Celebrating & accelerating writers ❤️‍🔥 Bailey Richardson reflects on her time at Substack

Speaker A: Welcome to the Gigabyte.

Speaker B: This is a special episode of our show about ordinary people building extraordinary communities. I'm, um, your guest host today, Katie o'.

Speaker C: Connell.

Speaker B: I worked at People and Company and moved with the team Bailey, Kevin and Kai over to substack back in 2021 at after four years of researching extraordinary community leaders, coaching organizations at People and Company, and writing their book Get Together, Bailey, Kevin and Kai developed a process to help leaders answer one big question. How do you build a community? Three years ago, Substack presented an opportunity for the team to put the framework into practice and see does this really work? If you're not familiar with Substack, it's a publishing platform co founded by two engineers, Chris Best and Jiraj Sethi, and a journalist by trade, Hamish MacKenzie M. They came together to see if they could solve a problem helping readers pay writers directly. They launched Substack as a newsletter tool and proved when readers pay writers directly through subscriptions, writers can make a living or even a small fortune. And writers own their work so they can focus on doing what they care about most, not what algorithms or ads deem valuable. Substack's evolved from a simple newsletter tool into a network and a destination with the advent of new tools like the recommendation system and the launch of the Substack app. Along the way, more publishers have benefited from the business model that fuels Substack. Not just writers, podcasters, video makers, musicians, scientists and culture makers of all kind are making their homes here on Substack. And today, Substack Subscription Network encompasses more than 35 million active subscriptions, including more than 3 million paid subscriptions. You might subscribe or know some of the most celebrated writers and creators on Substack Margaret Atwood, George Saunders, Elizabeth Gilbert, Mehdi Hassan, Kareem Abdul Jabbar, or Heather Cox Richardson. But you might not know some of the most interesting, passionate and generous people that form the writer community and help it grow. Jolene Handy, who's been cooking through 1970s cookbooks from her 1970s kitchen in Chicago. Matt, who publishes Fogchaser, where he makes new original music every month from the Pacific Northwest in a new key Natalie Love Cruz, who's been eating her way through New York City country by country, A to Z. And Will Dow, who writes about the moon in the most beautiful way. And there are so many more with Bailey. Today we dig into what we learned after hosting a shared activity for 103 weeks and how we made the transition from online to real life as things became safe to do so after Covid Kevin asks Bailey for her revisions on the Get Together book, and you'll have to stay tuned in till the end for the answer. The episode was recorded on a bittersweet day, Bailey's second to last at Substack. She's been an inspired leader both inside the company and among the writer community, leaving her magic everywhere. If you've been a People and Company fan for some time, you know that communities feel magical, but they don't come together by magic. They take hard work. So let's dig into Bailey's magic and work at Substack.

Speaker A: We're here with the one and only Bailey Richardson as a special guest today.

Speaker D: Wow. Howdy. What's up? Oh, my God. It's going well. Yeah. Feeling good. Got my beige on. You've got your orange on. Kevin's got his beige on. Warm summer colors lighting up the room. Yeah.

Speaker A: Can you tell the people where you're sitting today?

Speaker D: I'm sitting on the 33rd street, uh, Kitty corner from the Empire State Building in Substack's New York office, where I will be employed for one more day, which is why we are doing this episode today. Crazy times.

Speaker C: End of a chapter, start of a new one.

Speaker D: That's right.

Speaker A: Indeed. Three years ago, you, Kevin and I joined Substack by way of People and Company. And you and Kevin had worked with Substack as clients and collaborators in the earliest days of the company. Um, and when the decision was made for People and Company to be acquired by Substack, you wrote a great post on the Get Together Substack, and you explained the decision of why People and Company was joining Substack. And you talked about how you and Kevin identified as writers, how writing the Get Together book was really pivotal because it helped you land these abstract concepts into firm language that you could lead clients through in the step by step process of building community. And you also talked about just being excited to apply this framework of building community. And so I would love to kind of go back three years in time. Can you tell us about that moment of joining Substack and what was on your mind, what you were most excited about?

Speaker D: Yeah, it's a great question, Katie. Um, wild to think back. Three years isn't that long, but it feels like a really long time. Um, yeah. To put you in the shoes of Bailey, Kevin and Kai. And unbeknownst to Katie. Katie, uh, three years ago, when we were trying to decide if we should take this opportunity to go work at Subsac, um, we had spent, what, Kev, like, five years by that point.

Speaker C: Yeah, it was like four and a half years by then.

