Substack: Chris Best and Hamish McKenzie

Substack was founded to create an escape vehicle for writers: Chris Best and Hamish McKenzie imagined a world where writers didn’t have to rely on legacy publications or corporate advertisers, but could instead create a more direct and meaningful relationship with their audience. Despite early skepticism, Chris and Hamish were confident that many people would pay a few dollars a month to subscribe to their favorite newsletters, on subjects ranging from politics to sports to tech. Today, Substack has over 35 million active users, and while many of its offerings are free, a number of its content-creators make upwards of $500,000 a year. This episode was produced by J. C. Howard, with music by Ramtin Arablouei. Edited by Neva Grant, with research help from Iman Maani. You can follow HIBT on Twitter https://twitter.com/HowIBuiltThis & Instagram https://www.instagram.com/howibuiltthis, and email us at [email protected] mailto:[email protected]. Sign up for Guy's free newsletter at guyraz.com http://guyraz.com/ and on Substack https://guyraz.substack.com/. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Guy Raz?

  Our presenting sponsor today is Anthropic, the team behind Claude. Every founder on this show started with a hard question. Not the marketing plan, the 2 a.m. kind. Is this idea any good? Am I the one to build it? Should I quit my job? Anthropic got built the same way. A public benefit corporation founded on one hard question. How do we make sure AI goes well for people? So they asked over 100,000 people their hopes and their fears and are publishing what they find, even the uncomfortable parts. Me? I've got my own hard question about AI. Here it is. If everyone has access to something that can help them write the business plan,

• 0:46Guy Raz?

  build the prototype, analyze the market, maybe even come up with the idea, what separates the people who actually build something from everyone else? I don't have a clean answer yet, so I've been sitting with it with Claude. There's hope in hard questions. Ask yours at claude.ai/hibt. We get support from U.S. Bank. A question I love asking founders. What's the one decision you almost didn't make? The one that changed everything? Because it's never the obvious stuff. It's never, I decided to start a company. It's the small, boring, Tuesday afternoon decision you barely remember making until you realize it's the reason everything after it either worked or didn't.

• 1:32Guy Raz?

  Say you're 18 months in. Business is growing. You've got expenses coming from six directions. Gas for the van, office supplies, your phone bill, team lunches that are actually client meetings, and you're putting it all on whatever card you grabbed in year one. You're not thinking about it. Why would you? You've got bigger problems. But here's the thing. Path A, you keep going like that. End of the year, you're sorting through statements, trying to figure out what went where. You've left hundreds, maybe thousands, on the table in rewards you never earned, money that could have gone back into the business. Path B, you pause and get the US Bank Triple Cash Rewards Visa Business Card. Now, you're earning 3% cash back

• 2:16Guy Raz?

  on gas and EV charging, office supply stores, cellphone service, and restaurants. You pick up an extra $750 cash back as a bonus. And you've got a low APR on purchases and balance transfers for 12 months while you're scaling. Same business, same expenses, two completely different outcomes based on one small decision. Visit usbank.com/business to learn more. The creditor and issuer of this card is US Bank National Association, pursuant to a license from Visa USA, Inc. Some restrictions apply. If you travel often, you'll want to hear about this unprecedented offer. For the first time ever,

• 3:00Guy Raz?

  new Delta SkyMiles Reserve American Express Card members can earn two Delta Comfort Round Trip flights for travel within the 48 contiguous US states, Puerto Rico, or the US Virgin Islands. Plus, you can earn 50,000 bonus miles towards your next getaway. And who doesn't appreciate an elevated airport experience? Delta SkyMiles Reserve Card members get access to the Delta Sky Club, your pre-flight oasis to recharge, with 15 visits and four one-time guest passes each medallion year when flying Delta together. That's up to $950 in annual value. Value estimate based on $50 per visit rate to purchase additional visits

• 3:45Guy Raz?

  or bring a guest to the Delta Sky Club. Make every trip feel more rewarding with the car that upgrades your travel. Apply today at delta.com/cardsocial. Offer ends November 4, 2026. Minimum spending requirements and terms apply. Flights are fulfilled as flight certificates valid for Delta Comfort or Delta Maine to select domestic destinations. Book 21-plus days in advance. Up to $80 per person and taxes and fees apply. Other restrictions apply. When I pull up to a gas pump to fill my car, I'm not thinking about chemistry or engineering. I'm thinking about getting in, filling up, and getting on with my day. And it reminds me a little bit of the founders I talk to on this show, because the best

• 4:27Guy Raz?

  ones obsess over things their customers will never see. Tiny details, invisible improvements, relentless iteration. And not because anyone's watching, but because it makes the product better. That's what the mobile brand does. It engineers fuel the same way great founders engineer their products. Mobile Supreme Plus Premium Gas helps keep engines three times cleaner, which can mean better performance and improved gas mileage. It's for people who care about what's under the hood, even if they never see it. Three times cleaner compared to mobile regular gas in port fuel-injected engines. Actual results may vary. Visit mobilefuels.com for details.

• 5:20Speaker 01

  It was kind of like, it was a good idea for a company and a bad idea for an essay. Like, you could tell people this thing, and they would give you a blank stare. I would tell people in my life, "Hey, we're gonna make this platform that's gonna, you're gonna pay for writers on the internet that you really like." And they would look at me like I had horns. Or they would take pity on me. They would say like, "Oh, that's, that's so nice. That would be so cool if that worked." But, you know, and I'm sorry to be the one to have to tell you this, you idiot, but like, nobody's ever gonna pay for something on the internet.

• 5:58Guy Raz?

  Welcome to How I Built This, a show about innovators, entrepreneurs, idealists, and the stories behind the movements they built.

• 6:09Guy Raz?

  I'm Guy Raz, and on the show today, how two partners built a getaway vehicle for journalists called Substack, a platform where writers could connect directly with their readers and write pretty much what they wanted.

• 6:27Guy Raz?

  Back when I started out as a reporter, and this is the late 1990s, the idea that some random person with a laptop could reach more people than the New York Times or CNN was absurd. At the time, most people got their information from mainstream sources and a little bit from the internet. Now, these days, the average evening newscast on CNN gets around half a million viewers, half a million people. And yet, there are 140,000 YouTubers with audiences at least as big. Once mighty newspapers, radio news magazines, and TV broadcasts have largely lost their influence and power.

• 7:10Guy Raz?

  And while this isn't a news story, these products have been pushed aside by podcasts, the aforementioned YouTube channels, social media feeds, Twitch streams, and something that's grown a lot in recent years: Substack. It was founded in 2017 by Chris Best and Hamish McKenzie. At the time, Chris was a tech entrepreneur who had left a once-promising startup that would eventually fade away. Hamish was a journalist who wrote mainly about tech and culture for different websites. They had a hunch that people would pay to read the writing of specific writers. But at the beginning, most people were skeptical, understandably because newspapers and magazines

• 7:54Guy Raz?

  were hemorrhaging paying subscribers. What Chris and Hamish were offering was a platform that would make it easy to basically run a small publishing business. With almost no technical skills, anyone could write an article, insert photos and videos, Publish it to the internet, manage a mailing list, and accept payments all in one place. Slowly, they started to attract writers. First, a few obscure ones, and eventually, some pretty heavy hitters like Andrew Sullivan and Matt Taibbi. The business model is pretty straightforward. The writer can charge a monthly subscription fee, usually five to eight bucks, and Substack takes around 10%.

• 8:37Guy Raz?

  Now, today, it's estimated that more than 50 Substack writers earn over half a million dollars a year from paying subscribers. And recently, Substack announced that it has about 5 million total paid subscriptions. For some journalists who used to work for big publications, Substack has become a lifeline. But the company has also taken a pretty strong position on free speech. It means that with a few exceptions, like calls for violence, or pornography, or spam, Substack will let you write basically whatever you want. And the founders have big ambitions for what they expect Substack to become in the future. In a few minutes, you'll hear from Hamish, the other founder, but first to Chris Best,

• 9:22Guy Raz?

  who grew up in the suburbs of Vancouver in the 1990s and early 2000s. Chris got his degree in engineering at the University of Waterloo in Canada.

• 9:32Speaker 01

  The most important thing about Waterloo, though, is not actually what you learn in the classes, it's the fact that they have this mandatory co-op program. You basically go to school for four months, then go and work at a job for four months.

• 9:42Guy Raz?

  Oh, so what kind of jobs would you do?

• 9:45Speaker 01

  Oh, I mean, my first one, I was working in a bearing factory in Stratford, Ontario.

• 9:50Guy Raz?

  Like ball bearings?

• 9:51Speaker 01

  Ball bearings.

• 9:52Guy Raz?

  Oh, yeah, that's serious engineering right there.

• 9:56Speaker 01

  Yeah, I mean, I wasn't doing the serious part. I was doing the little programming and honestly, being pretty useless. But, I mean, I learned a lot. I learned that I didn't want to work in a ball bearing factory in Stratford, Ontario.

• 10:06Guy Raz?

  Fair enough, yeah.

• 10:09Guy Raz?

  All right, so you're, you are doing this program. And, and while you're there, there's a, I guess you meet this guy named Ted Littingston.

• 10:16Speaker 01

  Yep.

• 10:17Guy Raz?

  Who's like a roommate, or he becomes a friend. And he's somebody, I guess, you start to talk with about maybe coming like a cool idea. Tell me, tell me about this, these conversations you guys start to have.

• 10:28Speaker 01

  Yeah, it wasn't very serious at first at all. It started out just kind of as like a project. It was like, hey, let's, let's build some stuff. Let's hack on some things. We were building, you know, the original thing we started working on was a music player for the BlackBerry. I don't know if you remember that, the phones with the keyboards.

• 10:44Guy Raz?

