Eight things I’ve Learned from Judd Apatow (Part1)

Judd Apatow is six shades of wonderful. His lovely conversation with Bill Simmons inspired me to get his book; Sick in the Head: Conversations About Life and Comedy. The book is funny and tender and full of life lessons.

Judd Apatow fascinates me. Whether it’s seeing his work (Girls, 40-Year-Old Virgin), hearing people (Seth Rogen and Evan Goldberg) talk about him, or reading his book (Sick in the Head) – I can’t get enough. Here are 8 things I learned from Judd Apatow. 

One note: This is Part 1 of 2, and the format of this post is inspired by the posts Tren Griffin does at 25IQ.


Optionality is a powerful force of life. Scott Adams compared it to playing slots, except the machine of life doesn’t require money. “I find it helpful to see the world as a slot machine that doesn’t ask you to put money in. All it asks is your time, focus, and energy to pull the handle over and over.”

In 1983, Apatow interviewed Jerry Seinfeld and asked what he was going to do next. “Quality. That’s my only real consideration. It could be anything as long as the people are trying to do something good. I don’t want to do a piece of junk. I’m not starving you know.”

Seinfeld was thinking about optionality, and a lot of other people do too:

A – Charlie Munger and Warren Buffett wait for investments with large upsides.

B – Nassim Taleb thinks about options for his investments, but also his dinner choices. “The most interesting options,” Taleb writes in Antifragile, “are free, or at worst, cheap.” p175

C – Donald Trump writes in The Art of The Deal that a good property has to be purchased for a good price. And then, “it takes almost the same amount of energy to manage 50 unites as it does 1200 – except that with 1200 you have a much bigger upside.” p57

D –  B.H. Liddell Hart wrote “The classic book on military strategy” and concluded that optionality was the main ingredient for victory.

Boot camp.

“(The Last Comic Standing Tour),was like boot camp.” – Amy Schumer, 2014

Apatow talks to Schumer about being a female comedian and she has a lot of good things to say. Not that things are good but good to know. I think Schumer is wonderful and I’m glad she’s in the book.

She also touches on something both Malcolm Gladwell and Casey Neistat suggest; volume under pressure. You need a certain volume of work under pressure to develop your skills. In the same way that carbon accumulates under pressure to form a diamond, valuable skills can be created the same way.

Boot camp isn’t glamorous. David Levien said, “it seems brutal when you’re toiling away in obscurity.” But it’s work that needs done. 

Stand still, walk, or run.

“It’s almost impossible to keep success going because you have to stop at some point to rest and learn something new.” – Chris Rock, 2014

One challenge of stand-up, said Rock, was filling up your tank. You need to have a life that you can talk about in your act, he tells Apatow. But if you constantly do your act, you don’t have a life.

Michael Lombardi told Shane Parrish that this is a huge challenge in the NFL too. Everyone there is running, and to get ahead you need to run faster. That’s tough, there’s no time to learn something new.

Casey Neistat made this video which explains this idea::

The spark.

“I just try to always remember where that initial spark came from. It’s like a pilot light, and you try to make sure it doesn’t go out.” – Eddie Vedder, 2013

Vedder tells Apatow how he tries to remember where his start. His muse. His catalyst. That was the energy state that started the ball rolling.

For a lot of comedians in the book it’s fear and pain. Seinfeld stands out as one of the few interviewees that doesn’t emotionally pull the reader. I felt like I wanted to hug everyone – including Rosanne. Even Apatow has these feelings. Jim Carrey has the strongest ones (that will be in part 2). If your spark is dark, it’s hard to get past it. 

Dayenu (it would have been enough).

“If it never happens again, I’m okay with that. At least it happened once.” – Apatow about Freaks and Geeks. 2013

This was a tender part of the book. If you have a kid, and they lose their favorite stuffed animal, you understand a sliver of Apatow’s Freaks and Geeks experience. Apatow was very open about it during his podcast with Bill Simmons. He loved those people. It’s why he kept working with so many of them. It was a family.

Now Apatow has the comfort of understanding that moment. He understands, as Phil Rosenthal noted, Dayenu. Rosenthal said that at any point in his career, “it would have been enough.” Rosenthal sounded at peace and only years (decades?) later, Apatow feels the same way.


Garry Shandling hosted the Tonight Show for the first time thanks to luck. The first choice, Albert Brooks, got sick 24 hours before he was set to host.  

Jason Zweig said his writing opportunities were based on luck. It’s part of Scott Adams’s moist robot theory: “If you control the inputs, you can determine the outcomes, give or take some luck. Eat right, exercise, think positively, learn as much as possible, and stay out of jail, and good things can happen.”

Mark Cuban and Seth Godin both cashed out before the dot com crash and admit they got lucky. Trip Adler says that at Y-Combinator he was told his idea for a ride sharing app wouldn’t work. It was 3 years before Uber.

Luck matters. “I’ve thrown a lot of darts and I don’t necessarily take credit,” said Naval Ravikant “a lot of it was luck.”

My favorite day of the week.

“The good time movie for me has been every single one of them.” – Harold Ramis 2005

For a guy that worked with Bill Murray, Chevy Chase, and John Belushi, and with Second City, Ramis has so many great sources to pick from. But he appreciates the moment – something Naval Ravikant is trying to do more of. That’s all we have is the moments.

His comments about movies reminded me of this moment from Winnie the Pooh:


“What day is it,” asked Pooh.

“It’s today,” squeaked Piglet.

“My favorite day,” said Pooh.


“I’m trying to fuck my kids up just enough so the’ll want to get a job.” – Judd Apatow 2014

Apatow talks with James L. Brooks about life and death and comedy. His comments come after telling Brooks about his life growing up and why he worked so hard when he was young. As a kid he saw his parents go through a nasty divorce (his mom charged 30K$ to his father’s credit card) and Apatow realized he had to earn money.

Apatow worked really hard. What’s noticeable about his early interviews was how young he was. From interviewing Seinfeld as a high schooler to being the youngest writer for Garry Shandling, Apatow was the youngest at everything. He worked hard because he had to.

This challenge is good. In The Obstacle is The Way, Ryan Holiday examines situations where different people succeed despite the challenges. Holiday writes this: Before he was an oilman, John D. Rockefeller was a bookkeeper and aspiring investor— a small-time financier in Cleveland, Ohio. The son of an alcoholic criminal who’d abandoned his family, the young Rockefeller took his first job in 1855 at the age of sixteen (a day he celebrated as “Job Day” for the rest of his life).”

Apatow wants some of this for his daughters. Some resistance, some obstacles.

Part 2 will be out Friday.

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