Description

Jack Conte (Patreon, YouTube, YouTube Pt2, X, LinkedIn) is the co-founder and CEO of Patreon. He is also a lifelong artist and musician, who at his peak released 100 music videos per year between his bands Pomplamoose (a duo with wife Nataly Dawn) and Scary Pockets (a funk collective), and was a longtime YouTuber.

Jack is not a tech CEO who happens to like music. He is an obsessive, prolific artist whose first conventional job is running Patreon. This has shaped him as a founder and executive, and his mission at Patreon is to build an enduring and truly creator-first company that empowers creators to earn a living from their work.

We began with how he manages to do it all, where his energy comes from, and what it’s like to be “post-chaos.” Then, we talked about art, content, and commerce, Patreon’s model (that isn’t actually pure patronage), and why Silicon Valley undervalues art, brand, and narrative — and Patreon. Jack shared the benefits of a business model that is fully aligned with creators, why he hates the word influencer, and why he’s still the right man for the job after 13 years of leading Patreon. We also covered what great leadership looks like, building fans and community, filmmaking, authenticity (from Charlie Kaufman to Prince), and remembering to take risks until the very end.

I hope you’re inspired to make things you are proud of and to draw the next page even when you have no business doing so.

While I have you: I’d strongly recommend Jack’s recent SXSW talk on AI, creativity, and change.

Full transcript and all links: dialectic.fm/jack-conte

Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Learn more about Notion's new developer platform and workers here. You can learn more at notion.com/dialectic.

Timestamps

(0:00) Opening Highlights
(1:38) Intro to Jack & Thanks to Notion
(3:44) Start: Prolific Output, Energy, Juggling, Endurance, and Becoming Post-Chaos
(22:04) Combining Creativity and Business and Art vs. Content
(33:21) Advertising vs. Membership & Patronage vs. Patreon
(44:06) Jack's First and Only Job, and Silicon Valley's Undervaluing of Creativity, Brand, and Storytelling (and Patreon)
(55:17) Building for Creators First, Incentive Alignment, Trust, 100 Years of Patreon, and Why Jack is the Right CEO for Now
(1:04:49) Leadership: Types of Ambition, Obsession, Self Reflection, Bias to Action, Learning from Others
(1:12:59) Talent vs. Enthusiasm, Being Proud of What You Make, Making Fans and Being True, Managing Parasociality, and Community
(1:28:30) Filmmaking, Labels and Collectives vs Individuals, Breaking Patterns, Creative Intimacy, Music, Patreon's Origin, Persistence, Lucid Dreaming, and Taking Risks
(1:49:26) Thanks Again to Notion

Transcript

(3:44) Start: Prolific Output, Energy, Juggling, Endurance, and Becoming Post-Chaos

Jackson: (3:44) Jack Conte, thank you for joining me. Or thank you for having me.

Jack: (3:47) I should say, gosh, thanks for being here.

Jackson: (3:49) This is a pleasure. We have a mutual friend who really raves about you, and it's an honor to have gotten to kind of dumpster dive the archive and get to chat with you.

Jack: (3:58) Nice, nice.

Jackson: (3:59) I want to start with maybe that last point. I knew a bit about—I knew you had the band with your wife, and I knew you had made YouTube videos and you kind of made Patreon for yourself. I guess the idea I had in my head is that you were a CEO who kind of liked music and had done some YouTube in the past, which is decidedly not the case. I'm sure I'm missing some, but I think you've had four quite successful YouTube channels, maybe three. You are, for lack of a better word, just wildly prolific, even ignoring Patreon. I think that speaks to a level of endurance. It speaks to, frankly, just being multi-hyphenate or polymathic. But I'm curious, across all of these things, including the business, how do you sustain your energy?

Jack: (4:51) I don't know the answer to that question, but I do get asked that a lot because Pomplamoose is making 50 music videos a year. Scary Pockets is making 50 music videos a year at the same time. So I was outputting 100 music videos per year and doing Patreon and had an active Instagram presence. Also, it's not like I'm not doing work at Patreon. That is the triple-time job. That is my absolute focus. And those things were, for me, in the cracks. I think the answer to the question, the best I can do, is that there's really a couple things that it came down to for me. One was batching production on the media side. When I was trying to make everything by myself and doing one thing at a time, I just couldn't get through the last 5% that was 20% of the work. So the system that we ended up setting up is flying down to LA for a Saturday and a Sunday, because I'm working all week, once a month. Literally one time every four weeks, I fly down to LA on Saturday, do a session with Scary Pockets, which is my funk band, record four songs in a day. On Sunday, I do a session with Pomplamoose, record four songs in a day. Both bands are profitable, and so we can hire teams. We had a post-production crew, audio mixing engineers, mastering, video producers, video editors—full production teams.

Jackson: (6:19) Yeah, these aren't hobbies either, which is the craziest part of this.

Jack: (6:25) No, it's like a whole operation. 100 music videos a year is serious output. So we had this system to get eight songs in one weekend, and then the teams would sort of take those songs and mix and engineer and make videos out of them. That got me to the point where I was releasing two music videos a week, one with Pockets and one with Pomplamoose, while I'm up here doing the company. I don't want to say it's a magic trick, because it's not like I'm in the recording studio every week or every day, which is maybe what it looks like online. I mean, I'm here every day. Batch production was a big thing. And the idea of leaning into everything I learned at Patreon around working with teams, applying all of that to Pomplamoose and Scary Pockets—the power of a team, the output of a team is exponential compared to the output of a person. I'm really thinking about how to leverage teams and work with teams and build operations around—I don't like the word content, but around a content pipeline. Then, I know this is a highly contested thing in Silicon Valley. There's two camps. I do not function without my chief of staff. I know that role—there's people who are like, "If they have a chief of staff, I'm never investing." I literally wouldn't work. I couldn't do it without my chief of staff. She's the best.

Jackson: (7:50) How long has she been with you—this is Nicole?

Jack: (7:52) Yeah, it's Nicole.

Jackson: (7:53) How long has she been with you?

Jack: (7:53) Eight years.

Jackson: (7:54) Wow.

Jack: (7:59) And the first six of them she was my EA. I don't work without her. My life doesn't work. She is very much the executive function side of my brain. I have so much inbound across Slack and Google Docs and Notion and email and Teams and Scary Pockets and Pomplamoose. I cannot operate without an amazing human who's going through all of that and constantly triaging and making sure that I'm constantly working on just the most important three things. She is really good at that. She has full context on my life, on everything. So that's the other huge unlock for me: learning to work really effectively with her and finding someone who's as good as her in that role. So batch production, having an amazing chief of staff, and then there is one other thing which I'm still working on, but it's just fucking getting used to chaos. There's a lot of people who think chaos is a sign of failure or like something not working or like we've done something wrong and we have to fix this chaos. I'm post-chaos. I accept the chaos of life and company building. I'm now just at the point where I'm like, that is going to be the baseline: chaos, disorganization, things changing, schedules changing, priorities changing. I'm getting used to that kind of just being how things are. It's always going to feel a little stretched. It's always going to feel a little unwieldy. It's always going to feel like a little bit too much. But actually, I've gotten a little bit better at relaxing into that.

Jackson: (9:42) That is an amazing or at least a helpful strategic context for how this all happens. It doesn't explain how you do this for 15 years. Obviously you love what you do, although even that's a cliche. What does that totally mean? Are there parts of this where, as an example, maybe performing when you're down in LA with the band isn't really this generative part of your brain? Maybe generative is the wrong word, but it's not like songwriting or something where it's just actually purely energy giving. There are parts of that—I don't want to make it about burnout, because I think that's probably even—

Jack: (10:20) Yeah, I hate that word. I don't think of it like that.

Jackson: (10:23) But presumably some of these things are energy positive and some of them are energy negative, and enough of them are energy positive that you're staying above water. Or you're just a sicko.

Jack: (10:30) But no, no, no. I have so much. And as I've operated more, I've gotten better at leaning into things that are energy positive for me. I would say one of the main differences between me as an early operator and me 13 years in is that I used to be just super growth mindset—leaning into the things that are my weaknesses and trying to make them better and learn and grow. Of course, I still want to do all of that, but that takes you only so far. I can get from a B-minus to maybe a B-plus on a lot of those things in a year or two. And I'd rather have somebody else nail those things and delegate that and have somebody do them better and just make sure that we're aligned from a strategic and vision standpoint on a lot of that stuff. Then I'm trying to lean more into the things that I think I'm really good at—what are my spikes? And then I want to spend more time on those things. I've spent a lot more time over the last couple years on a lot of that stuff, and that is super energy-giving for me because that's the stuff where I'm in flow. On a lot of things, I feel like I'm worse than a lot of people. I'm like, "Ooh, there's another person who's going to do this way better than me." And then there's a couple things where I'm like, "I think I'm one of the few people who can really crush this." And so I spend a lot of time doing that stuff. I also love those sessions with the bands. I love performing. I love recording days. When I'm in a studio, my confidence goes through the roof. I feel like I know exactly what to do. And it's so much fun and I make such fast decisions. It's 100% intuitive. I've learned a lot, actually, as an operator from how I show up in a recording studio. There's a lot of that that I'm trying to pull into how I operate here. It's not one-to-one, so you have to be careful pulling too much, but that has been a lesson for me. And then there's enough of those things such that I have a good, happy life and a fun time. And then when it's not—which is also... there's lots of those moments where I think a lot of people would characterize it as burnout. The reason I don't like that word is because for me, it's a bit like the word "death." It occupies a space in your brain that is irrecoverable, and I don't think of it like that. So whenever I'm like, "Fuck, I'm done. I got nothing left. I'm out of gas. There's too many things"—this might sound silly or almost pedantic, but I literally sit down at a piece of paper, or a note on Apple Notes, and I go—on device, not cloud. I don't want this shit on the cloud, on device. And it's like, "What am I feeling right now?" I start with that. And it's like, "I'm anxious as fuck. I'm scared. I'm demotivated." I'm talking about the moments where it's really bad, like maybe twice a year, three times a year. It's not very often—this isn't a weekly or monthly thing—but a couple times a year, it's like, "Fuck, I hate everything." I literally start with how I'm feeling, and I'm like, "Why am I feeling like that? What are my narratives around that feeling? What is it that I believe to be true that is making me feel that way?" And then I list out my narratives. I'm like, "Okay, objectively, how many of those narratives are real and how many of them are things that I'm assuming?" It's like, "Okay, actually, I don't know that this one is actually true. Okay, let's cut that one for now." But what are the actual problem statements then that come out of the narratives? And then I have a set of problem statements. And it's like, "Okay, now let's prioritize those problem statements." Again, I'm sorry if this sounds pedantic,

Jackson: (14:31) But it's like, this is exactly what I was asking about.

