Building Substack | Sachin Monga (Substack, Facebook)

Sachin Monga is the Head of Product at Substack, a platform that I personally use every day, and love. Before Substack, Sachin co-founded an app called Cocoon, which he ended up selling to Substack. Before that, he spent over seven years at Facebook as a PM working on video and camera products, building out the developer platform, and leading the ads growth team. In today’s episode, we dive deep on all things Substack. Sachin shares what it’s like transitioning from a large product team at Facebook to a small growth team. He discusses how to work with a hands-on founder and why you must be comfortable with rapid change in a PM role. He also shares unique features of Substack that make it an optimized experience for readers and writers, how he’d like to see it improved, and tips for anyone wanting to get started writing online. Find the full transcript here: https://www.lennysnewsletter.com/p/building-substack-sachin-monga-substack — Where to find Sachin Monga: • Twitter: https://twitter.com/sachinmonga • LinkedIn: https://www.linkedin.com/in/sachinmonga/ • Email: [email protected] — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — Thank you to our wonderful sponsors for making this episode possible: • Retool: https://retool.com/lenny • Stytch: https://stytch.com/lenny • Vanta: https://vanta.com/lenny — Referenced: • Substack: https://substack.com/ • Matt Taibbi on Substack: https://taibbi.substack.com/ • Bill Bishop on Substack: https://sinocism.com/ • Jasper: https://www.jasper.ai/ • DALL-E 2: https://openai.com/dall-e-2/ • 1000 True Fans: https://www.amazon.com/1000-True-Fans-Kellys-Simple-ebook/dp/B01N9P9O4G • You Are Not Late: https://medium.com/message/you-are-not-late-b3d76f963142 • The Timeless Way of Building: https://www.amazon.com/Timeless-Way-Building-Christopher-Alexander/dp/0195024028 • Martyrmade podcast on Substack: https://martyrmade.substack.com/ • Colin Meloy on Substack: https://colinmeloy.substack.com/ • Ethan Strauss on Substack: https://houseofstrauss.substack.com/ • Kareem Abdul-Jabbar on Substack: https://kareem.substack.com/ • Dayne Rathbone: https://www.linkedin.com/in/daynerathbone/ • For All Mankind on Apple TV+: https://tv.apple.com/us/show/for-all-mankind/umc.cmc.6wsi780sz5tdbqcf11k76mkp7 — In this episode, we cover: (00:00) Sachin’s background (07:11) The evolution and structure of teams at Substack (10:11) What it’s like working at a smaller company with a hands-on founder (12:07) How to share in a founder’s vision (14:02) Why the rate of change is the most challenging aspect of the job (16:37) Why prioritization at Facebook worked differently than it does at Substack (20:03) How Substack thinks about prioritizing for writers and readers (22:17) Substack’s recommendation feature and how it came to be (27:13) How recommendations have led to an increase of millions of subscribers (31:34) Moving forward with network-driven discovery (32:17) The “build with” principle and the product lab at Substack (35:02) How Substack deals with negative press (36:45) The writer experience at Substack (39:13) The reader-focused experience on Substack (40:41) Advice for writers (44:45) Substack’s vision for making creation easier (46:39) Common mistakes creators make, and how product improvements could help in some cases (49:57) Why you’re not too late to join the game (52:52) Lightning round — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

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

• 0:00Speaker 00

  I really think that we're just starting into this golden era of what it might mean to be a writer on the internet. The economic model for supporting great writing on the internet has been generally pretty terrible for like the entirety of the internet's history. And in the early days of Substack, there was a couple of these glimmers of hope where you'd have people like Matt Taibbi or Bill Bishop, some of the early writers on Substack that were really well-established writers who were clearly just being undervalued and now could come to Substack and see their true value. And that was awesome. That was really cool to see. But in the last year or so, even the last few months, I think there's been so many really interesting

• 0:41Speaker 00

  success stories now from writers who might not even consider themselves writers, people who are able to make a living, maybe even make a fortune, just doing great work and not needing to have millions and millions of viewers or play the sort of attention games of other networks, but just do really high-quality work and have a relatively small number of people value it highly enough to pay for it.

• 1:06Lenny Rachitsky?

  Welcome to Lenny's Podcast. I'm Lenny and my goal here is to help you get better at the craft of building and growing products. Today, my guest is Sachin Monga, who is currently the head of product at Substack. Before Substack, he had a startup called Cocoon that he sold to Substack. And before that, he spent over seven years at Facebook, working on the video and camera products, building out the developer platform, and leading the ads growth team. In our conversation, we dig into all things Substack, what it's like to build product at Substack, how different it is to work at a startup versus a big company like Facebook, the future of the Substack product. We also spent a lot of time on what I venture to say will go down in history as one of the

• 1:46Lenny Rachitsky?

  most legendary growth features ever created, the Substack recommendations feature. Substack as a product and a company has changed my life and allowed me to do the work that I do now. And it was such a treat to be able to chat with Sachin. I hope that you find this conversation as interesting as I did. With that, I bring you Sachin Monga.

• 2:09Lenny Rachitsky?

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• 2:54Lenny Rachitsky?

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• 3:39Lenny Rachitsky?

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• 4:23Lenny Rachitsky?

  To get $1,000 in free credits, just go to stytch.com/leni to sign up. And that's Stitch with a Y.

• 4:34Lenny Rachitsky?

  Sachin, welcome to the podcast.

• 4:36Speaker 00

  Thanks for having me.

• 4:37Lenny Rachitsky?

  I'm actually really excited to have you on. I've told you this before, I've told the founders before, Substack has changed my life in so many ways. There's no way that I would be doing what I'm doing now if not for Substack and just like the magical combination of features that you all built. And I'm also just really curious about how you all build the platform, where it's going, how it all works behind the scenes. And so again, thank you for being here.

• 5:00Speaker 00

  I'm so happy to be here and that's so great to hear.

• 5:03Lenny Rachitsky?

  Just to set a little context for folks, can you just talk about how you got to Substack? You currently had a product at Substack. What was kind of that journey to Substack?

• 5:12Speaker 00

  Well, I joined Substack around a year ago now exactly through an acquisition. I'd started a company called Cocoon about three years prior to that with my good friend Alex Cornell. And Cocoon is not like Substack. It was a essentially like a little photo sharing app for close friends and family. But there is a common thread which led us to Substack, which was prior to starting Cocoon, Alex and I had both worked at Facebook for a number of years and had worked on effectively the same problem of helping people share more with their friends and family and had all these ideas for what an idealized experience might look like. And I just kept running into the wall that you run into when ultimately advertising is the business model that is powering this whole thing. And what that means is you need to accumulate a lot of time spent and attention

• 5:56Speaker 00

  and convert that into basically sellable eyeballs. But it's not that hard to imagine what like a better solution would be. It's just that ads as the business model made it really hard to pull that off. And so Cocoon was in a lot of ways like a journey to explore what that might look like for this one particular use case of just like helping you feel close to a handful of people. And we always looked up to Substack as a really good example of basically that same principle, which is if you imagine rewiring the internet around paid subscriptions, direct subscriptions between, in Substack's case, readers and writers, what could that unlock? And could it unlock a clearly better user experience? And I think, yeah, we looked at Substack as a real inspiration and an example of that really working out. And got to know the founders pretty well and had a few conversations

• 6:39Speaker 00

  and realized that even though the blogging software and a photo sharing app are pretty different, our underlying motivations were really consistent. And it was a bit of a match made in heaven. And the whole team joined Substack a year ago. And I've been privileged enough to get to lead the product and design teams. And it's been a blast so far.

