The Exchanges

Q And then when you talk about sort of like rallying your, the people like you and making, is that spreading your surface area out? So it's like, you're not just attacking me, you're attacking everybody who's like me.

A Yeah, so I, I sometimes refer to an equation in physics, which is P equals F over A. The pressure equals the force divided by the surface area, and it, it's very intuitive, right? Like, the same amount of force, if you spread it over a wide surface area, doesn't exert a lot of pressure. So think of, like, a big sheet of paper that's pushing down, versus if the surface area contracts, then the same amount of force creates a lot of pressure, so, like, a needle can puncture through. So, like, uh, A sheet of paper, really hard to puncture through. Needle can puncture through. Or it's the same when you're trying to rip fabric. If you're just tearing fabric, it's really hard. But if there's a tiny nick already, the whole thing just comes open. And so the way to think about this is if you're trying to relieve pressure, you don't get to change how much force is coming at you, but you can change the surface area. You can spread it out over more surface area. You're not just attacking me. You're attacking all of us. You're not just attacking, let's say, Sub stack or a sub stacker for a specific post. You're attacking all independent writers who are trying to assert their freedom of expression. That's a way to diffuse the pressure on you and rally people to you in a very powerful way. And then if you're ever on offense, not that you want to be the antagonist and go after someone and attac…

AI assessment note: “you don't get to change how much force is coming at you, but you can change the surface area.”

Q Yeah, definitely. One of the things you said that got my attention in a previous interview was that you have second strike capability. What does that mean? Unpack that for me.

A It's, it, it goes, it relates to, to deterrence. So you might not want to be the aggressor. You might not want to be out instigating and starting fights, but you want to establish that you're not a soft target. And being a hard target can look a bunch of different ways. So at Shopify, one of the things that we're really proud of, I'm on the board, and we have this wonderful general counsel, Jess. One of the things that we've been really proud of at the company is that Shopify has been in the past a victim of patent trolls that just go over, they just go out to companies and attack them, and then they settle, and then they get money that way, and Jess and her very strong team have decided that they're going to fight it every single time, and in the short term, super expensive, huge Huge pain. Again, you, you take the pain up front so that you don't have to live with chronic pain for the rest of your life. You get the surgery now so that you don't have to deal with it, and now Shopify gets no patent rules. Zero. Zero. And so just establishing yourself as a hard target, or we talked before about Palmer, and if you cross him in any meaningful way, he will guaranteed head back. He will not let it stand as a matter of principle. Doesn't matter legal advice. Doesn't matter PR. But like, He won't let it stand. You need to have something about you that's a little bit spiky. You need to …

AI assessment note: “It relates to deterrence. So you might not want to be the aggressor”

Q How do we go about determining what that narrative is?

A The wrong way is, here's what I want to say. Here it is. Because the thing that you, you care about might not be what anybody else is caring about. I think the right way is to take two things. One is, here's what I care about. So like, think of it as a circle of information. Here's what I care about and what I want to say. Then there's another circle of, here's what the person I'm speaking to cares about and what they're thinking about. And it's probably a little bit different from what's on my mind. If it were identical, then what's the point of saying anything? But there's probably going to be some overlap. And so what people tend to say is the circle of things that are on their mind, and then just put it out there and hope that somebody latches onto it. The real story to tell is what's in the center of that Venn diagram. So don't tell the story that's in your circle, because it It's hard to get other people to care. Don't tell the story that's in the other person's circle because you don't get anything out of it. It's not strategic. Tell the story that's in the Venn diagram, and then once you meet them in the Venn diagram, you can kind of walk them into the rest of your circle. You give them a gateway drug.

AI assessment note: “The real story to tell is what's in the center of that Venn diagram.”

Q So should that hook be like emotion? Should it be tension? Should it be stakes? Like you get invested in reading this? Should it be like, what's in it for me? How do you think about that?