Speaker D: Yeah, four and a half years. Researching communities, coaching community leaders, helping clients like Porsche's Driving club or like Nike's Run Club, uh, do their community strategies and build their communities. And Kevin and I had also, just like before that really had these pivotal hands on uh, community building experiences. So we went from knowing a community really well in a role of service to help people get people together, help people push their passions forward, kind of like helping other people do that for quite a while. And I was pretty resistant to going to work for a tech company honestly. Um, you know, I had worked at Instagram in the early days and gone through that whole VC funded hypergrowth acquisition thing. And there were some really fun parts about that and also some really challenging parts about working at a company like that. And I kind of had like washed my hands of an experience like that. Um, and then I got to meet the founders of Substack and the first employee, Fiona, and frankly I just thought that they were really stand up people. I really feel like, and I still feel this way, they have a solid value system that informs the business and how they run it. And it's more about the impact they're trying to have on writers and publishers lives and the information ecosystem than it is about fame or fortune like some other founders that I guess I've come across. Um, and I also got to see up close the impact that the subscription model and the product has on writers lives and the hunger and momentum that the product had in the writer community. So we sort of had this opportunity kind of fall into our lap where we could take everything that we learned at People and Company and maybe have a really beautiful place to go, apply all the things that we learned, uh, with a real live group of people in those early days, mostly writers on Substack, Um, and it's the journey's like not over, but I would say three years later I think we got to do exactly that. Um, so yeah, it was kind of like going back into uh, going back in, back home in a way. And Substack was really like fertile ground for going back and saying can we do this again but use our methodology and use all the things we learned to do it better.

Speaker A: Totally. And we're going to dig into all those things that you've helped lead in the last three years. But maybe just to zoom out for a second for maybe people who aren't as familiar with Substack or think of Substack in a certain way, I think of you as the mirror to the best parts of Substack. You can go deep on so many niches and get people excited about Facebook, things that you care about. And that's kind of what Substack is. It's a platform to people, for people to share something that they care about and gather people around that. Um, I know you to be someone who cares about so many cool things, from, um, women's basketball to surfing and liberty. Go, Liberty. And I learned so much from you. Um, and I love that you can, like, quickly find, grasp, and celebrate interesting people doing interesting things. One of your many superpowers. Um, so maybe for people who aren't as familiar with Substack or people who are still thinking of it as a newsletter platform, how do you explain what Substack is today and who's using it and what makes it most interesting?

Speaker D: Yeah, you know, when you work at a company, you're like, here's how we're going to talk about this, and I'm not going to do it that way. So, sorry, Substack Squad. Uh, I'm off leash, I guess. Um, I really feel like the most resonant way for me to describe Substack is like, blogging is back, baby. And I know that feels like reductionist, perhaps, because it's not just some blog from 2010 as a webpage. There's so much more now. There's video and podcasting and all the things that match the modern, uh, Internet. But really, the spirit of blogging came back with Substack, which was, I think the two key elements are bloggers are people that write about things they are nerds about. And a lot of times that's not like geopolitics or, like, American politics. It's like, hey, I've been reading all about the, like, jewelry that's being sold at Sotheby's from the 1400s. And here are some of the weird things people used to wear as glasses or like, I like ambient music, and I'm going to share a record with you every day. But I feel like I love people who get nerdy and get really deep into something. And it's one of the things that, like, really enchants me about human beings and strangers. And for most people, I think that's what Substack is a vehicle for. And weird. Through a combination of how media has progressed and how social media and feeds have progressed, a lot of that type of content kind of got eviscerated from the main spaces we spend our time. And Subset has figured out a Way to bring that back, um, by solving, I think, the business model question through subscriptions, which is I'm not going to go too deep into, but also by solving distribution through email instead of relying on feeds. So I think if you don't know anything about Substack, I think the thing you can know is like the spirit of it is very much like blogging. You are into a topic and maybe you find someone that you love who can be your trail guide into that topic and you go check in with them regularly while they get nerdy. Um, so I think that's kind of like what I really love about it. And, um, as I started to work at the company, I think the other thing that's extremely fulfilling about working at Subsec is see, seeing how much money writers make. It is like radical to see an independent creative person have a reliable BD salary, especially a writer in the United States today. And, you know, substack takes 10% of the revenue. Writers take 90% of the revenue. And I remember in the early days when our revenue was much smaller than it is today, logging into our dashboards and seeing how much money we'd paid out to writers and feeling like absolutely gobsmacked by that. And, um, that I think is another just key part of Subsec that's been radical and solving the business model problem. They're changing the value that we give writing in our society, in the economy, and changing kind of the viability of a creative lifestyle. So anyway, that's a lot, but I would say, like, bring blog. We brought blogging back and we made it like a career where people can make a solid income and in some cases wealth to go get nerdy and be sweethearted about the things they're passionate about. And, and I've totally adored being up close to that.

