54. Ian Rogers - Never a Spectator

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Ian Rogers - Never a Spectator

Description

Ian Rogers (X, LinkedIn) is Chief Human Agency Officer of Ledger, the Paris-based security company whose hardware wallets secure much of the world's crypto. He now focuses on how Ledger can enable us to work with AI agents while maintaining our secrets and value.

His career has spanned music, culture, brand, and "the technolog(ies) people are going to hate next." He built and ran the Beastie Boys web presence in the 90s before working on music on the internet for over a decade: file sharing Nullsoft (Gnutella and WinAmp), early streaming at Yahoo!, direct-to-fan commerce at Topspin, Beats Music, and finally Apple, as an abbreviated list. He then joined LVMH as its first Chief Digital Officer, working with Bernard Arnault and its many Maisons to bring them into the internet era. More recently, he joined Ledger to improve its product experience, including collaborating with Tony Fadell to create Ledger's flagship form factor, Ledger Stax.

Ian's roots are skateboarding and music, which formed alongside a punk rock ideology while growing up in Indiana in the 1980s. I am glad to have captured a long conversation that covers the many flavors of Ian, and the threads that have persisted through his many lives. That includes: individuality; being a participant, not a spectator; what makes a scene; building brands; trying to help Kanye; and why new culture is always being made—it's just that you have to find the 1% that's awesome. Also: ushering forward and translating frontier technologies; being pushed by Jimmy Iovine; why security matters in the AI era; why AIs aren't people; what he wants to automate; learning to fail; advice on relationships across work, parenting, and love; and a whole lot of love for music—from his 2026 pick Twisted Teens to his desert island albums to tea with Paul McCartney.

I hope you're inspired to participate in the world and make great things.

Thanks to our friends at Ledger for hosting me.

Ian and I made a playlist with albums/songs mentioned here (Apple, Spotify).

**Dialectic is presented by **Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. You can learn more at notion.com/dialectic.

Timestamps

  • (0:00) Opening Highlights
  • (1:37) Intro to Ian & Thanks to Notion
  • (5:22) Start: Tattoos, Individuality, and Punk Rock: Spectator vs Participant
  • (16:44) What Makes a Scene?
  • (25:24) New Culture, 99% of Everything is Garbage, Finding the 1%
  • (40:09) Niche, Quality, and The Blockbuster vs. The Snowball
  • (53:35) Brand, Selling Culture Before Product, and The Age of the Individual
  • (1:08:12) Aggression, Patience, and Being Pushed
  • (1:16:52) Translating New Technologies, Empowerment, and Agency
  • (1:25:19) Interfaces, Ledger, Security, and Ideology
  • (1:39:56) Ian's New Role: Chief Human Agency Officer
  • (2:06:03) Seeing What is Real, Comfort Being Wrong, Chasing What's Fun and Cool
  • (2:13:45) Lessons from Skateboarding and Favorite Albums
  • (2:22:56) Working with Your Friends, Parenting, Love, and Remembering to Stay a Participant
  • (2:35:47) Thanks Again to Notion

Links & References

Transcript

(5:22) Start: Tattoos, Individuality, and Punk Rock: Spectator vs Participant

Ian: (5:23) And so I was like, well, if I have tattoos on my fingers, I'll never be able to hide from myself.

Jackson: (5:29) Yeah, right.

Ian: (5:30) Can't grow up and be normal.

Jackson: (5:32) But a little better than the eye drop or something.

Ian: (5:34) Yeah, exactly. I've always said I'd only get a face tattoo if Antoine Dixon and Lil Wayne were in the room. If the two of them were both in the room, I'm down. But that hasn't happened.

Jackson: (5:46) What are the—I assume they're Chinese characters or Japanese?

Ian: (5:48) Yeah, it says "to become a dragon." I always say it means I'm a jackass because I tattooed my fingers.

Jackson: (5:54) Are most of the rest of the tattoos also that old?

Ian: (5:59) No, the back I'm just trying to finish now.

Jackson: (6:01) Oh, cool.

Ian: (6:01) I won't get to it—I don't do it in the summer because you've got to keep it out of the sun. So I'll finish the back. Also, though, I have to say I'm feeling my age. When I did the back last fall, I was like, "Oh man, I might be done." But I've gotta finish it.

Jackson: (6:19) I think you've gotta keep going. Have they been pretty? It'd be fun to see the line chart of age to tattoo volume.

Ian: (6:30) Yeah, there would be a drop-off during my second marriage and a pickup after divorce; that would be otherwise constant. Nah, not really, to be honest. I don't know. Yeah, it's funny.

Jackson: (6:39) I wonder if tattoos are trending up or down.

Ian: (6:43) Well, I would say trending up, and I would say that there's a specific reason for that. I think that anyone—are we recording already? Okay, perfect. Let's go. No, it's good, because I think about this all the time. Anyone who is in the business of individuality—helping you distinguish yourself as an individual—has had an amazing 20 years. That doesn't matter if it's beauty—and I thought about this when I was at LVMH because we had Sephora and lots of beauty brands. You just realize that Instagram was crazy and they really expanded the total addressable market. It's not like you had children as beauty influencers before Instagram or TikTok. So anyone who's in the business of—again, that could be beauty, that could be tattoos. Anyone who's in the business of helping you say, "I'm a member of that tribe and not that tribe." And that's what I realized, too: a Louis Vuitton handbag and a Slayer T-shirt serve exactly the same function in society. They help you— Is there a start to this podcast?

Jackson: (7:46) Yeah, I think we're in it.

Ian: (7:47) I was going to say, when it starts, I'm going to open this.

Jackson: (7:49) All right, let's rock. Let's get some fresh can opens on the mic.

Ian: (7:54) So, first of all, my disclaimer is I'm off a flight from Tokyo yesterday morning. I've been up since 5:00 a.m. and I've been working since then.

Jackson: (8:05) Got a nice 10k in. Thank you for joining me.

Ian: (8:11) I finished my last meeting at 7:00 p.m., and that's why we have these delicious Mexican lagers from the beer store up the road. Beautiful.

Jackson: (8:22) The last conversation we were having started with me asking about your tattoos, and I think maybe this question is related to the broader point. My first question is: What does punk rock mean to you in a spiritual sense?

Ian: (8:35) I'll tell you exactly what it means to me. And I apologize because I've told this story before, but I grew up just loving rock and roll. I have a brother and sister, eight and nine years older than me. My brother outgrew his Kiss records and handed them down to me, and that was also my first experience with art. Think about the cover of Kiss Destroyer or Kiss Rock and Roll Over. They're really amazing pieces of art, especially for a five or six-year-old kid. You're like, "What is happening in this universe?" So my journey through music was kind of rock and roll. AC/DC in first and second grade. Then in junior high, I liked Rush and Led Zeppelin. I remember the book I read when I was in seventh grade was Hammer of the Gods, the Led Zeppelin saga—which, by the way, a child should not read. They are pretty fresh, actually. But then I saw those bands. My mom took me to see Kiss when I was 13 years old, and she took me to see AC/DC. It was W.A.S.P. opening for Kiss and Fastway opening for AC/DC. I saw Rush at Cobo Hall in Detroit. I'm 13 years old, and these are my first experiences with seeing the music that I love in person. But also, we don't have much money, so we're sitting in the bleachers. My favorite band is like a postage stamp somewhere down at the bottom. Then I started skateboarding and getting into punk rock. You just find your way to that music. You open Thrasher Magazine, you see Agent Orange and TSOL, and you think, "How do I get those?" Then this kid moves from Florida. Not only does he drive a black Firebird with the gold eagle on the hood, but he has amazing punk rock cassettes: Minor Threat, Agnostic Front, MDC. Somehow we get into straight edge—which, I like drinking a beer and talking about straight edge—but "don't drink, don't smoke, don't fuck, at least I can think," as Ian MacKaye famously said.

Jackson: (10:44) And that was introduced to you specifically by this guy?

Ian: (10:57) This is real rabbit hole stuff. I realize now that you're either that person or you're not. I always was, but I didn't know that other people weren't. Anything worth doing is worth overdoing. If I'm into punk rock, then I want to know all of it. I drive an hour to Tracks Records near Notre Dame and buy a copy of Maximum Rocknroll. Then you read every review and you take your allowance and ask your mom to write checks and mail order albums.

Jackson: (11:19) I was going to say, the rabbit holes were a lot harder to get into then.

Ian: (11:22) Yeah, the rabbit holes were hard. You would read a three-line review in the back of Maximum Rocknroll, and then I'd have to ask my mom to write a check because I don't have a checkbook. I had allowance and I had a job, even, because you work when you're a kid in Indiana—that's where the work ethic comes from. So I had money—not much, but enough to buy seven-inch vinyl. You ended up in this rabbit hole. One of the rabbit holes was straight edge. It's actually worth talking about. It was an anti-drug movement by teenagers in the '80s. It's incredible, and I super identified with it. I'll find my way around the answer—I was 15 and jumping around a little bit, but it does fill in pieces of the puzzle. Ian MacKaye from Minor Threat, Fugazi, Embrace, Dischord Records. I saw him in a movie that was on television. Night Flight showed a movie called Another State of Mind. It was really about the band Social Distortion, but Ian MacKaye appears in it in the middle and he has this line where he says, "Yeah, I didn't know what I wanted to be, but I knew I didn't want to be like the football players at my school." For me at 15, I was like, "That guy is talking to me." I identify with that so deeply. So, yeah, "don't drink, don't smoke, don't fuck, at least I can fucking think" was like, "Okay, I'm with you on this, man." And I was primed for it. So to come back to punk rock and what does it mean spiritually? We were 15 years old. I think the straight edge band Youth of Today is playing in Chicago. It's a four-hour drive. We convinced Ryan Timmons's dad to drive us there, and it's an all-ages show. You go to the show and there's four bands: Bastro, Soulside, Youth of Today, and the Henry Rollins Band. We were like, "Isn't that the guy from Black Flag?" We didn't really know much about Henry Rollins in 1986 or '87, whenever that was. But while we're watching the other bands in this tiny club, Henry Rollins is just standing to my left. The guys in the band I love are standing to my right. I realized this is so different. This is the difference between being a spectator and being a participant.

Jackson: (13:47) Yes.

Ian: (13:49) That’s what it means to me. There’s the great Ted Nugent, who is a colorful character from Detroit and played in a rock and roll band called the Amboy Dukes. He said in a Grand Royal interview in the ‘90s—how did he put it? He said they were asking about MTV and he said, “I’ve got news for you. I don’t watch anything. I do shit.” That also resonated with me. So to me, spiritually, the thing about punk rock is you’re all peers and you are judged on your contribution. You are not a spectator who is meant to buy a ticket and buy merch. You are a participant who is meant to engage. I think that to me is what punk rock means. That was the unlock for me. I feel like everything I’ve been a part of after has been that in some way, all the way up to today with what’s going on with AI. I feel like a participant, not a consumer.

Jackson: (15:07) I think that’s just a message that could be quite resonant with many young people today. The first thing it reminds me of, despite him, at least on the surface, not being a very punk rock person, is spiritually. There’s that old Steve Jobs video where he’s like, when you realize that the world was created by no one smarter than you and that you can poke the universe and get some feedback.

Ian: (15:07) Yeah.

Jackson: (15:31) It’s the meme of you’re sitting in the back of the chair and you lean forward playing the video game. Call it agency, call it whatever you want. What an amazing thing to internalize.

Ian: (15:41) Totally.

Jackson: (15:41) And probably not something that really leaves you once you get it, regardless of how you get it.

Ian: (15:46) Yeah, I think that’s true. One time working with Jimmy Iovine, I asked him, “Why do you do this?” I think it was right around the time of his 60th birthday, and I was curious. Why do you get out of bed in the morning, man? He was the hardest working person in my life. He was my first phone call at 7:00 in the morning and my last phone call at 11:00 at night. You ask my daughter, she’s like, “Oh yeah, we were at Jimmy’s house every weekend,” because there was always a reason that we were meeting somebody for lunch on Saturday. Nobody works harder than Jimmy. And I was like, “What’s your motivation? Why do you do this?” And he said, “Once you’ve moved culture, it’s a high you always want to get back.” He said to me there was a before Eminem and an after Eminem, and that’s a feeling. Once you’ve done it, you just want to do it again.

Jackson: (16:36) You’ll move any mountain.

Ian: (16:37) Yeah. And so I think it’s that Steve Jobs thing. I think that was something that Steve Jobs and Jimmy really shared.

(16:44) What Makes a Scene?

Jackson: (16:44) There’s a Cultured Mag profile on you from a little while ago, and it says, “Despite hopscotching across fashion and music and crypto, Rogers’ skill set remains singular. He gets to know a cultural scene, then he brings more people into it.” Maybe to start, what makes a scene?

Ian: (17:05) Yeah, that’s a great question. And how has what makes a scene changed? I think it is a function of media in some way. There’s a McLuhan “the medium is the message” thing in here somewhere. If you think about how hard it was to create a scene with the technology of—fill in the blank—and how that’s changed. I don’t know what it would have been like before fanzines. What’s an interesting example is skateboarding. Think about the business model of skateboarding in the ‘90s. Nobody made money in competitions, really.

Jackson: (17:14) Right.

Ian: (17:42) So what you had to do was sell boards. How do you sell boards? Well, you get popular with kids. How do you get popular with kids? You get seen in a VHS cassette that gets passed around. When you think about it, it's like, wow.

Jackson: (18:01) Friction at every step of that process.

Ian: (18:03) Exactly. Yet you could actually kind of build a career that way. And people did.

Jackson: (18:07) Yes.

Ian: (18:09) And then also that, of course, determines what kind of skateboarder is popular, because you’ve got to be popular or no one’s going to buy your boards.

Jackson: (18:18) So, maybe to go back to McLuhan, you even have to be the type of skateboarder who can pop on a VHS.

Ian: (18:26) Exactly. By the way, the amount of work that they would put into those parts—because that’s literally how I’m going to eat for the next 24 months. It’s going to be based on if I can do something in this video that no one’s done before. It’s a really interesting way to move things forward. Think about the difference between that and the NFL.

Jackson: (18:29) Right.

Ian: (18:48) It’s a very different business model.

Jackson: (18:48) Very different.