  Everybody remembers what BlackBerrys were, of course. I had one. So, and it was, of course, a Canadian company. So you guys originally had this idea to build an app for the BlackBerry that was like a music app?

• 10:57Speaker 01

  Yeah, we were building a music, we actually built a music app. We were like, hey, we'll go in and make this thing that's way better.

• 11:03Guy Raz?

  Way better than what?

• 11:05Speaker 01

  The, the insight that we had, which sounds very stupid to say out loud now, but was novel enough at the time was, hey, this new device, the smartphone, which for a while, it was basically only like, you know, bankers on Wall Street that had BlackBerrys. And this was gonna, like, the smartphone was gonna take over. This is the new center of your life. And so the idea that you have your music collection on your computer and then sync it to your phone is the dumbest thing ever. You should be able to stream any song you want at any time. So it's like way better than like syncing your music from the

• 11:39Guy Raz?

  Oh, I see, okay.

• 11:40Speaker 01

  Computer.

• 11:41Guy Raz?

  Right. And it was supposed to be a way for people to share music legally?

• 11:45Speaker 01

  It was, yeah, it was basically Spotify. It was basically like an early version of Spotify.

• 11:49Guy Raz?

  Okay.

• 11:49Speaker 01

  And we got stuck in negotiations with the record labels, like Universal and stuff.

• 11:55Guy Raz?

  Yeah.

• 11:56Speaker 01

  And that we, I think we were sort of just like, ah, we'll get there, we'll get there. And then while we were basically waiting for that, we ended up making a messenger on the side.

• 12:06Guy Raz?

  A messaging app?

• 12:07Speaker 01

  A messaging app. We're like, what else can we do? What else are these smartphones gonna matter for? And, you know, BBM Messenger had been a huge deal at the time. And so we built a messaging app that would pair with the music app. So we built, we built this messaging app almost as like a, you know, an accompaniment while we were sort of waiting for these record deals to come through. And that thing blew up.

• 12:31Guy Raz?

  Huh.

• 12:32Speaker 01

  It hit at just the right time and went totally insane. And we went through a period of Sort of surprise, crazy growth.

• 12:42Guy Raz?

  And just to be clear, I think it was similar, a little bit similar to WhatsApp, right?

• 12:45Speaker 01

  It was very similar to WhatsApp. We were basically WhatsApp before WhatsApp.

• 12:48Guy Raz?

  This is, I think this is called Kik, right? You call it, it's called Kik Interactive and the app is called the Kik Messenger app.

• 12:55Speaker 01

  K I K, yeah.

• 12:56Guy Raz?

  And, and so you were essentially the CTO and the co-founder of this thing. And I guess Ted was also a co-founder or the founder too.

• 13:06Speaker 01

  Yeah.

• 13:07Guy Raz?

  And he, and the CEO, and he kind of oversaw like the fundraising and that, sort of the business side of it.

• 13:16Speaker 01

  All the fundraising, all the business side. And to be honest, it was really his vision. He, he sort of had a strong sense of what the product he wanted to bring into the world. And he was driving, driving a lot of it.

• 13:29Guy Raz?

  And so between 2010 and 2015, I mean, you guys had start, I mean, you're getting investors coming at you. This was the hottest messenger app. By, by 2015, it was valued at over a billion dollars. You had 100 employees. It was, this is no joke. I mean, this is, I think there might be people who are listening who remember Kik.

• 13:51Speaker 01

  Yeah. I mean, at one point, there was, I think 40% of you as teenagers were using Kik for a few years.

• 13:56Guy Raz?

  It's amazing. I mean, it had 90 million users by 2013. And I mean, this was bigger than the BlackBerry Messenger, which had 60 million users. They would eventually sue you guys, claiming there was patent infringement on that, you know, and eventually you guys settled with them.

• 14:12Speaker 01

  That happened pretty early. So the story actually went, so this blows up. We can't believe it. I'm like, I don't appreciate it at the time because I'm not sleeping because I'm trying to keep the servers up. And it's just like crazy. But then the people at BlackBerry noticed the traffic. A substantial fraction of all pushes going to BlackBerrys were just messages for our service. And at the time, they, they felt that they had a real strategic, a defensible strategic thing in BlackBerry Messenger, which is basically like their version of like the Apple Messages app. And they flipped on a dime. They went from kind of supporting us and thinking we were cute and fun to saying, No, we're gonna kill these guys.

• 14:55Speaker 01

  And they, they, I got a stack of papers like this alleging all kinds of insane patent infringement, like on stuff that was just completely bogus, but just, you know, they just, you're a couple of people in a startup and they send you this huge stack of papers. But more importantly than that even, they kicked us out of the BlackBerry App Store. They said, you actually can't have an app on BlackBerry anymore. And they, we're gonna turn off your push.

• 15:21Guy Raz?

  Wow.

• 15:21Speaker 01

  So now the people who already have the app, they're not gonna get their messages on time. And if you're a messaging app and your big drive is you're half on BlackBerry and half on iPhone, if you lose half your users, you don't actually lose half your users, you lose like 95% of your users. Because the whole point of the thing kinda goes away. Meanwhile, there's this little other cross-platform messaging app called WhatsApp that kind of like trucks along through this phase and they kind of go on to build like an awesome, amazing thing that, you know, sold for $20 billion or something.

• 15:57Guy Raz?

  Yeah, by, by Facebook. And, and by, by 2015, I mean, I, I actually, I think you guys had like two, over 250 million users. I mean, massive.

• 16:06Speaker 01

  So we, it went, went almost, went up to a million users, almost back down to almost zero, but we did, we built it back up, uh, from almost nothing to get very big again.

• 16:16Guy Raz?

  And, and essentially, the great good fortune was that BlackBerry started just declining very rapidly and iPhones, of course, just, you know, made them obsolete.

• 16:27Speaker 01

  Yeah, it turned out in the long run, the BlackBerry didn't actually, didn't actually matter.

• 16:30Guy Raz?

  And, and this was a, again, a major app. It's almost impossible to believe that something with almost 300 million users doesn't exist anymore today.

• 16:41Speaker 01

  Yeah.

• 16:43Guy Raz?

  Um, but you're there grinding away and by 2017, I guess you decide you're done. You, you're maybe burned out and you wanna, you wanna go. Tell me what, what was going on?

• 16:58Speaker 01

  I mean, I'd been there for, I guess, eight or eight-ish years, you know, after we sort of had this, this BlackBerry thing, we had this messenger that was growing. And we, but we never really figured out what's the business model for this thing? What are we going to turn it into? Like, what does this thing become? And we eventually made the decision to launch like an early crypto thing.

• 17:22Guy Raz?

  A cryptocurrency in part to raise money?

• 17:26Speaker 01

  In part to raise money and in part, kind of like as a, in answer to the question, what do you do if you have a very popular messenger that lots of people use, but you don't know how to make money from it?

• 17:39Guy Raz?

  Right, you weren't making money, it was a free app, yeah.

• 17:40Speaker 01

  It was a free app.

• 17:41Guy Raz?

  So you're thinking, well, let's, let's use it, let's start a cryptocurrency, because we've got the hundreds of millions of people using it, so maybe they'll, they'll buy it.

• 17:49Speaker 01

  Yeah, but I didn't, that wasn't what I wanted to work on.

• 17:53Guy Raz?

  Yeah.

• 17:54Speaker 01

  It had been, you know, I'd been there for a long time, and so I left.

• 17:58Guy Raz?

  Were you able to personally make any money from, from the company? I mean, you had investors, were you able to, to take some money off the table?

• 18:07Speaker 01

  I made some money. And it was enough that it changed my relationship with money, I would say, from somebody that never, you know, was always kind of like scrabbling by to figure out how I'm going to like pay rent to, hey, I've got kind of like some room, room to maneuver. It was definitely not like set-for-life money. And it was definitely not, I think, what some people imagine from a company of that scale.

• 18:32Guy Raz?

  Right, okay, so you are, let's pause here for a moment, because this is where, you know, eventually we'll circle back and with, with Hamish. Hamish, I want to bring you in and ask you a little bit about you, about your life before you and Chris met. I know you grew up in a small town in New Zealand, right?

• 18:53Speaker 02

  Yeah, that's right, it's called Alexandra, 5,000 people. The nearest town that anyone's ever heard of is called Queenstown, which is kind of thought of as the adventure capital of the world.

• 19:04Guy Raz?

  Got it. I know that eventually you, you went to university and you wound up getting a master's degree in journalism. And pretty soon after, I think you started your career, you, you moved to Hong Kong and started working there as a writer. Tell me about how that happened, what did you do?

• 19:24Speaker 02

  I did end up going to Hong Kong and my logic was this was 2006 and China was on the march, China was on the rise, the Beijing Games were two years away and I thought I could go to Hong Kong, learn Chinese and report on the rise of China as a foreign correspondent.

• 19:41Guy Raz?

  Smart move. I mean, it could have been great.

• 19:44Speaker 02

  Yeah, it didn't really work out like that. Instead, I ended up, I just had money, I had enough money in my bank account to last a month there. But I did find a job after trying in a bunch of places and the job was writing for this freebie entertainment magazine, sort of writing about the bar scene and writing about pop culture in Hong Kong.

• 20:04Guy Raz?

  And I guess, and that magazine was called Digital Media and then I guess

• 20:08Speaker 02

  Yes, that's right, yeah.

• 20:09Guy Raz?

  By 2008, you, I think you helped to launch Time Out's version in Hong Kong.

• 20:16Speaker 02

  Yeah, my friend got deeply familiar with my work and then he got tapped to be the editor of this, of Time Out Hong Kong, which we were about to launch. This Time Out in London had been around for 40 years, Time Out New York. And so he liked my work and asked me to come in and be the music editor, basically, at the start and later moved on to other things.