Jack: (14:36) It's like, "Okay, here's my seven problem statements." And what I found is usually when I feel really shitty, what it actually is is a compounding set of four or five problems that are all really gnarly hitting at once. That's when I'm like, "Fuck it, I'm done." And I think a lot of people would call that burnout. And so when I hit that, I list out those problem statements, I make them really crisp. I get into what is the actual problem. And then—this is so silly, but it's so effective—I list out a bunch of potential solutions for each of them, and I do the first three. Do the first three for each one; do the first three hypotheses that could potentially solve that problem. Sometimes it's as simple as emailing a person, setting up a phone call: "Hey, here's the story in my head. Is this true? What's your experience of this?" and working through something. Immediately after doing the first three things for four or five problems, I feel so much better and I'm like, "Ready to go again," because I can see a path.

Jackson: (15:37) It's real. Like, you've put it on the table and you can look at it. Exactly, yeah.

Jack: (15:41) Yeah. So I don't know—if you were to go through my computer, I probably shouldn't say that, but you'd see a series of brain dumps over the years. Problem statements and then little solutions to solve each one of them. Sometimes it takes a couple weeks, sometimes it takes a couple months. Occasionally it takes a year to get out of a really gnarly problem. But usually within a year, I'm out of the problem and then there's a new set of problems and I can do another brain dump.

Jackson: (16:12) Yeah, it sort of assumes that burnout—or to use the stronger word, death—isn't an option. I forget exactly how you framed it, but something along the lines of it assumes that you could truly run out of gas. And you've adopted an orientation that says, whatever the lowest point is, I will bounce. Inevitably, I will bounce back. It's almost like a belief thing, I suppose.

Jack: (16:37) A thousand percent. So I actually don't think—there's another one of these controversial statements here—but I don't think, up to a certain level, your context is really important. Do you have enough food? Are you safe? Do you have shelter? Do you have enough money to get things done in your life? All that kind of stuff. But I don't think... one of the things my wife says I agree with—I forgot who exactly said this—is, "Wherever you go, there you are." So I don't think changing my environment or my job or my context or my partner or my house is going to solve fucking anything. Wherever I go, there I am. So I better get good at solving the actual problems. Because the problems that we think... when you think about, "Oh, I'll just change the context," I think 5% of our happiness, at least my happiness, is context. I think the rest of it is brain chemistry and specifics. And then it's like, "Okay, let me either work on the brain chemistry or let me work on the specifics."

Jackson: (17:44) Can you successfully work on brain chemistry?

Jack: (17:46) Yeah, yeah. And I do. I go to therapy. I mean, I don't know if that changes my actual physiology, but it certainly changes my psychology. And that has a profound impact on my happiness and my ability to kind of keep going.

Jackson: (18:04) It's funny, I think on one hand I agree with you on that. Wherever you go, there you are. I think environments and context matter a lot, but we often blame things that are ultimately about us on the environment. And that's the "If only I was." The grass is greener. I think environments can be underrated, but not for these internal things, which is really risky.

Jack: (18:26) I mean, I'll give you an example. I like doing things. I get energy out of publishing work and reaching an audience and building community on the internet.

Jackson: (18:40) Those things, by the way, are different. Publishing the piece and sitting down in the room by yourself to write it are very—

Jack: (18:46) So different. And I like both. I actually really like—

Jackson: (18:49) So you really like—do you get energy from, like, Jerry Seinfeld talks about writing. He's like, you lock yourself in the room every day and you don't have to write, but you're not allowed to do anything else. And maybe it's a distinctive thing of writers, but I feel like so many writers love writing the idea and they excruciatingly hate the process of having to sit down.

Jack: (19:07) Yeah.

Jackson: (19:08) Do you get energy from the quote-unquote boring things or the drudgery things?

Jack: (19:14) So I've talked to a lot of people who are like, "I don't want to write songs, but I want to have written songs." I am the opposite, really. If I am in front of Ableton Live and crafting up a MIDI baseline and running synths through plugins and reversing a piano and adding a tape loop—I will literally forget to go to the bathroom. I will forget to eat. I will wake up six hours into the process and be like, "Oh my God, my bladder's about to explode." And then I have a run. I lose myself, I'm gone.

Jackson: (19:50) You've got Ableton psychosis. I've heard about Claude Code psychosis, but it's Ableton psychosis.

Jack: (19:54) It is that for me. It is the most unembodied—

Jackson: (20:00) Are there things like that for Patreon, presumably? Patreon is a hugely mission-oriented thing that is largely about the way you're serving the world. And not to say music can't be that too. So is it a different kind of thing or are there—

Jack: (20:13) So different. And this is my struggle in life, which is for me, the process—call it the input-level behaviors associated with making music—are the most joyful, wonderful behaviors. They are intrinsically motivating. They're what some people call autotelic, which is a behavior that you do for the sheer enjoyment of the behavior itself, not for some expected outcome. That is what music making is for me. And those behaviors just give me instantaneous joy—presence. And sometimes I would even call it lack of presence. I don't even know I'm there anymore. I'm just so in the work. Patreon is not that for me. And maybe—I don't know—I've talked to a lot of founders over the years. People say, "Do what you're passionate about." And I agree with that. I get that. The thing for me with Patreon is the outcome of Patreon is so deeply motivating and inspiring to me. The impact that the company has on people and creators and the world and culture, it gives me immeasurable meaning in my life.

Jackson: (21:32) Like even purpose.

Jack: (21:33) Purpose. It feels like the reason I'm on earth. It feels like the outcome is—I can't imagine a more rewarding outcome. And then the day-to-day behaviors are nowhere near as joyful as—

Jackson: (21:48) It'd be way more fun to be making music.

Jack: (21:49) That'd be so fun. And so this is my struggle. I love this set of behaviors. I love that outcome. Man, if I could do that set of behaviors to get this outcome, life would be amazing. But you're full of choices.

(22:04) Combining Creativity and Business and Art vs. Content

Jackson: (22:04) Why for you—and I guess this obviously may be an easy question to answer for some people—but why was it so important to make your creative life a business, even pre-Patreon?

Jack: (22:23) I love the craft of music making and creation. I love it. It's just so fun for me. There's another piece of my brain that is the mechanics of system design, business building—whatever you want to call it. I also love that. There are some artists—in fact, we have three personas of artists that we often talk about at the company. There are some artists that are like, "Look, I want to play guitar and smoke weed and write songs. Don't bother me with anything else." In fact, sometimes I wish I was that type of artist because those artists make amazing work. And they end up working with a team who handles everything, and they just get to play guitar all day. That's amazing. Sometimes they get taken advantage of because they're not paying attention.

Jackson: (23:24) Almost like the original benefactors of real patronage. Like, the only way that person was alive or surviving a hundred years ago is real patronage.

Jack: (23:33) And that is a category of ours: persona type one. Then there's a second persona that's like, "Yeah, I'll do some other things." And sometimes the administrative work—they don't love it, but they'll do it. They don't hate talking about money, but they don't love it, and they'd prefer not to—but they'll manage their Patreon income and sell some merch and run their thing. That's the second category of artists. There is a third category of artists—I forgot what we call them: Empire Builder, Architect. I don't remember what we call them, but there's a category of artists that's like, "I love the business part. The business part lights me up." It's creative, and I get to design. These artists are like, "I'm a media company." They're like, "I make media." And they think, "How do media companies make money? They have an events business. I could have an events business. They have an exclusive content business." They're segmenting their freemium media from their premium media and they're thinking about their strategy. "Look how the New York Times grays out a third of the way through the article. What's the video version of that? Maybe I can do that with my videos. Okay, I'll put a call to action second." Blah, blah, blah.

Jackson: (24:44) Those are the founders.

Jack: (24:45) Exactly. And there's a lot of artists that just dig it. They like that stuff. I have always liked that stuff.

Jackson: (24:53) What do you like about it?

Jack: (25:01) I like that it's so different from the music creation. And again, I like both. I think I probably like the music creation more, to tell you the truth, but this stuff is really fun for me. What do I like about it? I like that you can make—this stuff is so hard to measure, and it's so hard to know, "Did I do a good job?" And it's so subjective.

Jackson: (25:22) Clear feedback loops.

Jack: (25:26) And this one is like you just put the things in place and you know if it worked or not. There's something checklisty about it that is just nice to see progress over time.

Jackson: (25:35) It's also just a different part of your brain, probably.

Jack: (25:38) It's a different piece of your brain.

Jackson: (25:41) Creativity.

Jack: (25:41) Yeah. And so I feel when I'm doing all those things, I feel very whole. I feel like I'm being my whole self.

Jackson: (25:49) You talk about media market fit. Maybe the first question here would be: what is the difference between content and art? Which is obviously a very big question—we don't need to spend all day on it—but roughly. I think the reason I'm interested in the media market fit thing is, on one hand, it's really compelling and really interesting. On the other hand, there are maybe things we gain when creative people are really attuned to the market, and there are things we lose when creative people are really attuned to the market. Maybe even to your stoner guitarist-to-founder spectrum. And so maybe one vantage point or cut on that would be the gradient between content and art. What aspects are at play there?

Jack: (26:27) Yeah, big wide gradient. Totally non-binary distinction. It's hard to talk about it. I'll give you the ends of the spectrum and maybe some things in between and how I think about it. One way to think about content is its purpose is not necessarily the transference of an emotion to another human that the creator of that piece had. The purpose is some intended outcome that I think of as content. For Netflix, of course they call it content because their purpose behind the content is adding new subscribers to the system and increasing revenue. So they think of it as content.

Jackson: (27:20) The artist doesn't. Or the creator of that film or TV show doesn't necessarily.

Jack: (27:25) No.

