The Exchanges

Q You mentioned the model there, and you mentioned the business model earlier. A lot of people, as we both know for years, have been saying that journalism could be saved by a rise in micropayments. When we chatted before, though, you said to me, actually, micropayments aren't even a good idea. Can I ask, why do you think that maybe micropayments aren't the solution, and what makes you so bearish?

A I think that micropayments, as we sort of traditionally think of them as like, I'm going to quickly decide whether I want to spend 20 cents unlocking this thing, just don't work on sort of a fundamental product level. I think when you decide to pay for something, there's sort of two components of the pain that come with that. Part of it is like the financial pain of like, I'm parting with this much money, and part of it is just the decision pain of being put to a decision and trying to make a good choice about, do I want to spend on this thing? Do I want to think about spending this? And as the amount of money in a transaction goes down, as it does in a micropayment, you end up in a place where that sort of like decision pain kind of dominates the equation. And so you're like maximizing pain and minimizing the amount of money you're actually getting out the other side. And it just ends up being, it doesn't work. It's not a pleasant experience.

AI assessment note: “micropayments... just don't work on sort of a fundamental product level”

Q And on the flip side, is there anything that didn't work where you're like, actually, we disregarded it when we started Substack and we disregarded it moving forward?

A There's a couple things that I specifically wanted to have different. I mean, one thing, at least for the time that I was there at Kik, we never really had a business model. We sort of had this theory that we're going to build up this big user base, and that's going to be a thing that's ultimately valuable, and that worked for some people, but one of the lovely things about Substack is that we sort of have a business model right out the gate. There's money involved. It's a thing that really works. Another thing that I did differently is that with Kik, we stayed in Waterloo, which is this town an hour outside of Toronto, whereas with Substack, we sort of came to the valley. We came and did YC. We moved here, and I guess time will tell if that pays off, but I'm feeling pretty good about it.

AI assessment note: “at Kik, we never really had a business model”

Q Can I ask, what was the founding story for you then with Substack? Was that the kind of cool takeaway for you, and that translated straight into Substack, and what made that kind of founding moment happen?

A So I left Kik after being there for seven, Plus years under sort of good circumstances, but I was just doing a bunch of different stuff. I was like taking time to live my life and see my friends and family and taking a break. And one of the things I wanted to do on that break was try my head at writing. I've always been an avid reader, and I think that great writing is this tremendously valuable thing because it changes people's minds. It changes how you think about the world. It shapes who you are. And so if you're a writer that's creating, you know, great writing, it's this really high leverage value creating thing to do. I was like, I should write stuff like that. How hard could it be? And I wrote something that I thought of as kind of an essay or a blog post that was basically just bemoaning the state of our current media ecosystem. It was like, hey, you know, the internet came along and made distribution global and instant and free for written content. But at the same time, it like killed all of the existing business models for written culture. And now we live in this weird world where The underlying economic incentives of people's addictive social media feeds is shaping so much of what we read and what we see, and I wrote an essay basically just complaining and bemoaning all this stuff, sends it to my friend Hamish, who's a writer, saying, you know, hey, I wrote this essa…

AI assessment note: “if all of this is true, what would you do about it?”

Q Can I ask, what was the founding story for you then with Substack? Was that the kind of cool takeaway for you, and that translated straight into Substack, and what made that kind of founding moment happen?

A So I left Kik after being there for seven, Plus years under sort of good circumstances, but I was just doing a bunch of different stuff. I was like taking time to live my life and see my friends and family and taking a break. And one of the things I wanted to do on that break was try my head at writing. I've always been an avid reader, and I think that great writing is this tremendously valuable thing because it changes people's minds. It changes how you think about the world. It shapes who you are. And so if you're a writer that's creating, you know, great writing, it's this really high leverage value creating thing to do. I was like, I should write stuff like that. How hard could it be? And I wrote something that I thought of as kind of an essay or a blog post that was basically just bemoaning the state of our current media ecosystem. It was like, hey, you know, the internet came along and made distribution global and instant and free for written content. But at the same time, it like killed all of the existing business models for written culture. And now we live in this weird world where The underlying economic incentives of people's addictive social media feeds is shaping so much of what we read and what we see, and I wrote an essay basically just complaining and bemoaning all this stuff, sends it to my friend Hamish, who's a writer, saying, you know, hey, I wrote this essa…

AI assessment note: “I wrote an essay basically just complaining... sends it to my friend Hamish”

Q And on the flip side, is there anything that didn't work where you're like, actually, we disregarded it when we started Substack and we disregarded it moving forward?