• 20:37Guy Raz?

  So this really is kind of like, I mean, you're still young, right? You're still in your, you know, late twenties at this point, but, but working in like music entertainment, like music and entertainment journalism, right? Because Time Out's more about culture, it's like what's, what's on, what's going on, nightlife.

• 20:53Speaker 02

  That's right. That's right. I did get to also be the online editor in the, in the days when people thought of the web as a separate kind of entity from the magazine.

• 21:02Guy Raz?

  Right.

• 21:03Speaker 02

  And I got, and then became the features editor as well. And as a features editor, I also reported. And so I got to write big sort of think piece-y culture pieces, like what's the difference between an expat and an immigrant? That was one of my big pieces.

• 21:15Guy Raz?

  Right.

• 21:16Speaker 02

  And as an online editor, I got this exposure to what it's like to build a website, especially one that is oriented around listing everything that's going on in the city, which was quickly to become obsolete as the smartphone apps took over.

• 21:31Guy Raz?

  All right. So you, you stay there for a couple of years and 2010, you leave, you move to the United States. Why and where did you go?

• 21:45Speaker 02

  Leading up to the last year of my time in Hong Kong, I started a relationship with an American girl who lived in the Washington DC area. And her name is Steph, she's now my wife. But Steph got into law school and was most interested in this law school at University of Maryland, which has its campus in downtown Baltimore. And so we moved there and I just thought of it as another interesting adventure.

• 22:12Guy Raz?

  Around 2012, you started working for the tech blog Pando Daily. And one of the things you start to cover is Tesla and SpaceX. And I guess like this kind of catches the eye of an editor at Faber and Faber. And they said, hey, do you want to write a book about Elon Musk?

• 22:33Speaker 02

  Yeah, this is 2012, 2013, where people in Silicon Valley sort of knew about this guy Elon Musk, but he hadn't become an outside phenomenon yet. The Model S had come out and won Car of the Year in 2012. And they also created this thing called the Supercharger, which would allow you to charge up your electric car for free. Yeah, and fast, and it could be powered by sunlight. And I was saying, why aren't more people hyped about this guy who's managed to land these rockets? Or sorry, was making these successful launches and was on the way to figuring out how to land them. And had created these amazing electric cars that were winning Best Car of the Year award and could run on nothing but clean energy. And so I wrote a bit about those things and this editor in the UK, Julian Loos is his name.

• 23:19Speaker 02

  He's like, you think there's a way to do a good book about this guy? And do you think you could get him to cooperate? And I was kind of working out of my spare bedroom in boxer shorts in Baltimore. And I thought, yeah, let me, let me see if I can do that. And so I got in touch with Elon through his mother's website. She's a nutritionist, had listed her email address there. And it led to a conversation with Elon, who I actually knew already had liked one of the pieces I'd written because his PR person had told me he liked that piece. And so I thought, oh, maybe I have a shot of getting his attention. And he ended up on this phone call with me.

• 23:53Guy Raz?

  You got a call with him asking if he would cooperate for a biography?

• 23:57Speaker 02

  That's right. I was pitching him the idea of this book. But Elon said, I don't know about the book, um, maybe, but would you be interested in a job at Tesla? And I thought, oh, that sounds like an insanely interesting opportunity. I could sort of go into Tesla. This is my idea at the time. I could go into Tesla and be like an in-house journalist, telling the story of this company that has so many fascinating aspects and so many moving pieces. And I could help the world see that electric cars might be actually a good thing for the world.

• 24:31Guy Raz?

  Yeah. So you accepted this job and did you move to California with your?

• 24:36Speaker 02

  Yeah.

• 24:36Guy Raz?

  Then girlfriend, now wife?

• 24:38Speaker 02

  Then girlfriend, now wife. Constantly amused by that description. Um, yes, that job required me to move to the Bay Area.

• 24:45Guy Raz?

  All right. So this is 2014 and this is still, I think, before the Model 3 is, is, is been released.

• 24:52Speaker 02

  Yeah, January 24th.

• 24:53Guy Raz?

  And I, I remember I profiled Tesla maybe in 2009. Gosh, it was a long time ago. It was like when the Roadster was still, you know, that was their car.

• 25:03Speaker 02

  Yeah.

• 25:03Guy Raz?

  And, um, and so it was a different company, right? Like you probably saw Elon Musk regularly.

• 25:09Speaker 02

  Yeah, I saw him in the office regularly. I think there were like some thousands of people by the time I was there. So it was substantial. But I also was in meetings with Elon and I had a couple of one on ones with him. I started off, when I went into that company, I started off as like teacher's pet, but like, as what happens with many people, sort of quickly became persona non grata to Elon, but.

• 25:30Guy Raz?

  What, what happened?

• 25:32Speaker 02

  A bunch of things. I had worked on a report with, uh, one of the engineers about the batteries and how much cleaner they are than gasoline powered cars.

• 25:44Speaker 02

  And the report didn't come out the way he wanted it wasn't written in the way he wanted it edited in the way he wanted. I took over the social channels for Tesla and did some tweets that he didn't like. I got an angry email from him once about the state of the tweets. And that just sort of just contributed to a deterioration in the relationship.

• 26:03Guy Raz?

  But to be clear, I mean, it sounds like you were a big believer in what he was trying to do. I mean, you would eventually write the book about him. You didn't cooperate, but I mean, it was about this revolution in electric cars. And I mean, it sounds like you really did believe in what he was trying to do.

• 26:21Speaker 02

  I'm still a believer in that. I still think that electric cars are a much better option than internal combustion engine cars. And I believe that Tesla has made an amazing and important contribution to the world in accelerating that transition away from fossil fuels towards a cleaner energy economy.

• 26:41Guy Raz?

  I don't think that I don't think that can be denied by anybody, even people who hate Elon Musk. All right, so you're there for a year, you leave, you write this book. And I guess shortly after you leave, you get some consulting work at this company called Kik Interactive. Tell me how, and because now we're going to come together with you and Chris, how did that, how did you get work there? Were you just looking for work? Were you looking for consulting work?

• 27:06Speaker 02

  So what happened is while working on the book, wanted to figure out a way to pay my bills. And I thought, maybe I could work half time at Kik. And I liked Kik because I had become friends with Ted Livingston. And so I thought, maybe if I can get in and work with Kik, I can be close to this guy, Ted. It's a much more Canadian culture. It's totally different from Tesla, which was messy and cutthroat and had a like throw everyone under the bus kind of culture. And at Kik, I became friends with Chris.

• 27:37Speaker 01

  Can I tell one story from that period?

• 27:39Guy Raz?

  Yes.

• 27:40Speaker 01

  So Hamish did a bunch of stuff and probably in the natural course of things, we wouldn't, we would not have interacted that much because Ted was really the face of the company. But he had a weird. I don't know, quirk of his personality or preference or something where he really didn't want to go on TV, like he didn't like being on video.

• 28:01Guy Raz?

  Right.

• 28:02Speaker 01

  Uh, so he's like, Chris, you gotta go do the like, be the representative of the company in video appearances.

• 28:10Guy Raz?

  Right.

• 28:10Speaker 01

  And I was like, you know, the CTO, like, technical co-founder that was used to just hiding in a back room.

• 28:18Guy Raz?

  Yeah, right.

• 28:18Speaker 01

  And Hamish was kind of assigned to shepherd me through this process. One time I remember in particular, do you remember the time I had to go on Squawk Box?

• 28:27Speaker 02

  Yeah, Squawk was for the CNBC wanted to have one of the founders of Kik. Chris got assigned to do it and I got assigned to be his handler for it. And Chris is a little bit nervous about it, feeling a little bit uptight, I could see. And so it was eight o'clock in the morning and I thought, well, I think Chris should have a beer before he goes on, that might just help him loosen them up. And so he had an 8 AM Corona and I joined him as an act of solidarity. And then he went on the interview and crushed it. And from that moment on, became a media hero for Kik.

• 29:02Guy Raz?

  Wow. So you guys, you're the editorial, kind of editorial advisor at Kik, Hamish, and you get to know Chris because you're helping him prepare for interviews and you just become friends, basically.

• 29:16Speaker 02

  Exactly.

• 29:16Guy Raz?

  Meantime, um, and this is, I guess you're there over a two-year period. Chris, you are starting to kind of think about transitioning out and you leave in early 2017, um, and just to kind of take some time off. And what did you want to do during that year off?

• 29:34Speaker 01

  Mostly I just wanted to give myself some space. Like I had, you know, I'd done this crazy thing. I should take some time, live my life, you know, do some of the things that I would have done if I'd had spare time over the past eight years. Anyway, one of the things that was on this sort of bucket list was, you know, maybe I should write. And I had enough of sort of like the programmer's hubris where I was like, I know how to read, I know how to type, like, I should write, surely I would be good at that. And I started writing sort of an essay or a blog post or a screed outlining my frustrations with the media economy on the internet. It was very pretentious. It was very, there was

• 30:18Speaker 01

  a lot of like, Facebook is driving us crazy. Twitter is dividing us like wah wah wah wah wah. And I sent this essay to Hamish because I'm like, he's my friend who's actually a writer. And he let me down very gently. We joke about this. He was like, okay, like you're, it's 2017. You're writing this essay, the thesis of which is like, maybe the internet is bad for newspapers. Like, we know, this is not new information. But if you wanted to make this good, the more interesting question you should be asking in it is, so what? Like, let's assume that all of these things you're whining about are correct. How could it be different? I should mention, by the way, that Hamish disputes my interpretation of that essay.

• 31:01Speaker 02

  Yeah, yeah. It was not a piece of shit. It was a very good essay and it was very well argued. And I gave him a series of bullet points of feedback, mostly praising it. And then one of the bullet points, it was like, well, can we push this further? You know, people who work in the media know that these are the problems, but no one has a good idea of what the solution is.