Speaker A: It is a special place to get a front row seat. Um, and you interviewed Nadia and Fiona, who were two of the early Substack employees when Substack was about three years old. Now Substack's about seven years old. And you spent a lot of time with them digging into the founding story of substance. And something that Nadia talked a lot about is how it's difficult for. To talk about a platform as a community. Substack's a platform. She said community means there's a reason why these people are here. Introspective of the platform. And when we first started at Substack, you spent a lot of time just thinking about what is community here. I think you boiled it down to three key Ways communities form. There's reader to reader community, there's writer to reader community, and then there's writer to writer community. Curious if you could tell us a little bit more about that and how you think about community on Substack.

Speaker D: Oh, great question. I mean, we. You were in it with me. Don't be pretending like I'm over here in the corner answering this question alone. You and I were working on this together. Um, yeah, I. I feel like, um, in those early days, I think we felt kind of torn between, okay, there's no community team, really. Now there's a community team. What m does that community team do? And I think, you know, in our book, we talked a lot about how you have to answer two questions up front. Who is your community? Who are these people? Who is coming together, and why are they coming together? And I think it could have been possible that we had spent a lot of our time, um, with cultivating and investing in helping writers build community with their readers. Like, maybe that will happen a lot in the future of Substack. We now have tools that make that way more possible than we did at the time. There's a thing called chat, where you can have subscribers talk to each other, which we didn't have that many years ago. Um, but we ultimately decided to connect writers to other writers. And I think some of the reasons we decided on that was one is, um, that's really, like, the unique role Substack can play. Like, the writer should be the one, I think leading their own communities, like the gathering of their own subscribers. They're going to be better at it than we will. Some will be naturally good at it. Some will be interested at all. Um, and then also at those early days, um, Subsack was a very new model. Not many people believed it was possible that you could make money writing with subscriptions online. Still, outside of the US A lot of people don't think that's possible. I'm sure within the US People still don't think that's possible. But Subsex made so much progress in terms of the belief that a writer could make money and that the subscription model makes financial sense. Since we started, um, but at that time, it was a really nascent model. Our team had very few answers about how do you substack, what the best practices are? Um, how do you convert a free reader to a paid reader? How do you find more free readers? What are the tactics that are working, what aren't? There were so many open questions, and the team at Substack had mostly up until that point, tried to answer those questions in one to one phone calls with writers or meetings with writers. And I think you and I, Katie, looked at that and we felt like we need to get writers sharing directly with each other about what they're learning and figuring out. And also like giving them a forum to ask us questions, ask each other questions. And you know, I think in the end the who we decided on, like you said, was connecting writers to other writers. And then the why we decided on was, was guidance. Like, people needed to develop, uh, more knowledge about how to use substack and we were going to need to work together, not just substack, offering insights to writers, writers offering them to each other to really rapidly grow the amount of knowledge there is on substack about how to use it. And today I think we're at the point which if we were consultants, uh, looking at the company, I think we'd be like, good job. Which is, uh, now there are people who teach subsack who are writers. They actually have websites and businesses where they teach other writers how to use subsack. There's teachers and consultants and people who independently have enough knowledge that they're almost like a subset employee, but they don't work here in terms of their ability to teach other writers. Um, so I think that, yeah, we invested a lot in building that knowledge base within the writer community and connecting writers to each other to answer questions. And um, that's probably like the long lasting impact and legacy that you and I will have to some degree. Um, maybe we'll see what the next chapter is for you. I can't wait to see. But that seems like the big, the big shift that we were able to be a part of.

Speaker C: Katie's going to be checking all the other boxes.

Speaker A: New leaders have been created. Yes. So, yeah, so we started with writer to writer. The why is guidance. And there's kind of like a couple different investments in like how we acted on creating guidance or sharing guidance with writers. Um, one was education programs, um, producing interactive programs that bring to life the guidance that our team had to share with writers. The second was developing and publishing educational resources. And then the third was encouraging cross promotion through community programs, events and storytelling. So stuff that really connects people to other writers makes independent writers feel less alone in publishing.