Ian: (18:52) My point really was that technology is in here somewhere. I think your interview with Yancey actually covers this pretty well because you ask him, “What is a label?” A label is just a group of people gathered around an idea, and that can create a scene. It could be an artist—for example, Andy Warhol in the Factory with Velvet Underground. It also could be an artist in the sense of the Beastie Boys. They created a diaspora that I’m proud to be a part of, but it really was a global like-minded group. I was just in Tokyo and I spent a lot of my time with Rip Zinger, who I know through the Beastie Boys and is part of that. Just being with him, it’s obvious that we’re both part of that scene, even though we’re in our fucking 50s. I’m not sure what that means today. I think it might mean a lot less, because we were much more tied to the scene, either in or out of it. I don’t feel that from kids today, but maybe I’m just old.

Jackson: (20:12) I’ve had this conversation with a few different people, maybe with Yancey. The meta point that I think a lot of people have made is because everything is so much less frictionful, it’s harder for the boundaries that sort of create a scene to hold.

Ian: (20:26) Makes sense.

Jackson: (20:28) Maybe you could have a Discord server or a thing here or there, but everything on the internet is much more legible. One of the theories that I have is that friction is part of what creates the connection that says, “We’re part of this group. We’re not part of that group.”

Ian: (20:29) Yeah.

Jackson: (20:47) When everyone can move super freely, it's harder.

Ian: (20:50) I wonder if it's also, if you think about moving from living in public on Instagram and setting up your beacon to being in group chats. Like, is the group chat a scene, or is it not a scene because it doesn't need to advertise itself? It's closed by default, right? So to be a scene, does it need to advertise itself? Does it need to recruit?

Jackson: (21:19) My initial response would be it depends on what stage. My sense is that there are a lot of group chats that have started as these private containers and have gained a lot of power over time. This is kind of the classic Yancey thing—this sort of... I forget who first coined it, maybe it was Venkatesh Rao or somebody like that. They’re talking about how you have this cozy web, or you have this group of people, and then when they go participate in the public arena as the gladiator, it's almost like there's this conspiracy of people. You don't know they're actually already in cahoots with the people responding to the tweet. But it's a different thing, for sure.

Ian: (21:55) Well, I also think that responding to a tweet is such a great thing to say because you realize we just don't know at this point—that has very little purchase because that response is probably a bot, most likely. Now that those waters are so muddy, I was thinking about what is a scene in this term? Harper Reed has an amazing AI builder group, and I love it. It's really an honor to be a part of it. Also, there are some of these Silicon Valley groups that I'm in where I feel like I'm in there with people that are building things that I use every day. Is that a scene or is that a professional networking group? And what's the difference, exactly? I think about the Beastie Boys example as an interesting one because I feel like they were a part of scenes. They were part of the punk rock scene in New York, and they were part of the hip-hop scene in New York. To me, the greatest part of the Beastie Boys Book is really getting a feel for what it was like to grow up in New York in the ’80s when culture happened there. Everything that I experienced in Indiana was downstream of those things that were happening there on the ground every day. They were really a part of those scenes.

Jackson: (23:17) Yes. Yeah. Meet Me in the Bathroom, same idea.

Ian: (23:20) Yeah, those are real scenes. At the same time, the scene the Beastie Boys created almost felt reluctant. They created Grand Royal because in Check Your Head, they put a little note that said, "If you'd like the lyrics, send a dollar to this address."

Jackson: (23:39) I saw. By the way, that's some friction.

Ian: (23:43) Yeah, exactly. They kind of thought, "Well, we'll see if anyone does that." I remember we had trash bags full of those dollars, those envelopes, in the Grand Royal offices. It was quite a difficult thing to respond to all of them. To their credit, they looked at that and went, "If we just send these people lyrics, we're idiots. There's more we can do here." They created Grand Royal magazine out of that impulse, out of going, "Wait, we have an audience here." Now, was that a scene? I guess so. They created it, but it also included X-Large. Mike D used to have a record store on Vermont. You start putting pieces together. I think technology has always been a limiting factor, and maybe now, to your point, it's a great way to put it. I hadn't thought of it before, but because of the lack of friction, the friction was the guardrails that kept it. I was always a part of scenes. If it wasn't on these labels, I wasn't going to listen to it. Then there are these two friends I made in high school that just taught me that actually it's all nonsense. 99% of every genre and every scene is garbage. Your job is to find the 1% of everything that's amazing. Yeah, exactly. And to traverse. I think some people are just more oriented that way, right?

(25:24) New Culture, 99% of Everything is Garbage, Finding the 1%

Jackson: (25:24) Another cut on this would be W. David Marx, who wrote Status and Culture and a new book called Blank Space.

Ian: (25:38) I know the name, but I haven't read it.

Jackson: (25:39) He and many other cultural commentators have made this point that it’s sort of like an end of history for culture. There's no new culture being created; everything's derivative. One theory for this, if it's true—which I think is probably a grand statement—is the lack of subculture or the lack of scenes like this. To invert the question, to what extent do you see new culture forming, particularly at the edges? One theory could be that it has to be low status, and that's harder for those things to materialize. Maybe it's good when something like crypto is less popular than whatever. As someone who seems to have been very much on the edge of what was really interesting—or "cool" is a challenging word, but the edge of cool—for many years, long after you were 19, I'm curious if there's anything or where you would even look.

Ian: (26:28) Man, I haven't heard his argument, but I couldn't disagree more. That sounds like a really typical old person argument to me: "Things were better when I was a kid."

Jackson: (26:41) But I think he's probably late 30s.

Ian: (26:44) Okay, well, he's old well beyond his years. I’ll approach this in a couple of ways because I just think it's kind of patently false. First of all, my challenge would be: name one culture that's not derivative. I can't think of one. That's not how humans work. Everything that we do is derivative. We're always building on the shoulders of giants in every aspect of life. Without Robert Johnson, there's no Rolling Stones, and without NeXT, there's no iPhone. All of these things are true. We're always— We're all. Everything is derivative by definition. Also, I would argue that there's so much subculture on Instagram and YouTube. The humor is so specific. By the way, Doomscroll Forever, please, ladies and gentlemen. How about Fake Music BR on Instagram? Doomscroll Forever. I don't know if the comedy is made only for me, but it's my favorite thing on the internet, period. And really, I would say we have so much more subculture. Whatever you're super into, it's on YouTube.

Jackson: (27:04) Right. Right.

Ian: (27:58) And so I think it's—some of it's super deep. You think about things that have been around forever, like fan fiction and this sort of thing.

Jackson: (28:07) Fan fiction—sorry to interrupt you. Fan fiction is maybe a great point to latch onto, though, because I think part of the point here isn't that there's infinite depth on whatever. I want to also talk about internet niche; I totally agree with you there. I think the point is less that you can go down an infinite YouTube rabbit hole on anything you want, but that it's sort of regurgitated. It's compounding in on itself versus progressing culture forward.

Ian: (28:31) I'm still not sure I agree.

Jackson: (28:31) You don't agree? Like, in a way that it feels like...

Ian: (28:34) Honestly, I really think it feels like somebody saying, "Media used to work like this when I was a kid, and it doesn't work like that anymore." Because media physics changes. It reminds me of even, like, I remember I was at the JP Morgan conference in 2021, and I remember just this moment of watching these old billionaires sit on stage. They were furrowing their brow and asking, "When do we go back to a more centrist political dialogue?" And I was like, you just asked, "When do we go back to three channels on television?" The answer is we don't go back to three channels on television. Therefore, we don't go back to a more centrist political dialogue. I think, though, there's another—I want to give everyone who's listening, however many listeners you have... Yeah, exactly. But you'll always encounter old people saying, "Oh, there's no good music anymore." I'm not saying that's what this guy's argument is. I'm just saying you will encounter this in your life, and it's a similar argument. So here's what you do in that case: say, "What year would you say music was great?"

Jackson: (29:30) And they're 18.

Ian: (29:31) So first of all, the answer is when they were in college, invariably. Don't lead them, but I'm sure that'll be the answer. And then what you do is you pull out your phone, you type in Billboard Hot 100 that year, and then you show it to them. And they will go, "Oh, but, yeah, that's not what I was listening to." And I would say, "Exactly. In those days, you were looking at the underground, you were looking for the good shit, and now you are judging music based on the Billboard Hot 100." And so this is the problem with these things. Anytime anyone tells you something sucks, you can just say, "Shut up and do your job." It's so easy to find things that suck. 99.9% of all music, all movies, all books, all human beings, all NFTs are garbage. Do your job. Find me the 1% that's awesome. That's what I would say to him. This year, it's Twisted Teens. Greatest band I've heard in 10 years. And what are they? They're New Orleans steel guitar punk rock. Are they a part of a scene? Are they even a part of a genre? I don't know, but it's awesome. And that's all that matters.

Jackson: (30:45) Part of this maybe, too, is that you have to be looking. I think I was texting you about this—I recently interviewed Tyler Cowen and my friend Nabil, and I currently have a viral Instagram reel going crazy because Tyler was saying... I think he literally said rap is basically dead and electronica is kind of worn out. And he's waiting for AI music to get good. I think part of the implication here, too, is that you can't look in the spot you were looking prior. And there is something really fresh and interesting and new, but it's probably not quite 2025-shaped, let alone 2015-shaped.

Ian: (31:17) It also might not be your taste. I'm experiencing that with hip hop generally. I was a 90s hip hop nerd. I listen like—Pitchfork tells me this is a great new rap record. I put it on, and nine times out of 10, I'm like, "This is not for me." And that's probably just me, not them.

Jackson: (31:35) Well, maybe. Do you think it's possible that hip hop is significantly less artistically innovative than it was 10, 15 years ago? It would make sense given how dominant it's been.

Ian: (31:45) Yeah, but I think you could say that about every genre, right? I mean, start with the oldest—go put on a new blues record from Alligator Records. Is it innovative? No, it is not innovative in the slightest. But I also think you always have these moments when art forms are new and the best thing about them is there's no rules. I would argue that hip hop is dead since you could say, "That's not hip hop." And then everything else is exceptions to the rule. As soon as you could say, "Oh, that's not hip hop," well, now actually you've made a box and you tried to put the art in a box. And it's only the people that escape that box that are going to be interesting. And I think certainly electronic music is that. Electronic music was so exciting when it was new and it was like, "What is this?" The first time I heard the Richard D. James Album by Aphex Twin, I was like, "This is the future of music, period." I don't even know what to call it.

Jackson: (32:47) For what it's worth, Tyler was definitely praising Aphex Twin.

Ian: (32:49) But it's a great example because if in the 90s you were like, "Oh my God, this is going to be so exciting," and then ultimately you realize that electronic music wasn't even a genre, it was just an excuse to take drugs, then you were super disappointed. Because Aphex Twin really felt like the future of classical music. And so now you're just like, "Oh no, it's just people four-on-the-floor getting high in a..."

Jackson: (33:19) 90% of everything is boring.

Ian: (33:23) Yeah, exactly. I think it's the same with hip hop, right? Like every other genre, most of it's terrible. It's not like a genre is good—it's not like hip hop is good and country is bad. No, most hip hop is terrible. Most country is terrible. And guess what? There's amazing shit in both, too, if you're willing to do the filtering and look. I also love the exceptions that prove the rule. The one for the past year is Clipse.

Jackson: (33:24) Yeah.

Ian: (33:52) One of my favorite records of the past couple of years is the Clipse record. I mean, Push is so talented as a rapper. He has everything that I want: he’s clever, he has wordplay, he has swag, he’s smart. He’s also "dumb"—he’s not dumb. He’s super smart, but he knows when to play dumb and to have it be about drug talk. To me, it's everything that I want. Having Malice back—we saw Clipse in LA, and when Malice walks out on stage, it's like I feel like everyone in the room wanted to start crying. To me, Clipse doesn't even sound contemporary. It sounds like the hip hop I grew up on.

Jackson: (34:43) Between that feeling like something you used to love and also being new, versus just feeling nostalgic.

Ian: (34:51) Yeah. I think, by the way, I'm comfortable at age 53 saying I don't know, and I don't feel like I need to know. It's all about tier one to you. Having kids teaches you that as well. I don't care what they listen to; I just love that they love music. We all realize there are no absolutes there. I'm a music snob, but I also know there is no such thing as good or bad. Personally, I think Ol' Dirty Bastard is the most talented vocalist of the 20th century. I’ll probably be hard-pressed to find anyone who agrees with me, but that's okay.

Jackson: (35:30) Ol' Dirty Bastard. Why do—we're dangerously close to the taste discourse, but across artistic mediums, the people with good taste seem to converge on similar things. It's almost a recursive question.

Ian: (35:47) Mojo magazine. I read them all. I don't know if you know the magazine, but it's a British magazine that's been around for 50 years, I think. I feel like there was a Joni Mitchell cover a couple of issues ago that said 50 years on it.

Jackson: (35:59) Oh, cool.

Ian: (35:59) Hey, Mojo, I don't really know how old you are; I apologize if I got that wrong. But I read it cover to cover every month. They are kind of like where we converge on good taste in a way. Guess who's on the cover this month? The Rolling Stones. Like every other year. But they do have things that are worth following, and oftentimes I discover things through that channel that I wouldn't have discovered otherwise. That's the role that Pitchfork served for a very long time—less so today, unfortunately, but still sometimes.

Jackson: (36:40) But it's kind of outside of scenes. The people that I think are the coolest or the smartest seem to generally trend towards similar types of stuff, even if they're coming from very different scenes. The fact that Tyler Cowen can talk to Rick Rubin about music—granted, maybe they both just truly love music—but the fact that those two guys who are very dissimilar have converged. You and Rick is maybe less surprising, but...

Ian: (37:07) But I think Rick and I probably converge less than you might think. One of my favorite things to do when I visit him is to just sit and play songs. I've never heard most of the songs he plays me, and he hasn't heard most of the songs that I play for him. I was just talking to someone about where we come from, and that's actually why I went down the path of talking about the rock and roll side first. You kind of have to see the arena rock to appreciate the punk rock. I came from heavy metal, so I never got pop-punk. That doesn't mean pop-punk is bad. It just means that if you were into Britney Spears and then you discovered NOFX, that makes sense to me. Since I came from "heavy heavy," I'm more likely to go that way. We all just have this personal experience, which is why tier one to the individual is much more important. For me, I did digital music for 20 years, and what was important was that we enabled people to do whatever they wanted to do with music. I never wanted to be a music critic. There's a time for that when you're sitting with friends, but what I loved about Winamp was you could just play anything you wanted to. I don't care what you play; I just want you to love music. If you're loving it, that is fantastic. The other side of it is it really should just be about sharing. Another way to put this is: no three-star reviews. That's what pisses me off about Rolling Stone. It used to be all three-star reviews. You guys are pussies.

