Writing Hacks and Curiosity Gaps: Secrets Of Substack (feat. Linda Lebrun)

Hey everybody. Welcome to the Building Public Podcast. I'm your host, KP, and on this show, I interview world-class entrepreneurs, ambitious startup founders, creators, and builders on the internet who are boldly building the future in public. This podcast is my excuse to take you all on a curious journey to understand, learn, and hopefully be inspired by the worldviews, insights, and stories of these fabulous people changing the world. So far, I've gotten the rare privilege to sit down with incredible guests like Gary Vee, Alexis Ohanian, Kat Cole, Sahil Lavingia, and many more leaders. So check out the full podcast listing at buildingpublicpodcast.com. Now buckle up and get ready for our latest episode.

Hello everybody. Welcome to the Building Public Podcast. I'm your host. And today I'm joined by a special guest, a very special guest from Toronto. I'm hoping you're still in Toronto. I am still in Toronto. Yes, indeed. And I mean, I have so much to say about Linda, who's here. We're going to get into how we both connected and how our internet friendship formed and how she's been influential in my writing journey, in my being super active on Substack and my newsletter journey and so on. But without further ado, wanted to welcome Linda LeBrun. Welcome to the show,

KP. Thank you so much. This is really great. It's great to talk to you with the cameras running. We've had so much fun chatting before, just the two of us. And yeah, really pleased to be able to talk to your audience. So thanks so much for having me.

Of course. Linda, I like. I was joking at the beginning of this before we hit record. I feel like every time our paths cross, there's some kind of an inflection point in my career. And so last time when our paths crossed, for folks, you know, to give folks a little bit of context, Linda reached out from Substack where she works. And she was one of the— like, long story short, she was one of the influential people and probably the direct reason why I started to take my newsletter writing seriously on Substack. And so she nudged me into being more consistent and like bringing sort of all my tweets and all these like you know, content that I was creating all over the place into KP's column and the Building Public newsletter, which are now both running, you know, and thriving. And I went from a guy hating long-form writing to now 28 editions published in 28 weeks.

So fantastic.

I'm really proud. I'm really grateful for you, Linda. You want to share a little bit about how— I know that this is not an anomaly. This is part of your work, you know, part of your outreach. So tell us a little bit about what you do at Substack.

Yeah, I'd love to. I think there is quite a bit of mystery about Substack sometimes, and people wonder, so it's a platform, but yet you have these people who are trying to recruit writers, and what exactly is it? So I'm happy to make that more transparent and say what it is that myself and my few colleagues who do this task of writer acquisition and development do. So I, in a few sentences, the backstory is I never worked in the technology industry before coming to Substack. I worked in the investment business, but I was very attracted to Substack because I thought they were solving a problem for people who wanted to write online. We'll probably talk more about that later. And so pitched myself to one of the founders and ended up in this role where my job is to both help with writer development for people who are creators currently on the platform and also just go out and, you know, in the manner of an evangelist or a salesperson, if there are people who are writing elsewhere on the internet that might be a good fit with Substack, to try to talk to them about what this platform is and how it could help them. And Substack is not an email marketing platform. If somebody is trying to vend ecommerce products with an email list. We're not for that. What we are for is people for whom the writing itself is the product, people who would like to write online and invite subscribers to support them to continue their work. And it's a way to get your message out very easily without needing to know how to code. So it's a— you can tell I'm already telling the story even in just describing the job. It's a great story to tell. Right. And I've been there since March 2021. And it's also been a fun experience that many of your listeners will relate to of working at a startup where when I started, I was in the first 30 employees and now we're sort of closing in on triple that. So it's been during a high growth time, which has been a lot of fun.

Right. Yeah, I can relate to that personally too. I was probably number 27 at On Deck, you know, which was, which blew up and we grew to, I think, 350, you know, in almost a year. Crazy. There's a sense of autonomy and a sense of agency you get from being early. Mm-hmm. And just, you know, at least coming from a corporate life that I had before startups, I really, really enjoyed that transition and the switch up, you know, sort of what's expected out of you. You know, there's a lot of leadership, an opportunity to like lead and guide and be a great example that, you know, is very, very, you know, I think central to being in startups, right? Because really there's no playbooks. You're really inventing stuff along the way. How did you find, you know, as you got into your first startup, which is Substack, right? And a high-growth startup at that. How did you find the first 2 months Like, what do you remember about the first 2 months as you reflect on it now?

So I'm smiling because the most— is there such a phrase as pleasantly jarring? It was jarring, but not in a negative way. The most pleasantly jarring thing was going from a very traditional investment business financial services environment where it was baby boomer-aged people who were in charge and were the leaders to Substack, like a lot of startups, is a millennial-run company. And I am a Gen X-aged person, but a lot of the people who were in charge of the company are either around my age to about 10 years younger than me. It's a dynamism and urgency and very easy facility with technology and a million tools that are coming at you that you have to learn quickly. That, for me, it was, you know, to use a cliché, plunging into the deep end. But it also was very invigorating. And it was sort of what I wanted. Otherwise, I would not have done a career change to a different industry. Right. So, and just as you mentioned, where you have a lot of agency in a startup, In a startup, in my limited experience, nobody tells you no. If you're at a big company, you know, if Coca-Cola wants to make a tweet, it's going to go through 3 committees. Whereas if you're at a startup, I was sort of shocked to notice, like, okay, I can just tweet what I want. There's trust. I can— or if I have an idea, I want to, you know, can I have this event? Sure. How much money do you need? If it's a good pitch, it's reasonable. Nobody will stop you. The challenge is you don't have committees of people to do things for you. But if you're willing to take the reins, there's a tremendous amount of freedom. So that was super refreshing and cool. And so I'm still— I sound like I'm in the honeymoon phase. It has been 2 years and I'm still enjoying that kind of a work environment. And that was just completely new to me in my career.