• 6:57Lenny Rachitsky?

  And before your startup, you were at Facebook for a number of years, is that right?

• 7:00Speaker 00

  Yes, I started in 2011 there on the growth team and had the chance to work on a bunch of different teams there, growth, platform, ads, and then eventually the team we called sharing, which was helping people share more in the main Facebook app.

• 7:11Lenny Rachitsky?

  Sweet. I want to spend a little time on that, but coming back to Substack, I'm curious just how the product team runs. How many PMs do you all have? How is it structured? How are you thinking it'll evolve as you scale? What can you share there?

• 7:25Speaker 00

  Sure. Maybe to start from when I started at Substack, we had zero PMs. We had a handful of designers. We had maybe 15 or so engineers. I think we're coming to the close of this kind of one-time inflection point of becoming a product-driven company and having a product process and structure and PMs and full-stack product teams. And so when I started at Substack, there was really not much of this. And we're still pretty early, but we have something going now. So we have four product managers in addition to myself. And we have three essentially kind of like full-stack product teams now that have a PM and an engineering manager, a data person, or a designer, engineers. And things are starting to roll and we're like finally emerging from this transition phase and it's been super fun.

• 8:09Lenny Rachitsky?

  What are these three teams?

• 8:11Speaker 00

  The three teams are, we have a writer team that serves writers. We have a reader team that serves readers and we have a growth team that does growthy things. And I should mention, we have a fourth engineering team that's like the systems team that doesn't have a product manager on it, but is keeping the lights on and helping us scale.

• 8:28Lenny Rachitsky?

  Awesome. That makes sense. So you currently align it around the user, type of user, plus kind of the infra and platform stuff. Do you have a sense of where this might evolve over the next few years, just structure-wise? Do you think you'll stick to that? Do you have a plan of how this might radically shift as you grow?

• 8:43Speaker 00

  Yeah, I'm actually kind of shocked that it's lasted this long and stayed consistent. I remember at Facebook, we would change our team structure, what it felt like, every three months or six months and just have a reorg every once in a while. And part of why I think it's remained pretty consistent is exactly what you mentioned, which is The teams aren't oriented around product surfaces. Like, we don't have a team that's like the app team, or a team that's like the dashboard team, or the podcasting team. We have teams that are oriented around customers and solving a bit of a timeless customer problem. Like, we'll never be done serving writers. We just started, honestly, having a concerted focus on serving readers. Growth is never a problem that you that you check the box off on.

• 9:24Speaker 00

  So I hope that we are able to maintain this general structure. And I think as Substack grows and expands, I'm sure we'll have more than three teams. This is where we're at right now. But I really like the the focus on a customer and a timeless mission, really, rather than orienting around what might be a bit more of a ephemeral surface area or product du jour.

• 9:46Lenny Rachitsky?

  Awesome. Shout out to the writer team. Thanks for building all the awesome stuff that I get to use. And it makes sense why you are more recently investing in the reader team, because Substack has its magical advantage platforms have, where your supply drives all your demand. Like, I go out and promote my newsletter. People sign up for Substack. So it makes sense why there's not initially a huge focus on the demand growth, but makes sense to get there. And so it sounds like you are. Your app is awesome. One thing I wanted to touch on is you're kind of in this interesting position as a head of product at a small-ish company with a founder who's very product sense strong. And that's a classic challenge for a product leader to be in, where it's a smallish company, either a first PM or even a head of product, where the founder is very opinionated about the product.

• 10:31Lenny Rachitsky?

  I'm curious what you've learned about how to work in that environment as a PM.

• 10:36Speaker 00

  That's a great question. I don't know if I have the recipe for this, but I can just maybe share a few of the things that come to mind. But I think the first thing was really treating my role in the beginning more as a facilitator than a decision maker when it comes to product. I think the team was also small enough that everyone, in theory, could have a good sense of what everyone else was up to. And like a specific problem we had, I think, when I joined, was that we were just getting to the point where we wouldn't have one weekly meeting where Chris could be in the room. Chris is the CEO of Substack and the person you're mentioning. And like decide what we're doing in the next two weeks. Like we were just emerging from that phase and we had this problem, which was all of a sudden Chris didn't really know what all

• 11:18Speaker 00

  the teams were doing and the teams didn't really know what Chris had in mind for what they should do and what the vision was. And we were hiring really quickly and hiring people who might not have all of the context of being in the room with them for years and being in all of the all hands meetings. And when I first joined, I felt like my main role was actually just solving that. And if nothing else, if Chris could have a really good sense of what all the teams are doing and if the teams knew where he was coming from and could start to get better at modeling him and his vision, that would be a win. So for the first couple months, I'd say that was all I tried to do. I think now Chris and I have some reps under our belt and the teams have some reps under their belts too. And that trust just starts to form. We start the week, Chris and I, we sit down for an hour, we go through what we feel like are the big problems to focus on this week? What are the things we're worried

• 12:01Speaker 00

  about? We sit down at the end of the week and we check in again. And there's just a lot of open communication. I think that helps a lot.

• 12:07Lenny Rachitsky?

  Got it. So it sounds like the core of this is building trust, which makes sense. And the way that you've been building trust, one is just do it again and again. And then Chris starts to trust, okay, Sachin's gonna do the things that I think are probably the right things. And then you said you have this weekly meeting. Is there anything else that either tactically you find is a really important component of this relationship? Or any other lessons you've learned about just how to keep this relationship healthy and constructive?

• 12:33Speaker 00

  You know, one thing that I think about a little bit, because like any startup, there's going to be times that are really difficult, times that are really fun. And Substack is certainly going through this really transformative time. We're really evolving in a lot of ways from a tool into a network. We're sort of in the thick of seeing this vision through that in a lot of ways, Chris has had in his mind for like five years. We actually, we did a thing at an all hands a little while ago where Substack went through Y Combinator, I think it was, yeah, maybe now six years ago. And we watched the 60 second demo day pitch from like 2017. And what was so cool about that was

• 13:07Speaker 00

  We're actually doing all those things now that Chris got up on stage and talked about, like, you know, one day in the future, Substack's going to get into podcasting and we're going to have this network effect that helps writers grow by virtue of there being other writers in the platform. And there's all these things that like, we kind of couldn't do until we earned our place at the table and like the right to be able to do those things that we're doing now. And so to go back to your question, I think, I think that I really try to be mindful of right now is how do I get a really good sense of like, how do I catch up? Chris has been thinking about this problem for five times as long as I have. And if I can get a good sense of where his vision kind of starts from and catch up those few years and help the teams do the same, that'll go a long way. Because at the same time, everyone now is coming at it from a different perspective. We have a lot more data and evidence. It's

• 13:52Speaker 00

  really good to have people on the team that have come from other companies and can apply that perspective. It's a lot of, again, facilitation. And I kind of view that as a big part of my role.

• 14:01Lenny Rachitsky?

  Awesome. I'm curious, what are the biggest challenges with being in the position you're in? Like, are there any examples of, man, that sucked? Or if you want to go in a different direction, is there a certain type of person that just isn't a good fit for this kind of role, being a head of product at a smallish company with a very product minded founder?

