Darren [00:00:01]:

Hi, everyone. Welcome to another episode of One of One. I’m your host, Darren Gold, CEO of the Dream Group. My guest today is Jack Conte, co-founder and CEO of Patreon. Over 13 years, Jack has built Patreon into a platform that has paid out more than $10 billion to creators. When Jack was 10 years old, the cool kids wore Nike and Adidas. Jack didn’t. He wore Court Classics from Costco. Not because they were better, because the brand worship simply didn’t make sense to him. That same voice, the one that says this isn’t right, has run through his entire life. Today it fuels his fight to build a platform that truly serves creators in an industry he says plainly is bad for humans. In this conversation, we explore the public stance Jack is taking against industry orthodoxy, the business he has built to reflect them, the inner work that has shaped how he leads, and the choices and trade offs he has made over 13 years. Please enjoy my wonderful conversation with Jack Conte. 

Jack, it’s so great to be here. I’m so glad that we’re in this conversation and thank you for hosting us in your amazing offices. They’re incredible. And no surprise given the creative company that you’re building here at Patreon.

 

Jack [00:01:11]:

Thank you. I’m honored that you asked me to do this.

 

Darren [00:01:14]:

Oh, great. And we’re going to have a great conversation. I wanted to start with something that I’ve. I’ve admired about you, even though we don’t know each other well, which is your willingness and the courage to take some pretty provocative stances with respect to creators, platforms, you know, the industry in general, and be a stand for something better and different. And the thing that most grabbed my attention was this New York Times piece you had last year, which I think was the video, which was, which was brilliant. So I thought I’d ask you to maybe start there. Walk us through the three or four public stances you’ve taken, what they are, why they’re so important to you, why they’re important to Patreon, and maybe we can use that as a jumping off point.

 

Jack [00:02:03]:

Sure, yeah. I mean, the one that you’re talking about is personal for me as a creator, and then important for Patreon as a business too. Yeah. So in this New York Times piece, the basic idea was that we think there’s a better way to build media and community on the Internet and a better way to build algorithms and feeds and community products that don’t just rot people’s brains. And we proposed this framework of solving for creator payments, solving for long term human relationships and connection and human agency as being the way to think about that. So, so yeah, that piece came out in October of last year and we’ll

 

Darren [00:02:47]:

link to that in the show notes, of course.

 

Jack [00:02:48]:

And I mean the basic idea there is, you know, I’ve been investing in the social media platforms as a creator for like two decades now. I started uploading on YouTube in 2007. I’ve been using those platforms for a long time to build a community, build a following, build a business like the creative people that we serve with Patreon. And I’ve watched those platforms just get harder and harder to use as a creator and get worse and worse at compensating creative people for their labor in most cases. Actually, to give YouTube a little bit of credit here, they’ve, they’ve actually seriously invested in that, unlike the rest of the platforms. But even YouTube, I think, you know, when, when TikTok came out, YouTube just went down the short form for you rabbit hole. And the impact that that had to to creators on the Internet was we lost touch with all the people that we’d been and all the communities that we’d been building for decades. It got nearly impossible to reach those people anymore. And I think collectively creators realized, oh wow, we don’t have an audience, we don’t have a customer base. These are YouTube users, these are TikTok users, not fans, not community members. And that’s been a really hard realization and moment for creators over the last three years. I’ve been feeling that personally just with my own bands, Pomplamoose and Scary Pockets, when we make a post, we reach 2% of our audience. So like this isn’t, you know, I guess it’s interesting to think of it as a public stance. I’ve just kind of been saying this for the last five years as I’ve been watching it happen. And then it’s affected the company strategy because what affects, I mean, what affects me as a creator and lots of creators affects Patreon. And so at some point it started to become integral to Patreon’s strategy was how can we help creators solve this problem? How can we help creators not just get paid for their labor, but build better, stronger communities where you can actually reach your fans and where fans don’t have this sense that their mind is being ab tested to oblivion. And that culminated with the New York Times piece. It was just like very, I don’t know, it’s like very personal. It’s not, I mean, I suppose you could say that some element of it is strategic because, you know, it was many years in the making, but it was coming from like a very personal need and a very personal place. So, yeah, I feel like very. Yeah, it’s not, it’s not like a, like a scary thing to do that or it’s like, it just feels like we have to do this. So. Yeah, I don’t know if I answered your question, but that’s where it came from, at least, you know, from my perspective.

 

Darren [00:05:27]:

Yeah, well, I’m interested in the quality in you because there are certainly founders that have. The business they’re creating are really a sort of reflection and a representation of who they are. The willingness to challenge industry orthodoxy is something that I really admire. And I want to understand if that’s been part of who you’ve been for a long time. Did it really just truly emerge out of the fact that you’re a creator? Is there something else there?

 

Jack [00:05:56]:

You know, if we’re gonna go there, I think it’s, I think there’s something that has been there for me for as long as I can remember. Okay, I’ll give you a very specific example of. You know, when I was a kid, I found it confusing and weird that like we all kind of were wearing the same shoes, but if the shoes had a different brand logo on them, you were or weren’t cool. And I remember thinking, that’s ridiculous. Like as a 10 year old and so I knew the cool kids were wearing Nike and Adidas shoes, but I didn’t want to get Nike and Adidas shoes. Cause I thought it was like, I don’t know, I think I thought it was like conforming to this thing that I, that seemed to be illogical. And so I bought my shoes at Costco. I bought Costco, sold Court Classic shoes, and they were half the price and they were really good shoes. And I was like, these are high quality shoes. I’m going to wear these.