• 31:20Guy Raz?

  What's the solution? Yeah.

• 31:21Speaker 02

  Yeah. And so that's what led to Chris. And we, we had this conversation about Chris is the systems thinker and the genius who is mostly responsible for the Substack model. And the core insight he had was that you should make readers the customers instead of advertisers the customers. And if you change that core dynamic, especially if you monetize a relationship over time through enough subscription, then different things are possible.

• 31:47Guy Raz?

  Right.

• 31:48Speaker 02

  But despite the world knowing that the, there are these grand problems with the business model that supports media, even some of the smartest, most well-funded minds and organizations weren't quite figuring it out. And it was starting to feel like, maybe this thing is all just going to crumble and we're all going to live in the Facebook world now.

• 32:09Guy Raz?

  Yeah.

• 32:10Speaker 02

  But there was one bright spark, and it was a really small bright spark. And it was a guy named Ben Thompson, who writes a publication called Stratechery, which is the worst name in media history.

• 32:22Guy Raz?

  Yeah, and he's had this blog for a long time.

• 32:24Speaker 02

  He had had it for a couple of years, even by the time we came around in 2017.

• 32:27Guy Raz?

  And I think he's based in Taiwan, right?

• 32:30Speaker 02

  Writing this thing out of this bare bedroom in Taipei. And he's just writing about the business models of technology companies. And his model is really simple. He would publish a blog post each week that was his most polished and best work. And that would be free. And then if you wanted more Ben Thompson, if you wanted his view of the world on more things, you could pay a hundred bucks a year and you'd get three more posts by him over email. And it was a really lucrative business for him. We figured out through napkin math and guessing, basically, that he was already making more than a million dollars a year from that. And Ben Thompson was telling anyone who'd listen, I don't know why more journalists don't try this model, because it works really well for me.

• 33:13Speaker 01

  We even called him up at one point.

• 33:14Speaker 02

  Yeah, we talked to him about all this.

• 33:16Guy Raz?

  And, yeah.

• 33:17Speaker 01

  He's like, I don't know why more people don't do it. I was like, so what did you have to do? He's like, well, I, you know, I invented the business model from scratch. I did it for a year with no money. I made my own tech stack and my own cobbled together product and editorial. Like, he sort of like described all of the things that went into him doing it. And he had to be this like triple unicorn of a great analyst and a great writer and a great entrepreneur and a great editor and a great technology wrangler. And we were just like, oh, that's why nobody does this. That's way too hard.

• 33:47Speaker 02

  He listed on one of his webpages, all the tools he uses just to run this thing. And there were like 19 different tech tools that he paid for. Most writers are not technologically savvy and don't, they don't want to waste their time wrangling those different tools.

• 34:00Speaker 01

  Yeah, you're a writer. You know how to write something great. That is rare and hard enough. And to expect you to also be this tech genius and this entrepreneur, it's crazy. You should be able to come and type into this box. And if the things you type are great, you're going to get rich and famous.

• 34:20Guy Raz?

  When we come back in just a moment, how Chris learns to push back when people tell him how bad his idea is. Stay with us. I'm Guy Raz and you're listening to How I Built This.

• 34:40Guy Raz?

  Does your team want a website that looks and feels handcrafted but is still fast to ship? Well, Framer is built exactly for that. With Framer, you design on a visual canvas with responsive layouts, hosting, and a CMS built in, so the work is production-ready from day one. And you can get it done with help from Framer's AI agents. Framer is the AI website builder that helps creators, teams, and businesses ship production-ready sites faster than ever while getting every detail right. Prompt, inspect, edit, and publish in one place at a whole new pace. AI agents and humans work together. The agents bring speed and scale,

• 35:24Guy Raz?

  and people bring taste, judgment, and control. Learn how you can get more out of your site from a Framer specialist or get started building for free today at framer.com/built for 30% off a Framer Pro annual plan. That's framer.com/built. Rules and restrictions may apply. AI isn't just opening new business opportunities, it's changing the way businesses get work done. The questions they ask, the decisions they make, the routine tasks they can hand off. That's the idea behind NetSuite Next, the next generation of NetSuite with AI woven into the tools your business already relies on.

• 36:07Guy Raz?

  NetSuite Next surfaces insights exactly when you need them, puts agents to work on routine tasks and problems, and lets you ask complex questions in plain language, like talking to a knowledgeable colleague. But technology is only part of the story. AI is also reshaping how people and teams work together, and that shift is already underway. That's why NetSuite wants to put a new, expert-created business guide in your hands today. It's called "A Lining for the Agentic Era: How AI is Changing Everyday Work." And right now, it's yours, absolutely free. Inside, you'll discover how AI could reshape work across your entire organization, and how to position your business to prosper from it.

• 36:52Guy Raz?

  If your revenues are at least in the seven figures, get NetSuite's free business guide, Aligning for the Agentic Era: How AI is Changing Everyday Work, at netsuite.com/built. The guide is free to you at netsuite.com/built. netsuite.com/built.

• 37:11Speaker 03

  Football is back, and PrizePix is bringing out their best offer yet. New users who sign up will get $150 in lineups if you win your first $5 lineup. That's right, if you win your first $5 lineup, you'll get $150 in lineups. On PrizePix, you simply pick two to six players, pick more or less on their stat projections, and submit your lineup. Then sweat it out as you watch your picks play out live. It's the best way to get more locked in on game day. Make all the picks you want this football season, all in the same app. And now, PrizePix is available nationwide. So what are you waiting for? Lock in for kickoff, because everyone and everything is on PrizePix. What you on?

• 37:56Speaker 04

  Download the PrizePix app today and use code WONDERY, that's code WONDERY, to get $150 instantly in lineups if you win your first $5 lineup. PrizePix, run your game. Must be present in certain states. Visit prizepix.com for restrictions and details.

• 38:18Guy Raz?

  Hey, welcome back to How I Built This. I'm Guy Raz. So it's 2017, and Chris and Hamish have an idea for a new digital platform for writers. And even as they're talking about partnering on the idea, Hamish, the journalist, is wary about becoming a founder.

• 38:36Speaker 02

  I knew that that was a stressful life where you could never really switch off, and there'd be many dramas, and you're responsible not just for your own job and income, but for whoever ended up working for you, and then all your customers and all that kind of stuff. So I was excited to go back to journalism at that time and be plotting my next book and returning to freelancing. That's what I was really amped up for. But Chris, annoyingly...

• 39:03Speaker 02

  Was coming down to San Francisco every so often and one of these trips he stayed with me and my wife, I think she was by that point. And once he was excited about that idea after I had prompted him to like, just invent the new model that was going to save everyone because complaining in an essay isn't enough. He started to go to work on me to convince me that I had to do this with him. I had to build this company with him. And I was like, no, no, no, no, no, that sounds like a horrible life. And I'll just be a consultant or an advisor and I'll help you along the way and point you in the right direction. And he didn't accept that answer. And he kept working away at me and trying to persuade me that I had to do this and this is going to be fun. And then my wife, Steph, kind of teamed up with

• 39:48Speaker 02

  him and agreed that I sort of have to do this because it's too much of a convergence of my interests and experience and the things that I like to do.

• 40:01Guy Raz?

  Chris, why did you think you needed Hamish so badly? I mean,

• 40:05Speaker 02

  Good question.

• 40:05Guy Raz?

  You were a tech guy and, and obviously Hamish is a talented journalist and writer, but why were you so convinced that you needed him to start this thing?

• 40:14Speaker 01

  I mean, I knew nothing about this world. I didn't know the people. I didn't know how they thought. I wouldn't have even known where to start. I can think about things through, from first principles and having both halves of the brain, having the first principles understanding, but kind of pairing it with being of that world and knowing the language and knowing the people was actually like the magic that made it work.

• 40:43Guy Raz?

  So, Hamish, you were, so you basically were like, okay, I'll try this. I mean, you did not want that life. You knew what it was going to entail. The like, long days, the travel, the sleepless nights, worrying about other people's incomes and you agreed to sign up for this.

• 41:00Speaker 02

  I did. And you know, I think it's important to mention that I thought that this model that we'd devised was kind of stupid enough to work. It was either, it was so simple that it had some obvious flaw that we just had missed for some reason, or it was so simple that it was actually gonna work. And if it could work for more than a few people, then I think it could work for many, many people. And in that world, the difference it could make would be profound.

• 41:25Speaker 01

  Can I make one, one point here that I think is really interesting?

• 41:28Speaker 02

  Yeah, please.

• 41:28Speaker 01

  You've mentioned that thing, it's like, it's so stupid, like, either we're stupid, or it's going to work. I definitely remember that. Like, the way I would have described it at the time was like, we couldn't talk ourselves out of this idea. But it was kind of like, it, it was a, it was a good idea for a company and a bad idea for an essay, which is how it started. Like, you could tell people this thing, and they would give you a blank stare. Like, I would tell people in my life, hey, we're gonna make this platform that's gonna, you're gonna pay for writers on the internet that you really like. And they would, like, look at me like I had horns. Or they would, they would take pity on me. They would say, like, oh, that's, that's so nice. That would be so cool if that worked. But, you know, and I'm sorry to be the one to have to tell you this, you idiot, but like, nobody's ever gonna pay for something on the internet.

• 42:12Speaker 02

  Right.

• 42:12Speaker 01

  And people would tell me, people would be like, that sounds great, but I would never pay for something like that. And I devised this, like, parlor trick, where when somebody told me they would never pay for something on the internet, I would say, well, who's your favorite writer? And they'd say, oh, you know, Guy Raz, or whoever. And then I would say, would you pay five bucks a month for that person? And they would say, well, yeah, but that's different. Like, that's a special, that's a special case. Like, that's, it's, it's so and so. Like, they're really good. And so I think the, in retrospect, I think we were on to something that, like, was a good idea, but sounded bad, or like, didn't, it, it, it was not yet. In the realm of a thing that people would believe, but it was a realm of thing that people would do.