Jackson: (27:26) So the same thing could actually be, depending on who's talking about it—

Jack: (27:30) 100%. This is another reason I don't like the word influencer. I feel like influencer is the commoditized attribute of an artist that is valuable to corporations: the influence. They call that person an influencer because they're like, "That's the piece of that person that I care about. I don't care about the rest of them. I care about their reach." That's the commodity. By the way, it commoditizes artists because I can get influence from there, or from there, or from there, or from there. As long as there are eyeballs on the other end of that influence, it doesn't matter where I get it from. It turns artists into corn or steel. Content for me is a little bit of that same type of thing. It's more commoditized, it's more outcome-oriented. It's more trying to achieve something; there's a goal behind it. Versus, when I think about art, I think about—I never remember if it's Tolstoy or Tchaikovsky who basically said—art is when the person who's creating the art felt something and wanted to communicate that feeling to another person. You end up literally transferring that feeling you had into another person. That is the process of art. And that has always stuck with me because my favorite art is when I finish it and I feel something. When I feel something, I think maybe that person who made that thing wanted to get me to understand something in a way that was emotional, not logical even. I don't know if that's exactly what they were feeling, but they told me something emotionally there. That's my favorite art in the world. And there is something—I've heard Rick Rubin talk about this, and he talks about the difference between art and commerce. I think it is possible to make art and also to want to get paid for your art. If you're an artist and you want to be paid for your work, that's not commerce. That's you feeling like you have value. That's having a sense of self-worth. That's recognizing that you're creating value for the world and you want to be compensated for your contributions to society. That's totally legitimate. I don't think that's some pejorative version of art.

Jackson: (29:58) It's challenging because art is—I would certainly agree that art is valuable. I think art can sometimes be useful. Perhaps the challenge, and perhaps why the idea of patronage is so interesting, is that the more entangled the art-making gets with the commercial side of it, the fuzzier all of this gets and the incentives and everything else. Maybe it's just what we believe about the artist's intentions, but so much of it is that.

Jack: (30:24) Yeah, so much of it is that.

Jackson: (30:27) Not even what they actually are, but what we believe they are.

Jack: (30:30) Art is also made, as far as we know right now, exclusively on planet Earth. Most of planet Earth is engulfed in an economic and financial system that is the context for art-making. You can try to separate those as much as possible, and you can try to say that you're making art in a vacuum. There are a lot of people who do a really good job of that. But for me, this is my problem with the term "selling out." I think selling out is doing something other than making art. If you get paid for your art, that's the opposite of selling out. That's making sure that you're setting up your future so that you can make more art.

Jackson: (31:25) Right. It goes back to the endurance point.

Jack: (31:26) Yeah. Creating a sustainable path for yourself to make art is a beautiful thing.

Jackson: (31:38) My friend Trevor McFedries says selling out is punk. Because, by the way, if you're selling out now, it means you're probably not a nepo baby. The only choice to actually make your thing is to sell out, which is funny.

Jack: (31:48) Yeah. I think there are ways to make money that are really cheesy, or dishonest, or smarmy. You can be an artist and do that. You can be an economist and do that. You can be a PM and do that. You can be a founder and do that. But I think there are also ways to create value as an artist and be compensated for the value that you're creating that are wonderful and pure and reasonable and kind and good for the world. The reason I'm pushing so hard on this is because so many artists—those two-thirds of artists—almost think that if they make money from their art, it's evil. I'm on a mission in life and in this company to help creative people understand that they have meaning in the world. We've been looking at these dashboards on social media companies for 20 years now that tell us, "You just got 3 million views and that's worth $18 in ad revenue. That's your worth to the world." I think that's a load of horseshit, and that shouldn't be the case. It's going to take a lot of convincing artists that, no, that's the system saying you're worth only that. You're worth way more than that. You're creating so much more value than you're capturing as an artist. And that's a key piece of Patreon's mission—just to change how people even think about their own self-worth as artists in the world.

(33:21) Advertising vs. Membership & Patronage vs. Patreon

Jackson: (33:20) Why are fans paying the artists that they enjoy? That's obviously not a crazy idea—it's existed for a while—and yet it seems that what you do is not that common. Why are you so bought in on that being a great model for artists?

Jack: (33:40) What I love about this question is that for thousands of years, pretty much every piece of great art that we have ever known, any piece of art in history books, was funded basically through patronage. It was funded because somebody was like, "I really like what you make. You're cool. Here's a bag of coins, go make more cool stuff."

Jackson: (34:00) Or God wants it or whatever, right?

Jack: (34:00) Or God wants it or the government wants it. Then in the early 1900s, humanity figured out how to record light onto celluloid paper and record sound onto a wax cylinder. And we were like, "Oh my God, you can put art on a physical object and you can ship that physical object to consumers, and they will purchase that physical object not because of the materials, but because of the art that's encoded on the object."

Jackson: (34:25) Although I will say I think the distribution friction and cost made it easy to justify charging for it.

Jack: (34:33) Only the distribution and cost and lack of scarcity, and cost of materials. And so that created a hundred years of an infrastructure build-out: jewel cases for CDs and cardboard record sleeves and magnetic tape in VHS.

Jackson: (34:51) Also worth noting: really good for musicians and filmmakers, but not that good for a whole bunch of other mediums, right?

Jack: (34:58) No, exactly. But anybody telling stories with sound or moving pictures, it was great for those folks. Over the 1900s, all this industry popped up that was around the distribution and economics of unit sales as a replacement for patronage as the main economic model for artists. It became CD sales or tape sales or laser discs or Blu-rays. And then the Internet came around and suddenly the thing that you said made those objects valuable—scarcity—disappeared. Pieces of art were infinitely replicable and no longer scarce. The early experiments with what we were going to do here was Napster. Then it was like, well, there should be some type of economics around this, which was iTunes. Then about five years into that, it was ad revenue. Sometimes I think of ad revenue as basically the go-to-market strategy for the web.

Jackson: (36:04) I would argue it's probably the only truly defined and great business model of the Internet as it currently stands. You're trying to change that, but it's the only one we really found.

Jack: (36:14) It is the mature one for sure, and the one that started the earliest. I think also humanity is reckoning with all the problems associated with that model.

Jackson: (36:25) It's the one that's least fighting gravity from a user experience. There are a whole bunch of things structurally about music that actually make sense for it. I shouldn't have to pay a dollar to listen to a song once, right? I'm going to enjoy it the more I listen to it.

Jack: (36:38) Free experiences for the end consumer will always beat paid experiences for the end consumer, straight up. And so that's why the Internet got to scale so quickly. This technology was invented and 20 years later, billions of us are using it. That's because it was free. If it cost everybody 10 bucks to get on it, I'm not sure we would have seen it explode like it did. So it was a great way to get things up and running and to get humanity connected. But I think the early companies that won there thought of art as a subcategory of information. They were like, "Information should be free," information such as art and news, and artists were like, "What?" I looked up one day and just felt like this system is not working. In a day and age of infinite replicability and a lack of scarcity and no more physical objects with your art on it, how are artists going to get paid? Strangely, it initially was like going back to before those objects existed in the first place—back to 1900, pre-magnetic tape, pre-wax cylinders, pre-Edison cylinders. Back to the bag of coins because you're doing something cool.

Jackson: (38:06) Is there any serious history of a more democratized or fragmented patronage? Because the obvious huge difference is that back then it was a rich guy.

Jack: (38:18) The Medici family and some governments.

Jackson: (38:20) It's funny, I sometimes joke that my podcast is free for all listeners, but I have one sponsor—it's Notion. They're a software company, they're great. They're my patron, quite literally closer to the Medici than before. Obviously, the big difference in your worldview is that it's not going to be one guy or even two guys or three. That has a lot of things that are structurally different, including when your core audience and your customer are the same group. There are good parts of that and there are bad parts of that.

Jack: (38:54) Interestingly, patronage for us was where the company came from and was the first thesis behind this model that we started building. It's the emotional truth of what Patreon is and the narrative truth of what it is. But what we have found years in—not even that far in—is that we needed to work on a different way to think about it. The truth is a lot of artists are like, "I don't want to put out a hat and ask for money. I'm reaching millions of people. I'm a badass. I'm going on tour and selling $5,000 worth of tickets. I'm not going to busk on the Internet. I'm not doing patronage." That feedback was loud and clear. What we saw was that the way of thinking about Patreon has to be that it's not a donation. It's very important that it can't be a donation. It's not just a positioning thing or a marketing thing; it's in the product. We built this CRM that's more about running your business, getting the email address of the fans, and building the direct relationship with your audience. We built one-time payments, which allows artists to transact and sell a piece of digital media or a collection of a back catalog of videos.

Jackson: (40:20) I love that. The fact you can buy a single video for $8 or whatever—which is maybe a lot for a video, but I wish I could do that on Netflix. It's great.

Jack: (40:29) We built a more robust membership system. Before Patreon in 2017, you could be a member, but you were a member of a gym. I don't even know if people realize that we literally invented the category of digital creator membership. No one was using that term. You couldn't become a member of a creator; you could become a member of an organization. There was no membership for creators before Patreon started calling it that and building the product. Then, during the pandemic, that really took off with podcasters. Membership as a category started taking off even before the pandemic, but it got augmented during COVID with the podcast explosion.

Jackson: (41:18) Why do you think it was?

Jack: (41:19) Because podcasting is episodic, and the dollars per watch minute to produce podcasts is—that’s an amazing ratio for podcasters. Versus animation, for example, which is very costly per watch minute.

Jackson: (41:35) Was it initially primarily fully gated shows, or shows that were two-thirds free, like Josh Citarella or whatever, where there's a bonus episode?

Jack: (41:42) This is precisely what changed over the course of the pandemic, because that's when New York Times subscription revenue surpassed their ad revenue. And it's when The Guardian introduced premium and freemium. Now, there are no publications who don't have some type of freemium and premium. Even Disney and Netflix, they have the free tier and they have the paid tier. It's kind of in the public consciousness now that if I am a producer of media on the web, some portion of that media should be gated and some portion should be free. There's a fan journey associated with that free-to-paid conversion that is important for artists. That was not a part of the internet 10 years ago. That's new in the last five or six years, that that's become part of the public consciousness.

Jackson: (42:28) Maybe there were flickers of this on Twitch or OnlyFans. I don't know when that showed up, but even that, I don't know if it's quite the same psychology. It's a little different.

Jack: (42:41) Yeah, there were always—I don't want to say always, but even in the early days of the web, there were things that artists were posting that you could pay for. I remember in 2011, Pomplamoose, my band, was doing paid live webcasts. We had a show and a red curtain, and we sold tickets.