I'm so glad to hear that. And I think, you know, I hope that even past the honeymoon phase, right, I— my biggest thing in the honeymoon phase was, first of all, this was so exciting. And I was like, I remember being like soaking in every micro moment, like feeling like, whoa, whoa, whoa. There was a lot of awe, a lot of like, whoa, this is happening. This is— whoa, this is how this— things are moving so fast. This is so fun. I also second-guessed myself and constantly felt like an imposter. I have like pages and pages of like journal entries where I was saying, these guys are really smart. Like, I was like constantly like writing stuff like, oh my God, like this person was smart. This person is smart, smart, smart, smart. Mm-hmm. And I think it was an important lesson as I reflect on it now that when you break into new ground, like in our both examples, you know, there are no pioneers in new territory, right? There are like— there's no— sorry, there's no experts in new territory. There are only pioneers. So part of the job is feeling that imposter syndrome because that is when you know you pushed yourself beyond a certain, you know, comfort zone. And but I had to make friends with that. And the reason I even bring that up is because that was the same imposter syndrome that I had when I was starting out on Substack, and when I was starting out the Building Public podcast. And it's the same butterflies in your stomach feeling. And now, by the way, the podcast, we just hit 50 episodes, which is crazy.

Wow, terrific.

So meaningful. I always told myself for years that I would start a podcast one day, but I never really got to it. And same thing with the newsletter. So I, what I remember from my early days of On Deck was no matter what I do in my future, if I'm really leveling up, it will feel intimidating and a little bit like an imposter. And making friendship with this, making peace with this is part of growing up, like evolving. Did you feel a sense of this? Like, was there anything that challenged you early on that you were like—

I think there was, but there is also a perspective change as you get older. You know, I, for example, was laid off during the— after Lehman, during the financial crisis in '07. Once you have experienced a near-death— it's not really near-death— a career near-death Yeah. Once you have experienced something happening and yourself not crawling into a hole and dying, but going on to something even better, then you realise that there's not too much to worry about. And once you also have the perspective of everyone is just trying their best, and anybody who seems like they're opposing me is not actually opposing me, it's just me putting that frame on them. They might not even be thinking about me. And if they are opposing me, it's because they might feel threatened. You know, this is sounding very sort of Zen-like, and it's hard to be that way and have that perspective in the moment. But once you think about all this, you no longer are having as much to struggle with the spotlight effect of, are people looking at me and judging me that I can't do it? I'll give a real-life example. So, being thrust into this tech startup environment, I was working for the first time fully remote from home. There were a lot— it felt like there was a new piece of software every day. And I had to log into Slack and log into Figma and log into this whole host of— and I didn't know how to use any of this. Right. There's no IT department. Everybody just figures it out on their own. They're engineers. It was sort of like a slog, and I was like, oh, other people seem to know how to do all this. What if I don't? But you know what? You just Google it and figure it out. And to tie it back to Substack, I always notice with writers who are able to proceed, and creators in general, despite the feelings of, am I inadequate? Will they like it? Oh no, every time I do a send, I have a few unsubscribes, which is normal, by the way. When they persist and keep going, it's because Because the, I think, cure for imposter syndrome is 2 things. First, break it into pieces. And second, make it simpler, make it as simple as possible, then make it even simpler. So it's like you take the— everybody probably who's listening to this podcast knows sort of the productivity basics and knows that when you're making a to-do list, you want to put your next step there. It's the same thing with any project with the Substack. What is the one next thing I can do? If somebody sat there and thought about writing 28 essays, or doing 50 podcast episodes, gosh, go back to bed. It's so overwhelming. But if you think about, I'm going to write something that's 2 paragraphs, and if I get tired after 1 paragraph, I'll just write 1. So it's breaking it into pieces and then having a very minimum viable product approach where it doesn't have to have the world's best logo. You can just maybe use an AI tool to make a logo or use a picture of yourself. It doesn't have to, you know, be perfectly planned out on an editorial calendar. You can just try to make one update and then give yourself some kind of a reward, you know, after you've done a certain number. So all of these tactics and techniques to make it simpler, make it less scary, and overcome that fear of not being enough and not being good enough, I think they work when you're at work doing a new thing at work. And I think they work when you're doing a project, whether it's creative project, starting a Substack, starting a podcast, whatever it is. These are— people don't have to make it up from scratch. These are the basics. And they do help people kind of go from zero to one, so to speak, just to start.

