How To Master Storytelling ft. David Perell

All right, look, it's Sean here. I don't want to toot my own horn, but beep beep. This is, this is a, this is an interview that somebody else did with me. Uh, David Perel, who you might know online as The Writing Guy. He, uh, invited me out to San Francisco and we did an interview for his podcast called How I Write. And my episode is doing so well. So well. It is. I have this little Chrome extension. This thing is doing 11x. 11x means it is 11 times higher performing than his normal videos. Something good is in this video that is doing 11x on YouTube. And it's all about storytelling. It's all about writing. It's stuff that a lot of people ask me about, but I'd never have taken the time to sit down and talk about it. Well, David got me to sit down and tell you everything that I know about this stuff. I hope you like it. I was a little sick during the interview, but it was my Michael Jordan flu game. I came prepared and I brought the heat. I'm really hyping this up and it's because I'm excited about it. I'm really proud of this interview. It's doing really well. A lot of people are messaging me about it. And so we want— you ask David, hey, can we run this on our our feed. Um, you know, we took the, took the episode from him. We're going to run it on our feed. It's basically an interview where he's the interviewer and I'm the guest talking about storytelling and writing. So if you like those two things, you're going to like this episode. All right. Enjoy this episode with me and David. Story is a 5-second moment of change. Whoa.

What does that mean?

You want to work backwards from the emotion. The only things people will share is things that are LOL, WTF, OMG.

Wait, so hold on here. Stop the podcast. So what should I do next time I sit down to write?

The real great writers, I believe, are great at framing their ideas.

Oh, interesting.

So MrBeast, Steve Bartlett, Dave Chappelle, Hasan Minhaj, those are the people I try to learn from. I could teach a 30-second masterclass. It's just this.

Sean Puri is one of those guys that I really wanted to learn from. I've spent a lot of time thinking about how to tell better stories by listening to good storytellers, but Sean has really deconstructed the storytelling process. And you hear people saying all the time, "Oh, storytelling's really important. You should get really good at it." But there's not a lot of people who come in with concrete, clear frameworks like he does. So this is a masterclass on storytelling. Come on in. It's time to roll. I said this to you when we first shook hands, but this podcast was probably the biggest increase in terms of how much I've admired a guest and how much that's grown through the prep process. And so I just want to compliment you on that. And in particular, there's a lot of things that you do really well in your writing that I'm not good at. And this is one of those episodes where I just have a bunch of questions and I'm here to make my writing way better. And the place I want to start is storytelling. I have no frameworks for thinking about storytelling.

Before we do storytelling, can I give you a compliment on your compliment? Yeah. So Great compliment, first of all, very specific. But the second is actually, it's a writing tip, which is the thing you said where you're like, "I started kind of going down your rabbit hole and my respect for your," whatever you said, "Your score went up a lot during that process." I learned this from these two guys, Dylan and Henry. They're young guys. They were 21 when I met them and they were recording these videos. I was like, "How many views do these get?" And they were like, "Oh, nobody watches these." And I'm like, "But you guys are really trying. Is it like someday somebody will watch these?" He's like, "Yeah, specifically we're creating a binge bank." And I was like, "What's a binge bank?" And he goes, "It's when you basically stack material so that even though each one of these, if we just looked at the view counts, it'd be discouraging, not that many people read this or watched this." But they were like, we started thinking about it differently. Instead, we said, all right, each one's not getting that many views, but I'm creating a bank where if somebody ever said, I'm curious about this guy, I want to learn more, what is this guy all about? That in the next hour, you would walk out with my reputation would be way higher with you. You would feel like you know me, you would like me, you would respect me. And it changed the way I thought about that. And so then I— because I used to not— I used to be very results-driven. It's like, ah, if it's not immediately paying off, It's hard for me to get excited about it. But when I thought of the Binge Bank, I just thought, oh, I need to create this library that if anybody, if David's going to do research, he's going to spend an hour or 2 hours going down the rabbit hole, I need to leave a little breadcrumb trail that by the end he's like, I love this guy. I'm all about this guy.

Guess where I ended up? Guess what the final thing was, which was the shebang of, all right, I totally buy it.

Some old blog post that I probably forgot about is my guess.

It's like that 40-page PDF with all your main principles. That was the pool I swam in for the longest. And I ended up there.

Yeah, who knows? But you leave that trail. I should probably do it better, but this idea of create a binge bank, I think is so much more valuable than a resume or a portfolio. It's like people will come knocking, they will get curious about you and give them a way to just binge your content like it's a Netflix show. And after 2 hours, they should feel like you're the man. That's a goal I think people should have.

So what do you do to do that intentionally?

Well, the first thing is you don't get discouraged by how small your thing is today. That was the first part, which is if you create something and the feedback loop is not quite there, you're either going to just willpower your way to keep going. You're going to be a very wise person and say, "Results take time." I'm neither of those things, bad at willpower and not that wise. I kind of know that's the answer, but it's hard. So it's a way to trick yourself. And The way to trick yourself is to say, "Oh yeah, this one thing, it doesn't have to go viral for this to be successful. This is for my binge bank. I know the idea of a binge bank is important. I want to have that as an asset that's there for me. So what are the 10 things that somebody should go consume?" And I started paying attention to that and started putting that together.

One of the things that you are very good at is that I feel like you're just good at learning skills, putting names to them. And This is a good time to dive into the storytelling. So I guess that you had this whole day, you're like, oh, I'm going to go check out Aaron Sorkin. And he always comes back to this one core principle. Tell me about what you've learned from storytelling and then maybe even the meta of how you learn new skills.

The storytelling thing is cool because I think everybody intuitively knows storytelling is a pretty dope ability. And I look for this mismatch between things that have a lot of value, but you're not taught Or even better, it sounds lame to say you're working on it. If I find that, I'm like, "Ooh, this is a good one." Another example of that to me is enthusiasm. Anybody who's been around somebody who's got high energy, enthusiasm, you like that person. That's inherently, it's a very likable trait. Of course, there's an over-the-top obnoxious version, but generally you want to err on the side of have energy, have enthusiasm. Those are people you want to do projects with, work with, be involved with. But nobody will ever be like, "Yeah, I'm practicing my enthusiasm." I'm practicing this. That sentence doesn't even compute. So if there's a thing that has value that other people don't practice or try at, and even better, it's almost taboo or lame to say you do it, I've found that those skills are actually premium skills to me because you almost differentiate yourself in the marketplace. Storytelling is another one of those. Joke telling is another one of those. If you're like, "I am working on getting funnier." They're like, "Are you trying to be a comedian?" No. You like funny people though, right? Of course, everybody does, whether it's relationships, work, content creation, whatever you're doing. If you're more humorous, people will like it better. Nobody practices. So it's like, what do you expect? Just to magically happen? We kind of know everything is downstream of practice. So storytelling is one of those skills where I knew that I loved it whenever I met somebody who was a great storyteller, I wanted to get better at it. So then who's the best in the world at this? That's the next question. One of the people that came to mind when I Googled around was Aaron Sorkin. He's written famous TV shows, I don't even know, West Wing, Newsroom, The Social Network movie. He's great for writing dialogue. And in these interviews, he says this thing. He's like, They're like, "What's the key to storytelling? Can you teach a 3-hour masterclass?" He's like, "I could teach a 30-second masterclass. It's just this. It's intention and obstacle." And he said it even better. He goes, "I worship at the altar of intention and obstacle." And I was like, "I don't even know what the hell he's talking about, but the way this guy's serious about it tells me I need to go dig in. What is he talking about?" So what does this mean? Intention and obstacle is just At any given moment, the hero of the story, whether it's you or someone you're talking about, has to have a very clear intention. What do they want? And under that is why do they want it? How bad do they want it? What happens if they don't get it? That's what goes into intention. And then obstacle, who's in the way? So Harry Potter wants to live. What's in his way? Voldemort's trying to kill him. The most powerful wizard of all time is trying to kill him. Intention and obstacle. And basically, if you watch, if you read any story or you watch any movie, you should be able to pause at any moment and just point at the screen and just say, what do they want right now and what's in their way? And if you ever go 5 minutes without that being clear, people will lose attention, their attention will drift away. And so once I realized that, I made that the central premise of any story. And what I realized was that this was an incredibly powerful tool. It is the fundamental building block of storytelling. And the more interesting thing which we could talk about is it doesn't have to be life or death. All right, everyone, really quick. If you've heard this podcast before, you know that Sean and I think that the most important skill set you need in business is copywriting. And so what we did was we went through all of the podcasts that we've done. It's like 500 of them, and we found all the best copywriting tips, our resources, our frameworks, our templates. We aggregated all of them into one simple document so you can skim it all and get everything that we've ever talked about with copywriting. It's in the link below. It's awesome.

Check it out.

So most people think of it when, like the example I even gave was Harry Potter trying to live and most evil wizards trying to kill him. Okay, cool. But you can shrink that down and actually you get bonus points when you can do intention and obstacle on a lower stakes moment.

So I wanted a croissant and all the places were closed, but I need my croissant.

You need your croissant, but the audience has to believe that you truly needed it. And you got to tell them, be like, you got to make them believe that you really wanted it ideally because you actually did. You don't have to fabricate the story. It should be real. I'll give you an example. I was at an executive offsite. My company had just gotten acquired. I got put on the exec team of this now 2,000-person company and I feel a little bit out of place. I've never worked in a company bigger than 20 people and I wanted to use storytelling as a crutch, as one of my tools in my toolkit. How can I use this to better myself? All right, so we're supposed to go around the circle and say what's been going on or what's something recently that happened that you want to share with the group? Some BS icebreaker. And every single person just did it in a work context. Oh, we're working on this thing, but then this person on my team did this problem or they quit or whatever. Oh, we're working on this thing, but then legal said this. And it's kind of like boring, boring, boring. And I was like, "Yeah, recently I had a big moment, big day." And okay, pause, right? Get people curious. I said, "I just moved out of the house." I was young, right? So I was like, "I just moved out of the house. I'm living in my own place. I've been living there for a year now, but I've never invited my mom over. And my mom's been badgering, 'Why don't you invite me over?'" What she doesn't know is I'd never invite her over because "I don't know how to host. She was always the host if someone came over. I don't know how to do adult things." So people are kind of laughing, but I was like, I had been trying to get her to treat me like an adult, but the reality was I'm not. I'm actually still a little boy. And so I'm telling the story about how my mom comes over and I decide to cook. I decide to cook Brussels sprouts, the most adult food there is. Problem is, don't know how to cook Brussels sprouts. So I'm doing it, blah, blah, blah. And I tell the story of cooking the Brussels sprouts. I kid you not, everybody's entertained. They listen to it. During the break, everybody made a point to come up and be like, "Dude, that Brussels sprout story was hilarious. That was so funny. What was that? What even just happened?" They kind of couldn't even explain it. And for me, it was just another example of using storytelling even on low-stakes moments actually builds likability and fandom more so than the dramatic I was skiing and there was an avalanche. That's cool, but it's unrelatable. And actually there's something fundamentally unlikable about it. And usually if I want to write something, it's because I'm trying to, whatever, I'm trying to have fun, but I'm also trying to build an audience of people who like me or are fans of me or get customers who want to buy my product or whatever. I try to use likability for that.

It was interesting. I was at a sort of a very fancy dinner. It was like multi-billionaire's house. And it was one of those dinners where everyone is like, people had flown in for the dinner and There's an Olympian who's sitting across the table who I was a big fan of growing up, and we're all going around doing introductions, and it's my time to do the introduction. So I'm nervous. I really want to impress everybody. One of my childhood heroes is Monica Lewinsky.

