My chat with Substack CEO Chris Best

All right, we've got a few people here. So we can get started. I'm here with Alex Heath, known for breaking tech news until recently Deputy Editor at the Verge. And now you've gone independent. You're officially a sub-stack bestseller. - Well, thanks Chris, thanks for having me. It's weird to be getting interviewed by you, but I'm here for it. Yeah, it's good to be here. - This is so much more fun. I can ask the hard questions now. - Yeah, it's your turn. It's my turn. If only I was good at this. So maybe the first thing I wanted to ask you is why did you decide to go independent? - Yeah, it's something I've been thinking about for a long time, over a year. I've had many friends who have gone independent and they've all loved it. They've all, none of them have gone back and at least yet, many have been doing it for years and would never even think about going back. So it's always been in the back of my mind and what happened is that over the last few months, I feel like certain years matter more than others. And this year, given what is happening in AI, how fast everything is moving and also just kind of where I was at in my life, I felt like I just, I can't wait anymore. I felt like every day started to feel like a week and every week started to feel like a month in terms of like time that had lapsed. And so I decided that I wanted to do the newsletter sources.news, which is on Substack and a podcast and launched them both at the same time. And ideally, they'll feed it into each other and help each other. And I was able to line up Zach for our first episode of The Podcast Access, which premiered last week. And that kind of gave me a deadline of, okay, I'm launching everything in September and just going for it. And yeah, it was like one of those things that like brewed for a while. And then it was like all at once crazy like within a few weeks, I'm independent. - So it sounds like that it was, you know, friends that did this, they seem to be having fun, they seem to be enjoying it. But there's also something, I'm hearing you say something like there's something happening right now that's kind of new and exciting. And then being independent is a better, more interesting way for you to engage with. Can you say more about what? - Yeah, I just think for where I'm at, I've been fortunate in my career to meet a lot of people and build a lot of relationships that I feel like I could take with me and into a new thing. And yeah, right now, I've just never seen the tech industry moving so fast and honestly, they're just being so much excitement. It reminds me of like the early app store boom. I don't know if you, if that analogy rings true for you as someone who is also a part of that, but like it does feel very unique right now. It feels like there's a generational shift happening, not just in media, but in just tech and the kinds of people that are coming in and making all these AI companies, it feels like every day there's some crazy new launch that I see on social of a new startup that's doing some either crazy AI wearable or assistant that's gonna change your life, it probably won't. But like, you know, just the energy and the interest in what AI is doing is very palpable. And I do feel like we're in this transition moment where the world will probably look really different in a couple of years. And there's a lot of questions about how legacy media will adapt to that world. And that's what we could do. I'm sure a whole hour plus thing on that. But like I do think in this era, individuals and individual voices that are bringing something original to the world will rise. And I think brands, you know, capital B brands, they had a harder time. I was actually at this dinner with Sam Altman about a month ago, it was kind of a viral dinner where he talked about the AI bubble and all that stuff. - I'm sorry, a viral dinner? - Yeah, do you remember all these headlines about Sam at a dinner saying like we're in an AI bubble or I don't know, it was a weird one. But the turn of phrase viral dinner is a whole, that's gonna stick with it. Yeah, I should have probably used a different phrase. But we were talking about this and he was agreeing that the way they view it as like individuals, voices will start to matter more in a host AI, post-AGI world than maybe the brands that we truly think of today. And so I think you guys were a great example of that already happening like in media. But I don't know, I would rather just be building something in this crazy moment for myself and being the driver's seat completely and get to experiment with all these crazy tools and changes that are happening. And that was a huge motivator, yeah. - Hell yeah. - Well, tell us about the new project, sources.News. If people still ask that subscribe button at the top of their screen, what are they gonna get? - Yeah, so it's going to be original, hopefully exclusive always or at least a little bit exclusive reporting about the tech industry and the personalities and the big products and companies to shape it. And it's really a kind of spiritual continuation of what I was doing at the verge for the last couple of years. I launched our first paid newsletter over two years ago called Command Line. And by the time I left it was very successful. And you have interviewed a ton of really interesting people in the tech industry and have broken a lot of news, leaked a lot of internal all hands meetings, product roadmaps, people news, stuff like that. And we were talking about this. I think as I was getting ready to launch up, I'm actually very inspired by what tech blogging used to be, I guess, like when I was coming up early, all things digital and then recode was a huge inspiration. I loved the aperture of it. It was very like trading, very like insideery for the people in the industry. It wasn't trying to be something more. It wasn't trying to cover politics. It wasn't trying to connect Silicon Valley to all these broader