• 42:55Guy Raz?

  Right. So this was, I mean, so basically you're looking at this and saying, well, if you're creating content and you're bringing people to the platform, they should be, the people doing this should have a guaranteed way of reaching those people.

• 43:11Speaker 01

  They should own the connection. It should be their relationship. When you subscribe on Substack, you don't subscribe to Substack. You subscribe to Guy or whoever.

• 43:20Guy Raz?

  Yeah. It's an important point because this is 2017 when you're having the conversation and it's even more of an acute issue now, which is that you might have a million subscribers on YouTube, but if YouTube changes the algorithm and stops delivering your videos to people automatically, it might be really hard to make a living off of that. But YouTube still benefits every time you post, or Facebook benefits every time you post. Instagram and TikTok, they benefit because there are more eyeballs and there are more advertisers.

• 43:53Speaker 01

  And this had happened with Facebook pages at this point. They'd created a thing where people spent all this money getting people to like their Facebook page, on the assumption that that meant they'd built up an audience. And then they said, oh, just kidding, actually, when you want to reach those people, you have to pay again.

• 44:07Guy Raz?

  Yes.

• 44:08Speaker 01

  And that had worked for Facebook very well.

• 44:11Guy Raz?

  And by the way, I mean, there were other models, Patreon, right, for musicians and artists and filmmakers, like that existed. People were being supported for their work through Patreon.

• 44:24Speaker 02

  Yeah, Patreon, I think, is a hugely important company because it changed the culture. It showed not only that people will be willing to pay for content online, they'll be willing to pay for the artist or creator who they most love or trust. And we looked at Medium and learned a lot from Medium and took lessons from both of them, where they had struggled, or what could have been better, and got to benefit from standing on their shoulders to design something like the Substack system.

• 44:51Guy Raz?

  Yeah.

• 44:51Speaker 01

  I mean, this was one of the things that kind of went into my calculations here. I was like, what if we made something that had a business model from the start and we knew what was... And that's actually important because the thing that we were on to at this point, as it was turning from like an essay into a company that we needed to start, was the big idea of... What if you completely changed the economics of how these platforms worked? The problem with Facebook is not that it doesn't work, right? The problem with Facebook is that it works too well and doesn't serve the people who use it.

• 45:23Guy Raz?

  Right.

• 45:23Speaker 01

  Yes, it kills all the newspapers, but it's a massively successful business that takes advantage of the scale of the internet, yada, yada. So what if you could like, design a new economic engine, a new incentive structure that could harness the scale and network effects of the internet, but then actually paid money to the people who were making the culture? And at the same time, we had this thing that we could hold in our hand that was like, what if we just made it like 100 times easier for the next Ben Thompson to do a paid email newsletter?

• 45:59Guy Raz?

  Yeah. So Chris, you're in Kitchener in Canada and Hamish, you are in San Francisco and you obviously you're communicating every day, but Chris, you are on your own, starting to build the platform? You're just working on trying to create this thing that would become Substack?

• 46:22Speaker 01

  Yeah, I mean, it was pretty, it was pretty simple to start. It was just a website that could host some content and, but I mean, the thing, none of it was rocket, like, none of it was technically rocket science. It wasn't like we were building some software that only we could have built, but it was just like the, putting it together and having it actually work the right way was the new thing. And it, I mean, by the way, it turned out to be pretty hard. Like it was, it was, I think we were right about some of the core insights. We got some early breaks that really helped, but it was, it took, there was a whole series of things that we had to kind of like, believe and act on for long periods of time that

• 47:06Speaker 01

  is, it's hard to do.

• 47:08Speaker 02

  Yeah. And like 2017, writers were not the sexiest customer base in the world. No one thought they were going to build a billion dollar tech company by serving writers. In fact, people were forsaking writers, forsaking the media, turning their back on that, they'd given up on that.

• 47:23Guy Raz?

  So, all right, so you are building this, Chris, and Hamish, you are kind of trying to drum up potential people to join this platform.

• 47:32Guy Raz?

  And it officially launches in 2017. Before we get to that, up until that point, right? Because I think you guys really kind of decide, let's do this in July. So that summer of 2017, you guys are really working on, on, on building this thing. Because you're going to launch it in October. You probably didn't need a whole lot of money at this point, right? I mean, you had a little bit of money from, from your time at Kik, Chris. So were you able to use some of that money to just finance what needed to be financed initially?

• 47:59Speaker 01

  Yeah, I put in a little bit of money to basically like pay the hosting bills. And, you know, we bought a domain and there was, but it was sort of like minimal at that point.

• 48:08Guy Raz?

  And, and given, and we've had this conversation with co-founders many times. Given that, you know, you're initially kind of this idea that you have in your head. Hamish helps you to kind of refine it. How did, you know, you, you had some money to put in and Hamish probably didn't have a whole lot of cash to put in because you're, you're a jokey journalist. How did you guys have that delicate conversation about, okay, here's how we're going to, you know, split the company?

• 48:35Speaker 01

  How did we have it?

• 48:37Speaker 02

  You insisted on splitting that evenly based on past lessons and ideals you've developed for yourself since.

• 48:45Guy Raz?

  So that was it? It was like, we're just going to split it?

• 48:47Speaker 01

  Yeah.

• 48:48Speaker 02

  That's right. You, well, what happened is that my grandmother had recently died and passed down some money. I was, I had no money. I had, my, well, I paid a check to paycheck with my wife in 2017.

• 49:00Guy Raz?

  Yeah, like probably putting in $10,000 at that point for you would have been just like...

• 49:04Speaker 02

  We couldn't do that. We couldn't do that. And this, this is why Steph's support was so important. She was okay with the risk. And luckily I had this inheritance money from my grandmother that I spent all on, I spent all of it to just cover my salary for a few months before we raised a proper round of money from like more friends and family that could help us start to pay ourselves a little bit of a salary.

• 49:28Guy Raz?

  So, all right. So that summer, you're working on it. And by October of 2017, you're ready to officially launch. And you've got this guy, Bill Bishop, who you knew, you knew him from your, your time in Asia. Hamish, he had been writing about China. And he agreed to, because I guess this was a free... Blog that he was writing and he agreed to join Substack and to start charging?

• 49:52Speaker 02

  Yeah, he accidentally had a really successful free newsletter. He'd been running it for five years. He'd never really made money off it, except for doing a couple of donation drives.

• 50:02Speaker 01

  He was paying a bunch of money to send the emails.

• 50:05Speaker 02

  Yeah. And so Bill had been talking in his newsletter that I was a reader of. He'd been talking about how he's going to introduce a paywall soon. He's going to introduce a paywall soon. He'd been talking about that before we started Substack and I'd been noticing that he kept talking about it, but never getting around to us. And so halfway through his process there, I jumped into his inbox and said, my friend and I are starting this thing, which is kind of like, we'll take care of everything for you, this thing that you're describing that you want to do. So you can just worry about the writing. Would you be interested in being a guinea pig for this? And he luckily said yes. And so we got to launch with kind of the ideal first customer, the perfect first publisher. That happened in October 2017.

• 50:50Guy Raz?

  And did you at that point, Chris, move to California or were you still in Canada?

• 50:55Speaker 01

  I was still in Canada. We launched Bill and we'd also applied to YC.

• 51:00Guy Raz?

  So Y Combinator.

• 51:02Speaker 02

  You should talk about how you're a Paul Graham fan and that was like part of your inspiration for writing these essays.

• 51:08Speaker 01

  I'd been a Paul Graham fan. I'd been.

• 51:10Guy Raz?

  The founder of Y Combinator, obviously, yeah.

• 51:13Speaker 01

  Yeah. And so we applied to YC with Substack. And I remember the timing because on the application to YC, it said, how much money are you making? And we said, $0. And then between the application and when we came in for the interview, Bill's launch happened. And we had no, I had no idea what to expect, but he made like six figures his first day through this like duct taped like Stripe setup that I had built in the preceding weeks. But we just woke up and we were like, huh, like, I think this is, this seems good. Is this good? This seems really good.

• 51:45Guy Raz?

  All of a sudden, more than $100,000 of revenue, annual revenue, based on his, oh, his single.

• 51:52Speaker 01

  In like a day. It was just like that. It was just like you watch it's like. Boom. And so we went a few, like, you know, a few days after applying, we flew down and went to the YC interview. And they were like, you know, it says here, you're making $0. And we got to say, oh, actually. And I think it contributed to a sense of real momentum. And it was, it was sort of funny because our advisor, Jared, looked at that and he was like, oh, this is going to be easy for you guys. Like you just, you have one customer that did this. You just need like four or five more of these and you're going to be like sailing off to the races and raising money is going to be so easy. Meanwhile, it took us years to have that kind of success again. It was very like, we just had that perfect, you know,

• 52:33Speaker 02

  Not quite, not quite years, not quite years. It was much harder than we thought it was going to be.

• 52:38Speaker 01

  It wasn't, it wasn't as simple as get the next four Bill Bishop's. There weren't the next four Bill Bishop's, but it gave us such a burst of confidence that we were on to something that it sort of helped sustain us, I think, through the next, the next phase.

• 52:54Guy Raz?

  All right. So you get into Y Combinator, obviously a big deal because now you've got, you know, you're going to get exposure to big time investors and you're going to get mentorship. And I'm assuming that's when you moved to, to California, Chris.

• 53:08Speaker 01

  Yeah, I came down for YC. We did the thing.

• 53:11Guy Raz?