 

Darren [00:07:00]:

Yeah.

 

Jack [00:07:01]:

And man, I got made fun of bitterly for wearing Court Classics shoes instead of cool shoes. And I, I, but I kind of, I mean, it was like masochistic. I was kind of like, it kind of was like a point of pride for me.

 

Darren [00:07:15]:

Yeah.

 

Jack [00:07:15]:

And then, yeah, I can, I can remember things like that. You know, then when Pamplemoose started making music, you know, we got outreach from institutions and labels and. But we decided to go the Internet route. You know, we decided to build a fan base on the Internet and use this new tool called YouTube to release our music. And we also decided not to Give up a percentage of our business to anybody as pomplamoose, like we said. No, no, no. We’re gonna, we’re gonna have employees that we pay and that we pay well, but we don’t want some institution to have 20% of Pamplomous. We don’t want that. If we need help, we’ll write a job description, we’ll say what we need help with, we’ll hire that person and we’ll do it that way. And that was like really weird for a band to think of it like that and do that in 2008, but it’s how we wanted to do it. So, no, I guess there’s a piece of it that goes back a long ways for me. And by the way, this is a double edged sword, okay? It is not. I think there is a piece of me that sometimes engages in rebellion for the sake of rebellion and that can get in my way. And so I have to be very careful about thinking about, you know, am I doing this because there’s a really good reason behind it, or am I doing this because there’s a piece of my architecture in my brain that, you know, impulsively pushes me in this direction and I want to make sure it’s not the latter.

 

Darren [00:08:55]:

And are you able to discern between the two?

 

Jack [00:08:57]:

Sometimes if I stop and think about it and if I talk to Stephanie about it and if I really soak in it, that’s Stephanie, who’s my, my, my coach from Trium.

 

Darren [00:09:08]:

Yeah.

 

Jack [00:09:09]:

Then, then, yes. And then, you know, sometimes if I’m moving really fast, I kind of default to fuck the man, which isn’t always helpful.

 

Darren [00:09:19]:

So I’m wondering how this quality, which I love and I imagine many people admire, and yes, it’s got its trade offs that you need to be conscious of. How has it shown up? You founded Patreon 13 years ago, so you’re 13 years in. I’m curious when the moments in time where this impulse, or maybe this measured impulse, if you’re at your best, drove you to make certain decisions, to take a different route that you might otherwise have. Certainly a different route than most people would in our kind of for profit paradigm that we operate into. So I wanted to pull this through line into the founding and the building of Patreon.

 

Jack [00:09:58]:

Let me give you some examples where it helped me. And then let me also give you some examples where it hurt me because I think, you know, I want to look at the whole picture where it helped. I remember. I’ll give you an example in the early days when we were pitching Patreon, what I wanted as a creator was when somebody signed up to pay me 10 bucks a month, I wanted their email address. And I wanted that because none of the other platforms gave me their email address. And I had no assurance from those platforms that, that I would be able to continue to reach this person. And like a business that doesn’t have a deterministic line of communication to its customers, how do you run that business? How is that a durable long term business? And so I wanted the email address. And so we built this product that gave creators the email addresses of everybody that signed up to pay them. And I remember pitching Patreon to investors and a very small portion of investors to their credit understood that. And most investors said, I remember showing that product being in the pitch meeting and the, and the pushback was, hey, you’re, you’re reducing switch costs here. You’re, you’re giving your customers a way to bypass Patreon. And so that’s hurting your business. And if you don’t understand that as an entrepreneur, then you just don’t have like good business acumen. Like, don’t you see how you’re, you’re hurting the business by giving customers a direct line of communication, communication outside the platform. I had never run a business. I had never had a job. I didn’t have a business degree. I didn’t know how to articulate or argue with them on why I thought it was important, but I did know that it was important. And so I stood my ground and we kept it in the product. And that turned out to be like that. You know, that sort of. Maybe that came from some rebelliousness or maybe it just came from because this is something that I really wanted. But either way, it was against the grain. And for whatever reason, in that moment, I had the gumption to do it anyway. And I’m really glad we did because it was like a key differentiator for Patreon for the whole first wave, you know, very much talked about in creator communities and turned out to be like a huge value prop for using Patreon as opposed to the, you know, the payments architecture that these other companies built into their offerings.

 

Darren [00:12:25]:

Yeah.

 

Jack [00:12:27]:

So, you know, that’s the moment where it’s helped, a moment where it’s hurt. When we first built Patreon, the product was actually wrong. We built Patreon not as a per month subscription, but as per release subscription. I wasn’t making videos monthly. I was making videos whenever I wanted and trying to make them as frequently as possible. So we wrote in a little. We had like a little blank. You could fill in a blank in the product and say what you wanted to be paid for per webcomic, per video, per podcast, per drawing, per whatever. And that was the way the product worked. I want to be paid every time I make a drawing. And then you’d submit it as a drawing and then it would run credit cards and you’d be charged whether that was three months later or two weeks later.

 

Darren [00:13:13]:

Yeah.

 

Jack [00:13:14]:

And then one day a creator wrote in, in the blank. Instead of podcasts, they wrote month. I want to be paid per month. And then we started noticing the sign up flow. A lot of creators started writing in the word month.

 

Darren [00:13:29]:

Yeah.