A There's a couple things that I specifically wanted to have different. I mean, one thing, at least for the time that I was there at Kik, we never really had a business model. We sort of had this theory that we're going to build up this big user base, and that's going to be a thing that's ultimately valuable, and that worked for some people, but one of the lovely things about Substack is that we sort of have a business model right out the gate. There's money involved. It's a thing that really works. Another thing that I did differently is that with Kik, we stayed in Waterloo, which is this town an hour outside of Toronto, whereas with Substack, we sort of came to the valley. We came and did YC. We moved here, and I guess time will tell if that pays off, but I'm feeling pretty good about it.

AI assessment note: “There's a couple things that I specifically wanted to have different.”

Q Totally with you there. I mean, speaking of kind of the incentives and the economic incentives for writers there, I've heard you say before the economics of attention specifically have now flipped. What did you mean by this kind of flipping of attention and how have they changed?

A So this is part of my broad thesis is that I remember when I was a kid, when I was young, before we fully had the internet, you could like be bored. You could be sitting at home and be like, I have more attention than I know what to fill it with, and I need diversion. I need entertainment. I need to like, I'm like flipping through daytime TV and there's nothing there. And sometimes since then, with the advent of smartphones and algorithmic feeds and just all of the things we have today, I think we've basically filled that up. You never have to have a moment of your day. There's not a second that you couldn't fill a With some really sort of compelling diversion. You know, you have your phone with you. You can always pull it out. You can always pull out your sort of drug of choice of whatever's good. And you don't have to be bored. You can be on your phone instead. And what that means is that now your attention is actually the last scarce resource, right? You can fill up every second, every sort of possible time you have to spend consuming media. And the only way to improve is not to get more of it. It's to get better. It's to get a higher signal noise ratio. It's to get something that you trust more. And under those circumstances, if you can spend money to get better, higher signal, more valuable, more trustworthy stuff, it's totally rational for you to do that. And so sort of t…

AI assessment note: “now your attention is actually the last scarce resource, right?”

Q mind, I see the juggernauts continuing, be it your Forbes, your Wall Street journals, your major publications, and then you see the rise of the substat creator economy. And everything in between, in my mind, becomes kind of the no man's land. Do you think that's a two binary approach to kind of the future of journalism and the public record? And how do you see that playing out then?

A No, I think that's exactly right. I mean, I think this is the thing you get when the internet creates kind of a global marketplace for things is you want to be the best in the world at something. And that either means being the best in the world by being really good and being the primary thing, you know, you're the New York Times of writing stuff. Or you want to be the best in the world at a very specific thing, and so you want to be the best in the world at being the local paper for this city, or covering this very specific niche, and I think that that's a powerful mode for creating great stuff, and it's not enough to be mediocre and try and make something that's good enough for sort of a medium number of people. You either have to make something that's so good for the masses that it's continues, it's like the best in the world, or that's very good for like a targeted audience. And that's where, obviously, the Substack model is very strong. You know, even if you just, there's a few thousand people in the world that massively value this thing you're creating, you are still creating a lot of value, and this is a model that actually makes that work.

AI assessment note: “No, I think that's exactly right.”

Q How do you find the war for talent today? Everyone always says about the war for talent in the Valley. You said about moving to the Valley kind of permanently, obviously with Substack. How do you find the war for talent?

A I think it's real. I think there's upsides and downsides. I mean, one of the things that I believe about recruiting for a, especially an early stage company that's building something genuinely new is, and it's cliche, but you really do want missionaries and not mercenaries. Like we really want to hire people at Substack that get what we're doing and care about it and value reading and writing and see the vision for the way that we want to change the world. And funnily enough, the war for talent helps that a little bit because the people that don't see and don't care and don't want that stuff, Go somewhere else. They're not going to come work for you. You don't have to worry about somebody coming and joining just because it's a job because they have so many other options. Like you almost get this automatic filter for people who care. It's interesting.

AI assessment note: “I think it's real. I think there's upsides and downsides.”

Q I do want to dive straight in today and really discuss kind of the state of the, maybe the macro landscape. And during COVID, we've seen some of the traditional media publications really hit quite hard. But then on the other hand, we've seen Substack absolutely take off. So a question actually from Seth Bannon was, how do you think about this? And would you say that they're directly correlated?

