Judah Friedlander

Judah Friedlander (@JudahWorldChamp) joined Brian Koppelman (@BrianKoppelman) on The Moment podcast. The duo talk about Friedlander’s new book, If the Raindrops United, but cover a lot of other ground too. By the end of the interview I empathized with Friedlander. He’s just a person, who tries hard, and faces challenges. Like everyone else. So many people, from Judd Apatow to Tom Shadyac say that life isn’t about fame or money. It’s about more than that. It sounds like Friedlander has lived this. He’s still unsure of himself (and has good company, check out the Apatow link). He still fails. He’s still looking for more. Here’s hoping he finds it.

There’s more good stuff here. Our route includes, comedy as an advanced thinking technique, starting out, crazy like a fox (but not one bit more), the craftsman mindset, and why you need to start right now.


Comedy as an advanced thinking technique.

Koppelman notes that some of the jokes from Friedlander’s book have a deeper message in them. “Yeah they do,” Friedlander says. Judah explains that as he became more popular as a comedian, he started to tour more. More touring meant more places. More places meant new places. There, he began to notice things about America.

Not bad things, but different things. “I started to see how other people lived,” Friedlander said.  Hence the new book, and the book might be the catalyst for Friedlander’s next success.

Phil Rosenthal suggested that people write in different mediums. Friedlander said that stand-up is his “home base,” but because he wrote for 30 Rock, has written other books, his standup is probably better. Judd Apatow said that different forms awaken different neurons. Brian Koppelman writes music for the same effect.

Comedy writers especially need those other neurons to be awake, because comedy requires deep understanding. Jason Zweig challeged himself to write The Devil’s Financial Dictionary to see if he knew what he was talking about. Judd Apatow also said that  comedy requires a deep understanding.

But, we’ve gotten the cart in front of the horse here. Before we become great, we need to start.

Starting out.

“I never realized being a comedian was a thing you could do,” Friedlander says. It wasn’t until he saw stand-up on TV and hte post routine banter that he realized it could be a job. After a set, the show host went up to talk to the comedian, and they would plug wherever they were performing.


This was a lightbulb moment for Friedlander. “I was like, ‘whoa’ You can do this?” he says.  “When I was sixteen, I realized I wanted to do standup.”

A generation earlier Phil Rosenthal missed this. Rosenthal (also on Koppelman’s show) said that he saw actors on television, but that was it. He wanted to do that, but didn’t know what that was.

Seeing may not be part of believing, but it may be part of achieving. In his book, The Talent Code, Dan Coyle noted that many people succeeded in “hotbeds.” His book begins with the story of a Russian Tennis club that graduated a single player to the professional tour. Then four. Then six. Coyle looked around and found that seeing helps achieving in other areas too. 

Malcolm Gladwell worked at a newspaper that challenged him with how much he could write. Later on he wrote Jamacian sprinter are so good for part of the same reason. 

Simon Rich said he wants to be the dumbest one at the writing table.

Austin Kleon suggested people find a group. Nicholas Megalis noted that the internet has made this easier than ever.

In whatever group you start with, make sure you do things a little differently. Try to be crazy like a fox.

Crazy like a fox – but not more.

Projects succeed most when they are different. Naveen Jain had a different internet company. Nearly all of Peter Thiel’s book, Zero to One is about being different:

“All happy companies are different: each one earns a monopoly by solving a unique problem. All failed companies are the same: they failed to escape competition.”

Phil Rosenthal said that he had to make Raymond, not Seinfeld. If he tried to make something like Seinfeld, it would fail. Penn Jillette said not to imitate the Rolling Stones if you like the Rolling Stones. Those guys already nailed that, Jillette says, instead do something different.

How can you be different?

“You can’t be too crazy,” Friedlander warns, “if you get too crazy you’re not functional.” His book is different. That’s good. Friedlander can’t write the book that Jim Gaffigan or B.J. Novak or Tina Fey wrote. Those have been done. He had to do something different than them, and that meant he had to be crazy, crazy like a fox.

How to be crazy like a fox:

Step 1: Stretch. Steven Kotler said that the best extreme athletes stretch themselves 4% past what they think is posible. Do that and you’ll find something new.

Step 2: Have wide inspirations. You need to take ideas from many areas. Neil Gaiman said that if you want to be the next Tolkien, don’t read Tolkien. Jillette said that Guns n Roses idolized the Rolling Stones, but knew they couldn’t imitate them. So they did something different.

Step 3: Remix. “Everything is a remix,” Austin Kleon said. Even the Thiel quote above about being different is a remix of Tolstoy.

Step 4: Persist. Timing is impossible to nail. The only thing you can do is keeping doing it. Mark Cuban offered streaming music years too early. Trip Adler had the idea for ride sharing years too early. Neil Strauss released his book the same weekend as Hurricane Katrina.

Timing something just right is impossible. It’s not like a cruise missile. Instead, you need to persist with your new idea. Oh, and  one more thing.

The craftsman mindset.

“Most people aren’t doing a job well,” Friedlander says. People need the right mindset. Penn Jillette said that he and Teller worked on part of their act for six years. Not a new act. Not even half an act. Two minutes. They spent six years of work for two minutes of material. That’s what makes us great, Jillette said. “The most important thing,” he continued, “is everything.”

This can be lonely work. David Levien said, “it seems brutal when you are toiling away in obscurity.” But you have to focus on getting better.

Cal Newport termed “craftsman mindset” in his book, So Good They Can’t Ignore You. The book title comes from the Steve Martin quote that nobody wants to hear:

“Nobody ever takes note of [my advice], because it’s not the answer they wanted to hear,” Martin said. “What they want to hear is ‘Here’s how you get an agent, here’s how you write a script,’…but I always say, ‘Be so good they can’t ignore you.’”

You have to do the work and get great at something. Let’s have one more example.

If you watched Seinfeld you probably remember Tim Whatley, the dentist who pretended to be Jewish so he could tell Jewish jokes. The actor who played that character was in five episodes of Seinfeld from 1994-1997 but also had 35 other roles during that same time period. Those other shows included the television movie Extreme Blue and the show Teknoman.

One of the writers on Seinfeld remarked that he was constantly auditioning for roles, and when she asked him about what he had been working on, he told her he forgot. He did so many auditions that he couldn’t keep track of them. He was, in Newport’s words, building career capital.

In 2000 that actor was cast as a lead on a network show and he worked on bigger shows like The King of Queens and Family Guy.  But not until 2008 did he reach the upper echelons of his field and win an Emmy Award for playing Walter White on Breaking Bad.

Bryan Cranston is a great example of building up the career capital. It shows in his IMDB profile too, those 35 roles during his time on Seinfeld were for TV movies and shows you’ve probably never heard of. Then his choice of roles became fewer and more selective on shows like The X-Files and Chicago Hope until he was cast in Malcolm in the Middle.

Need more? Check out Gary Vaynerchuk on being an overnight success:

A final note.

It’s time. For whatever you’re doing, it’s time. This was so clear in the Friedlander interview. Judah needs to go for it. That’s easy for me to write, (so easy), but it’s worth pointing out.

There’s no perfect time for anything. Now is the time for Judah to do a stand-up special. Now is the time for you to start something. Now is the only time we have.

In honor of Koppelman, we’ll end on this this.


Thanks for reading. Thanks for reading, I’m @mikedariano on Twitter. Wow, you made it to the end of the post. A solid 1600+ words. That’s pretty long online. If you found a few things valuable, you can [donate $2]

Wow, you made it to the end of the post. A solid __ words. That’s like __ pages in a book (and forever online). If you found a few things valuable, you can donate $2.

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