 

Jack [00:13:30]:

And we realized, oh, we got the product wrong. And so we made monthly payments, a checkbox when you signed up, instead of having to hack the product and write in month. And, and now, you know, fast forward 97% or something like that of our, of our dollars sent to creators is monthly subscriptions as opposed to per thing. And so that’s a moment where I think my initial instinct on, like, we’re going to redefine the subscription. Who cares about the like, let’s do it at the pace of the artist. You know, that was just wrong. It’s not what people wanted. And so I learned that the hard way. And we had to correct and make the product change months later.

 

Darren [00:14:07]:

Yeah, yeah. This kind of, this distinction between what people want and what they need I think is a really interesting one. And it’s almost like getting both of those right is the magic. But the first story about the email, I think I just want to come back to because I think it was such a important choice. It turned out to be right. Both right for creators and right for the business, which is the sweet spot. You mentioned Costco. There’s the famous $1.50 hot dog story. Right. They’ve made a series of choices about doing what’s right. Something where they’ve capped their margins. It’s non extractive. And in a lot of your writings and speeches, I’ve noticed this sort of theme of like doing what’s right. What’s essentially the right thing for creators that doesn’t extract, unfairly, value and profit. And as I was getting ready for our conversation, the question that kept coming back to me was there are these handfuls of really admirable companies that have chosen missions that are less extractive, they’re more right in the sense that they claim them to be. And yet there’s this inherent Tension that ultimately you’re sacrificing maximum scale if you do that. So I want to know if you agree with that and how do you reconcile? You’ve got investors on your board, you’ve got employees that are operating in a paradigm of growth at all costs. And essentially what you’re saying is we’ve got to trade some of that off. And I just love to get into that tension that you face and how you’ve built Patreon in light of it.

 

Jack [00:15:40]:

This is a never ending tension. It’ll never go away. There will never be a clear answer. A mistake I made early on was thinking that there was an answer to this question. There is not. There’s just consistent ongoing tension and arguments. And like learning how to navigate that tension and stand up for myself in those arguments is like really important. Different people are on different areas of that like multi dimensional spectrum that you’re like, you know, that you, that you are calling extractive. My general hypothesis and the way that I think about this is power is shifting away from institutions and toward individuals. It has been for many, many years. If you don’t believe me, just look at the Internet. There used to be three channels, three channels of communication essentially from the government to the people. Now there’s literally tens of millions of channels. An individual YouTuber can release an investigative report that gets a hundred times the views of, you know, a mainstream media outlet at this point. So there is something very real with how the power dynamic in society is shifting. This is like the first part of my hypothesis here, which is that the companies that embrace that power dynamic, that embrace the fact that hey, the control, the leverage, the power is shifting to the individual, to the creator. The companies that embrace that, I think are going to build the tools and services for the next era of humanity. The companies that fight that are going to be fighting an uphill battle because that, that paradigm shift is massive and widespread. So that’s the first part is like how can we empower, drive, leverage for give value to creators and individuals? That’s the first thing. The second thing is I do ultimately believe that it and this is the part that’s just like hypothesis, conjecture, whatever you want to call it. I do ultimately believe that what is long term right for the customer is right for the business. If we just keep remembering that, if we just keep remembering do right by creators, do right by fans, then they’re going to keep loving and trusting and using Patreon. And you know, we have been, you know, we’ve been fighting the world’s most powerful, high performing product and engineering shops on the planet. At the same time as they’ve built robust payments roadmaps for their creators, it is not for lack of trying that they have not succeeded. Instagram and TikTok and Facebook, these companies have tried to build Patreon clones over and over and over again. And we recently announced $10 billion paid out to creators. I believe that’s because we have always done right by creative people and Facebook hasn’t. Facebook doesn’t do right by creative people. Facebook builds a product that 6,000 creators use and they’re making a lot of money on it. And then Facebook pulls it in 30 days, gives creators 30 days notice and says good luck. And those creators feel burned. And then they tell the world, Facebook burned me. And that happens 50 times. And then Facebook has trouble driving adoption of their payments products because people don’t trust them. If we’re asking creators to build their communities and their businesses on back of our stack, they’ve got to trust us, which means we have to do right by them. You can’t buy or market your way to trust. Trust is not something that you can get with branding and colors and fonts and iconography and billboards. It comes from making product decisions that do right by your customer base over and over and over again for a decade. And so I believe that if we keep doing that, we’ll keep attracting creators, we’ll keep growing, we’ll keep getting more shots on goal to grow the company and build things and build new products. And all we have to do is keep doing it in a way that is fair to people. So there’s that hypothesis. Not only is power and leveraging control shifting, but I just believe trust is so important. And then the last thing I’ll say about the tension is that where I am on that spectrum, I think is I think just based on my own interaction, I’ve never had another job before. This is my first job. So I admit that I’m lacking an objective reference frame for this. But based on the number of people that I’ve worked with over the years in tech, I think my position on that spectrum is probably further away from the mean than your average tech company. And so what that means is it’s really frustrating for a lot of people to work here who are not in that same place on the spectrum, who don’t share those beliefs about power and control and leverage shifting and that the most important thing is retaining trust over the long term. If you don’t ultimately share those perspectives, it’s going to be very hard for us to get along and we haven’t and it’s caused some breakups. And so that’s been very painful and very hard. But ultimately that’s one area that I’m not willing to sacrifice that, because I just believe, I have too much conviction in those two beliefs.