A I would say they are correlated. And we've been on a pretty good growth trajectory for a bit, but it has certainly accelerated During COVID times, which is very fortunate. I mean, there's a lot of companies that are really struggling in these times, and so it's a privileged position to be in to actually see our growth accelerate, and I think there's sort of two parts to it. One part is sort of a transient effect where all of a sudden people are at home. Some people have more time to write. Some people had this side project they wanted to do for a while, and it's time to do it, or they're looking for more stuff to read, and they're looking for more sort of trusted information, and I think those things are sort of There's a lot of temporary effects that we see, but there's also structural effects. So a lot of the things that are the sort of decline of existing media companies is this trend that's been going on for a long time. That's a big part of the worldview of why we think substacking is an important thing. And COVID has just accelerated that pre-existing trend. And that's something that's not gonna, you're not gonna turn back time on that after that happens.

AI assessment note: “I would say they are correlated.”

Q You mentioned the model there, and you mentioned the business model earlier. A lot of people, as we both know for years, have been saying that journalism could be saved by a rise in micropayments. When we chatted before, though, you said to me, actually, micropayments aren't even a good idea. Can I ask, why do you think that maybe micropayments aren't the solution, and what makes you so bearish?

A I think that micropayments, as we sort of traditionally think of them as like, I'm going to quickly decide whether I want to spend 20 cents unlocking this thing, just don't work on sort of a fundamental product level. I think when you decide to pay for something, there's sort of two components of the pain that come with that. Part of it is like the financial pain of like, I'm parting with this much money, and part of it is just the decision pain of being put to a decision and trying to make a good choice about, do I want to spend on this thing? Do I want to think about spending this? And as the amount of money in a transaction goes down, as it does in a micropayment, you end up in a place where that sort of like decision pain kind of dominates the equation. And so you're like maximizing pain and minimizing the amount of money you're actually getting out the other side. And it just ends up being, it doesn't work. It's not a pleasant experience.

AI assessment note: “decision pain kind of dominates the equation”

Q of creation and the consumption side, incentives are kind of soaking Key to all that we do, both, as I said, on the creator and the consumer side, and when we spoke before, you also said deliberate or not, incentive design really shapes user behavior. You left me on that cliffhanger, Chris, but can you unpack this stream of thought for me, and how do you think about incentive design?

A Yeah, so I think it's basically incentives matter, and you have a system where people are communicating, there's going to be an incentive section, there's going to be things that win, and so you're, let's say, Twitter, and you're designing a Product. And you don't even think about the incentives for the users, but you just think about what's kind of maximizing engagement and what's sort of getting people to come and spend the most time on the site. What you end up doing is you create a set of incentives. There are certain things you can do on Twitter that make you win at Twitter. You know, there are certain types of content that get elevated, that tend to get retweeted, that tend to have a wide reach, that tend to have people talking about them and seeing them. And whatever you reward in that way, that's what you tend to get because you Even if most people within the system don't want clickbait content, let's say, or wouldn't want to create clickbait content, if that's the thing that wins, that's the thing that you'll see more of. And I don't think that that's something that you can fix by sort of patching on some extra rules. Like, if your underlying algorithm is maximizing for engagement, you're not going to be able to, like, turn up the, like, don't make bad content dial in the algorithm and have, like, a permanent fix for that. The only real solution to that is to Sort of p…

AI assessment note: “A large part of what Substack is, is just, what if the game had different rules?”

Q So what's your favorite book and why? I'm sure you've read endless, endless, endless reams. What's your favorite book and why?

A I really don't have a favorite book, but if I'm forced to name one, I think I would name The Death and Life of Great American Cities by Jane Jacobs. I think the reason why I find it so fascinating is because sort of the idea of, like, city craft and what makes a great city has so many parallels in the thoughtful crafting of sort of human ecosystems on the internet, which is a topic that obviously fascinates me. And I just think that the level in that book of, like, kind of practical ideas of, like, if people can see the street, like, that's a good thing, and here's why. Having sort of, like, that object-level idea of what to do And then combining it with kind of an idea of, like, liberty is a force for good is just, it hits me in my sweet spot.

AI assessment note: “if I'm forced to name one, I think I would name The Death and Life”

Q Charles, what do you mean by bundle economics and how do you see that playing out? I'm really interested by that.

