Amy Schumer

Amy Schumer (@AmySchumer) joined Brian Koppelman (@BrianKoppelman) on The Moment Podcast to talk about life as a female comedian. The interview was from January 2015 (no typo) and I missed it dropped. Luckily the episode was sent out again and I took some notes.

Before we begin, I have to note a problem on this blog. There’s too few women represented. In Antifragile Nassim Taleb notes that without the word “antifragile’ we miss half of – what Taleb calls “the interesting part” – life. My problem is bigger than that. I’m missing the female perspective.

I don’t feel compelled to write about women for gender reasons, but FOMO (fear of missing out). They know secrets to a good life. I read Ray Dalio’s Principles and was blown away. That’s a guy I have almost nothing in common with, but he taught me a lot.

I felt the same way reading Will Schwab’s The End of Your Life Book Club. That book made me a better person. Ditto for Man’s Search for Meaning and Finite and Infinite Games. Female interviews are like a category of books that I have yet to find out about.

I have written up some notes from women: Amanda Palmer, Carol Leifer, Marni Kinry and Kristen Carney, Gretchen Rubin, and Maria Popova is the complete list of female only posts. That’s five out of 120.

I’ll do a better job in 2016, starting now.

This post – Amy Schumer – like a good movie, has narrative arc.

Our hero’s constraints help her in unexpected ways. She enters a battle, and loses. She trains to get better (while getting her butt kicked). She has a moment of inspiration (with instrumental swell of music, is John Williams available?). She defeats the boss, wins the prize, makes a hit. She makes friends. She gives advice. She starts it all over.



Schumer is asked a lot about her looks, and she says she’s “pretty enough.” That’s good news. Constraints are part of the creative process, and sometimes they’re a straight up advantage. Being “pretty enough” helped Schumer get on stage, but it wasn’t enough to keep her there. It was a start. Anything can be a constraint you can use.

Kevin Kelly said that a lack of money helped him be more creative. Tim O’Reilly said the same thing about his business.

“Limitations can expand rather than shrink the creative flow,” wrote Amanda Palmer.

In her book, You’re Never Weird on the Internet, Felicia Day writes that being different helped, a lot:

“I’m glad I didn’t know better than to like math and science and fantasy and video games because my life would be WAY different without all that stuff.”

Even Brian Koppelman had to move to a new medium (stand-up) to have constraints that focused his creativity. Step one of our hero’s journey, you can’t start out as royalty.

When you start, you’ll stink.

Koppelman recalls watching Last Comic Standing (2007) and seeing Schumer on the show. They had both been at the same club a year before and he says to his wife, “this girl is a genius and she sucked so hard just last year.” Everybody stinks at the start.

Austin Kleon articulated why this is so hard. You start doing something – writing, stand-up, marriage – and the only people you’ve seen do that thing are good. That’s why you’ve seen them. You are not good. You are bad.

“There’s a big gap, Kleon says, “when you’re starting out between what you love and what you’re producing.”

Step two of the hero’s journey, step out the door and realize it’s a big scary world.

The grind.

Schumer says that she’s never been jealous of other comedians, but has wondered, why them and not me? She tells Koppelman that she quickly snaps out of it and remembers she has to do the work. It’s time to work, and grind, and hustle.

In Do The Work, Steven Pressfield gives advice on this part:

“Ignorance and arrogance are the artist and entrepreneur’s indispensable allies. She must be clueless enough to have no idea how difficult her enterprise is going to be—and cocky enough to believe she can pull it off anyway. How do we achieve this state of mind? By staying stupid. By not allowing ourselves to think. A child has no trouble believing the unbelievable, nor does the genius or the madman. It’s only you and I, with our big brains and our tiny hearts, who doubt and overthink and hesitate. Don’t think. Act.”

You  have to get to work and not realize how crazy your idea might be. Because it is crazy. Alex Blumberg, Robert Kurson, and Koppelman (“the line between being an artist and being delussional is very thin.”) all explicitly warn people not to examine how hard things will be. Schumer got to work.

She “barked” to get ten minutes on stage. That is, she stood outside, no matter the weather, for two to three hours at a time and yelled at people to come in. Only then did she get a chance on stage.

She worked more, she got better. She toured with Last Comic Standing. “That was like boot camp,” Schumer told Judd Apatow. She toured more. She did slightly bigger and bigger rooms. She persisted, and then she arrived, at the waiting place. Step three is a step back.