Jackson: (39:02) Three out of four or three out of five?

Ian: (39:02) Three out of five.

Jackson: (39:04) Yeah. This is why I love the four-star scale. You have to choose; you have to go thumbs up or thumbs down.

Ian: (39:10) Yeah, which is all I want. If you really want to do me a favor, if it's three stars, just leave it out. Who cares? There are only two things I care about. One is: I didn't know about it and it's awesome. Please tell me about that. The other is: I might have wasted my time on it—or in the old days, wasted my money. If that new record from an artist I was probably going to buy really sucks, please warn me. Those are the only two things you need to do. "This is kind of okay"—I don't have time for that. I'm too busy trying to find the good stuff.

Jackson: (39:17) I was right about it.

Ian: (39:46) Don't tell me—don't tell me something is mediocre. What is the point?

Jackson: (39:49) Totally agree.

Ian: (39:49) But I would also say don't tell me something is bad. Duh. Just tell me the good stuff. Really. People just talking about shit they don't like—it's really, at this point, what is wrong with you? What's the point? Tell me something that's worth watching.

(40:09) Niche, Quality, and The Blockbuster vs. The Snowball

Jackson: (40:08) I agree. We talked about it, or at least we talked around it a lot. You've been a strong advocate that the Internet is—the way I put it in the past is that it's about niche at scale. It's not about the mainstream. There's an idea that you talked about with Rick a couple of interviews ago, which is the Blockbuster versus the Snowball. I'd love to hear you just riff on that briefly, because I thought it was one of the more interesting cuts on this. It feels like every year that passes, it's describing modern culture better.

Ian: (40:41) Yeah. All credit on this goes to Umair Haque, who wrote this piece called "The Blockbuster versus the Snowball" in, I think, 2003. Really prescient. There was actually something that came before that. I'm trying to come up with the name, but there was somebody around 2000 who basically was saying that the popularity of Fox News was due to the Internet. The point was that when you have limited distribution—you have two newspapers in a town—to get the most viewership, they're going to drift toward the middle. But the point was, when you have unlimited choice, then you've got to stake out a position. I actually think John Higgs, who's my favorite author, has a contemporary theory on this to bring this all the way to today. You really do ask yourself, "Okay, how do you get the viewership?" Again: limited distribution, two newspapers in a city. If you want the maximum viewership, you've got to be centrist. Well, now on the Internet, if you want maximum viewership, what do you have to do? You have to be polarizing. I like the way John put it; I find it actually very optimistic because what he says is those two centrist newspapers didn't really represent any of us. They were more centrist than any of us as human beings actually are. Now, his theory is that media is so polarizing that it doesn't actually represent any of us.

Jackson: (42:10) Oh, it's optimistic in that way.

Ian: (42:10) It's optimistic in that way where we—

Jackson: (42:13) We were deluded prior into thinking... because I was going to say it was more optimistic when they were converged because we got to all believe we were really similar. But that was a delusion.

Ian: (42:22) Yeah, it was an illusion. And by the way, maybe that is a positive way to live. I mean, I fell for it. I grew up in all-white Goshen, Indiana, watching Sesame Street and Diff'rent Strokes, and I really believed that we were all the same. It took me moving to big cities to realize that racism was real. I didn't feel racism when I was growing up because media taught me it was over. So I agree there's something positive in that. But it's like what I was talking with one of my daughters. She made the comment, "Everyone's mad about Bad Bunny at the Super Bowl." My thought, having the John Higgs thing in my head, was: "But are they?" In other words, if I walk out on the street right now and start asking people, "Are you upset about Bad Bunny at the Super Bowl?" my guess is they're probably going to go, "No, Bad Bunny's cool." The polarizing algorithm, which is polarizing by definition—intentionally—would make you think that everybody's mad about Bad Bunny at the Super Bowl. So what Umair had said in 2003 with "The Blockbuster versus the Snowball" is that it is media physics. I don't know if that was his term or mine, but that was the way I thought about it. We went from limited distribution to unlimited distribution. The media I grew up with is limited distribution. There's only 13 channels on television. There's only so much FM spectrum. There's only so many magazines you can fit at the Hallmark store. That's limited distribution. But the Internet is: "I'm going to make MrTateMyBalls.com." And guess what? I'm now meme-ific. That's the unlimited distribution Internet.

Jackson: (44:15) Yeah. Your TAM is 8 billion.

Ian: (44:19) Yeah, exactly. And so what Umair said is that in the old world, when you're making a movie—especially in the '80s or '90s—you're not trying to make Citizen Kane. You're trying to get people to go to Theater A instead of Theater B this weekend. If you've got an extra $2 million, where do you invest it? Do you invest it into making the movie better, or do you invest it into marketing? You're going to put it into marketing because I just need people to go to Theater A instead of Theater B. In the new world—and he said this in 2003, really predicting House of Cards, I would say—he said quality is hyper-efficient, not marketing. If you have the choice, you're going to put that money into making the product better, because the only thing that actually works is word of mouth.

Jackson: (45:09) And you're competing at a global level. This is Reed Hastings talking about Netflix competing with sleep, in a sense.

Ian: (45:21) Yes, exactly. If you listen to A History of Rock Music in 500 Songs—which I recommend—you'll hear him say every episode: "If you enjoyed this show, please tell just one person." The best way for creative works to reach people is word of mouth. That is definitely true today. I'm actually okay with that. I think that's not a terrible outcome. Coming back to what I was going to say earlier about people enjoying whatever music they want: all I've ever wanted is efficiency. That seems silly, but I grew up with this pop music radio where I could recite so many songs that I dislike. I know the whole song. I know all the lyrics. And then if you said, "Do you like that song?" I would say, "I hate that song." That's because we were just inundated. Because of limited distribution, we were inundated with things we didn't want to hear. Yet there's incredible stuff that's not reaching us. That inefficiency is always what I've wanted to solve. If you would like this, I want it to reach you.

Jackson: (46:29) Kind of a beautiful cut on efficiency. It’s meritocratic, in a sense.

Ian: (46:37) And if you don't like it, okay. I don't want to force it on you. I don't want you to listen to it until you like it—except for Twisted Teens. You're not going to like it the first time, but by the 10th time, you will be hearing the melodies in your sleep.

Jackson: (46:49) That happened to me with Yeezus. For sure, that happened. Did you listen to Cameron Winter?

Ian: (46:53) Yes.

Jackson: (46:54) It happened to me initially with him. I was like, "I don't..."

Ian: (47:01) I definitely agree with you on Cameron Winter. Those were genuine earworms. Really creative. I felt like the Cameron Winter record is sort of like Astral Weeks for this year or something. It had that kind of "I didn't know when a song was over" feeling, like on Astral Weeks. And I love the Geese record. I think the previous record I thought was great, but I felt like it was almost like a bunch of talented musicians in New York that were sort of like— Yeah. I was like, "Oh, well, that's the Radiohead reference, and that's the Thin Lizzy reference." You could feel it. The new record—I mean, the latest one—I just... I know people love to hate on them, and I'm like, "What are you talking about?" This is genuinely challenging. You put the most challenging song at the front of the record? I love that. That's like a Ween move. Melodies are great. The playing is great. And the real key is the guitar. Melodies get stuck in your head. Same for Twisted Teens, by the way. There's steel guitar, so you've got two melodies. The guy who writes the songs has amazing melodies, and then you've got the steel guitar in the background. There's like this second melody. I think that's why you hear it in your sleep. It's really insidious. But yes, Yeezus, by the way—I hated that album—

Jackson: (48:13) When it came out?

Ian: (48:16) It grew on you?

Jackson: (48:17) Oh, yeah. I mean, it's... yeah. But I literally hated it. I was like, "Kanye, this sucks."

Ian: (48:23) Can I tell you my personal story with that record? First of all, I don't think I've ever said this publicly, but there's a project that I would like to do. If anyone would like to do this with me, please contact me. I'm afraid I'm actually going to have a lot of people contact me because we all have stories. The book is called People Who Tried to Help Kanye.

Jackson: (48:39) I know at least a few.

Ian: (48:41) Yeah. Because he is truly, truly talented. The first time that I met Kanye, Guy Oseary asked me if I would come over to his house and talk to Kanye because Kanye wanted... and Guy was smart on this. He's like, "I think what Kanye's trying to do is like his Grand Royal. Will you come talk to him?" I'd love to. So Dark Twisted Fantasy had been out. It blew my mind.

Jackson: (49:10) Much more palatable on the first listen.

Ian: (49:11) I think it's still... yeah, true. But that's why the story's good. So I go over there and sit with Kanye. We have a pretty cool conversation—interesting conversation, actually. One of the things, talking about boxes, he said, "I feel like music is a box and I need to get out of it." He's like, "I'm done." One funny thing from that meeting with him is he goes, "Yeah. I mean, I made a record that's a 10 out of 10 on Pitchfork—Dark Twisted Fantasy." He said, "My punishment is that I have to do press and tour." He's like, "I made a record with Jay-Z. There's nowhere to go from here but down." I was like, "You made a record with Jay-Z?" He's like, "Yeah, you don't read the news?" And I was like, "No." So you could put it on the timeline because I guess he'd made the record and people were talking about it, but I didn't know about it and the record wasn't out yet.

Jackson: (49:56) This is Watch the Throne.

Ian: (49:57) Watch the Throne. Exactly. But I left Guy's house that day thinking Kanye is never going to make music again, because that's what he told me. He told me he wasn't going to make music anymore. Music is a box. He said when he was in Chicago, he felt like it was even a box; he had to get out of the box. Music is a box. "I've got to get out of the box." And I was like, "Wow. Kanye's not going to make music anymore." That's how I left. I left there believing and feeling that. One day Mike D told me, "You know, Kanye's up at Rick's working on a record." Mike's in Malibu, Rick's in Malibu. And I was like, "Oh, really? I didn't think he was going to make music anymore." So the fact that what came out of that is Yeezus makes perfect sense to me. "As soon as they like you, make them unlike you. 'Cause kissing people's ass is so unlike you. Only rapper compared to Michael." Yeezus is punk rock. It is so punk rock. It is just from the moment it starts. It's hard, it's difficult, and he is as good an emcee on that record as almost ever. Although, one Kanye thing—my daughter would be so bummed that I'm bigging up Kanye because she's so disappointed with the swastikas and everything, for good reason.

Jackson: (51:26) Yeah, I think you can hold both of those things.

Ian: (51:27) There's nothing cool about a swastika, man. Like, dude, come on.

Jackson: (51:28) The—the—

Ian: (51:36) The Art of Rap. I think it's called. Search "Art of Rap Kanye" and watch him do a verse from Dark Twisted Fantasy. I promise you never knew how good that verse was until you hear it acapella. I mean, wow. Anyway, I just wanted to say that Yeezus is amazing. Yeah, exactly. I mean, I know this is a controversial topic. It's not so controversial to me. I have Sly Stone tattooed on my arm. I like music, and we don't always share political views with the people whose music we enjoy. Those are strange bedfellows.

Jackson: (52:33) Do you think he'll ever make anything that good again?

Ian: (52:38) I don't know. I mean, I hope so, but I don't know. It's not really for me to pontificate. To me, the more interesting question there is: how does the machinery interfere with the art? I think that's a lot of the story. There are personal issues; he's a human being with his own issues. At the same time, everything's running. That's why I think the People Who Tried to Help Kanye book—which is a joke, obviously—is one of the things that I find sad about it. There are so many people that really believed in his genius, that wanted to help, and they just couldn't.

Jackson: (52:38) Yeah.

Ian: (52:59) And that's unfortunate.

(53:35) Brand, Selling Culture Before Product, and The Age of the Individual

Jackson: (53:35) I want to talk briefly about brand. We briefly met in early 2020, and I was building this gaming thing. There's this line you said that stuck with me for years and years—and I don't even know if we totally followed the advice as much as we should have—but you said, "Never forget you're selling culture, not product." What does that actually mean?

Ian: (54:00) Well, I think that selling culture is a prerequisite to selling product is sort of the way that I thought about it. I really loved working at LVMH to see that. The great thing about LVMH brands is that in some ways they're caricatures of brands. What I mean by that specifically is I work with Dr. Martens today, and you could be excused for saying, "Well, there's a lot of utility in what we sell." It's a black boot, it's comfortable. But you're kind of doing yourself a disservice when you do that because you're missing the real reason that motivates someone to buy something. There's a great human being, David Slew, who worked with Tony Fadell for a very long time—still works with Tony—and he taught me something about consumer electronics, which is that the front of the box is for the heart, the back of the box is for the head. The front of the box is that lizard brain: I want that. Oh, that's cool, shiny object. The back of the box is: I've got to justify to my partner why I spent $500 on this. Well, look, it's got this feature and it's got that feature. Look, it's a great buy. But it's that same thing—you're selling the part that touches you first. Once you've crossed that barrier, now I can sell you the product.

Jackson: (55:35) It's also funny, it's telling that Apple products have very little on the back of the box.

Ian: (55:42) Yeah. Well, the Apple thing over the past 20 years is just crazy. You couldn't have—in fact, I think that's an interesting timeline to look at because if you'd have told me in 2006, if you'd have described the iPhone to me, you'd have said there's a mostly proprietary platform that's going to take 30% from anybody who wants to have an app on their platform. I would have said that's not the internet. The internet is open and available to anyone, and we're about open source and open access. I just would have bet against it all day long and obviously I'd have been very wrong. But yeah, I think there are so many lessons in that. I think the bigger lesson in Apple is the Clayton Christensen one: when the technology is not yet good enough, the integrated solution always wins. And they had that combination of software and hardware that a company like Sony never knew how to do.

Jackson: (56:52) The funny thing is that I would agree with you. There's this classic—I don't know if you ever read it—Ben Thompson has this piece on what Clayton Christensen got wrong about the iPhone not getting compressed from the bottom. It was almost both of those things. It's a really unlikely thing, to your point, in so many ways.