A So bundle economics is kind of, okay, if you have a set of publications that are interesting to you, and they all sort of have like their own disparate values, and then they're trying to get as much money as possible from a variety of people, you can construct that in such a way where if you bundle them all together, and the end consumer is sort of like paying for them all at once, kind of like a cable bundle, that it ends up being a win-win for both the consumer and the creator. Because as a consumer, you're paying only a little bit more, and you're getting a lot more access, and then as a creator, you're getting, you know, sort of more money on net from sort of everybody being there, and so there's a real value to being able to bundle things as like, just like a raw sort of surplus for both creators and consumers. The trick is that you have to do it intelligently. You can't come in and impose bundles on people, because then it kills that golden goose of the direct relationship between readers and writers.

AI assessment note: “ends up being a win-win for both the consumer and the creator.”

Q I do want to dive straight in today and really discuss kind of the state of the, maybe the macro landscape. And during COVID, we've seen some of the traditional media publications really hit quite hard. But then on the other hand, we've seen Substack absolutely take off. So a question actually from Seth Bannon was, how do you think about this? And would you say that they're directly correlated?

A I would say they are correlated. And we've been on a pretty good growth trajectory for a bit, but it has certainly accelerated During COVID times, which is very fortunate. I mean, there's a lot of companies that are really struggling in these times, and so it's a privileged position to be in to actually see our growth accelerate, and I think there's sort of two parts to it. One part is sort of a transient effect where all of a sudden people are at home. Some people have more time to write. Some people had this side project they wanted to do for a while, and it's time to do it, or they're looking for more stuff to read, and they're looking for more sort of trusted information, and I think those things are sort of There's a lot of temporary effects that we see, but there's also structural effects. So a lot of the things that are the sort of decline of existing media companies is this trend that's been going on for a long time. That's a big part of the worldview of why we think substacking is an important thing. And COVID has just accelerated that pre-existing trend. And that's something that's not gonna, you're not gonna turn back time on that after that happens.

AI assessment note: “I would say they are correlated. And we've been on a pretty good growth trajectory”

Q Speaking of some of the pre-existing trend, again, I spoke to another of your investors, Emmett, at Twitch For the show, and he asked, given the above happening, and as he said there, the structural changes, the public journal of record though, it has always been free or near free. How do you think Substack interacts with public news, first off?

A I think there's two interesting things. One key thing about the Substack model is even when you go paid, even when you say, I'm going to charge money for this, I'm going to have subscribers bringing me reoccurring revenue, you still get to choose with every piece you publish. Is this going to be only for paying subscribers, or is this going to be free for everybody? And it's actually a core part of the model that you continue to publish stuff for free, and in fact, our emphatic advice to writers is take your best stuff, take your most impactful stuff, and publish that for free. And from a business perspective, that's because that's their top of the funnel. That's where people find out that this is a writer they care about. This is somebody they trust. This is somebody who they're willing to pay to have more of in their life, and so it actually makes the Business side of it work, but it also means that you can have your cake and eat it too as a writer. You can be a public intellectual. You can have sort of a wide impact and far reaching, far traveling public writing, and still have a model that actually works. So I think the Substack model is totally compatible with having sort of a free public record that's widely available and widely traveled. And I think the thing that is perhaps most important about that, and especially when you talk about the public record, is just having s…

AI assessment note: “Substack model is totally compatible with having sort of a free public record”

Q Totally with you there. I mean, speaking of kind of the incentives and the economic incentives for writers there, I've heard you say before the economics of attention specifically have now flipped. What did you mean by this kind of flipping of attention and how have they changed?

A So this is part of my broad thesis is that I remember when I was a kid, when I was young, before we fully had the internet, you could like be bored. You could be sitting at home and be like, I have more attention than I know what to fill it with, and I need diversion. I need entertainment. I need to like, I'm like flipping through daytime TV and there's nothing there. And sometimes since then, with the advent of smartphones and algorithmic feeds and just all of the things we have today, I think we've basically filled that up. You never have to have a moment of your day. There's not a second that you couldn't fill a With some really sort of compelling diversion. You know, you have your phone with you. You can always pull it out. You can always pull out your sort of drug of choice of whatever's good. And you don't have to be bored. You can be on your phone instead. And what that means is that now your attention is actually the last scarce resource, right? You can fill up every second, every sort of possible time you have to spend consuming media. And the only way to improve is not to get more of it. It's to get better. It's to get a higher signal noise ratio. It's to get something that you trust more. And under those circumstances, if you can spend money to get better, higher signal, more valuable, more trustworthy stuff, it's totally rational for you to do that. And so sort of t…

AI assessment note: “now your attention is actually the last scarce resource, right?”

