David Perell

"The Writing Guy" | Christian | Host: How I Write Podcast | I tweet about writing, beauty, and architecture | My writing:

[David Perell @david_perell]

The Malcolm Gladwell Interview

His books were some of the first I ever read because we had copies of Outliers, Blink, and Tipping Point all around my childhood home. Then when I was getting into writing, I learned how to open essays by studying his New Yorker profiles.

So I wanted to ask him how he tells stories, makes his audiobooks, and manages to be such a prolific writer.

Timestamps:

00:00 Introduction
00:38 How are puzzles similar to writing
04:55 Why specificity matters more than knowledge
12:28 How Malcolm wrote his new book
17:02 Stop readers from leaving
19:28 What he learned from John le Carré
23:58 What he learned from Michael Lewis
27:15 You should engineer your curiosity
30:59 Why memory is underrated
33:37 Give readers a big why
38:15 How to make readers cry
41:29 What audio formats mean to him
45:57 Leave room for uncertainty
48:37 Pace your story like a runner
53:02 Say more with fewer words
55:24 Malcolm’s advice for beginner writers

Here's what stuck out to me:

1) “I will turn down a story if I do not think it has intrinsic interestingness.”

2) Most of Malcolm's writing life doesn't revolve around sitting at the keyboard: “Most of my days are spent either reporting or arranging to report.”

3) Writing books requires you to pace yourself. It's like running: “In mile one, you could run much faster, but you deliberately don’t because you want to last for mile ten.”

4) "Other people have stories. Go and find out what they are." You don't need to come up with stories on your own if you're curious enough to ask questions and wait patiently until a story emerges. Doing so removes the pressure to manufacture a story from a blank page.

5) Malcolm's spent tons of time with Paul Simon and was repeatedly struck by the depth of his reference archive. He's like a walking LLM, with unlimited resources for summoning facts, riffs, and musical ideas.

6) 'Granularity' is the thing you want from the people you interview for a book. The most important person won't always give you that. Sometimes, it's the person on the front lines or the periphery of a situation.

7) Audiobooks shouldn't quote people the author interviewed. They should have the original tape from the original interview so the listener can hear it right from the source. He says: “Why bother reading someone’s quote when it’s audio? Play the tape. Let’s hear them speak.”

8) Audiobooks are so core to his work that he thinks about the audio experience before he even writes the first word of the book.

9) Sometimes, in an audiobook, the emotional register is better set by a song than prose. That's why Malcolm's new audiobook opens with music by Drew Holcomb. In 2.5 minutes “he accomplishes something I couldn’t do in the book.”

10) Delay your conclusions when doing research: “The penalties associated with premature conclusions are so large.” For example, Gladwell regrets how quickly he embraced the Broken Windows theory as an explanation for crime in New York.

11) You don't need to be good at every part of writing in order to be an outstanding writer. For example, if you have a strong voice and lively characters, you don't need an elaborate plot. He says: "Just give us enough plot to activate another part of our brain.” The point is that every part of your book should support the thing you're uniquely good at.

12) It was interesting to hear Malcolm reflect on his earlier writing and confess that he got too cute with coming up with fun names for things.

13 Is laughter slightly overrated in our current culture? Gladwell says: "Getting someone to laugh is far easier than making them cry.”

14) Interview your parents before they die: "Think about how many people, when asked about their parents after they’ve passed, say, 'I never talked to them about that. I wish I had.'”

15) If Malcolm were teaching a class on writing, he'd make kids skip class in order to sit down with their parents, record them speaking for 45 minutes, and then run the conversation through an AI transcription service. Then they'd bring the transcript back to class and write a short article about the conversation. "That's where we’d start on day one. We would then build from there."

I've shared the full conversation with @Gladwell below. If you'd rather watch the full thing on YouTube, or listen to the episode on Apple / Spotify, check out the reply tweets.

Enjoy!

[How I Write Clips @PerellClips]

Robert Greene spent the past seven years writing about the word “sublime.”

“It’s not dainty. It’s not fussy, old-fashioned, or quaint. It’s a mix of terror and exhilaration, of awe and fear.”

“When you look up at the night sky… if you really thought about it: goddamn, I am so small. My life doesn’t matter at all compared to a billion years from now. No one will ever know who I am.”

@RobertGreene

[David Perell @david_perell]

@rivatez Yes, yes, yes!