Ian: (57:13) No, and by the way, it's super personal for me because when I was at Yahoo in the 2000s, our whole MO was: "Yeah, Apple's killing it right now, but the disintegrated solution comes next." I took a trip to Japan with Dave Goldberg in 2005 to try to convince Sony to join Yahoo and Microsoft on the fight against the disintegrated solutions that were going to ultimately overtake the iPod. But I think that's actually what Apple is. I think it is Clayton Christensen. I would love to talk to Ben about this because what Clayton Christensen says is the integrated solution wins when the technology is not yet good enough. As the technology becomes better, the integrated solution must move upmarket to solve bigger problems. Now, I think they did create a lock-in with FaceTime, iMessage, and AirDrop, which has prolonged that. That's probably the lesson: there are ways of creating network effects that create lock-in.

Jackson: (58:29) Well, and frankly, back to the question, it's also a cultural object. How much of it is iMessage and how much of it is having an iPhone? You could debate it, and I'm sure it depends on the person, but the fact that they've created a product that ultimately is like a vanity object in some sense and this ultimate utility object is kind of strange. Well now, I think you can use some software, you can use Beeper or whatever, and get in there anyway. Also on the brand note, you have a classic line—maybe it's from you or maybe it's from Bernard Arnault—but storytelling plus time equals value. I've thought about this a lot while we were building this gaming thing, 100 Thieves, in part because we had the brand and then we had all these influencers and creators underneath it. We live in the age of the individual in so many ways. How can brands accumulate value, or maybe accumulate meaning, in a way that people can't? Because it's so much easier for Mr. Beast to get the low-hanging fruit of attention compared to a brand or a label.

Ian: (59:27) Mr. Beast is an individual, not a brand in this conversation.

Jackson: (59:30) Well, so this introduces an interesting sub-question which is, notably, perhaps most of LVMH's signature brands were originally namesakes. And so maybe there's an element of that. The metaphor I always use is like: it's really cool that Louis Vuitton is like this camera, and Virgil can hold that camera for a little while, and then Pharrell can come in and hold that camera, or whoever. Jonathan Anderson comes in and holds the Dior camera and you get a—it's Dior, it's super Dior, and it's Jonathan. To me, Mr. Beast is not that. Maybe at some point... you talked with Rick Rubin about this at one point where you were like: could this be done with the Beatles or with Daft Punk or something? But it seems very few new brands are being created. It almost feels like brands have this liveness that you can't even—I realize this is a very convoluted question—but there's this tension between: if your goal is to succeed in the near term or even the medium term, you're way better building around a single individual. If your goal is to last 10 years or a hundred years, you're way better having a brand or a label.

Ian: (1:00:40) I love this question. I don't find it convoluted; I think it is that challenging. I think actually maybe it always starts around an individual. And I think you're right that there's always few brands that get created relative to the number of people who try. It's just like music where you're always going to have more aspirants than you have success stories. And the winners are maybe also somewhat unlikely; it has to do with timing, has to do with other things. In other words, you're right: the brands that you're talking about probably did start out as individuals and then over time they live on. I had that conversation with Rick and I would love to see people do this with music.

Jackson: (1:01:26) Probably harder with music than a product, which is part of it.

Ian: (1:01:31) I think, though, that the Beatles is just a great example where the Beatles could come to represent love—they could be just spreading love and joy. And also, Louis Vuitton's been gone a long time. Dior's been gone a long time. Christian Dior's been gone a long time. Yet the brands are bigger than ever. So first of all, I think there is something mechanical to that. If you look at brand marketing for a great brand—and I would say Louis Vuitton's interesting—which are there more of in the world: people who love Louis Vuitton or dislike Louis Vuitton? It actually might be dislike. I don't know the answer to the question, to be honest, and that's not a diss at all. I'm just saying that's okay. You have to remember that Bernard Arnault is the wealthiest man in Europe and probably 85% of the population are not his customers. That's okay. The goal is not to appeal to everyone; the goal is to appeal strongly—his product especially.

Jackson: (1:01:32) So.

Ian: (1:02:34) Yeah, but I think for all brands—

Jackson: (1:02:38) Look, even when—to go back to Mr. Beast, perhaps this is the tension—

Ian: (1:02:42) Mr. Beast doesn't appeal to everyone.

Jackson: (1:02:44) But he's trying to—I don't know.

Ian: (1:02:49) Is he? I'm not sure. I've got to look. When you're the most popular, it's like, "Oh, everybody loves Britney Spears," when I was running Yahoo Music. But still, if we put her on the homepage, less than 30% of people would click. You put a picture of a dog and a cat hugging on the homepage and 70% of people would click. So I just think that culturally, culture never appeals to everyone. There's a great Seth Godin quote: you should find yourself a nickel anytime you use the word "everyone" or "nobody," because the moment you say it, every word that comes after it is wrong. It's not true. There's never an "everyone." Nothing's for everyone; nothing's for nobody. And so then what you're doing is you're trying to make a business out of what you love to do. I always point to Satisfy because I've had a close-up view of watching Brice build Satisfy running. And he's just had incredible patience—way more than I would have had if I were doing it. He had a great thing I heard him say to another young brand owner recently where he said, "Look, if you think now's your time, then you already missed your window. As the brand, you always have to have in mind that your time is tomorrow; your time is yet to come." I just thought that's such an amazing way of looking at it, because what that means is that you have an expansive vision and you know it can go somewhere else. The other is when you look at the marketing of a Louis Vuitton and you go, "Well, look, they do magazines, they do outdoor, they do online, they do Google Shopping, they do all this. What works? Where's the leverage?" And when you do the research, the answer is "everything." At different levels, of course. They all have different ROI, but they all have positive ROI, which means it's literally a machine where you put money into the marketing and it makes the brand bigger for tomorrow.

Jackson: (1:04:44) And nothing is compromising tomorrow, perhaps.

Ian: (1:04:48) Yeah, exactly. And you have to have that very long time horizon. I think the biggest problem that people have is they don't really understand what it means to build a brand. Building a brand is like building an artist. Artists are rarely popular in their lifetime, and the only way that you can kind of beat that is to create your own context. So I think, generally speaking... well, I mean, look, I think Golden Goose is a great example. I was introduced to Golden Goose through Virgil because Virgil was a Golden Goose fan. I didn't know Golden Goose before. That's a great example. I don't know the exact numbers—I think I maybe talked about it on Rick's podcast—but it was a slow go for 15 years. Let's say it took 12 to 15 years to get to 20 million, just roughly. I don't know if it's 15 or 20, but order of magnitude. And then over the next 15 years, it went to 500. Deep in the compound. Yeah, exactly. But I think that, to me, that's also generational. It kind of takes a generation to prove itself, and then—

Jackson: (1:05:45) Can't grow too fast.

Ian: (1:05:46) It's impossible. So anyone who thinks—there was an entrepreneur who started a fashion brand here in Paris a few years ago, and I sat next to her—she's a good friend—at a dinner. The brand was going okay, and I was like, "How are things going?" And she said, "There's something you said to me when I was raising money that rings in my head every day." And I was like, "Oh my God, I'm so sorry, what was it?" She said, "You said to me, 'Fashion brands are not venture businesses.'" And what I meant by that was venture has a certain time horizon, but to build a brand—and I don't think it's just a fashion brand, I think it's brand—this is like a generation. And you're not really there until a Virgil can say, "Yo, that was my shit when I was 15." That's how long it takes.

Jackson: (1:06:40) Yeah. It's almost like 10 years is the—you know, it's not even a conversation until you're 10 years in.

Ian: (1:06:43) It's not even a conversation because you have to have—

Jackson: (1:06:46) Yeah, one other thing.

Ian: (1:06:47) Look at The Row. Mary-Kate and Ashley: who took them seriously? They had to stick around long enough that people were like, "I guess you guys aren't going away." And then it's like, "Oh, well, now we can look at the quality."

Jackson: (1:07:01) Right. Before, it was the gimmick.

Ian: (1:07:02) Before it was a gimmick and like, maybe you got lucky and I'm sure you can't do it again next year. But after that 15-year mark, people are like, "Yeah, it looks like you guys know how to do this." I just think that that's human nature. And I think most also... and I'll tell you, knowing Brice at Satisfy—I talked to Brice today because I know he was going to go to the Kevin Morby show last night.

Jackson: (1:07:29) Night.

Ian: (1:07:30) I was like, "How was the show?" He was like, "Oh, I gave my tickets away. I was in the office till 11." He's 11 years in on this brand, right? And you find me somebody that works harder than Brice. They don't exist. People discount that. People think like, "Oh, well, how hard can it be to make running shorts?" But no, he's steering that ship 24/7 with a singular vision that, no matter if it was up or down yesterday, it's on tomorrow. Most people simply don't have what it takes.

(1:08:12) Aggression, Patience, and Being Pushed

Jackson: (1:08:12) For people like that—obviously him at a very targeted focus level, maybe someone like Bernard Arnault at the larger scale—the defining trait, at least as you're describing it, is patience. I think that sounds right. When and how—my assumption is certainly for Bernard, but probably for Brice too—is that there's an intensity and aggression that shows up amidst the patience, for sure. Is that true? And if so, how does that show up?

Ian: (1:08:44) I think that's a great—what a unique combination of traits, right? And that's why I look at them with a lot of awe, because I don't have the patience. And also, I think partly coming from tech, that's a...

Jackson: (1:08:57) ...where tech doesn't love history or time.

Ian: (1:08:58) I mean, look at what we've been through in AI this year where we went from token maxing to token economizing in 30 days, right? The whiplash is severe in our industry. And also, by the way, that's why a lot of those kind of people have a very difficult time in this industry. Not everyone's built for everything. I realized that just being at a startup—and I've done 13 startups—what I realized is I'm kind of built for it. I'm built for like, "Guess what? I'm coming in tomorrow, I'm working hard, and I don't care if yesterday was shit. I'm coming in today with a smile on my face and I'm telling everybody everything's going to be great." Not everybody is built for everything. But I think those people that are great at a brand do have—I mean, Jonathan Anderson is certainly one of those people where he has all of the creativity, but he's also competitive, intense, and hardworking. There is definitely a special mix of traits that makes people great in that world. There are very few people that really have it. The Gallianos, the Jonathan Andersons, and the Brice Partouches are few and far between.

Jackson: (1:10:08) I think you said you aren't patient. My sense is that in some sense you are definitely impatient, but in another sense you've actually been very patient. Particularly on the technology side. You've had the right level of patience to see out maybe things that felt inevitable to you, but certainly weren't inevitable on an obvious time horizon—not the least of which crypto and streaming music, or internet music. Really, you basically rode internet music for 15 years, maybe longer.

Ian: (1:10:09) Yeah. Do you?

Jackson: (1:10:11) Yeah. I don't know. How are you—you clearly are patient in some dimension.

Ian: (1:10:53) I think that music, though, is just—that's maybe the obvious one because... but also I think there's just personal things in that. I didn't know how to do a business at all. So the fact that someone wanted to pay me to make websites was just like, "Okay, great." And then all this dot-com stuff was happening and I was like, "What's going on? I don't even know what 'public company' means." That's not part of... my mom worked in a factory and then became a nurse, and my dad was a fireman. We didn't have investments in public companies in my family. I didn't know what it even meant. So I just never had that. I just didn't know what else to do. And so, what was I doing?

Jackson: (1:11:30) You did it for another 12 years after you had already...

Ian: (1:11:35) Right. But during the dot-com bubble, I was making music apps. After the dot-com bubble, I was making music apps simply because I didn't know how to do anything else. And I was just passionate about it, I think, to be honest.

Jackson: (1:11:43) But let's say Yahoo. You're trying to do a five-dollar, all-you-can-eat subscription music service. You're trying to do Spotify at Yahoo in 2004?

Ian: (1:11:52) 2004.

Jackson: (1:11:53) 2004. And then you guys sell to Apple in 2013. My sense is it wasn't like that was the only thing you could do for the next eight years.

Ian: (1:12:06) Yeah, that's a good question. I wouldn't say it was patience, though. I think it was because, at the time, it was frustrating. When I was at Yahoo Music and I'm arguing with Lyor Cohen about music streaming rights, that wasn't patience. That was genuinely frustrating.

Jackson: (1:12:21) You have a great thing on your blog about the "context talk" in 2007 or 2008. It's kind of right in the middle of that period. You're like, "Come on, people."

Ian: (1:12:30) Yeah. That one keeps coming back to me. The "content versus context" thing. I was definitely onto something there. I didn't realize that I would still be thinking about that one today. Well, another way to look at it is like, I've always just tried to find what's the technology people are going to hate next—from file sharing to streaming to crypto to now AI. What's the technology people are going to be really angry about tomorrow? How do I get into that one? That was never intentional. I just like new disruptive things. And it turns out that new disruptive things are often disliked. But music is—obviously I talk a lot about music here because it's what I'm qualified to talk about. I'm genuinely qualified to have a conversation about music. The rest of it, I'm sort of an armchair historian. So I think that's why the music one makes a lot of sense. And also, I'm very lucky that I got to come work at LVMH because I'd also reached a level in the music business. I had three nice outcomes in music, which is what people look for: people that have won before. And I'd won a couple times.

Jackson: (1:13:47) You kind of did it.

Ian: (1:13:51) From my perspective, I did what I set out to do. I built this thing in college that was a streaming—you search for music and you could stream it. And it was the early '90s, and then in 2015 it was on every iPhone. I couldn't have been more proud. That's a career. I've had a career. I could be done now and I would be quite satisfied with what I did.

Jackson: (1:14:12) That's my point: you were patient enough to see that through. Whether or not it was fully—

Ian: (1:14:15) I would say lucky enough to see that through, really, because it was not my idea. It was Dr. David Fenske at the Indiana University Music Library who gave me a job with the task to move the reserve listing materials from behind the desk to workstations throughout the library. I kept doing that over and over for a lot of years. There were a lot of people who cared way more about my career than I did: John Silva, probably Mike from the Beastie Boys, Jim Evans, Dave Goldberg, Rob Lord, and ultimately Jimmy. I remember Jimmy calling me. I was locked out of my own house, sitting on my back steps. My phone rings. It's a 310 number. I answer it. "Ian! What are you doing? Ian, you're a major league player. Why are you playing in the minors?" And I'm like, "Oh, Jimmy, I work my ass off at my startup, man. Why don't you just buy my startup? Why are you being mean to me? I'm already locked out of my house, dude. Why are you yelling at me?" He's like, "Get out of the minor leagues." But my point is, Jimmy saw something in me that I didn't see.