Q of how people think about spending their time. When people think about kind of the libraries of authors and creators that they subscribe to, it's a finite amount. How do you think about the limitations or the maximums that people subscribe to? Because people can't subscribe to 25 sub-stack authors. Where are the limits and what are your lessons on the kind of appetite of attention from the consumer side?

A I think there is likely some limit. There are people who subscribe to 25 sub-stacks. You'll be surprised to know. But I totally agree that for most people, there is some limit there. I think we are before the place where that matters yet. By the time the biggest problem we have is, hey, everybody's already subscribed to five people on Substack and like is struggling to do a sixth. That's a really great place for us to be. First of all, that's a lot of money negativity, but really it's like the amount that we would be as a society spending on funding creation in that world where we're pushing up against that limit is already so much more than we are now. It's so much more like a correct amount where we're paying to have high value culture created that it's good. But once we get there, yeah, it starts to become interesting. Like, do you start to want to have bundling of some sort? Do you want to have some way that writers can sort of self-federate together and sort of help solve that problem? I think, you know, bundle economics are very real. That's definitely a thing that will become interesting. It's just like, feels like a champagne problem from where I sit today.

AI assessment note: “I think there is likely some limit. There are people who subscribe to 25”

Q How do you find the war for talent today? Everyone always says about the war for talent in the Valley. You said about moving to the Valley kind of permanently, obviously with Substack. How do you find the war for talent?

A I think it's real. I think there's upsides and downsides. I mean, one of the things that I believe about recruiting for a, especially an early stage company that's building something genuinely new is, and it's cliche, but you really do want missionaries and not mercenaries. Like we really want to hire people at Substack that get what we're doing and care about it and value reading and writing and see the vision for the way that we want to change the world. And funnily enough, the war for talent helps that a little bit because the people that don't see and don't care and don't want that stuff, Go somewhere else. They're not going to come work for you. You don't have to worry about somebody coming and joining just because it's a job because they have so many other options. Like you almost get this automatic filter for people who care. It's interesting.

AI assessment note: “I think it's real. I think there's upsides and downsides.”

Q I love that. The other kind of often spoken about kind of war is kind of the fundraising war and often on the actual kind of supply side with the competition. How have you found the fundraising journey? And have there been any big takeaways for you from raising for Substack?

A One thing I really valued, and this is maybe this goes back to like advice for CTOs becoming CEOs, I found the Y Combinator, going through Y Combinator, very valuable. And early on, I just sort of like took a lot of their advice fairly wholesale on how to think about fundraising, how to approach it. In general, I'm sort of a believer that it's much better to be a passable fundraiser and as great as you can be at building a successful business than it is to like flip those things and be a great fundraiser and have an okay business. But you still have to be passable and just Being able to plug into the YC knowledge base of just, like, all the basics of how to do this stuff, and I just defaulted to, like, doing what they said. I now recommend people do that unless they have a really compelling reason not to.

AI assessment note: “much better to be a passable fundraiser and as great as you can be at building”

Q mind, I see the juggernauts continuing, be it your Forbes, your Wall Street journals, your major publications, and then you see the rise of the substat creator economy. And everything in between, in my mind, becomes kind of the no man's land. Do you think that's a two binary approach to kind of the future of journalism and the public record? And how do you see that playing out then?

A No, I think that's exactly right. I mean, I think this is the thing you get when the internet creates kind of a global marketplace for things is you want to be the best in the world at something. And that either means being the best in the world by being really good and being the primary thing, you know, you're the New York Times of writing stuff. Or you want to be the best in the world at a very specific thing, and so you want to be the best in the world at being the local paper for this city, or covering this very specific niche, and I think that that's a powerful mode for creating great stuff, and it's not enough to be mediocre and try and make something that's good enough for sort of a medium number of people. You either have to make something that's so good for the masses that it's continues, it's like the best in the world, or that's very good for like a targeted audience. And that's where, obviously, the Substack model is very strong. You know, even if you just, there's a few thousand people in the world that massively value this thing you're creating, you are still creating a lot of value, and this is a model that actually makes that work.