A It could be any of the above. The most Common ones that I've just observed online are humor, curiosity, or some strong emotion. It can be a wow emotion. It can be a WTF emotion, or it could be, here's a topic that I'm already thinking about, and this is going to give me some new angle on the topic. Depends on who you're talking to. Like, if you're talking to brain rot teens, it might be a little bit different from if you're talking to AI researchers, or if you're talking to academics, you can use slightly different things, but, but it's humor, curiosity, uh, strong emotion, outrage, shock, surprise, or they're about to learn something about a topic that they're already following.

AI assessment note: “It could be any of the above. The most Common ones that I've just observed”

Q You mentioned that we can engineer trust. How do we do that?

A One is repeated exposure. So in order to trust somebody, first you have to have a sense of who they are. Like you won't, you wouldn't trust a stranger. You wouldn't trust a mystery man. So one is you have to know who, who are they? They have to show up enough for you get a, for you to get a sense of you actually know them and they're not a total stranger to you. It's hard to trust a stranger. But it's easy to trust even a stranger that you have a parasocial relationship with because they're not a stranger. There are people that you've never met in your life who would trust you because to them you're not a stranger. So first is just become not a stranger. Second is establish a set of shared values. I wouldn't necessarily trust your opinion on a restaurant unless I knew that you and I like the same type of food. So if you are like a vegan that hates spicy food and whatever, I, I probably wouldn't take your restaurant recommendation, um, even if I like you as a person.

AI assessment note: “One is repeated exposure. So in order to trust somebody... Second is establish”

Q I want to come back to politics just for 1:02. I don't want to get into left or right. I want to ask, do you think that Donald Trump is an effective communicator? What makes him effective at communicating? Uh-huh.

A One is he speaks at like a third grade vocabulary level. He doesn't use words that nobody can understand. Maybe cofefe was the one time. Cofefe aside, he uses words where everybody knows what the words mean. Strong, great, bad, good. Everybody knows what these mean. I could read my seven-year-old a Trump speech, and they could kind of grasp what's going on. Or I could read to my immigrant parents, and they would know what's going on. Or me, right? So, so one is just, he uses normal Common words that have a very clear meaning, and it's so basic, but so many people just don't do it. The other is he has very strong deterrence. He behaves very predictably, and so, you know, people will say he's erratic, he does, but he's kind of predictably erratic, like his behavior patterns are actually quite predictable, and so if someone is a super Trump or a Trump fan, they know what they're a fan of. It's not like it's unclear, you know, he's this manufactured thing that sways in the wind, and He's like the John Kerry kite surfing video. He's this way one day, that way another day. We don't know. Like, it's very clear, and everybody who hates him already hates him. Some costs. It's baked in, but it doesn't continue to hurt him. Like, people who hate him aren't going to be more damaging to him tomorrow than they were yesterday, and the people who love him, like, already are on board with this.…

AI assessment note: “One is he speaks at like a third grade vocabulary level.”

Q Do you think of that as sort of like an API into people, or is it positioning something so that people can be receptive to it? And then at that point, once you've got a hook, you can pull them along to sort of the message you actually wanted to say.

A Yeah, it's the API into their mind, um, or it's the gateway drug. Whatever it is, it's, it's not just the thing you want to say. It's the hook. You start with the hook, and then once the hook is in, then you can do the reeling. But some people are like, here's the fish sandwich I'm going to make for dinner before they think about what goes on the hook, and is any fish going to bite the hook? So the hook is probably the most overlooked part. I would say in order of how much it matters, it's the hook. How you tell your story, and then where you tell it. Most people get this reversed, where they spend an inordinate amount of time thinking about where can I go talk? What podcast can I go on? How do I pitch Shane Parrish? How do I get on TV? Do I start a pod? Do I do a blog? And they think about the form factor in the medium, and they don't think enough about how can I become so interesting that my distribution method is people telling other people because they can't get it out of their heads, and they have to. It's, it's, It's in there, and it's tickling their brain, and they have to share it with their families, and they have to go have a conversation about it. That is the most powerful, most high-lovers thing, and nobody thinks about it.

AI assessment note: “Yeah, it's the API into their mind, um, or it's the gateway drug.”