I'm not a sports fan. Yeah, we can relate to a lot, right?

And I put myself up and I talk about, "Hey, this is what I do for a living." And I'm like, "I'll crush it, man. Everyone would love this." and we're hanging out after dinner and back at my apartment. My buddy goes, "Yo, you did the worst job ever. That was a horrible intro." I was like, "What are you talking about? Every word to the bone, had my one-liners ready to go, crushed it." He's like, "No, you were just trying to sound impressive. In a moment like that, you tell a funny story or you make a joke and you lighten the mood.

You did exactly the wrong thing." Yeah, first of all, great friend to say that. Great friend. Great friend. Can we call that out? And you're absolutely right. I learned this from Hasan Minhaj, the comedian, because I was going to go on stage. I was like, "Hey dude, you do this for a living. I don't know how to do this stuff." And he goes, "Comedy is a low status game." So he goes, "You're going to be up on stage and you're nervous, so your natural tendency is going to be to puff your chest out to kind of project this false bravado." But he's like, actually what you want to do is build connection with people and you build connection with people through vulnerability, through low stakes, through low status. Specifically, he starts his comedy special. I went and wrote it out to try to understand what he does. His last comedy special, he starts out, he's sitting on a stool, he's talking about how intention, him and his wife been trying to get pregnant, and they haven't been able to, and they went to a doctor and he's like, "The worst news ever. It was my fault. My balls don't work," basically. Is there a lower status thing as a guy than to be like, "My junk doesn't perform." Also just the way that word choice is inherently funny. Exactly. And so he's obviously a master at this and trying to learn from people who are— I'm in business. I don't try to learn how to be a better storyteller or a better writer from business people. Why would I do that? I would try to learn from the people who their thing is storytelling or writing or entertainment because they're going to be the best at this. Aaron Sorkin, comedians, those are the people I try to learn from. And so I think that was one principle that sounds like you learned the lesson the hard way too.

How is storytelling different for you in writing versus speaking?

It's not that different in general. One of my biggest writing rules is write like you talk. Most people have this false thing we do. I think it's from school. School teaches you, they're like, "Read Shakespeare, write these essays. I need 6 pages minimum, double-spaced, all this stuff. Use a big vocabulary." All the things that don't work in the real world, you learn in school. I think what school teaches you is basically Just pretend. Hey, be something you're totally not. That's what good writing is. In the real world, I don't think that's true. I think good writing is simple. Good writing is easy to read. Good writing is entertaining to read. Good writing has a voice. It's not just this archaic sounding thing. So anyways, one of the principles is write like you talk. So if I'm going to write a story, I will I'll actually say it first and then I'll just write down what I said. That's a starting point for me because for most people, myself included, if you sit down, the blank page of death is the most intimidating thing. It's very hard to even get started. But if you are stuck and you just say, okay, so what is the story? Forget the words. What are you trying to say? I'm trying to tell a story about the one time with the Brussels sprouts and blah, blah, blah. "Cool. What makes it interesting?" All right, great. "Where did it start? What's the start of the story?" "Well, it started when I blah, blah, blah." "And what's the end?" "Well, the end was when this happened." "All right, cool. Sounds like you got a beginning, middle, end. You know what happened and you roughly hit the outline. Cool. Maybe now start writing." And so write like you talk is an important principle. And then the other thing is there are nuances that are different. So for example, in writing, I'll use a ton of parentheses, Because you can't do that in— You can break the fourth wall basically when you write, but when you talk, it would be like me saying, "So we were going this way. We always take that route." It's like that's a parenthesis when you're talking. When you're writing, it's actually much easier to do. But when you're talking, you can use pauses, a dramatic pause. How do you do a dramatic pause in writing? It's kind of hard to do. You have to use line breaks or dot, dot, dot, dot, dot, whatever. You got to try that. So some tools are a little bit different, but I would say 80 to 90% of it is the same to me.

Have you learned anything about the pacing of a story, how you drag it out or compress it? Does that change for different platforms? How do you think about that?

Definitely. I think another misconception is shorter the better. Too long is too boring. And actually, Anything could be any length. It just says you can only be as long as it is interesting. That's a general rule. It can only be as long as it is interesting. If you can go this long, a long blog post, but it's interesting all the way, fantastic. That's the right length. However, you should always try to understand what is your level of credibility or buy-in with the audience? So here in a podcast, you can kind of riff in a podcast. You could be like, dude, we could talk about something we said in the lobby or be like, "Oh, you just had Sam Altman on. Does he have a bodyguard? We could just not talk about writing for 5 minutes." Totally fine. However, if it's cold traffic on the internet, you better have an amazing headline and a first line that's going to hook people and be right about the match to what the headline was because you don't have that reputation with them. So if you know your audience's level of buy-in with you, you can kind of dance around subjects versus be very direct and immediate and try to provide value right away. To hook people right away. So TikTok is a platform where you're swiping, and if it's not interesting the first 0.9 seconds, you're gone. So on TikTok, you see people right away try to say a thing. On podcasts, you'll see people shoot the shit and build, there's a chemistry thing because people aren't going to swipe away from the podcast in the first 30 seconds. It's not usually how people consume podcasts. And so you got to know your medium and you got to know your audience. What's the level of buy-in you have?

How do you think about the hooks for a story? One of the things I've noticed with comedians and really studied is how fast they're able to build context. They can do it in 6 to 8 words where some people just go on and on and on and on and on. It drones. And that hook of how you bring people into the story is super important.

I agree. However, what is a hook? So a hook is basically, it's the first thing you're going to say, it's trying to hook their attention.

Great.

I think actually right now for the type of person who's going to listen to this, you probably have studied a little bit of copywriting maybe, or you kind of pay attention to what, oh, this person's blowing up on Twitter. What do they do? Oh, they write their threads and the first line of their thread is like, here's the unbelievable story about how this Chinese immigrant took a simple thimble and turned it into $10 billion, whatever. Some unbelievable sounding hook that you're like, oh, You have to pick, it's like maximum clickbait. I actually think that hooks somewhat overrated, underrated is frames. So what's a frame? So a frame is you take an idea, an idea can be this big or it can be this big depending on the frame. So I can be like, I don't have a good example off the top of my head, but we'll do one that we just talked about, that Hasan Minhaj, the comedy thing. I told a little story about what he's doing in his opening line. So I could just say, here's what he did at the start of his thing. I could say, here's what you can learn about public speaking from one of the greatest public speakers in the world, Hasan Minhaj. So I could take the same content where I'm going to talk about starting with a low status thing, but I can put it in the frame of this is not just for comedians. This is actually when you're at a dinner party and you're supposed to make an intro, and you don't know what the hell to say, this is how to not make an ass out of yourself. You change the frame. And so I think that more important than a hook, which is just like a grab you by the throat attention grabber, is think about how you're going to frame your ideas. Hooks are about the words you're going to write. Frames are about the idea and how you're going to make that idea relevant and how you're going to connect two ideas that seem unrelated. To be related. The real great writers, I believe, are great at framing their ideas more so than just coming up with that perfect one-line hook thing that's going to just trick the person into clicking.

Yeah, let's get super concrete here. So you wrote a super viral thread on Clubhouse, and this was the standard way to do a frame. So it says, one parenthesis, 'Clubhouse existential threat number 1, time to value ratio. Let's brainstorm.' And you're like, jargon, fancy words.

I don't like that. That wasn't me writing it. That was somebody else. Yeah, exactly.

Yeah. I don't like it. Brainstorm, no storyline. And then it didn't do that well. And you come in, you're like, 'So... everyone seems to think Clubhouse is the next big thing, but I think it's going to fail. Here's how I think it all goes down.' Yes. Why did you choose that?

So if you compare the two and on your YouTube, you should put these side by side so people could see it. The other one was written by this guy Chris who created an app that was kind of like Clubhouse, went super viral. It was called Secret back in the day. I don't know if you remember this. It's called Secret, went super viral. They raised $100 million. The founder sold some secondary, bought a Ferrari. It was the hit product for a very short window of time and then it died. So if anyone has the credibility to say why Clubhouse might fail, That guy was actually the guy. The problem was he was extremely dry, told no story and just said and used very 12th grade reading level jargon like Clubhouse's existential threat, the time to value ratio. Immediately felt like homework. Whereas my thing was everybody thinks X, but I think Y. And the most important part was Here's how I think it's going to go down, not here's why I'm right. So here's how it's going to go down is basically like gossip. It's story. Here's why is logic and rationale. So that's kind of why I wrote it that way was, and then the rest of the thread, the reason this thread got 20 million people to read it was because I wrote it almost like a screenplay. I was like, I didn't say, here's the 5 problems with Clubhouse. I wrote, You're the founder of Clubhouse. First of all, fuck yeah. You're winning. Everybody's talking about your app. Your app is cool. Kanye's in your DMs. VCs are throwing money at you. And I set it up, right? That's the setup. That's you right now. And already, you know, if you're reading that, this is not how most business tech Twitter writing goes. Most business tech Twitter writing goes is it's an intelligence contest. And I was telling a story. And so that's why I think it worked. I think if I had written it with me trying to be the 9,000 IQ guy in the room, it would not have worked.

So when you see people, say that I'm writing now and I'm like, all right, I'm not going to do intelligence contest. I'm going to try to do exactly what Aaron Sorkin said. There's intention and there's obstacle. I'm going to frame what I'm saying in terms of story. I'm going to focus on the frame and say that my writing still, it's just like, yo, this is lame. What do you think is going on there that makes it feel dry or it lacks a sense of momentum?

Well, in the same way that comedy is great, but not every line should be a joke, storytelling is great and not every piece of content needs a story. So I think one challenge is I wrote that one as a story, it did great. That doesn't mean everything I write online is screenplay story type of thing. That worked in that situation. It's not going to work in every situation. So you got to know The tools and when to use them. Hammer's not good if you're just trying to open a door. Sometimes a key is what you need. And so that's the first thing. Don't just force it in. The second thing is you probably need reps. I don't know, I've done this a lot of times. That wasn't the first story I've ever written. So if you're like, "Cool, I'm going to get better at storytelling," be prepared. Tell 100 stories starting with maximum cringe and get to not cringe, but it's going to take 100. Expect that it's going to take 100 stabs at this and specifically 100 intelligent reps. So it's like, do it. And then the next one you have to be like, what could I do better? Oh, my hook was a little weak there. Or, oh, it droned on too long. Or, I don't really have a point. Maybe this shouldn't have been a story. Maybe it should have been something else. And so 100 reps where each one you try to say, what's one thing I could do better than last time? Just one thing. That's it. And then you just keep going. And if you could do 100 of those, then I bet your stories will work. It's not going to feel forced because you'll learn the skill through those 100 reps. This is the MrBeast-ism of, he's like, everybody asks me, how do you do YouTube good? He's like, I tell them all the same exact thing. Make 100 videos and every video do something better than you did before. Anything. Doesn't even matter what it is. One thing better than before. Do 100, then come back and talk to me. And he's like, two things happen. First of all, nobody does it. They all wanted just some answer. They had no intention of actually going and Doing the work. And then of the few people who actually do the work, they never need to talk to me again. By the 100th one, they figured it out. They're doing great. They never come back for advice. That's why it's the perfect advice to give someone because it's true and it saves both of us the hassle if you actually followed it.

Yeah. What did you learn from Storyworthy?