Jackson: (42:59) Why do you think that hasn't worked more? Is that working at all on Patreon?

Jack: (43:02) I actually think there is a reason. I think it's very hard to make something live that is super engaging, versus if I'm going to spend half an hour watching something, if I front-load six weeks of work into making a really engaging half hour, it's just so much easier than doing a bunch of production to make an engaging half hour live.

Jackson: (43:27) Totally. And this is why livestreaming—the average streamer streams for six hours—is actually a lower bar, longer duration. You're watching it while you work, whatever. That makes sense.

Jack: (43:36) And what you're streaming is actually something that someone else has produced and spent a long time producing and making excellent: games. The graphics, the intrigue, the strategy—you're watching a game, and then what makes it compelling and why you're not just watching a game is because there's an awesome human who's talking about it.

Jackson: (43:56) Yeah. Or even Speed and Clavicular and the crazy—they have to go to such an end of spectacle to—

Jack: (44:02) Right.

Jackson: (44:02) To...

Jack: (44:02) Yeah.

(44:06) Jack's First and Only Job, and Silicon Valley's Undervaluing of Creativity, Brand, and Storytelling (and Patreon)

Jackson: (44:03) We don't have to get into that, but I think this is a helpful transition, maybe along a similar point, which is one thing I've observed is that a lot of the big consumer internet companies the last 15 years, we think of them as technology companies, and they obviously are. But the breakthrough—obviously they're hosting live video or whatever, these things are not easy—but if you look at you guys, or even Uber or Airbnb or Twitch, it's actually culturally normalizing a behavior and saying, "You're allowed to do this." Obviously, I assume some of this is emergent, where you're having your creators or your fans telling you to do this. But I'm curious what you've learned about how that actually happens.

Jack: (44:45) Slowly. I remember pitching Patreon to investors in 2014, and one of the main pieces of pushback was like, "Wait, so you guys are going to ask people to pay for something that's free on another platform?" And I was like, "Yeah."

Jackson: (45:04) At least with Twitch, it's on the bottom right. It's on YouTube.

Jack: (45:08) And they were like, "Thank you. Good luck with that."

Jackson: (45:10) Didn't you raise money pretty quickly?

Jack: (45:14) We raised $700,000. We got a term sheet for $700,000. We ended up raising the ceiling for the round to $2.1 million about three months after launching.

Jackson: (45:26) But it wasn't working yet. Or was it?

Jack: (45:27) No, it was.

Jackson: (45:28) So it kind of worked right away.

Jack: (45:32) It worked immediately. I have to caveat when I say that, because a lot of people are like, "Oh my God, that's amazing." But what isn't said there is I tried 5,000 other things that went absolutely nowhere. This was one of the 5,000 things that worked.

Jackson: (45:52) Yeah.

Jack: (45:52) And so there was that product-market fit hunting phase. I never set out to start a company; I never thought, "I want to make a company and that's going to be my life." This was just one of the hundreds of projects that I was working on that took off right away. And so we just leaned in over the years. Anyway, that's why I think it's not remarkable that it worked.

Jackson: (46:14) What about—presumably you guys have done this multiple times, including the shift from donation to actually selling digital goods? Even that is a version of culturally normalizing something. At least from my view, you guys have done this, and I would even add new categories on the platform, like being able to actually take hold in the board game world or in the podcast world. Is most of that just being really attentive to what's happening on the platform, or are there ways that you can kind of bend things in the direction you want them?

Jack: (46:46) Yeah, my take—so, again, I come from the world of YouTube. I come from the world of artists and creators. I've never had a tech job. I've never worked at another tech company. This is the only company I've ever worked at in my life. This is my first job that I've ever had.

Jackson: (46:58) Really?

Jack: (46:59) Yes. This is my first time I've—

Jackson: (47:00) Ever worked? Straight out of college, music, and then YouTube?

Jack: (47:04) I worked as a contractor. I taught, I was an SAT tutor, and I was a contractor doing in-house background music for corporate videos for Google. But I was just composing, right?

Jackson: (47:15) You did voice some characters on the Sims 2.

Jack: (47:17) I was an actor. I was the voice of a teenage boy. So I did all that, but I never went to work at a company every day. So this is my first job. My read after 13 years of working with all kinds of different execs and people in Silicon Valley is that Silicon Valley often just looks so out of touch with the rest of the world. That's why there's so much pushback and, honestly, a lot of just backlash and hatred of tech in the last 10 years. I think a lot of it is because the Valley undervalues brand, narrative, creativity, storytelling, and a lot of these things that in my world, where I come from, those are the things. Those are the things.

Jackson: (48:08) It's all you got.

Jack: (48:12) And in Silicon Valley, the main thing is the product, which is really true. The main thing is the product.

Jackson: (48:18) Also, the projects are magic. Half the time ChatGPT comes out, you don't need a lot of narrative.

Jack: (48:22) You don't need narrative because the product is so—it just—it is incredible. And so I don't mean to say the product isn't the thing. At the end of the day, 99% of people, their interaction with the company is going to be the product. And so the product is a thing. But you can know that the product is a thing and care about narrative and creativity and storytelling and brand, or you can not care about those things. And I think if you don't care about those things, it's very hard to influence culture and to build a brand that people love and to have trust with your customers. It's very hard to do those things. A lot of those things are a completely different skill set. It's a completely different mindset. It's a different way of thinking about the world. There's a lot of operators who, if it doesn't show up in the P&L, they don't believe that it's real. Then there's some operators who actually operate from a place of conviction and belief in, "Hey, this is going to build trust with customers." It's going to be hard to see the incremental impact in the P&L, but I know it's going to build trust with customers and that's going to create loyalty and that's going to improve retention. It's going to improve conversion at every stage of the funnel. And so from a place of belief and conviction, we're going to do that. There's a type of operator that believes that and there's a type that doesn't. And I think Silicon Valley is—a lot of people here are the type that just don't really believe that for whatever reason. I do. I can't prove it. I can't—there's no model. We've tried building the attribution frameworks; it's a waste of time. Why do that? But I believe it. And so, yeah, I'm trying to answer your question around changing people's mindsets and mentality and normalizing behaviors around paying creators for their work. I think a lot of it is understanding brand and narrative and storytelling. And then if you don't have the product to back it up, it won't work.

Jackson: (50:25) Right.

Jack: (50:25) But—

Jackson: (50:26) But I think it's maybe not mechanical first. It's like an emotional or a human problem first?

Jack: (50:31) 100%.

Jackson: (50:32) It's possible the answer to this question is embedded in part of what you just said. But my sense is—and it could just be my corner of Twitter and the world—that in a certain part of Silicon Valley and startup land, Patreon is very underrated. Perhaps you feel that, and if so, why?

Jack: (50:49) I would say even dismissed.

Jackson: (50:51) Why do you think that is? I would agree it is. I'll do an on-the-nose example—and I like them, I like the platform—Substack is very in vogue in that world. Patreon is not. Part of that is obviously the content on the platform and who uses it. But it's really interesting to me, and Patreon's quite big, quite successful. So I'm curious.

Jack: (51:14) Yeah. Why is that? Well, let me give you what I think is the real answer, which is a little painful for me to say, but I think it's a big piece of the truth. I think I have to take accountability for that. My vibe is not very Silicon Valley. I don't even think of Silicon Valley people as my people. The way I talk, what I care about—talking about brand and narrative and marketing—it's really in vogue now, but I feel like it's more in vogue to talk about how you're cutting your marketing team to invest in engineering. I feel like that's more the tech vibe, and I don't believe in that. I mean, I understand where that's coming from, but my values, the things that I care about, show up in how the company talks and how the company messages and what I say and what we all say and how we write our blog posts. We very much speak to creators. I know a lot of companies, Substack included, when they speak, the primary lens is reaching tech people. How do we make tech excited about our product? When I'm writing communications to people, I'm not thinking about that at all. I'm not thinking about how do I reach the next hundred engineers as much as I am thinking about how to build trust with creative people and artists. And so I think just 13 years of doing that, people in Silicon Valley just don't care about us as much, which is, I think, very legit. Why would they care about us? We're not talking to them.

Jackson: (53:23) I think there's something to that. Obviously a part of it is that a lot of people in a certain part of Silicon Valley read the types of people who would be more likely to be on Substack than on Patreon. Part of it is just where the audience is, I think.

Jack: (53:39) Yeah, that's a big piece of it too. The media that people author on Substack is about tech, about politics.

Jackson: (53:48) Josh (Citarella) and Recho (Omondi) And these people are not huge on Twitter.

Jack: (53:52) And the people on Patreon are talking about Reckless Ben and the Lego scandal from last year. And those are my people. That's what I want to talk about.

Jackson: (54:01) Ironically, it's actually—but see, here's what's weird. Patreon is more YouTube. Obviously that's like—and there isn't this with YouTube, maybe just because YouTube's so colossal and so big. Although maybe it's also true that the average technology-oriented person or startup person—I think this is actually one of the... do you know the TVPN guys? John and Jordy?

Jack: (54:21) Yeah, I mean, I don't know them, but I know of them.

Jackson: (54:25) I think one of the reasons they were so successful is they took a whole bunch of ideas that were really well-trained on the other parts of the internet and brought them to Twitter.

Jack: (54:32) Yeah.

Jackson: (54:32) But yeah, anyway, it's a—

Jack: (54:34) So this is actually recent with tech on YouTube. Tech was not big on YouTube, right?

Jackson: (54:38) Yeah. Now Founders Fund is playing mafia on YouTube.

Jack: (54:42) But I mean, honestly, I think that the pivotal moment was All-In, which was more of a podcast. But the podcast was the entry point into YouTube and then podcasts exploded in tech and now everybody has a podcast. And that was how tech got onto YouTube. But before that, tech communities didn't really exist on YouTube.

(55:17) Building for Creators First, Incentive Alignment, Trust, 100 Years of Patreon, and Why Jack is the Right CEO for Now

Jackson: (55:04) Yeah. It's also just funny, like Silicon Valley is a place that loves people who are out there and very—don't fit into a box. At least that's the stated preference. And you were very that. But anyway, I don't know if we're going to fully litigate it, but I always thought that was funny. I'm sure there are other examples, but there aren't a ton of easy ones of platforms and big products that really, really ruthlessly prioritize creators over the rest of the audience. And that's not to say you don't—clearly, you guys value Patreon viewers, consumers, fans, whatever, patrons. What has that kind of orientation or principle—how has that shaped the company, particularly over the long run?