• 14:19Speaker 00

  I'll start with the first one. I think the biggest challenge with this role slash company phase, like I mentioned, we're going through this one time transition from not really having a product function or a product process to having one is, almost by definition, anytime you figure out how to do a thing, you'll now reach this next phase of growth and like, it'll be obsolete. Like, something that I've repeated a bunch to the teams is, I'm never too worried if we have the perfect planning process, or the perfect execution cadence, or the perfect like, communication process. Like, whatever our process is, we're never going to have a perfect one. And even if we did, it would soon be obsolete because we did a really good job. And now we've grown 2X or something, and we have more people, and the process needs to change. The main thing I care about is, are we just getting

• 15:01Speaker 00

  better every week, every month, certainly every year? And I think that's easier said than done. Like, it sounds good in theory, but then when you're in the thick of it, and you're constantly basically feeling like you don't know how to do the thing, because as soon as you figure it out, it's obsolete. It's just really hard. I think that's true of basically just startups in general, high growth companies, doing the thing well means that you're not going to know what you're doing. And maybe that leads into my answer to the second question, which is, that's not really for everyone. I think there's almost like a personality type that has to be okay with. Being humbled all the time and feeling like you don't know what you're doing. And I think you could be an amazing product manager at a company that is a bit more

• 15:43Speaker 00

  stable and consistent and get really good at what you're doing. And someone who's going to be really good at a company that is on a bit of this sort of trajectory, for folks who aren't watching the video, making a motion of my hand that's like not growing too fast. It's kind of a different job. The rate of change is a huge factor.

• 16:03Lenny Rachitsky?

  The point you made about how things are going to keep changing as you grow, such an important point that I don't feel like comes up as much as I thought would come up on this podcast. Like, people are always asking me for advice. How do I structure my product team? How do I prioritize? How do I do planning? And the main thing I've learned is no matter what you end up with, it's going to change in three to six months anyway, because you're going to learn more. And so the advice is just do the best thing you can think of right now. Don't assume this will last anyway. And that's good enough. And there's never like the perfect way to do it. So is the best way you could do it at this moment? And then you learn how to evolve it.

• 16:35Speaker 00

  A hundred percent agree.

• 16:37Lenny Rachitsky?

  You worked at Facebook for, I think it was seven years. I'm curious, what were you able to take from that experience about how Facebook, in a massive company like that, builds product to a smaller company like Substack? What translates well? And then what just doesn't?

• 16:50Speaker 00

  Over time, I'm finding that less translates than I thought. I don't know how much of that has to do with Facebook specifically, though. And I'll maybe mention one thing. So, working on the core Facebook app, which was what I was working on for the bulk of my time there, Facebook may be the most extreme example of trying to solve so many different problems for so many different people in one tiny rectangle, basically, that a big part of the product manager's job in a situation like that is going to be managing trade-offs. It's a super fascinating, like, intellectual problem. And I think going back to the previous point, like, I think a lot of people really thrive in that kind of environment, where if we do this thing really well, it is going to directly trade off against doing this other thing. And it's not even like a sequencing thing.

• 17:34Speaker 00

  When you think about prioritization, sometimes you think, we will do this, and then we'll do this, and then we'll do this. At Facebook, say, sometimes it's, oh, if we do this, we just can't do this. Like, it's going to be bad for this other thing. If we put a watch tab at the bottom, will that mean that people don't get a marketplace tab? What does that mean for this whole org and like what the product is? And so I think when it comes to something like prioritization. It's a very different ballgame. There's certainly some things that that are consistent. Like you generally want to prioritize things that are going to be high impact, low effort. Like these types of product management frameworks, I think like a lot of it can hold constant. But when you really get into the object level, like what does your day look like? I think being a PM at a high growth, or I can at least just, I can't generalize this. But the job at Substack right now, it looks quite different than what I recognize as my job

• 18:17Speaker 00

  from Facebook circa 2018. And I think it's maybe even gotten more of the case that the PM's job in a situation like that will be navigating these types of internal trade offs. So I think on something like prioritization, very different.

• 18:31Lenny Rachitsky?

  Just to double click on that a little bit, the main difference you're saying is that at a Facebook, it's not like whether we do a thing, it's just like what comes for a second, third. At a Substack, it's like, we probably won't get to this for a year if we don't prioritize it now. Is that how you think about it? Just like the time scale on your trade offs?

• 18:46Speaker 00

  No, I think actually at Facebook, it's not necessarily whether we do a thing. It's not like we do this now, we do this later. It's doing this thing might mean we can't do this other thing at all. Or it'll mean that instead of that chart being steady until we make the number go up. Like it might go down by doing A, it might mean B is harder to do like forever. And so I think whereas at a startup, a lot of it is time. Time is the main variable. We can do this now and it means that we can't do this other thing until later. There's also an element of sequencing that matters, I think, a lot at a company like Substack that is in this formative stage of becoming an entirely new thing in a lot of ways. Like Substack started off kind of like a single player tool for writers. Like it was like software for writers.

• 19:26Speaker 00

  And if you describe Substack now as simply newsletter tool, like that would be kind of reductive. And it's really now much more of this ecosystem that's evolving in all sorts of interesting ways. And there is a bit of an order of operations at play here where doing something right now might unlock our ability to do something later. And that matters a lot in a situation like we're in at Substack.

• 19:49Lenny Rachitsky?

  Got it. So essentially there's a lot more one way doors at a larger company. And here you can make decisions more quickly, partly, but also you can go back. And there's not all these second order effects of decision you're making.

• 19:59Speaker 00

  I think that's right, or at least there are different types of second order effects.

• 20:02Lenny Rachitsky?

  Got it. I know at Substack, writers are like the beacon and the vision of making writers successful, helping people make a living writing. And so I imagine writers are the North Star, helping writers be successful. But is there anything more you could share about how you prioritize things that you work on within Substack? Like, how do you think about the North Star?

• 20:20Speaker 00

  Going back to your question about Chris too, I think Chris and Hamish and Jay, the founders, I think really start from a place of principle in a lot of ways. Like, why are we even doing this thing? It's not just to help writers make money. It's not just to unlock these cool things. It starts with like an opinion for how the internet should work, where people should be in control over their destiny to a much greater extent than has ever really been the case over at least, you know, the last 10, 15 years, where all of a sudden, everyone just started spending all of their time in a handful of these like public squares that were powered by ads. And when you think about what that means for Substack right now, that that means writers are in control over being able to deliver their best work

• 21:04Speaker 00

  on their terms to their audience, make money directly from their subscribers. And also that readers should be in control over their experience. Like, when you show up to substack.com, that experience should be something that you have a much greater degree of agency over. Or if you download the app than if you maybe opened up TikTok or something. I think where that leads you down from a prioritization standpoint is often starting from, okay, if we could do something in a bunch of different ways, is there a way that provides more control to the writer or more control over the experience that the reader has to them? And is there a way that provides much less control? And, you know, all things equal, like do the one that kind of holds constant this principle of control. We could talk about a few other examples like this, but I think from a prioritization standpoint, from a strategic standpoint,

• 21:48Speaker 00

  Substack is a pretty principled company. And I think it's been really fun and interesting to get to work in an environment like this and also see how it like actually can work. You are excited about recommendations, the recommendations feature, and we can talk about that in more detail. And I think that's a good example where there's certainly a way to do that, where where writers have the maximum of control and we picked that way, even if it might seem harder to pull off. And then that feedback loop of, oh, and that actually worked, is really awesome to get to experience.