discussions that are super important and the verge and wired and all these publications I think are doing a great job at that. But what I actually see is a white space now to kind of go back to what tech reporting used to be, which is really focusing on the tech. I am a nerd about this stuff. Like I just tried Meta's New Display Glasses last week and my first story for subscribers was that hands on and then talking was up about it. By the way, they are good. They're fun. I mean, I said this on the access podcast too last week, like you can't not be a fan of technology and new things and gadgets and just not think they're awesome. Like, even if I don't know if they're gonna be saying that you use for hours throughout your day, this V1 version, but it's like a taste of the future for sure. And so I love that stuff. And then yeah, I'm not gonna be like farming of these companies, but like coming at it from a perspective of I love this stuff and I also wanna break news, I wanna, I just get energized by telling people something they had, they don't know and doing that for the most, you're doing that about the most powerful companies on earth right now feels like a very, especially in the age of eight, I feels like a great moment to be leaning in on it. So yeah, I'm honestly still figuring out like hosting schedule, cadence, like building the like products, it just happens fast. So like building the product of the newsletter, like what are the components? What are the, it's like a recipe, right? It's like what are the ingredients that are gonna be consistent versus not? I'm still figuring that out. So bear with me over the next few weeks. But yeah, you're gonna get at least a couple stories you can't get anywhere else about, you know, the most consequential tech companies and personalities of our time every week. That's the goal. - Sweet. - Yeah. - Hit that subscribe button. - Please. - Yeah. - If you're not being YouTuber every time I say that. So why'd you choose a sub-stack and how's it gone so far? - Yeah, I asked around a lot. I evaluated all the platforms. I'm also a nerd about the business of media. So it's something I've been thinking about a lot, even before I decided to go independent. And Sachin, your head of product is an old friend or remember covering his, when he went independent from Facebook and launched Kaku, which I think you guys then bought, which if I'm not mistaken, he came the seed of the app that we're using to talk to each other right now. So like he was super supportive, also on your team's been super supportive. And seeing, I think the network effects that you guys are starting to have with the app and the audience demand you have for the kind of content that I make. And evaluating and seeing like, okay, there's, you know, Eric Newcomers, a good friend. I think what he's doing with Newcomers awesome. He's a little more on the venture side. Is there something like that for what I do right now? I didn't really see it. You've got a lot of like people who are in the space, people who are AI builders or whatever who are doing their newsletters, or like pragmatic engineer, which is like more niche focused on engineers or Lenny who's huge, but it's like really. towards like how to be a better product manager. But in terms of doing the original reporting that I do, I didn't really see anyone doing it. And so it felt like a nice open lane for me, and you all were really supportive in helping me get launched really fast, which meant a lot. So yeah, I think every platform has its trade-offs, and I definitely have thoughts. I have concerns, but I think right now, you guys are at an inflection point, it feels like with the app. You know, as I was evaluating platforms, what I would notice is like in the evening, when like my wife and I are like embedded on our laptops or whatever, like working, I would look over, and she's on her iPad on sub-stack, like looking at interior design sub-stacks, like clothes, stuff, and she said something to me one night, she was like, "This feels like Tumblr back in the day." Like, I just love this. Like it makes me, there's nothing like this. And I'm like, "Oh," and like, and she's not a techie, but when I saw that, I was like, "Oh, this is like breaking out a little bit more than I even thought." And then I've seen you guys going up the App Store rankings in the last couple weeks, so I think the condo of all that in the app and the platform dynamics that are a play, and the fact that there seem to be a lane for me, that all factored in. Great, well, let's make it the center of the universe for tech journalism. Should be. Should be. Should be doable. Yeah, I mean, I do think it's, I do think it's, another thing is like just all the community stuff you guys are building is really interesting to me, and figuring it out, I don't, you know, I would hold up like Emily, Sunberg, the Queen of Stump, sub-stack is like maybe the best example I've seen of like doing a community engagement, but I definitely want to lean into that as well. And that was something that I feel like you guys are iterating on faster than the other platforms, so that was also a factor for me. But yeah, go ahead. Awesome. Well, I kind of want to talk about the tech journalism aspect, and maybe one way to this, you know, and you're about page of your new sub-stack, you talk about sort of your principles for your reporting process, and, you know, I think you do, it's like to me that you sort of approach this with some of the traditional ideas of journalism, and I know a lot of people in the world are skeptical about, you know, people who go independent, can you maintain those kinds of ethics? I know other people who are skeptical about, you know, so-called access journalism, and kind of having to like stay close to your sources, and, you know, play for access, that can be a compromising force. You, your, your newsletters called sources, your podcast is called access. Yeah. Do you feel attention there? How do you