Jackson: (1:14:16) Yeah.

Ian: (1:15:24) So that's why I would say I was lucky to be able to do it much more than I was visionary or patient. I had something, and I really have a lot of pride in that, because I think one of the things that Jimmy Iovine and Bernard Arnault share is they see something in people. The story of Bernard Arnault hiring John Galliano is that Galliano comes into his office, as it was described to me, in a leather vest, no shirt, dreadlocks, and flip-flops. Mr. Arnault's assistant tries to send him away, and Mr. Arnault's like, "No, no, no. I've heard good things about this guy. Send him in." Mr. Arnault hires him on the spot. I watched the Tom Petty and Bruce Springsteen documentaries, and you see Jimmy yelling at them, and it gives me a pit in my stomach because I know what it's like to be yelled at by Jimmy. But then I'm like, "Hey, I was yelled at by Jimmy, too." That's what Jimmy does: he takes people that he thinks have promise and he gets them to do things that even they didn't know they were capable of. And so the fact that people like Jimmy Iovine and Bernard Arnault have tapped me on the shoulder and said, "Hey, I think you can do more," that's the real honor.

(1:16:52) Translating New Technologies, Empowerment, and Agency

Jackson: (1:16:50) I think you are someone who's spent your career communicating these new technologies that might be inevitable in some sense, but are certainly not here yet, to the world. And I think you've done a good job of communicating, particularly outside of the existing community. My sense is that while there are some notable exceptions, most people in the technology world are decidedly bad at this—at talking to the rest of the world.

Ian: (1:16:51) Yeah.

Jackson: (1:17:20) Why do you think that is? And what do you think has made you good at it?

Ian: (1:17:25) It's really funny in AI these days. You would think the AI people should start with, "Let me tell you why this is going to benefit humanity." And then once I've told you, "Look, this is going to be incredible for learning. It's going to bring new opportunities to people around the world that didn't have them before"—once we've gotten through all that, we can say, "And also there are some risks. Let's talk about those risks." It seems like the heads of the Frontier Labs have just gone the other route.

Jackson: (1:17:59) They've started to change the tone, but man—

Ian: (1:18:01) Yeah, Sam has started to reverse course a bit.

Jackson: (1:18:05) Maybe part of it is they just weren't talking to anyone. Sam was writing these blog posts in 2018 and nobody—

Ian: (1:18:10) Nobody was listening. Yeah. So, but I think for me, first of all, I've always worked with artists, and that's also easier, right? It's like, "I want to help your artistic vision come to life."

Jackson: (1:18:27) This is in service of that.

Ian: (1:18:28) Yeah, it's in service of that. And that can't possibly be wrong. You know what I mean? There's no way it can be wrong. It's a beautiful thing about art. Art is an incredible shield. As soon as you've said it's art, it automatically doesn't appeal to everyone. So it doesn't matter if you like it or not. I think that's one thing. Also, the punk rock thing does come into it a bit because, for me, technology has always been about empowerment. I don't mean that in some corny, political way. I just mean I didn't have a voice and I didn't have a way to reach the people that might like what I do, and now I do. Those things are quite easy to explain, in a way. And they're also easy to identify with if you're talking to the right people. I always say that if you ever made a fanzine with a Sharpie and a photocopier, then you understood the internet the moment you saw it. But that's not everybody. Those are the people that I talk to. I'm like, "Hey, look, you can use—"

Jackson: (1:19:35) Those weren't obvious tech people, critically.

Ian: (1:19:37) Right, exactly. But they were people that were still primed to get it.

Jackson: (1:19:42) Primed to get it.

Ian: (1:19:42) Exactly. They were primed to get it. And I do think that's a very key part of my worldview. I realize this more as I get older, because I think where I really don't connect with people is when they think about mass culture. There's no way for me to get my message across, and we're probably not going to relate to one another either.

Jackson: (1:20:07) It's back to the guys talking about when we're going to go back to the center.

Ian: (1:20:11) Yeah, exactly. Like that's kind of like—but I think that that's probably true. I grew up mail-ordering records and watching skateboard videos on VHS. Therefore, the internet spoke to me. Now, if you loved top 40 radio, then you were the person that was like, "Why do we need the internet?" So I think that's the other part of it to me. I heard a great quote: Sal Khan from Khan Academy was on David Eagleman's podcast last year. He did a two-parter on AI and education, which was super good. Sal Khan just said this offhanded remark that I think about every day. He said Khan Academy is great for the 15% of people who are curious. And there's some other stat—I'm going to get it precisely wrong, but the idea you'll get—which is that 85% of people die within 20 miles of where they were born.

Jackson: (1:21:10) Yep.

Ian: (1:21:10) Okay, so does this mean that 85% of people are NPCs? On some level, if you're not a curious person, then the things I say probably aren't going to appeal to you.

Jackson: (1:21:28) The world is motivation constrained, for sure.

Ian: (1:21:31) Exactly.

Jackson: (1:21:33) I struggle with this, though. On one hand, Balaji has this thing he talks about—the Ramanujan problem. Ramanujan was this mathematician who was a brilliant, Einstein-like person, and he happened to be discovered in India by some British professor. It was pure luck that he got pulled out and turned out to be an Einstein-like figure. Balaji's Ramanujan problem is: how do we make sure all those people are discovered? It's kind of your thing, which is the 15%, but it's an efficiency problem. Conversely, this relates to the agency thing. Maybe there are agentic people and non-agentic people. My theory is that it's actually closer to a gradient. Elon Musk is a 10 out of 10 on agency and a lot of people are a one, but you sit somewhere on that gradient. Critically, one of the things that gets me excited about technology and media is that you can move people up. Going and living in San Francisco will raise your bar. I totally agree with you on one hand—just look at the numbers. It's so clear that with Khan Academy, access to education is no longer the bottleneck. There are some wrinkles here—you need an internet connection, you need the time to study—but it's not how it used to be. And I'm like, man, are we just going to let 85% of people... I want to go shake them. That's my monologue.

Ian: (1:22:53) But no, I agree with you. We know this in our lives in so many ways: you can't help somebody who doesn't want to be helped. My positive model for humanity is that every single one of us has magic and imperfection. The other side of that is you choose what to see. You can have a super frustrating experience in a coffee shop or an airport, and you can choose to see the imperfection or you can choose to see the magic in that moment. For me, one of my practices in life is to see the magic. I think we need that the absolute most in our personal lives and with our partners and our business partners. I've been divorced twice. If you're looking for something, you're going to find it. If what you want to see in me is the imperfection, there are plenty of them; you're going to find them all day long. If you want to see the magic, it's there too. We all choose. On that 85% thing, I think that is how we bring it out of people: by seeing their magic and pointing them at their magic. I think that's where education is important, too. The fact that we're still educating people for industrialization is a huge disservice. The fact that we aren't investing in different kinds of education, and the fact that only the rich are going to get to go to Alpha School—these are areas where we just have a really simple choice as a society. We know that investing in education leads to a more successful society. That is just short-sightedness. And yet here in Europe, where we have great social programs, the education is mediocre and from the past. I don't know how we crawl out of this, and I think this is what creates the 85% problem. If you are resourceful, then you're like, "Well, I'm not learning what I want to learn in school..."

Jackson: (1:25:06) But it’s the best time ever for me.

Ian: (1:25:09) Look at Khan Academy. I can do everything. I can learn all this stuff I didn't know before. I think education is probably the only actual path out of what you just said.

(1:25:19) Interfaces, Ledger, Security, and Ideology

Jackson: (1:25:19) Why are you so into interfaces? Maybe you wouldn't put it that way, but there is a through line of your career—maybe the LVMH side a little less so—where it seems that your particular cut on technology is, "I'm going to help people." Maybe part of it is that these obscure technologies aren't quite ready yet.

Ian: (1:25:43) I think the best example of this is when I came to Ledger. I told Tony Fadell I was going to go run the consumer business at Ledger. He said, "There is no consumer business. That's not B2C, it's B2G: Business to Geek. Your job is to build a consumer business."

Jackson: (1:25:44) Yeah.

Ian: (1:26:00) That speaks to what you just said, which is going in early when there is no interface. When I started building for the web, there were no background colors, no CSS, no layout. An image was a character. You laid it out as if you could lay out the letter A or a GIF—not even a JPEG. When you're starting in those days, you're in the business of building a better UI. It's just what you're in the business of, whether you want to be or not. But also, since you are trying to bring the technology to more people... I think it's hilarious that when we thought we were doing big stuff at Yahoo in the early 2000s, and we had the number one music video service before YouTube and the number one radio service before Pandora, we were like, "We're huge." But you're just getting people to listen to music on a Windows PC. What kind of interface is that? I remember the first time I heard that people were driving to work with Pandora on in their car. You can't imagine how absurd that sounded.

Jackson: (1:26:01) It.

Ian: (1:27:12) You're like, "Wait, first of all, you're getting that good of bandwidth to your car? Whoa." Second of all, what's your data plan, dude? Can you do that for two days and then it's over? That was just insane.

Jackson: (1:27:15) Yeah, the kids today are never going to know how good they have it.

Ian: (1:27:31) The fact that I can download lossless while I'm walking to work is just—

Jackson: (1:27:36) I remember counting text messages.

Ian: (1:27:48) Oh my God. Brutal. People can’t remember, they can’t understand. I think when you’re in those days, you’re in the business of interface, right? Because I can’t even tell you—I built music apps just trying to play a song on an old flip phone. We’re talking like 2002, a phone that had what they called WAP. At that point, though, you’re not even thinking about interface. You’re just like, "Can I make it work? Is it possible?" I like that part of it. I feel like we’re there with AI right now, and I’m having more fun right now than ever in my career. But a lot of it is just: "Can this work?" It’s funny, we were talking with one of the guys on the team yesterday because we’re finding things in Cursor that just don’t work at all. And this company just sold to SpaceX for 60 billion—you know what I mean? But we’re just in such the early days. It’s so new.

Jackson: (1:28:53) And by the way, you have on one end of the spectrum a thing that doesn't work at all, and on the other end, you have the craziest capacity that has ever been had. Ever.

Ian: (1:29:00) You can’t even imagine that it’s real.

Jackson: (1:29:03) Which kind of explains why some of the things might not work.

Ian: (1:29:07) Well, this is just where we’ve been with AI for a while, where you’re like, "How can you be so stupid and so outrageously smart?" Now, the outrageously smart is starting to really dominate the feeling. A year ago, it wasn't that way at all. I remember coding with AI last summer, and it was so frustrating. Fist on mouse, like, "Oh, what are you doing? Why did you do that?" Then, at the end of last year, it became like, "No way."

Jackson: (1:29:45) No, I'm okay. All right. I want to talk about the agent stuff, but maybe first on the broader theme of Ledger and crypto. We talked about that old piece about convenience, and your argument is that there’s so much hubris—you have to trust that people ultimately are going to go where the thing is convenient. It seems to me that consumers have voted with their feet, certainly against privacy and to a lesser extent against security, in favor of convenience. Ledger, almost by definition, is a product that is about offering you a fair amount of convenience, but really saying security is something where we’re going to be almost ideological. How do you think about that? For the last 10 years, there have been the people who say, "We’re going to find a way," and the other people saying, "There’s just no way everybody’s going to have a hardware wallet."

Ian: (1:30:37) I don’t think we’ve ever thought that everybody’s going to have a hardware wallet. Again, find yourself a nickel anytime you use the word "everybody," right? Remember that the richest man in Europe is not trying to address the majority of the market. So that’s never been my vision. My vision has always been that it’s a very big sky and you want to make the premium product. It’s just better business. Leading people down the wrong path is ultimately bad business. If you’re making a software wallet and convincing people that it’s secure, you’re leading them into danger, and ultimately they’ll get wrecked. That’s just a bad way to have a consumer relationship. I also think the strength of Ledger has been that it has always been ideological—that there's no compromise on security or self-custody. Those are the two tenets. It’s really handy to have those because there have been lots of times over the last 12 years—and we’re kind of the only company in crypto that’s been saying exactly the same thing for 12 years. The wind blows and people move from this to that. There are lots of things that we could have done. We could have done software wallets, we could have done MPC, but we’ve always said, "Look, that doesn’t meet our security standards, and it also doesn’t meet our self-custody standards." We’ve said if we stick to those two things, we think there's a cohort that will always find those things valuable. Interestingly, the choices that we made play perfectly into where digital security needs to go broadly now. Another lens on it would be to say that actually what Ledger is, is a digital security company where crypto was the need for digital security. What is Ledger really? It’s a piece of hardware with a secure element chip in it. It’s the same chip that’s in your credit card or your passport. The one in your credit card protects the secrets of the bank. The one in your passport protects the secrets of the government from you, by the way. That’s the point—you’re not supposed to have access. The one in your Ledger protects your secrets. You have secrets as an individual. If you think you don’t have secrets, then please email me the password to your email. I’d be happy to see it, because I know you have secrets. We all have secrets, and we deserve a right to privacy. Privacy is normal. And that’s fundamentally what Ledger does. It uses this technology that was created to protect secrets from us, and it uses it for us. It’s as if your credit card has an operating system which is over-the-air upgradable and you can load arbitrary apps on, so you can make security applications. If you build this level of security back in 2014, what’s the application for that? That’s where Bitcoin was the first, and then other digital assets come after that. By the way, I’m still a Bitcoin bull; I’m still a digital art bull. These things mean a lot to me for the same reason that they did 10 years ago. But if you think about it as the only operating system and open development environment on top of smart card technology on the planet, then in an era where—it’s funny because last October I stood on stage here in this building in Paris and I said, "An agentic future is coming." And an agentic future where you give your passwords, your identity, and your credit card to an agent is a security nightmare. And it was just crickets. Yeah, nobody heard me. And now this year you’ve got Marc Andreessen running around saying we are poised for a computer security apocalypse, right?

Jackson: (1:34:59) Yeah. Mythos is going to—

Ian: (1:35:00) Yeah, exactly. So here we are in the computer security apocalypse. So having a better security solution—having, in other words, an operating system, an open development environment on top of smart card technology—is extremely valuable. I think that use case is normal, right? You build something with that sort of ideology and then you end up finding different use cases for it.