 

Darren [00:21:31]:

I want to come back to the last point you made around people. If this isn’t right for you, it’s going to be a hard road. Really come back to that. Just parking lot it for a second. And I want to go to the earlier part of your kind of hypothesis that you were articulating. What I’m hearing in all of that is this is a long, it’s got to be a long term game. So you’re going to have some strong counterexamples. And we have trillion dollar plus market cap companies that are proving in the short term, at least if you think about the long arc of history generational company, that that’s a better strategy from a pure kind of profit and market value creation. Is that true? Is it this a implicit in this, that this is a long term play? I think it is. Love your thoughts. And then how do you get the permission to play that long term game? And we can get into it if you want. I mean there’s structural things that you can do and companies have done. But how do you think about the permission that you need to play to play that game? Because I do think it’s going to require a lot of patience, ambassadors and otherwise.

 

Jack [00:22:34]:

Yeah, I don’t know that you get or anyone will give you permission or

 

Darren [00:22:41]:

at least the space to, you know, like not free, you know, they may not be explicit permission, but at least enough freedom to play this out in a way that it requires. And do you have it?

 

Jack [00:22:53]:

Yeah. So again, this is like never ending battle, never ending tension. But where I feel really good now is like the, the board that we’ve built and that we have in 2026, we have a really ambitious vision with this, this idea of building a better network, building a better Internet. Yeah, that’s gonna, that’s gonna take a while.

 

Darren [00:23:18]:

Yeah, yeah.

 

Jack [00:23:19]:

Now fortunately we have this membership business that has steady growth and resilient cohorts and so that’s kind of this amazing fuel for the journey. But yes, our board is psyched about that vision and that mission. Not all of our investors have been over the years and that has created tension and some of those investors have come and gone and I think that’s good. I think it’s Important for everybody to get on the same page about what are we trying to achieve? Let’s get the setup and let’s find the right partners to help us all achieve that. And if you don’t want that, that’s okay. I don’t want to. I think a mistake I made early on was trying to convince everybody else that they want what I want. Sometimes people don’t want what I want and what we’re going to do. And the worst mistakes were when I compromised or tried to meet people halfway and when actually I knew exactly what I wanted and we’re just gonna go do that. And so, yeah, it’s more. It’s less like, at least for me, I found it’s less like permission, and it’s more like, hey, here’s what we’re going to do. If that’s not right for you, I totally understand. Let’s figure out the right path for you then. Because what we’re gonna do is this. And that can be really painful and hard sometimes. I have not always been good at that, by the way. You know. You know, clarity is. Kindness is like. You often hear these types of things when founders are doing podcast interviews. So I hate to sort of revert to that sort of trope, but it’s. The truth is I was not good at that for a long, long time because it’s hard to do that. I want to be a good partner to people. I want. Yeah, I want them to have a good experience with us and with me. And sometimes that’s not always possible. And so it requires just, at the end of the day, being really clear about what it is that we’re doing. It feels more like that than it does like permission.

 

Darren [00:25:26]:

Yeah. And it’s exactly the way I help frame it for the CEOs and founders I work with. I’m really glad you’ve gone here because I’d like to explore this path that you’ve been on. And it sounds like it’s a never ending path.

 

Jack [00:25:37]:

Right.

 

Darren [00:25:37]:

To getting more and more. The word I often use is unapologetic, not in an unkind way, but in a really clear, really distinctive way. I had Mark Pincus, the founder and former CEO of Zynga, on, and he started all of his investor meetings with the top 10 reasons you won’t want to invest in Zynga. And it’s a phenomenal conversation, but it’s a manifestation of that level of clarity. And he didn’t do it with any edge, although he would say it was probably a little edgy. When he was in his 40s, I think that’s exactly what he said. But this notion, and I think it applies both to the culture you’re building here, the strategy and the vision you have, and then the contract you’re entering into with all the people that join and your board. It sounds like you’ve moved into this phase of leadership where you’ve claimed that right to be really clear. And not only the right, but like the responsibility to be clear so that people have the information they need to be completely on board or you know, I’ll take my talents and my money elsewhere. And so I’d love, if that feels like a. I’d love. Is that a fair representation and then walk a little bit through because I think there are people that are listening probably right now saying, and I think very few, I’m already there, but wow, that’s an important distinction and for all sorts of reasons, I’m not there yet. So I’d love you to share that path to help them.

 

Jack [00:27:04]:

That is the story of my last probably four years. And very intentional.

 

Darren [00:27:11]:

Yeah.

 

Jack [00:27:11]:

And very. I mean, I wrote that email and sent it to the board and said, this is the transformation I need to make very specifically and specifically what that transformation is, though I think the way I characterized it was I need to operate less like it’s my job to find the in between path where everyone is happy and instead still listen, still absorb, still hear everyone’s perspective, use it to inform mine, but then develop clarity of my own perspective regardless of anyone else’s, and really soak in that perspective and build internal conviction around it and then go do that. And that was really, really hard for me. I was so bad at that first of all, not bad at it. I just didn’t do it. And it created a lot of pain and problems.

 

Darren [00:28:11]:

And what was it about you that got in the way of doing that?

 

Jack [00:28:15]:

If I’m being really honest? Just the pattern, the psychological pattern of people pleasing, wanting others to be happy, feeling responsible for others emotions, which is coupled then with blaming other people for my emotions, when actually that’s my shit, not theirs. And I don’t know, that’s a hard worldview to pull yourself out of. It feels very real. It feels like this person hurt me, they hurt me, they did something and that was wrong and they need to apologize to me for that. That’s a very real feeling. It feels like reality and I’m not pretending like I’m out of that. I have to constantly remind myself that is not real. And when I can do that. It helps me remember. It’s also not real that I’m responsible for getting in the way of what that person wants. They can go get what they want, however they want to.