I think the The hardest part I've noticed is getting started in so many of these endeavors is because people— there's a good chance that you might be overthinking it even before you started. And oftentimes I think that is the biggest barrier. It's not that your work sucks, it's just that it's not present online. It just hasn't been shared. So I think— so let's actually reel that back to how you've been influential. So let's— can we talk about what— because I don't actually exactly remember what made you reply and say, KP, you got to be on Substack. And cause I think that there's a bunch of our audience who might be in my shoes who have been putting out stuff. Maybe they've been tweeting about stuff and they've been writing about, okay, I was, in my case, I was very engaged and active in the no-code niche and also in the building public as a niche. And, but I never really thought of long-form. I don't know why. I just never gave it a consideration. Never really thought about it. Maybe it was part of it was like, I don't know if people will like it or the same thing, like the starting problem, right? Mm-hmm. You reach out. What did you, what did you see? And what is like, I think, cause I'm trying to recollect from what you did there. What are— what's the missed opportunity, you know, for so many wannabe creators? I

think the missed opportunity— well, to answer first the question of what made me reach out in the first place, it tends to be a good precursor of somebody who will do well on Substack. Not necessarily if they're a freelance writer who's writing 3 1,800-word articles per week, but more if they have something to say and they have some kind of audience or ability to build an audience. This is why Twitter has been a fertile field for people then coming to Substack, Yeah. Because people will be on Twitter. They'll experience what we love about Twitter, which is communicating with others, being able to broadcast and get a reply back, being able to learn. But where Twitter stops serving you is you— it's very difficult to turn it into something that will support you doing all this work, i.e., monetize it in some way. And second, it's not an environment that you control. The social media site always is the intermediary between you and the audience. So what some platforms such as Substack do— I think Substack does it particularly well because our orientation is to be very good good at the getting you paid part and making it easy part is get the relationship to be direct and get it so that you can invite people to support you financially in a way that is elegant and does not require you to, you know, have the— it's no code, if you will. It doesn't require you to know how to do it. So reaching out to you was because you have— and a lot of people listening to this will know of you because they want to learn from you about how to build an audience online. You had been successful in what is not so easy, which getting people to listen to you, pay attention to you, building an audience online. Once somebody has done that, what is attractive about long form? I read where somebody said text is the universal interface. I think it was in a technologist context, but I loved the turn of phrase because text is— while there have been many people dismissing text, forget it, it's all about video and everybody's going to want to do short-form video, which is, which is one, again, short-form video, is fantastic. You can go and post a video on Substack, but writing seems to be very persistent for many tens of thousands of years in terms of a way that people convey complex and sophisticated ideas to each other. So even if somebody is not doing a lot of long form right now, sometimes it can be— we can see people who, if they have some kind of an audience elsewhere, they can do well on Substack because they're delving further into those ideas. And then the last thing is is you were speaking to a niche. It was not just very overview, general, you know, interesting history facts kind of— we all know these kind of Twitter accounts that are very, you know, here's some nice pictures of architecture, very sort of— they might have a million followers. When I look at those, I would tend to say it's not as likely that person would resonate with an audience that would be willing to support them for what they do. Right. It's great content to look at versus somebody who is, here's content you can use at work. Here's content you can use to make money. Here's content about a deep interest you have. Here's content about somebody who you feel very connected. They have a cult following. Those tend to be the sorts of things that people are more willing to pay for. So I've kind of touched on a bunch of things there, but the general idea of reaching out to you was you fit in many ways. And again, this might resonate with some people listening if they have something that is related to where they have— doesn't have to be world-class expertise, expertise, some expertise, and also a curiosity and an interest, you then invite people in to take the journey with you and share with them what you're doing.

So I have this framework that I use at the Building Public Fellowship, right, which is this online academy I started a week ago. And one of the things we were talking about there is you should really, when it comes to posting content or creating content, whether it's writing or not, I have this framework called 3 C's, right? People always ask me, what should I tweet about? What should I write about? What should I write newsletter, create letters about. I say 3 C's. One is credibility, something you have credibility on, right? So like in my case, building in public was easy because I was building in public for 3 years and that I could speak to it. I have so many screenshots, so many examples. I have receipts, as they say, right? So credibility. The other one is oftentimes people say, I'm switching careers. I don't want to talk about my fintech background. I'm not interested about that anymore. Then I say curiosity, because maybe forget the past, right? Think about the future. Maybe you're excited about generative AI. You know, that's fine. You know, maybe you want to talk about, I don't know, the future of remote work or something, you know. So whatever you might be curious about on the internet, you know, it's a great— it's a great asset. Curiosity is a great asset on the internet for a creator. The third thing I say is connection. You know, figure out what particular thing you want to talk about or what kind of people you want to build connection to. It could be a specific niche. It could be like, you know, female founders. It could be, I don't know, like immigrant founders in America. Speak to those audiences, speak to those people, because the more specific a niche you can be, the faster you can grow as a creator. And, you know, you know this from experience too, which brings Which brings us to the segue of niches. What's your— let's start with your spiel on niche because I think I want to add a couple of elements to it too. Should writers pick a niche and how should they go about it?