think about that? Yeah, I loved attention. I, we named the podcast is intentionally, it's very on the nose on purpose. I, it is, it is a very delicate balance that I've managed to walk for a while that I see a lot of people get tripped up on, and you're right, like, I do, I wanted to outline my reporting process early on, and I'll build that out. I'll build out a fuller ethics policy and all that. I'm just, I'm literally like, you know, trying to tread water right now, but I, I do think there's room for it. I think you've got like, I look at it as like two polar ends of the spectrum here. Like on one end, you've got people in traditional newsrooms who are fully firewold off from the impact of their work economically, the business model they're operating in, the broader macro business they're in, the media in general, and then you've got like, I would say YouTubers, right, on the far other end, who are, especially in the tech world, who, you know, the companies, like, there's many stories of like, they'll, they'll presubmit questions to the companies, right? The companies like basically control these interviews. They're not real interviews, and I do think there's an opportunity to use something in the middle that brings the ethics and the rigor of what journalism is at its best, and the awareness and the understanding of the actual business. And I think my audience should want me to know understand my business and to understand my advertisers, and so them to feel authentic and to feel like true to me. And also like understanding that I can have advertisers, I can work with companies and still keep like the essence of what makes good journalism there, which is like when I spell out, you know, it's like, you don't, you have to see questions ahead of time. You know, you can't buy my coverage. I don't accept money for information, which is oddly like a thing you get asked a lot. When you do a kind of reporting I do is like, you'll be talking to someone and you're like, they're maybe gonna give you something really juicy and then they're like, can you any? And like, I just, I don't do that. And I care a lot more about the impact of ethics and disclosure than the perception of it. And so I, I do think the work will ultimately be the thing that people can judge and they can say, this guy looks bought or not. And, you know, Met is a good example. Like I came out with access with the first episode of The Sock and I've been covering Meta for over 10 years. And the first time I got an interview with Sock, he literally started the interview by saying like, kudos because I had leaked their rebrands from Facebook to Meta like very recently, like a few weeks before. And he was like game recognized game. Like, I do think these companies respect journalism when it's doing its job, it's fair. You're not like assuming the worst and you're bringing new information into the world. Even when like it really messes up their launch schedule as it did for Meta then. But like, you know, you can't, I don't think you can find another reporter out there who's broken more Facebook news than me over the last decade. And then I'm also interviewing Sock. So it is a balance that's tricky, but it's one that I feel like I've managed to walk so far and I'll keep walking. - Yeah, that seems like the interesting, for me that seems like the interesting thing here. 'Cause there's many people in tech, I think, who have kind of just turned against the idea of journalism and they're just like the, you know, whatever. The press is so hostile. They're so crazy. They're so like just looking to paint everything with a negative brush that we should just like disengage. And just like, don't talk to these people. Don't give them the time of day. Like go direct, do your own thing. And I think there's like, you know, there's, to me that doesn't seem totally unreasonable. Like I kind of see where people are coming from. On the other hand, the idea that the thing you want is kind of just like pure cheerleading and boosterism and just like, you know, some sunny like we love this and we're all friends and we just won't do whatever you want. Even if not only would that be a bad product for audiences, I think, even the people themselves would get sick of that very quickly. There's not actually a market for kind of, I, you know, there's a questionably a market for cringe unquestionably anti-tech coverage. And there's definitely not a cover, there's not a market for like the other side for cringe unthinking boosterism. But it does feel like the middle is maybe under explored to me. Does that ring true to you? - Yeah, that's absolutely what I'm trying to do. You can see it when you look at these YouTuber interviews sometimes of like these tech people. The audience can see through this always. In the comments, you'll look and then, and then yeah, you can see it when it's the opposite end when it's like overly hostile and you're coming into like roast someone or destroy them. And like that usually can work with a subject once, right? So it's like it's not a repeat game. I'm like about having longevity in this career. And I've seen plenty of people have viral success as a journalist with that approach. It's very difficult to have that be your repeat game. And ultimately like I love tech. I love writing about it. I love the companies that make it up and getting like this amazing access either through the front door or the back door so to speak in terms of like how I approach the reporting. And I want to maintain that. And that doesn't mean that I can't be antagonistic to these companies. It doesn't mean that I can't break news that pisses them off. But it's about the approach and it's about how you do it. It's about your intentions when you do it and being fair. And I do think like being a little more restrained with what it has afforded me over the years is like when you do want to land a punch at lands because you're not doing it to score points or you're not doing it because