 

Darren [00:29:25]:

Yeah. Yeah.

 

Jack [00:29:27]:

And, and so both need to sort of come and, and, and gosh, that journey was a lot of coaching with Stephanie. And, and actually even more than that, a lot of, I mean, you know, opening up here, a lot of therapy. Like, I was unable to do that as a leader until I was able to do that as a person, as a human. And so the sort of, I would say the leadership adjustment was predicated on the personal adjustment. And it takes a while to go through some of that. And I had to do a lot of reading as well. There’s a wonderful book called the Courage to be Disliked, which fantastic book, amazing book. Sort of this wonderful Socratic dialogue, you know, and then, and then there’s another, another book that is just fantastic. These titles are so silly, but it’s called When I Say No, I Feel Guilty. Another great book called the Power of a Positive No. And you know, I had to like, really start soaking in the separation of tasks, owning my own internal state, reminding myself that other people’s internal state was theirs. Not feeling responsible for their internal state. Like I had to go through that. And I’m not even talking about in business, I’m talking about in life. You know, I had to really kind of go through a lot. There’s also wonderful. There’s a wonderful piece, Kegan, I forgot his name, you probably know it. On adult development.

 

Darren [00:30:50]:

Kegan.

 

Jack [00:30:51]:

Kegan.

 

Darren [00:30:51]:

Bob Kegan.

 

Jack [00:30:52]:

Yes.

 

Darren [00:30:52]:

Adult stage development.

 

Jack [00:30:53]:

Oh my God. That. There’s like a 12 page PDF that I think probably changed the course of my life on these stages of the socialized mind.

 

Darren [00:31:03]:

Yeah.

 

Jack [00:31:03]:

Which is kind of what we’re taught as teenagers, how to coordinate and cooperate.

 

Darren [00:31:07]:

My self worth is dependent on what others think of me.

 

Jack [00:31:09]:

Yes.

 

Darren [00:31:10]:

Yeah. Yeah.

 

Jack [00:31:11]:

You know, and then there’s these stages past that that like.

 

Darren [00:31:13]:

Yeah.

 

Jack [00:31:14]:

You can actually kind of get to. And I’m, I’m still working on it. I don’t want to pretend like I’m, I’m, you know, I’ve, I have transcended. I have not. It’s all. It’s a journey.

 

Darren [00:31:25]:

Yeah.

 

Jack [00:31:26]:

But I feel better when I operate in that way and I remember those things. I, I don’t, I don’t feel. Yeah. I don’t feel like I have the weight of everything on my shoulders. And it feels. Yeah, it’s a lot better. And the business runs so much better. When I can really lean into that and remember that.

 

Darren [00:31:42]:

Yeah, that’s what I’m really appreciating about this part of the conversation. I mean, many parts of it. But we oftentimes talk about and you’ll hear the inner game of leadership is so important. But what you’ve done in the last five or 10 minutes is you’ve connected it to a fundamental evolution in your leadership that’s going to have ramifications for a long time. And so I’m really appreciating the level of depth that you’ve gone into. And the connection to this has enabled you to be the leader that has a strong conviction, is unapologetic about articulating it, and invites people in or not. And then the beneficiaries, of course, of that inner work are going to be the people that work here, the creators, the thousands and millions of creators you’re serving. So I’d love. I’m really appreciating that connection.

 

Jack [00:32:29]:

Awesome. Yeah. I mean, that’s been the big thing for me over the last few years, and I would say the most transformational thing for the business is that inner work.

 

Darren [00:32:40]:

Yeah. The business where it sits today. I know you’ve made some changes. They’re all public. Right. You’ve got in many ways this different, vastly different kind of algorithmic discovery engine now, and that’s a part of your business. But I know it’s a shift for you and it’s a shift that probably has some tension with values and the beliefs you hold. But, like, where is Patreon today? Where is it going? You alluded to a different kind of Internet even, like, maybe what’s the bigger vision that you could kind of bring into focus.

 

Jack [00:33:15]:

Yeah. So the big way to think about the change, there’s a couple ways. Essentially what we’ve done is on Patreon previously, you could bring in a community, you could post to that community, you could message people in that community, you could talk to them, but it was siloed. So there were hundreds of thousands of creators on Patreon and tens of millions of fans, but each creator could only communicate with their fans. And so what this meant very specifically was we were solely a monetization platform. If you had a pre existing audience on YouTube, on Facebook, on Instagram, you could bring that audience, a portion of that audience over to Patreon and build a business with those people. If you have a podcast or whatever it is, you could build a business. The change that we made is now you can make a post on Patreon and in addition to just reaching your community, you can reach the millions of fans and hundreds of thousands of creators on Patreon as well. So we added Discovery, basically, and it’s been. We’ve been chipping away at that over the last four years, adding new Discovery tools. But the most recent update is the most significant, which is this new form of posting specifically that goes out to everyone called Equip. And so what it’s made Patreon feel like is now you can, like, you can go through the home screen and you can see all the cool artwork and all the cool creative people that are on there. And you never used to be able to do that, you know, now you have a feed where you can actually go through all that. And so the danger of this and the tension that you’re bringing up is that it sure looks like social media. If you were to just parachute in and look at this, you’d say, like, oh, this is. This is. They’re trying to be Instagram. And so we’ve had to be very, very clear about, like, why are we doing this? What are we trying to do? And it’s not even, why is it different from Instagram, it’s just like, what are we trying to. What do we want? And then let’s really lean into that. And so let me give you an example. On Instagram now, when you make a post. When I make a post as a creator, as Pomplamoose, I make a post on Instagram, it goes out to Instagram, and I reach maybe 1 to 2% of my followers that I’ve spent two decades building on the platform. Decade and a half.