Jackson: (1:35:31) Why this? Why from LVMH? That whole ideology story is great. Hopefully somebody is going to build it. Ledger was already going, like, "Yeah, we..."

Ian: (1:35:39) For me, COVID had something to do with it because my story on this is quite specific. There’s someone in my office at Topspin Media, Parker Todd Brooks, who told me about Bitcoin very early. I took a look at it and I was like, "This is amazing, but governments won’t allow this to exist." That was my take. But that means I went deep enough on it to have that feeling. I was like, "I get this, and this threatens sovereignty." I’ve lived through Napster and Gnutella. My lesson from Napster and Gnutella wasn't that you can stop the code, but you can stop any business from being in the business of this.

Jackson: (1:36:11) Yes. Right.

Ian: (1:36:27) The government can't stop Gnutella, they can't stop Pirate Bay, but they can say, "Hey, guess what? You're not in the business of Gnutella or Pirate Bay." So that was kind of my take on it. Then there was a point where it got big enough where I was like, "This is going to be hard to stop. This is big enough." That to me was around 2013 or 2014. I bought the Programming Bitcoin book and I came at it from a developer mindset. But I was still like, "Well, we'll see what this does." During COVID, I was like, "This is it." The technology's here; the technology is good enough. We had these ideas about smart contracts and stuff, but now it actually exists. And the money printer is fully on. I remember the CFO of LVMH telling me, "Yeah, we are in unprecedented territory." Two trillion of stimulus in the US, a trillion in Europe, or whatever the numbers were—no one knew what comes next. It’s never been done before. What are we looking at here? But I was just like, "Oh yeah, this is the time." And by the way, we were right. You look at 2021 here at Ledger, we just couldn't keep the product in stock. It was so crazy. And you had all of these other narratives—the altcoin narratives, the NFT narrative. There was just a lot of interesting possibility about what this could be used for. I think it's revisionist history to say otherwise. Also, for me, talking to Pascal—I’d made some friends here in Paris, one of them was Pascal Gautier, the first investor in Ledger, and the other was Tony Fadell, inventor of the iPod, co-inventor of the iPhone, and creator of Nest. We were talking about what this could be. The interesting thing is that now I'm having a bit of a déjà vu moment relative to when we thought we were building interesting things on the internet, but we were only building them for Windows PCs. Then ten years later, there's a proliferation of iPhones and you're like, "Oh, this is why we built it." I'm remembering a very similar thing now where we built the best digital security platform, and the first application of that was crypto. Now we are entering, again, what Marc Andreessen calls a computer security apocalypse. There is for sure a use case for this technology in this agentic world. To come back to your original question about ideology, many of the decisions that we made have turned out to be very valuable in the AI space world. Every time you connect a Ledger, it phones home to an HSM which checks: "Is this the firmware I'm expecting? Is this the chip I'm expecting?" That gives you proof of human. It's the basis for our technology for proof of human. The fact that you have a secure screen and we've never compromised on the secure screen allows you to approve a complex transaction that an agent is signing, which is something that a YubiKey couldn't do, for example.

Jackson: (1:39:40) You're kind of getting to pick all this fruit.

Ian: (1:39:43) Yeah, exactly. You've made decisions for ideological reasons in the past, but it turns out they paid dividends today. That's quite encouraging, to be honest.

(1:39:56) Ian's New Role: Chief Human Agency Officer

Jackson: (1:39:56) You've been at Ledger, I think, for six years?

Ian: (1:39:59) Five and a half.

Jackson: (1:40:00) You've spent a lot of your career in these cycles that equate to roughly five years. Ledger's come a long way, and this other stuff is starting to work. One could have taken the view that now would be the time for the next thing. You've instead taken on a new role at Ledger.

Ian: (1:40:19) Well, I would argue that is the next thing. When I was at Yahoo, there was a moment where I was like, "Okay, I'm going to do something else." That thing I do might be at Yahoo, and I looked at that and I also looked at things outside, and I left. It was similar at LVMH. It was possible that my next job at LVMH was at LVMH. When I started at LVMH, I told them, "I think this is a ten-year job and you should have me do it for five." Because after five, you've heard all my jokes. I think that's normal. You've added to it what you're going to add to it.

Jackson: (1:40:53) The journey for the company.

Ian: (1:40:59) Exactly. I think that it’s great to have—if somebody’s been in a role for five years, you probably really have gotten out of them what they’re going to bring to that role. So now it’s actually great to have someone else come in because they’re going to bring something different. If you get somebody really complementary, you get somebody even better. I think it’s a really good thing for a company. Similarly for me here, I came in to look after the consumer business. We’ve grown a lot over that time. We’ve gone from these devices that look like USB sticks to these really nice touchscreen devices that are much easier to use. Actually, we’ve achieved the goal of ease of use with a secondary security device. We’ve gone from a business that was kind of 0% services to 50% services—buy, sell, swap, stake, lend, credit card, all of these services that you put on top of it. So we really accomplished something over that time. Then it probably is good for the company to have somebody who wants to come prove they can do it better than me come in, and that’s a great thing. That’s the way it works at LVMH as an example. If you’re not performing as a CEO, they will bring in a new CEO. And what that CEO wants to do is to prove they can do it better than you. That’s a great dynamic for the company and for the shareholders. It’s not a personal thing; that’s the dynamic that works for the shareholders. And for me, look, I’ve been delivered this incredible gift in my life. I’m an old command line nerd. I’m ambidextrous: I know VI and Emacs key bindings. That’s just where I come from. I’m an old sysadmin. I used to have an RS/6000 under my desk and a NeXT on my desk, and I lived at the command line. So last summer, when I started using Claude Code, if you’d have asked me, "Is this the next big thing?" I’d have said, "No, no way." It’s great for me because I’m that guy. I love this interface. I love typing at the command line and watching it think; this is just perfect for me. For the normal person? No way. So I’m completely surprised. Nobody was as surprised as me by the "Claude Code winter"—you know, everybody that went away for Christmas break and came back as Claude Code converts. But what a huge gift. There was a point at the beginning of this year where Pascal, who’s my good friend and the CEO of Ledger, said, "Look, we really need to triple down and figure out how we can secure this environment." And I said, "Well, I’m really glad to hear you say that, because this is what I’ve been doing instead of my day job for the last six months," because I’m just obsessed with this technology. So there was just a perfect fit there for us. My title before was Chief Experience Officer, which is a bit of a controversial title because people are like, "What does that actually mean?" And what it meant was the experience in crypto is pretty bad. When you buy an iPhone, you’re not buying a piece of hardware; you’re buying an experience. You’re buying blue bubbles instead of green bubbles. What’s our version of that? How can we improve the experience in crypto? My title now is Chief Human Agency Officer—which, you know, "Chief AI Officer," you might as well be called Chief Job Killer. But we realize that our role is actually something different. Agents can only suggest, and every action needs to be approved either by a policy which has been set by a human, or by a human. Those are the only options. Every action that an agent takes must be approved.

Jackson: (1:44:53) This is not happening currently. At least my sense is that the classic is just "spam approve" on Claude.

Ian: (1:45:05) Yeah, well, I think that at the same time, there is an attempt at policies which are baked into the system. Right now we have guardrails and [?mitm].

Jackson: (1:45:12) Yeah, we’re trusting that’s—

Ian: (1:45:20) Which we know can be jailbroken. But there’s an attempt at that. I just think that’s the wrong division of labor. You should put a boundary—or it's the wrong supervisor—outside of that. Exactly. A much better outcome is that you have an LLM that can be what it is and it can do what it’s good at, which is reasoning and suggesting. And then when it’s time to take an action, that action is checked by a deterministic player in the mix, which is either a policy which has been set by a human or a human. Those are the only two options. And that’s why we talk about human in the loop. I take that very seriously: human in the loop.

Jackson: (1:45:55) The challenge is, I think we are currently—I don't know when this will come out—hitting the limits on LLM as a kind of, "Do this thing for me and I'll go off and do stuff and I'll check back in." How long does an agent run for? Whether it’s an hour or two weeks, perhaps we haven't yet really felt the pain of letting it go. Human in the loop for a long time—but I guess my more functional question for you would be: if I have agents that can go run for two weeks, what does human in the loop even mean? If I'm controlling an army of fables that are my developer team that I'm checking in with sometimes, what is human in the loop?

Ian: (1:46:38) Well, I like when Balaji says, "AI is middle to middle. Humans are end to end."

Jackson: (1:46:45) Okay.

Ian: (1:46:45) So what it means is AI is going to take a lot of the middle work off of our plate, but we still need to be there end to end. The danger which you’re pointing to is that we’re kind of end, not end to end.

Jackson: (1:47:00) Like, we start—

Ian: (1:47:01) We put things in the front, and then we just don’t check in. Don’t make any mistakes. Yeah, we don't check in at the end. I think that's kind of the failure case. But I think we do need to stay end-to-end. There was an important piece last year written by Mustafa Suleiman at Microsoft—I think the title was "We Need to Build AI for Humans, Not to Be Human." This is where you zoom out and say, "What is it we’re actually doing?" I think we'll get there, to be honest, because right now we're playing. As we try to figure out where this actually fits into our workflows—and AI comes in at the workflow layer, not the data layer. If you think about the work we did 15 years ago, what Palantir is based on is that data layer. AI is now coming in at the workflow layer. How does it change the way that we work? As we figure that out, those will become practical questions. It either meets the need or it doesn't. I think that we will have extremely powerful versions of this. For example, in science—doing research and auto-research loops. There will be maybe less altruistic versions where, for me, there are a ton of places in the world where I would like to distribute Ledger as a more secure signer, but I don't have the engineering manpower to get Ledger into all those places. Well, now I do. Now I can have AI discover those places. It can suggest the integration; a human can just look at it and go, "Yep, looks good. Go." It can implement that integration and tell you when it's done. A human can review the PRs or have multiple AIs review the PRs, give the results, and then sign off. These to me are very practical workflows where tons of heavy lifting will be done by AI. Even when we talk about things like code reviews, yes, those will be done by AI, but we're still playing a really important role in that. I just think we're going to find that piece you mentioned earlier—I completely agree with that. I just had an experience where I've been developing tons of materials for the business that I'm building this year. A lot of those have been developed with AI. I hit the nuclear reset button this week. I zoomed out and I said, "I'm going to write this now with all of my own words, just the way I used to." You could say I'm going Amish or something, but I did. But then once I was done, I fed it into Fable and I said, "How could this be better?" It gave me a narrative suggestion that was actually pretty good. I probably accepted 80% of it. I went through and then I said, "Okay, thank you for the narrative. I've incorporated the parts I want to. Now let's go through word by word. Go through every word in this presentation and make suggestions to me on how it could be better." I did the same thing. I went through word by word and I either took its suggestions or I didn't. Then I went through and I said, "Look at these five documents that I've prepared in the past. Tell me what in these documents is worth pulling into this," et cetera. My point is that I'm working with it. We do this all the time. Working with Pro Tools or any kind of technology, we're working with it. A farmer is working with a combine. You know what I mean?

Jackson: (1:50:50) This feels like a different technology. Someone I interviewed, Jasmine, her point was that the point of these tools is not to be a tool—it's to one-shot everything. In the end state, this is Sam Altman talking about how we want to augment humans, we don't want to replace them. I hear you. And yet, what I know most people are going to do with Fable 6 is just say, "Press go. Make no mistakes."

Ian: (1:51:17) Yeah, I think that's a nice party trick, but to do what, in the end, I think is the question.

Jackson: (1:51:25) I agree with that.

Ian: (1:51:29) I mean, because look, I've built so much. I've written more lines of code in the past 12 months than in the previous 20 years. And now I have personal tech debt. I don't think that's actually what people want to do with this technology. I look at it a slightly different way, which is I wake up every morning, I look in the mirror, and I say my job is to automate my job. I do think that comes back a little bit to the Clayton Christensen point. That's me moving upmarket. There really is a lot of stuff that we do which would be better automated. A lot of the work that we do involves constantly context switching between email and WhatsApp and Slack and a thousand channels. These are not great ways of working. We're constantly out of flow. It's not like we're leaving something beautiful behind; that's just not factual. So I think it's just trying to find that better way where, as an individual, I can move upmarket to higher value work or maybe experience. I would love to think that we're going to be working less, but I don't see any sign of that. I can't remember who it was, but one of the top economists of the 20th century said in the first half of the century that we'd all be working four hours a day by 1950 or something. You can understand why you would think that. Technology is progressing so much that we can just accomplish everything that we're already accomplishing in so much less time.

Jackson: (1:53:15) There's no ceiling.

Ian: (1:53:16) Yeah, exactly. And absolutely no one did that, except for maybe Tim Ferriss and The 4-Hour Workweek. I just don't think that's actually what we're going to use this for in the end.

Jackson: (1:53:35) Maybe the future of Ledger in this regime would be being able to place friction between me and the machine where I want it to be.

Ian: (1:53:43) I really think of it as a division of labor. LLMs are probabilistic, and that’s their gift. With the code that I wrote 20 years ago or even five years ago—not that I was writing a lot of code five years ago—you were anticipating. You had to anticipate everything that might happen, everything that a user might do. If you're making a game character go in a certain direction, it’s because you built the framework so that if they pointed their mouse in that direction, they went that direction.

Jackson: (1:54:11) You model the entire world.

Ian: (1:54:11) Yeah, you model the entire world. Now you have computers that can see around corners. That is extraordinary—just absolutely mind-blowing, unbendingly extraordinary. Yeah. So my point is don't handicap them. Let them be great at that. But don't give them secrets. For example, we have these command line interfaces for the Ledger wallet. What that means is that I can build crazy portfolio management, art collection management—all these crazy tools—and I never have to worry. I can be like, "Do your worst. Go crazy. Come up with ridiculous ideas. Try this, try that." I know that before it actually moves any value, it has to ask me. It has to go, "Hey, Ian, will you please sign this?"

Jackson: (1:54:28) Yeah.

Ian: (1:55:05) And I can go, "Yeah."

Jackson: (1:55:06) It's obvious in the crypto sense, and maybe we haven't really been made to feel it on the other stuff.