So I might have said this to you before because I love repeating this. Somebody tweeted and they said, if you are doing content, don't do content for bodybuilders, do content for vegan bodybuilders on a budget. Drilled it. And I always— it resonated with me because you hear it and you say, well, there's got to be very few of those. Drill down a few layers deeper, make it resonant with you and like yourself, and try to reach a smaller audience. It's highly counterintuitive because I have had— when people are starting on Substack, sometimes, even though really my job is not to give editorial advice, I don't walk in the footsteps of the writer or the creator. So we try to be humble with whatever advice we give. We try to make it based on best practices we have seen from others and on data and on evidence. But they will say, So if I have these 2 ideas, which one should I do? And their thrust sometimes is, well, perhaps it should be more general because then there are more people that it can reach. When, again, not to make a hard and fast rule, but much of the time it is better to have something more narrow. Then your task is, how do I find the individuals who will care about this? So the— and this is a really tough question because on the internet, it's never going to be easy to make $1 million. And there is no, if you build it, they will come. This isn't Field of Dreams. This is— competitive capitalism. So you do have to kind of think about, as you're thinking about what the niche is, so where am I going to go to find these? Right. To stick with my idea, vegan bodybuilders on a budget. If I go, let's say I go to bodybuilding.com and there's a thread there and it's for vegan bodybuilders and all the other bodybuilders are making fun of them. And I go in and say, hey guys, I have something where I'm going to be sending you some recipes that I have tried out in my own kitchen every week. They're all going to come and sign up for your Substack. So that, so I really I really think that it's one of those things that it's like, be consistent. It gets repeated a lot, but it still does really work quite well. And you'll see somebody and it's like, if you don't know a lot about a subject, like, I don't know a ton about crypto. So I'll be like, oh, well, that Substack is about crypto. But when I actually start reading about it, I'll be like, oh, well, you know, he's a Bitcoin maxi who's talking about the Lightning Network. And this is what he agrees with. This is what he doesn't agree with. And I find that, for example, CryptoKreia. If I try to put them all in the same bucket, they'll be like, no, I completely disagree with that guy. Why? Because the more they learn about it, the more they themselves fall into a niche because of their passionate interests and the set of opinions that they have. So in a way, the more work you do, I think sometimes the niche can find you. Well, I'd love to hear your perspective on this too. What advice do you give people about it?

I have this joke from Harry Potter, right? I feel like a niche is like your wand. The wand finds the wizard. You know, the wizard doesn't go look out. I mean, what you have to do is it's a combination of intuition and you have to start from the place of like, what am I so excited about, right? What am I so excited to talk about in the world? And when we both interfaced last time, at the time it was obviously top of mind for me was I think I was creating like maybe 50 tweets a week on building in public. Mm-hmm. It was very clear that I was obsessed about that topic and I wanted to write more about it. But as I look back to your point, point about Twitter being such a river of content, I couldn't really see anything where I could send someone any, like, an email, like a URL in an email about here's all the things that I wrote on this topic. So I was almost embarrassed that, man, I don't have anything long form that's like a series of essays. So I broke it down and said, I'm gonna just simply answer one question, but I want each week, and I would like do my best to collect all the resources that live in my head and summarize them and then write 2 lines of commentary on each paragraph. That's what I did. So I lowered the bar, made it easy for myself. But I have a real mega hack which I'll share in a couple minutes. when we talk about writing hacks because that was the game changer for me. But yeah, basically I simplified it and then I think that, yeah, the niche was very evident to me that people were telling me that this is what I— this is what resonated a lot with them. So even beyond no-code, so no-code content was great, but like people were saying, KP, we want you to teach us LinkedIn. But they would like bring me on all kinds of podcasts and they would like the topic would always be building in public, KP, you know. So I was like, hey, frick it, you know, like I'm just going to own this because it's being so competitive. The other question I have around for you around niches is on Substack, as you look at it holistically, do you think there's a lot of really successful niche Niche Substacks? If yes, then are there some examples that you can quote?

There are a tremendous number of niche Substacks, and I would say Substacks specifically, and newsletters, blogs, and publications in general. Because one thing that happens sometimes is people have an idea for coming on Substack and publishing, and they'll either say, are there other people doing this idea on Substack? Or they'll say, is there a desire or a gap, a need, a space for this on Substack? And both of those questions, I push back a bit because there is no such thing as the Substack audience any more than there is a Twitter audience or any more than there is any other platform, YouTube. There's no true one audience. There is just whoever might look in the entire span of the internet. So you are, and there are other newsletter platforms, publishing platforms. So I think across Across all of the places to put writing and creative content that we look at, people who drill down do very well. I particularly say that when it comes to niches, and I'm a bit repeating something that I touched on before in the conversation, if you are trying to do something where you will dedicate yourself to it as a full-time job, where you'd really love for it to be something that wholly supports you, often for the monetization part, it will be supportive and will help you if it's information that in some way people can use to help them at work or to help them make money. You are a perfect example. You are in a niche of the solo founder. So if somebody is an executive at a C-level corporation with 22 direct reports, they are not interested in your content. But if somebody is working a 9-to-5 job but really has a dream of building something of their own, They've taken steps. They want to know what's next. That is your audience. It's highly defined. So that's the other thing I'd invite people to think about when it comes to niches. So to give a couple of examples, there is a— here's one that I really like. There's a publication on Substack called Capital Account, and it is capitalaccountdc.com is the URL on Substack. You can have a custom URL. That's beautiful. They are 2 former Bloomberg reporters who left Bloomberg and they have created a Substack. Everything is behind a paywall. That's unusual. Usually when people do Substacks, they have some for free and some paid. You can also have everything for free and have people pay on a voluntary basis. What they have done is they put everything behind the paywall. They live in D.C. and they write about regulatory issues for a highly professional audience that needs this information for work. And their publication costs $200 a month. So I like giving them an example to Wall Street people because they might think, oh, well, I subscribe to a Substack and the Substack I subscribe to are $15 or $35 a month. So this is not for high-priced stuff. And I say to them, well, there's no definitional reason why it can't be. At the same time, you know, the many, many, many Substacks choose a more affordable price point because what they want to do is have a big tent and say, look, if you would like to support what I'm doing for $5 a month and $30 a year. Come on in, join the comment section, and, you know, we're gonna have a lot of fun. So there are, there are people, you know, another thing I'll mention for a niche, you know, I live in Canada, I live in Toronto, and this wonderful Canadian politics— Canadian politics, Canadians will laugh if I say that's a niche, but to the rest of the world, Canadian politics sounds like a niche. And he has a— his name is Paul Wells. He used to work at a magazine in Canada called Plains. That's sort of like the Time magazine of Canada. And now he is fully independent on Substack and he writes about Canadian politics. But the reason I like giving him as an example is because he's bilingual. He writes in both English and French. And if people Google his Substack, Paul Wells, they will see he has a section of his Substack that is all in French. So the way sections work on Substack is individual readers can subscribe to or unsubscribe from a section. So if somebody doesn't speak French, they can just unsubscribe from that section. But I loved seeing that. And there are people, you know, from, I think it's, you know, more than 100 different languages on Substack right now. But if you have a bilingual publication, you know, that's unusual. I can't think offhand of another person doing a bilingual Substack, although I'm sure there are. But for his readers, if they are bilingual, well, that's delightful for them to get Canadian politics information from a deep, deep expert who's been doing it 30 years, who takes it extremely seriously. And it proves out the point that when, you know, when Substack was trying to raise money to the very beginning of the startup journey of the founders, I think that a lot of the VCs that they pitched to said, well, nobody will ever pay for information on the— nobody will pay to read anything on the internet. Content is commoditized. Why would they? Well, there's a couple of things that are proof that people absolutely will pay. And whether it's $5 a month or $200 a month, they will be more motivated to do so if it is for a niche interest that they truly care about.