Jack: (55:43) It is the shape of the company. Of course we value fans; we have to value fans. If we don't value fans, we can't truly be a creator-first company because a creator's first priority is their fans. So we must value fans, and we have to build the systems and processes and tools and products to help creators reward their fans, think of their fans, prioritize their fans, et cetera. For us as a company, the way I think about it is there are so many great products out there that are an awesome deal for consumers. There's a lot of big, muscly companies that push their weight around and get the consumer what they need. That's great for consumers. We have a lot of options; there's a lot of competition. But there needs to be a big, powerful company that has sharp elbows, that muscles its way around, that makes the world better for creators. If such a company, if such a system does not exist, things are going to keep getting better for consumers, which is asymmetric. That makes things worse. For if you're always optimizing for consumers, then it's always all-you-can-eat. Ten bucks a month, you get as much art as you want. That's not a good economic model for creative people.

Jackson: (56:55) I think that the reason this has been challenging for people to see, even creators, is that most of these other aggregator-style platforms promise creators audience, which is like the ultimate scarcity. And thus it feels like that's obvious. If you want creators, you need to give them audience, which actually means catering to the consumer. And you've kind of inverted that in a way that wasn't obvious.

Jack: (57:18) We've totally inverted it on purpose. It makes it very hard for some people when they get here to think about it from the creator lens because they're used to thinking about it from the consumer lens. They're used to thinking about it as, like, any UGC company—they think of it as a means to an end, which is driving DAU, which creates ad revenue.

Jackson: (57:43) Yes.

Jack: (57:44) And so they're like, "How are we going to get that DAU? Let's spin up a program where we help creators author posts." For us, the creation of the art is the purpose and everything is downstream of that. And so it's a different way to think about the world. And it comes down to the company's KPIs. Our primary KPI is dollars sent to creators. And so that's what we're thinking about. That's what we're talking about. That's not a byproduct of the company; that's the purpose of the company.

Jackson: (58:11) You can almost imagine somebody coming in and saying—maybe there have been examples of this—"We're going to charge half of Patreon's take rate." But in the end, their core incentive is to grow audience. To put it a different way: why do you think Patreon has remained so sticky both for creators, but also for fan and patron cohorts? Ten percent is a big number, to put it a different way.

Jack: (58:46) Yeah, this is one of those things that I'm going to have this sort of spiritual answer for, and then there's maybe the technical answer.

Jackson: (58:57) I'm interested in both.

Jack: (58:59) I think the real answer is the spiritual answer, which is we've done right by creators for 13 years. And that compounds just like anything else. And that compounding trust and understanding from the community has built a lot of goodwill. I'm not saying we don't have detractors. Of course we have detractors. It usually has to do with content policy stuff. When we make a really difficult content policy decision, a lot of people get angry—but we've earned credit.

Jackson: (59:28) You've earned credit.

Jack: (59:29) But we've done right by creative people. A lot of people think of Patreon as the good guys. Certainly a lot of artists and creative people think of Patreon as the good guys. If you're going to run your business on a platform, if you're going to trust that platform with your revenue, with your monthly income stream, with the main thing that you use to build a life for yourself, to pay your mortgage, you're going to go with the platform that you think is the good guys. You're going to go with the platform—

Jackson: (1:00:01) That you trust, or that the creators you admire trust.

Jack: (1:00:04) And so what does that mean tactically? It means that we make long-term decisions founded on trust. I think just more often than other companies do, we don't trade that for a lot. I'm not saying we don't ever have to make decisions where we trade trust. There are sometimes we have to deprecate a product, and that's really hard for the market. And so we have to build mitigation plans and do all those things, but we will often make trades where we trade short-term revenue for long-term trust with our creators and fans. We make those trades all the time. I believe those trades are in the best long-term interest of Patreon's mission and even the shareholders—certainly the creators, certainly the fans. But I want Patreon to be a fucking hundred-year company. I want us to be around, I want us to be fighting for creative people 100 years from now after I'm dead. And I think you can't get there unless you really care about long-term trust. I think about some of my favorite companies. I know everybody in tech is all hot and bothered about Costco. So I'll be one of the people who's hot and bothered about Costco. I think Costco's awesome. Costco kept the price of the hot dog at a buck-fifty for decades. And when Costco got down to the point where they couldn't keep it at $1.50 anymore because their suppliers weren't supplying them at the right prices anymore and they were losing money, they fucking bought a hot dog factory. They made the acquisition, they retooled their whole operation. They figured out a way to keep the price of the hot dog at $1.50. A bunch of people look at that and say that's a terrible business decision. But Costco's like, "We believe that people trusting us is the most important thing. We believe we're fiduciaries for our customers," and—

Jackson: (1:02:01) It's aligned. Critically for Patreon, that's all nice, and it's aligned because you have chosen a business model that makes money when their creators make money.

Jack: (1:02:08) Yeah.

Jackson: (1:02:09) Which I think is an important part. It's not just the values; it's also the incentives.

Jack: (1:02:14) 100%. And that, I wish I could say that was strategic and thoughtful. I think it was just accidental, but maybe there was some intuitive element of that. But yes, having a take-rate model means that all we have to do is help creators make more money. And if we do that, then we make more money. So that business and people incentive means that we don't have to choose between us and creators.

Jackson: (1:02:38) What will actually make Patreon outlive you? What will it take?

Jack: (1:02:45) Ooh, this is a deep question. I think there's a couple things: really great governance, really great culture and values, and then a focus on building long-term trust. Trust, values, culture, governance. If you nail those things, I think a company can last a long, long time.

Jackson: (1:03:18) To maybe invert the question, why are you still the right person to run Patreon now? Why not hire a professional CEO? And by the way, I don't mean a big gray suit. I mean find somebody who's really value-aligned, who has more management experience. You can go make more music, whatever.

Jack: (1:03:38) Totally.

Jackson: (1:03:39) You could be the chairman who goes around and does podcasts more.

Jack: (1:03:42) I have thought about that. In my life, I wasn't like, "I want to be a CEO." That’s not my goal in life. I want to solve this problem. Right now, I think I'm the right person to solve this problem. And I think it's also possible that there will come a moment where I'm like, "Okay, all of the long-term things are in place." The culture is just this snowball rolling down a mountain at a million miles an hour, it has so much momentum. The governance is all in place. All the pieces are there and, honestly, the company doesn't need me anymore; it would benefit from somebody else. I'm not against that. I don't think we're there yet. But how will I know we're there? I mean culture, governance—it's literally those things. I'm pushing to make that happen, not because I don't want the gig anymore, but because I want Patreon to be a hundred-year company.

(1:04:49) Leadership: Types of Ambition, Obsession, Self Reflection, Bias to Action, Learning from Others

Jackson: (1:04:51) In any context—obviously you have more experience in running Patreon and leading bands—what makes a good leader?

Jack: (1:05:01) Oh, boy. Hard lessons over the years here—a lot of pain. I don't know that I'm ready to raise my hand and offer leadership advice to the world on a public podcast. I think there's a lot of things that I've learned and that I'm a lot better at now. I think there's a lot of things I'm still growing and want to get better at. But I have worked with a lot of leaders who I think are really amazing, and I have worked with leaders who I don't trust as much. Maybe I can offer some lessons from that lens. One is: who is the ambition for? Is it for the self or is it for the mission of the company? I like working with really ambitious people, but I want that ambition to be aimed at the mission of the company. When the ambition is aimed at the self, that’s on the denominator of the leadership quality equation.

Jackson: (1:06:05) Is that usually clear within?

Jack: (1:06:08) It's gotten faster and faster for me to pick up on, to the point where I can start to pick it up in the interview process now. Where is the ambition coming from? Sometimes if somebody's really strategic, you cannot pick it up for a little while. So that's one: ambition for the self versus ambition for the company, for the mission. There's some basics like: do you do what you say you're going to do? Do you execute what you promise? Do you deliver what you say you're going to do? That's reliability, dependability—those sorts of things. Not everybody's got that. That's huge.

Jackson: (1:07:02) And somehow the busiest and most effective people in the world are also the most reliable. It's not a coincidence.

Jack: (1:07:11) There's some really important things to me. One is: do you have the passion muscle? What I mean by that is: did you fucking love something before you got to Patreon? Can you fall in love with your customer? Can you go to the ends of the earth to serve someone else, to create value?

Jackson: (1:07:35) Does that passion need to be outside of yourself?

Jack: (1:07:40) Yeah, it's the same thing as the ambition. Is there something external that you can just fall in love with? Call it obsessed, call it passion, call it whatever. Is this a person who gets obsessed with things? That's what I really value about people like Hank Green, who's one of my favorite people in the world. Dude can get obsessed about so many things. I think it makes him really special. Another thing is: can you egolessly self-reflect and do so with humility? That's maybe not important for a lot of other companies, founders, or operators—maybe it is in some capacity—but for me, it's really important. I really want to see a leader who can not only self-reflect egolessly and be like, "I didn't do this well, I'm sorry about that. I want to make sure that doesn't happen again." Not with a bunch of guilt and shame, but with a, "Huh, I'm puppeting this meat sack that did this thing, and this meat sack has now learned that thing and it's going to do better next time." There's an objective ability to do that that some folks have.

Jackson: (1:08:52) A commitment to growth.

Jack: (1:08:55) Totally. I really like to see that in leaders. I've found if somebody doesn't have that, it's very hard for me to work with them. I just lose interest in them, and I lose faith that they can grow and learn into what they need to be, because Patreon is a very weird business.

Jackson: (1:09:20) And I think, as certainly many others have said, trajectory can be a lot more important than current level capacity.

Jack: (1:09:27) Yeah. I'm trying to think of some other things. I mean, there's so much here. I really like somebody—we were talking about Chris Peck earlier—who strips their thinking down to the studs and really tries to deeply understand the unique nature of any context that they're in before just gunning it on solutions. Now, you can overdo that. I've seen people on the other end of that spectrum too, me included, where I'm like, "Got to nail the strategy. Can't take action yet, haven't gotten the strategy in place." Some of the operators I've grown to really love are like, "Next 48 hours, what are we doing? Next 24 hours, what are the next three steps forward?" So much of company building, especially now—nobody knows what it's going to be like in six months. There's a lot of people who say they know what it's going to be like. Nobody fucking knows. And even if they did, I would be unable to tell who knows and who doesn't. So as far as I'm concerned, nobody knows. So, next 48 hours—let's get the right things in place.