[Riva @rivatez]

Many people in tech have made, or are about to make, large sums of capital. I want to make a petition for more philanthropy towards historical buildings- specifically Churches

Every year, dozens of historical Churches fall into disrepair around Europe. Hundreds of these deconsecrated buildings are up for sale

I don't believe you need to be Christian to recognise the value in saving these buildings. You just have to respect history. It is a travesty to see these buildings- that were the cradle of communities and our civilisation- fall into disrepair or even get demolished

These Churches should not become financial assets- not yoga studios, not backdrops for light shows, not a rental opportunity. We should allow them to remain as sacred spaces- the preservation of our history is enough

When you take on these sorts of projects, people will say, "Oh, but these are money drains! They will just need continuous repair- and you'll have nobody to sell them to!" Consider perhaps that in this you will find the whole point

You could save a Church for low six figures. A very wealthy person could save a lot of them. I have taken on one, and it has been one of the most beautiful and meaningful projects of my life

[How I Write Clips @PerellClips]

“Every writer I know who thinks they’re really good sucks. Only bad writers think they’re good."

"You need a little bit of fear, I think, when you when you write."

“No matter what I’m doing, including sitting here with you right now, there’s a little voice that’s always like, you really should be writing.”

“You have to be a little bit obsessed with this thing to do it right.”

-Harlan Coben (Over 90M books sold)

[How I Write Clips @PerellClips]

“If somebody doesn’t want to cooperate, I’ll write about them anyway.”

Patrick Radden Keefe has built a career writing about people who didn’t want to be written about.

His advice if a journalist calls: talk to them. The story is getting written either way.

“A lot of the time in journalism, that’s kind of the end of the story. For me, that’s often the beginning of the story.”

“Anytime I start writing about somebody, I will always make the effort to talk to them. And I always think that it’s probably a good idea for them to talk to me, whether they do or not.”

“What I say to them is the train is leaving the station.”

“I wrote a big profile a couple of years ago of Larry Gagosian, the art dealer. I thought he would say no. And then he said yes.

I think it was savvy of him to do so because he realized 'there’s only gonna be so much real estate in this piece. And if I come in, I’m my own best advocate. And the more I talk, the more real estate I’ll take up.'”

[How I Write Clips @PerellClips]

"When you ask people about their parents after their parents have passed, every single person I've ever talked to about this said, oh yeah, I never talked to them about that. I wish I had."

If Malcolm Gladwell taught a semester on writing, this is the assignment he would give:

"I would have the kids go home, and I would have them interview their parents and bring the transcripts back into the class."

"Kids think the burden is on them, and that's why they're so inhibited when it comes to writing. We're not asking you to tell a story. Other people have stories. Go and find out what they are."

[David Perell @david_perell]

How I Write wouldn't be possible without the support of Alpha School.

Years ago, Alpha's founder @jliemandt said to me: "You can build the best writing podcast in the world, and I'm here to help." That spirit defines everything at Alpha. It's a place where students are encouraged to think bigger and raise their ambitions.

It's the school I wish I'd been able to attend, and I'm exceptionally proud to have Alpha as the sponsor of the show.

They're opening new campuses across America, and if you're interested in enrolling your child, learn more at the link below.

https://t.co/ZlBAhAkM9G

[David Perell @david_perell]

The Malcolm Gladwell Interview

His books were some of the first I ever read because we had copies of Outliers, Blink, and Tipping Point all around my childhood home. Then when I was getting into writing, I learned how to open essays by studying his New Yorker profiles.

So I wanted to ask him how he tells stories, makes his audiobooks, and manages to be such a prolific writer.

Timestamps:

00:00 Introduction
00:38 How are puzzles similar to writing
04:55 Why specificity matters more than knowledge
12:28 How Malcolm wrote his new book
17:02 Stop readers from leaving
19:28 What he learned from John le Carré
23:58 What he learned from Michael Lewis
27:15 You should engineer your curiosity
30:59 Why memory is underrated
33:37 Give readers a big why
38:15 How to make readers cry
41:29 What audio formats mean to him
45:57 Leave room for uncertainty
48:37 Pace your story like a runner
53:02 Say more with fewer words
55:24 Malcolm’s advice for beginner writers

Here's what stuck out to me:

1) “I will turn down a story if I do not think it has intrinsic interestingness.”

2) Most of Malcolm's writing life doesn't revolve around sitting at the keyboard: “Most of my days are spent either reporting or arranging to report.”

3) Writing books requires you to pace yourself. It's like running: “In mile one, you could run much faster, but you deliberately don’t because you want to last for mile ten.”

