Special Guest: Matthew Guay, Co-Founder of Reproof

The transcript below is unedited output from OpenAI Whisper.

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Hi, I’m Len Epp from Leanpub and in this episode of the Front Matter podcast, I’ll be interviewing Matthew Gay. Based in Bangkok, Matthew is a writer, entrepreneur, and founder of Reproof, a new collaborative writing app for publishing online. You can follow him on Twitter at maguay and check out his website at techinch.com and check out Reproof at reproof.app. In this interview, we’re going to talk about what Matthew has been up to since he first appeared on the podcast way back in 2017 and about his plans for Reproof. So thanks very much, Matthew, for being on the Front Matter podcast. Thank you for having me on. I usually like to start these interviews by asking people for their origin story, but as I mentioned, you’ve already been on the podcast in the past, so I’ll just add a link to that episode in the transcription so people can read about that. But for the sake of this conversation, I was wondering if you could talk about where you were when you last appeared in 2017 and what you’ve been up to since then. Let’s see, 2017 would have been Zapier still, I believe. At that time, I was Zapier’s senior writer and editor, and a big part of our focus was writing a series that we turned into books, which I think is what we would have talked about at that time. A big part of that strategy was we would publish blog posts about a topic over a month or two, so say about Google Sheets and get started out with one about just getting started with spreadsheets and one about why you’d pick Google Sheets and one about Google Sheets add-ons and so on. And then we rolled those together into an e-book that we built with Lean Pub and published on Lean Pub. Also took that to the Kindle store, the iBook store, and used that as a bit of a lead gen to turn a set of online content into a lead magnet, but then also it’s like the sum is greater than the parts, and once you had that whole thing together, it was something that people could pass around their team, help out people with learning more about that topic than one blog post could do on its own. Which worked really well. I really enjoyed doing that. And we did a number of books with Zapier doing that towards, wow, what if it had been 2019? I’m blanking on my own resume here. I jumped ship from Zapier and started a new venture. So that was, I don’t know, if you want me to go ahead and jump into that. Yeah, definitely. Definitely. That was Capiche, I think. Is that what that was? Yeah, that was Capiche. Yeah. Yeah. Founder approached me with this idea, was like, hey, would you be interested in helping build, the idea was LinkedIn, I’m sorry, not LinkedIn, Stack Overflow for business software. And so it was basically like, what if you’re a spreadsheet expert and you could come in here and answer questions about spreadsheets, but you have questions about Figma and you could ask those here and someone that’s good at Figma could come answer those and you could sort of unlock all this knowledge that people had around software. And so we promoted that the best way I knew how, which was SEO focused long form content. And the first thing we did with it was, after a bunch of brainstorming, we had this idea. People are intensely curious about software pricing, whether just from an internal curiosity perspective or from trying to find the best deal. And so we built this initial signup thing that we said, hey, if you’re wanting to find out what other people pay for software, we’ve built this database and we’re going to let people in, but you need to share three products you paid for before and how much you pay for those to get in. And then in a month we’re going to open beta access. And so we had a core set of data based on publicly available pricing, based on friends and contacts we had that were sharing their own pricing. But then a big chunk of that came from the initial onboarding sequence of people asking them to share their pricing when they came in. And so then you end up finding out, like, oh, Slack has more plans than you would find out publicly. Or like there was a legal firm, I believe, that had mentioned they spent quite a bit more for Slack, but they had a higher security plan, they had more detailed backups, et cetera. And so you’re able to get this detailed info about pricing. And that sort of jumpstarted the community. People come in now to find out, oh, I’m planning to use HubSpot, but I can’t figure out what it’s going to cost. Let me see what other people are paying for it. And then when they’re getting set up with HubSpot, then they go, oh, well, like, how are other people sending invoices from HubSpot? And they go ask that in the community. And it got a bunch of back and forth and really worked really well. I think the interesting thing I found with it, just for a quick takeaway, was people are, you end up splitting based on what types of software people are going to ask questions about. So if you’re a founder or someone in the leadership position in a company, you’re going to have more questions about, should our company say, use HubSpot versus Salesforce? But if you’re the normal person in a company, it was just dictated from on high. So you don’t have questions about, should we use it or not? It’s more like, I’ve got to use this thing, how do I figure out this problem, right? But then say, you probably have freedom to choose your own writing app, email app, maybe even a personal to-do list, if not your team to-do list, notes apps also. And so your normal people were very excited to discuss those things. And so notes apps, for example, that was right in the middle of when Notion, Roam Research, Obsidian were all blowing up. And so those were things people really just debated about, like, mine’s better than yours, that kind of stuff. But for HubSpot or something that’s more on the corporate side, or Stripe, or these big decisions, those were more things that people just had questions about, like, how are you using it for whatever, because I have to use it in my company. And so it’s interesting, you can sort of split the market like that and see focused questions based