I loved it. And also, I actually, I don't know that I saw the part where you can specifically subscribe to a section on Substack. It's pretty cool.

Yeah, the sections. And we are, we're forever enhancing and upgrading and fixing Substack. I mean, that we are trying to run fast and satisfy everything that readers and writers specifically want us to do. So right now, if you want to— not to get this into a how-to, but if you go— if somebody is listening to this and has a Substack, if you go on your settings page, you will see where adding a section is called Add an Additional Newsletter. So add a newsletter to your newsletter, and it's a sub-newsletter. And the fact that it's a newsletter is what lets people subscribe to and unsubscribe from it. So, and we did this because otherwise, Otherwise, you're going to have people setting up multiple— rather than set up multiple newsletters, it would be better to maintain your one list, your one list, your one asset that you want to grow as much as you can, that you own and be able to customize, and the reader can customize what they get. So yeah, so I mean, the other thing I'd invite people— sorry, go ahead.

You know what it reminds me of? Obviously, like I said at the beginning, like the universe puts us into our, you know, puts us in touch just before me doing a new experiment. So yeah. This makes me wonder if I should have a paid section, ah, with this column as an extra section at the bottom and really kind of like create maybe some other custom content just for the paid audience along with the weekly that I do anyway.

Well, what I would, what I would say is you cannot— this really is building in public because this is just like if you and I were having a consulting call about how to do it. So for example, going back to Paul Wells, he can't say this section is paid and this section is free. What he can do is, and you may know So for any individual, once you have paid turned on on your Substack, for any individual post that you send out, you decide, is this post going to go to— what audience will see this post? Will it go to everyone? Will it go to my paying audience? But the thing that's underappreciated is we have a tool where you can send a post to your paid audience only, but you can send the first 1, 2, 3, whatever you wish, paragraphs of it to the free audience. Yeah. So, and people use that differently. I saw a writer the other day, and what she's doing is she's turned on paid. She's still sending out all the same content to everybody, but she's putting a section at the end that's a special sort of like behind-the-scenes VIP section, and that's after the paywall. And so only the people who are paying her will get to see that. So she— yeah, that's something you could think about.

Yeah, I could have a Loom video that's after that, or I could have something that's like a video component if I want to, you know, like, so the rest of it— so basically my whole essay could be free for everybody and just any extra things I want to say, like director's cut or like some extras that you would see at the DVD, would be probably— I can probably put them, you know, beyond that page or beyond that section, and then that would be turned on or that would be sent only to the paid folks.

You could have it such that some of the text was available to everybody but only the video was for paying people. You can also So with video, you could have, say, a 10-minute video that's only for people who are paying and then have the first 30 seconds of it that is for the free people. Yes. So something to look at there. Yeah.

Yeah.

So there's a Substack I really like called Views Are My Own. If people— Views Are My Own Substack, and they are a video-first Substack and they're really good at— they'll have a long interview video, but they'll just have the first couple of minutes of it that anybody can watch. I mean, this is the best performing conversion feature on Substack is, you know, when you're on your about page, or you're sort of making a post trying to woo people to go from being free to paid. Yes, that does work. But what works much better is if you have a post, and then you have sort of, hey, then, you know, the next thing I'm going to say is really the meat of this post, or the next thing I'm going to say is really special behind the scenes information. And then there is the block that says, you know, to read the rest of this, become It's that moment of FOMO that makes people go over the line and become a paying subscriber.

Yeah, that's how I became a paid subscriber to Lenny's Substack, because he would constantly have something that was like, that's so tempting for me to read. And I'm like, okay, yeah.

Oh, same here. Like, there's a Substack called Pragmatic Engineer, and the author is called Gergely Orosz. And yeah, and I'm not an engineer at all. I'm a non-technical employee at a tech company, but I pay out of my own pocket for his Substack. For his Substack, because the information that he has about the hiring developments, layoffs, what is going on at the big tech companies, and that filters down to smaller tech companies—it's unparalleled. I've never seen anything. I mean, I read the Wall Street Journal too, and his information is is better. His scoops are better on this subject again, on this niche subject.