AI assessment note: “No, I think that's exactly right. I mean, I think this is the thing”

Q of creation and the consumption side, incentives are kind of soaking Key to all that we do, both, as I said, on the creator and the consumer side, and when we spoke before, you also said deliberate or not, incentive design really shapes user behavior. You left me on that cliffhanger, Chris, but can you unpack this stream of thought for me, and how do you think about incentive design?

A Yeah, so I think it's basically incentives matter, and you have a system where people are communicating, there's going to be an incentive section, there's going to be things that win, and so you're, let's say, Twitter, and you're designing a Product. And you don't even think about the incentives for the users, but you just think about what's kind of maximizing engagement and what's sort of getting people to come and spend the most time on the site. What you end up doing is you create a set of incentives. There are certain things you can do on Twitter that make you win at Twitter. You know, there are certain types of content that get elevated, that tend to get retweeted, that tend to have a wide reach, that tend to have people talking about them and seeing them. And whatever you reward in that way, that's what you tend to get because you Even if most people within the system don't want clickbait content, let's say, or wouldn't want to create clickbait content, if that's the thing that wins, that's the thing that you'll see more of. And I don't think that that's something that you can fix by sort of patching on some extra rules. Like, if your underlying algorithm is maximizing for engagement, you're not going to be able to, like, turn up the, like, don't make bad content dial in the algorithm and have, like, a permanent fix for that. The only real solution to that is to Sort of p…

AI assessment note: “whatever you reward in that way, that's what you tend to get”

Q Charles, what do you mean by bundle economics and how do you see that playing out? I'm really interested by that.

A So bundle economics is kind of, okay, if you have a set of publications that are interesting to you, and they all sort of have like their own disparate values, and then they're trying to get as much money as possible from a variety of people, you can construct that in such a way where if you bundle them all together, and the end consumer is sort of like paying for them all at once, kind of like a cable bundle, that it ends up being a win-win for both the consumer and the creator. Because as a consumer, you're paying only a little bit more, and you're getting a lot more access, and then as a creator, you're getting, you know, sort of more money on net from sort of everybody being there, and so there's a real value to being able to bundle things as like, just like a raw sort of surplus for both creators and consumers. The trick is that you have to do it intelligently. You can't come in and impose bundles on people, because then it kills that golden goose of the direct relationship between readers and writers.

AI assessment note: “if you bundle them all together... it ends up being a win-win”

Q paradigm that you have today with Substack could extend into so many different areas from marketing technologies, focusing on retention and optimization of Substack pages, Tools, if you wanted to go very long-term to incentivizing creators with insurance products and financial products, even. How do you think about the product paradigm with Substack and where it may be, not ends, but the limits that you want to take it to?

A I'm not sure what the limits are. I feel like there's a big frontier of opportunity for us, and this is sort of what it feels like to be building this company right now, is there are more things that we could start to spend our time diving into and That are seem very exciting and seem potentially like a big deal in creating a lot of value than we can possibly spend our time on. And so a lot of sort of the running of the company is more about an exercise in focus than an exercise in, oh geez, we're sort of like playing against some limits. The place where I see us focusing and the strategy that I see us focusing is starting with making the best possible thing for writers and readers. Making the sort of core substat product For writers who are connecting directly with their audience, and getting paid directly by their audience, and sort of having this long-lasting, high-value, high-trust, renumerative experience, doing everything we can to make that amazing, and then, and only then, sort of expanding from that base into some of the other potential areas of opportunity for the company.

AI assessment note: “I'm not sure what the limits are. I feel like there's a big frontier”

Q Not at all, but I would love to start the show with a little context, and so Substack has become this kind of phenomenon of content over the last year, but how did you make your way into the world of startups, and what was that founding story and aha moment for you with Substack in a brief two to three minutes?

A Well, before Substack, I was a co-founder of Kick, which was a messaging app. I was like the CTO. I started out building some of the original BlackBerry and Android apps, and I sort of grew the engineering team. I was the sort of co-founder and CTO. Grew the engineering team, sort of shifted into product over time. Was there for, I think, almost eight years, actually. I started when I was in third year university, and that was a wild ride, a wild experience. We were in Waterloo, Ontario, Canada. We went from two guys in a dorm room to raising money at a billion dollar valuation to just a whole host of wild things. And I think maybe the biggest thing I took away from it, other than sort of just general learning to do company things the hard way, was the extent to which the tools that we use to interact with each other online, especially when we're communicating, kind of shape the outcomes of that communication and affect the wider culture. So you can't really change human nature. You can't Change what people want, or how they think about the things that you're building for them, but despite not being able to change that, you can change the behavior that gets rewarded, the behavior that ends up flourishing in an online system, and I sort of learned that firsthand at Kik.