• 22:17Lenny Rachitsky?

  Yes, I definitely wanted to talk about this recommendation feature. I feel like it's maybe the most underappreciated radical shift in Substack and just like platforms in general. I think this is going to go down as one of the most legendary impactful features of any platform or marketplace. I'm just putting this out there. It's like such a huge deal and I don't think people appreciate this. And just to quickly summarize what this is, essentially you allowed writers like me to recommend other newsletters that I specifically pick. So I picked 10 newsletters that I think are awesome. Once someone subscribes to my newsletter, they see these 10 as, hey, you should check these out. I think these are awesome. And it's very curated. It's there's no algorithm involved, which to your point is Substack's, I think, vision and mission is just avoid algorithms as much as possible.

• 23:02Lenny Rachitsky?

  So the reason I think this is crazy and amazing is at this point, 70% of my growth is coming from this one feature. There's something like 500 other newsletters recommending me. And as soon as the feature launched and you look at my growth chart, it's just a hockey stick starting that day. I don't think people appreciate this enough. And I'm really excited to just chat about how this feature came to be. And coming back to a point we talked about earlier, Chris having a very strong opinion about how to build product. Something I heard through a birdie is that Chris was not excited about this feature when it was proposed and it took a bit of pushing to get it out. So maybe we start there. How did this come to be?

• 23:39Speaker 00

  Sure. The way it came to be was that we noticed this organic behavior emerging, which was that a lot of readers of Substacks were starting to discover other Substacks. But the way that was happening was typically through the lens of that original writer. And this could happen in a bunch of different ways, right? So, you know, I think you've used the guest post feature to have guests write posts on your newsletter. And obviously that is a really good way for your readers to go and discover some of these other writers in a way that you're curating. There's some less obvious ways that this happens too. If you have comments on, which I think you do, if I scroll down and click on the profile of someone who's commenting on your post. It'll show me the other subs that person reads too.

• 24:22Speaker 00

  And again, this is like a very personalized and very writer centric way of doing discovery. At the same time, we talked about sort of the supply and demand side of the marketplace. Like the supply side of Substack has just grown over time consistently to the point where now there's like a huge amount of amazing writers on the platform and a huge number of collective readers on the platform too, that we knew that this sort of like cross pollination, this discovery loop could be a really powerful thing. So if you start from first principles and you're like, all right, how do we like help readers discover more things? The most obvious way to do this would be something like, here's some Substacks you might like. Based on what we know about your reading habits, here's like a few that Substack is just going to recommend to you. This is the kind of thing that worked really well and at Facebook in particular, I think I joined in 2011.

• 25:05Speaker 00

  It was definitely still during the era, I think Facebook maybe had just over 500 million users and was on this path to be to a billion and beyond. And this thing that we called PYMK, which was people you may know, this little unit that would show up in the newsfeed and it would just tell you the eight other people that like you obviously know because you all have a million mutual friends. Like that kind of thing drove a very non trivial amount of Facebook growth in the early days. And of course, lots of other products have done things like this. So we could have done something like that. But then going back to that principle of like, okay, well, if we were to do that and let's say we were to insert it at the bottom of our post or in an email or something. It's like clearly a thing now where the writer who owns that space is not really in control over what the experience is that they're offering their readers.

• 25:48Speaker 00

  And the reader who signed up for Lenny is now seeing these other things that have nothing to do with Lenny. Does that kind of break this control principle, like putting writers in charge, putting readers in charge? Okay, so then back to the drawing board. What would be the most obvious maximal way to just put writers in control? What is like the simplest version of this? What if we just ask writers, who do you recommend? And what if we just put that in the subscribe flow and just made it as simple as possible? And I think Chris's reaction to that originally, when that idea came up was, that's probably just going to be really hard to pull off, right? It's just like you need, there's a lot more things that have to be true. You need writers to opt in, you need to pick good people, you need to find a way to surface those recommendations to the readers in a way that's going to generate a good amount of surface area.

• 26:31Speaker 00

  And I think it was a bit of skepticism that something like that could work. But we tried it and it took off really quickly. And there was this virality at play now where when you recommend a bunch of people, those people will get an email that say, hey, Lenny is recommending you. And here's all the readers that he's sending you. And it created this goodwill viral loop, which was really interesting to see play out. And I think there was a bunch of interesting lessons in there. We could stick into anything that seems interesting. But I think crisis skepticism was not, should we do cross pollination discovery? Like clearly this is something that's working, but is this kind of thing going to work? Given how many steps are required for it to be true that this becomes really impactful? And it just turned out that it took off way faster than I think we had imagined.

• 27:13Lenny Rachitsky?

  Is there any stats you can share about just the impact it's having, what it's done to Substack?

• 27:17Speaker 00

  Yeah, sure. Recommendations specifically now have driven in the millions of new subscriptions for writers across the board, across, I think, like tens of thousands of unique writers that have received subscriptions from the recommendations feature. Of course, recommendations in particular are still just one component in this broader basket of network-driven discovery. And I think we recently shared that more than one in three new subscriptions across Substack are coming from the Substack network and around one in 10 paid subscriptions now, too. And these numbers are just, as you can imagine, growing up and to the right, getting stronger every day. And I think we'll have some more interesting stats to share on that soon.

• 27:58Lenny Rachitsky?

  Awesome. One thing I wanted to acknowledge, I think some people worry about this feature that it drives lower intent users. I find that not to be true. They're definitely lower intent, but it's not meaningfully and significantly. So the fact that 70% of my user growth comes from this feature and my open rates have only come down a little bit says a lot about just, it's not actually, it's like useful, really intentful people as much as it can be from someone that hasn't actually been planning to subscribe and just recently found out about it. It's really impressive how high intent they are, all things considered.

• 28:31Speaker 00

  Yeah, and you bring up a point too that leads into some of the next things we're thinking about here, which is that right now, most of the subscriptions that come from recommendations are coming from one particular flow in the product, which is when someone subscribes to someone else on Substack, they will then see a recommendation for Lenny. So it's being serviced to people at a moment where not only are they just hearing about you for the first time, but they might just be hearing about the recommending writer for the first time too. They're new subscribers. And so they don't have this longstanding trusted relationship built up yet. Of course, you have people now who've been subscribing to you for years and who trust you greatly and would probably take your recommendation very seriously. But the people that you're recommending are only getting these subscribers

• 29:16Speaker 00

  at the first moment that someone finds out about Lenny in many cases. And a big part of the next step of this product now is thinking about recommendations less as like a step of the flow and more kind of like a graph, a really interesting social graph that is being built where of goodwill and of influence and you now recommend a bunch of other writers. And there's much more that could be done in the network than just show some of those writers in the subscribe flow of lennysnewsletter.com. There's a lot more we could do there. I'm curious if you have any ideas, but we've got a bunch of ideas that we're cooking up that I think will not only drive more subscriptions, but also probably higher intent ones as well, because these are going to be people that might already have been reading you for years, who never right now would know who you're recommending.

• 29:58Lenny Rachitsky?

  No, no great ideas to share. I do find since it's only free subscribers, I have to do more work to upsell them to try paid. On the other hand, having a huge pool of interested people that aren't ready to convert yet is only beneficial. And when I send a free post and mention, hey, I have a paid subscription, you can get more, it works really well. This episode is brought to you by Vanta, helping you streamline your security compliance to accelerate growth. If your business stores any data in the cloud, then you've likely been asked, or you're going to be asked, about your SOC 2 compliance. SOC 2 is a way to prove your company's taking proper security measures to protect customer data and builds trust with customers and partners, especially those with serious security requirements.