So I think tell too. That's another thing.

He has intel.

He has all these friends and engineers who are all these you know at Stripe. and all these big companies. So he's got like really like sources and intel, you know. He's got the network. Heartbeat. Yeah, that's awesome. So let's talk about a few writing tips and Substack tips in general. Hopefully this can, this can be a, you know, uh, episode people can like look to learn from as well. So love to hear from you, Linda, given your exposure to like some of the top writers on Substack, if you can recall or can like say, I don't know, like 3 or 4 tips or specific things that you see top writers on What are some things that the top 1% do in any random order?

You know, I did a Twitter poll. Most of the people who would follow my Twitter account are Substack writers, not all are, but a lot are. And I was very curious because specifically when it comes to what tools writers use, I was wondering how many people still use Microsoft Word. I thought, oh, it's all, you know, maybe it's the millennials are not using Microsoft Word anymore. So I did a poll about what tools writers used. And the reason I mentioned that is because from the answers to that, I sort of said, do you write— do you— how do you draft your Substack posts? Do you use the Substack? About half the people said they use the Substack editor directly. And then it was 25% said they use Google Docs. And then some people use Microsoft Word. And then I said, if you use something else, reply. A huge number of people use Notion. It was a surprise to me. A lot of people use Notion to draft their posts. Some people use Obsidian, which is a note-taking that many of your listeners will know. What else What else did people say? Then there was a sort of a long tail of different word processor programs.

Evernote and Roam and others.

For sure. And they're using all those different ones. So I would say, you know, in terms of writing, the tool is a minor thing versus the discipline and how you write it. I would say that people use whatever tool is most amenable for them. If you want to keep it super simple, there are many people who are top, top Substack writers, top of the leaderboard, who are writing posts right in the Substack editor. Yeah. You can go ahead and do that. When it comes to editing, I think that often people will, and I include colleagues of mine, we within Substack internally, we all, most of us do a lot of writing. Many of us have a Substack, whether it's sort of internal. Yeah. I mean, this creates a lot of empathy with, if you can't imagine somebody working at Instagram and not having an Instagram, so we should be using the product. Right. So I think that giving the work to somebody else and having a second set of eyes, not an innovative idea, But having somebody else read it, give you some feedback, even if it's not a professional editor or proofreading, the more important thing is to have some other second person read it before. When it comes to, you know, stuff like coming up with ideas or how long should it take you to write or how do you brainstorm, I— my perception is that just, it's just massively idiosyncratic and everybody has different things that work for them. You have people who, you know, there are— we talked about sort of imposter syndrome and and feeling like you might be seeing somebody who's in the 10th year of their journey and you're in the first year of yours and you feel like, I should be like him. I think there's a dynamic where people might disproportionately follow Substack writers who are really successful. They have lots of comments, they publish consistently 3 times a week. Don't feel like you have to publish 3 times a week. If it is once a week, having a regular cadence is more important than having a, a massive volume. So yeah, I honestly couldn't say any sort of tip like, well, your post should be exactly 1,500 words long or before 9 AM Wednesday. day is the best time to put it out, that it would be deceptive to have anything so rigid just because I've seen such idiosyncratic approaches work. But I'd love to hear like, what have been your hacks and tips that have helped you to do more long-form writing successfully?

Yeah, I mean, so let's talk about Substack tips alone. Actually, I don't think I do anything that's out of the ordinary on Substack, frankly. And I'm one of those elite people that you said who write drafts with—

Well, that's good.

So I actually don't go on Notion. I used to, I used to try it like too much before. You know, really taking it seriously where I would like write like write drafts on Notion or Google Doc and I was like going to comments and all that. I'm like, I don't do any of that now, you know, and I just like, I just go to the drafts. I mean, I just go, oh, new post and just write myself a little outline on the top and 4 bullet points about what I want to say in that thing. And I just try to like write paragraphs that line up to the outline. That's it. Very simple. And I separate my writing time from editing time. So I write a separate day and then I edit on a different day. Substack-wise, I don't think I'm doing anything fancy. Actually, I try very hard to not tinker with it too much because it's a never-ending loop where there's a tendency that you can think that, oh, you can tinker your way to greatness. And I feel like, you know, you have to write your way to greatness, not think of the tool your way to greatness. So my focus has been to put in the reps, just be disciplined. I mean, I actually also don't even do the social Substack prompts all the time. Like every time I hit publish, there is a prompt that shows up saying, oh yes, include your— Oh yes. We create like, I think the tool auto-creates social media images for you if there's no image. Sometimes I don't even do that. Sometimes I don't even have an image, you know, I just like have stuff. Now I've been trying to get good at using DALL-E 2. Good. Create an image based on the prompt of the essay. And every time I'm surprised with the output because it's like, you know, AI is being creative. Yeah. The image for me. So yeah, Substack-wise, I'm not doing anything, you know, like extraordinary. Writing-wise though, I think I have some, I have some hacks I want to share, but like, do you want to, you want to lead this a little bit? Like, do you have any writing hacks that helped you as a writer yourself?