it's like your stick. Like I would much rather say, I think Google and Apple's search default deal is bad for competition in search and like argue that out and like then say like Apple's an evil company, Google's an evil company. It's like at what level of the heat index are you wanting to play at, right? And you can have a lot of the same outcomes by just being a little bit with a better I think longevity to what you do if you're a little more measured and you do play in that middle ground that you're talking about, very cool. Yeah. - Well, what's next? What are your ambitions for the future? - I don't know. I've had it's been a lot of interesting, I felt a lot of interesting conversations with people who have been reaching out, we're excited about the launch. I definitely don't see it being more than me for now initially, but down the road, could I build a little team potentially? I've got a lot of ideas about how to incentivize talent in what a modern newsroom could be. If there's people who align with my coverage approach, I'd love to talk to them. But yeah, I'm trying to build a sustainable company that can support me, but also, like, grow beyond me one day, potentially, and I'm realizing very quickly, even after week one, that it's going to be a marathon, not a sprint, and it's giving me a new appreciation for all the start of the founders that I've been up over the years, because taking a bet on yourself is very nerve-wracking, and I'll wake up one morning, and I'll be siked, and I'll be so excited about the day ahead, like I was this morning, and then maybe tomorrow I'll wake up, and I'll be like, you know, what the hell am I doing? So yeah, I'm going into an eyes wide open, and luckily, no one's told me that they'll think I'll fail, but I think ultimately, the thing that's going to matter for me, and it matters for subscription publications, is just making content that you can't get anywhere else that resonates, and so that's what I'm really focused on is, like, can I build the audience, can I create a critical mass to people who work in tech, and are thirsty for this kind of coverage, and then go from there? So yeah, it's like one step at a time, man, but it's, uh, any advice, it's, it's a lot. You need advice, um, my, you've already done the most important step. Every time somebody asks me for advice, my first thing is like, just start, uh, the idea that you're going to like, you know, figure out all the beautiful things in your mind, and then launch, and it's going to be perfect at the start, and that's how it goes. I've never seen that happen. Everybody I, I, I've seen be massively successful at this, figures it out as they go, sometimes they launch multiple times, I had to spend a lot of time convincing Lenny to turn on page subscriptions back in the day, uh, she was very like, wasn't sure it was going to work. Would anybody pay for this, and it turned out to be kind of, you know, incredibly massively successful. Mm-hmm. But things are never obvious at the start. Yeah. There's always like, you know, a butterfly could flap its wings, and it'll, you know, you'll decide to do it, or you want to, or you'll twist one way or another. And so yeah, I think my biggest thing would just be, make the thing great. Don't be afraid to, you know, learn and change up and figure out what's working and kind of go, but I think the most important thing is, uh, just decide it's going to happen and make it go. Is there anything specifically on the kind of community building side that early on you advise to lean into? Like I've been looking at the chat stuff, um, but yeah, like is there something that you all have seen really worked, especially out of the, out of the gate on the community side? Um, chat is kind of, it seems kind of bymodal right now. I want to check that out. I'd like to get better. There's a subset of people, especially in like the fashion world where it's just kind of like completely off the hook right now, um, but you might see it, like you, you might see if that is like a natural feeling for your audience. Um, I would definitely like lean into the common sections. I would lean into notes like the stuff in the app. I would be unashamed about setting your sort of like rules and community norms, like part of the idea on sub stack is we're going to have a very sort of like pro free speech hands off policy at like the platform level, but that's, you know, complimented by your own ability to be kind of like the benevolent dictator of all of your spaces, and I would lean pretty hard into like just being there and hanging out with people and setting whatever rules you want to set. Um, because we can, we often see those sort of like comment communities, uh, be a thing that compounds in value over time. Mm hmm. This is one thing that I'm just about the product in general that I'm struggling to understand when someone follows me, is it the same as it's, is it the same as subscribing? Like, are they getting my emails now? Or is that a separate graph that's just sort of a platform? Yeah. We need to make this less confusing. It is a separate graph. We default to subscribing in almost all places. The one place we don't is if there's people that are kind of like doing bulk actions, we don't want people to like accidentally subscribe. And so there are cases where you can indicate like a follow interests. Um, they'll see you more in the feed, but they're not, they haven't like given you their email yet. We'll see all of the subscribe upsells. Okay. Okay. Yeah. That was the one thing I was like, I'm not sure what is follow the same thing or we have, and we have too many, we have too many downs right now. We're launching a lot. I mean, I saw that the trending sidebar got added to my homepage today. You're doing a lot of like discovery stuff. We're doing a lot of, we're shipping a lot of things. We just got to make sure that we like, simplify it back down every once in a while. Yeah. Um, I guess the thing that, so it's talking