on the audience, just based on the software they talked about. Because if you’d asked why to use Stripe, we had this sort of info that you might be a decision maker in a company, for example. So anyhow, it ended up being a really interesting project, fun to work on, did a bunch of writing with Adobe notebooks, and ended up that got sold to Vendor in 2021, I think, for $1.1 million. Yeah, just before we go on about that, actually, so thanks for sharing all that. That was so great. And so sort of succinct and interesting. One of the things I wanted to sort of touch on there is that in a sort of former incarnation of my own professional career, I was doing some work for a client once that involved basically being on the software, like the enterprise software vendor side. So I’ve actually had those conversations with people who are like, you know, I just spent all this time onboarding my team onto the last tool that they forced us to use. And now you’re trying to get me to switch to a new one. And it’s it’s so interesting because it’s so it’s basically it’s one one of the reasons what’s called enterprise sales, which is basically for anyone listening, you know, who’s unaware of it. Basically, you’ve got an app, let’s say you want to sell a license for like, you know, 1000 people to use it in a company or more or less. But you’ve got to get some decision maker to decide to do it. And probably there’s some other tool that they’re already using that somebody banked at least their last promotion on sort of successfully integrating into that company. So you’re coming in so that there’s there’s this personal element of it from the person who made the previous decision, or whoever’s now advocating for this thing, are they saying that person was wrong? That’s a really important dynamic, the teams that are going to be using it, as you say, whatever job they’re doing, they probably feel like they’re doing it okay already. So being able to sell in something new is really difficult. But of course, things do change decisions are made new executives come in, you know, they might, they might cancel that 350 million dollar investment in an entire TV network, you know, because they want to show who’s boss. And sometimes the apps that teams are using at that treatment as well. And so then you’ve got these teams of people probably with maybe project leads and stuff like that who are like, okay, so we’ve got to learn we really do have to learn this new tool. How are we going to do it? And this is just a big, just a big then now it’s just a big sort of problem on its own for like, how do we get back up to speed and even using this tool to, you know, be better than we were before. And so you’re saying that Capiche was partly trying to build a sort of way of solving that really deep problem. Yeah, yeah, to a degree, which, frankly, I didn’t have the enterprise experience enough to realize that was such a dynamic, I, I, I’d hit it, but I thought it was problems of I don’t know, stubbornness and a team type thing. And then you realize, oh, no, this is this is a thing across the industry. For example, on a very light level, the first blogs I worked for, we had a very old WordPress install that you never could get updated because IT was like, oh, we have these plugins that we’d have to rewrite if we updated. So therefore, blah, blah, blah. And it was terrible. It would lose your changes and it just was impossibly bad to work with enough that I mentally blame WordPress, but it really wasn’t WordPress’s problem. It was our maintenance problem. But but it’s that same problem, right? It’s like they pick this and they, they invested whatever and getting this custom theme and templates and whatnot. And then it was like, we don’t want that to go to waste. And so we’re just going to stick with it till kingdom come. And I feel like that’s something I noticed from a Capisce over time was that was the dynamic people were having across the industry. And at least you could help them a little bit by one, they’re finding their colleagues at other companies that are like, oh man, I have the same thing, but here’s how we worked around it. And that took a bit of that load off. And then number two, I feel like almost as an outlet for a bit of independence in your work that people do want to choose their own tools to a certain degree. And that that’s where I think some of the enthusiasm around say notes tools comes from is that people can actually go build some solution they want in notion and have a bit of that freedom, even if they have to use Salesforce, but they can pick something over here. And that’s a bit of the escape valve to a certain degree. It’s really interesting. Another sort of a feature of this whole experience. Would it be, you know, it was a startup, right, Capisce. And it started in 2019 and I got there, I got there sold in 2021, but something important intervened on all of our lives during that time. And so I imagined like, you know, so you’re in Bangkok, as I mentioned in the introduction, I am just imagining your team was probably like all teams, you know, distributed all around the world. Maybe with some, you know, clusters here and there, how did, how did you all kind of handle the pandemic? Right. So, so we were remote already. And so that was a saving factor to a certain degree, had friends and colleagues and other companies that were, you know, having to quickly learn how to work remotely and, you know, calling up and being like, Hey, how do you do all this? Because you’ve been working remotely all these years. And for me, it was just, you keep going, but there was something different with it, right? When you’re always home, I’d always had this escape valve of weekends, right? It’s like, okay, maybe I’m always in my home office during the week, but you’re going to go out and do stuff during the weekend, kind of see people, otherwise you’re going to start going crazy after a while, just from not having any interaction. And so, you know, I did a bit of the things everyone was doing during the pandemic. We tried doing Catan board game nights with friends over zoom, which is pretty terrible, honestly. But you watch Tiger King, which was honestly pretty terrible and, you know, all the other pandemic