4) "Other people have stories. Go and find out what they are." You don't need to come up with stories on your own if you're curious enough to ask questions and wait patiently until a story emerges. Doing so removes the pressure to manufacture a story from a blank page.

5) Malcolm's spent tons of time with Paul Simon and was repeatedly struck by the depth of his reference archive. He's like a walking LLM, with unlimited resources for summoning facts, riffs, and musical ideas.

6) 'Granularity' is the thing you want from the people you interview for a book. The most important person won't always give you that. Sometimes, it's the person on the front lines or the periphery of a situation.

7) Audiobooks shouldn't quote people the author interviewed. They should have the original tape from the original interview so the listener can hear it right from the source. He says: “Why bother reading someone’s quote when it’s audio? Play the tape. Let’s hear them speak.”

8) Audiobooks are so core to his work that he thinks about the audio experience before he even writes the first word of the book.

9) Sometimes, in an audiobook, the emotional register is better set by a song than prose. That's why Malcolm's new audiobook opens with music by Drew Holcomb. In 2.5 minutes “he accomplishes something I couldn’t do in the book.”

10) Delay your conclusions when doing research: “The penalties associated with premature conclusions are so large.” For example, Gladwell regrets how quickly he embraced the Broken Windows theory as an explanation for crime in New York.

11) You don't need to be good at every part of writing in order to be an outstanding writer. For example, if you have a strong voice and lively characters, you don't need an elaborate plot. He says: "Just give us enough plot to activate another part of our brain.” The point is that every part of your book should support the thing you're uniquely good at.

12) It was interesting to hear Malcolm reflect on his earlier writing and confess that he got too cute with coming up with fun names for things.

13 Is laughter slightly overrated in our current culture? Gladwell says: "Getting someone to laugh is far easier than making them cry.”

14) Interview your parents before they die: "Think about how many people, when asked about their parents after they’ve passed, say, 'I never talked to them about that. I wish I had.'”

15) If Malcolm were teaching a class on writing, he'd make kids skip class in order to sit down with their parents, record them speaking for 45 minutes, and then run the conversation through an AI transcription service. Then they'd bring the transcript back to class and write a short article about the conversation. "That's where we’d start on day one. We would then build from there."

I've shared the full conversation with @Gladwell below. If you'd rather watch the full thing on YouTube, or listen to the episode on Apple / Spotify, check out the reply tweets.

Enjoy!

[David Perell @david_perell]

Here's the full interview on YouTube

https://t.co/AIS59pCVTu

[David Perell @david_perell]

@serxzsz Yep

[David Perell @david_perell]

@jacksondahl My man! Impressive

[How I Write Clips @PerellClips]

"Some of my friends who are huge bestsellers do the five pages a day or 2,000 words a day, and I was like, 'what is this bullshit?'"

"If I'm running to my desk to write, that is a good thing. If I write fast, that is a good thing, because it is crystallized and I know where I wanna go."

"It has to start with the premise of: am I excited about this? If I'm not, then don't write it, because there's no way in hell that anybody's going to enjoy reading it."

- David Baldacci (over 200 million books sold)

[David Perell @david_perell]

@samarthgowda215 Holy cow dude… this is fantastic!

[samarth @samarthgowda215]

a year of YouTube packaging strategy (for podcasts) in one article ↓ https://t.co/rMu0VNwJFo

[How I Write Clips @PerellClips]

The main thing comedian Taylor Tomlinson learned from Anne Lamott's Bird By Bird wasn't about writing:

"Bird by Bird is the writing book I've gone back to the most because the part of that book where she talks about how perfectionism makes you think that if you're perfect, you're never gonna have to die, but you are gonna die.

And everybody else who, like, wasn't as obsessed with perfection as you is gonna die too, but they had more fun than you."

"I swear to god, I think about that every single day of my life, and that's just, like, good life advice. It goes beyond writing."

[How I Write Clips @PerellClips]

Gillian Flynn learned everything she knows about screenwriting from working with David Fincher on adapting Gone Girl to the big screen:

"Some directors come in and it's like, it's because something's gonna be a hit or they can, cast a big name. Whereas he came in really knowing and liking the book."

"I made the script exactly a 120 pages. In Hollywood, if you go any longer, they're gonna think that you're this darling novelist who can't kill her babies."

"And the first thing, David was like, let's put more of the book back in here."

"He works harder than anyone I know. He doesn't phone anything in. Even down to an insert shot."

"He's always willing to go back and see, like, is there more to be gotten out of this?"

[David Perell @david_perell]

@dwarkesh_sp My man!! So cool

[How I Write Clips @PerellClips]

"I felt it was being a little sexist to think that only men could be evil."