about like my launch again, like the thing that I'm quickly realizing is that for this to be sustainable and more successful for me than the cushy job, full time job that I just left. I need to do advertising, um, and I want to do it in a way that feels premium, authentic to me products that I would put my name behind, but, um, I see some sub sucks experimenting with that. And I'm curious like if you have any, um, advice for me or people watching about that approach and like, how you guys think about that, um, and how hands on our hands off you are there. Um, I think this is really interesting. This is something that a lot of people are doing sort of very successfully. It's something that we historically have not done much to help with. Like we're sort of like, hey, you know, people are doing it, but we're kind of not helping that much. Um, but I think right now we're sort of starting to talk to some of the people who are doing it and like look into other things we could do to make it easier, better because I do think, you know, a lot of the, a lot of top people are doing exactly to describe kind of like high end, thoughtful, you know, things that are, uh, not kind of tonnage slop that turns your audience into a commodity, but is like, hey, people are paying for this because it's a valuable thing because it has these standards, because it has all this, um, I think it's a valuable thing to explore and be happy to talk more about it. Yeah. Yeah. Yeah. It's just as I'm thinking about my free-to-paid ratio, I do think free, I think I want free-to-be large and to be, you know, even my first week numbers or it's kind of like 10X free-to-paid. Um, and, uh, I would like, you know, as a journalist, you get into this because you, you want to have impact, but you also want to have reach and the reach you can have with paid is obviously just more constrained, um, and it so happens that that larger reach that you get in free aligns well with, you know, a, uh, a sponsorship potentially, and so it just just felt like a very natural thing. I mean, I'm getting pitched from like companies that are, um, companies that are being started to help connect brands with people like me on sub-stack. I think that's like how I'm at the level of interest. I literally just got a message from an old contact like this morning who's doing this. So it's really interesting to see like all the attention on this right now. Yeah. There's definitely a there there. I think it's worth looking into. Maybe the, the, my parting thought for you on this is, um, I think people are tempted to, people are tempted to overrate advertising and underrate the subscriptions. Yeah. Um, cause it, it's easy to tell yourself a story where the advertising is going to be really easy and great and just sort of sail. And sometimes it does feel like that. And then in my experience, the advertising business is kind of the first to reveal about the business. And so it's like, even if it is great for a minute, it kind of flops up and down, whereas the subscription stuff, one thing that is really important is, even if you have paid subscribers, you can take your best and most impactful stuff and make it free. Um, you know, you want to have something for page subscribers, it's like, hey, I'm getting into the community. I've got some behind the scenes thing, but you can take your phone as that you feel are kind of like the most accessible or the most important and make them free. And that's actually a better strategy for growing your page subscriptions, then locking away necessarily, most of the stuff, like sometimes you want to put something good for the paid subscribers, um, but mostly you want to be putting stuff out there into the world for free, collecting the audience of people who find out that they value what they do. Then once they are reading and they decide that they love you, there's something eventually that gets them off off the, off the thing. But I wouldn't think of like your subscription audience as your own audience, even if you're describing subscriptions. That makes sense. I mean, with the, I'm starting to turn this into an interview of you, which I didn't mean to do, but I guess with the two minutes we have a lot of love to know, like big picture from you, like tech and media specific, the tech media part of sub stack is interested in tech and business that I'm and where do you see that going? What does that look like over the next like year, um, especially because sub stack is a lot of cultures now. It's a lot of different pockets of culture. So I'm curious about the tech community specifically, like where do you see that going? I'm really excited about it. Um, you know, we've, we've started to see that, that the thing you sort of described your wife, uh, uh, yeah, seeing the thing, like we're starting to see this in more and more pockets where there'll be kind of like this core of interesting stuff happens. Um, you know, there's a set of people there, the, the, the, basically like the app starts to get good around this topic and the thing starts to go. And I think we're kind of at the spot in tech media where we were maybe in like mainstream US politics, like a year, a year and a half ago. There's a bunch of really interesting voices, uh, I saw Mike Solana in the chat a little while ago. Um, there's kind of like this like early sort of like intellectual scene forming. There's interesting things happening. The audience is like starting to be here, but it's at kind of like the neck of the curve where I expect that this thing. can become a major part of the media ecosystem for this topic and this set, but it's in the early wrap phase of that thing right now in my estimation. - Well, I guess my time is good then. - Good timing. (laughs) - Well, I appreciate you doing this. This was fun to talk about this and I'm looking forward to the days and weeks ahead. Thank you, you too. - Good luck. - All right, thanks for us. Appreciate it. - Cheers. - Bye. [BLANK_AUDIO]