Jackson: (1:10:35) But can you cleanly slice that up?

Jack: (1:10:37) Yeah, exactly. Can you take action and generate outcomes consistently? One foot in front of the other. That's been really fun for me. I think if you have clarity over the long term, it affords you the ability to be super focused on execution. If you don't have that clarity over the long term, then you end up switching directions all the time. Having that long-term clarity but then being hyper-focused on the next 48 hours is a unique, bidimensional skill.

Jackson: (1:11:13) You mentioned Hank and Chris Peck. Whether them or otherwise, are there people who have been particularly influential on you via mentorship or whatever else as a leader? Especially given that you're out of the traditional Silicon Valley distribution, though maybe there have been Silicon Valley founders who've been very helpful too.

Jack: (1:11:38) There are attributes of people that I aspire to. I found that if I get too attached to any one individual, I start trying to emulate them, and that is terrible. I can get into a lot of trouble really quickly by over-falling in love with a single individual leader. So what I try to do is—let me think of an example. I don't like everything about Travis Kalanick, but I have seen and heard so many stories about his level of ambition for the mission, and that's really inspiring to me.

Jackson: (1:12:18) Yeah.

Jack: (1:12:19) And so the way I think about it is, can I take—

Jackson: (1:12:20) Just watch a Travis fan edit?

Jack: (1:12:24) I don't have to take the other things. But by the way, I do the same thing with songs. When I'm listening to a song, I'm able to be like, "I really like that lyric," or, "I like this synthesizer," or, "Man, that kick drum just punches through the mix." Or, "That groove—the spacing between the hi-hats and where the snare hits—I want to take that for my next song." I may not like the whole song.

Jackson: (1:12:49) The more youthful person is just going to copy the song or cover the song totally, which—

Jack: (1:12:53) Which I did plenty of in the early days, and it was very hard.

(1:12:59) Talent vs. Enthusiasm, Being Proud of What You Make, Making Fans and Being True, Managing Parasociality, and Community

Jackson: (1:12:57) Sure. There's a lot of learning for that too. A couple things on creativity. What are your thoughts? I'm thinking of sort of—I think you said somewhere you've performed or composed 900 to a thousand songs, roughly. Maybe not composed.

Jack: (1:13:14) Yeah.

Jackson: (1:13:14) So a lot of time in the studio.

Jack: (1:13:16) Yes, a lot of time. I think probably we've published around that. Between Scary Pockets and Pomplamoose and me, we've probably published somewhere around that many songs. Not all that we wrote—a lot of them are covers—but arranged, performed, mixed, mastered, engineered, published. Yes.

Jackson: (1:13:33) Maybe this ties a little bit—and we were talking about the beginning with that as a backdrop. What are your thoughts on talent? Like innate talent.

Jack: (1:13:45) In what capacity? Do I believe in innate talent? Do I believe you can get talent by work? What do you mean when you're thinking about talent?

Jackson: (1:13:54) I guess I'm interested in this idea that you are a very prolific person who clearly has some innate things that are remarkable or unusual, and it could just be energy. Actually, to go back to our first question, clearly you have some baseline amount of musical talent. There's always debates over what made the Beatles the Beatles. Was it the mix of it? Was it John and Paul's innate songwriting ability? Was it all those years in Hamburg? So I guess my question is about—maybe a way to ask this question would be, say you're excited about something. Is excitement enough? Is reps enough? Or do you actually have to really be honest with yourself about what you are and what the world is?

Jack: (1:14:38) Yeah. My instinctual answer to this question—maybe I'll figure it out as I'm talking through it—is I'm not... at least for me, I've never felt talented. I've never felt like I just got that, that it's just embedded in me. I've seen that maybe in other people. My wife can literally sing classical music. She can just write, invent classical music off the top of her head—key changes, modulations. She can just invent. It's unbelievable. I cannot do that. I need to learn theory and learn what chord goes to the B7 and how to resolve to the 1 and then how to modulate to the 5. I have to literally think my way into those things and learn all those things. Even arranging and recording. I was so bad at making music all through grade school and high school. Terrible. I have records of it. I sucked. I remember being in a recording my first time when I learned that there was recording technology—there's a thing called a DAW, the Digital Audio Workstation. I had a Pro Tools Mbox, a successor to the Digi 003 and the Mbox. You could plug your guitar into the Mbox and you could record guitar and it would go onto your computer. This is like early 2000s. And I just thought this was the coolest thing in the world. I was playing guitar on my computer. I had recorded drums and I was playing guitar, and I listened back to it, and I thought the Mbox was broken. I was like, "Oh, there's something with the latency, that's wrong." Then I kept digging in and kept trying it again and kept zooming in and looking. I was like, "Oh my God, I fucking suck."

Jackson: (1:16:27) I just suck at guitar.

Jack: (1:16:31) I'm so bad. So I don't know that I believe—

Jackson: (1:16:33) Have there ever been things where you're just like, "This isn't my thing"? Because from what I can tell, you've done this with animation, you did this with filmmaking, you did this with company building. You seem to just be a wildly persistent person.

Jack: (1:16:46) Is company building my thing? I felt like I was really bad at that for a really long time.

Jackson: (1:16:49) Well, you pushed through. I don't know how good you were then or how good you are now, but clearly you have. There's this strange, interesting essay by this guy Scott Alexander, a rationalist blogger, and he has this essay called "The Lottery of Fascinations." His idea is that you draw a lottery stick when you're born—do you love math or not? Whatever the things you're really obsessed with. My sense is, if you care about something enough, the baseline—and I don't mean to, I'm sure your baseline musical talent is more than what you're describing.

Jack: (1:17:18) That's it. I think you just nailed it. If you care about something enough.

Jackson: (1:17:21) Yeah.

Jack: (1:17:22) All those things that I just mentioned—I cared about those things. There's a type of human that I've met. Our CFO is like this. Watching him build an Excel model—I'm quite confident I will never be able to do what he does with Excel and engineering. I won't be able to do that. Now, you could say, "Well, really, couldn't you spend the time and learn it?" I actually don't think I'm interested enough.

Jackson: (1:17:55) Yes. And that's usually the bottleneck, more so than ability.

Jack: (1:18:00) But there's plenty of things I'm really interested in. I definitely fall in love with a lot of things, and I get obsessed with the process and the behind-the-scenes. I was one of those kids watching DVDs; I always watched the behind-the-scenes. I wanted to see how they made the movie. So with filmmaking or with music or audio engineering or any of those things, I loved the process. I wanted to learn how to do it.

Jackson: (1:18:24) How do you think about—you said there was a phrase somewhere. You said, "Am I proud of what I made?" How do you think about answering that question on a continuing basis?

Jack: (1:18:29) So for me, it's very instinctual. That's literally just like, "Do I love this? Do I feel really good about this?" I think that's an increasingly important question because at this point, the internet has enough stuff. We don't need more stuff on the internet. We need things that people are doing that they are deeply proud of. I'm not interested in putting more stuff on the internet anymore. I actually kind of was eight years ago, but the internet has hit a point of saturation where anything in that realm for me just feels almost wasteful. For me personally—maybe not for other people—but I am just not interested in making something at this point unless I think it's fucking incredible. I want to make something unbelievably great and cool. And if it's not that, I just don't find myself wanting to. I'm just not interested anymore.

Jackson: (1:19:30) Maybe the same answer, but speaking of your business and what you empower creators to do, do you have any advice about making fans?

Jack: (1:19:40) Making fans?

Jackson: (1:19:40) Making people fans of you?

Jack: (1:19:42) Oh, yes. Like building an audience? Building a fanbase, but specifically...

Jackson: (1:19:48) "Audience" feels a little loose. I don't mean an audience; I mean fans.

Jack: (1:19:52) I know what you mean. Yeah.

Jackson: (1:19:53) The people who would pay for a Patreon.

Jack: (1:19:55) Right.

Jackson: (1:19:56) And granted, there's a transaction there, back to our earlier point, but—

Jack: (1:19:59) Right. I do have advice. I think there's a lot. Let me give you some tactical stuff and I'll give you some high-level stuff. A big one is—everybody talks about being authentic or personal brands. I really think it's about... One of my favorite pieces of advice here is Charlie Kaufman. I love Charlie. Just the best. Talk about excellent things; the world needs more things like what he makes.

Jackson: (1:20:29) Strange and wonderful.

Jack: (1:20:31) Just beautiful. Where does that come from in him? He gave a speech, the BAFTA speech.

Jackson: (1:20:40) The best.

Jack: (1:20:41) Oh my God, that talk.

Jackson: (1:20:41) You have to offer something.

Jack: (1:20:48) And what he said is, "Say who you are. Really say it. Say it for the kids who aren't born yet, who won't be born for 500 years. Say the thing you're ashamed of. Say the thing that you think is so awful about yourself that you don't want anyone in the world to know it—and say it." That's really hard to do because it's easy to think you're being authentic. But if you're really saying all of it—and I don't mean oversharing, I don't mean saying everything about yourself, but being true to who you are.

Jackson: (1:21:23) Sort of being true.

Jack: (1:21:32) Being true to who you are. When I think about when I become a fan of somebody—fucking Prince. Oh man, Prince is just like, "Don't like it? Take it or leave it. Fucking go away." I love that. That's what I want to be. That's how I want to spend my time on Earth: "Don't like it? Go away." And a lot of people don't like it.

Jackson: (1:21:54) But the people who like it, oh man, they love it.

Jack: (1:21:59) Yeah. That is so hard to do. And I think that's probably the most important thing. By the way, creators are fucking amazing at this. Companies are terrible at it. Companies are so risk-averse that they can't say who they are in all of their flaws, in all of their idiocy. They can't do it. They want to look too cool for the world. That's one thing. Another thing is tactical: frequency. This can be in tension with quality. But if you publish one thing every three or four years, it's very hard to build a fanbase—unless it's a two-and-a-half-hour movie, then you can publish one thing.

Jackson: (1:22:46) Unless it's a robot music video.