Storyworthy is an amazing book by this teacher guy who's the 20-time storytelling champion of the Moth Storytelling. I didn't even know what this thing was. But whatever, if you're the champion of something, I paid a little bit of attention. He's got this book and in the book it's basically how to tell better stories. I would say probably worth reading the book. He's got one thing that I really took, which was stakes. So he's like, every great story needs stakes. Meaning if the story is intention and obstacle, but if you don't make it clear what's at stake for the person if they don't get it, then the story's not going to be very compelling. So when you tell a story, let's say it's the— and it doesn't have to be high stakes. He's actually very— again, the other thing he says is don't tell— he calls it vacation romps. So it's like, don't just tell a story about this great night you had, this party, because nobody cares. Nobody wants to hear about your vacation. Nobody wants to hear about your cool college party you went to. Just fundamentally, those are bad stories. The second thing is A great story is not just, I was swimming in the ocean and a shark bit me and then I survived. It doesn't need to be extreme. And again, it's actually almost better if it's not, but you still need stakes. So how do you have stakes even if it's not a shark biting you off? And his answer was, the stakes come from the emotion. So as long as you believe that that other person was going to feel a certain way, then the story has stakes. So for example, if I'm trying to impress my mom doing the Brussels sprouts thing, Embarrassment is what's on the line. I'm going to be embarrassed and my ego's going to take a hit. So as long as you believe that that's true for me, the story will be entertaining when I actually tell it, when it's actually delivered. The other one he says is, he goes, "What is a story? A story is a 5-second moment of change." Whoa, what does that mean? A 5-second? So he's like, everything you tell in the story comes to this one moment, this 5 seconds where the character's transformed. I use movies because it's easier that most people don't have a big archive of writing in their head, but we've all watched the same shows and movies. Every rom-com is some version of the following. The guy's a player and he's never going to settle down. That's the start of the movie. Or she's a high-powered lawyer who's doing great in her career, but never made enough time for love. That's always the start of the story. There's only two rom-coms, right? She was in love. She thought they would get happily married. He broke her heart, start of the rom-com. Well, guess what the ending of the rom-com's going to be? Always the exact opposite of that. If she was the high-powered lawyer who never made time for love, she's now going to be in love and she's going to actually quit her job as a lawyer and open up a bakery. That's how the movie's going to end. Or if he didn't want to settle down and he was a player, by the end, he's going to be chasing her and he's going to propose to her. He's going to want to settle down. So spoiler for all rom-coms ever. And it's actually all movies ever. Die Hard, Jurassic Park, you could do the same exercise. Watch the opening 1 minute. The end is going to be that character, the opposite of his current lifestyle or belief system or habits. Scrooge hates Christmas, he loves Christmas or whatever. Every movie, every story is the same. So the heart of the story is the 5-second moment when they actually made the transformation, when they switched. And it's usually when they lost it all, when they had the heartbreak, when they hit rock bottom, when they had no choice but to be brave because they were finally cornered, whatever it is. You know in Batman when it's like he's in the cave and he's got to get out and nobody's ever made it out? I don't know if you remember this part of The Dark Knight or one of the Batman movies. And the mentor was like, "Only one person's ever got out." He's like, "How did he do it?" He's like, "He didn't use the rope." Basically, he jumped with no safety net. And so the 5-second moment of change is the character climbs up the thing, takes off the rope. If he doesn't make this jump, he's going to die. But actually, because of that, makes the leap and actually makes it. That's the transformation moment. Everything is based, all stories, if you don't know what's the 5-second moment of change for the main character, you don't really have a great story.

How does this apply or not apply to the story of a company? If I'm trying to tell the story of Rite of Passage or you think of all these companies, oh, we started in a garage, we had no money, this is what we believe, right? You have Airbnb, you have the Obamas, and then you have Brian Chesky who's going to the houses and he's taking photos with his own camera. He's doing the hustle. It's like these founders really believed. So how do we take these ideas and apply it to what we're building?

The origin story of all of Silicon Valley companies is similar. So let's take Airbnb, for example. What was the moment of change? The moment of change, the origin story of Airbnb is we were broke jocks who had nothing, right? The beginning of the rom-com, we were broke jocks. Not only did we not have a successful company, we didn't even have an idea. So we were the worst situation for an entrepreneur. No money, no team, no idea, no respect, no reputation, no nothing. Even worse, wrong founding DNA. We were all designers and the narrative was you got to be an engineer to build a, you got to be a developer to build a tech company. And so, well, the moment of change was basically, I think they had no money, they didn't have enough money to pay rent or something like that. So the moment of change was basically one of them had a crazy idea, to be like, "Hey, what if we rent out our space here for this? There's a design conference in town. What if we create a bed and breakfast for people who are coming because all the hotels are sold out?" Bed and breakfast, we don't have a hotel. And they're like, "Well, we could just put an air mattress here." And they laughed and they were like, "Whatever." And then 3 people came, stayed, paid the money, and had a great time. And they're like, "Holy shit, this might be a thing." And then there's several holy shit moments. There's We ran out of money again. So we did the Obama O's cereal thing. They tell the story about when they were getting knocked off by the Samourai Brothers of Rocket Internet. They were cloning their company and going to kill them. And he tells that story. It's like, we faced this life or death moment and then we had to make a decision and we changed. We went from being scared to being like, all right, we're going to compete with these guys. We're going to beat them. And that's the moment. That's That's what each of those micro stories is about. The way I've learned this is you have what's called signature stories. So your signature stories are the 4 or 5 stories that if I only could tell you these 4 or 5, you would know everything there is to know really about me. So for example, your origin story. For you with Write of Passage, what's the origin story? I'm assuming you didn't just create this because life was good, you already were good at everything, And there must have been some moment where you were like, I got to do something here.

Will you help me improve my origin?

Yeah, give me what it is right now.

All right. So I worked this job at this New York advertising agency and I was super intimidated by my boss. He's like 6'4", big beard. He's just not like super welcoming guy. Super talented, super talented. And I wasn't doing super well in my job and he sort of calls me into his office and I was working on a pitch deck for McCardy. I was trying to be all impressive and stuff like that. And I wrote in the pitch deck that the idea that we had was going to be epic. And he was like, "Yo, that is not a good word to be using. You're not..." He said something to the effect of, "You're not in college anymore. We don't write like that here." And then through writing that sentence, he then started saying, "Hey, you really need to improve your writing. You're just not a good writer." And I was like, "Well, I tried learning to write in school. I don't even like writing. My whole job is writing and I got to get good at this." So that was in November. Then we go through December, I get a raise. I'm like, "Oh my goodness, this is going to be great. Life's going well." Then January 5th, 7 months out of college, I get laid off. And of course in my head I'm like, "I got laid off because I'm not a good Writer. Uh-oh, I got to learn this craft, but I don't even like writing. But then I'm seeing all these people who are good at writing and they're just making moves on the internet and stuff. So I spend years, 2, 3 years, and I'm learning how to write. I start building an audience. And during that time, people reach out to me. They're like, "Hey, you're pretty good at this. Can you start teaching me how to do it?" And I'm like, "Wait, I learned all these things on my own. I had to figure these things out, out of desperation for how to learn how to write." Then that led into Rite of Passage, and that's how the company got started.

Okay, great. So let's workshop that. Cool. All right. So let's go back to the origin. So there's a beginning, middle, and end. Beginning, your start of your rom-com, you're working in a job, you said you're not doing so well, your boss kind of embarrasses you, and you end up getting laid off. Act 1 of the movie. I think just to make that part better, so I think you have the element there. Act 3 is So we know act 1 is going to be, don't like my job and my job doesn't like me. Even worse, my job doesn't like me. Second part is I'm not doing so well and I'm kind of embarrassed and I'm kind of intimidated by my boss. Great. Super relatable, super likable, all that. You have a moment where you got specifically embarrassed around the epic thing calling you a college kid or whatever, and you're like, okay, hopelessness. Max Payne got laid off. Cool. And I'm sure you had some feelings about that. Act 3 is now I get paid millions of dollars to teach people writing and I'm doing a podcast interviewing my writing heroes and they're like, "Dude, you're awesome. I'm a big fan." Okay, great. So we have the element of an amazing story. How do we actually make it better? So the first part is your Act 1, you didn't focus on the pain enough, the intention and the obstacle and the feelings you had at that time. So for example, you said, "I wasn't doing too good at the time." And then you're like, "But then I got promoted or a raise, so I don't know what that is." You might want to leave the promotion or raise out. Doesn't really add to the story. It's confusing, conflicting messages. Never let the truth get in the way of a great story. Let's start with that. So why did you not think you were doing well?

The company was constantly trying to figure out what do we do with this person? I can't believe this happened, but he literally brought me into his office and he goes, I need you to stop thinking like Jeff Bezos. And I was like, can you explain? He's like, do your job. You are a sales guy. Focus on that. I don't want you focused on the future of media and where that's going. And so there was just a lot of tension there and he and I never really got along that well.

Right. So yeah, I think you want to find— I bet if you zoomed in, go back to the memory bank and you remember any moments where you felt the opposite of how you're going to feel at the end. At the end, you feel really proud and you've accomplished and you've overcome. But at the beginning, you probably felt embarrassed, somewhat insecure, whatever. So for example, if you were like, "Yeah, I remember there was this new guy that just got hired and I was training. I was trying to welcome him and train him a little bit, and then he got promoted before I did. And I was like, 'I'm doing something wrong.'" Or, "At my performance review, I remember there's a category for pros and he had 3 words and then cons or whatever." Needs improvement was huge. A little anecdote like that, I think will make that more real of what was the moments where if you said I wasn't doing so well, that it really hit home for you, something like that.

Let me just wrap everything we've spoken about into what I'm gathering is it's the rom-com. I got my beginning, I got my end. I want a perfect yin yang between them. Then what I want is I want to build up to those 5 seconds of change. So I want One emotion lead up to that change. That is the moment of tension where something pivots. Then I get to the end, there is the opposite. And then what I want to do is intention and outcome?

Obstacle.

Intention and obstacle. Thank you. So my intention is I want to be good. I want to be good at my job. I want to be valued. I want to be respected. Actually, I could even bring it into, I want to be a worthy human being. And I'm in my first job and I'm like, "Dude, you have no skills." So I have that. And I'm like, my job is about being a writer and my boss thinks that I'm not very good. So now I have my obstacle. So that's sort of what I'm getting from you.

Right? Yes, exactly. You nailed it. Now let's go to the 5-second because what you said was basically some version of you were like, the beginning was pretty good and the ending was pretty good. The middle you were like, so then I got laid off. And so then I started thinking about, well, I want to improve my writing. Sounds like an arbitrary epiphany. Maybe there was a mentor that told you something, or maybe you read something online that inspired you, or maybe you had a long talk with yourself on a long walk one night and you were like, "You know what? Screw this." Probably a moment when you decided, "Actually, I'm going to get good at this." That's usually a very important part of every story. It was like, what triggered the turnaround? So you want to know that and then you want to explain that part. And then you basically were like, And then I got better and then everything was great. And it's like, whoa, whoa, whoa, you fast-forwarded the montage too fast. What triggered the turnaround? And then what'd you actually go do? And not in a long specifics, but what's the first thing you started to do to get momentum? And then what was maybe some resistance you felt that you overcame? Because the Pixar rules for storytelling, I don't know if you've seen this.

22, yeah.