Or honestly, no, I have not. Not figured all that out. The one thing I'd say, just to tie back to having a second set of eyes look at it, or if somebody wants to share it with somebody else, I wanted to share how you actually do that on Substack without copying it into a Google Doc or something. Within the settings page, there's a section called Team. And if you add another— I'm sure that you've done this— if you add another person's email address there, it'll send them an email and they can accept. And then you as the writer can send them your draft and they can look at it, they can work on it, or They can just, you know, tell you, they can put notes. So I wanted to say that because, again, trying to save people a step of copying it and pasting it into an email and then copying it back. You can have collaborators and many of the top people on Substack, and you can set the person— do I want this person to be a contributor, administrator— to control what they can do and what they can see. So, so that's something. But when it comes to taking an outline and turning it into writing, I mean, I'm— believe me, like, for me, I'm banging my head against the wall just as much as you are trying to try to figure it out. And a lot of the times I just like draft and edit, draft and edit, draft and edit again for myself. And what works for you? Tell us about your process.

Yeah, sure. I just remembered something that you said earlier about the drafting. Actually, for folks who are listening, I will of course leave Linda's Twitter account in the show notes. I'll include that in the show notes. But one, if you're not following Linda, you should follow her because I love her tweets and threads about some of the FAQs on Substack, some of the obvious tips that are probably hidden in documentation on page 9, Or page 8 somewhere on substack.com. But it's just that what, what I love about what you've been doing, Linda, and I wanted to kind of call out publicly is it's one thing to know all of these things, you know, because you work at the company, but you constantly bring them up in your Twitter as well, which is very helpful to someone like me who I don't have the time to go to substack.com help docs all the time. Every time I see a tip from you, I'm like, whoa, that's useful. I bookmark it. The number of bookmarks I've done for the threads you've done. Oh, huge. Yeah,

that's awesome.

And I don't know if you're getting this sort of straight up feedback loop back to you, but that's why I wanted to say that. And it's very helpful. Right. And I used to do this even when I was at On Deck. Or whatever I do, the most obvious things that people— I expect people to get value from, even if they are obvious to me and my peers, because it may not be obvious to the customers because they might be busy. Now, even though it looks like you're repeating yourself, it's always a good thing. So back to writing tips. I mean, the biggest writing hack that I think that I had was publicly announcing that I'm writing on Substack.

Wow. I like that.

And that I will ship a newsletter. So I had to ask myself, what kind of promise do I want to make? Do I make an unrealistic, outrageous promise, or do I make a realistic So I made a realistic promise, which is I'm going to ship one newsletter edition every week, which is realistic. The real hack though is I said I'm going to ship it on every Wednesday because it was specific and because I sort of co-signed this in public. I'm the kind of person who hates disappointing people. So that really played into this really well. Yeah. Every Wednesday I would wake up and be like, okay, I promised these people that I got to ship something today. So I just kept at it. So there was no questions. Like if anybody tried to book me a meeting on Wednesday morning, I would politely reschedule because Wednesday morning I want to write. There's a lot that happened because I chose a particular day. So for my next newsletter that I'm doing right now, I chose Friday and I— that's the first thing I did was choose not even the custom domain, not even the pretty logo, choose the day I want to publish. I think that's a really big hack for people like me at least. The other thing that I learned is there's no holy grail when it comes to writing. There's no secret bullet. There's no silver bullet secret sauce. I was tired of asking Kay Hee. I was tired of asking David Perel. all these people, right? And Lenny, and like, what's your writing secret? What's your writing ritual? Everybody had their own answer. Yeah. Everybody had their own weird answer. It was like so different. So I thought, okay, maybe I should discover my own answer, you know, instead of trying to like look for the strategy. And so my strategy is that I usually write the outline, and I, in the outline, always have a question that I want to help answer. And questions are very good because usually it's an indicator of what people might be thinking, what might be— what they might be wondering. And also questions allow you to open and close curiosity gaps. So with the question, you can open a gap, and then with an answer, you can close the gap. So my outline usually is 4 or 5 bullet points, and it includes a question. And then there is a clear format that I follow every newsletter. There's like a section that would have shoutouts and sponsors. By the way, I've been getting sponsors too, which is crazy.

Excellent. Yeah,

but I just stick with it, you know. It's very simple, very basic. Folks who want to check it out, it's called— it's kp.substack.com. So it's very simple. I don't tinker too much. That's really my secret, is that I focus more on Reps, like putting in the reps and just really delivering value on each edition and not worrying too much about optimization.