  Okay. So you're, you're now together. In 2018, you did raise some seed money and you got some interesting investors who, who I guess were interested in, in this. And I imagine Y Combinator being part of Y Combinator was certainly helpful.

• 53:26Speaker 01

  Yeah, the YC, we did the YC demo day thing. And I, I think I would characterize us as being kind of like, we were not one of the, obviously the hot companies that everybody's clamoring for. But we were also, you know, we raised around, we were not one of the struggling ones. We were kind of just like middle of the pack.

• 53:43Speaker 02

  Yeah. I, I remember on the first demo day we did, which is the one that's for YC alumni. Emmett Shear came up to me and he said,

• 53:52Guy Raz?

  Emmett Shear, founder of, co-founder of Twitch, who was on the show a couple of years ago. Yep.

• 53:56Speaker 02

  Yeah. He's like, I look at you guys, I'm really excited about this idea. I think you guys are like Twitch, but for journalists and I want to invest. And so we got him as an early investor and then there's a bunch of people who sort of saw the same thing around that time. And so by the time we finished YC at the end of March, we had, we, 7,000 paid subscriptions across the network that we could point to and say, look, this thing is working. This thing is going somewhere, at least somewhere relatively interesting.

• 54:24Guy Raz?

  Let me ask you about the business model and the math, right? So the model, if I understand it correctly, from the beginning and even till now was the writer gets, basically, you guys get a 10% commission or whatever, plus there's going to be the payment processing fees, which is another 2% or something. And so effectively, the writer's getting about, let's say, 85% to 87% of the total revenue. How did you work? I mean, that math is, by any account, very beneficial to the writer, right? They're getting a good deal here.

• 55:06Guy Raz?

  If you compare that to any other platform, the writer's doing really well, but it means that your margins are really thin. How did you come up with that math instead of, let's say, 20% or 25%?

• 55:18Speaker 01

  Well, it's interesting. It starts out as a really great deal. Coupled with that, by the way, everything else is free. So we're not charging you SaaS fees to host a website, to send email to any size. Everything else costs nothing. We wanted to be in a world where we would only make money if the people actually made money. I didn't want to be in the business of selling people a dream of doing this thing, and they would pay us, but then they wouldn't make money, and, well, tough for them. And then it's a great deal at the start, and then you start to get, by the time you're making millions of dollars a year, that 10% starts to look substantial. And you start to think, wow, aha, I see.

• 55:57Guy Raz?

  But that was going to take a while. And I think even now, it's a very small number of people who are making over a million. A small, you know...

• 56:05Speaker 01

  Not as small as you might think anymore, but it scales, right? We really want you to succeed.

• 56:11Guy Raz?

  Yeah.

• 56:12Speaker 01

  At the very start, we only handled, only paid newsletters, only paid subscriptions. And then we very quickly figured out, if you're going to have a paid newsletter, you need free subscriptions as well, and we have to handle those. And then we very quickly figured out, if you're going to become a paid newsletter, you're going to start as a free one, so we should make it so that anybody can use it for free. And that became a big piece of how the top of funnel kind of worked for us.

• 56:36Guy Raz?

  All right. So here's my question. Initially, right, now, you're getting some momentum, right? Why Combinator? Obviously, people are starting to believe in you. But I just want to be clear about something to people listening, which is... Y Combinator, we know about the Coinbase's. We know about the Airbnb's. We know about the Instacart. But most of the companies that come out of Y Combinator don't end up making it. I mean, the founders might go on and do something else. So just being in Y Combinator is a guarantee that it's going to work. And so we've seen these headlines every day. So and so company was, your own company, Kik, was valued at $1 billion at one point.

• 57:19Guy Raz?

  Knowing now you are the CEO of this company, you've learned a lot of lessons because you were the CTO of that business. What did you, what was the sort of the primary kind of lesson that you took from that experience that you were like, we're not going to do that here because I saw what happened and it ended up going south?

• 57:38Speaker 01

  I think there's probably two things that I think about a lot. One was just have a business model.

• 57:46Guy Raz?

  It seems barely straightforward.

• 57:49Speaker 01

  It seems unkind in retrospect to say, oh, we just had this theory of like, we'll get a bunch of users and then we'll figure out the business model. But you have to remember that worked for some of the biggest companies in the world. That worked for WhatsApp, who sold for $22 billion. So I don't think it's like, I don't say that as a criticism to say we were stupid for thinking if we got a whole ton of users, we would be able to like turn it into something. That was not a ridiculous way to operate. But it did leave me determined to operate in a different way this time and to have an idea from the get go of like, what is this business? And then the other one that I think about a lot is like, there's this saying in Silicon Valley that is, keep the main thing, the main thing.

• 58:30Speaker 01

  And we went through this at Kik where I think even after like, I think we were always kind of unmoored. We were always thinking about like, and because we didn't have a business model, we're like, what are we going to turn this into? But there was a lot of kind of like, trying to figure out the next thing instead of making the main thing actually work. And I think with Substack, we're trying to do the opposite of that. We're trying to have, there's like a core of what Substack is and like, that's the thing.

• 59:01Guy Raz?

  When we come back in just a moment, Elon Musk comes back into the story, this time to make Chris an offer that he can and does refuse. Stay with us. I'm Guy Raz and you're listening to How I Built This.

• 59:32Guy Raz?

  Hey, welcome back to How I Built This. I'm Guy Raz. So it's around 2019 and Chris and Hamish have built a solid scaffolding for Substack. Writers offer their content for free or for money, and Substack gets a cut of the subscriptions. But now, the question is, how do they get more writers?

• 59:52Speaker 02

  We looked for people that we thought weren't being well-served by the dominant media structure, but actually had interesting things to say and had a devoted audience. And so it wasn't necessarily the people with the largest audiences. Maybe they'd have a smaller following on Twitter. Twitter was a common hunting ground in those days. But the people who were following them were really paying attention to what they had to say. And we developed this tool that allowed us to put like fire emojis beside the names of the ones who had these really devoted audiences. And so if you had-

• 1:00:24Speaker 01

  It was like a Richter scale. Three fire emoji was 10 times as good as two fire emoji.

• 1:00:29Speaker 02

  Yeah, so if you had one fire emoji, you're like, your audience didn't really care that much about what you were saying. If you had three fire emoji, okay, like, we're pretty sure you're going to work on Substack. If you had four fire emoji, we knew you had the kind of audience that would really respond well to you going independent and would have this direct relationship with you and could help make you get rich with this model, basically.

• 1:00:51Guy Raz?

  And let's say a prominent writer, I mean, has a million subscribers. They really just need a fraction of those people to pay them a monthly fee to make significant money, right? I mean, the math is clear.

• 1:01:06Speaker 01

  Totally.

• 1:01:07Speaker 02

  It's surprising how much we had to make that obvious to writers, actually, over the course of the years. It was- They're used to dealing with huge numbers in terms of audiences, but getting paid pennies as a result, whether by an employer or through the revenue share agreements of those other platforms. And we would have to say to them, "Look, if you get 1,000 paid subscribers and they're paying you 50 bucks a year, do you know how much money that is?" And they're like, "Look, that's enough to live on." And it wasn't always obvious to people. People didn't take that step. And then we're like, "If you get 10,000 paying subscribers paying 50 bucks a year, that's enough to actually like really make serious money and change your life."

• 1:01:41Guy Raz?

  Half a million dollars. Yeah, that's no joke.

• 1:01:43Speaker 01

  It's surprising how much you have to do that multiplication for people. Like, it's not that they can't do it themselves, it's that they won't do it. And the number of times I've had a conversation that's like, you know, so-and-so has 10,000 subscribers paying, uh-huh. They're charging $100 a year, uh-huh. So they're making a million dollars a year.

• 1:02:00Guy Raz?

  What?

• 1:02:02Speaker 01

  And it's sort of like, you know, you could have got there yourself, but you sort of have to like point out what's happening.

• 1:02:09Guy Raz?

  Very fortuitously, you had raised money in the summer of 2019, which would come into great use, I'm sure, by COVID. You raised $15 million, it was led by Andreessen Horowitz. But you've got the pandemic. And this really is a turning point year for you. I mean, in many ways, I think you would both agree because of circumstances beyond your control. On the one hand, you've got the pandemic. A lot of the social media companies were, as many of them have admitted, cooperating with the government to deplatform specific people who were talking about, who were opposing COVID vaccines, for example, or people who were writing about what was perceived to be misinformation, right?

• 1:02:51Guy Raz?

  And so there's this kind of, all these things happening in the background. On the one hand, the social media companies are deplatforming and banning people. On the other hand, prominent journalists are losing their jobs or are feeling under pressure. And so you start to get people coming to your platform. Matt Taibbi, Andrew Sullivan, Barry Weiss, leaves the New York Times, starts a Substack.

• 1:03:19Speaker 01

  It was a big pull forward for us. I mean, we grew something like 6X in that first year of the pandemic. I had this speech that I would give to people at a time. I was like, "Think of Substack as your getaway vehicle." You don't have to get in it right now, but like fuel it up, have the engine idling, like create your account, like claim your handle, have this thing ready just in case something unexpected happens. And if you're in the media in 2020, that wasn't like, that didn't sound crazy to you. And then sure enough, you know, over the, we had that conversation with Andrew, it was expected to be months. Uh, you know, he calls us after a weekend, basically says, you'll never guess what happened. And we were like, you know what? We actually might be able to guess what happened. And, you know, he was out, he'd been fired.

• 1:04:03Speaker 02

  Well, he resigned under, under duress.

• 1:04:05Speaker 01

  He was, yeah, sorry. I shouldn't say fired.

• 1:04:08Guy Raz?

  This is in 2020.