The most important one, I don't know what the 22 say, but I remember one which was something like, "The hero doesn't have to win. The audience loves the hero because of the way they try." And that was really important to me. I was like, "Oh, that's right. Every underdog story is lovable because of how hard they try." And if somebody just tries something and immediately it works, that's not a very good story and you don't feel good for them. So you got to say what you tried, what resistance you felt, and then how you overcame that resistance. It doesn't have to be a long thing, but you want to make it feel real. And the last thing I'm emphasizing to you that I think anybody can do in their storytelling is you're not saying what happened, you're zooming into moments to explain how you felt with ideally some relatable visual or audio moment. So it's like, "I remember he said this to me and I'll never forget these 3 words. He said," whatever, some sentence or I remember looking around and there was nobody else there. Tony Robbins, I'm a big Tony Robbins fan. He does an amazing job telling his story. And he's like, I remember sitting in my apartment, I looked in the bathroom and I was doing, because I used to do dishes in the bathtub because my dishwasher didn't work. So I'd soap up the bathtub. All he's trying to say is I'm a loser. I was a loser. Now I'm super successful. Why? Because I'm Tony Robbins and I figured it out and you can too. But first he has to convince you that he used to be a loser. Otherwise, the whole Tony Robbins shtick doesn't work. So he's like, how do I convince somebody I'm a loser? I could say that I wasn't doing too well, or I could say that I used to have to wash my dishes in a bathtub because that paints a picture of a loser. He's like, I remember I was sitting, and he says, I was sitting in my apartment and I didn't have any furniture because I didn't have any money. So I just had this one chair. I didn't have a sofa. I had a hard chair that I used to sit on. He's like, it was just a chair. He's like, and I remember a song was playing that was like, There's some song where he is like, "I don't have a friend or something like that. It's only me in my chair." And he's like, "Dude, that's me. It's just me in the stupid chair." And he's like, "So I went for a run." And he's like, "Even though I hadn't run in years, I was overweight, I went for a run. And even when my lungs were burning, I was like, no, you may be a loser at all things in life, but you're not going to lose this run." And he tells a story and it's inspiring when you're hearing this. And he's just zoomed into one moment that's visual, that's audio, that's a feeling. And he's convinced you of that before state so that the after has some impact.

The two things that I'm getting there is first, you can tell a story. A story is not a record of what happened.

Absolutely.

It is not you saying this happened, this happened, this happened, this happened. It is almost this—

It's transformation.

Oh, interesting.

A story is just a change. The world was one way and then it was another way. I was one way and then I was another way. My company was failing and then it was succeeding. All a story is, is just change. You only want to include the what happened so much as it explains how that change came to be. Yeah, it's not just a timeline of events.

And then you're also really cueing into emotion.

Yeah. How come? That's what people respond to. In my writing course, I used to teach I used to teach this one thing that I was like, you want to work backwards from the emotion. I learned this from a guy who used to be my intern or something like that. We hired him when he was 20 years old, Steve Bartlett. Today, a lot of people know Steve Bartlett. He's got a big podcast called Diary of a CEO. He's built a company, he's done a bunch of things on Dragon's Den. He's a famous guy now. I met Steve when I was 20. All right, when he was 20, I was 25 maybe. And he flew from the UK, he lived in our office, slept in our office and he wanted to work with us and we worked together for, I don't know, 9 months or a year or something like that. And Steve was awesome in a bunch of ways and he was obviously just a 21-year-old in a bunch of other ways. But the awesome thing I remember was he was like, he told me something, he goes, "I just think about what is Jenny in her bedroom going to think when she sees this?" I go, "Who's Jenny? What are you talking about?" He's like, "Oh, if we're making a piece of content that's going to go on social media, Social media is Jenny in her bed laying down, just scrolling, just swiping. And she's like, basically this has to make Jenny stop, think something, and share this with her friends. Otherwise it's going nowhere. There was no point in writing this thing or doing this thing because it created no reaction from the person. They're just going to keep swiping. The world is full of infinite content. We only stop at things that we have some reaction to. And So I stored that away and then I heard the same idea from another person. This is how you know a good idea. The BuzzFeed guy goes, "Everything we do at BuzzFeed is about Debbie at her desk." I'm like, "Jenny in her bedroom, Debbie at her desk. What's going on here?" He goes, "The most powerful network in the world is the bored at work network." BuzzFeed was growing like crazy at the time. He's like, "BuzzFeed basically taps into if someone's bored at work and they just want to have a distraction for 5 minutes. We want to make a piece of content that will distract them and get them to forward it to a bunch of other people who are also bored at work. And that's the whole network is the bored at work network. All right, second time I heard the idea. Then I heard the idea a third time. This guy, Chris Quigley, he ran an advertising agency that would make videos go viral. And at the time I was like, going viral is like a lottery ticket. How do you do a viral video? I don't know. It's just like something amazing must happen. So I go, "What's your hit rate on virality? 1 out of 100, 2 out of 100?" He goes, "No, 8 out of 10." I go, "8 out of 10?" And he's like, "Yeah, look." He showed me their views. I was like, "How do you do this?" He's like, "Well, over time, the more viral videos you make, you have a base of an audience." But he's like, "That just gets you, some people will see it, but how viral it goes is how much they share it." He goes, "So what we do is we work backwards from an emotion." He goes, "The only things people will share is things that are LOL, WTF, OMG, AWW, all the acronyms for all the emotions. So like, oh my God, wow, like, hahaha. If it doesn't do that, nobody will share it. So he goes, we first start with, this is the desired reaction we have, then we'll write a script or write a blog post or whatever, and then we'll go check, do we think that's going to create this reaction in somebody? No? All right, "Let's juice it up. How do we make it more funny? How do we make it more outraging? How do we make it more endearing and heartwarming?" Whatever those are. And so once I heard that 3 times, I was like, "Okay, I get it. I need to create a reaction out of the average person just in their bedroom or at their desk, and I need to start with the emotion, my target emotion, and then work backwards from that.

Write the thing that will create that emotion." Yeah, it's funny because when you write, you're like, "Okay, I'm publishing this on the internet. Bunch of people are going to read it." get a big audience. And so you think of, hey, there's all these people, but actually you're just writing to Debbie in her bedroom or Sally at her desk, and people consume your content alone. And when you're writing, you are writing to one person in one place at one moment in time. And you have to remember that because the nature of the connection that you're trying to make is different. And to double down on that idea, in a lot of our media environment, especially with a platform like Twitter, when you scroll Twitter, you're on the throne, you're on the bus, you're waiting in line, your friend's 7 minutes late, you're like, "Come on, where the heck are you?

I'm trying to—

reservation's coming up." And you're just sort of browsing, browsing, browsing, and your brain's only halfway on. And if you can really first understand your own state when you're in that environment and then write to the person who's in that state, now you have a very keen sense of Who is this person? And you're writing for one person, even though if you're looking, you're seeing, hey, 119,000 impressions. Those are not 119,000 people at once like a football game. There are 119,000 individual people at 119,000 individual instances in time. And if you think like that, you communicate very differently.

Yes, perfectly said. You're writing to one person at one moment in time. That's, I think, a very good point. And the other thing that this reminded me of is, do you know this person, Miss Excel? Have you seen this person?

Yeah.

So she, for anybody who doesn't know, she's basically like an Excel influencer, for lack of a better word. She basically teaches people Excel tricks. But the reason she got popular, she went on TikTok, she started dancing while putting an Excel trick on the screen or a tip on the screen. Weird combo, but it works. I was reading some interview with her and they were like, "How do you create your content? What's your process?" I was like, "Oh, I'm curious what her process is." And she goes, "Oh, I don't." She's like, "It's kind of weird." She's like, "Most people, if you say what's the process and they're like consistency, wake up at a certain time, start right away, you got to write every day, you got to post at a certain time, you got to do all these things." She's like, "I don't do any of that." She goes, "I literally first just change my own energy." She's like, "I'm kind of woo woo woo in that way, but I basically get myself into a peak state of mind. I get myself into a certain mood and a certain state of mind where I feel magnetic. I feel charismatic. I feel energetic. I feel, it's literally like a science called energetics. She's like, I work on my energy and two things happen. One, ideas start coming to me much faster than if I sat down and said, what are some ideas? I need to post some content today. And so she's like, I just work myself into that state. I let ideas come to me. An idea will hit, and as soon as it hits, she's like, "I run to my phone, hit record, and I just do it." She goes, "Because I believe all content is just energy transferred through the phone. It's my energy shifting to you, my emotion, how I feel about this. If I feel excited about this insight that I have or excited about this tip that I have, I want to get you excited about that tip too. And the best way to do that is for me to be there first." And I think this is a very underrated thing for writers because most writers, They're not performers. All performers know this. No athlete goes on the field without being warmed up and being hyped up. No stage performer goes on stage just kind of cold and low energy. But almost every writer starts cold and low energy and just sits there somewhat miserably. And there's even some weird glory from this, I don't know, this pain that's martyrship of how you need to be as a writer. I think that's all stupid. I think it's very similar to performing in any other way. I think you should get yourself into a great state of mind and then have that energy and then sit down and write and let it flow and let that energy rip through you so that the other person who reads it is going to feel the same excitement you have about the insight or feel the same excitement you have about this plan or whatever it is. You want that to come with it.

And a lot of times when people write, they have this idea, they're away from the computer, they're at the bar with their friends, they're on a walk with somebody else, they're at Thanksgiving dinner. They're like, "Man, Auntie Diana, she has no idea what's going on in the world. That woman was crazy." And you're so annoyed at 11:00 PM at Thanksgiving, and then you try to write 3 days later. And the problem is they're not capturing the energy that MsExcel is capturing before she does the videos. And people end up writing in such a sober state that their writing ends up being boring and sterile.

100%. The thing I said at the beginning of this podcast where it was like, I look for things that I think are important that other people don't practice, overlook, or would be too embarrassed to say they're working on. This is an exact example of one of those. Nobody wants to work on their state, their energy. Miss Excel does. She's like, "I'm going to make myself magnetic before I make content." Well, I like that. That's pretty cool. I don't even know what that means, but that sounds provocative, right? Okay, it's better than whatever the hell I'm feeling when I sit down to write. Okay, that's a new standard for me. I'm going to do that. And so I think most people would probably in their heart believe that this is true, that if you got your energy right before you did the thing, it'll probably turn out better. Nobody's going to do it, which is the best part. It's the arbitrage. It's how a less talented person like me could do really well.

Wait, so hold on here. Stop the podcast. So what should I do next time I sit down to write? How does this actually work? What am I going to dance, do some jumping jacks? What do I actually do?

Yes, exactly. That's exactly right. So state change is 3 things. Number one, radical change in your physiology. So you could sprint, you could do pushups, you can dance, you can do 20 air squats, you can dump your face into cold water, whatever it is. It's the fastest way to change how you feel is a radical change in your physiology. It's the first thing. So do that. That's the very first thing. I have a friend who's a professional poker player. He does the same thing. He goes, poker players are notoriously degenerates. Literally sitting there in a casino, which is the worst air-pumped-in environment. There's no windows and you're around other degenerates all day. People are smoking. It's bad. He's like a monk. And during a tournament, in the breaks, he goes in the parking lot and he does wind sprints. He's not doing it to be a better runner. He's not doing it to increase his VO2 max. He's doing it because he wants to make a better decision when he gets back to the table. He knows he makes better decisions when he changes his state. And that's part of his edge. That's why he's been a European Poker champion and a tour champion several years. So first thing is a change in your state. The second thing is a change in your focus. So what are you even focused on? The way I imagine is I have this laser beam of focus. I don't know if this is true, but it's what I've convinced myself, which is if I just turn my attention to this, I will crush this. This will be amazing. If I put 100% of my focus on this podcast right now, oh, this podcast didn't stand a chance. And the only limit to me is just where I'm pointing the beam. And if I'm trying to point it in 5 different places or whatever, that's going to be a problem. This also works with if you have to write something and there's a deadline, if your focus is on the deadline, it's the wrong place to focus, right? If your focus is on how hard it is for you to do something, if you're focused on how hard it is, it's not a good place to focus. You need to focus on the thing you want. So don't focus on the wall where you're trying not to crash. Turn, right? Basically focus on where you're turning. And then the last one is basically your story. So what's the story you tell yourself? We all have some story that we tell ourselves. And if you improve the story, you'll change the state of mind that you have. So if I go into this podcast right now and my story is, I'm doing a favor to David, I'm just doing this. Oh man, I had to drive an hour to come here and this means I'm not going to be able to do this thing and whatever. That's the wrong story. Obviously, I'm not going to perform very well. I'm not going to be at a peak state. Whereas if my story was, there's going to be someone who listens, one person, one person who's listening to this podcast and they're going to hear one thing that I say, one story, and they're going to be like, "Wow, I can't unhear that. That was amazing." And that person's going to go and do amazing things. They're going to write me a letter one day and be like, "Dude, that podcast you did changed my life. I'm going to approach this podcast differently." Different words will come out of my mouth if my story about what's happening is different. So similarly, if you want to basically change your state, physiology first, focus second, story third.