Speaker B: Um, there is a number of different

Speaker A: initiatives that took place over your three years at Substack. Um, I'm curious if there's one that stands out as really fulfilling the mission of the team to accelerate and celebrate the. These writers on substack yeah.

Speaker D: Well, let me just say that, by the way, Katie did most of these, so I was the happy manager that just got to watch and clap like a seal while you were doing most of this stuff. Um, so that has been, like, one of the absolute joys for me of this experience. And Kevin's nodding his head, uh, assertively, um, has been, like. It just been watching you do such a wide variety of community building, like, activities, and so many of them just, like, were huge hits. People loved and appreciated them so deeply. We had people asking about things you did three years ago, two years later, still wanting to, like, keep doing that. Um, so anyway, I just want to make sure you get your flowers. It's mostly about you, Katie.

Speaker A: Um, you're the fairy godmother advisor. None of this exists without your magic.

Speaker D: Um, yeah, but, you know, I. I feel like there's a couple of things that really stood out to me. Like, any community builder working on the Internet, you know, the things where you actually get to meet these writers in person, especially coming out of the pandemic. Um, the meetups that you had in New York City in bookshops, where E. Jean Carroll's there talking to John Paul Brammer, who's another, like, advice writer for queer people in New York City. And, like, just seeing these avatars come to life and seeing the kindness with which strangers treat each other. Um, and the mix. I mean, I. One time Patti Smith offered me a slice of pizza at one of these meetups, and I can't believe that happened in the room next to, like, you know, a guy writing about ski resorts who you interviewed for the Grow program. But I think that like, like, meetup thing never gets old, and I loved that. Um, and I also loved the Grow educational program you did, which was for the first time ever, we took all of the knowledge we had about running a substack successfully and did live sessions over the course of like, a month and a half with hundreds of writers from around the world who applied the biggest program substack had ever run to transfer that knowledge and get writers connected to each other, learning it, sharing and iterating with each other. Those were great. But weirdly, I think maybe one of the most memorable things was one of the simplest, which was, um, office hours. Uh, we did for, I think, how long, Katie? Two and a half years.

Speaker A: 103 office hours.

Speaker D: We did 103 office hours, which was basically every Thursday almost. We sent out, uh, invite at the same time to do basically, like an, Kind of like an ama, a thread where any Writer on Substack could come and ask us or another writer a question. And I wish I had the stats in front of me. Um, but I think, like, there were regularly days where we had a thousand questions or more, and I think that maybe you and I answered something bonkers. Like 50,000 to, like 100,000 questions or so. Like, I could be totally. I forget, like, the. This is where my brain's like, not the strongest everyone. But the stats were just incredible. And that was such a simple thing. It was just one hour a week. And friendships came out of that. Like, we got to know the community out of that. New ideas for resources that we could codify and share with the community came out of that. And also we did changes to the product out of that. I mean, I remember early on, Chris Best, the founder, came to office hours. The founders would come to office hours, the employees would come to office hours. And he realized he was like, too many people are asking about SEO. What's going on with SEO? And just in a, uh, just pushed forward. We got an SEO consultant. Now. Substack's SEO is amazing. We never hear about it anymore, but it just created this conduit between us and our writers and also helped connect them to each other. And I think I'm really proud of it because it was my favorite hour almost every week for so many Substack employees, it was their first opportunity to interact with writers, live. Um, and it was just so generative in so many ways, but it was extremely simple. So that, for me, I think I'm most proud of maybe. Even though there are a lot of other things that Perhaps were more 3D or more complex, I appreciated the power of the simplicity of that.

Speaker A: You.

Speaker C: I'm curious, what did you learn about our community building framework? You know, so in Get Together, we, you know, we codified and communicated this framework around, hey, to build a community, it's kind of like building a fire. You spark the flames, stoke the fire, pass the torch. You start by pinpointing your people, doing something together, getting. Getting people together, attracting new folks, etc. Etc. Creating more leaders. Um, and, you know, if you think about the, you know, the community building work at Substack as a testing ground, as a case study, you have any, like, revisions, you know, any notes, any like, you know, anything that felt like, you know, could be missing or that you elaborate upon or feel even more like, sure or passionate about based on your work over the last three years?

Speaker D: God, that's a good question. I'm, like, curious what you think as well, Katie, um, also, good job remembering the framework. Kev. You just ripped. Ripped all that right off the top

Speaker C: of your head, tattooed into my brain. You only got to read your book about 300 times. Read your own book times.