 

Darren [00:35:34]:

Yeah.

 

Jack [00:35:35]:

So Pomplamoose is going on tour right now, and we literally can’t tell our fans that we’re going to play four shows later this year. We can’t get the word out to people who have deliberately said, I want to follow this band. I now can’t tell them we’re going on tour. That is insane. The fact that we’re all just accepting that is. It blows my mind. That is not how it should work. So how should it work? When you have a tour or a new course or a new awesome music video that you just spent a year making and 10 grand, you should be able to send it to the people who signed up to see you. That is a very different type of system than what currently exists on any social media platform. And it’s at the crux of how we want to design things differently. And so when we look forward to the next 10 years. It’s not just about reaching your customers, it’s also about from the fan perspective. Do you use Instagram or TikTok? Do you use those platforms?

 

Darren [00:36:47]:

I deleted both. Yeah, but I did, but I was on them lightly.

 

Jack [00:36:51]:

Why did you delete them?

 

Darren [00:36:53]:

The tension. It was sort of like the impulsive need to pay attention. And I was like, I have too many other important things I want to do in my life. And I say that as a father of three children, one of whom my youngest has a big social media following and he’s making a living and doing that. But for me, yeah, that was why I did it.

 

Jack [00:37:19]:

A lot of people feel that right now, me included. I mean, I didn’t delete Instagram, but I deleted Twitter. I was like, I just don’t, I can’t take this anymore.

 

Darren [00:37:29]:

Yeah. And it’s a shame because it’s a form of. There are aspects of social media. It’s a form of my family text has things and I’m now clumsily on the web looking at things selectively.

 

Jack [00:37:43]:

But yeah, there is something really beautiful and wonderful about the Internet. The ability for humanity to, to not be gatekept. And if you have something to say, you can say it and you can find like minded people in the world who want to hear what you have to say. That is, it’s so easy to forget how cool that is. That didn’t exist 20 years ago.

 

Darren [00:38:12]:

Yeah. Yeah.

 

Jack [00:38:14]:

Well, it’s just started existing 20 years ago. 30 years ago. Not a thing.

 

Darren [00:38:17]:

Yeah,

 

Jack [00:38:20]:

literally you had no way to reach your fellow humans until 30 years ago. The only way was to work your way up the corporate ladder and have somebody think that you’re cool enough to be seen. And then they put you on television, you have to pitch a show. It’s just that was the only way. It was one in a million. And it wasn’t if you had good ideas. And so when, when what people called Web2, when that started coming out and anyone could publish for the first time, there was a time period there where I at least was very excited about how the Internet felt both as a creator and as a consumer. It felt like the sort of promise was coming true around egalitarian distribution and connecting humanity up. And then over the last 10 years, it has taken a turn toward more like what feels like we’re lab rats. We’re the product. My brain stem is getting ab tested every day and they’re finding out what is most effective at driving my impulsive, dark, fear based, engaged, addicted nature. Yeah, I’M not that person. I’m not dark, impulsive, fear based. I’m not. But when I use these products, it’s just, that’s what’s being just pulled out of my eyeballs and it’s, it’s fucking bad for humans. It’s bad for humans and it’s bad for the artists who want to be able to say something and reach other people. I, I am just straight up not willing to believe that this is the best way that art and media and community can exist online. I don’t buy it. There should be a better way to do that. We’re taking a crack at that now. And so the worst thing we could do would be to look at TikTok, to look at Instagram and copy their features and their design. That’d be the worst thing. What I’d rather do is say how can art and media and community exist in a way that gets creators compensated for their labor? That allows creators to truly self express and gives fans a feeling that they’re actually building long term relationships with fandoms and seeing truth and seeing things that actually motivate them, that they’ve chosen to see that they feel excited by, that they want to follow. I think there’s a way to do that. We’re at the beginning of that journey now, but that’s why we’re doing it.

 

Darren [00:40:53]:

So what I’m noticing, and maybe just to test with you, we haven’t talked anything about growth, we haven’t talked about revenue. Right. We haven’t even talked about number of creators. And I’m guessing there’s a reason and I want to just throw out what I’m picking up from you, which is it goes back to this belief, which is if you do what’s right over the long term, you build something special. And I’m hearing is like, that’s the animating force here for you and the company you’re building. And almost an acceptance that whatever growth, whatever scale comes out of that. And of course you’re going to want it to be as big as possible because you have a mission, you want to serve as many and support as many creators as possible is more of a byproduct of that than it is. The primary thing that you’re aiming at is that. Am I, Is that fair?

