Judd Apatow

Judd Apatow (@JuddApatow) joined Bill Simmons (@BillSimmons) for a new podcast called, two white dads who sit on the couch and complain. Just kidding. While there is a bit of whining from Simmons (who admits it), it’s very small – and the other parts are quite good. Apatow is funny, humane, and sounds like a great guy to hang out with. 

He’s is on to promote, nothing really. His most recent book is Sick in the Head came out in June 2015 and he produced Trainwreck which is a digital download at the end of 2015. Right now he’s doing some stand-up and he talks about that with Simmons. Here’s a bit of his routine:

What I really wanted from this interview was to hear about how Apatow works, and we get some of that. Seth Rogen and Evan Goldberg both praised Apatow when they talked with Tim Ferriss. It feels like Apatow knows something about living well. Which seems weird. This is the man who created The 40-Year-Old-Virgin, but maybe that’s the point. Maybe the person who created The 40-Year-Old-Virgin is exactly the person who knows a thing or two about life.

A few of the other big ideas; lifestyles of the rich and famous, what stand-up does to the brain, the future of entertainment, and comedy as true understanding.


Lifestyles of the rich and famous.

The podcast starts as Apatow and Simmons discuss how people promote their work. It surprises Apatow when people dismiss or knock what other people do. “We’re all trying,” he tells Simmons. It’s not like anyone tries to make an awful movie.

Part of that is being rich and famous. “I love when people talk about some of the difficulties with being famous,” Simmons says, referencing the Apatow and Rock email conversation. “It’s hard for people to understand what it’s like to give up all anonymity,” Apatow says.

Tom Shadyac gave up everything and was happier. Jim Carrey said “I wish everyone could be rich and famous to realize it ain’t it.” Bill Murray added:

“I always want to say to people who want to be rich and famous: ‘try being rich first’. See if that doesn’t cover most of it. There’s not much downside to being rich, other than paying taxes and having your relatives ask you for money. But when you become famous, you end up with a 24-hour job.”

Fame is fickle and is a weak base for life. Naveen Jain noted that if you attach your happiness to something external – whether it’s as grand as fame or simple as kids – you give up control. It’s letting them drive the car. When Phil Rosenthal spoke with Brian Koppelman he was so contemplative about his contentment. Rosenthal wore the Jewish song – Dayenu – like a cloak. Any milestone, like just writing a pilot, would have been enough.

A consistent conclusion for a truly rich life is to look internally. Apatow does this. He’s smitten with his family. Evan Goldberg said his brother’s happy life was how he viewed success. Phil Rosenthal did it. Ryan Holiday wrote a book about how he did it with stoicism. T. Harv Eker saw that a great business wasn’t going to solve this problem. Tom Rath spoke about this too. 

It’s not about being rich and famous, or rich, or famous. Those things are external. They change quickly. It would be like attaching your happiness to the weather – which some people do. Most of those people long for something else. It’s finding something internal. Part of that could be work. 

The 47-year-old comedian.

Why in the world isn’t Apatow making another rom-com? A stoner movie? Why doesn’t he write hilarious television shows? He hears these questions. “When you stretch,” Apatow says, “there are always some people that are so thrilled you are pushing yourself and then there’s always the people who are like, why aren’t you doing the thing you always do?”

Apatow is still making movies and shows, but says he had to do stand-up one last time. “This is the moment,” Apatow says, “where you’ll never do it again. I felt like it was unfinished business.”

Like this unfinished business?

No, not that.

Though Apatow is a famous comedian, there are two parts about his return to stand-up which we should note. 

First, be around good people.

Brian Koppelman used stand-up comedy to unblock his writing. Part of it was being around funny people. That’s key. Koppelman says that those other comedians helped him think differently, they encouraged him, and they failed together. 

If you want to be great at something, Dan Coyle said, you need to be around other people. Coyle calls them “hotbeds.” Austin Kleon calls them a “scenius.” Simon Rich said he wants to feel like he’s barely keeping up. Malcolm Gladwell wrote that part of the reason Jamaican sprinters are so good is because the peer effect is really strong.

Each of these things points you to be around good people.

Second, sharpen your tools.

Apatow echoes Phil Rosenthal, who urged writers to write in different forms. Rosenthal said that if you write for movies, TV, and plays, it’s going to help you be creative in other areas. Koppelman gets this effect when he writes songs. Apatow noted that stand-up, “wakes up some neurons in your head.” It’s true for not just for Hollywood types.