activities. But as far as the business, at first it was that, I think to a certain degree, notes during that time were a bit of a distraction. That was, you know, spring 2020 when there was a whole bunch of this discussion around like, no, Notion is better, no, Rum Research is better. And I do think there was a bit of like, people were obsessing over tools or having more time to dig into stuff just because of that. From a team structure wise, it was funny. I was in San Francisco in January, 2020, for a company meeting retreat, just three people. So it’s hard to say retreat, but we had a bit of that dynamic, right? We went out and did some fun activities and such. Anyhow, but it was, you know, you’re getting this news out of China. It was like, stuff’s going on. I went to Walgreens and was, would you believe Purell hand gel was on sale? Like they had a clearance on it, trying to clear it out. And so knowing I was coming back here and my wife was like, you should probably just buy something like that. It’s probably going to be something everyone needs. So I brought back just tons of little Purell bottles, but masks were already sold out in January. And then, you know, I asked at Walgreens, they’re like, Oh, tourists keep buying them up. I don’t know what’s going on. And the airport at the time, just as a funny mental thing, they had a sign up about Ebola. And I believe, what is it? The foot, hand, mouth disease or something that the CDC always has signs up to the airport about like, don’t bring back farm products, but nothing about COVID. And then on my return flight, I got to the airport and they were like, we rerouted your flight. You’re now flying through Beijing. And I forget if we had quarantines yet, or it seems like there weren’t quarantines yet, but maybe there was, if you came from China or at least there was talk of such things. And so I was like, you know, I’ll just wait as long as I need to for whatever flight that was, I was supposed to go through Tokyo. And I was like, just so I don’t go through Beijing, because that was like, if anyone was going to start quarantining people, it’s like flights going through Beijing are going to be the first. So yeah, that was crazy. And it changed business stuff a little bit too. So I think at Capiche, we had this idea early on that it was just going to take time for it to slowly build and you get this audience. And then we’d figure out the business model along the way, which is quite common for startups, especially in the sort of social space of sorts, right? Like at a minimum, you could sell sponsorships if you have a big enough audience and stuff. And so around July, we started bringing this idea around online conferences. What if we just put up an online conference? Like it seemed like something people might enjoy, that was July 2020, right? So you’re still sort of locked down. And one thing led to another and our founder got this idea of doing a live streamed audio, but using phone calls. What is like an MVP of like live streamed audio? And so we did what we called Capiche.fm, which was Twilio powered. It was a bunch of APIs tied together that basically you can have a call in show. And so you could, you know, you have your show start and you tell people this, they could call into the number, I believe, if I’m remembering the mechanics correctly, it’s been a bit now. And you could do a live stream group podcast like that, where just everyone gets called in, they could press the button and start talking. And you can record a live thing. And we sort of over time moved that to the browser and then ended up being a live podcast that everyone could listen to live. And you could sort of raise your hand and ask to participate. And then that ended up turning into Bracket, which was the last project I worked on there, which was short form audio. Because Capiche.fm had the idea of snippets or clips, I believe we call it, that you could cut out a section of your audio and tweet that to say like, this was the moment, got to catch this. And those were more popular than the full recordings, because you get people just talking live and rambling, it goes on forever. But those focus bits, that’s where the actual wisdom hopefully comes from. And so Bracket was built around that idea of like, what if you had a timer and you said, you can record for nine minutes and no more. And sort of that, having that forcing function to make you focus and make you really shorten what you’re talking about into one interesting thing. Ted talks of audio, sort of that kind of idea. And that was through most of last year that I worked on that, which was super interesting. I think the most fun, I got Andrew Warner to come on. And he really took on the idea in a negative sense of like, why is this, why are we going in this direction, whatever. And I guess I felt proud, I felt like I held my own, it was like, okay, I kept my head above water in the conversation. And that was fun. But then I ended up jumping ship and starting my own thing. So that’s where I’m at right now. Yeah, let’s, might as we talk, thanks a lot for sharing all that. That’s really interesting details, especially the sort of like flight being diverted to Beijing and having to make decisions about that. And for people listening who might be a bit surprised that like things were happening already in San Francisco in January, in 2020, you know, the West, the sort of West Coast tech culture did maybe partly because, you know, in, in, at least in North American terms closer to China, right. But like, you know, there’s that, there’s that ordinary reason, but then there is the kind of like very online kind of thing. And you know, people, people were, I mean, even here where I live in, in, in Victoria and British Columbia, like it, people in the tech sector here started preparing, I guess, a little bit, a little bit sooner than everybody else did. And you know, I’ve, I’ve had, you know, I’ve had these sort of like lots of kind of conversations on the podcast ever since then, where we, we actually introduced kind of a new segment where it’s like, how was the pandemic affecting you? And it was like, it was like, you know, I, I had it, you know, it hasn’t affected me at all. You know, I’m, I’m calling you