Jack: (1:22:46) Unless it's a robot music video. If you think about the people you love in your life, they're people you talk with and hang with and have interactions with a lot. It's very hard to develop that deep personal relationship with somebody if you don't have some touchpoint with them. I think that's one of the reasons episodic media has gotten so popular over the last decade; people have realized that's a really great way to build a strong relationship with your audience. So, saying who you are and frequently communicating with the people that you're trying to build community with. And then the last thing is just, again, I think it is so important to be proud of the things that you're making. If you don't want to consume the stuff that you're making, it's hard to want other people to consume it too.

Jackson: (1:23:33) On the middle note, do you worry at all about what you could call the broad bucket of parasociality?

Jack: (1:23:43) Why am I less worried about that? I do think it's a real thing. I don't know what the solution is to that. I have a parasocial relationship as a fan with many creators.

Jackson: (1:23:56) Yeah. Although there can be different flavors of it, which maybe is part of the answer.

Jack: (1:24:03) It doesn't—I don't find that it negatively affects me as a fan. I literally have dreams about creators that I follow. I'm talking to them and asking them what they think about the world and our product. I mean, that's kind of crazy.

Jackson: (1:24:19) Yeah, it is.

Jack: (1:24:23) But there is a thing that humanity is doing now that it's never done before, which is the art of one-to-many communication. That was not a thing 25 years ago. It was reserved for a very tiny portion of the populace. Now millions of people are practicing one-to-many communication. I think some element of that new paradigm is going to include feeling personally close to someone that you're not personally close to. It's going to be one of those weird externalities that we're going to have to figure out how to deal with. For some reason, it doesn't bug me as a fan, and so I just spend less time thinking about it. I do spend time thinking about it in the context of Patreon: how to build safe systems, investing in trust and safety, investing in content policy, giving creators control of their communities, and allowing creators to have an extra layer of moderation on top of Patreon's baseline content policy. All those things are important.

Jackson: (1:25:21) Forgive the very vague question, but it's such a blurry word: what does community mean? What does great community look like? Obviously there are so many abstractions of this—community at the Patreon level, community at an individual fan level—but what do you think people are aspirationally getting at when they use that word?

Jack: (1:25:42) The distinction I draw here is between community and audience. "Audience" I think of as a one-way transfer. I show up to the concert, I ingest the show, and I leave. It's broadcasting.

Jackson: (1:25:57) Like watching a concert in a suite or a box.

Jack: (1:26:05) Yeah, it's the broadcast. A lot of people use the word audience and community interchangeably. I think there are some creators who actually build community, like Rhett and Link, Mythical, Hank Green, Vlogbrothers. What does that mean? I don't think it's rocket science. I think there are tactical differences and it comes from a place of values. Interactions that are for the benefit of the audience, non-monetary, and just fun. A lot of creators who are great community builders will do something for charity every year. The creator doesn't make any money from that, but it gives people a sense of maneuvering toward a bigger purpose. That's a really nice feeling of spiritual community.

Jackson: (1:26:52) Also collective effort, momentum. Right.

Jack: (1:26:57) Another example is places where people can individually support each other. In the Vlogbrothers, those community members meet up in bars and have drinks together and hang out together without John and Hank being there.

Jackson: (1:27:12) The horizontal part of the fandom without the vertical. Right, right.

Jack: (1:27:15) The connections between the fandoms.

Jackson: (1:27:16) My dad and I both like the Yankees.

Jack: (1:27:20) At the concert, the creator to me is the only edge. In community, there's edges between the individual fans.

Jackson: (1:27:27) That's hard to do.

Jack: (1:27:29) That's really hard to do. You have to be cooking. You’ve got to be creating the conditions for that as a creator.

Jackson: (1:27:35) Yeah. You can't actually fully engineer it. You have to create the space where it can happen. Right.

Jack: (1:27:40) And then I think it also has to come from a place where there are real values and purpose behind it. Like with the Vlogbrothers, they're building this children's hospital in Sierra Leone. What an amazing effort. It's been years in the making. It's been millions and millions of dollars that the community has raised to do this. It's been frequent updates from John and Hank to the community about Sierra Leone, and everybody has this feeling of shared purpose. We're all in this together. So there are actual things that make a real difference there. Another one is in-person. A lot of creators are leaning into in-person, and I think it's going to be huge over the next few years. That's a big piece of building real community.

(1:28:30) Filmmaking, Labels and Collectives vs Individuals, Breaking Patterns, Creative Intimacy, Music, Patreon's Origin, Persistence, Lucid Dreaming, and Taking Risks

Jackson: (1:28:31) Do you think you'll ever make a film? Like a proper film?

Jack: (1:28:35) Why do you ask that?

Jackson: (1:28:37) That was the most clear thing to me. I didn't watch that much of your old YouTube, but you are as much a filmmaker as you are a musician, in my opinion.

Jack: (1:28:49) That's so funny. Even though I've never made a movie, I think my spike skill set is filmmaking. I think that's what I love the most. I enjoy it a lot. I really want to make a movie someday. I don't know if I ever will, but I really want to.

Jackson: (1:29:10) You're capable of running a company for 15 years and making 100 videos. You don't seem to be someone who is limited by your desire. When you desire to make something, it seems to happen.

Jack: (1:29:27) Boy, it doesn't feel like that. It feels like pushing a boulder up a hill for 10 years, but I know what you mean.

Jackson: (1:29:33) I mean, I guess doing anything totally new is a nudge in that direction if you need one. I think it's very clear on the page.

Jack: (1:29:42) Oh man, I want to make a movie so bad. I love movies. That’s my passion in life.

Jackson: (1:29:47) I enjoyed the reference to Dogme 95 and von Trier. Are there any filmmakers who've been especially influential?

Jack: (1:29:56) The usual suspects. Michel Gondry, probably the most.

Jackson: (1:30:02) Really?

Jack: (1:30:03) Yeah, his music videos. Those ones with Björk and the White Stripes. His use of the camera to tell stories—I've never seen anybody who can think like that. Talk about first principles. He's just like, "How does a shutter work? Great. Let's make that the music video." So, yeah, Michel Gondry. God, I love J.J. Abrams. Just raw storytelling horsepower. That dude is up there. Christopher Nolan. These are going to be uninteresting answers; it's the usual suspects.

Jackson: (1:30:44) Cool. This could be a whole can of worms, and we don't need to spend a ton of time on it, but we live in the era of the individual. There are so many great parts of that, like the creator economy and all this stuff. I'm probably a little biased because I spent some time building this brand, 100 Thieves. Part of what we were trying to do is create a label. You go back throughout history, whether it be bands and labels in music, to what curation and magazines and newspapers are able to do. This idea that there is a collective that can introduce new voices, that the group can be bigger than the individual. It seems like that's going away. There are a few bands—I'm stoked on Geese, although candidly, I prefer Cameron Winter, which is maybe illustrative of the point. Do you have any sense on if there's any world where the pendulum could swing back? It just feels like there are too many things in the way. Again, better individuals than Berry Gordy or whatever.

Jack: (1:31:44) But you're saying swinging back to the collective, to the group, to the band?

Jackson: (1:31:48) Things like bands or labels or whatever. It just seems so hard. It's so much easier to build MrBeast than it is to build a brand or a label or a band. We've seen it. I don't know how many bands are in music now.

Jack: (1:32:06) I have so much to say about this. I think there are two things underlying this. There's a million things, but two big things come to mind for me. The first is one-to-many communication. It turns out the face is a key piece of building a successful channel. Like the YouTube thumbnail: Who is the person? That's the person who is the frontman. That's been tried and true. That's honestly why it was more difficult for companies to break into YouTube and social media initially than it was for creators. Because there was no face, and unless you had a face, you couldn't do it. There's a second reason, which is the economics of creation. The best example of this is the orchestra. In the mid-'40s, every number one hit was recorded by an orchestra. It's like a 40 to 50-piece band. In 2006, 70 years later, zero of the number ones are recorded by an orchestra. That's not just because people stopped loving orchestras, which I don't think is true. People love orchestras. It's the amazing timbral sounds and combinations. People still love the score of Harry Potter and John Williams. Culturally, we love orchestras. Why is it? Well, it's because of an economist, William Baumol, who talked about this. It's the cost of output per unit time to create the thing. For an orchestra, that is through the roof. The language around this is almost awful. It's like, "You can't squeeze margin out of a string quartet." I hate that way of thinking about it. There is a capitalist truth under that that makes my blood boil and makes my skin crawl. It's kind of sad for me, what's happened to the orchestra over the last 70 years.

Jackson: (1:34:09) I was just watching a video about "A Day in the Life." They got half of an orchestra—that was the best they could do—and they doubled it up. Part of this is also just that you're trying to make the thing.

Jack: (1:34:16) You're trying to make the thing. But I think that's a big piece of why it swung to the individual, not the collective. One YouTube channel isn't even enough to feed an individual at this point on ad revenue.

Jackson: (1:34:30) But at the end of the power law—

Jack: (1:34:36) There are examples where it is. And the thing I’m excited about is I think as the internet matures and as the business models of the internet start maturing as well, there will be more revenue saturation there, which will allow collectives to thrive in addition to individuals. One thing I think we are going to start seeing very soon is at least the duo, which is like—

Jackson: (1:34:59) You're a little biased, but that’s okay.

Jack: (1:35:05) I think we’re going to see—let’s put it this way: video creation is now the number one lever for any media company.

Jackson: (1:35:17) Yep, yep.

Jack: (1:35:18) If you make media, making compelling videos is the biggest lever for your company, for your duo, for your art, for your whatever. So the person who does the thing and then the person who makes the videos, I think those people are going to come together and that will be a new type of duo.

Jackson: (1:35:36) Not everybody’s going to be MKBHD. You probably want two people in most of those dynamics.

Jack: (1:35:39) I think we’re going to see that.

Jackson: (1:35:44) That’s cool. A couple of miscellaneous things before we wrap up. Why do you love Revolver so much?

Jack: (1:35:59) I love it because it broke the pattern. I love it because it was outside of the public zeitgeist. And what I mean by that is literally, before that, the way people recorded music and thought about recording music was trying to emulate the sound of a band playing live.

Jackson: (1:36:19) Yeah, yeah.

Jack: (1:36:20) And the Beatles were like, "No, this is a different thing than live." And so they reversed sounds, and they did drum loops on "Tomorrow Never Knows," and they ran their vocals through a Leslie 122, and they did all kinds of things that you couldn’t do live. So you’re never going to replicate that record live. And in fact, they stopped touring after that because they were like, "The record is the thing, not the live."

