How RemoteBase Grew from 112 Subs to a 6 Figure Newsletter Business - Chris Cerra | Episode 5 | The LetterStack Podcast

Speaker A: Welcome to episode five of the letterstack podcast. Today's guest is a special one. I've been on his newsletter since the earliest days of him writing that newsletter as a passion project. So this is a special one for us. I would like you all to welcome Chris Chera, as he wants it, the last name to be pronounced correctly. And he's the founder of Remote Bayes and Digital Nomad Trip Reports. It's a newsletter covering the best locales at the most affordable prices worldwide. I came in touch with Chris Chera and his newsletter, uh, during the pandemic, but I think post the pandemic, it has gone off and has had thousands of subscribers. So we are going to understand how Chris manages to run a newsletter. He runs additional nomadtrip reports and he is also spinning up multiple ventures as we speak. So. So we are here to have him spill his guts about it. So, Chris, welcome to the show.

Speaker B: Thank you so much, Renga. That's a fantastic introduction and I'm really happy to be here. Uh, talking about my favorite subject, which is email newsletters.

Speaker A: Perfect. Yeah, newsletter happens to be my favorite too. That makes three of us, you, me and the audience. So let's get started. But Chris, before we get started on Remote Base and newsletters, would you mind talking a bit about what your life was before Remote Base?

Speaker B: Yeah, sure. So before Remote Base, I was actually working in quite a boring job. Um, I had a job in financial services in the uk, but it was a very kind of niche area of financial services. It was tax related, it was kind of dry and boring. Um, but my background before that is all in marketing and advertising. That was what I studied and that was where my, like, early roles were, uh, early in career. So coming back to newsletters and email for me was a, it felt like coming home. It felt like a bit of a round circle moment where I came back to the thing that I was always really passionate about and always doing before. So it was quite nice.

Speaker A: Awesome. And very always passionate about traveling. Being a Digital Nomad, before Digital Nomad became a thing worldwide.

Speaker B: Um, I don't know if I was like the first, the first person or the first wave, but it was definitely an interest for me. Like, I was always really interested in traveling and that was kind of how things led into Remote Base. So I was working at, uh, a financial services company which traditionally as an industry, you know, it's very buttoned up, we would say in the uk, like, very traditional, very kind of classic, uh, established protocols for how one might work. Um, but the Company that I work,

Speaker A: I've been in consulting. So you are preaching to the coil. So.

Speaker B: Yeah, yeah, yes. Um, but it was, it was an interesting role because this company was actually not like that at all. They were really progressive and really forward thinking. So Even back in 2016 I was, I was gifted this opportunity to work remotely. And that for me became the first, probably the first step to remote base. It was. I always loved to travel. So I got this job, I got this job and I, I actually moved. I'd moved. I was in London previously and I'd moved back to London to go and integrate into this new team. And on my first day I joined a call with somebody who was in my team and they were, uh, it was a guy called Jeff, he's a Canadian guy who was working from Croatia. And I was like, huh, Uh, I just moved back to London for this. Okay, cool. Um, and eventually that turned into me working, you know, remotely at, uh, first just from home in London and then progressively m moving further and further away and working away more and more. And that was ultimately what led to remote base, where we find and curate the best accommodation deals for the digital nomad or the traveling remote worker. Um, so it was a very kind of. It wasn't a straight line, it was a very wavy path from day job in London to managing a newsletter business. Um, yeah, right.

Speaker A: And I understand, Chris, we found each other and you know, you probably got me on as one of the early subscribers in a slack community called WeWork remotely.

Speaker B: Yes.

Speaker A: But was it hard for you to get your first target audience to understand if this idea has legs, if this newsletter is going to take off? How did you find your first thousand, two thousand subscribers?

Speaker B: Yeah, it's a good question. At the time I didn't really think about it as being so important because I had a day job and this was just like a side project. It was something for me to do for fun. Uh, I was, I guess I was missing a little bit, getting my hands dirty in a marketing world, um, while I was in this financial services role. So this became a really fun project. I launched it in the WeWork remotely Slack group. Um, and that came after first talking about it there to see like, hey, how many. Hey. Like I, this is how I live. I work remotely and I travel. Everybody in that community works remotely or was looking for a remote job. And that was a bit of a sense check for me. It's like, hey guys, put your hand up if you are interested in this, in this thing. Is this something that you would subscribe to. And a bunch of people put their hands up. Yeah, yeah, me, me. And eventually that's why I launched it there. Uh, and at that time, 2016. 20. It was around 2019 by the time I launched Remote Base. So at that time it was pre pandemic. Remote work was bubbling away and growing, but it didn't have this kind of post pandemic explosion that we see now. So there was only really a handful of small slack groups or online forums where people were talking about this stuff and like building community. And I just shared it in those places. And I think the first day there was 112 subscribers. And I was like, oh, I guess I have to now send an email. I, um, guess this is a real thing then. So that's how it started. And it built from there. So one day was 112 and it went very, very slowly to a thousand. I think the first, it took me multiple years to get to a thousand because it was just, I didn't have a big Instagram following. I didn't, I wasn't building the brand anywhere. There wasn't even a blog. So there was no SEO. It was just a landing page with a box. And the only way that you could find it is if you got a direct link in one of these slack groups or I respond to a comment in a Facebook group or somebody on the list shares, um, got picked up by a few bloggers. So there was a little bit of SEO, like borrowed SEO from these people. But it was really low touch from me, which on reflection is a bit of a mistake. I should have put more effort into that, um, had I known what I know now. But that was really how it started. And it was probably around the time of about a thousand subscribers where I started to give it more attention and more consideration for, okay, maybe I could not do my day job. Maybe this is my new day job. Let's think about that a bit more and see what pursuing that could look like.