from my basement because I’m not allowed upstairs. Cause I got back, I just got back from, you know, someplace, all kinds of stories like that. And it’s, it is, it is great to hear. I mean, you know, like, I think it’s a little bit cathartic for all of us to hear about those conversations that we had about Purell and toilet paper or whatever it was and it was all, it was all real. My, my barber, she, she actually was in, in Thailand when it really got going and a long plan trip in advance. And when she came back, she actually had no toilet paper. She couldn’t find any. Yeah. And it was just like, you know, no fun. Anyway, that, that actually, it’s sort of easy to laugh about some of those things now, but it’s, it is, I think, important to think about how like kind of funny it was at the time. Yeah. Like it’s sort of funny in the sense of kind of like, you know, just sort of unusual and we were all trying to figure out, are we overreacting to this? Are we not reacting strongly enough, which, you know, persists as an issue in some areas to this day. But was it, I’ve got a question about, so you went from Capiche to racket. Was it the same team? Yeah. Yeah, it was. Yeah. So it was a, it was a full on pivot. It was like, okay, let’s try taking on this different idea. And we sort of kept Capiche running in the background at the same time while trying to pursue this new audio idea. You know, it’s your classic startup thing of like, you throw a bunch of stuff and see what sticks, but in an entirely different direction. And I do wonder, right, in the non pandemic world, where Capiche would have gone in the meantime, right? I do think there could have been, it’s not that the pandemic required us to pivot there. There was no, nothing forcing function away from that or whatever. But it did sort of, I think, put a bit of angst or like, you’re itching to try something new or you’re like, oh, maybe we should something. And there were, there was some, I feel like just a question mark in the air, right? Of like, what are we doing? Is there a different thing we’re supposed to be working on kind of feeling, right? And in a weird way, I almost feel like that’s held over to a degree for me. Maybe it’s a bit of a midlife thing at 33, but it’s like the pandemic made me think you’ve got just this amount of time. And it just in silly things, right? Like, oh, I want to go on vacation to Japan. Well, now you literally cannot do that for a bit, right? Like that’s not possibility. And I guess where that never felt like something that could happen for now, it feels like a thing of maybe that can happen again. Maybe we, you know, we go back to not whatever. And so it makes you feel a little bit more like, huh, I’ve got this idea. Maybe I should just run with it because we’ve only got sort of a limited slot of time on this planet. And it’s obviously not some new idea, but somehow I feel like the pandemic crystallized that mentally for me. And maybe made me a little bit more or worse taking there of being like, well, sure, let’s just try it. Let’s go for it. I don’t know if that’s good or not though. Yeah, I think, I think people definitely, definitely trying new things in all kinds of different areas of life was definitely a part of it. Recognizing that how good or how bad your life was otherwise was, I think, a lot of people had one, one, I haven’t talked about it for a long time, but one curious phenomenon that happened here was couples walking down the streets, holding hands when they, that was not a common sight beforehand. Unfortunately that sort of pleasant thing went away, but I think there are, you know, but there are a lot of people who started, you know, they were just thinking about things like that. And you know, especially if there’s like maybe a family member, you’re not going to be able to see for who knows how long, you know, that’s changed the way you think about things and professionally as well. So yeah. So let’s talk about, let’s move on to talk about your latest project that you moved on to. So yeah. Can you talk about, talk a little bit about that? Sure. Yeah. So this has been an idea that I’ve been building for a while is that I didn’t feel like there was a writing app that slotted in to the modern publishing process well. And with that, what I’m meaning there is for publishing on blogs, on email newsletters for taking an idea and just distributing it out there. So on the Zapier team, so Zapier for anyone who hasn’t used it is an automation tool that basically say you have a new cell coming on Shopify. They can take that data and automatically say, copy it to Google sheets to store it for you or make a label and print it out with a Google cloud print though that actually I don’t believe still works, but things like that, right? You could set a whole set of automations and when that happens in one app, it does a cascade of events elsewhere. And so here in the marketing team, we were teaching people how to do that, how to automate their work. And we were having to write and copy and paste between apps to just get our stuff published. Our standard workflow would have been writers tend to like to write in whatever apps they like. So they would write in some focused writing app, perhaps finish there, copy it, paste it into Google docs, share that with the team and say Slack. You would get feedback from your editor, from colleagues on the team, suggested changes and comments, right? You’re going to add all of those, hope you didn’t mess up the formatting too bad, copy it from there, paste it into the CMS and then publish or hopefully publish this draft, make sure it looks good, then actually schedule and publish. And then if you’re working in a workflow where you want to publish an email newsletter that has that full blog post, you’re going to then go over to your Melchimp or Substack or what have you and publish that. So again, copying and pasting. You’re going to perhaps make a shortened version of that that you’re going to post on LinkedIn. Perhaps you’re going to post that again on something like Medium. Publishing is crazy now, right? It’s going everywhere and there wasn’t a great way to automate it. Even used to there were tools, even Microsoft had one, Windows Live Writer, that