Nice. One of the moments I had around story that I thought was really revealing was I work with a coach and we were talking about my writing and I was in a slump. I was down.

What's a writing slump? What does that mean? I just wasn't vibing. I wasn't feeling it.

I just wasn't proud of the stuff that I was doing and I couldn't get inspired. And he said, "Well, what is it that you want?" And I said, "Well, I used to write these pieces, these long-form pieces that I was really proud of. You know what I want? I want to be a creative force. I want to be a creative force. That's what I'm going for." And I sit down to write. I'm like, I want to be a creative force. That's what I'm all about. And he's like, hold on, hold on, hold on. Stop the train. You said you used to be a good writer and you would get in a great flow. What did you do back then that you don't do now? I was like, huh, actually it's pretty simple. I find an idea, That was interesting. I would try to figure out that idea for myself, and then I'd figure out for myself and I'd say, "Well, then I got to share this with other people." And I just do that over and over and over again, and I never stopped. That's all I did, and that's all I focused on. He's like, "Hold on. What you're saying is now you're focused on being a creative force. That's your story. That's not working for you. Let's get back to finding an interesting idea." Not judging the interestingness, figuring it out for yourself, and then sharing it with others. Ever since that, no more slump. All that was, was a change in my story.

Yes. Amazing. That's amazing. And I think the other part of what you said there, which is letting curiosity be the guide, the driver, sounds very simple, but all great ideas are actually quite simple. It's the beauty of them. I think there's a profound benefit of revisiting simple ideas and then saying, am I doing those? I don't look for new ideas as much as I look for ideas I've already heard that I haven't fully actualized yet. And that's one. You've read Paul Graham wrote this essay, Great Work. I'm assuming you've read that one. Yeah. I read it two nights ago.

So good.

For the first time. He wrote it a year ago and it was 13,000 words. So I was like, I'm not doing that. This is too long. Well, when the student is ready, the teacher appears. So I'm thinking about what do I want to work on right now? How do I want to do this? And I went back to that. And in that, he has this great line. He goes, if I had to boil down all great work into one word, it would be curiosity. And he says another thing, which is curiosity drives a level of excitement. It goes an excitement Excitement is really a great indicator. He goes, excitement is the engine and the rudder of the boat. It's the engine in that excitement is motivating. It's a driver to get you to go do things, but it's also the rudder. It also can point you in the right direction. If you don't know which path to choose, just choose the one that's most exciting. Just keep following that and that will lead you to the right place. Excitement is the engine and the rudder, I think is a really powerful idea. And every time I've drifted away from that, like you did, I start with that, good things happen, and then I'm like, "Ooh, now ambition is the driver," or doing something that sounds cool or important or money is the driver. And then all the bad things happen and I'm like, "Shit, why aren't these working?" And it's like, "Well, because you stopped doing the working formula, which was leading to all these great things because you thought you needed to do something different." And so many people are like, "Oh, I hate writing." And most of the time, it's that they associate writing with doing things that they don't want to do.

And then when they think about, well, it's time to write, they subconsciously don't allow them to write about the thing that they're the most curious about or excited to write about. Because in school—

That's not what you get to do.

Yeah. No one's excited about the average school paper, maybe one or two things, but people just aren't trained to think like that. One of the things that I need to reconcile with you and try to sort of figure out, because I've got two Sean ideas and we need to figure out how they sort of come together, is this line that you have, "If you're in your head, you're dead." Love that line. So good. At the same time, you are always deconstructing things. You find something that you like and you're like, "Hold on, what's going on here? Let me try to break it down. Okay, I'm actually going to go check out this book, go talk to this expert, try to figure out what's going on." So how is it that you are deconstructing, thinking, being fairly analytical, but at the same time not getting in your head? Those things feel like polar opposites to me.

Yeah, two things. One, I read something yesterday, this mini book online that was called, I think it's called A Technique for Coming Up with New Ideas. It's some old book. And in it, it said this thing. He goes, "The most valuable traits you can have sound like opposites if you pair them together." So he goes, "Imagine an entrepreneur who is both visionary and detail-oriented." That's a Steve Jobs, for example. Steve Jobs is famous for being a visionary. He doesn't ask the consumer what they want. They just want faster horses. They want a car actually. That's how he admits the iPhone and it figures out what to do, but he's insanely detail-oriented where he's like, "What does the inside of the box look like?" And they're like, "Dude, Steve, nobody's going to look at this." He's like, "I'm going to look at this. I will know what's inside the box. It needs to be beautiful at that level of detail, pixel-level detail." Same thing for all things. I consider myself a creative person. I'm also highly analytical with data. Sounds like opposites. And so there are many things where The exact opposite, if paired together, creates a 1 1 3 type of reaction. And they're often presented as false choices. You're either this type of person or you're this type of person. Screw that. Be the type person you want, which sometimes means having both gears and knowing when to go into which gear. When do I need to be creative? When do I need to be analytical? When do I need to be hard-charging entrepreneur? When do I need to be silly, playful dad, paint my nails, whatever? I have to have these gears to have the life I want. Similarly, you want to be in your head at the times it makes sense to be in your head. The brain is a valuable tool. It just cannot be the master. So I need to be in my head when it's about, maybe it's analysis, maybe it's, oh, I'm feeling fear. I need to actually use logic and ask myself, is this fear even true? And what's the probability of that? And if that happened, how would I handle it? I guess I would just do this. I guess it's not so scary after all. So usually if the problem is emotion, you can solve it with emotion. If the problem is logic, you can solve it with logic. And so I try to use them at the right times. The If You're In Your Head, You're Dead is basically more of a life philosophy than it is a work philosophy, which is people who go around life not feeling a whole lot and not being present in the moment, they're in their head about stuff. They're missing life and that's a problem more so than a writing tactic.

Have you ever seen that advice from Ray Bradbury where he says, "Don't think"? You ever seen this?

No.

So I heard that, what you said here, and it immediately reminded me. He says, "I have a sign at my typewriter. It says, 'Don't think.'" And I'm like, "Okay, that's interesting." He's like, "I'm trying to surprise myself at the keyboard, and the only way to surprise myself is Once I'm in my head, I can't do that. And I think that a lot of writing a first draft is like this. You're trying to get outside of that part of your brain that judges, that condemns, that says, "No, no, no, it's not good enough," and just put stuff onto the page. And you know that you're doing it well when what you're doing is like, "Whoa, where did that come from? Where did that come from? Where did that come from?" And then the question is, how do you engineer yourself to do that? For me, if I'm sitting and typing, can't do it. My ideas, that for me is where I do editing. The thing that was game-changing for me was voice transcription getting really good because now I can stand and talk.

Talk and walk.

Go outside, walk and talk, just blah, blah, blah, blah, blah. Half of Austin definitely thinks I'm some sort of crazy psychopath kind of guy. But you know what? It's made my writing better. And a bunch of people I work with, they're like, "How do you just bang out first drafts so fast?" I'm like, "Because I don't sit and type like everybody else does.

I just go for a walk." Yeah, I think that's a great point. I think you need to figure out a way to engineer that for yourself so you can consistently have it. I think everybody's got a different version of how to do it. What you said reminded me of something though. You're talking about Ray Bradbury, "Don't think." I think this is a very useful troubleshooting tool. So when you're stuck, many ways to get unstuck. And one way to get unstuck, like I said, Radical change in something physical, you do. I think that's a good tactic. Music is a good way to get unstuck too. But in general, a philosophy for how to get unstuck is if you're stuck in the specifics, go general. Meaning if you're stuck in the logistics of the how something is going to happen, it's not quite adding up. What you got to do is not just keep trying to do this. You can just zoom right out. Go super general. All right, super general. What am I trying to do here? I'm trying to do this. Super general. If I had all the superpowers in the world, well, how would I do this? Super general is just like, who's somebody who's done this before? Or super general, okay, I don't know exactly what type of thing I want to write. What inspires me? The way to get out of these sometimes is to go general. And so even if don't think is hard because it's very hard to turn off the brain, but it's not so hard to redirect the brain. And so redirecting it, I think, is a useful tool. You can redirect it towards, I'm going to I'll go rock climbing, I'll go exercise. That'll take my brain off of it. It can also be I'm stuck in the muck here and I need to just zoom out and that's it. Or if I'm stuck in the general, so for example, sometimes I'm stuck in the general of what do I want to be in life and what do I want to do and who am I and all this stuff. Specific, what's the best idea you heard in the last 2 days? If you were going to write about that, what would it be? Or what's the most interesting phone call I've had? Then you go specific because you're stuck in the general. So it's a very useful thing to do is just to get unstuck. If you're stuck in the specifics, go general. If you're stuck in the general, go specific and you'll redirect the brain.

I want to switch over to talk about voice. You're really good at putting your voice onto the page and you do something very specific that I'm not sure how consciously you do this, but you're so good at getting inside the head of a reader to understand, all right, how are they feeling about this in the moment? And basically, you said it earlier, breaking the fourth wall, and then by doing that, building trust and connection, and then it creates this friendly casualness as if we're having a conversation that, my goodness, that is levels away from what most writers are able to do.

Have you ever read the Boron Letters?

Years ago.

Okay, so this is a must-read. Yeah.

Copywriting.

Copywriting. I'm surprised you don't have them printed out of your pocket. They're that good. So the Boron Letters are this amazing thing by this renowned copywriter, Gary Halpert, I think, writing to his son and he's in jail. So the writer is now in jail and he's writing to his son, Bond, I think is his name. And so it's a series of 23 letters and They're hard to find too. It's really annoying. There's like one blog. So I hosted them on my blog now because I was like, this is crazy that it's so valuable and so hard to find. So anyways, he posted, he wrote these letters and he just wrote it again to one person. He's like, "I'm writing to my son." But obviously these were kind of like general principles of life and copywriting and marketing and he's teaching, he's trying to teach him everything he knows. But because of the way he wrote it with such a casual, warm relationship, he's not even just writing to one person, he's writing to his son. And because he's writing to his son, he's like, "And this, dear Bond, is where things get interesting." Where he's like, "You're probably wondering, Dad, why do you say this? We're going to get to that. But first, a little detour." And he just started writing so differently that I was like, "Ooh, I like this style. This is just like, has a swag to it that is just appealing to me." So I started stealing that basically. I was like, "Oh, I'm going to write like that. I'm going to write like I'm writing to one person." And that one person is my little young grasshopper. It's like, "This is my kid or it's my little cousin or it's me when I was younger. I know what you're thinking, blah, blah, blah. But mamma mia, you're wrong." And I'll just try to just make it fun and interesting as if it's written to one person that has a warm relationship Somebody that's kind of like, I want to be the sensei and that's how I write in those where it's like a master-teacher relationship. And other times it's the opposite. It's I'm the beginner and I know that other people are more knowledgeable about this and I'll be like, and I just will be open about that. I'll be like, so being the idiot that I am, I decided I was going to do these 3 things. I knew there was probably a better way to do this. You probably know 4 better ways yourself. You're probably staring at this right now Wondering, how could this guy be so dumb? Well, the answer is blah, blah, blah. And I'll try to say it like that because I'm just trying to make it where I'm trying to imagine what is the reader thinking at this? What would I think if I was them? And then I try to address that in the moment because it's very frustrating to me when, imagine if you ask somebody this question, you're like, how did you do it? And they're like, I just did this. And you're listening to a podcast and then that podcast host doesn't ask them like, Wait, wait, wait, what do you mean it just worked? Or what do you mean he gave you a million dollars? Why did he give you a million dollars? It's the most frustrating experience in the world when that doesn't get addressed. So in writing, I try to do that too. I try to just call out the thing I would be wondering about or I would be skeptical of or I would be excited about in that moment. I just try to include it in the dialogue.