• 30:42Lenny Rachitsky?

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• 31:26Lenny Rachitsky?

  That's V A N T A dot com slash Lenny to learn more and to claim your discount. Get started today. Something else I'll mention that I've learned to do is I feel so fortunate being early on Substack and having this thing grow so much, especially from this recommendation feature, that I'm actually getting pings from people regularly now. Hey, can you recommend my newsletter? It's like a really good growth hack on Substack right now to try to get someone, a lot of subscribers, to recommend you. So my system right now is I want to share the wealth as much as I can. So I rotate through different newsletters. I help get them, say, 1,000 subscribers, and then move on to the next one, assuming I like them. It's not just any random. And then so I can share the wealth with a lot of different newsletters and give people a platform, because I have this platform now, and that's been working really well.

• 32:12Lenny Rachitsky?

  The Robin Hood of Substack. Yeah, and I'm going to get all these DMs to recommend people if I'm unable to, I'm sorry. So you talked about how Chris was worried that this would not work, and that's interesting. And his point of there's so many steps that have to happen for this to be adopted is such a good one. In my experience, getting users to do anything is so hard to get them to click some buttons and fill things out. It's like rarely works. And it's cool that it really did work. And I think that was part of the early beta. And I found that it was a really thoughtful approach to how it was all rolled out. Where there's like a small group of users and writers that tried it out, see how it went, see what the impact was, see if there's any negative impact. Is there anything you could share about just the way this was rolled out that people learned about how to do this sort of thing?

• 32:54Speaker 00

  One of our sort of operating principles, I mentioned that we're going through this one time transition of figuring out how to become a product driven company and how to ship products faster, better, et cetera. And one of the principles, like I guess, in this playbook that we're trying to write is we call it build with writers, build with readers. In some ways, now I think about it, it's almost like a sub principle of the like, put readers in charge, put writers in charge. Like, how do you build product responsibly if you care deeply about that? One way to do it would be to, almost as a strong default, anytime we're going to make a fundamental change to how Substack works, do it in a way where we bring writers along. And in this case, this is still an optional thing.

• 33:34Speaker 00

  This isn't like changing how Substack works for everyone, but this is, we think, a potentially profound enough thing that the way we did this was not just roll it out for everyone, put a little dialogue in the dashboard that says, hey, everyone, now go do this thing. It was like, okay, why don't we call up 10 writers who we think might be interested in this? It's not that hard to just mock up what this could look like, get some feedback. This is the kind of thing that I think a lot of product teams would do. But then maybe a lot of product teams would be like, okay, we got good feedback. Let's just like build the thing, ship the thing. Instead, we just ran a little pilot and you and a few other writers were gracious enough to lend your time and talk us through how you would see this working and what you would want. We actually have now, we've set up something called the Product Lab, which I'm really excited about. This is, I think you're a part of it. I hope we asked you.

• 34:14Lenny Rachitsky?

  Yeah, I'm curious to see where this all goes.

• 34:18Speaker 00

  Yeah. And so this is just like an invite only little group of 100 or so writers that we know are interested in being on the bleeding edge of what Substack is. Becoming and specifically offered like we're investing a lot in just tools to help writers grow. And now we've got this little lab where we can kind of take a feature like recommendations to writers and get quick feedback. And ensure that we're never just like rolling something out to everyone without going through this step first. It's just been super helpful to have a bit of this infrastructure in place. And often the thing that we end up shipping on day one tends to be pretty different from what we had in mind before we went through this process.

• 34:53Lenny Rachitsky?

  Yeah, I've been through a bunch of those experiences and it always goes super well. And I've been through a few features that just didn't go anywhere and then they, nope, we're going to move on and not try this thing.

• 35:01Speaker 00

  Yeah.

• 35:02Lenny Rachitsky?

  Something else that always comes to mind with Substack is it's often in the news. Substack is a very popular topic amongst reporters.

• 35:09Speaker 00

  Turns out writers like to talk about writers.

• 35:11Lenny Rachitsky?

  That's right, especially a platform that might disrupt them someday or their friends have gone on to and they're maybe jealous about. I'm curious, as a product leader, how you deal with bad press, angry attention, things like that, just keeping people focused, keeping people motivated. Do you discuss stuff? Do you just like, yeah, how do you approach stuff that comes out like, oh, man, and keep people excited?

• 35:33Speaker 00

  The whole thing here is just like parsing out the signal from the noise. There's very little chatter in the blogosphere, media sphere that would actually impact our day to day when I think about it. And that's, it's not zero, right? Like sometimes there'll be something that ends up blowing up or that people are talking about that we should really take seriously and see how that might impact our strategy. But I'd say 90% of the chatter about Substack is going to probably ultimately just be a distraction to our product team. At the end of the day, that should just be focused on executing on the vision. And maybe my skin got thickened from working at Facebook during a bunch of years that, you know, actually when I started at Facebook, generally things were quite rosy in the press.

• 36:11Speaker 00

  But we certainly went through a bunch of different phases and a lot of the stuff that I worked on myself at Facebook ended up getting talked about a ton in the press negatively most of the time. You kind of learn to just. Keep your heads down and keep shipping and ultimately that's all that matters. And I think Substack is, I feel proud of the way that I think our culture is internally being formed right now. We tend to not get distracted.

• 36:37Lenny Rachitsky?

  Seems to be the case. I'm curious where you see Substack going as a product long term? What are you excited about? Where are things heading?

• 36:45Speaker 00

  Maybe I'll answer that in two parts. One from like a writer centric lens and one from a reader centric lens, which I mentioned is a bit of a newer thing for us. You know, from a writer centric lens, I really think that we're just starting into this golden era of what it might mean to be a writer on the internet. Like I mentioned before, the economic model for supporting great writing on the internet has been generally pretty terrible for like the entirety of the internet's history. And in the early days of Substack, there was a couple of these glimmers of hope where you'd have people like Matt Taibbi or Bill Bishop, some of the early writers on Substack that were really well-established writers who were clearly just being undervalued and now could come to Substack and see their true value. And that was awesome. That was really cool to

• 37:30Speaker 00

  see. But in the last year or so, even in the last few months, I think there's been so many really interesting success stories now from writers who might not even consider themselves writers, let alone well-established writers like Matt Taibbi or someone like that. People who are able to make a living, maybe even make a fortune, just doing great work and not needing to have millions and millions of viewers or play the sort of attention games of other networks, but just do really high-quality work and have a relatively small number of people value it highly enough to pay for it. And that's like a new thing. And so when I see the next one to two years play out for the writer's side of the equation, a lot of what we're going to try to do is just make it much simpler to get started,

• 38:14Speaker 00

  to have your Substack. If you have an audience anywhere, Substack's never gonna- Be the place where you have the biggest audience, probably, but it certainly should be the place where your most valuable audience comes home to, where they get your best work. And we're seeing a lot of really interesting success stories now of people that might have a big Instagram following or YouTube following and certainly Twitter following. We're able to kind of use Substack now as this home base, this place to try to accumulate their most valuable audience that they own in the sense that they get their email address, they can export them at any time and just build really simple tools to just help them deliver their best work. Could be writing, could be a podcast, could be video. We're investing a lot in some of some really interesting community features as well. You're a great example of this, where to call Lenny's newsletter simply a newsletter would be hilariously wrong at this point, right?