• 1:04:09Speaker 01

  This is in 2020. And there was a moment where a lot of those kinds of people you're talking about, the people who are, you know, the recalcitrant voices that don't like being told what to say and were kind of like not going with the program were both the people who are selectively the most interesting to read, the people you actually would care about, don't want to fire, or sorry, want to, you'd want to subscribe to them if you're a reader. But there was a moment where a lot of them got either fired or pushed out or had some kind of moment where they were suddenly unwelcome in the institutions they'd, they'd made a home in and invested in. And so we had done a bunch of things like having

• 1:04:51Speaker 01

  a stance on freedom of the press and on how it was the right way to approach content moderation that were very non-obvious and non-consensus at the time that we took a lot of heat for, that we would not have been willing to take a lot of heat for, that we not have a theory about what was happening and what mattered and why, that set us up to be the platform that those people could trust when that moment hit. I mean, a big part of it is the business model, right? Like the fact that we was paying subscribers. We didn't have advertisers who were getting spooked and boycotting us, bringing us under

• 1:05:32Speaker 01

  pressure. I think we were not yet at the size where we were getting the government attention that the X's and metas were of the world.

• 1:05:41Guy Raz?

  And let's be honest, I think objectively, voices that

• 1:05:46Guy Raz?

  All of us here could agree we're objectionable, like people who are racist or spewing conspiracy theories that we may find objectionable. There was a lot of pressure to deplatform people who I'm sure even both of you personally thought, ugh, I'm uncomfortable with this person. So how did you, how did you do the gymnastics in your brain at the time when the culture was somewhat different to say, nope, we're still gonna let that happen?

• 1:06:15Speaker 02

  With conversations at the time, because we were confronted with this kind of thing in small ways and then bigger ways and then more public ways that led to us reaffirming our belief and our position on it and caused us to do things like write down and publish our view of this, like why we have a hands-off stance on content moderation, which doesn't mean no stance at all. We still protect the platform of the extremes in line with the First Amendment. No incitements to violence, no spam, no doxing, et cetera.

• 1:06:45Guy Raz?

  Et cetera, such as to be clear, no incitements to violence, no spamming people and no doxing. So you can't expose where people live or personal information about them if you don't like them. Those are red lines. If you do any of those things, you're off.

• 1:06:58Speaker 02

  Right. And so our view of the world was not that the way to address these problems was to devise more sophisticated content moderation. We'd seen the attempts of the other social media companies to do that. They'd invested billions of dollars on this. They come up with these policy documents that are hundreds of pages long.

• 1:07:18Guy Raz?

  Yeah.

• 1:07:19Speaker 02

  And it doesn't appear to us like it has actually helped misinformation problems or it's helped reduce the level of harassment or it's helped increase trust in the media ecosystem writ large. Our view of things was the way to solve these kinds of problems, address them or mitigate them, is through changing the business model, changing the kinds of behaviors and content that can succeed on the platform.

• 1:07:44Guy Raz?

  And so the theory is like, if people are writing a lot of nonsense, they're just not going to succeed on Substack because it's not an outrage machine like social media. It just doesn't work in the same way where that actually is successful.

• 1:07:58Speaker 01

  To me, that's probably too rosy. Like, I think there's, you know, I sometimes think of Substack as an index fund of culture. There's like, whatever people are willing to pay for, whatever people are interested in, there's gonna be that, that thing. I don't think our role as a platform on the internet should be to tell you what's right and what's wrong, or who to trust and who not to trust. And it's a seductive idea that it should be that role, and a lot of platforms took that stance, and it just didn't work.

• 1:08:28Guy Raz?

  But you guys have responded at times, like, there was an article that you know about, it was written in The Atlantic, in November of 2023, it was called "Substack Has A Nazi Problem." And this writer identified, I don't know, 15 or 20 newsletters that use Nazi symbols. You guys did ban some of these newsletters, so what was the reason behind that?

• 1:08:50Speaker 01

  So, I mean, our stance on this is, look, we have a set of content policies. If something comes to our attention that is against the broadly applicable Substack rules, we're gonna take action. But we're not changing what we, what we enforce based on pressure.

• 1:09:07Guy Raz?

  Because, as you know, I read a lot of Substackers, and, and I really, and I pay for a bunch of them. And based on, on what I see, I still feel like the best or most prominent writers tend to be iconoclasts. Now, obviously, there are some who are on the left, but I find that the ones that I seem, seem to feel like are, are more successful are like, maybe on the sort of the libertarian center-right. Is that fair? Would you say that's fair?

• 1:09:38Speaker 02

  You should look at the leaderboards of Substack, which is ranked by revenue. And in the, in the US politics category, for example, you'll see a diversity of perspectives represented. And there's like, some of the top ones are like, very hard on the left. Some of them are very hard on the right or libertarian. I think there's a true mix, but I actually don't know that one dominates the other.

• 1:10:03Guy Raz?

  Okay, let's go back to our old friend Elon Musk. Kuhemish, you first encountered back in 2014, I think, when you started to profile him. And then it would eventually work for him. He comes back into your world. Less than 10 years later, he buys, of course, Twitter, which becomes X. Now, I think, fair to say, one of the, if not the most influential, sort of, social media platform in terms of shaping policy, because it's clearly red in the White House. And he buys it. And one of the things that happens in 2023 is you guys launch Notes, which is a sort

• 1:10:45Guy Raz?

  of a short feature where you can do short-form content, you know, to your followers on Substack. He basically says, look, this is a Twitter clone. And he kind of, kind of, you know.

• 1:10:58Speaker 01

  Completely flips his shit?

• 1:11:00Guy Raz?

  Well, he, what's, is he fire the, fire a shot across the bow? Like, he basically says, anyone tweeting out a Substack link, we're just gonna block those.

• 1:11:09Speaker 01

  Even mentioning the word Substack was briefly, was briefly banned. If you search for Substack, it wouldn't work.

• 1:11:14Guy Raz?

  Yeah. To clarify, there are plenty of people who, to link their Substacks on Twitter or X now. It's very common. And so that's obviously no longer the case. But let's just talk about, and Hamish, I'd love to hear your take on this, because he's somebody you really did admire for the work he did around electric cars. And, and I think that you felt this way, but all of a sudden, you're on his radar as an enemy. And that's no joke.

• 1:11:41Speaker 02

  Yeah, it's an unusual and uncomfortable experience. I continue, I continue to believe that about SpaceX and Tesla and some of the other things he's been involved in. He was instrumental in starting OpenAI as well. These are major contributions to the world. But that doesn't mean that he doesn't have some personal shortcomings and social shortcomings that show up in other ways. So it sort of sucked at the time. I think he misunderstood and misinterpreted the thing we're doing by launching this Notes feed, which is only similar to Twitter in the way that an electric car is similar to a gasoline car.

• 1:12:23Speaker 02

  The steering wheel looks the same, and the wheels look the same, and there's a windshield, etc. But the thing that powers it is ultimately creating a totally different product that is better for the end consumers and better for the world. And the Substack feed is not Twitter, but it's this subscriptions machine, basically, that helps the independent writers and creators of the world find new audiences and retain them.

• 1:12:50Guy Raz?

  And just to slightly back up for a second, I mean, I should mention that right around this time, Elon Musk actually made an offer to buy you guys out. And I think, I think the way this started is that right before you released Notes, you called him like, and you guys, or let him know that you were going to do it as a courtesy, I guess. And, and what, you had like a call with him and told him that?

• 1:13:14Speaker 02

  Yeah, we gave him a heads up as a courtesy that we're launching Notes the next day. And that, you know, some people are going to perceive this as a Twitter competitor, but we don't see it that way.

• 1:13:24Guy Raz?

  I see.

• 1:13:24Speaker 02

  And he responded by getting Chris on a call and saying to him, well, how about Twitter acquire Substack? And you, I'm looking for a CEO to run the company.

• 1:13:35Guy Raz?

  This is before Lynda?

• 1:13:37Speaker 02

  Before Lynda Yaccarino, like within weeks, actually.

• 1:13:40Guy Raz?

  Yeah.

• 1:13:40Speaker 02

  And, and so I'm looking for a CEO to run the company. I don't want to be the CEO. So how about you come and do that? And I'll be the chairman. And how about you think about that? And so we went on an accelerated process of thinking about that.

• 1:13:55Guy Raz?

  That seems like an interesting, I mean, an interesting offer, right? He's saying, hey, we'll buy you. And at this point, you know, you raised some money and, you know, you're doing well and he's probably going to offer you premium. And you could be the head of the whole operation. What did you think, Chris?

• 1:14:12Speaker 01

  I guess I tried to imagine that playing out. And I didn't think it would be.

• 1:14:20Speaker 01

  What I think of as like a CEO role, like he runs that place now. He made all the decisions. He's, you know, to my mind, done a lot of things that make sense from his perspective, but would not be what I would see as supporting the cause of free speech or as a, you know, a neutral, independent platform.

• 1:14:43Speaker 01

  I gotta, I mean, it's, it was interesting, right? It would have been like one of the most interesting, crazy things to contemplate doing. But for me, ultimately, I didn't think it would let us make the thing we set out to make.

• 1:15:00Speaker 02

  This is on the eve of launching Notes and he had saying like, well, do you want to come in and do this and be part of Twitter? And we're like, hang on, we're not going to talk about that right now. We need to focus on Notes. And the next day we launched the Notes, there's this huge reaction on Twitter about Substack being the Twitter killer now.

• 1:15:15Speaker 01

  I think he took that launch as a no, which is fair enough.

• 1:15:19Speaker 02

  Yeah. And then that's when the bad things happened.

• 1:15:21Guy Raz?

  And the bad things were him sort of.

• 1:15:23Speaker 02

  Him nuking Substack, yes, suppressing Substack links, making accusations about how we're using the API.

• 1:15:30Guy Raz?

  Yeah.