This issue of reps, I remember Paul Millard, who was another Substack writer who's wonderful. He has a terrific Choosing Your Own Path, The Pathless Path. And he had a tweet that said, it really stuck with me, where he said, do something 100 times, then figure out what's next. And that is what you were executing. You were just saying, I'm just going to do it 100 times. I remember another person who came on Substack and he gave the feedback, I much prefer this to WordPress because when I was on WordPress, I kept tweaking and customizing and changed the color and tried a different font and tried something with the margins. And he wasn't writing. And what's going to actually help you? Yeah. You know, 9/10 or more of all of the reading and interacting that people do with Substack content is still in the email inbox, the good old-fashioned email inbox. So you can get very seduced by, well, what does my publication— publication pages are customizable to a degree on Substack, but it's not as customizable as a WordPress instance. But with WordPress, the problem was people would get sucked into things that did not actually move the needle for them in terms of becoming a stronger writer and creator and building an audience. Because the deductive— when you— I mean, it's the classic procrastinating. Oh, let me do my the ironing before I do the creative work that I need to do because it's intellectual heavy lifting. So I think this idea of reps is— and I also wrote down when you wrote about curiosity gap, there is another great person for people to follow on Twitter and on Substack is Nicholas Cole, who is a— Yeah. I'm sure you know that name. And he talks about, well, many things to do with writing, many things to do with creativity and business building. But I always loved— he has content about how do make a compelling subject line/headline. And he talks about establishing that curiosity gap. Like, you know, rather than saying, you know, this is how you perfect your golf swing and giving the answer in the headline, you say the one thing that helped me improve my golf swing. And some people say, oh, that's clickbait. And he says, it's not clickbait if you fulfill your promise. Again, that stuck with me. So all these issues of creating a curiosity gap, and then you're the one to relieve the curiosity. You don't have to be the world's greatest expert in this thing. You don't have to be a PhD, know-everything, deca-millionaire in the thing. You just have to be a few steps further than the person who's reading your stuff. Or you can even say, let's go hand in hand together and figure this out together. Right. So everything you're saying about reps, I think it's not just that it's good advice, it's that it's what I've heard from some of the top, top people on Substack who I think people who are starting would be surprised to know that somebody who's making more than $1 million a year of recurring revenue doing a paid newsletter still worries about, oh gosh, it's— I promised myself I'd get this out by midnight, it's 5 minutes to midnight and it's not done. Still worries about, oh, why did those 3 people unsubscribe? What did I do wrong? Still worries, oh, was that a weak subject line? Is that why I have lower opens? Like, yeah, all this stuff, it doesn't go away, but you can get more confidence as you go and say, it's part of the game. A lot of people liked it. A lot of people stayed signed up and I still got it out by midnight.

Right. And one last thing about sort of my last writing tip that just came to mind when I was— when you were saying your answer was this, I think was another game changer for me because every time I would write, I think I would just, you know, constantly go into loops and like basically dig my own rabbit holes and just go so deep into long, really long-ass paragraphs. paragraphs. The hack was basically I promised myself that I'm gonna read out loud. Mm-hmm. It sounds so stupid and like basic that everybody should be doing it, but actually, you know, there's a chance of, you know, intellectual procrastination, or like basically just like going through it like too much, you know, when you're not reading it out loud. So every time I finish a paragraph, I pause and I read the paragraph out loud, and I always think, is this something that I would say in a session or on stage or friends. If it doesn't, if it feels too much intellectual or too jargony, I cut it, I rewrite it because my focus is that I want to seem as authentic as I can be and as KP-like as I can be in my writing.

Yes.

So I want to write the phrases that I would say in real life. And that's been such a blessing because even the outline, sometimes I have the tendency to writing like a whole essay on each bullet point because, you know, we're all like, like to just keep going. And then I pause and I'm like, okay, this is going too far. You got to cut it down. So it also helped me with the length and the tone because I'm reading it out loud. So, I think those are, yeah, those are the 2 tips.

Yeah. Mark Twain quote, kill your darlings, meaning the sentences that you're the most in love with because they have the most elegant vocabulary test words, those are the ones that have got to go because you want it to be more conversational if you want it to be read. So, I, and I don't, that's such a good tip to say read it aloud. I do not do that enough with my writing. That's something that I'd like to do more because we all have to, even if it's not writing for a large audience, communicating at work, all these same principles still apply to all the communicating we do, and we don't want to be stilted and corporate and academic sounding.

The biggest mind shift that I had to make, though, Linda, was I thought I was not a long-form writer, even though I was one. Because at work, I was writing these long Slack messages, I was writing emails, like all of us are writing. Yeah. We think that we're not, you know, we're not a writer, right? We don't like official, like, you know, journalists, you know, like doc. But I feel like we're all writing if you work in anywhere, you know, as long as you're not doing a physical manual labor job, like you're— if you're a knowledge worker, you are writing, you know, pretty much. And so that really shifted my perspective. I realized that I was, I was anyway writing on private platforms or Slack or, you know, Twitter threads. I just didn't give them a home in an essay format. And finally I did. So yeah, yeah, those are the tips I have. Those are the, you know, prompts I had for today. Yeah. And really appreciate you being here. Really appreciate you sharing your wisdom and perspectives and insights. Thank you so much, Linda. Where can people follow you on the internet?

Thank you so much too, KP, and thank you for your kind words too. It's very encouraging to me to continue to share tips and try to help people. Where can people go on the internet? The first place people should go on the internet is substack.com and set up a Substack. Here's, here's what I'll leave people with. If you have heard this and you say, darn it, I'm going to go set up my own Substack now, tell Today I'm inspired. Go to substack.com/Linda, and it's going to give you the sign-up form. And all that's going to happen is I will get a message that you signed up at that URL, and then I can sign up for your Substack, and I'll know that you signed up from me being on this podcast. So if you forget, just go to substack.com and click the orange button that says start writing. But then the other thing people can do if they're interested to learn more and get whatever tips that I'm tweeting out and see Substacks that I'm retweeting and things like That is to go to Substack Linda on Twitter. And yeah, I always really enjoy to talk about the opportunity of Substack, but also just the more general opportunity that's opening up for people to have their creativity and reach an audience directly without the need to have an intermediary of a social media website or without the need to please a gatekeeper. You can just go directly to the audience, and that's what the internet should be all about. So I just really— it was great to be here. And yeah, I'm sure that I'm going to continue to talk to you as you continue to grow on Substack more and more, KP.

Thank you. So kind. Thank you. And like I said, you really inspired me to begin a new experiment now, which is the paid one. And I haven't done that so far. So I feel like we'll probably meet again in a year when I have a new experiment.

I'm sure of that. I'm sure of that.

Thank you so much, Linda.

Thank you too.

Have a good one.

You too. Bye.