One of the things that we talk about all the time in Write of Passage, one of my core principles is imitate and then innovate. And it's exactly what you did there. So I asked you a question and you said, "Okay, have you ever heard of this thing? Well, Gary Halbert does this very well." And then what you did was you deconstructed exactly how he does it. And then you said you found a general principle of his work. So you said, "He's not just writing for one person, he's writing to his son. And then the implications of that are this, this, this, and this." And the The roadmap that you took to give me that answer, I think is very revealing of how you think about writing, where you start somewhere, you deconstruct, and then you say, "How does that show up in my own world?" And then you try to build up a generalizable principle that then you can use for your toolkit whenever you're typing yourself.

Yes, that's exactly right. I think that is a great thing for anybody to try to do. If you want to get better at something, that's the way.

Yeah.

By the way, I randomly just thought of the best example of framing from way earlier while you were talking, which is kind of how the brain works. The brain relaxes and then something comes to it. Have you seen the Dave Chappelle thing called Unforgiven? Have you seen this on YouTube? Nope. All right. So do you remember a while back Dave Chappelle was in a feud with, I think it was Netflix, and he was like, the Chappelle Show was put on Netflix and he wasn't getting any royalties. So it's his name, it's his face, it's all his life's work. And not only was he not getting paid for it, he had had a big falling out with the creators of The Chappelle Show where he ended up quitting. The story at the time was they offered him $50 million. He said no, and he went to Africa and became a crackhead instead. That was the rumors. Dave Chappelle's a crackhead now and he's in Africa. And later he was like, "No, I just said no. Why did I have to be a crackhead in Africa? I went home." What are you talking about? So anyways, here's the objective. His objective was he wanted people to boycott the show. How do you get people to boycott the show? If you want to drive people to take action, you got to be smart with how you're going to persuade them through the written word, or in his case, he wrote it first and then he performed it on stage. And what he did was instead of talking about Netflix or talking about his show or saying, "Go boycott my show, please," He reframed the problem in a totally different way that I thought was brilliant. He just changed the frame completely. So he tells a story, he goes, "I remember I was 14 years old. First time I ever did comedy, I was 14 years old. I go to this comedy club and I tell this joke." And he's like, "I'm going to admit it. I was good right away. Comedy came naturally to me. I'm not one of those people who's like, it took me a decade." He's like, "Honestly, I was good and I was 14, 15, 15 years old, I think." And he's like, "I was underage, but I was good." And he's like, "I came backstage and there's a guy who's been doing this for 20 years and they were like, 'Hey kid, you did pretty good, man. That was good.'" And he was like, "One guy came in and was like, 'Hey man, I like that joke. I have this big audition coming up for this TV show or something for this other thing. You mind if I use that joke?'" And he's like, "Even as a kid, I'm 15, this guy's bigger, older. I looked up to this guy." He's like, I didn't want to do it because I was like, "My joke's all I got. I got no money. All I have as a comedian is my jokes." He's like, "But this guy was kind of asking. I felt uncomfortable. He said he just needed it for this audition. So I was like, 'All right, man, sure, you can use the joke for the audition.'" Guy's like, "All right, cool." He's like, "Several months later, I go to the club. I'm about to perform. That guy's before me. He tells my joke and the joke kills." He's like, "I was pissed." And he's like, "I didn't know what to do." He's like, "Afterwards I went up to the guy." Again, I'm a 15-year-old kid. He basically is framing it as, "I'm this powerless kid and this guy's taking advantage of me." And he goes, "I told him, I was like, 'Hey man, you said you were just going to use it for that thing. I want my joke back.'" And I think maybe he had given him $100 or something like that. And the guy kind of roughed him up. He grabbed him and he was like, I was just asking to be nice. I could just take it. And he's like, I was scared. I didn't know what to do. I let that guy take my joke. Okay, so that's the story. He's like, I'm going to tell you another story. He tells a story about later on he's in New York and he's like, I got a date with this Jamaican girl. He's like, fine girl, banging on you. I couldn't wait to go on this date, but I didn't have any money. I'm still a struggling comedian, but now I'm older. I'm 22, 24 or something like that. He's like, And I was walking around New York and I see these guys doing that 3-card monte where they like that game. And I'm watching it and a guy puts down $100, moves the thing around. I know it's over here. He guesses the wrong one. He loses. He shows it's over there. Next guy goes, same thing, puts down $20. I know it's over there. He picks over here. He loses. I'm like, "God, I could do this." So I step up, I put all $100 down. I say, "I'm going to double this. I'll take my girl out tonight." I know the ball's over here. I say, "That one." Ball's over there. He's like, "What the hell just happened?" He's like, "I was pissed. I lost $100. I have this date tonight." He's like, "So I stuck around and I watched and I realized those tourists, they didn't leave. They were still here and they did it again." He's like, "Oh, they hustled me. Those guys are in on it together. They pretended not to know where it was. And I was the mark who came up and said, 'Oh, I figured this out.' They got me in there." Somebody else came up and they were about to make the same mistake. And I told them, "Don't do it. They're all in on it." And the guy goes, "Oh, okay." And he leaves. He's like, the guy wraps him up again. And he goes, "Hey, man." He goes, "I don't care what you think." He's like, "Never get between a man and his next meal." He's like, "You just took money out of my pocket. This is my job. This is my livelihood. And taking away a man's livelihood is the equivalent of killing him." He tells him that. Okay, cool. Then he finally gets to the Netflix story and he basically weaves together those parts from before. He's like, "They didn't ask me if they could put it on Netflix. They didn't ask me to basically, they didn't ask for anything. They just took my name, took my face, took all my content. They just took it." He's like, "And then the second thing was the people would say, 'Well, you signed the contract, Dave.'" He's like, "I was a 21-year-old kid. I hired lawyers to read these contracts." They told me everything. I said, "Hey, you can use this forever in perpetuity in all parts of the universe?" And they're like, "It's standard, Dave. Don't worry about it. This is standard Hollywood stuff. Don't worry about it." So he's like, "So I signed it. Later on, I realized those guys all go out to dinner every week. The lawyers on my side, their side, they're all in on it. This is just like the three-card monte. That's how Hollywood is. I was the mark. So yeah, I signed it, but whatever." And he got the whole audience on his side. By making this argument, by using these two stories, I think it is the most brilliant example of PR or a written story that I have ever seen. By the end of that thing, you're like, "I will delete Netflix if they don't take the show off." And it's exactly what happened. People saw that video on YouTube. It went super viral because it was so well done. People boycotted Netflix. They took it off. And Netflix said, "We don't have to do this, Dave, but we voluntarily will do this." "We were also moved by your story. We're not going to put your fellowship up there unless you say we can do it. Even though contractually we have the rights to do whatever we want, we're going to honor the non-contract here." I thought that was the power of reframing, not like, "Oh, I'm getting screwed. I want money," to a more universal, "You're getting picked on by the man. You're getting screwed by people who are all in on it." And I thought that was absolutely brilliant.

That is, yes.

You should go watch this thing. It's amazing. Yeah.

I want to talk about distribution. So one of the things that we're working on at Write of Passage is what I want to figure out is I want to figure out how to take anybody, people who don't write all the time, don't really have an audience, they've just published something really good. Say that you are an absolute expert in the distribution of San Pellegrino waters from the little town in Italy, how they where they package it, what's the story of the label, all that sort of stuff. And you are like, this is how the sparkling water boom came. And I'm going to tell a story of how it begins in a little town in Italy with San Pellegrino water. You have this expert, he, she never written online. They write something, it's awesome, and I want to help them distribute it. They come to me, they say, what do I do? How should I talk them through that?

I think distribution is built over time. I don't think that's something you can do from day one. It's kind of back to that 100 videos thing from earlier. If you're going to write online, there is sort of a beachhead moment you have to create. You have to create a trusted audience over time and you have to know that the distribution is earned, which is why distribution is so valuable because it's hard to replicate. So for example, my buddy Jason used to say this thing. He goes, "Oh, I have the 1, 2, 3 rule of interestingness." What does that mean? He goes, "Tell me one thing that's interesting. You tell me one thing that's interesting about San Pellegrino, I'll say, 'That's interesting.' Tell me two things that's interesting. I'll be like, 'Those were interesting. That's two interesting things.' You tell me three interesting things, I'll say, 'You're interesting.'" And this is just a general philosophy I think you should have with writing is you don't deserve that trusted follow or relationship until you've, and 3 is a small number, really on the internet it might be like 20 things. You might have to tell somebody 20 interesting things before they're like, "This guy's interesting. I can't wait to get his next one." And you just have to build that up. You have to consistently be telling somebody something interesting multiple times for you to earn that channel between them where they're now going to be receiving your content or they'll be willing to vouch for you and spread you to another person, not just on the merits of the one thing, but because you are interesting and you consistently share interesting things. And then when groups of people think you're interesting, it's even more powerful, right? Because then another person comes in and just says, "Oh, everybody thinks this guy's interesting. Cool, I'll follow." Which is why the more Twitter followers you get, the more you're going to get. And it's actually not a bug. People get mad about that, like the rich get richer. It's not a bad thing. It's actually a useful mental shortcut. The people who have earned a following are probably likely worth following with some exceptions, but it is a useful hack versus I have to individually vet every account to figure out who I want to follow. That's the slow way. I'm going to follow the people that other people follow. It sounds just like, oh, you're just being a— it's part of the herd mentality or groupthink or whatever, but there's a reason it exists. There's an evolutionary advantage to doing it too, which is it saves you a lot of time of having to individually vet every person. So I would say to that person who wants that distribution, it's cool. That's one interesting thing. Let's do 20 and start with your friends, start with your friends and family, start with some group chats, start with maybe you have to push the wheel a little bit, send it to some people who might find that interesting that you know of with a personalized message of why you think they might find that interesting. Yeah, you're going to have to do some of that hustle at the beginning to get the word out. But you should also not have some expectations that just because you said one interesting thing, it deserves to be spread everywhere. That's not really how it works.

On Twitter itself, you have built a huge audience without writing that many things, and you've had a few things that have just absolutely cranked. What do you think that you understand about that platform and communicating there that other people are missing?

