.  Adam Carolla (episode #25) met Jimmy Kimmel and thought “hey, this guy’s funny” and “we work well together.”

Solitary Man continued to be Koppelman’s white whale. As he trawlled through comedy clubs, the project swam untamed. Not finishing it made him feel like “a fraud.”

To break through the creative block he tried The Artist’s Way, but was stymied. He needed stand-up because it “could let me fail in a certain way.” He had to build up a set of skills and “pass a club” and slowly his fear abated. His fear of failing was melted away by the warm stage lights. Gretchen Rubin (episode #97) told James that repetitive actions like this can “dampen our emotional reaction to things.”

Ready to face his fears, Koppelman began writing and let his rough draft be rough. Jacques Barzun wrote, “let that first sentence be as stupid as it wishes.” But not forever so. Koppelman advocates for a band, a range, of creativity to fall in. You want to be vulnerable early and write anything, no matter how bad. But you need to be tough later on and welcome feedback that might rip it apart. It’s been these landings, between soft as cotton and hard as stone that the really good work is found.

Koppelman said he cranked away at the script and one day on the bus he realized what the missing part of the movie was. He said he rushed into his office and told Levien “I need five minutes” and he transcribed what he had written. Ryan Holiday (episode #18) mentioned something similar, saying he would finish a run and walk into his home, telling no one to bother him while he jotted down an idea.

Once the script was done, it was time to make the movie. Slowly. Koppelman faced resistance from the studios about the tone of the story and age of the characters. To combat this he had custom shoes made that reminded him he had to take one step each day to get the movie made. Doing one thing, no matter how small, was something Jack Canfield (episode #90) said he proposes too (though he suggests five).Slowly Koppelman’s movie got reeled in. Steven Soderbergh thought it was good. Michael Douglas agreed to star. But it took over a year to get the money.

James asks what is becoming his stock, but wonderfully open, question; “what would you tell someone who’s listening and sitting in their cubicle?”

Koppelman doesn’t disappointment and sounds excited to give five pieces of advice:

  1. Have good people in your life. “I luckily married the perfect person for me.” he tells James. Tom Shadyac (episode #15) said that he worked well with Jim Carrey because they each made each other better.
  2. Ask what you want. “What is most important to you?” he tells James. I’m guessing he got this from Tony Robbins, which means that Jairek Robbins probably got it from him when he told James that people need to learn what they want in life.
  3. Be selfish. If you don’t have a good dream, Koppelman says, “you become toxic.” This is what Scott Adams calls the right kind of selfishness. One that makes you and everyone around you better.
  4. Say no. “I cut it all out of my life years ago.” Koppelman tells James. There’s no obligations that don’t bring him good feelings.
  5. Don’t listen to experts. Experts don’t have the incentive to find a gold in the river, it’s to make sure the pan doesn’t get full of stones. Stephen Dubner (episode #20) used a soccer metaphor to explain why you should act toward your real interests, not perceived ones.

James follows up with another good question, but how do you know when to quit, when you won’t make it. “The line between being an artist and being delusional is very thin.” Koppelman says. Stephen King has his own suggestion:

The biggest part of writing successfully is being talented, and in the context of marketing, the only bad writer is one who doesn’t get paid. If you’re not talented, you won’t succeed. And if you’re not succeeding, you should know when to quit. When is that? I don’t know. It’s different for each writer. Not after six rejection slips, certainly, nor after sixty. But after six hundred? Maybe. After six thousand? My friend, after six thousand pinks, it’s time you tried painting or computer programming. Further, almost every aspiring writer knows when he is getting warmer – you start getting little jotted notes on your rejection slips, or personal letters . . . maybe a commiserating phone call.

Instead of making it as a writer, entrepreneur, spouse, think about pivoting. Jack Canfield told James that he sees all kinds of people succeed in areas related to, but exactly what they dreamed of. Sam Shank (episode #78) lived this when he pivoted from Hollywood to start ups.

In the end Koppelman offered this advice:

“I knew that those two hours in the morning that Dave and I were writing Rounders, were the two hours that I felt most alive in my workday. And it wasn’t a bullshit thing that lasted one day, even when the writing was hard, the actual doing of it is hard…and I wanted that all the time.”  about it feeling good even though it was hard.

And that it was hard matters a great deal. “You have to cover that difficult terrain yourself.” Koppelman says. Jairek Robbins said the same thing, that his dad could have saved him some time and money but without learning on his own he would be short the lesson.


Beyond their enjoyment of podcasting, Koppelman also has a Vine channel,  #319 is quite popular.

“I’m sure there are days when you think the haters are right and you’re not good enough. Days you know it’d be easier to quit. But then you’ll never know what would have happened if you gave it one more push.” – Brian Koppelman

Nassim Taleb calls this the sandpile effect, and it’s a key part of his theories of non-linearity. Imagine you are building a sandcastle (Taleb is “on a beach in Copacabana, in Rio de Janeiro”) but you can be anywhere. One bucket at a time, you add to the castle. Until finally one bucket is one bucket too many, and the whole thing topples.

Taleb’s point is that in life, sometimes that last bucket is random. His example in Fooled by Randomness – appropriately enough – centers on an actor who gets selected for a role and then another role because of the first and so on. That initial selection,the one more push that Koppelman says, or last bucket that Taleb dabbles with could be random. Research has shown that judges can be predicted to be more or less lenient based on their eating habits.

Koppelman likes the Vine videos because of how loose and free they are. A decade ago Jason Calacanis thought this unedited nature was unprofessional but he quickly saw that this was exactly what appealed to people. Maria Popova (episode #89) told James that “allowing yourself the uncomfortable luxury of changing your mind” is one of the things she’s learned running Brain Pickings.

Koppelman’s current project is Billions, which is starting up production now. You can see all the Variety tags for more. He also Vines from the set.

Koppelman wraps the interview telling James that it’s okay to hear people tell you to chase your dreams but that “you have to work ferociously hard.” This is theme of our April 2015 book club choice, So Good They Can’t Ignore You. For example, do you know how Steve Martin became so funny?

He was born that way, no that’s not it. He was passionate and used the law of attraction to will success to him. Wait, wait, that’s not it either.

Martin got a job at Disneyland and spent his summers doing tricks. Then he worked on his magic which transitioned to comedy. But being a Grammy Award winning banjo player, that was a gift right? No. No. No. He played banjo records at half their normal speed so he could play along with the song. Success takes work, super success takes super work.

Dave Grohl also has a bit of wisdom:


Koppelman was on Seth Meyer’s show, you can watch the clip below.

Thanks for reading. If I messed up something other than writing “vine channel” please let me know via text, (559) 464-5393, contact, comments or @mikedariano. There was one great bit that didn’t seem to fit. It was around 33:00 when Koppelman talked about learning comedy. He says that he had to learn to “be mean enough to dispense with the heckler without losing the rest of the audience.”

This shows how deeply he had to understand the craft to do it well and he estimates that it would have taken years and years of late night shows and touring to be able to earn a living from it. To succeed you have to understand things deeply. Jason Calacanis said you have to “know this stuff cold.”

It’s ironic that a post featuring a Michael Douglas movie would lead to another Michael Douglas movie – Falling Down – which is an extreme example of the straw that broke the camel’s back.

*A previous version of this post misspelled Jim Carrey’s name. 

31 thoughts on “#98 Brian Koppelman”

  1. […] Brian Koppelman said that he had to work on Solitary Man everyday. If he didn’t then it would feel to him like he wasn’t moving the project forward. Even if it was something small, he did it. (Koppelman went so far as to write on his shoes as a reminder). […]


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