Jackson: (1:36:44) And who knows? Maybe it actually went the other way. Maybe they made Revolver because they wanted to stop touring.

Jack: (1:36:47) That’s also possible.

Jackson: (1:36:50) Necessity is the mother of invention. It’s interesting because I think you’re right, and everyone always makes this point with—

Jack: (1:36:56) Sgt. Pepper, but they did it way before that.

Jackson: (1:37:00) Yeah. No, I just think it’s interesting that you pick that. As far as I understand—maybe a little on Rubber Soul—but as far as I understand, that was the album where it really started to happen.

Jack: (1:37:08) Yeah. If you listen to Revolver, you can imagine kids just tripping in the '60s being like, "What is this?" Rubber Soul kind of sounds like you’re watching a band play live. It’s a little bit more of that. It’s great songs.

Jackson: (1:37:23) It’s inventive songwriting, right.

Jack: (1:37:24) But Revolver, sonically, from a timbre perspective, from a sonics perspective, there was so much invention there. And for me, it defined recorded music.

Jackson: (1:37:34) How does creativity evolve or change or deepen with intimacy?

Jack: (1:37:43) Well, my firsthand experience of this with my wife, it makes it harder and better. Because I think to do what Charlie Kaufman was talking about—say the thing you’re afraid to say—if there isn’t that intimacy there, it’s very hard to say that with someone else. Whereas if you have that trust and intimacy, you can go out on the edge, you can expand the Overton window, you can step outside of the comfort zone more easily. And that ends up being the stuff that really resonates with other people because they’re like, "Oh, no one’s ever said that before. No one’s ever had the balls to say that before. No one’s ever admitted that about themselves." And that can be really exciting and attractive to hear or listen to or watch an artist engage in.

Jackson: (1:38:31) Yeah, maybe there’s a kind of safety in that dynamic that allows you to do something riskier.

Jack: (1:38:36) Yes.

Jackson: (1:38:38) I like to ask people—we talk about things we regret—I like to ask people what they’re most glad that they did.

Jack: (1:38:49) I’ve never thought about that question before. What am I most glad that I did? Okay, self-serving answer, but I’ll give it anyway. After I finished my robot music video, where I knew I was going to get paid less than 200 bucks in ad revenue and I was feeling really depressed—

Jackson: (1:39:11) By the way, I think it’s up on the shelf. The DVD.

Jack: (1:39:14) That’s it. I sat down at my kitchen table and I sketched out the idea that I wanted for my own personal website, which became Patreon. It took about 14 pieces of printer paper. I did it with a pencil on a Sunday afternoon at about 3:00 PM, and I finished in about two and a half or three hours. 14 pieces of paper. And I felt so dumb sketching this out. I was like, "This is so fucking stupid."

Jackson: (1:39:45) People are going to say the exact opposite. That’s awesome. They'd think, "I felt like a genius."

Jack: (1:39:49) I’m a fucking YouTuber. What am I going to do with these drawings? These stupid fucking drawings. And I literally had to say to myself, "This isn’t going to work. That’s okay." I said it out loud. I was repeating it; it was like a mantra or something: "This isn’t going to work. That’s okay. Draw the next page." I’m really glad I did that. I thought the chance of that turning into anything was idiotic.

Jackson: (1:40:22) There’s probably the lesson there.

Jack: (1:40:24) Yeah.

Jackson: (1:40:25) What do you think you love so much about music?

Jack: (1:40:35) Okay, I’m going to get woo-woo. I don’t know how the world works. I don’t know how consciousness works. I grew up Jewish, but I don’t go to synagogue or anything like that. Music to me feels like the closest thing to something supernatural that I’ve ever known in my life. It feels beyond physics to me. And I think most things are physics.

Jackson: (1:41:12) You're on that side of the aisle.

Jack: (1:41:14) I think it’s mostly physics. I’m not a UFO person. I’m skeptical; extraordinary claims require extraordinary evidence. And then there’s something about music that feels like it comes from somewhere else. Something that isn’t physical space-time. I don’t know how to describe it; it feels in the same realm as consciousness to me. Consciousness is another one of those things where I’m like, "I don’t understand the physics." Obviously, nobody does. It feels aphysical, and music feels like it’s in that space. So for me, that’s just a very interesting place to play in. That’s like a fun, intriguing, uncharted territory. Yeah, it’s fun.

Jackson: (1:42:14) You gave this amazing talk at South by Southwest this year, and there’s a part of it where you’re getting quite emotional, talking about the synthesizer and the orchestras and talkies and silent films and the transition that we may be going through now.

Jack: (1:42:26) Yeah.

Jackson: (1:42:27) You also talked about using Midjourney for the first time a couple years ago and feeling like when you discovered a camera as a kid. One of the points you make in that talk is holding two opposing ideas at once. I would strongly recommend people listen to the whole thing. It’s really amazing. I think one of the salient points you make is that there’s no happily ever after. There’s no end point. It’s this continuous wave. When you feel—this is a little bit related to what we talked about at the top—but on the note of there never being a happily ever after, when you feel like the road is running out, especially creatively, what keeps it burning?

Jack: (1:43:14) I've had that feeling so many times now. I think the real answer is I've just been duped by it before, and I don't want to be Charlie Brown again.

Jackson: (1:43:28) Yeah.

Jack: (1:43:30) I've felt like I'm at the end of my rope and all is lost and I'm depressed and I'm unmotivated and I don't see a path. And then I have a snack and realize I was low blood sugar, and then I feel better. And that might sound stupid, but it's like—I don't know what it's like for other people—for me, emotions have this profound way of convincing me of their permanence, especially negative emotions.

Jackson: (1:44:00) The positive ones are like, "Oh, that's just euphoria." Negative ones? "This is real."

Jack: (1:44:03) Like that's what's underneath everything, and this is the new steady state. I just know that I've been duped so many times. I don't want to be duped again. Yeah.

Jackson: (1:44:20) One last question, which is in the same talk. You're talking about how a creator friend of yours makes the point that art is scarcity, which I think is a beautiful frame. You then reference one of my favorite films, Sing Street, which is an underrated banger.

Jack: (1:44:38) So good.

Jackson: (1:44:39) To quote the older brother in Sing Street, rock and roll is a risk. You risk being ridiculed. It's a similar question, I suppose, to the last one, but how do you remind yourself to take risk?

Jack: (1:44:51) Oh, it's so hard. It's so hard. I'm so naturally risk-averse, and that really makes me pissed. Companies are also so stupidly risk-averse.

Jackson: (1:45:04) The world is risk-averse. We are super under-calibrated.

Jack: (1:45:07) And I know this about myself. I catastrophize. I was listening to your interview with Chris Sacca recently, and one of the things he says about great founders—he's like, "Man, great founders never even consider the downsides. They only think about the upsides." And I was like, I guess I'm not a great founder. My natural state, I know my meter is calibrated way off on risk. And so I have to just zoom out, remind myself that I'm catastrophizing. There is a 1% chance of this thing that I'm nervous about actually happening. And how do I remind myself to do that? Okay, this is a quick story, but it's going to be worth it. I got super into lucid dreaming a couple years ago. Lucid dreaming is the fucking best. If you don't do lucid dreaming, it is transformative.

Jackson: (1:46:09) We're gonna need like a Reddit post or a blog post or something to link to.

Jack: (1:46:12) I made a film about it. Because Nataly and I tried it together for a month, we documented the whole process. It's beautiful. Life-changing. There's a concept in lucid dreaming, which is: how do you know that you're dreaming? Because part of lucid dreaming is recognizing that you're dreaming and then, quote-unquote, waking up in a dream. That's the moment of lucidity. And there's this strange thing that happens. It feels a lot like this right now. And then you go, "I'm dreaming." And then you can literally lift off the chair and float out the ceiling and go explore San Francisco in flight. It's fucking incredible. And it's this real. It's just the most beautiful thing.

Jackson: (1:46:58) I did it one time and I jumped up and started to fly for half a second, and I freaked out and woke up.

Jack: (1:47:03) This is the problem. So there are actually lots of techniques to keep yourself asleep. This challenge of how do you know that you're dreaming? And how do you remind yourself to wake up when you're dreaming? There's a thing that you can do called a reality check. You perform a series of actions. "Can I push my finger through my palm?"

Jackson: (1:47:32) Yeah, yeah, yeah.

Jack: (1:47:33) Do my hands...

Jackson: (1:47:33) Yeah. Reality checks.

Jack: (1:47:34) Reality checks. That's what it is. "Do my hands have six fingers or five fingers? If I hold my breath, can I still breathe?" Which turns out, if you hold your breath in a dream, if you go underwater, you can still breathe.

Jackson: (1:47:46) You're checking—you have to kind of check yourself all the time in real life, right?

Jack: (1:47:49) When you're practicing lucid dreaming in your waking life, you're constantly doing those checks all day. And it's really weird because you have to actually do it.

Jackson: (1:47:55) Okay.

Jack: (1:47:56) All day.

Jackson: (1:48:00) People around the office were like, "Yeah."

Jack: (1:48:02) Jax freaks people out. It really does. Okay, let me cut to the chase here, which is there is a thing that you get to called a dream key. A dream key is when this pattern happens, there's a high probability that I'm dreaming. And if you get good at identifying your dream keys, then you get really good at waking up inside a dream.

Jackson: (1:48:28) Wow.

Jack: (1:48:29) For my dream keys, one was being at my childhood home, another was being with my mother, who's gone. Those were dream keys for me. And the same is true with risk aversion. Anxiety is a risk key for me. It means that I'm gravitating towards something I think is going to go wrong that is probably not going to go wrong. And so I've tried to get really good at embedding those keys into my life. I'm not going to pretend like I'm an expert at it, but some people use meditation for that. For me, it was lucid dreaming. It's like: what are my keys in life that are demonstrations that there's a pattern occurring, that is a negative pattern that I want to get rid of?

Jackson: (1:49:18) It's a reminder to see the water.

Jack: (1:49:20) Remember Jack?

Jackson: (1:49:22) That's all I got.

Jack: (1:49:23) Awesome.

Jackson: (1:49:24) This was great.

Jack: (1:49:24) Thank you for the questions.

52. Jack Conte - Draw the Next Page