Well, I'll say this. I think what I did worked on Twitter. So basically I remember I was at 20,000 followers, which is a lot in general, but I was like, I'm going to get to 100. Now I'm at 400. So I'm like, oh, I way overshot that goal. 400,000 followers. But most, I'd say the generic best practice is be consistent and define what your niche is and then talk about stuff in that niche. I don't really do that. So I would say I defy that, but I don't think that's what helped. I think I almost won in spite of doing that. I think if I had been more consistent and I had defined my niche, I would be at 1 million followers instead of 400,000. So let me put that out there. Even though I didn't follow the best practices, I don't think the right takeaway is those are the wrong. I think the right takeaway is it would've been even bigger had I followed those. The one thing I did get right was I knew when everybody's attention was on a certain subject, I had an interesting take. It's not my writing so much as it is the thinking. I'm sure, I haven't listened to all your interviews, but I am sure one of the most common themes is that great writing is just great thinking. Clear writing is just clear thinking. Writing helps you think better and better thinking helps you write better. They're so tightly intertwined that the unhelpful but true advice is, I think I had an interesting thought to say and I said it at the right time when people were paying attention to that subject. And then thirdly, I wrote it in an interesting way that helped the spread of it. I wrote some thread about the metaverse that went super viral and I don't think it's because of how I wrote it. I think it's because the thought in it was genuinely a good thought. I remember at the time Facebook had just rebranded to Meta and Zuck went on the Lex Fridman podcast and was like, "Yeah, I read this really interesting thing on Twitter, blah, blah, blah." It's like, He wasn't saying it because my prose was great or my grammar was great or my hook was great. He read it because he thought the core idea, underlying idea was unique and interesting. And I think that's more what to strive for is you're building up these two skill sets, having unique and interesting things to say, being good at packaging ideas. Two distinct skill sets. You can't do only one and not the other or it'll reveal itself to be pretty shallow. If you just have interesting things to say and crappy packaging, you don't get very far. If you have great packaging, but mundane things to say, people get very fatigued of it. It doesn't really work.

One of the ways that I like to judge a writer is as a measure when I read their stuff is how good is this person at building a connection with their readers? So some writers, let's take ChatGPT. ChatGPT is like a zero, right? It can be super informative. You learn a lot, but you're not actually building any sort of emotional connection. Same thing with Wikipedia, right? And then there's other people like you. I think this is something that you're very intentional about. And I think that for the average word that you have, there is like a real connection that is built. And I think that you're really focused on that because of your goals as a creator. And how do you go about doing that writing so that it's not going to be just this one and done, but so there's actually going to be like a glue of like, "Sean, I like this guy, want to consume his stuff." And actually I want to consume his stuff every single day.

When you say connection, what do you mean by that? You mean trust? Do you mean likability? What do you mean?

I think what I mean is an indispensability from that creator.

So I did the lamest thing ever once. I hired a consultant who was an expert at personal branding. I paid this guy 5 grand.

That almost feels like you're not even being serious.

It's such a cliché. I framed it as the lamest thing ever. I'm aware how lame it was. And it's not like I was like, "Oh, I want to change my image or whatever." But I was like, "Well, truth be told, if I am a creator, that means I am kind of an individual brand." Right. Yeah. Of course. Okay, so what? And this person worked with all these people, so I was like, "All right, let's do this." It goes back to the theme of what is something that is super important that people— What's something that's valuable that other people— either overlook or actually would be embarrassed to do. Totally. And your boy's not embarrassed. So I'll do it. So I hire this guy and I sit down and we talk and I'm like, okay, I learned a bunch of things from him. One of the things he taught me was he goes, people will follow you to the ends of the earth if you are giving them a feeling that they can't get anywhere else more consistently than anybody else is going to give it to them. So what does that mean? He basically was like, think of yourself as a little Shopify store and your only SKU, you're a merchant. Got him. Your merchant, your only SKU is basically one, how somebody feels after they consume your content. So for example, I used to love TED, TED back in the TED Talks. I remember TED Talks used to be the shit.

Now they're so good.

People make fun of them or whatever. 2014, they had a new vibe. Yeah, 2012, 2014, TED Talks were the shit. Or even before that, I was in college when they were cool. So why do I like a TED Talk? Even the sound, the music of the whoosh out of a TED Talk or the intro sound, the way that it looked, it was like this training, like Pavlovian training of you're going to hear one really cool idea in 18 minutes and you're going to walk away feeling inspired, inspired about the world in some way, inspired to either go do something, inspired that the world is improving in some way, inspired to make a change, whatever. And TED is a merchant of inspiration. And so I thought about that. I was like, "Oh yeah, that's right. I listen to these comedy podcasts. Why?" Because I get this feeling that I'm hanging out with my friends, my funny friends, but they're not my friends. They're just comedians that hang out. But that's why I think comedy podcasts are so popular because they can consistently give somebody the feeling of camaraderie, bullshitting with your boys without you ever having to actually be funny, have funny friends, and go hang out. And so you're getting that without the cost. Amazing. And so anyways, and this is why we got acquired by Twitch. People watch Twitch. People watch other people play video games because you get the feeling of playing a video game without having to actually sit down and buy a system, buy the game, get good at the game, and play the game. You get the same rush watching this guy try to win just by watching. It's kind of amazing. So once I realized that, I was like, "Oh, okay, this guy's right. What I got to do is pick what feeling I want people to have, and then all I got to focus on is delivering that to them more consistently than anybody else is going to give it to them. If I do that, all my personal brand dreams will come true." So that was the big takeaway. That was the lesson I had there. So when you say it seems like you're intentional about it, That's the underlying thing that it is, is picking up front, what am I trying to deliver? What's that feeling? And then consistently be like, all right, how could I do that? What's a story I could tell? What's a framework I could give them? What's a nugget I could give them that would do that for them?

I want to talk about editing, and it seems like your thing is that you're really good at writing first drafts, and actually you don't seem like somebody who's like an 8th revision, I'm going to put this away for 6 years kind of guy with editing. You seem like you're pretty off the cuff. You're sort of like MsExcel. What does the emotion want to have? I would guess then you sit down, you write it, then you go away for a few hours, maybe go on a walk, come back, look at it, ship it off. So for you, let's bring together emotion, editing. How do you edit for the sort of emotion that you're talking about there?

Okay. First thing I learned was from Sam Parr. He, as a principal, I think he came on your show too. Which is the walk away. So you do the shitty draft, you dump it. And I kind of knew editing was important. And the mistake I used to make is I'd edit right away. That's a terrible idea. Don't do that. So you first do your research and your thinking, you do a quick brain dump, and then you got to walk away. So you read it. Well, the last thing I do, I read what I wrote and then I'm going to forget about it. So I then will go do stuff. So I will go work out, I'll go play with my kids, I'll go for a walk, and I'm not trying to think about it at all. I know I'll come back to that later, and I know it sucks today. I'm going to edit it later and make it great. I'm certain of that, but I don't consciously think about it. And then I come back to it usually, let's say 4 hours, 6 hours, 8 hours, 24 hours later, and I'll read the thing and immediately I'll be like, oh, this bad, bad, change this. Oh, why don't I talk about this instead? Or I wanted it to have this takeaway. I don't think it has that right now. All right, where would I punch that up? I wouldn't have wrote this if I didn't think it had the potential to give you that because I was very intentional upfront thinking this will do it. It's not coming through. Where? And the analogy I'll use is imagine a river's flowing. So there's a useful analogy because I think a lot of people are like, there's nothing there and I'm going to make it happen. Another story you could tell yourself is, it's a river, the water wants to flow. My ideas are excellent. People are going to love this. They want to consume this and my ideas are worth consuming, but there's some rocks in the river that are blocking the flow. What are the rocks? All I got to do, if I just simply remove those, the water will flow.

Nice.

It was a more empowering thing for me versus I got to make this good. It's bad, I got to create good. It's like, no, I assume if I got to the point of writing something, it's going to be There's something good in it. I just got to remove the suck out of it. I think Pixar uses that analogy too. They say, "All movies we make start with suck, and our only job is to just remove the suck with every draft." So they do another revision, say, "What sucks about it now? Well, it sucks that the main character's not that likable because blah, blah, blah." So then they remove that suck and they come back again. That's kind of the same mindset. So I'll just look at it after I come back, and I'll say, is this doing what I want it? Do I think this is dope? Does this do what I want it to do? And if not, what are the rocks I can remove? What's the suck I can remove from this? This part's boring. This intro doesn't really hint at what's to come. This ending is just kind of like, so yeah, that's it. That's the idea. I don't have a good ending. Okay, so then I'll just find that area and I'll just try to fix that.

Cool. How about with humor? What have you learned about writing with humor? Are you formulaic about that? Have you studied it?

That's where I'm looking now. I'm starting to pay attention. What I've learned so far, I'll tell you what I've learned so far as a white belt in the humor game is just, you don't want it to be— Humor is the sauce, it's not the entrée. So some people are writing something to be funny, like this is meant to make you laugh. Usually that's not me. Usually it's, I'm trying to get a point across, but I'm going to make you laugh along the way, which will make this more enjoyable for you to consume. So it's the sauce on the meal, but it's not the meat. It's not the protein of the thing, which is good. Depressurizes it. It's like, oh, it does apply a little bit here. That's the first part. Second part is all humor is just surprise. So every joke is a setup and a punchline, but the punchline, if you see the punchline coming, it's not very funny. So humor is surprise means I have to set it up in a way where you don't anticipate this is what I'm going to say. And the contrast of what you thought I was going to say and what I actually said is what makes you laugh. So you just have to look for those moments where there's a bit of an expect— you set up an expectation and then you subvert the expectation.

Jerry Seinfeld, article in The New York Times. Here's how he starts it. Knew this was going to come in clutch and it just came in handy. He goes, when I got my first apartment in Manhattan in the hot summer of 1976, There was no pooper scooper law and the streets were covered in dog crap. I signed the rental agreement, stepped outside, and my car had been towed. Despite this, I still thought, this is the greatest place I've ever been in my life.

You know, exactly.

Sets it up. Pooper scooper, funny word.

Yeah.

What's going on there? And I think that maybe we can go into funny words because it is interesting how certain words have a much higher propensity to be funny than other ones, right? If he had said there was no law around cleaning up your dog's excrement, that now is very— pooper scooper is jovial, funny, right?

Exactly.

And then he goes and goes, takes you into this other time period. You're thinking about poop, but then he goes, "My car had been towed," and you're like, "Oh my goodness, this sounds terrible." And then you said surprise, which is why I thought about that. He goes, "Despite this, I still thought this is the greatest place I've ever been in my life." And this is in this Ode to New York City.

Theo Vaughn is super—

That's exactly who I was thinking about.

He's super popular right now.

So good.

And he's been great. I followed him since the Real World days, basically Road Rules days. And so if you just listen to him talk, his brain just does something different. His brain is almost wired different. That was my initial story. But then I was like, I bet you could practice Theo Vaughning a little bit because what Theo does, if you've never seen him, it's not going to make any sense. But if you've seen him, This will make all the sense in the world, which is that Theo Von will basically improvise. He has no idea what he's going to say, but he improvises and he uses random language or he'll make up a story that is totally not true, but it's kind of believable and he keeps a deadpan face when he is doing it. You can kind of practice that. And so yeah, I think practicing is obviously the best way to do it.

Well, that's a big one. Let's follow this made-up language. Coming up with words, things that other people hadn't thought of. And how do you go about doing that? It's a fun little thing to play around with. One of the things that I did is I like thinking through the juxtaposition. So I wrote a piece about how I fell in love with the Bible, and I was like, it needs some little bit of humor in it because it's the Bible. It activates a part of your brain where you're like, okay, this is—

Bae.

Exactly, right?

The Bible should actually just say bae. And that should be the whole thing.