Speaker D: I just read it back to myself and fall asleep at night. Um, yeah, it's a great big question. I remember thinking after the first maybe six months, I was like, what have we done? I was like, oh, we've done the framework. We've done step one, two, and three. Um, so I think my general feeling is those core elements of knowing your who and why is a really sharp way to help you to decide how to get started. And then those key pieces of do something together and get people talking, those are the foundational things. If you can figure those things out, so many other things can come from there. And I felt like I was only, um, kind of like a deeper believer in all three of those things mattering, uh, after this. And I think, like, one of the things I'll say is office hours that I was just talking about these weekly threads where all writers could jump in, talk to each other for an hour or so, and then we wrap it up. Um, that, like, got people talking. And Katie, every week you would put prompts at the top where we would, like, encourage the conversation in certain ways, show people how to participate, role model, good participation. And those are, like, not rocket science, but if you can do it and you have a line that you have distribution to your community, it totally works. Um, and I think the other thing I'll say is it was also, like, a repeatable activity we did at the same time of the week, every week, uh, 103 times for two and a half years. And I've said this to people before, but I think when you're trying to, like, build a community, which means you're trying to grow relationships and connections within a group of people, could be a very big group of people, 20,000 people, whatever. You're trying to encourage more of those. You're almost like a barista at the local cafe. Like, your job is to, like, do the honorable duty of showing up consistently and, like, opening the cafe door every Monday, every Tuesday, every Wednesday, every Thursday, whatever. And I think Katie did that, like, with office hours, you know, it was like, you may not come this week, but we'll be here, and we'll be here next week, and you can drop off and come back. And I think a lot of business things, uh, are kind of like, counter that approach. Like, they're like one off dinners or something, or like one off marketing events or one off trainings or workshops one day and that's it. And I think we knew through the people and company methodology how important it was to design something that you can do over and over and over again if your goal is to encourage these kinds of connections and relationships between a type of person. So I think those things I really double down on. Um, and then I think, Katie, you've done this thing a couple of times where, because we had these lighter bonds that formed at office hours where people got to know each other's avatars, maybe kind of understood what each other was writing. Then you're able to do the next stage, which is maybe you host an in person workshop or like an online workshop and people recognize each other's faces, or maybe you host meetups and people can actually trust each other enough to get together. But I think that like, consistent, kind of light touch, very valuable activity gives you the opportunity to do so much more because people start to bump into each other and get to know each other. And so I think that was kind of the magic of like laying this foundation of connections. And then Katie, doing some really deeper investments that made people actually look each other in the face, talk to each other, live, make real relationships, make friendships that last to this day, um, that kind of like when you're dealing with strangers, kind of easing them into being able to do that is important. So I don't know, that's a little bit abstract, but does anyone else have another answer or a better answer than that?

Speaker A: I don't know if there's anything from the framework that I would change, but maybe things that have crystallized in different ways and maybe like, I think maybe just even that first step of pinpointing your people I think is one that we've like, come back to again and again of just getting m more sharp on who is it that we're bringing together? Because who has used substack has changed a lot over the last three years. Um, when we started it was a lot of like journalists and bloggers. Now there's people like, who are big TikTok stars that are starting substack. So I think keeping. Keep coming, continuing to come back to the who and figuring out especially kind of maybe going back to like, Nadia's point of like a platform doesn't inherently own the or like get the badge of we're a community. It's like now we're kind of tackling this question of like, how do we connect sub communities and like, how do we Connect different nodes of community. So I think that, like, maybe our who was like, more specific than when we started. Um, but over time, like, we've had to keep asking ourselves, like, pretty often, like, who is it that we're taking care of? Um, I think our why maybe has for a lot of these groups been similar. Like, I think guidance is the unique thing that we can offer writers, um, and then baking in, like, inspiration and fun to that where we can so that, like, there it does have that feeling of feeling less alone. Um, but I think, like, guidance is like the unique thing that figuring out an independent business on the Internet is scary and hard. And so that's what we can be is like a trail guide. And if we can connect people, them to other writers too, because there's only so many of us, um, I think that's where the value is. So maybe what I would say is just like the thing that I have come back to is that how many times you have to start over the framework, um, as you are at, like, maybe a company or at a platform that is growing quickly.

Speaker D: Yeah, that makes sense. It reminds me too, in the beginning, we were like, maybe it's celebration. Maybe these people are tired and they need to, like, have fun together. And we used to, like, host little celebrations for people that was like, you hit one year, like, you would do these live zoom things. And we were kind of like, meh.