was designed for blogging. Basically it was like you write something and you publish it and it goes to WordPress. And there were still writing tools to do that from an individual perspective, but not from a team perspective, not in something that you could tie into an editorial workflow like that where you’re like, okay, let’s go from A to team to feedback to publish. And so that was a bug in my head, I guess, for a few years of like, hmm, there’s something here I feel like like a sort of API driven writing workflow would be useful, right? And then I had this other concept is when I’m writing, and I would say maybe just me, but I’ve talked to a number of other writers and friends in the industry and other people who have the same problem and said similar things. Hopefully I just don’t have a group of people who all have this problem and no one else, right? But here’s the idea is when I’m writing an intro or a title especially, but often other sections of an article, I tend to rewrite that same section several times to try to see what sounds good, what fits. Maybe when you start writing a paragraph or an intro section of a chapter, you sort of ramble a bit, right? There’s this idea of what’s his name? Hold on. Hold on. John McPhee, I believe, draft number four. I believe he’s the one who shared the idea originally, but it’s like if you’re stuck when you’re trying to write, then write a letter to your mom and you say, dear mom, I was walking along and I saw a bear and blah, blah, blah, blah, and you keep going and you start telling this story. Then when you’re done, you go back and you delete that first paragraph and the dear mom and you have your story. It’s like you have to have something to focus your attention to get that, to get going, right? You have to sort of jumpstart yourself. And so to do that, I find myself writing multiple intros, multiple titles. Maybe this one sounds good, but the team is like, no one else is going to click on that. You should change it to this, right? So what I would do is I would write all these titles and I would share them in Slack and ask the team to vote on them. Does this one sound better or that one? In my Google Doc there would have had multiple intro paragraphs maybe or maybe separate pull quotes. It’s like, could we use this one here or maybe we should use this one instead. But then the document looks quite messy, right? Because you’ve got, it’s like, hey, these, don’t read this in order. It’s like this and then jump down to here, right, because you’ve got these sections that are repetitive, right? Three intros. Okay. Now keep reading. So the idea came from children’s flip books. We’ve seen those flip books that kids have to have like a head of a dinosaur and a body of an elephant and the tail of a donkey or what have you. And they can flip them around and make a weird monster. It’s like, well, what if you could do that for writing? A digital paper, there’s no real reason that it has to be top to bottom, one continuous line of text. We could have more space here. And so what we’re building is this idea that you have paragraph versions in your document and that you write a doc, write a paragraph like normal, then you’ve got a button off the side. You can add a new version of that. Your existing writing slides off and you write a new paragraph there. And so then you can keep doing that and you sort of end up, if you can zoom out and imagine the whole document now, your title is like this really wide thing and your rest of your text is down here and almost like a sideways slot machine, right? But your titles can swap in and out. And so then you could, on the tablet version, swipe or on a computer, use your arrows or the mouse to click back and forth and swap in those paragraph versions to read them in context. So you start out, you start out once upon a time in a land far away, maybe not. And so you click the new paragraph button and you go, it was a dark and stormy night and you keep going, that’s not quite it. So you hit the paragraph button again and then you’re like, it started like this one day and you keep going and you keep writing like that. You add your next paragraph and you stay in the flow, right? You stay in that one document. But then every time that you sort of doubt yourself, you want to try again, you can add a paragraph version. Your old stuff scoots over to the left of that one paragraph. Everything else stays the same and you get a new paragraph that you can try again. And so the idea is there, you’ve got a tool that helps you experiment with what sounds best for your writing, that you can find the best way toward your ideas with those paragraph versions. And if you sort of combine that ideally in a collaborative way with an easy way to publish, that we feel like that’s the core idea of what could be something that will help teams write and publish better in today’s sort of web focused publishing workflows. Thanks for that really great description. That’s a really, really interesting idea. I had all sorts of things going through my head when you were explaining that, including one of, you know, I’ve always been said, you know, like the, the introduction, particularly thinking about essays, the introduction to an essay is both the first and the last thing that you write because you don’t, you, you, you probably have some kind of plan. So you write to the plan and then the plan changes along the way. And so then you rewrite it as though you knew all along what you were going to be doing, which is, you know, how you, how you write a good essay introduction. Right, right, but that, that idea of I was specifically when you’re talking about the kind of like rows of kind of paragraphs got me thinking of something that at least I think I’ve seen this practice in design, like, you know, you know, something like sketch or something that has an infinite canvas, people would put, you know, various iterations of the same proposal for like that part of the, that banner on the webpage or whatever. And often they’re in a row and you say, you know, and you can even, you can even imagine a kind of, I’ve never used it, but like Tinder style, like kind of swiping kind of, because we make it very kind of like your hands are not typing, you