 

Jack [00:41:44]:

Yeah. I mean we have goals internally, we have objectives, you know, we’ve organized it, people have, you know, okrs and we have meetings where we talk about those. So I don’t want to pretend like those things don’t exist. They do. And they are like a really important organizational factor. But I think what you’re getting at is true, which is, I think at some companies, and again, I don’t know, I’ve not worked at these other companies, but based on what I’ve heard and seen and what it feels like from the outside, I think at some companies the growth is, is actually what they’re solving for at the end of the day. And everything else pivots, including values, in order to achieve that. And that’s not how we don’t operate like that. We still give creators email addresses. The value of we want to empower creative people has not. We’ve never adjusted that in order to achieve a specific goal. And so I think there’s an element of truth to what you said. And it’s very hard to run a company without metrics and dashboards and clarity and objectives and goals on a monthly and annual basis. So we have all of that too, because they’re tools.

 

Darren [00:42:59]:

But isn’t there a part of you that, whether it’s the impulsive part or just the part that really thinks on a first principles basis that even questions that?

 

Jack [00:43:10]:

Yeah, the danger with it, the danger is that

 

Darren [00:43:16]:

because I do, by the way, and I know and I’m still measuring revenue and those things have a place, but it’s almost like what is their place is more of the question.

 

Jack [00:43:28]:

You can over optimize for a specific metric and it can be the wrong thing, not just from a values perspective, but for the business. And so there have been a number of decisions this year where we looked at a metric and we thought, okay, we actually could build this, this and this in order to hit that goal, because we’re behind that goal. But we’re not going to build this, this and this. And not even because it’s against our values, but because it actually would push the business backwards over the long run. And so that would be a dumb decision. And so then you have to wonder, okay, so why do you have, Is the metric what you want or is it something else? And so this is the trouble. It’s like, how do you, you know, sometimes I think of culture as a brain. You know, there’s like a brain at the organization. It’s like a collective brain made up of all these wonderful people who are mission focused and want to help the company achieve what it wants. So how do we all lock hands and say, here’s what we want? And I think it requires a complex understanding of what you want. So it requires what do we want over 10 years? What do we want over five years? What do we want our position in the world to be over the long run? What are we not willing to trade off? How do we think about those values? Because we really want those values. So what are we not willing to trade on and how do we describe those and encode those in our culture? And then what is it that we’re actually trying to achieve this year? Like what, what are we trying to do? What do we want this year? And then how do you encode that with like an English language version of the goal and a key metric for the goal and then maybe some sub metrics too. 

 

And then, you know, how do you sort of build a non polarized, holistic understanding of what do we want? That’s hard. That’s really hard. But, but I’ve also seen what happens if you don’t do that. You can hurt the business by gaming a particular metric. Actually, I think a number of companies do this. At least they hurt their trust with users in the way that they do that. So it’s hard to encode what do we want. But that’s a lot of the work of leadership is clearly articulating, refining, learning from standing up and saying like, oops, we thought we wanted this. That turns out we don’t actually want that. What we want is this thing that’s close to that. But we were wrong. And that’s just constant cycles on that so that people have as much clarity as possible. And there’s never going to be perfect clarity. There’s always going to be some ambiguity. And that’s part of it too.

 

Darren [00:46:07]:

Yeah. And you’re building something that has a lot of complexity to it. Not in a bad sense, just it has nuance, it has subtlety, it has trade offs. It has. And you holding that complexity is obviously important, but you leading an organization knowing that you’re asking them to hold quite a bit of subtlety and nuance and complexity, I imagine is an opportunity and a challenge for you.

 

Jack [00:46:30]:

Yep. Not for everyone. And another one of those things. Yeah, there’s a piece of me that’s like, God, wouldn’t it be great if we just said, you know, the goal is this metric, everybody go, go drive that.

 

Darren [00:46:45]:

Yeah.

 

Jack [00:46:45]:

Which I know some companies operate that way, but then I think the product ends up feeling like brain sewage and I don’t want it to feel like that. I think maybe some of that myopic focus on an, on an outcome has actually is a major contributing factor to why it doesn’t feel nice when you use those products now and why people are quitting.

 

Darren [00:47:09]:

Yeah. I’m curious also. You’re a creator. You’re a creator at heart, creator in your soul. And you’ve wound up being and becoming a CEO. And there are two roles, different roles, obviously. What are the parts of the CEO role that you love that are where you feel kind of in creative flow? Where is it at odds with the thing that kind of animates you? And like, where are you in the big question of being a CEO?

 

Jack [00:47:37]:

Yeah. I have tried to integrate these two sides of me. So it is not CEO mode and artist mode.

 

Darren [00:47:43]:

Yeah.

 

Jack [00:47:43]:

And that’s been part of my, part of my work because there are elements of me that, that fall into each of those categories. One of the things I loved early on building Pomplamoose was like building Pomplamoose’s business. I really like that. How do we keep track of the business? How do we define what matters? How do we grow the business? How do we make sure the business is profitable so that we can still keep making Pomplamoose? And a lot of those instincts and a lot of that interest comes from that piece of my brain. And then there’s another piece of my brain that really loves self expression and saying something in a unique way that’s never been said before and communicating an emotion to another person. And, you know, all the things are wrapped up in being an artist. And. And so I love both of those things. And yeah, I’d say no. Yeah, there’s no crisp path for doing both of them. It. It feels I’ve tried to keep my work and my, you know, my, my creative spirit alive through growing the company. So, you know, coming out with music videos regularly. For seven years, I was flying down to LA once per month on a Friday night, I’d record four songs in one day. On a Saturday with Scary Pockets, four songs in one day. On a Sunday with Pomplamoose. And then we had operations teams that would mix, edit and assemble each of those songs and output one video per week per band. And we did that for seven years. So we built like a workflow and production pipeline around the bands. And it allowed me to be a prolific artist, literally outputting, you know, 100 music videos per year.