The waiting place.

The Waiting Place - By Dr. Seuss

At some point you’ll get to the place where it just doesn’t seem like things will happen. Koppelman’s writing partner David Levien said, “it seems brutal when you’re toiling away in obscurity.”

Brian Koppelman added, “you have to cover that difficult terrain yourself.”

Step four, our hero is stuck, can’t go on, can’t measure up. It won’t happen.

The spark.

If you listen closely, and pay attention, something in the waiting place will spark. Schumer shared two of these instances.

The first was a train ride. Schumer was on a train after a set. It hadn’t gone well. She wondered what she was doing with her life. It was late. Her boyfriend was about to dump her. Things weren’t going well.

It was then that a lady asked if Schumer had “heard the good news.” The women of course was asking Schumer to come to her church. “No, I’m Jewish,” Schumer said, but there was something else in that exchange.

Schumer went home. Told a friend. Wrote a joke. It was good. She had something.

That something is all you need. It’s a foothold on the mountain. Louis C.K. said that this step is the start of a set. You get one joke, that’s your closer. Then you get another joke, that’s your opener. You piecemeal things together until you have an act.

Schumer’s second spark was during Last Comic Standing. Schumer won a challenge and another contestant said, “you don’t deserve it.” “That broke my heart,” Schumer recalls.

But later when the episode aired, she saw the other comics. “I knocked it out of the park, I absolutely did deserve it,” she tells Koppelman.

That spark that gets you out of the waiting place can take a long time coming.

It took Andy Weir years to write The Martian after several failed attempts. Jim Luceno was a carpenter during the first years of his writing career before he believed he could make enough money writing. Jack Canfield says to build failing five times into your plan for success. It takes persistence. Koppelman knows.

“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

Step five, there might be a chance.

As you ascend, have friends.

There are so many people who have partners that help them on their way. Schumer is one of them. She says that her friends are always asking each other if they “have a think about this.” It’s good to have other people who support you around you. People to take comfort with in the waiting place and that can help you in the grind.

Peter Thiel said, “a lot of these companies aren’t solo efforst of a god-like person that does everything.”

Jay Jay French went through ten iterations of the band before he met Dee Snyder and formed Twisted Sister.

Adam Carolla found Jimmy Kimmel and stuck with him because, “we’re funny together.”

Many hands make light work goes the saying, good friends make the work more enjoyable might be a good second part.

Step six, I can do this – no, we can do this.

We did it. We’re famous. Now, get back to work.

Koppelman asks, “was fame a conscious part of the the thing when you were doing this.”

“No,” Schumer says – and it never is.

James Manos said that when they were writing The Sopranos, they never thought about great it might be. B.J. Novak said that the office was never expected to be a great show. James Corden said neither was Gavin and Stacey.

“My goals have been very small,” Schumer says,  “things just right in front of me.”

Even when you “make it” you realize there’s no it. There’s always a higher mountain, and the climb begins again.

Schumer – or anyone – is back where they started. Doing the work, one small bit at a time. The hecklers never die, the doubts never leave, the constraints don’t seem like blessing.

Step seven, repeat as necessary.

Caveat emptor (buyer beware).

It might never happen. To think this sequence is prescriptive would be wrong, it’s descriptive only. In the Charlie Munger/Tren Griffin post we noted how valuable it was to describe the stock market as a person, rather than machine. Mechanistic systems are computers, and even not entirely.

I was reminded of all this because at the end of 2015 I saw a Brian Regan stand-up show. Then for Christmas a friend gave me one of his old CDs. Regan has been at it a long time. Way longer than Schumer. If the path of “successful stand-up comedian” was linear, prescribed, or a checklist, Regan would be a household name. Schumer is, he’s not.

There is something we can do. We can take the advice of astronaut Chris Hadfield and enjoy the process. Hadfield wrote:

“It’s probably not going to happen, but I should do things that keep me moving in the right direction just in case – and I should be sure those things interest me, so that whatever happens I’m happy.”

You need to embark on the journey and be happy with the journey. Schumer admits a bit of this to Koppelman, saying that on Last Comic Standing she was the only one who wanted to hang out after.

Thanks for reading, I’m @mikedariano on Twitter. Want to catch up on the posts, The Waiter’s Pad: Volume 6 is available here. You can also donate a few bucks here.

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