• 38:59Speaker 00

  You had, you think you mentioned to me you had 30 meetups around the world last month or something like that?

• 39:03Lenny Rachitsky?

  That's right.

• 39:04Speaker 00

  It's an impressive run rate of meetups. And I think seeing that unfold and seeing how the platform can support that type of community behavior as well is a big thing that I'm excited about, just more. On the reader's side, I think maybe to segue into that, I think we're, again, entering this little potential golden age of the internet for how you experience it as a consumer, where instead of just having a handful of feeds that are basically the same, that you could just like scroll through and consume videos of random people doing random things, not to say that's bad and that should go away. I do my fair share of just scrolling through my phone and watching random videos too, but it'd be kind of nice to have another place you could go to as well, where the

• 39:45Speaker 00

  best culture is being made and you have an extreme degree of control over what you see and who you choose to kind of let into that space. And you might not spend two hours a day in there and that's fine, but it might be the first place you go because it's where all the best stuff is and it's where your best communities are going to live too. And we kind of see Substack evolving not as some like new type of social media, but true alternative to how you might spend that most valuable slice of your time. And we just launched an iPhone app, I guess now it's been six months ago and it's going really well and we're going to launch an Android app very shortly. And we're pushing really hard on this reader experience as well. And I think it'll be radically different and much better one or two years from now, too.

• 40:28Lenny Rachitsky?

  It's been interesting to see a growing percentage of the great content that I come across be on Substack. And so I think that's a cool trend for y'all. For writers that are thinking about starting a newsletter, thinking about joining Substack, what sorts of advice, tips, guidance do you have for folks that are thinking about getting into the Substack world?

• 40:49Speaker 00

  My first piece of advice would be to just start it and see what happens. Start it. Have a way to start gathering subscribers, put a link to it somewhere, write one or two things. And if you're not much of a writer, try posting a video or recording some audio, turn it into a little podcast. Just start, basically, and see what happens and see what kind of interest there might be out there for what you have to say, especially if you already have a following on other platforms as well. I think that there's a real risk that if your entire following is locked into one platform, where you don't have a ton of control over your ability to reach those people deterministically,

• 41:27Speaker 00

  and certainly to monetize that in some way, that it seems like it's a tenuous place to be in the current age of the internet. And so I'd say just start. It should be really easy. Go to substack.com, press the "Start Your Substack" button and see what happens.

• 41:41Lenny Rachitsky?

  That advice may sound people like, "Oh yeah, that's not actual advice." But I will say that is exactly what I did and that's exactly how I got to what I do now. I had zero intention of ever doing this as a life, or like charging for writing that I'm writing. That's crazy. And just the fact that Substack existed and let me try stuff out for free. You know, you sign up, you start it. Like, my newsletter, it's called Lenny's Newsletter because that was like the default recommendation when I signed up. Because I told them, "My name is Lenny." And it's like, "Lenny's Newsletter." And I just, because I had no plan to do this. It was just like, "Let me just sign up and try blogging here for a little bit." And that little path, I think about Chris and Hamish and the founders,

• 42:24Lenny Rachitsky?

  mapping out a user journey of the vision of how somebody onboards to Substack, to go from never writing to like doing it full-time. And I feel like I went through that exactly, if they even had that, where like, I sign up just to try it out. I start writing consistently. It starts going well.

• 42:43Lenny Rachitsky?

  Then I think about charging and then I launched the paid plan and then that goes well and it keeps growing and then I do it full time. That's exactly what I went down and there's no world where I would have done this if not for those magical combination of features of just like a really simple blog and newsletter and collecting emails. And maybe monetizing down the road.

• 43:01Speaker 00

  Yeah, that's amazing to hear.

• 43:03Lenny Rachitsky?

  Yeah. So I think that just start advice is really spot on. Just try it out. See if it's something you want to do. I will say it's easy to start a newsletter. It's hard to continue a newsletter and the continuing is the most important part, as Seinfeld would say in that clip.

• 43:16Speaker 00

  I will say though, to that point too, that I'm really excited for what Substack can do in the product to make that easier in a way that doesn't cheapen the experience. So there's a bunch of things we could do to, you know, we could automatically post stuff to your readers. We could, we could do a lot of things. Kind of going back to the like, how do we do discovery? There's a bunch of things that would probably just work, but they would eventually kill what Substack is or have all these nasty second order effects and ruin this promise of putting writers in charge, putting readers in charge. I'm really excited and I actually view your Substack as a vanguard, as a very kind of leading edge example of this of you have turned your Substack into this, not just this thriving community of readers, but also of like

• 43:58Speaker 00

  contributors and creators, right? You've got these amazing people coming and doing guest posts. You've got the podcast going. You've got these meetups. You've, I think in a lot of ways, alleviated the burden of how hard it would be to just be writing a long form thing every day and doing that for the rest of your life. That would be really hard. That would make it certainly much harder to keep going. And not to say that it's, that it's easy now. I know how hard it is to do what you do. But I think Substack can do more to turn this ecosystem into a, to funnel this energy into ways for people like you to feel more like a leader of a space and a curator in a lot of ways and

• 44:38Speaker 00

  still deliver this really valuable service to your audience without having to do all the work yourself. And I think we can do a lot more to support that kind of thing.

• 44:45Lenny Rachitsky?

  Is there anything you could share about what sorts of things you're thinking there and what you might be possible?

• 44:49Speaker 00

  Let's see. Guest posts are working really well and I'll say that we have a bunch of ideas for how to make guest posts a much bigger thing. Right now, the way guest posts work, kind of like a Like an op ed or something like you invite someone to come and just write a post on your Substack. I think there's, there's much more we can do without getting into some of the specifics and, and scooping the product team that we're working on that I think could make it feel more like you've got a bunch of people who are somewhat more like fluidly able to contribute to your Substack and deliver value to your audience. And I teased this community stuff that we're working on a little bit, but we're piloting a feature right now. That's been working really well where writers can get a little bit of like, uh, we kind of view it as like the pub at the back of your Substack where people can hang out and chat.

• 45:31Speaker 00

  And the writer is still in control and kind of sets the tone and sets the rules and norms for the space, but can create space for their subscribers to participate and hang out themselves too. Those are two areas that we're investing in a fair bit right now.

• 45:45Lenny Rachitsky?

  Something that I imagine somebody suggested that I'd suggest you all look into a little bit is OpenAI assisted writing. I was playing with this product that is called Jasper and there's also like Copy AI. Where just like I put in the title of the post I was about to write and it just generated like a pretty good paragraph summary of what it could have been. And they have this whole feature where you just start typing and it auto completes things smartly. So that would be cool. I don't know if you want to go there, but it's pretty good.

• 46:15Speaker 00

  Seems like an interesting can of worms.

• 46:17Lenny Rachitsky?

  Right. Interesting can of worms.

• 46:18Speaker 00

  We did talk about whether we should change our default publication. You know, your default name was like, just like Lenny's newsletter and we probably gave you like a little red square or something as your default publication logo originally. That a Dolly generated publication logo service would be pretty cool.

• 46:33Lenny Rachitsky?