AI assessment note: “Well, before Substack, I was a co-founder of Kick, which was a messaging app.”

Q love that in terms of the realization moment, and it takes a true friend to tell you that feedback. I do want to also, you mentioned obviously Kick, and I spoke to Ted before, your co-founder, and he asked in particular, what worked with Kick that you've taken with you to Substack? And on the flip side, what didn't work that you maybe have disregarded and not taken with you?

A I think something that I took from Kik and that I got from probably Ted in particular is a respect for the hard work of building a thoughtful product for people, which sounds kind of, I guess sounds kind of apple pie, but when you want to make something that somebody, a human being is actually going to use and is actually going to integrate in their life and be a way that they're interacting with their friends and their family, the returns on thoughtfulness and putting in the effort to like Figure that out and to empathize with it and to sort of like go from something that's kind of okay to something that's actually usable is very high. And I think getting a lot of that right, mostly to Ted's credit, is a big part of why Kik went through the wild trajectory that it did.

AI assessment note: “something that I took from Kik and that I got from probably Ted”

Q Tell me, what's your superpower and weakness when it comes to company building?

A This may be a little sort of self-aggrandizing, but I, I think of my superpower or the superpower that I aspire to is kind of the respect for both art and science in creating good products and a good company. And so I think of sort of art as the subjective, the design side, the sort of thoughtful, the Empathetic human side of things. And the science as kind of the data and the metrics and the quantitative side of things. And I think that both great products and great companies are necessarily a fusion of both of those and getting those different things to work together in harmony. And it's something that whether or not I'm good at, I'm at least obsessed with getting right.

AI assessment note: “I think of my superpower or the superpower that I aspire to is”

Q My lesson is always invest more than you feel comfortable when it's your friends, actually, because it normally goes right. I do want to finish, though, and the most important, really, what do the next five years hold for you and for Substack? And like, when you think about That vision. Can you paint that for me?

A At the broadest, most grandiose level, I think what we're doing is helping to reinvent the business model for culture. And if you take a step back and kind of think just broadly at sort of a human society scale, how much are we investing in creating great culture and all of the things that come with that? And is that amount like too much, too little, just right? And I believe that it's sort of massively too little and that the ecosystem we have for a Funding creators, and a lot of it is valuing and funding creators, but really the net thing is funding creators in such a way that it causes great work to be done, that it causes, you know, great writing to come into existence that otherwise never would have. It causes sort of scenes and movements to form, and for sort of like the broader project of humanity to improve, it's like we're massively under-investing in that, and in my dream for what we accomplish with Substack is that we're a major booster force for that. We help millions of writers and creators of all sorts have a superior business model, do things professionally when that makes sense for them to do, make it their job to create good culture, and to have sort of like the space and capture the upside of sort of advancing the human project in that way. I think of this like, you know, I had my first son two months ago. A lot of my next five years is Substack and that, and …

AI assessment note: “help millions of writers and creators of all sorts have a superior business model”

Q Not at all, but I would love to start the show with a little context, and so Substack has become this kind of phenomenon of content over the last year, but how did you make your way into the world of startups, and what was that founding story and aha moment for you with Substack in a brief two to three minutes?

A Well, before Substack, I was a co-founder of Kick, which was a messaging app. I was like the CTO. I started out building some of the original BlackBerry and Android apps, and I sort of grew the engineering team. I was the sort of co-founder and CTO. Grew the engineering team, sort of shifted into product over time. Was there for, I think, almost eight years, actually. I started when I was in third year university, and that was a wild ride, a wild experience. We were in Waterloo, Ontario, Canada. We went from two guys in a dorm room to raising money at a billion dollar valuation to just a whole host of wild things. And I think maybe the biggest thing I took away from it, other than sort of just general learning to do company things the hard way, was the extent to which the tools that we use to interact with each other online, especially when we're communicating, kind of shape the outcomes of that communication and affect the wider culture. So you can't really change human nature. You can't Change what people want, or how they think about the things that you're building for them, but despite not being able to change that, you can change the behavior that gets rewarded, the behavior that ends up flourishing in an online system, and I sort of learned that firsthand at Kik.

AI assessment note: “before Substack, I was a co-founder of Kick, which was a messaging app.”