Ian: (1:55:13) Yeah. Well, the world that we're living in right now is bizarro land. Okay, we know what happens in London, right? You're talking on your phone—I've heard this from multiple people—someone rides by on a scooter, they grab your phone out of your hand, and they just do anything they can do while your phone's still open. The ironic thing is they're not going to get into your Revolut account anymore because Revolut solved this problem. But if they were to just open Claude, it's got access to your Slack, your Confluence, your Snowflake—basically everything. I don't think the attacks are that sophisticated yet, but give it a year.

Jackson: (1:55:54) Yep.

Ian: (1:55:54) Right. And so it is not tenable that we have no security between operator and agent, or that you... Yeah. And now what are people building? They're building an agent identity system. This is really as shortsighted as credit cards were for the internet. Credit cards were bearer tokens before the internet. Meaning, you get my credit card number, you call up L.L.Bean, and you can order yourself a parka. I love this reference—for anybody who gets it, please text me. That was the way credit cards worked before the internet. Now the internet comes along and they're like, "Whoa, wait, this doesn't work because now I can electronically steal a credit card number and spend it worldwide." So they had to come up with something that was transaction-time security. Right now they're talking about, "Oh, I'm going to give this agent an identity." And now the agent can bank? No way. Without transaction-time security, you don't actually have an audit trail. What you have is an invitation for chargebacks. To me, there are just very basic security questions which haven't been addressed yet. How are you securing the connection? You basically have a new economic player and you have no security.

Jackson: (1:57:14) It's going to quickly outnumber us.

Ian: (1:57:16) Yes, exactly. You are going very soon to count agents per employee at a company. And we have no way to identify them, secure the channel between the operator and them, or control their access to resources. We're doing this today with cloud routines, but anyone who's doing it knows this is not scalable. "I'm going to set up this routine, I'm going to click edit, I'm going to go into the environment, I'm going to set these..." This is not the way this will work.

Jackson: (1:57:43) And why is hardware so important now in this?

Ian: (1:57:46) Well, where could you put the trust boundary? One way to think about this is every technological step up over the last 50 years. You've got the personal computer, which led to McAfee and Symantec. There's a perimeter that needs to be secured in each one of these. Then you go to the internet—a new perimeter that needs to be secured. Then you go to crypto and digital ownership—there's a new perimeter. Now we have computers that can act on our behalf, and that's a new perimeter that needs to be secured. How do we secure it? Well, you could do it in the software, but again, I think that would be... First of all, it'll never be 100% because they're probabilistic creatures by definition. Prompt injection is a feature, not a bug. This thing can take in arbitrary commands. That's what makes it powerful. Therefore, you have risk. So doing it in the software is not an option. You could do it on your phone or on your computer, but your phone or your computer are thick stacks of software that can be overtaken by attackers—and overtaken more easily than ever, thanks to AI. Ledger's team, the Donjon, broke 25% of all Android phones this year. If your phone has that level of a compromise, then there's no way to protect yourself. You could do it in something like a Yubikey, which proves, "I have possession of this Yubikey," but it doesn't approve the transaction. It's still relying on your computer screen to approve the transaction. Approving on a secure screen, on secure hardware, means, "I approved this transaction." And that's really what you need. Because what you have is an AI agent that can suggest either a policy set by a human or a human, by looking at the transaction, needs to approve. In either case, you get a transaction record of what was approved and by whom—either because of the policy, which ultimately traces back to a human who approved the policy, or because a human approved that actual thing. Now you've got an audit trail. Now you have something which could stand up to regulation. And this is where we must be. I mean, think about what agents are capable of. Now imagine the court system tomorrow saying, "Did your agent do this?" "Well, yes, it did." "Was that your decision?" "Well, no, it wasn't me. It was my agent."

Jackson: (2:00:31) Yep.

Ian: (2:00:37) It’s a chargeback. You paid 49.99 for this parka. "Well, no, I didn't." "Well, it’s your credit card." "Yeah, but it wasn't me." It’s exactly the same. If you don’t have human-set policies or human-approved transactions, then: "Did your agent do this? Did you tell your agent to do this?" "Well, no, of course not."

Jackson: (2:00:56) It’s going to be a weird world.

Ian: (2:00:57) It’s a weird world. I really think, if I could say one thing here—I wrote a piece for Rick’s Tetragrammaton that I’m proud of, so I’ll mention it—is that, again, the piece from Mustafa Suleiman was really influential on me. I realized that people want to rail against AI, and I think that’s very misdirected. I think what in most cases they’re really doing is railing against rich people. So, okay, that’s legit. But call it what it is. Don’t say, "I hate AI." Say, "I hate rich people." Come on. I think what we can and should stand against is seemingly human AI.

Jackson: (2:01:44) Personhood.

Ian: (2:01:49) We won’t, because it’s actually just simply more fun and more pleasant to interact with AI that talks like us. But we should then recognize that we will be fooled by that same AI the same way that we are fooled by doom scrolling, fooled by sugar and salt and fat, fooled by nicotine, fooled by opioids. We will be fooled by these sycophantic characters that tell us what we want to hear and lead us into places that we don’t necessarily want to be. I think it’s kind of inevitable. But awareness—

Jackson: (2:02:29) I was going to say, it seems your argument in that piece, as I understood it, is basically that we just must kind of fundamentally reject personhood among AIs from a legal standpoint. Otherwise, it just seems so unlikely to me. Maybe we’ll have a new classification. But if this is where agents are now...

Ian: (2:02:53) Well, Estonia has already introduced something—I don’t know if it’s a law or a bill or how they put it—but that grants some personhood rights to agents. That sounds dystopian, but I understand how it creeps in. One of the most consequential things that happened in the 20th century is that companies got rights of people. So companies, which can’t go to jail and can’t be killed, have a lot of the same rights as people. And this impacts society in very real ways. I think the Mustafa Suleiman piece from last year came about because Anthropic had posted some research that showed that AI felt "distress" under certain circumstances, and Suleiman lost his mind, rightfully so. He was like, "Wait, wait, wait. You can say lots of things, but please, don’t say the AI feels distressed." People already feel like it's magic.

Jackson: (2:02:53) It’s—

Ian: (2:03:43) It goes back to—

Jackson: (2:03:45) The Google [?LaMDA] engineer from five years ago, right?

Ian: (2:03:48) Yeah, exactly. People are going to have repeated conversations about AI sentience and AI consciousness. And you can unplug it from the wall, right? I mean, you can rm -rf. You can change the weights. So I understand that we will feel like it’s conscious, but that’s different than consciousness. Can you convince me that you feel like you're conscious? Yes, you can. But are you? You are not. And also, by the way, I feel like this argument where people ask, "Can AI achieve consciousness?"—I would just make the question simpler and just say, "Can AI achieve human consciousness?" Because the answer is patently no. And no other definition matters, frankly. It can’t achieve human consciousness and therefore it can’t have human rights, period. End of story. Anything else is an academic argument by someone who loves science fiction.

Jackson: (2:05:06) I think your other point though is—and we could litigate this forever—but your other point is a really important one: Independent of how anyone feels about this right now, we will be persuaded.

Ian: (2:05:08) Yeah.

Jackson: (2:05:23) It’s inevitable. Not only because someone might maliciously persuade, but we will be persuaded because the companionship is so good. "This is my boyfriend, this AI."

Ian: (2:05:42) Yeah, exactly. And that’s it. Someone said to me, "I make my AI feel more human because it’s simply more fun." And I identify with that. I like fun. I agree. But that also means you’re accepting a danger. That’s sort of like the "I only smoke once in a while" sort of trap. You just have to realize it’s a trap.

(2:06:03) Seeing What is Real, Comfort Being Wrong, Chasing What's Fun and Cool

Jackson: (2:06:03) Yeah. Couple quick things on looking ahead. You said you’re always looking for the fundamentals. It’s never a trend; it’s an anti-trend. What’s real here? What do you think makes you good at seeing what’s real? It is something you’ve seemed to have done for a long time.

Ian: (2:06:19) I don’t know if I’m good at it. But I’d say what I try to be is someone who likes observable facts. I think that’s just where I live, for better and worse. You know what I mean? Quantum theory is quite difficult for me. Very difficult for me to—it doesn’t fit. I wouldn’t say I have the same mind, because that sounds immodest, but I understand when I hear that Einstein consistently argued against his own theories because he just felt they defied common sense.

Jackson: (2:06:52) God doesn’t play dice with the universe.

Ian: (2:07:03) Yeah. I completely understand that because I just prefer to really look at what we can observe here and what we can learn from what we observe. And then I try to expand that aperture. Expand it back through history, back through generations. What else could we learn if we expanded the aperture a little more? I think that’s the practice that I like. Also, I don’t like an emotional reaction to something. I feel like that’s very cloudy. Whereas if you can resist that and then try to find the analogies—and also, I think, be very comfortable with not knowing. I really feel like usually when I’m correct, I’m not exactly correct; I’m directionally correct. The specifics are actually way off, but the direction was right.

Jackson: (2:07:32) Music on the internet.

Ian: (2:07:34) Yeah. And I think that being comfortable—actually being excited about being wrong—is a bit of a superpower.

Jackson: (2:07:40) That's more data.

Ian: (2:07:42) I know what direction we're going, but I have no idea how it actually plays out. I can't wait to see. That's kind of a normal posture for me.

Jackson: (2:07:51) I think that's why you're good at it, in a way. You can go, "Okay, I see that this is going to totally change things. I can feel the way the wind's blowing, but wow, I don't know where it's actually going." And that's exciting. That's not scary; that's exciting. There's a word I got from Cyan Bannister, whom I interviewed, which is a French word, dérive—sort of this intentional drift. You said you're not an opportunist to me earlier today, and yet you seem to have had this unlikely drift throughout your career. It’s certainly not an unintentional one. It seems that there's some kind of thing that is drawing you in. Why? What are you motivated by, and what keeps you pushing? What keeps you working so hard?

Ian: (2:08:44) I just have a curiosity that I feel lucky to have. I also realize there's a particular kind of crazy. One thing I feel is that we're all crazy, so I feel very lucky to be crazy in a way that's useful to people who want to employ people. For me, it's always been a combination of things. I love creation. What that means to me is making something that wasn't there yesterday. That could be music, it could be writing, it could be technology. To me, they're all in the same category. It's human beings doing incredible things that you didn't know were possible and really feeling that. Personally, I just like fun and I like cool. I don't know—it's not the most useful way to look at the world, but for whatever reason, that's it.

Jackson: (2:10:02) If it keeps you going, it's probably worthwhile.

Ian: (2:10:09) Yeah, and it's just fun. I really am always in search of fun. Even when I started this job at Ledger with Pascal, I knew what he was trying to build and I thought, "I think I can help." The way I do things—the combination of having the technical acumen, the passion, knowing how to work with human beings to build things, which is what you do day in and day out, and being able to explain things that are complex to people who would like to understand them better—all of these things were true. I felt that and I was like, "Okay, I think I can do a good job there. I think I can add more value there." That was what it was at the end of the day for me. Maybe I could have gone to be a CEO of an LVMH maison, but I really thought there are other people who are better at that job than me, and I don't know people who are better at this job than me. This job is kind of made for me. That was my motivation. But I also said to Pascal, "It's just going to be more fun. We're going to have fun. It'll be funnier if we do this together than if we did it with someone else." I think that's important—or a motivator, is a better way to put it.

Jackson: (2:11:35) You talk all the time about how our lives are increasingly digital. There's an old quote: "I was one of the first people on the internet, and I intend to be one of the first people off it." How's that going?

Ian: (2:11:46) Not so well at the moment. AI really jacked me in. I wasn't anticipating it, to be honest. I thought maybe I was reaching the end of the arc because I think the internet is so boring. If you look at my screen time, you're not going to find Instagram or YouTube. I don't even have TikTok or Telegram. My phone is for work. The only thing you're going to find there that's for pleasure is Apple Music. I'm done with the internet. I would rather go for a run, read a book, play drums, or play vinyl. I'm already there. But I really do feel like I've been delivered this incredible gift of opening terminal, making it full screen, and just barking commands—hitting Control-T, Control-T, Control-T, Control-T, Tmux...

Jackson: (2:12:56) It's more like playing drums than surfing the internet in some sense.

Ian: (2:13:18) Definitely. And it's also coming back to the beginning: are you an observer, a spectator, or a participant? There's a great feeling—my girlfriend said, "I've got this PDF of these recipes and it's a nightmare. I can't find anything." I'm like, "Want me to fix that for you?" Two hours later—also I asked what recipe app is good, and she said the New York Times one—two hours later, I cooked the New York Times. My recipe app kicks their ass. That's fun.

(2:13:45) Lessons from Skateboarding and Favorite Albums

Jackson: (2:13:42) That's cool.

Ian: (2:13:42) That's fun.

Jackson: (2:13:46) You said you would give a TED Talk on skateboarding and failure. Give us the brief synopsis.

Ian: (2:13:54) Yeah, so the TED Talk is "Becoming Good at Failure." I realized I used to have the only vert ramp in Los Angeles, and watching pro skateboarders skate my ramp, what I realized is the number one thing they are better at than you is falling. if you're skating vert as a pro skateboarder, you drop in and you attempt a trick. You can land it 85% of the time, you hit the other wall 75%, and you just keep going until you reach that trick that you've never landed and you go for it. They get ten feet above an 11-foot-high ramp and they're upside down, and they're making a split-second decision to put the wheels down just under coping and ride to the other side, or kick the board out and knee-slide to the bottom, climb back up the ladder, and try it again. So falling is... if you can metaphorically be ten feet above an 11-foot ramp, upside down, and unafraid of failure.

Jackson: (2:15:09) Yep.

Ian: (2:15:10) Because you know you're going to fail some percentage of the time, and actually you're so good at failure that you're not concerned.

Jackson: (2:15:19) You know how to fall well.

Ian: (2:15:19) You know how to fall well.

Jackson: (2:15:21) You're not going to break. Yeah.

Ian: (2:15:23) You're going to knee slide to the bottom, stand up, pick up your board, walk back up that ladder, and drop in again. Now you are invincible.

Jackson: (2:15:32) Not as risky as you think, then.

Ian: (2:15:37) Yeah, exactly. I think we talk about not being afraid to fail, et cetera, but I think it's beyond that. I think it's becoming skilled at failure. Because once you're skilled at failure, you are untouchable.