Exactly. So it activates that. I was like, I need something that's funny. So I was like, okay, what is the emotional state that somebody's in? And I was working on it. I was like, serious. You think of almost like this fancy library. And then I'm like, I would do my Bible studies at a Schlotzsky's parking lot in a strip mall in the Hill Country. And now you just get this juxtaposition. I'm not sure it was that funny, but I think that it adds so much life to the piece. And I always try to think of If I'm trying to be funny or create suspense, what is the emotional state that the reader's in for most of this piece? And then let me, just like we were saying, let's bring a little bit of Tabasco sauce of the opposite.

Yes, yes. That's exactly right. And I think an exercise you can do is, so a Theo Vaughn exercise is basically he takes a thing, so let's say it's the Bible. So it's the Bible. But what a Theo Vaughn humor kind of lane he does is he'll call the Bible something else that's kind of funny. He'll be like, "Man, that Jesus's binder." And he'll be like, "It's the Bible, but now he calls it Jesus's binder." Then he'll do another one and he'll be like, "That old Himalayan diary." And it's like, "What? What are you saying?" He just keeps coming up with different ways to say the Bible. Or he'll just be like, "That big brown behavior book." And he'll just keep going. And I've never done this before, but You could try that. So you could just take anything and be like, "I'm going to come up with 6. I'm just going to keep going." And it's so hard to do. Just now when I was doing it, I was like, "Why the hell are you trying to do this live on a podcast?" But that's how you get better. So doing that is it trains your brain in a very different way of thinking than we are used to. And that pays off because again, common traits uncommonly together is very, very valuable. You don't need to be the funniest. Nor do you need to be the smartest. If you're pretty smart and you're kind of funny, you're the best. So that's my whole strategy was basically to do that. I was like, I know I'm not funny enough to be a comedian, but I'm funnier than the average smart guy and I'm smarter than the average guy. So it's like pretty smart, kind of funny. That's a good combo.

Well, it's funny because I went to church last weekend and I was with a friend And basically after the service, she was like, "Man, that was a really good sermon." And I was like, "Well, what do you like about the pastor?" And she was like, "Hmm, he does a really good job of talking about very serious weighty things, but then layering in tons of humor." So he was talking about He was talking about, you could have said good people go to the light and they're focused on moral values and integrity and bad people move to the darkness and they run away from righteousness and stuff like that. And you're like, okay, that's not right. And he goes, at any moment you can either be a cockroach or a moth.

Right.

And I grew up in South Carolina and you go into the pantry sometimes and there's some cockroaches on the ground. And like, you want to step on those things, but those things fly and they go all over the place and like they'll start eating your Ritz crackers. I swear those cockroaches are so big they can practically pick up the babies and they'll take them to cockroach land or wherever. Right? And cockroaches, they run away from the light.

Right.

And then you have your moths and the moths, they go to the light. And then he like weaves these cockroaches and the moths throughout the entire sermon. So you're getting this like chuckle But then through the chuckle, it's creating this avenue for extreme depth. And somehow it's in the juxtaposition of those two things that the sermon ends up really hitting. And the humor lowers your defenses on needing to be a super perfect person and all that. And it's like, okay, we can have some fun here. But then the fun actually allows us to then get to the depth.

And that's framing. He framed it differently. Same principle, framed differently. All of a sudden more accessible. More fun, more entertaining, more memorable. And memorability is massively underrated. What's the point of having the good ideas if nobody remembers them? Part of your job, a responsibility, if you actually have something worth remembering, is to take the time and effort to package it in a way that is going to be catchy and memorable. My buddy Trevor, who was my roommate in college, He made his whole career doing one thing. He basically reads white papers, which are like scientific journals. They're the most boring, read the abstract, read the whole study, whatever. It's crazy. The scientists spend their whole life working on this thing and then they package it in the dullest format possible with pride because that's like a—

That's high status.

High status for them. It's so boring that only another person who's dedicated their life to this would possibly read this, which means that none of the insights get taken to the real world until somebody comes in and builds that bridge. So he built that bridge. He would go learn something, he'd read this and he'd go talk to the scientists. Somebody's been doing this for 50 years and the number of people who follow them and listen to them is 35. And then my buddy started writing a blog and newsletter and eventually YouTube and he built a 100,000-person email list about a really dry subject, which is growth mindset, which is how it applies into classrooms and stuff like that. And so the way he did it was the same type of frame. He's like, imagine two tigers. One tiger grew up in the zoo and a tiger that grows up in the zoo and he'll teach this to third graders or he'll teach it to the New York Yankees, CEOs of companies or kids basically. He does the same speech to both the folk because it's so easy to understand, so memorable. He's like, "Tiger that grows up in the zoo, has their life been easy or hard?" Pretty easy, right? "Do they fight for their own food or is it given to them?" It's given to them. Okay, cool. Jungle tiger. Jungle tiger's life, hard, right? Lots of adversity. They have to fight for their own food. They know how to survive, blah, blah, blah. If you take a jungle tiger and you put it in the zoo, what happens? They're like, It'll get bored. It's like, if you take a zoo tiger, you put it in the jungle, what happens? It's dead. It doesn't know how to survive. And he's basically like, you want to be a jungle tiger. And how do you do that? Well, you have to get out of your comfort zone, the zoo, where everything is easy and handed to you. And so when you reach those moments where you're out of your comfort zone, say to yourself, this is my jungle tiger moment. I got to jungle tiger this right now because I have to put myself out of my comfort zone to do this. He gave them a language to remember a whole set of principles that were all previously packaged in very boring scientific terms.

One of the things that I'm noticing from you, I always think, okay, I'm doing these interviews, how is my writing process going to change? And one of the biggest things I've picked up is I don't need to learn from writers at all. What I'm going to do is I'm going to go study comedians and I'm going to be more deliberate about finding communicators who I really like, and then trying to say, what are they doing? And then bring that into my writing. And then also I think that you really see a fluidity between mediums, that talking, writing, humor, storytelling, these things can all sort of play together. And they're sort of like paint colors where, yeah, you can have the white paint, the black paint, the blue paint, the green paint, but then you can also have, you can begin to mix them together and then you can get all these different colors. And that maybe we shouldn't be thinking about writing as all these separate lanes. Actually, for a lot of the different skills that you want to learn to make yourself a better writer, don't even study writers. The best people for that might be in a totally far-off field.

Yeah, yeah. You nailed it. Good job. You synthesized it very, very well. I do think it's a good strategy to basically pick and choose from adjacent fields because you're going to do something different than you will only looking in your own lane, it's why everything becomes the same because we all look at the same things, we all study the same things. And so I was hanging out with MrBeast and he said the same thing. I was like, "What YouTube channels do you like?" He's like, "I don't really watch YouTube that much anymore." I'm like, "You're the number one YouTuber in the world. You live, eat, and breathe YouTube." He's like, "Yeah, my channel." But then I was like, "So where do you learn from?" He's like, "Well, right now we think that one thing we're weak at is character development. So we study TV shows and movies that are good at character development." or whatever. And then he's trying to steal from other areas than— He's like, "Everybody else, if you're just on YouTube looking at other YouTubers, you'll just become lost in a sea of sameness." And I think that's a useful tip for people to take on.

I want to end here. You built a newsletter called Milk Road and you had to train another writer to write in your voice. And you believe that learning to write is actually teachable. So when you're teaching other people to write, what were some of the things that you focused on?

Yeah, so the teaching was important because I didn't want that. We had to send the email out every morning at 6:00 AM. I was like, "I'm not doing that. I'm not good with consistency anyways. I don't wake up that early. I know that no matter how fun this is, that I will hate doing by day 30." So from day 1, I was like, "I'm not going to write this, but it's going to be in my voice and style." How do you do that? Hired a guy who's never written before and I sat him down and I was like, first my business partner, I was like, you write this. And I was the editor. I was his editor for 30 days. And I said, cool, now you're the editor. Now you got to hire a writer. We hired a guy who'd never written before in any professional capacity or even blogged. I don't think he had a blog either, but I taught him. And basically what we did was we took off, one thing that helped is the newsletter was a consistent format. So it wasn't like 10 different formats. It was one format. And I broke down why we write it the way we write it line by line. Our opening line at Milk Road was always like, "Good morning, this is the Milk Road." And we would say what we do and then we would say in a funny way, and then we would tag it with a joke. So we would say, "We are the number one source for figure out what happened in crypto yesterday. Think of us like Think of us like a toaster strudel, a fresh, tasty treat for you in the mornings. And then parentheses, we tag the joke again and we would just be like, what the hell happened to toaster strudels anyways? Kids these days, they're missing out. And it's like we would always tag the joke and we'd be like, we are GM, we're the milk road. We give you exactly everything you need to know about crypto in the morning and nothing that you don't need to know. And then we would tag it, but I'd say something like, "Reading this newsletter is the second best feeling in the world. The first best, of course, is when you're in a car, you roll down the window and you start doing that cool dolphin thing with your hand." Some relatable, funny thing that's just put you in a good mood. And we were like, "Can we get you to smile and can we get you to be like, 'I love these guys'? Can we give you a reason to open this that's not based on the Bitcoin price. It was another way of thinking about it. And so I started training. I was like, the first line, this is what we do, here's why we're doing it, and here's 10 examples of doing it good. And then he was like, cool, got it. I can pattern match to that. The other thing that we did was he was doing the school thing where he thought he had to be a different guy. Maybe I need to be a really sophisticated, do sophisticated analysis, or I need to do People think when they write, they need to do something outside of themselves. The whole point of writing is to take you and just push it out. And so don't try to create this fake thing that you think other people might want. Just take you and push it out. And so for example, he would talk about subjects and the writing was fine, but the subject was boring. So I was like, "Dude, why'd you pick this?" He's like, "I don't know. I felt like it was in the news. People needed to know about it." I was like, "Did you care about this?" "No, not really." And I was like, "Would you have ever texted me or Slack messaged me or sent me a voice note being like, Dude, did you hear about this? This thing's awesome. Or this is crazy. Did you hear about this? This is really interesting. He's like, no, I would never say that. I'm like, cool, then why are we telling 200,000 people about this if you wouldn't tell me? And so what I made him do, I was like, every morning I want you to send a voice note, send a voice memo and just tell me the news before you write anything. Just be like, oh yeah, everybody on Twitter's freaking out because they're worried about this thing that happened. Or Price is up today because there's rumors about this right now. And what that means is that if that happened, then this would happen. So he would just say it to me and it was such a good filter because he could stop himself if he was going to tell me something that was boring. He would catch himself like, I would never say this to somebody. It's boring to me and it'll be boring to you. So it filtered out the subject beautifully. So those are the two big things was showing him what we do in giving him a sample and then saying, Here's what good looks like. Here's 10 more examples of good. And then secondly, installing that one step of don't do that imposter thing where you start talking about shit that you're not even that interested in because guess what? Nobody else is interested in it. And the filter for that was send me a voice memo. If it's not interesting in the voice memo, it's definitely not going to be interesting in long text.

Why do you think that dolphin thing is so funny? It is hilarious.

It's relatable. And It's not even that funny. It's just funny that we put, again, it's unexpected. Why are you writing this? Everybody says we're the best. We said we're the second best thing in the world. So immediately, what's first best? First best. And then I can't say a serious thing. I have to say an unserious thing. So I'm like, the first best thing is this feeling because we all know this feeling is great. You know that feeling. It's an amazing feeling. And so we just knew, okay, things like that, are surprising, likable, funny. You can do them in one line, so it's not like you have to set up a long story or joke. It was very useful. It was very efficient as a mechanism there.

Sweet. That was good fun. Thanks, man.

Yeah, absolutely. Thanks for having me.