Gillian Flynn is known for writing riveting, evil female characters like Amy Dunne in Gone Girl. She told me what motivated her to focus on female evil:

"I've thought a lot about female evil, and in a way, it was because I just felt that we weren't properly represented."

"I always was kind of pushing back against that idea that women are too kind."

"That's just demonstrably incorrect if you look anywhere around the world, and if you talk to any woman who knows other women."

"It leaves women with only this idea of seeing in film or TV or books female characters who are helpmates."

"So it really was part of the reason I wrote Sharp Objects was to examine what violence looks like with women."

[David Perell @david_perell]

How I Write wouldn't be possible without the support of Alpha School.

Years ago, Alpha's founder @jliemandt said to me: "You can build the best writing podcast in the world, and I'm here to help." That spirit defines everything at Alpha. It's a place where students are encouraged to think bigger and raise their ambitions.

It's the school I wish I'd been able to attend, and I'm exceptionally proud to have Alpha as the sponsor of the show.

They're opening new campuses across America, and if you're interested in enrolling your child, learn more here: https://t.co/ZlBAhAkM9G

[David Perell @david_perell]

Gone Girl was such a wild movie that I watched it twice in theaters in two days, then immediately read the book.

And finally, I got Gillian Flynn to tell me how she wrote the book and made the movie. Her stories are dark, character-driven portrayals of evil, so I was surprised when she kept talking about how much fun she has while writing. Of all the interviews I've done, she's the writer who talked most about having fun.

So this conversation is about how she writes, brings characters to life, and especially how she wrote Gone Girl.

— —

Timestamps:

1:03 How to write suspenseful stories
5:16: The setting needs to be intentional
8:24 Why we crave dark stories
13:23 Female evil
20:27 What makes for a good character?
24:35 How to unstuck yourself
30:56 Beating writer's block
40:04 Mistakes screenwriters make
42:59 Lessons from TV writing
45:05 Horror movies
46:20 Naming characters
51:02 Are we all performing now?
56:23 Writing books vs. movies
1:07:23 How to start a book
1:15:33 Gillian's advice for writers

— —

Some highlights:

1) Better to have great characters and a mediocre plot than a great plot and mediocre characters.

2) The idea that your characters need to be likable is nonsense. Rather, the most important test for a main character is this: “Am I interested in knowing more about this character?”

3) To write monstrous behavior, start with an ugly impulse in yourself and amplify it 20x. What happens when you feed that impulse? Justify it? Organize your life around it? Answering these questions can give your characters an interior life beyond the label of "evil."

4) When you’re stuck, write three pages without trying to make them belong in the book. It can be a childhood scene, a letter they wrote, a furious rant in a character's voice, or anything like that. What matters is that you insist it's only an exercise so you can unstuck yourself. This is where the Cool Girl monologue in Gone Girl came from.

5) When making the Gone Girl movie, David Fincher would ask her: "Why is this happening here?” Sometimes, the act of explaining would reveal the scene's purpose and help her improve it. And other times, she'd see the scene wasn't necessary.

6) You don't need to write the beginning of the book first. Gillian avoids saying "okay now this is the first sentence" because doing so carries so much pressure. So once she's done with the book, she goes back to the front of the book and writes the beginning.

7) When you find a writer you're jealous of, read their work carefully. For Gillian, it was the work of Kate Atkinson, whose writing made her cry and laugh in the first three pages, so she went back and asked: “How did this magic happen?”

8) It's fine if people don't like your book. What's actually a problem is indifference. She says: “People have come up to me at readings, slammed the book down, and said: 'I hate this book. I'm only here because book club made me.' For me, that reaction is great because it means you thought about it. I’d much rather have that than someone saying, 'I liked it; it’s good,' and then never thinking about it again. I don’t want a book that just washes over you and then is forgotten."

9) Choose settings that take away the kinds of freedom your characters want. In Gone Girl, Amy constantly wanted to reinvent herself. Placing the story in a small town made that impossible and sowed the seeds for all that happens in the story.

10) Gillian doesn't know how her stories will end when she starts writing them. But once she finishes a draft, she goes back and places clues that add suspense to the story and integrity to the ending. She says: “If you go back and trace everything, you’ll see I earned it.”

To watch the full conversation, check out the video below. If you'd rather watch on YouTube or listen on Apple / Spotify, check out the replies.

Enjoy!

[David Perell @david_perell]

Watch the full thing on YouTube

https://t.co/fnmDqQGtXE