• 1:15:30Speaker 01

  We had been using for, since the start of Substack, we'd been using the Twitter API. So you could link, you could sign in with Twitter, you could link your Twitter. And he's got really mad that we'd been using this API and sent me a bunch of threatening stuff saying, why are you using this stuff to blah, blah, blah? Got quite angry at me.

• 1:15:53Guy Raz?

  And I guess at the time, I mean, just to put it in context, I mean, he was, because of the changes he had made at X and, and sort of the, the media narrative and, and look, you know, I think some legitimate, certainly legitimate blowback and criticism, they were struggling. They were not having, there were no advertisers and they're losing advertisers. They were hemorrhaging cash. A lot of people were like, what the, what did he do? Why would he buy this for, you know, $44 billion? Why would he buy, now of course, saying they're reversed and like, look, he's got 200 million followers and he, he's, he's the most powerful.

• 1:16:27Speaker 01

  Basically runs the country.

• 1:16:29Guy Raz?

  Right. In one of the most powerful voices in the world. So it was a bargain, but at that time in, in mid 2023, that was the narrative. So I guess from his perspective, he was probably feeling threatened, right? And, and were you guys? Worried that he that that those decisions could have a negative impact on your business?

• 1:16:50Speaker 01

  I think he overestimated how negative that impact would be. Like, he thought he could kill Substack. And he said as much to me.

• 1:16:59Guy Raz?

  He said to you, we can bury you.

• 1:17:02Speaker 01

  Yeah. There wasn't, there would have been a time in Substack's history when that was true. Like, if this had happened in in 2019 or 2020, like, yeah, I think that really would have, like, set Substack back a lot. But by the time it went down, the share of Substack traffic that was coming from Twitter had been on a steady decline for years. And I think he thought that it would be like, he sort of had the the ability to to crush us.

• 1:17:31Guy Raz?

  Basically, it sounds like the only course of action was to just let it pass. There was gonna be, it was gonna be painful on a certain number of levels, but you just eventually it would just pass.

• 1:17:41Speaker 01

  Yeah, I think once we we did that launch, we were sort of, we were committed.

• 1:17:45Guy Raz?

  So interestingly, now, 2025, when Twitter's fortunes have have turned and Substack obviously has also grown and is successful, he actually, I've seen him tweet links to Substack pieces. So clearly, clearly not an issue anymore.

• 1:18:06Guy Raz?

  As of the end of 2024, you had, it was reported that there were about 35 million active readers and about 4 million of those people were paying subscribers. Probably a little bit more now by the time we're talking.

• 1:18:24Speaker 01

  I think we can say there's over 5 million now.

• 1:18:26Guy Raz?

  All right, 5 million paid subscribers.

• 1:18:27Speaker 02

  Paid subscriptions, to be totally accurate, is distinct from subscribers.

• 1:18:32Guy Raz?

  And that that's bigger than, I mean, the Washington Post, the Atlantic, the New Yorker. There, there's a narrative that you often hear, and I'm sure you've heard, from people who really are skeptical of mainstream media organizations. And the narrative is, look, they lied about the Hunter Biden laptop, they lied about COVID restrictions. You know, they told us that that it was no lab leak. Do you guys think that as we see the influence of big media organizations, the CNNs, the New York Times, the Washington Post's decline, do you think that they're partly responsible for that? Or do you think that it's just that, you know,

• 1:19:16Guy Raz?

  the business model doesn't work anymore? Or maybe a combination of those things?

• 1:19:20Speaker 02

  I would say it is a symptom of the model, a symptom of the structure, rather than ideological preferences of these publications and the people who run them. And so while I think social media has created opportunity for the skepticism to arrive, it's actually created a market for conspiracy theory against the dominant media. I think it's actually more of a symptom of the structure of that economy. And that in this dismantling of that structure that social media has wrought, there is a whole lot of reorganization and confusion and volatility that is waiting for order to be imposed upon it again in a new way. But that's not going to look like the old system. It's not going to look like a few central pillars who get to be the ultimate sources of a truth.

• 1:20:04Speaker 02

  It's going to look a lot more distributed.

• 1:20:08Guy Raz?

  Substack is not yet profitable, which is not unusual, right? It's going to take some time. Based on your experience at Kik, Chris, you know, right? Things can always go south. And obviously, you don't anticipate it, but it can always happen. How do you protect the future? How do you build, let's say, the proverbial moat around Substack? There are competitors. You may not consider all the companies like Patreon or Ghost or Medium or Beehive or some of these other, even HubSpot. You may not consider those necessarily as competitors.

• 1:20:50Guy Raz?

  But how do you make sure that the momentum continues and what happened to Kik doesn't happen to you guys?

• 1:20:59Speaker 02

  You just worry about it very hard.

• 1:21:05Speaker 01

  Well, there's two things I would pitch. One is, you know, the advantage of having a business model is you can be in control of your financial destiny. And so we're not running the company to like turn a profit. But the thing that is true and we've kept true pretty much the whole time is we don't need to raise money again. We're not on this clock. We have like, we are in control of our financial destiny.

• 1:21:27Guy Raz?

  You have how many employees now, by the way?

• 1:21:29Speaker 01

  About 100.

• 1:21:30Guy Raz?

  Okay, so you're small. I mean, it's small and but efficient, right? Because in terms of the, what's generated, it just takes 100 people to do that.

• 1:21:39Speaker 01

  Yeah, but this is part of it, right? It's like you want to be in, you want to be in control of your, of your future. You don't want to be, you know, the, the best time to raise money is when you don't need it. And so you want to make sure that you're always in that position where you have a path to accomplishing your goals that is not like, you know, if you're, if it's possible to build a business this way, which for us it is, it's better to build it where fundraising is an accelerant, but not a necessity.

• 1:22:05Guy Raz?

  So my industry, right, podcasting has changed so much since it began, you know, back in the day where you had to plug an iPod into your computer and download some weird wonky thing, you know, there's, there are people like Marc Maron and Joe Rogan in the early days, Adam Carolla. Now it's a massive business. And so it's changing, right? The, the whole, and this is natural and normal. How do you see the Substack model changing? I mean, right now, most people, they might subscribe, they might pay for it, or they might not, but they're getting a, an thing to their inbox and a letter. There are some people who are also doing audio, some people who are making sort of these videos. So what is the, what does it look like?

• 1:22:47Guy Raz?

  What is a successful like Substacker going to look like in, you know, five years from now?

• 1:22:53Speaker 01

  There's a lot of other platforms and networks that are built around a format. Right? You know, Facebook does text and Instagram does pictures and Snapchat does disappearing pictures and podcasts are for audio and Medium is like, there's all of these formats. Other things are built around formats. Substack is built around you. It's built around the direct relationship. It's built around owning your audience, owning your work, having your own space on the internet. And so we are already live in a world where you can write, you can make a podcast, you can make a video, things that you used to need a studio and special equipment and a team to do are going to become able to be done automatically. You're going to be able to make a very high quality audio video thing from the palm of your hand.

• 1:23:37Speaker 01

  And, you know, the thing that we we want to do in Substack is just bring all of that power to the people making stuff.

• 1:23:43Guy Raz?

  All right. When you guys think about your whole journey, right? And I mean, even the fact that you met, you ended up working for doing some consulting work for Kik Hamish and you were on your way out, Chris. And, and, and then you started this thing, which really was kind of weird. And I don't know if, if I think a lot of people are skeptical. They were, as we know, as we heard. But now that you where you where you've landed 2025, you're, you know, you're eight years into this thing. How much of where you are now do you attribute to the grind and the work you put in? And how much do you think had the success of it so far has has had to do with just luck and circumstance?

• 1:24:21Speaker 02

  It feels like a yin and the yang thing to me, totally inseparable, that the luck has to go with the talent and talent has to go with the luck. And the greatest successes come when those two elements are perfectly in a mutual dance with each other.

• 1:24:34Guy Raz?

  Yeah.

• 1:24:34Speaker 02

  When we started the company, it was the two of us and we got the opportunity to build this thing. And it started to show some early signs of success. I said to Chris, like, how can we get to do this? How come like, not everyone else is trying to like, build this kind of company or takes advantage of this like, very obvious thing and these like, dynamics? And his answer was actually similar to what you said in your question was like, not many people have the ability to do this thing. You know, not everyone's happens to be in the right position to do it.

• 1:25:11Guy Raz?

  Chris?

• 1:25:12Speaker 01

  Is it luck or is it hard work? I think it's mostly a third thing. Which is just doing it. Most people don't do the thing. Once you decide to do it, you need to work hard, you need some luck. But the most of the great things in the world that don't exist are not because of a lack of talent or because of a lack of luck, but because of a lack of people setting out to do hard things.

• 1:25:39Guy Raz?

  That's Chris Best and Hamish McKenzie, co-founders of Substack. By the way, Substack has become the go-to launchpad for a new generation of media brands, including some big ones like The Free Press and The Dispatch. Both sites, not surprisingly, were founded by veteran journalists who left big companies to move to Substack. The latest, former Washington Post columnist Jennifer Rubin's publication, called The Contrarian, founded just days after she quit.

• 1:26:11Guy Raz?

  Hey, thanks so much for listening to the show this week. Please make sure to click the follow button on your podcast app so you never miss a new episode of the show. And also, please sign up for my newsletter at guyraz.com, or you can find it on Substack. This episode was produced by J.C. Howard with music composed by Ramtin Arablouei. It was edited by Neva Grant with research help from Iman Maani. Our engineers were Patrick Murray and Jimmy Keely. Our production staff also includes Catherine Seifer, Casey Herman, Alex Chung, Sam Paulson, Chris Messine, Carrie Thompson, John Isabella, and Elaine Coats. I'm Guy Raz, and you've been listening to How I Built This.