Q don't know what it's like inside companies now, but for a long time, uh, in the government and, and in large corporations that I was working with, the answer was always like more comms, but nobody was asking like, what's better comms? You know, it's not like we need to communicate more. It, you know, we need to be more effective at our communication. How do you think about that?

A This is the, um, this is sort of Goodwin's law where once the measure becomes the goal, it ceases to be a good measure, and what we've done is we've taken a group of people and said your job is communications, and your metric is communicating a lot, presumably. If you picture a scenario where people have a job and their job is just to communicate, versus a scenario where the goal is to help people understand something important, this plays out completely differently. In the first scenario, the people whose job is communicating are just generating activity to try to show that they should hold on to their jobs and be able to get jobs in the future. Whereas, In the second scenario, if the goal is to help people understand something important so that we can effect a change in the world together, that's more the paradigm that I think is the reality today. It's just not evenly distributed, but the, the top leaders, like the Toby Looker, Brian Armstrong types, they already get it, and that is the most effective person to speak is the person who's leading the enterprise. If you were building a cult, and I would say that most successful startups are like cults in many ways, if you were building a cult and You would never be like, let's not let, have the cult leader speak. He, he might go off the reservation, and he's kind of quirky and eccentric, a little bit weird. Let's just have some…

AI assessment note: “once the measure becomes the goal, it ceases to be a good measure”

Q In the interest of better political discourse around the world, how do you argue with that if you're the opposition? When your opponent is telling a story, but factually, it has no basis in reality, and you're coming out arguing with facts, which isn't going to win. How do you, how do you counter that?

A You have to fight story with story. There's no, like, the most powerful statistic is probably not as powerful as the median story. Like, the most powerful statistic is not as powerful probably as the average story. If someone is fighting you with stories, you have to fight with stories. Out of the statistics will be better stories. Under the statistics are more powerful stories. So the facts are on your side, better stories can be found. And if your opponent is actually lying in their skullduggery, maybe there's a story about that. Like in the, in the tech world, we're seeing a very interesting story play out between Rippling and Deal, which are these two payroll processors, and Deal planting a spy, and the spy, like, running into the bathroom, and then trying to flush a phone. I mean, it's very vivid, and so All this back and forth about you spied on us, and we spied on you, and you told people this, and our revenue is this, but you claim you're like, all of that fades into the noise, and people are just picturing like the spy hiding into the bath, in the bathroom, trying to flash a phone. So if someone is actually lying and attacking you, maybe there's a story to be told about that.

AI assessment note: “You have to fight story with story.”

Q How do they, how do you think about that?

A I think God smiles on underdogs, and I think that if you are blessed to be in an underdog position, you should try to take advantage of it. It's not going to feel like a blessing in the moment. It'll feel really horrible, but there is something to being so clearly punched down on That gives you more power and liberty in that moment, where people will naturally sympathize with the underdog. People are naturally very skeptical of big mainstream corporate media right now. People are very skeptical of bullies. And so if you're in the receiving position of that, I think you can actually use that. Because if you, if you realize that you're not trying to win over every single person in the world, but that there's a certain set of people you need to win over who are aligned with you, Then actually all you need to do is help them understand that you and they are on the same page, and an attack on you is an attack on them, and use that to rally them to you. So I think that a hit piece is not the worst thing that can happen. There's a, there's a kind of horseshoe where a great piece, fine. A hit piece, fine, kind of fine. You can use it. Doesn't feel good, but you can use it. What you don't want is the uncanny valley where it's not a hit piece, but it has information about you that, while it doesn't sound aggressive or hostile, makes you look horrible. Like, that's the worst way of lookin…

AI assessment note: “So I think that a hit piece is not the worst thing that can happen.”

Q Going back to physics for a second, how important is velocity when it comes to communication?