Speaker A: I think the thing we learn is every time we send someone a celebration email, they're like, oh, great. While I have you, can you help me answer this question?

Speaker B: And you're like, the celebration isn't like,

Speaker A: like, just like, it's like, oh, like, you don't want to, like, celebrate your birthday when you're down in the dumps.

Speaker D: Like, you know, like, you're like, how do I drive to my birthday party? Please could you just tell us what that is?

Speaker A: Yeah, exactly, exactly. Um, but it doesn't mean the birthday isn't worth celebrating. So it's like, how do you balance the two and, like, solve the question so that there. There is a moment that is worth celebrating because that's the thing you're going to remember.

Speaker D: Yep.

Speaker A: Maybe that's a good subgregate of, like, our who has changed a lot. And I think that's in part because the product has changed a lot. Uh, when we started, I think Substack was pretty simply a tool. It was a newsletter, it was a website, it was a distribution tool, it was a payment processor, it was analytics. That was kind of it. Um, but Substack has been ushered into this new era as both a network and a platform or a destination. Um, a network I think is kind of began the day recommendations launched. It evolved with notes. Um, the destination kind of began with the app. And Bailey, you kind of thought a lot about the story and how we brought writers along with that evolution of the product. I'm wondering if you could tell us a little bit about that, how you thought about bringing the community along as the product changed in ways that sometimes were overwhelming or scary.

Speaker D: Yeah, I mean, maybe I'll just tell one little story which is, uh, I guess maybe a year or so into us being at Substack, we, um, decided to build an app. And that sounds kind of obvious maybe like everybody has an app these days. The New York Liberty has an app. I'm not sure why, uh, like everyone's got a friggin app. But for Substack it actually was kind of radical because the promise of Substack is you get your email addresses as the writer, you get a direct line to your readers and it is through email. And so introducing an app was kind of a scary thing for some of those early writers. Now I think later you might think that that sounds strange, but, um, at the time it was very real and there was a lot of, um, worry on our side of the house at Substack that we might upset or scare writers. Um, and I think Substack has had a great. The founders have a natural instinct in building with writers. If you know the founding story of Substack, it was literally built for like one writer, Bill Bishop, um, which we wrote about, ah, in the People and Company, uh, Substack, the Get Together Substack. So you can read about that if you want to. Um, but fortunately I think the founders have a real affinity towards bringing writers into the process. And one of the things that I got to do was run that beta for the app and kind of bring some of many of the people who participated in Office Hours or Katie's Grow programs and then also a lot of top writers, top publishers on Substack into testing the app and giving us feedback and giving them updates every week, getting feedback from them. And there was a huge part of the product that we had built that the community gave us, the writer community gave us feedback on. And we pulled back. There were features that when we launched the app we got critiqued about by writers and the founders pulled back. Um, but yeah, I think, um, we use that phrase in our book Build with. And now one of my secret joys Which I won't say to Substack employees, but I do take pride in, is that the whole company uses that phrase. We build with writers. Sometimes we build for them, but we also build with them. And, um, I think that that's been a real joy. And I think that in terms of telling the story of Substack, you can't make that up one sided. Like, the way that we told the writers about our products was informed by the things we know writers were scared of, writers wanted more of, writers needed more of from us. And so I think kind of having that open line of communication with them, um, throughout the process of kind of creating an idea for something, to testing it, to launching it, allowed us to go out the door with a story that was true and a story that felt like it reflected language and realities for our core customer instead of like kind of sitting in a boardroom and like throwing around zingers that we thought were cool or interesting. Um, so, yeah, so I think there's a number of things that we were able to launch that were actually quite spicy and change the nature of Substack. But because we invested up front in our relationship with those writers and getting their feedback, listening to them, adjusting and understanding their concerns and their priorities, we've been able to kind of radically change Substack over the course of the last three years from, like you said, something sort of like mailchimp to something much more powerful.

Speaker A: I think when we talk about building with too, we talk about how, like, using the product is a really key piece of that. And a year ago you started your own Substack Art Dogs, which has become beloved.

Speaker D: Okay, I didn't know that was a thing, Kev. You've been hiding that this whole time.

Speaker C: You know what the Japanese sound for a, uh, dog spark is? Wang.

Speaker A: Wang.

Speaker D: What?

Speaker C: Wang. Wang. Wang Wang.