  That would be cool. Like if nothing else, just for ideas, but I would love that. Coming back to the idea of someone starting a Substack, so we talked about advice, which is like the core advice, just start and see how you like it. A big part of this is like, do you want to keep doing this? Cause again, it's easy to start, hard to keep going. And also you may realize I've created this job for myself I don't like. So that's something they should be thoughtful about, but on the flip side, do you see any common mistakes people make when they're starting on Substack? That you suggest they try to avoid?

• 47:01Speaker 00

  One thing that's kind of interesting here that I think we have a big opportunity to improve in the product is that there's going to be obviously varying levels of intent that people have when they hit that start your Substack button. Some people might come in being like, this is going to be my full-time job. I want to make this work. I want to not just be a full-time writer. I want to build like a media empire on Substack, right? There's certainly examples of that happening now and. You can imagine a version of our onboarding and setup flow that's like the media empire version of it. You can also imagine the version that's just, let me just write one thing. Don't let, don't make me make all these decisions. I just want to kind of like get in the game. I think that in general, a mistake that people might make is, I'll maybe flip it back at an anecdote related to what I heard from Chris when I was chatting

• 47:45Speaker 00

  with him the other day, that he had to convince you pretty hard to like turn on payments at all. Correct me if this is, if I'm spreading misinformation, but is that right?

• 47:52Lenny Rachitsky?

  That's right. Yeah. And Hamish too, like especially on how often I can take a break. He's always given me advice of you can take a break more often than you think. Cause I feel like I can never not do a week. So yeah, both those pieces of advice. Yeah, it took me a while to get over. Maybe I could charge for this and then maybe it could take some weeks off.

• 48:10Speaker 00

  Right, right. I think there's like a generalizable piece of advice here that might be the, my answer to the question of what's a common pitfall, which is people are really worried about how their audience will perceive them and like really ultimately their own worth, right? Should I send a newsletter three times a week into people's inbox? Is that too much? Should I ask anyone to pay me ever? Is that crazy? Am I allowed to take a vacation ever? Given that I've got people paying on an ongoing basis and is that like a bad service to provide if I'm taking a two week summer vacation? I think almost in all of those cases, and then you could imagine five more things like that, readers, especially the people that are subscribed to you, who are paying you,

• 48:51Speaker 00

  are pretty forgiving and are really there to support you and want you to take that vacation. And there's probably more people who would want to pay for you that just don't even know about you, that would totally pay if they could. And so, you know, go back to that kind of like spectrum of, am I just trying to write a blog post? Am I trying to start a media empire? It's kind of like, many people won't know yet. Just open up optionality for yourself and see what happens. And maybe don't be too worried about what your audience might think. And I think that maybe is one difference between Substack than something like Twitter, Instagram or something. Subscribe as like an action is pretty heavyweight. It's like a costly signal, right? It's not as easy as just like mashing the follow button on a bunch of accounts on Twitter or something like that. If someone

• 49:36Speaker 00

  is subscribed to you, they're kind of granting you right access to their brain. Is maybe the way I view it in a nerdy sense, right? And so what that means is not just like, I'll let you write your one long form thing once a week, but hey, you've got this other person that you think might have something interesting to say? Cool, let me know, I'm here for it. And I think writers underestimate that, basically.

• 49:57Lenny Rachitsky?

  Maybe three things I'll add to this, just for folks that are thinking about, should I try this out, should I not? One, when I joined Substack, I already felt like it was too late. And this was three years ago, I was like, nah, it's too late. Everyone's already got their big newsletters, there's no way I'm gonna make any sort of dent. And I think people feel that now, and I think it's also not true. I think there's so much opportunity.

• 50:18Speaker 00

  Hundred percent.

• 50:19Lenny Rachitsky?

  Two, when I got to a thousand paid subscribers, which feels very doable, I was making around a hundred K, which is exactly, I think it was Kevin Kelly's thousand true fans, like, it was exactly like, oh wow, I could make a living with a thousand true fans, for real. And it's shocking how much you can make with so few people that really care about what you're doing. So think about, is there like a niche or something you're excited about that you can find a thousand people to pay you 10 bucks a month? And you'll make-

• 50:50Speaker 00

  Mm-hmm. And what's, what's cool about that, I think now with Substack and with the network effect is like, if there's a thousand people who are gonna pay you 10 bucks a month, there's probably 2,000 and 5,000 and 10,000.

• 50:58Lenny Rachitsky?

  Exactly what happened to me, I'm like, if I hit a hundred K, holy moly, I'm good. And then it just kept growing. So that's exactly right. You think there's a thousand, but like the markets for these things are huge. And then-

• 51:10Speaker 00

  Yeah.

• 51:10Lenny Rachitsky?

  The last point maybe is, it took me nine months of doing it every week for free to get to a point where I felt like, I can keep doing this, I enjoy doing this, people continue to value it, where I decided to turn on paid. So it's a very slow and steady thing initially, don't expect it to just blow up, like just do it every week, see how it goes, see if you like it, see if people like it. And if they do, keep going. If not, you can stop. Like when I launched my newsletter, I tweeted, I'm just gonna experiment with this thing, no, no idea where it's gonna go, just try it out. So you don't have to set the stakes high when you're starting out.

• 51:41Speaker 00

  Yeah, I think that's exactly right. You mentioned Kevin Kelly's 1,000 true fans, which has become this like canonical piece of writing on the internet now. My favorite Kevin Kelly blog post, that's my second favorite. My first favorite is a post that he wrote called "You Are Not Late", which is exactly what, you can probably picture what he says, but it's such a compelling, persuasive argument for the thing that you mentioned, which is like- Obviously, he wasn't talking about Substack in his post, but he was talking about the internet and how in the grand scheme of things, how lucky we are to... I don't even know when he wrote it. Maybe it was probably 10 years ago at this point, but certainly at a time where a lot of people were feeling, oh, Facebook and Google and the internet's done. The battles have been won. And I wish I was, I wish I was coming of age, I wish I had graduated from Harvard in 2004

• 52:25Speaker 00

  or something. And it's just so wrong. Like, we are so early when it comes to how the internet will play out that I think getting to work on that in any capacity right now, getting to shape how the internet is going to play out over the next 10, 20 years is so fun because we are not late.

• 52:40Lenny Rachitsky?

  You're here. I know Marc Andreessen mentioned this too when he moved to Silicon Valley in the 80s. It's all over. It's too late. I missed the gold rush of tech. And it was just the beginning. Well, we've reached our, a very exciting lightning round where I'm just going to ask you a bunch of questions real quick. Share whatever comes up. Sound good?

• 52:59Speaker 00

  Sure, let's do it.

• 53:00Lenny Rachitsky?

  What are two or three books that you recommend most to other people?

• 53:04Speaker 00

  I will plug some books that have nothing to do with the internet or software or tech, but have been the most informative or instructive books for me, I think, in my career as a product person working on software, which are books about architecture and urban planning. And the reason why I find this field so fascinating is because for like thousands of years, people have been figuring out how to build spaces that help people interact with each other and build good spaces to occupy. And we've only been doing this for like, you know, going back to the Kevin Kelly thing, like for basically the blink of an eye on the internet and in the digital realm. There's one book in particular by an architect named Christopher Alexander, who sadly just passed away earlier this year. He wrote this book in the 70s. It's called The Timeless Way of Building. And this is the book that I recommend to the most people.