 

Darren [00:49:33]:

Wow.

 

Jack [00:49:34]:

While running company. And I could do it in two days a month. You know, flying down to LA on a weekend. It wasn’t quite as simple as that, but that was the framework, you know. And so there were some hacks like that that just worked out. But at the end of the day. Like, each of those bands had an amazing operating team. Both bands were profitable because, you know, we’re getting so many streams on Spotify and had memberships that we were able to pay all the people who were doing the production and everything. The real. The real secret is Pomplamoose is run by Natalie, my wife, who’s an amazing. She’s just amazing. She’s an amazing artist, she’s an amazing human. And so she was able to kind of build Pomplamoose like that and then scary pockets. I have a co founder named Ryan, who’s my best friend in the world, and we love each other. And he’s also just a fearless operator and builder and musician and artist. And so having co founders is really important. I could not. I could not have done it without them. And those teams, you know, they’re very special people. So that’s been helpful. But, you know, it sometimes feels like a little crazy, a little hectic.

 

Darren [00:50:45]:

Yeah. Sounds very full.

 

Jack [00:50:47]:

Yeah.

 

Darren [00:50:47]:

But also it feels like a very vital source of your life and a contribution to what you’re building at Patreon. There’s a congruence and symmetry in how you holding and running your life that feels very powerful.

 

Jack [00:51:00]:

Yeah. I tried stopping at one point.

 

Darren [00:51:03]:

Yeah.

 

Jack [00:51:04]:

Because I was like, this is crazy. Yeah, I can’t do both of these things. That’s before we figured out that workflow hack. It was maybe 20, I don’t know, 16 or something somewhere around there. It was the first couple of years of Patreon and I was like trying to do everything myself, including editing the videos and shooting the videos and concepting the videos. And so, like, I was working at patreon, you know, 9:00am to 10:00pm And I remember, you know, sometimes Natalie would come over to the office, we’d shoot a music video at the office from 11 to 3 and. Wow, just insanity.

 

Darren [00:51:40]:

Yeah.

 

Jack [00:51:41]:

And I could not keep that up. And our head of operations at the time, great, great guy named Tyler Palmer had like a little intervention with me. Was like, this ain’t working. And he was really right. And so I tried stopping Pomploom as we like put Pomploom on hiatus. I did that maybe three years and like. Yeah, you called it like a source of fuel or something. Like, I could not. I was. I can’t not make music. Yeah. I have to make music. So I had to spin it back up.

 

Darren [00:52:18]:

That’s great.

 

Jack [00:52:18]:

Yeah.

 

Darren [00:52:19]:

I wanted to bring us towards a close in the conversation. I think this could go on for a long time. And we’d both be in it. Maybe just to point towards the next four or five years. The last four or five years have been obviously filled with many things, but this part of your leadership, your role as CEO, of becoming unapologetically you, being really clear, fulfilling that responsibility you have, I imagine there’s more work to come. But if we were sitting here four or five years from now and I asked you to look back, what do you think the four or five years would have been spent on in terms of your own leadership?

 

Jack [00:52:58]:

I think that’s not like There are some CEOs, and I’ve seen them and I know about them and I’ve heard about them and I’ve gotten to meet some of them where that comes very naturally to them. I wish I was one of those CEOs, it’d be a lot easier. But that is like a lot of hard work for me. And so the personal journey for me is going to be continuing to really get crisp on. Okay, what do I think? What do I want? What is hearing everybody’s perspectives and opinions, using all that as input, really trying to get curious about what people think and feel because they’re seeing a bunch of things that I’m not. And so making sure that I’m like building a good360 perspective and understanding the trade offs, understanding the risks, understanding the potential for wins, getting really deep on all that and then synthesizing it into, okay, so what do I just know is the right path forward then at that point and remembering to do that and getting really good at that and practicing that. I think that’s my. That is my personal journey, you know. Yeah, it has been for the last two years and I think it’s going to be for the next chapter as well.

 

Darren [00:54:24]:

Given the nature of the world and how quickly it’s changing. That’s a conversation you’re in all the time because I imagine you’re revisiting and revising that point of view, even if there is a constant north star.

 

Jack [00:54:37]:

Totally.

 

Darren [00:54:38]:

So we’ve covered a ton of ground. It’s been amazing conversation so far. I wanted to just give you the spaces or anything maybe we’ve covered. You want to put a finer point on or something that we haven’t that you wanted to make sure we did as we moved to concluding.

 

Jack [00:54:52]:

No, nothing else.

 

Darren [00:54:54]:

Okay. Yeah, it’s been really wonderful. Thank you for being so open, setting such a great example, offering so many great insights and lessons. I really, really appreciate it.

 

Jack [00:55:03]:

Thank you for the great questions. It was fun talking with you.

 

Darren [00:55:12]:

What a wonderful conversation. What stays with me about Jack is the courage of a quieter transformation than the headlines suggest. For most of his life, the instinct that says “this isn’t right” and the need to keep everyone happy were both running him until the two could no longer be reconciled. Jack chose to let go of the people pleasing and the hard sustained inner work of becoming unapologetically himself, no matter the cost to his likability, is a path he is still on. I look forward to being with you on the next episode of one of one. Until then, I hope you live and lead with courage, wisdom and above all, with love.