Speaker D: It sounds closer to a duck, but I'm into it. Cool.

Speaker C: Art Dogs.

Speaker D: Okay, that's gonna be my new. About my one liner.

Speaker A: Wang Wang editing now, it's become so beloved by many, I think. People that we've gotten to know in office hours and at meetups, um, that have just shown up and become leaders in the community. Um, but you do this, really. These beautiful, beautiful profiles of your favorite artists from Matisse to Joni Mitchell. And it's not just dogs. It's turtles, cats, birds. Um, but I'm curious how your relationship to working for and with writers and creators has changed since you started Art Dogs.

Speaker D: Yeah, well, I'd say there's two things. One is Subsack's Amazing. And I know I have worked there for three years, but I, um, launched this newsletter about. By the way. Please subscribe. Uh, no, I. I launched this newsletter, uh, as kind of like a side project, and I was just really passionate about it. Um, which is another conversation I'm not going to go into. Um, and most. I. I basically have never promoted it. I've never sent an email to my friends that they should read it. I've. I, like, tweeted about it maybe once. Uh, just goes into the abyss of Twitter. Nothing happened. And on Substack without any effort. Now I think I have, like, almost 3,000 people reading it or something. Um, and each of those people chose very deliberately to subscribe to it. And some of the people I really look up to in the world are included in that. So, like, Wendy McNaughton reads my substack, and Elizabeth Gilbert reads my substack, and Debbie Millman reads my substack. And that blows my mind. And I think, for me, I just really enjoyed the fact that if you write about something that you really love right now, there's a community on substack of writers who are really interested in interesting writing, and you can get people to read your work that really like it and pay attention to it and give it care and thought. And, um, that is rare in this world. And so I think I got to. In one thing was experience what it means to have someone read your work that matters to you and how powerful that is and how subsack is offering something incredible to people. Um, so there's that piece. And I think the only other thing I would say is, um, I remember in our book we interviewed Mia Qualiarello, who was an early YouTube employee, like the first community person at YouTube. Shout out, Mia, you're the best.

Speaker C: Now a substacker as well.

Speaker D: Yeah, now on Substack. Now writing on Substack. And, uh, Mia told us a story about how YouTube changed their profile. Uh, page equivalence. It's like your channel page. They made a design change and people freaked out. And Mia said something to us, like, when you mess with that page, you mess with my stuff. It's like you came into my room and you rearranged my stuff. And I do not like that. And I feel like that, like, with kind of the, for lack of a better word, like, online Internet creator space, um, it's really personal. Like, writing is really personal. It is like you putting your ideas out on a ledge and saying, what do you think, world? And it's. Every word is specifically chosen and edited. Each paragraph space is specifically chosen and edited. And I think I realized when something would go wrong in the product that might seem very trivial to an engineer or even me as an employee. Like, oh, we have a weird spacing issue with images and captions for someone who just spent maybe 10 hours on a post and they previewed that post and it looked exactly the way they want it. And then they send it out to all these people, like, for me, that I respect, if it doesn't look the way I want it or the edits aren't reflected or, like, it's not the way I put my stuff in order, it can be really, like, dispiriting. So I think it, like, kind of gave me also just empathy for how personal the act of writing is. Each essay is like a personal. Yeah. Going out on a ledge. And it's very deliberate. People are very deliberate about what they make on Substack. And I think I could kind of understand the significance of some of the changes or tweaks that we think are small in a different way. I'd say,

Speaker A: well, let's do the shameless plug for artdogs.subset.com and you too can read along with Debbie Millman and Elizabeth Gilbert and all the but rest and learn about so many amazing artists and their pets. Your last big project at Substack was to create a unified strategy between our customer support team and Bridge the Gap and kind of create a unified strategy, like I said, between the community and education programs that we started on the community team, um, under this umbrella of what is called now Writer Success. Can you tell us a little bit how we arrived at this iteration of work at Substack?