know, you’re, you’re thinking about the writing and I mean, there’s all sorts of super interesting stuff that could happen there. Like around like presenting, presenting people with a set of, of rows, asking them to pick, just pick the ones you want and then testing, testing how that comes out in, in production as it were. Right. So you could AB test results of things like that. It’s also, it’s also like, and it’s sorry to go on, but like, it’s just as a pedagogical tool, it would be super interesting. For example, if you were teaching a writing class as a professor and what you could have a set of these rows and say, okay, everybody pick, pick yours. And then let’s, let’s all justify why we did it. Like here I am, I’m the teacher, so presumably I know something you don’t. Here’s why I, you can watch me make my decisions. Just like watching someone who’s better than you at polytopia choose a different order for their games, their strategy. Right. Right. Yeah. So there’s like, that’s a super interesting and I think very kind of like visually people would get it right away. Right. Like, you know, like, so yeah, good, good luck with that. That’s really, really an amazing idea. And like a sort of one, I certainly haven’t heard before of like, I’m sure people have done this in different ways, but having a product designed to do that, I think would be something totally new. On that note, with respect to, so you’ve, you’ve worked, you worked at Zapier, you worked, you did Capisce, you did Racket, you’re doing ReProof now. And a big part of your job has been getting attention for stuff. So before, before, before I let you go, I actually wanted to take the opportunity because so many of our people on our, who listen to our podcast are either, you know, publishing industry people themselves or self-published authors for whom, and a lot of them are entrepreneurial. So they might like have, you know, not only every book is a startup, but you know, every startup is a startup and sort of, you know, how do you get attention? And it’s, it’s very interesting because, you know, five years is a long time, maybe or maybe not. I actually don’t know in kind of the SEO world. So given that I’m just picking five years, cause it’s been five years since you were on the podcast, but like, have you seen, what are the, what are the biggest changes you’ve seen either in available options for sort of getting attention generally online, of course, or, yeah, new, new sort of conventions within the, for experts in that world? Right. The thing that’s always held true, right, is that audience is what matters the most. And as soon as you can start building your own audience that you can redirect into what you’re working on is, is so crucial. And the thing I feel like I wish I had started earlier with is the, is after we had this massive audience of existing users from the content we’d already created. And it’s, it’s just this big effect, right? Of like a snowball going down a hill that you build momentum as you’re going down. And then from an SEO perspective, each new piece you post then has that momentum of everything else behind it. And so your chance of shooting to the top of Google was so much higher just because it’s like that snowball effect, right? And so when you’re starting out new, I mean, especially today, content marketing, say five years ago, but especially say 10 years ago, when I would have probably first started as Appier was an industry, but it wasn’t such a focus. It wasn’t the thing that every new startup was dumping resources into. And today you’re competing against literally everyone is trying on this, right? Like it’s just incredible how much good content is published out there today that you’re competing against. Rising to the top is much harder. I feel like you have to try harder to stand out. You but the basics still are the same. High quality content is still slightly scarce. GPT-3 and such are making it easier for people to write, but they’re not making it easier for people to have unique stuff. And so if you can go out there and do unique research and have a unique take on something, there’s still a spot, but you have to try harder to get attention. A trick I’ve used a number of times that’s very hit and miss is trying to get to the top of communities. So if you can write stuff that will rank well on say Reddit or Hacker News or some other focused community for your audience, that’s going to probably have the best conversion rate. That’s going to do better than, and it’s something you can, you can try for better than just trying to say, get to the top of Google when you’re starting out new. Social networks have become incredibly hard to actually rank on. Like used to it was, I feel much easier to just put something out there and at least get some traction with it. And now if it’s not the right time, the right people see it and retweet it quickly, or you don’t promote it, it’s just going to fall down the feed. Like it’s really surprising now to actually tweet stuff and it’s just entirely silent. Then you tweet the same thing at a different time of day and it’s okay, right? Because it just, it’s, it’s really hard to grab that kind of dynamic right now. And I hear this from friends that work more directly with social media. I have a friend who’s, his main job was publishing on Facebook stuff and doing instant articles and such, and used to, apparently it was much easier to get traction there. And now it’s much harder. It’s like, if you’re not going to pay to play there, it’s not going to work that well. And so weirdly you’ve ended up in this back to basics thing of your own website is always the most valuable. Your own audience is always the most valuable. So existing customers, whether they’re in a platform or on your own website, there’s always a huge value there of having like, this is my place and no one’s going to take it. And then SEO is not going to be a free thing. It’s not going to just come automatically, but you have a better chance of carving out a niche and digging a bit deeper. So maybe look for Google keywords that are less commonly used. So if you’re writing, and this is weird, this is like the first thing I ever did for SEO, but I feel like the lesson still applies