A Yeah, so I talk about velocity a lot because velocity is a vector. It has a magnitude and a direction. People talk a lot about magnitude. They don't talk about direction. So they talk, uh, this is what you were saying earlier with, like, people just say a lot of words, but it doesn't mean anything, and so sometimes it feels like the metric is just quantity of yapping, and we're gonna go on all these podcasts, and we're gonna deliver blog posts. Like, I've seen inside a lot of comms teams or agencies Where their metrics and their KPIs for the quarter are two op-eds, three podcasts, four town halls, and, and it's all about quantity without talking about where are we trying to move the needle to. So it's kind of like, you know, the, you know, the Claude logo that's, you know, like the Starburst and in all these different directions. You don't want your comms to look like that, where you're just, like, doing things in a bunch of different directions. You actually want your comms to look kind of like a line that builds towards a destination, and if you don't have the direction in mind, then it's just a bunch of frantic activity and wasted motions, some of which cancels each other out. So again, it goes back to don't worry so much about where you're going to say it. Worry about what are you going to say. In none of these plans and strategies that lay out three town halls and four op-…

AI assessment note: “velocity is a vector. It has a magnitude and a direction.”

Q So, so walk me through if you were in that room, hypothetically, and All the lawyers are saying you, you can't go out there and just talk yourself. You can't open your surface area. You can't, you know, give more. You can't admit guilt. You can't, uh, do any of these things. How would you, what would be your advice in that situation?

A Here's a, here is a big difference between the CEO and anybody else. Most other people, their job is to optimize for one specific thing. So lawyers, they're doing their job, their job is to minimize legal risk, and to minimize the surface area of legal liability approaching zero. The CEO's job, and this is like a Hegelian political philosophy point of view of weighing and considering different factions and different interests. The CEO's job uniquely is to consider different interests and weigh them against each other to reach the net optimal outcome for the company. When this goes wrong, what it looks like is everybody gets scared of the lawyers and And the CEO follows exactly what the lawyers say and dismisses every other interest. They are not doing their job as the CEO, which is to weigh the interest against each other and find the net best outcome. They're folding to the lawyers and they're making the lawyers supreme over everybody else. And I think that is probably what happened. It's what happens a lot. The problem in the real world when this happens is Is by entirely considering legal risk, you're not considering trust, reputational risk, and all these other things. Trust, reputational risk, these are things that matter inherently. Just, I don't even have to explain why they matter. Like, of course they matter. But they also come at a cost if they're lost. So if you were…

AI assessment note: “The CEO's job uniquely is to consider different interests and weigh them against each other”

Q Do you think, uh, again, not into politics, but do you think Carolyn Lovett, who's the White House press secretary, I think, do you think she's effective at communicating?

A I think she is. Um, with her, a lot of it is body language. Again, you know, separate this from, we're separating this from the substance of, do you agree with the policy? It's just like, on the pure, like the form factor and the aesthetics. Nails it. She does a wonderful job. She's really young. You know, she comes off as older than she is. And then part of that is, um, you actually kind of see her Grow into the role in the months that she's been behind the podium, which is kind of cool to see, but so much of communication is your body language and your bearing. You and I have talked about this. I'm, like, super nervous and sort of dying inside right now, but I'm trying to just, like, stay chill for you. Um, for her, just showing confidence and ease and comfort and not showing anxiety or stress or anger or resentment is a Big part of her persona. She comes off as a happy warrior. People love a happy warrior. She comes off as being confident in what she's saying, even though sometimes if you actually just parse the words in writing, sometimes you're like, I have some follow-up questions.

AI assessment note: “I think she is. Um, with her, a lot of it is body language.”

Q I love that. So that's the macro. What about the micro in terms of, like, how do I make my presentation better, my email better, my, like, what are the tips and tricks that you've learned that you wish everybody knew?

A It goes back to what are you trying to say? People worry way too much about the form factor and not enough about what they want to say. And so whether it's an email or a text or a phone call or a presentation, know the thing that you want to say. Say that. Then say why they should care, and if you can do that, you've won. Like, the vast, the vast majority of presentations or emails that are sent are more like, I need to check the box and just get this thing done so I can move on with my day to do, I guess, more of these, but there isn't a clear view of this thing that has taken up five seconds of someone's time had a goal, and did you achieve that goal or not?

AI assessment note: “know the thing that you want to say. Say that. Then say why they should care”