Speaker D: Yeah, well, so I think you kind of touched on this, but we started out at Substack mostly working in community, and then we went into, like, marketing land. There was a lot of big changes we were going to make to the product at Substack, and we wanted to bring the writer community along in that, um, over the course of like, a year, a year and a half or something. But all these new things got introduced. Substack went from being an email service provider to a network. And we made a bunch of advancements in that from a product side of the house and a story side of the house. And as that kind of was becoming apparent that we'd made all this progress, I started thinking about, like, what problems I guess I personally was most emotionally lit up, uh, to solve. And I think the thing that really stood out to me was being in service of writers. In a pretty direct way. You know their names, you email with them, um, you help them with problems, you do educational programs for them was the thing that I felt most passionate about. And one of the beautiful things about Substack is the business model actually supports us taking great care of our writers. The writers who are earning money on Substack, they're paying us. We are like that. They're our partners in business. We want them to be extremely happy with Substack. They want. We want them to stay on Substack. They want. We want them to feel like no one is taking as good of care of them as we are. And so I felt like that orientation of service is something that I love. And I'm at a business that really backs that. It's not just lip service. And so we sort of decided, hey, let's go. Really take a swing at thinking about how we can take incredible care of the writers that are on Substack. Um, and that was a fusion of really taking our customer support team who had been in the operations side of the business, actually under Kev, and bringing them closer to other teams that were interacting with riders all day, every day, and then beginning to think about our work not as like, uh, just how many writers can we help in X period of time, but more about how many writers can we turn into, like, evangelists, just actually like promoters, NPS promoters. Um, so it was really about, like, how can we systematize taking incredible care of writers and making them feel radically well taken care of by an Internet company, knowing that if writers are really happy with Substack, that is going to help us grow. Writers are going to tell other writers, podcasters are going to tell other podcasters. And I think when you're an income, you're not an incumbent. When you're a startup, when you're going up against other email service providers or social platforms like TikTok or whatever, which is what Substack is doing. You need people to love you. We need nine out of 10 writers who take Substack seriously, to love Substack, to make a dentist in that distance, that differential we have between us as a small company and these big dogs in the industry. So, anyway, I really believed in that inside and out. And Katie, you have been a really key piece in us rolling out new poll, partner programming, partner success side of the business, which I'm sure people will see and learn more about soon. But, um, yeah, it's been, I think, really able to just dig deep into a problem area that I personally believe in. Find fascinating and deeply believe is critical to the business.

Speaker A: Well, maybe as we close out the hour and you close out this chapter at Substack after an amazing three years, um, I'm curious to hear, kind of like, what is the lesson you're taking in community building from Substack?

Speaker D: This is so, uh, arrogant. But our methodology works. Homies. That's what I'm taking from it. No, I mean, like, not that we're like the be all, end all or

Speaker A: something and we have like all these secrets.

Speaker D: But, uh, yeah, like, we came into Subsac being like, okay, we learned all this stuff. We've kind of told some other people how to do it. What if we go do it ourselves? Is this going to. We have perfect fertile ground. We have a great product. We have founders with good values who are great communicators. We have like a, uh, cohort, these creative people that we want to help. Can we do this? And it's not done. Like, we have like you said, Katie new. Who's new? Why's like new revolutions of serving people, bringing new groups into the fold. But there is a writer to writer community on Substack. Our competitors don't have it, I would confidently say. And we have one. And some of those people become real friends and like people that are a part of my life. Part of your life. Um, and that it feels very clear to me that that work was successful at Substack. Again, never ending. But we were able to take that get together methodology and apply it. And it was valuable for people. Um, so, yeah, I think that when you work at something like, I think I've mentioned this before, but I was one of the early employees at Instagram on the community team there when I was younger and I kind of felt like I was flying by the seat of my pants, uh, like just making the next most urgent decision. I didn't have a methodology. I didn't have a framework. I was just solving problems. And um, you leave something like that not knowing if what you did there will work again, could work again. And we didn't do the exact same thing at Substack, but having that get together methodology and all those learnings and insights and then seeing it work again at Substack has given me more confidence that this is something that you can do repeatedly. There is like, like we used to say fires are magical, but there is a step for making, step by step process for making a fire. You can do it. Someone can teach you to do it. And I think that's true for community building. Too, I think. So. That's what I would take away from, and it's given me a tremendous amount of confidence in our methodology and also just personal meaning. Again, just getting to meet people all around the world who are nerdy and really into something and showing up in good faith has been, like, a beautiful experience.

Speaker A: Well, you've helped spark some serious magic on Substack, and I hope you take that with you.

Speaker D: Thanks, guys. Thanks for being my ride or dies all the way through. And, uh, it's been fun to be back on the podcast with Katie as the host. What a thrill.

Speaker C: Yeah. Wow.

Speaker B: Thanks for tuning in to this special episode of Get Together. You can learn more about Substack at substack. Com, and you can follow along with Bailey's next adventures on, um, her own Substack, Substack. Com at Bailey.