is if you’re writing how to connect your printer to a computer, good luck. You’re never going to show up on the first page. That would be silly. But if you’re writing how to get a specific model of an HP printer to connect to a specific version of windows or Mac OS, right? If you had some problem there, and this is a problem probably other people will have, and you’ve figured out how to do it, you’ve got a chance at the first page, even if you’re a new blogger, just because you answered a question that no one else had. And if you can find those things for your industry, that’s still where the value is. Yeah. Thanks very much for that. That’s so interesting to go back to basics. I mean, when you, when, you know, when the competition sort of people kind of, as it were kind of commoditize the tactics and then you go back to basics, make good content, you know, have a, have an audience already. But it’s, it’s funny you mentioned that because not too long ago I interviewed someone who’s in something called the developer relations for a company in Europe and named Sarah Lean. And she, she publishes on a YouTube channel under techie lass. And she said the exact same thing, like she had pretty good success with her YouTube channel and growing it. And it’s like the most, the most show people how to do something and show how to people how to do something very specific. Um, it reminds me that like one of the most popular posts we’ve had on lean pub on medium was a post I wrote after getting really mad at a dumb problem, which was how do you get an E pub file where more than 50 megabytes in size onto Kindle, the Kindle app on your iPhone. Oh yeah. Yeah. And like, that’s a very specific problem. Right? Like, and I found, I found like I found a solution which was basically like put it in, get sign up for some of the file sharing service, like Dropbox, get the app on your phone, on your computer. You can put the file on there, then you can open it on your phone, but that’s where it gets tricky because the UI and stuff like that. Right. But I figured out a way to sort of chain a bunch of things to kind of finally get that book on there that probably outdated now. But, but, but anyway, no, it’s, it’s, it’s so interesting that you say that. And the thing that I like, I actually quite like about the fact that that’s true is that when you’re doing something that you’re providing people with something of real value, um, yeah. Yeah. Uh, and, and so you can, if you’re, if you’re like, cause I think often when, especially again, speaking to sort of like the self publishing or kind of startup type people, often people like feel like SEO, their encounters with it is probably be really gross people like will you cross link to my website, you know, like there’s actually like the good kind of SEO is actually like genuinely providing people with things that you are interested in, that you have figured out that they, they would get value from knowing, um, this, this is like a huge, a huge thing in it. And by the way, like you’re like, I would just mention that like your blog might be about all kinds of other stuff, like let’s say lean pubs, you know, but then, but here’s a, here’s a handy trick, you know, um, uh, one, one specific thing I actually wanted to ask you about. So you brought up hacker news, um, and, and communities and stuff like that, right. And often I think one of the struggles people face, this is a bit different if you’re just an independent author, because then it’s kind of like, here’s my, here’s my new book I published, you know, um, that that’s okay to do on most communities, but if you’re working for a company, you’re not really allowed to directly promote your company, your company’s stuff. So someone’s I’m sort of just very, I’ve actually, I’ve always, I’ve always, I didn’t, I didn’t plan this in advance, but I’ve always wanted to ask someone who might know the answer. Like if you’re a company trying to get like a small startup, trying to get some big, some attention on specifically hacker news, how would you do that? Yeah, do you have any thoughts? You have to keep that audience in mind and provide value for them specifically, right? So it’s the same thing you said from an SEO perspective of, um, so say Zapier, our mantra was always, we were going to answer people’s questions in the best way possible. And then if Zapier was a solution there, we can offer that as an alternative. So just as easy on the SEO side example, uh, like, like if you had some specific problem with, uh, or you’re just trying to get your Shopify contacts into Google sheets, right? We could write that tutorial. The catch is, and the thing I think people often get wrong with that is actually tell them how to do it manually with those tools that they Googled, right? Don’t jump into your product directly, um, because otherwise they’re going to bounce, right? But if you show them exactly how to do it, then you’re like, but we also have this easier way that can work well too. You can automate it with Zapier and you teach them a bit of that, um, the people who just wanted the solution, they’re going to go through and be like, Oh, this is cool. And uh, they’re done and they bounce and the people who want something better, they might sign up and those convert while those do really well from, I feel like, um, make friends perspective of people think of you as a nice company of like, Hey, they helped me out when I was using their thing. And then also you can bring in customers for that. So say for hacker news, a similar thing, it’s keep in mind the audience, um, right. Stuff that’s attuned to what they’re looking for. Um, and then if through that you can promote your product, then good. But I would see it as a longer funnel, right? It’s like, say you’re writing a example with Capis that worked well, uh, we wrote, I wrote a detailed history of Markdown, Phil’s role for lean pub as well. Um, and I went back and found some early instances of it. Um, it was used in the peanuts, comments strips of all weird things like they would put asterisks around the word cough. Um, it was sort of like, this isn’t a real word. It’s like a sound effect. So maybe it’s italics of sorts. Um, and there are some slight connections between