• 53:46Speaker 00

  I have like, I buy it in bulk and I just like give it away to people. And the basic premise of the book is that in the 70s, we had just gone through like a couple of decades of just mass-produced cookie cutter suburban house development in the US. And his premise was like, we've basically just lost the plot on this. No one likes living in these houses. And if you think about why these houses all feel bad to live in, it's because the people building the houses now, for the first time ever, are different than the people living In the house, it's these like developers, these real estate developers, these big companies mass producing these houses. But for thousands of years, we've figured out what makes a good house and the people building the house or the people living in it and they get that. But now the incentive structure got changed and it messed everything up.

• 54:26Speaker 00

  And I think there's a really interesting parallel there with the internet, specifically how the last decade or so has played out where the people building the spaces that we occupy are operating under a very complicated incentive structure. And it's leading to these suboptimal user experiences. And this is what we work on at Substack. This is what I think is fun to work on right now. And if you're working on something like this, I would highly recommend The Timeless Wave Building by Christopher Alexander.

• 54:51Lenny Rachitsky?

  Awesome. We're going to include that in the show notes for sure. What are two or three Substacks that you recommend most, speaking of recommendation features?

• 54:59Speaker 00

  I was just thinking about this because I don't write on Substack certainly frequently. And so I don't use the recommendations feature, but who would I recommend if I did, besides Lenny, of course? I'll share a couple of like random examples, maybe again, outside of maybe the tech product world. There's this guy named Daryl Cooper, who has a podcast on Substack called The Martyr Made Podcast that I've gone super deep into lately. And it's hard to describe. He basically takes a topic and he will produce the single best explanation of that topic you will ever find. Because you'll spend an insane amount, like probably like, you know, 10,000 hours per topic, figuring out, getting to the bottom of the story. So he recently did this amazing, he's doing a series right now on like the labor movement in America.

• 55:42Speaker 00

  And it sounds like a boring topic maybe, but he's just such an amazing storyteller. And he's, I think, a good example too. This could only really work if he had found, if he finds his thousand true fans as people who are just like, yeah, I'll just pay for this. It would be a very bad advertising business for sure. He publishes pretty infrequently and consistently, but it's just like the highest quality stuff. That's The Martyr Made Podcast. And since I know this is supposed to be a lightning round and I spent too much time on that, the two others that I'll just quickly throw out there. Colin Malloy is one of my favorite musicians. He's the lead singer of The Decemberists. He's doing a really cool thing on the Substack right now of just a lot of interesting behind the scenes, stuff on tour, publishing audio and video. It's been really good. If you're a fan of The Decemberists, I highly recommend. And one more, let's see. I've been really excited about Ethan Strauss lately.

• 56:26Speaker 00

  He writes a Substack called The House of Strauss. He's a basketball writer, but I think it's a cool example of like, he just has subscribers now. He can write about whatever he wants and he writes about a wide range of topics and they're all really fascinating and I love to see that kind of thing happen on Substack and in general.

• 56:41Lenny Rachitsky?

  That just reminded me, Kareem Abdul-Jabbar just recommended my newsletter in his Substack.

• 56:45Speaker 00

  Oh, man, congrats. How does that? That must be like a life achievement right there.

• 56:50Lenny Rachitsky?

  Yeah, like what the hell?

• 56:52Speaker 00

  Congrats.

• 56:53Lenny Rachitsky?

  Thank you.

• 56:54Speaker 00

  He's a great writer.

• 56:54Lenny Rachitsky?

  I don't know if he reads it. I don't know. I don't know what's going on there. I love it. He, uh, he has got a great Substack, by the way. I think it's, I think if you just Google Kareem Abdul-Jabbar Substack, you'll find it. On the recommendation feature, I was just thinking, you want to shout out the folks that built it, like the team?

• 57:07Speaker 00

  I would love to.

• 57:08Lenny Rachitsky?

  Let's do it.

• 57:08Speaker 00

  Yeah, it's too many. It was, it ended up being a company-wide effort, but the product manager on my team, Dane Rathbone, was specifically, I think, the spearhead behind the way that we built it, like you mentioned, that we went into. He was a really big proponent for that and Gabriel on our design team designed it and many engineers worked on it and it'll be hard to shout them all out, but I'd shout out Dane on my team because he ensured that we built it in the way that we ultimately needed to build it for it to work.

• 57:36Lenny Rachitsky?

  Thank you, Dane and Gabriel. Two final questions. Do you have any favorite recent movies or TV shows that you've watched that you love?

• 57:44Speaker 00

  Yeah, I just finished the latest season of For All Mankind and loved it.

• 57:49Lenny Rachitsky?

  So good.

• 57:50Speaker 00

  Yeah. Did you watch it all?

• 57:51Lenny Rachitsky?

  Yes. Oh, my God. That is, the last couple of episodes, you're sitting on the edge of your seat.

• 57:55Speaker 00

  I feel like in this season, every episode was like its own standalone movie or something. Like it really, it started slow, the whole show. I think the first season was a bit slow. When I recommended to people, I'm like, just power through it. But they really found their groove. I'm stoked for the next season.

• 58:10Lenny Rachitsky?

  Same. And final question, what's a favorite interview question you like to ask folks when you're interviewing them?

• 58:16Speaker 00

  I have a tough time answering this question because I have found that there's not one question that will get me the signal I actually want. Given how diverse the candidates' experiences might be in their context, if you're coming from a Facebook-type place or coming from a startup, I might need to ask different questions in order to get the signal I want. So maybe I'll answer it in that way, which is like these days, especially for Substack, what is the signal that I'm trying to get? And I think really for early-stage, fast-growing startup, that's like, you know, we talked so much about how different that is. We kind of just need people who can run through walls to accomplish big goals. And maybe grit and endurance in some ways and drive are like the words I would throw out there.

• 59:00Speaker 00

  I find it's really hard to have one question that will get that signal. You need to tailor it to that person's background.

• 59:07Lenny Rachitsky?

  All right, I'll accept that meta-answer. Sachin, thank you so much for being here. As I've shared, Substack is very near and dear to my heart. And I'm really thankful that you spent time to dig into a lot of these things that have been on my mind and I imagine will be helpful to a lot of other people. And so two final questions. Where can folks find you online if they want to reach out, learn more? Are y'all hiring? And then how can listeners be useful to you?

• 59:31Speaker 00

  First of all, thank you, Lenny, for being such an amazing Substack example setter. We've talked about you all the time, as you can imagine internally, and you've been so helpful to the company and to our product team. So it's been a real honor to get to come onto the pod and keep doing what you're doing. You can find me on all the various social media platforms. I'm not super active on them, I must admit, but maybe Twitter would be the one where I spend the most time, which is just Sachin Monga. My first name and last name is my handle. And I'll make one plug for a role that we're hiring for right now at Substack, which is a data role, a senior data role with kind of a product and growth analytics bent would be the specific sort of archetype we're looking for in this role. And if you are listening to the pod and feel like that might be you, I'd love to chat.

• 1:00:16Speaker 00

  And I think my email address too, I don't know if it would get shared, but it's just Sachin, [email protected]. So feel free to send me a note anytime.

• 1:00:24Lenny Rachitsky?

  Awesome. We'll include that in the show notes. Sounds like y'all are building some cool analytics features, maybe based on that role. I'm excited for that. And awesome, man. Thank you for being here.

• 1:00:33Speaker 00

  My pleasure. Thank you so much for having me.

• 1:00:37Lenny Rachitsky?

  Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.