Physicist Richard Feynman writes about this in his book, Surely You’re Joking, Mr. Feynman. Feynman worked in a biology lab. He sat with people from other disciplines at lunch. He studied around the world. He writes, “I got a great reputation for doing integrals, only because my box of tools was different from everybody else’s.” Feynman’s box of tools was bigger than everyone else’s because he learned other things with other people. 

These two things; be around good people and sharpen your tools are not panaceas. “I  always used to think, ‘who cares what you have to say’,” Apatow tells Simmons. It doesn’t matter who cares. What matters is that you tell your story.

Neil Gaiman advocates for people the same way, “There are lots of artists in the world, but there’s only one you. And the only person who has your point of view, is you. If you decide not to make things, all you’ve done is deprive the world of all the stuff that only you could have brought to it.”

Apatow said it took decades to feel this way. He admits to being in a funk for fifteen years after Freaks and Geeks finished. Don’t doubt your story. It’s your competitive advantage said Arthur Samberg. There’s no one that can be Judd Apatow better than Judd Apatow. 

What you do with that is up to you. But, let me make one quick prediction.

A prediction on the future of entertainment.

The old man on the porch role is played by Simmons, and he admits to it during the interview. What happens, he asks, if kids just tweet or gram (is gramming a verb, as in instagramming?). Will that satiate their need to be creative? Simmons wonders what will happen if kids don’t sit down to write a poem or short story. At this point I did wonder how old Simmons was (he’s 46).

But the future never looks like the past. Not only that, it won’t look like the present. Naveen Jain is building a rocket to the moon without any specific plans on what to use it for. Is he worried? Not really. We’ll figure it out along the way, we always do. Kevin Kelly noted that the things we’ll use in twenty five years haven’t even been invented yet. The iPhone only turned 8 in 2015.

Apatow is adapting faster than Simmons. He says that the show he’s doing for Netflix was designed this way. “We are making it with the assumption,” Apatow says, “that people will watch it in two sittings.” The show was created with binge watching in mind. That sounded crazy when I first heard it and then it totally made sense. 

How then do we predict the future?

The only sure prediction is that the future will be different. That said, there is hope. Naveen Jain said that we don’t need to take wild guesses, there are suggestions about what will come next. Like a Hansel and Gretel fairytale (the children who left a trail of crumbs to find their way home), the future does give us clues. A huge clue might be found in comedy.

What comedy says about true understanding.

Simmons asks Apatow what he thought about the backlash to Rogen’s movie, The Interview. “It did do something important.” Apatow says. “We should remind the world that there are people suffering and being murdered. That’s the point of comedy and satire.”

Jason Zweig felt this way too, and it’s why he wrote The Devil’s Financial Dictionary. “The ability to define a term in such a way to be cynical or funny is a measure of your own skepticism,” said Zweig. If you can make a good joke about something, it’s a signal for deep understanding.

When Gary Vaynerchuk said that he had “high emotional intelligence,” it’s along the same lines. And knowing something deeply is important.

When Taylor Pearson projected what he thought jobs would look like, he noted the value of deep understanding. All the successes in Pearson’s new economic landscape, have done 2-3 things really well. Comedians have known this a long time.

Carol Leifer may be the best example of this because of her longevity. She’s found humor in things for decades. This is the future. The people who learn something well and understand human nature will succeed.

Whatever arena you’re in, you need to figure out the details. Ramit Sethi said you have to know the important numbers for your business. Jason Calacanis said that you have to know your product, your competitors, and your industry. Dan Coyle calls this the “construction” part of talent. Brett Steenbarger terms it analyze. Each of these people uses different terms, but speaks to the same idea.

If you want to be funny, you have to know the thing you’re talking about. Apatow displays this in the podcast. He talks about going to a Taylor Swift concert. He talks about his movies. He explains the process of working with Gary Shandling (which was absolutely fantastic but I didn’t know how to include it in this post. It’s at about the 31:00 mark, go listen to it.)

Thanks for reading, I’m @mikedariano on Twitter. Wow, you made it to the end of the post. A solid 1700 words. These posts take about 5 hours in all to write. If you liked it enough to say thanks, you can donate $2.

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