that and email formatting and then John Gruber’s Markdown. So we leave that to a story. Hackernoo’s loved it. It was the kind of thing that sort of scratches intellectual curiosity, as they would say, um, wasn’t directly about Capis, but it did bring people into our site. And then when they were there, maybe they commented and if they commented, they signed up for the site. Maybe they clicked around to other pieces. Maybe they clicked the link in the article that linked to other things we’d written about. Um, and you ended up, say you bring in 10,000 people and maybe you convert 200 of those to signing up. But those are people who were interested enough to have read your piece and gone all the way through it and still clicked around and been like, Hey, what is this place? This is pretty cool. And then signed up. And so you’ve got this real high intent there versus if you try to rank for like, hi, H&N, we launched a new product. Maybe if you’re NYC, it’ll work, but probably not otherwise. Right? So it’s like, you have to redirect. Reddit, same thing, depending on your subreddit, um, you’re going to get banned for spamming pretty easily. And that’s a good thing. That has helped a lot of subreddits stay really interesting. But it does mean if you go in there and you answer other people’s questions, answer the whole way there. And then you’re like, I also read a more detailed tutorial here. If you have, if you want to check it out, that’s probably going to get by right. And those kinds of things, you can sort of a way to join the conversation again, for me, it’s, I guess, from a how to do stuff kind of perspective is from a product marketing background, um, that I’m coming in more from, uh, but from promoting a book, I could imagine a similar dynamic working, especially if you have sample chapters online that you can link to perhaps, uh, uh, you know, some books now are, have the full contents available online, but they’re not fully like, you’re not promoting that it’s all the way online. It’s like, it’s there from an SEO perspective and maybe you can link to those chapters and people end up buying it at the end of the page. Um, but again, it’s, it’s about that providing value and selling like, um, in that community, they need to feel like you’re not trying to sell something, they need to feel like they actually got more value probably than you’re getting from having taken the time to call it there. Yeah. And it’s interesting. I’m glad you brought up that very, uh, battle hardened detail there, because when you’re in the middle of these, these how to explainers kind of thing, you can be like, wow, I am, I am putting, I am probably putting more work into this than we might sort of get like directly assessable value back. But at the end of the day to compete, to have really great content rather than tricks and time wasters, it’s, it’s probably the right thing to do, um, especially if it’s most compatible with your personality. Um, just before I let you go, I wanted to actually sort of pick up on one thing that you mentioned there about the, uh, peanuts comic strip using sort of asterisks to surround a word to sort of convey some kind of meaning about the word. Um, and I, and just to tie that into sort of like, you know, why is it 2022 and we still need people like, like Matthew to be out there making writing apps and stuff like that. These are really hard problems. Um, and so, and one of the hardest things is to get people to, is to explain to people like where these conventions come from. Um, so for example, and like basically what’s, it’s an old timey word term now, but desktop publishing and having what you see is what you get programs that you wrote your manuscripts in really turned into a big kind of problem in the publishing world, right? Because prior to that, the idea that like, probably there’s one out there. If there is, please reach out to me and let me know. Cause I’d love to know about it, but I doubt there’s a typewriter out there that has both ordinary letters and a parallel set of italics letters. Right? Oh wow. Yeah. Because why would you do that? Right. And the reason actually, the reason typewriters had an underline was to indicate to a book maker or, or whoever that this manuscript, this line in the manuscript, this word should be in italics. Um, uh, so you had to, because you were writing in plain, uh, writing in a typewriter is writing in plain text, right? Like Absolutely. And uh, and if you want to indicate formatting, you have to type the formatting instructions in there and what could be easier than surrounding a string of characters with the same character to indicate everything in between these two things is now go to your whatever kind of, you know, uh, code breaking sheet you have to know what that symbol means in this sort of system. But then there’s all these different systems and stuff like that. And, and anyway, that’s just a sort of really cool example of how things that seem kind of arcane were actually kind of like, like, kind of like weird, like to people who are used to writing in the desktop publishing world, why can’t I just hit command B when I’m writing in plain text? Why do I have to surround it with like two asterisks on both sides or whatever? And like, well, this is why. And actually if you’re writing in plain text, your manuscript will actually be kind of readable forever. Whereas if you’re writing it in a proprietary kind of binary, as it called format, um, you know, it can be lost. But that’s, that’s some sort of deep stuff. But anyway, I definitely liked that. So interesting to hear about that history of Markdown article. Um, and we’ll make sure to link to it in the transcription, but, uh, well, Matt, thank you very much for, uh, uh, being on the podcast for a second time after all this time, I’m so interesting to hear about all the cool things you’ve been up to and, uh, best of luck with reproof. Thank you so much for having me on, it’s been very chatting. Thanks. And as always, thanks to all of you for listening to this episode of the front matter podcast. If you like what you heard, please rate and review it wherever you found it. And if you’d like to be a lean pub author, please check out our website at leanpub.com. Thanks.