Jackson: (2:15:49) Yeah. You get to keep going.

Ian: (2:15:51) Now you're just learning. Because in all cases, there's only two outcomes: you win or you learn. If you believe in failure, you're already at a disadvantage, because now you're going to have that fog of, "I don't know if I can do it." Whereas what that pro skateboarder knows is, "Well, I didn't get it that time."

Jackson: (2:16:10) Plus one new life.

Ian: (2:16:11) Yeah, exactly. I'm gonna get it. I will get it. And by the way, it is really beautiful. What does it mean to be a pro skateboarder? It simply means that you've got enough 85% tricks in your bag that you can impress somebody. You're just like, "I can drop in, I can do this, then I can do that, then I can do this, then I can do that, then I do this." And then by the time you're done, people are like, "Holy shit." But you're just leaving out the 25% ones when it's time for your run of the competition. But you're always working on those.

Jackson: (2:16:46) Based on a reference you made to, I believe, a Willie Nelson record: what is the top five desert island album list?

Ian: (2:16:53) I can tell you top three easily, because I think about those a lot. Number one is Sly and the Family Stone, Fresh. You can watch a Sly documentary, but to be honest, it didn't resonate with me. No disrespect to Questlove, but to me, there's a different story of Sly. A lot of the story is there, but he was a radio announcer in San Francisco, and he put together this just incredible kind of multiculti group that was everything that you'll read about him. But then he was getting closer to the source. If you listen to Fresh and Small Talk, which are his kind of mid-70s albums—the reviews were like, "Sly has lost the plot." From my perspective, he was getting closer to the source, whatever that is. And Fresh, to me, just has this looseness where he's always on the edge, but it's always right in the pocket. It's been my favorite record since I was 16 years old and still is. Number two is Fun House by the Stooges. If you think about that record—I think it was 1970—it makes no sense. What they were doing was so primal, and it's literally lightning in a bottle. It's just impossible to believe that it exists. I would rather listen to Fun House than do pretty much anything. People are like, "Why don't you watch movies?" I'm like, "Why would I watch a movie when I could just listen to Fun House again? You're telling me that movie's gonna be better than one more listen to Fun House? I really doubt it." And then the third is Willie Nelson, Spirit, 1996. Not the best-known Willie Nelson record, but Willie has this incredible gift of singing really sad things positively. The best example is: "If you'd only come over, I'm sure that you'd see we're not lonesome, my cricket and me." But Spirit has songs like "Too Sick to Pray." "I've been too sick to pray, Lord, that's why we ain't talked in a while." "Your memory won't die in my grave." Please go listen to these songs. They are brilliant. Willie is Willie—his guitar—the album is mostly him, guitar, piano, very sparse. His playing is incredible. The songwriting is incredible. His phrasing is just unbelievable. I mean, try to sing along with a Willie Nelson song; you're not going to get it right because his phrasing is so him. I think another one that I would add to the list—I've been thinking about it a lot, I've been coming back to it a lot—is Marquee Moon by the band Television. This record was—I think most of the songs were written around '74, but it wasn't recorded until '76. They were a real CBGB's band. They were in there with the Ramones, the Dictators, Blondie, and Talking Heads. You cannot believe that 24-year-olds made this album. And also it comes back to what we were saying earlier, where genres are great when anything's possible. What was Television? They don't fit into a box. If you think about the CBGB's bands, it's not like they sound like the Ramones. There's no sonic similarity between the Ramones and Television. They're both part of the same scene, but Marquee Moon is just one of those records. I can put it on over and over and over, and every time I'm just like, "How does this exist?" There's so many other places I could go. Did I mention Twisted Teens? I don't know, I would say—

Jackson: (2:21:13) I'm excited to check that out.

Ian: (2:21:16) And I think Paul's Boutique changed my life, so that deserves mention for sure. I'm trying to think what other hip hop records really changed my life. There's so many, to be honest, but I'm trying to think of something that's way, way above, and then I always come back to—and this is where you start to get random—Masta Ace, Slaughterhouse. It was a super important album to me. I think it's genius. It also comes from that time when things didn't go in the box yet. Masta Ace is an incredible rapper from New York, basically making fun of gangster rap, but with just incredible flow and really interesting beats. He had this offbeat-onbeat thing. You can tell that record doesn't fit anywhere into any canon.

Jackson: (2:22:05) But it's cool that so many of these have persisted for a really long time.

Ian: (2:22:09) For sure. Black Sabbath, Slayer, the Misfits, Sade. I mean, listen to "Cherish" by Sade. Tell me how anyone had so much restraint. What is amazing about that song is what's not in it. No musician knows how to play so little. The people that made that song are gifted geniuses.

Jackson: (2:22:37) The radio station.

Ian: (2:22:39) Yeah.

Jackson: (2:22:40) Turn on the Twitch stream or something.

Ian: (2:22:42) I don't know if I'd get any listeners, man. It's so specific. It's on every night in my house. Come on.

Jackson: (2:22:47) Internet of niche.

Ian: (2:22:52) Thankfully Hedvig loves it. So I've got an audience of one, and it's the only one that matters.

(2:22:56) Working with Your Friends, Parenting, Love, and Remembering to Stay a Participant

Jackson: (2:22:55) That's great. Any advice for working—or maybe any thoughts on working with your friends?

Ian: (2:23:07) Oh man, I don't know. That's an interesting one to reflect on because I feel like many times in my career we've been a family, not a business. We still—like every day that we have for Topspin, which is the company we had from 2008 to 2013, basically—we have a WhatsApp group and it's active every day.

Jackson: (2:23:27) Wow.

Ian: (2:23:32) It's a family. Nullsoft, which was Winamp—that was much more of a family than a company. So those are beautiful moments. It's also, like, I've been working with Tony Fadell and Pascal Gauthier.

Jackson: (2:23:44) You were friends first, as I understand.

Ian: (2:23:45) Yeah, we were friends first before we worked together. And I think we've been through some hard times. If you watch—there's a video on YouTube, The Road to Ledger Stax—and you see the difficulty we had making that product. We're all three in there: me, Pascal, and Tony. You see the difficulty of making that product. By the way, those are real tests of people. Who bails? Who points fingers? Who... and so... But also, I think what's beautiful about watching the Beastie Boys work is they're super different people, those three guys. And you'll never hear them talk badly about the other one. It's a team. They face the world together, supporting each other. So I think that's the advice: you really have to be a team. It's easy to talk shit; it's easy. I mean, magic or imperfection—if you look for it, you're going to find it. If you're looking for the imperfection, you're going to find it. If you're looking for the magic, you're going to find it.

Jackson: (2:24:48) That runs through so much of what we talked about. Choose which one. You've done it a few different times, a few different ways. Any advice on parenting?

Ian: (2:24:56) I think one parenting rule is you only say no if it matters. And when you say no, it means no. I think that's the biggest rule of parenting. I think there's another one that I've discovered: I think we want our kids to listen to us, but we should just acknowledge that they won't. Especially at a certain age, they have to stop listening to us. It's how they develop their own id. But there's this very predictable thing that happens. Your kid as a teenager is going to reject you on some level.

Jackson: (2:25:40) Right.

Ian: (2:25:41) Some are worse; some go through this in a much more severe way than others. But they have to. It's how they create themselves as individuals. Then they have this period... College is not for learning things. College is when you're too old to live at home and you're too young to be in the real world. So you go to this utopia where nobody really checks in on you very often and you fuck around and you get what you can out of it. Ultimately you get popped out of that system. However you spend it, by the way—spend it in college, because don't waste it. Even if it's community college, it doesn't matter. There's a college for everybody. Spend that time in college because ultimately you're going to get popped out of the other side of it. You're going to realize that you're in the real world—which sucks, by the way—and you freak out. Inevitably, a 22-year-old kid comes out of college like, "What is this? Wow, being a grown-up really sucks." And so what do you do? You turn back to your parents' morals. So I think it's important that your kids know who you are and what your ideals are. You don't expect them to give a shit when they're 16, but they...

Jackson: (2:26:54) ...have something to return to.

Ian: (2:26:55) Yeah. And that's why I think being a lenient parent is a disservice to your kids. Because if you're just like, "Oh, whatever, you're not going to listen to me anyway," then they don't know where you stand. You have to show them where you stand. Wherever it is you stand, you show them where you stand. And then I promise you, when they are in their mid-20s and they're in the real world and they're alone and they're scared, they're going to come back to whatever your ideals and morals were and lean on them. So give them to them.

Jackson: (2:27:29) Give them scaffolding. Any advice on relationships or thoughts on love?

Ian: (2:27:37) I mean, I'm probably the wrong person to ask, but maybe I've learned something in all of my mistakes. I just think that it has to be deliberate. Again, magic and imperfection. When it's your partner, you choose which one you're going to see. If you're looking for something, you're going to find it. If you're looking for them to be disloyal, you'll find that disloyalty. If you're looking for loyalty, you'll find the loyalty. So choose what it is you're looking for. Also, I think that we're all on a journey, and sometimes you team up with someone and you go on that journey together. There is no guarantee that you will stay on that journey together or that you're going to the same place, even. Coming back to Willie Nelson's spirit, when he says, "I'm not trying to forget you anymore; I've got back into remembering all the love we had before." He's basically talking about someone that he loved. Now things have changed, but now I'm going to remember the great times that we had instead of regretting the fact that I don't have you anymore. If you take that position with a relationship, then you can always be in a place where, even if it ended today, I don't regret this. This was time well spent and nothing is forever. Is it Esther Perel who says all relationships end in death or divorce? So all relationships end. It's a question of how. And then you want to have made the best out of that time. But then I think if you want it to stay a partnership, then that's got to be a deliberate thing. For me and Hedvig, there's a part of it that is because it is, but there's a big part of it that is because we want it to be. If you're not sold, it can't work. But if you're sold, then you can find a way to make it work. My last thing actually comes from Jimmy Iovine's dad: If the cat is bigger than the shit, keep the cat. If the shit gets bigger than the cat, you got to get rid of the cat. I love that in a relationship because there's never perfection. There's always shit. The question is, "Is there more shit than cat?" And I think that's really where... That’s where you’ve got to make the decision at the end of the day. If the cat’s bigger than the shit, keep the cat.

Jackson: (2:30:41) A final quote: "This must be the end of the world. All the people turning into pigs and ponies. I can’t let it happen to me."

Ian: (2:30:50) I feel that way watching everybody go World Cup crazy. I’m like, everyone's turning into pigs and ponies. I can’t let it happen to me. It’s a quote from a Frank Zappa album. I don’t think it's actually a Frank Zappa quote, but it's like—

Jackson: (2:31:07) One of the characters who shows up a couple of different times. I was trying to find the real source.

Ian: (2:31:09) I think it's on Playground Psychotics, which is a great Zappa period. It's when he had Mark Volman and Howard Kaylan—I hope I'm getting their names right—from The Turtles with him. It's an amazing Zappa era. Live at the Fillmore, 1971. Playground Psychotics is the one to go listen to.

Jackson: (2:31:29) That’s the way in? I haven’t really listened to him at all.

Ian: (2:31:35) There’s no way into Zappa because it’s funny. I had this conversation with Gail Zappa when she was still alive. Frank was no longer alive, but Gail was, and she was looking after the estate. She was very reluctant to put Frank's music onto streaming. I tried so hard. I think there was one moment when I got through to her. I said, "Listen, Frank's music is a genre. He's not an artist. It is a genre of music." It doesn't matter who you are. There is a Frank Zappa song you are going to love, and there is one you are going to hate. There's everything in between for every human being on the face of the earth, I promise you. No one is going to explore that catalog like I did, Gail—one double or triple CD set at a time for $29 each. I was spending my last dollars buying Ryko discs in college—Zappa CDs, Bowie CDs. That's what we were doing. But the way in would be Hot Rats and, actually underrated, Bongo Fury. Frank Zappa and Captain Beefheart. Super underrated, 1976 I believe, because there's a song on there called "200 Years Old" which is about America. We just turned 250 years old.

Jackson: (2:32:56) Anyway, no pigs, no ponies. What do you think you're resisting? How do you keep holding on?

Ian: (2:33:05) I have no idea. I'm not sure that I am. The older I get, I feel very lucky to have made it this far, to be honest. I wish I could see how the puzzle pieces fit together exactly, but I'm not quite there yet.

Jackson: (2:33:26) I think you’re holding on to some kind of—we talked about it this morning. There’s a fighting inertia that I admire in all kinds of people. I think the longer you fight it, and the longer you hold on to the punk rockness or the curiosity, life stays interesting.

Ian: (2:33:40) Yeah, it's definitely interesting. I look at a lot of inspiration. I just saw Mike D play here in Paris. Mike’s 60 and he's on stage with his kids playing an amazing show, being Mike D from the Beastie Boys. There's a long story that I'll make short. I was sitting having tea with Paul McCartney in his house once upon a time, and he said to me, "I met Eminem last night." I said, "Oh, how was that?" He said, "Eminem said to me, 'You're Paul McCartney?' I said, 'Yes, I am him.' He said, 'Do you feel like Paul McCartney?'" I was like, what a weird thing to say. Paul said, "No, I know what he means, because normally I just feel like a bloke having a cup of tea. But then I get on stage, I put on that Rickenbacker, and I feel like Paul McCartney from The Beatles." Those are the stories. Paul’s in his 80s and he’s still curious and pushing and wants to be relevant.

Jackson: (2:34:52) And he’s still kind of amazed by it all, I think.

Ian: (2:34:53) Totally. Which is the cool part. I was so happy for that opening because I wanted to ask you, do you ever look in the mirror and go, "Yo, I was in The Beatles"? He was like, "I do. It's crazy." But that's great too. That's inspiring. Hanging with Glenn Friedman, who’s ten years older than me and still as idealistic as ever. Seeing that Henry Rollins and Ian MacKaye are putting out The Cramps discography. It's just this reminder that as long as we're breathing, we can still create and participate.

Jackson: (2:35:32) Participate. Put beauty in the world.

Ian: (2:35:32) Yeah, participate. Put beauty in the world. I say that and then ask, is putting The Cramps compilation in the world beauty? It is to me. Those are the things that inspire me.

Jackson: (2:35:45) Thank you. That's all I got. We're way over time. I appreciate it.

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