Speaker A: Awesome. And you talk about eventually coming to a point where you decided probably, you know, worth it to quit your full time day job and do this. What's the tipping point, uh, in the remote base journey when that happened?

Speaker B: M. I think for me it was a little bit unique because I had this cataclysmic event of the pandemic, um, to hurry things along. Yeah, yeah. But I think now, like making this decision now is in a more stable world is way, probably way easier. Uh, for me it was like everything I paused a little bit in the pandemic because, you know, people couldn't even travel. And it, it didn't really sit well with me. I wasn't really comfortable like sharing about, hey, this is how you can go and travel in the midst of all this chaos. Um, and it was only when the world had like, reemerged again and people started to travel again, I focused my energy back on it. So it was paused for about nine months or ten months in total. And that was the point where I said, okay, now I, I take the off ramp. So what that looked like for my job was I went part time and I then slowly went. I did something like three days a week on my old job. Um, and I spent two days a week on more newsletter stuff. Outside of the world of newsletters. That was really challenging for me, like splitting my time for the first three, four months. I thought, hey, this is great. You know, I have like a four day weekend. Um, and I was just doing more of my fun project in, in my off time. But actually after that I actually didn't feel too good about it. I felt like I was doing two things badly. And that's obviously not a, it's not a satisfying place to be. Um, so that was when I decided, okay, I have to make a choice. I either go back and do something full time or I go all in with the newsletter stuff. And I'd already done the day job, so I decided not to do that anymore and go all in with newsletters. And, and I went kind of blind. You know, people say, like, you speak to anybody who launches a business or goes to pursue a side project, they tell people, tell you different approaches. One is like, burn the boats, you know, like quit and just go sell your house. Go all in. And the other option is stay very, very stable until you have revenue and things like this.

Speaker A: Right.

Speaker B: Um, and I think I was kind of somewhere in the middle when I went part time and I had to choose. Ultimately it was more of a burn the boat situation for me because I didn't really, at that time, I didn't have stable sponsorship revenue. I hadn't even launched a paid version of the newsletter yet. So it was very risky, on reflection.

Speaker A: Sure, sure. I mean, I think going back in hindsight, everybody's plan to, you know, start a new business completely out of turn is going to sound risky and reckless, if you might call it. But I just want to know, uh, at that point in time, by the way, when you started your newsletter, what platform were you on? Were you on kit.com?

Speaker B: um, maybe. This is, I don't even know if it still exists. But the first kind of webpage for it was on Weebly. And um, and that was hooked up to mailchimp. And then slowly then it went to the website or like the page that I was using for landing pages. I went through multiple different platforms. It was on CARRD at one point. Then I was using Tilda. Uh, I used WordPress, which I think is like, I think to use WordPress to collect email addresses is so stupid. I think it's like, it's like trying to put a picture on the wall with a sledgehammer. It's just. Don't do it. Um, and yeah, I went through all these different platforms, but in the background, mailchimp was still primarily how we were sending emails until maybe 2023. It was around the time that Beehive came on the scene and I kind of watched very carefully what they were doing. Um, anybody listening who maybe doesn't know like Beehive knew at this point and they had a really great team behind them. They were constantly building new features and they still are now. Um, but I didn't want to move because I, I'd since then launched the paid version of the newsletter and while they were still developing it, it wasn't quite per, uh, like transitioning a paid newsletter with the kind of segmentation that I had. It wasn't clear for me how to do that yet. So I, uh, what I actually did was I moved the free newsletter first and I kept running the paid version with all this tricky segmentation on mailchimp until I could replicate it comfortably on Beehive. Uh, so I had this overlap period where I was running two systems for like two months or something.

Speaker A: Sure. Actually you're not the only one. There are multiple other folks who have coming onto the podcast, came onto the podcast who did this sort of in between route of being able to keep both systems running. Yeah, you're not the only one. So I guess that was a prudent move after all. Right. Um, one thing that I always wanted to ask at this point in time, M remote base is what, 50,000, 60,000 subscribers on the free version?

Speaker B: Uh, on the free version around like as in now or when we migrated?

Speaker A: No, as of today. Yeah.

Speaker B: Now we have 10,000.

Speaker A: 10,000. Great. And, and, and there must be a percentage of that on paid.

Speaker B: I believe there's a percentage of it on paid, but it's not. I think my paid newsletter is probably not as, um, conversion optimized as it could be. And that's been honestly that's been a bit of an operational challenge on my side. Like, I always found myself like a clock, you know, like a pendulum swinging. Like I would go from focusing really heavily on sponsorship and building like brand partnerships and then that would do really well and then the pendulum would swing back and I could focus on the paid premium, like upgrade conversions and everything there. And it just kind of swings and swings and swings. And the. I found for my audience and my list, like the, the reward is like the pendulum doesn't swing evenly. The reward for uh, the effort is really unfavorably leaning towards the sponsorship side of things. So I'll spend a little bit more time over there. And over time that's compounded to the. I feel like I've almost been a bit negligent with some of the conversion stuff for the paid and eventually like that will swing back. Um, I've also launched new projects. Um, so again that becomes like a, another dimension to the pendulum.

Speaker A: Um, but yeah, we actually want to know more about the new projects too. But before we get there, just one more aspect that I've always wanted to discuss with you. I know these are vetted travel and accommodation listings, um, that people could go after, both in the free version and the paid version. But the free version has sponsorship revenue attached to it. Um, at some point in time, I'm guessing it takes quite a bit of diligence and discipline to be able to get to vetted listings. So how much time do you actually end up doing this? And do you have a team doing this, Chris, with you?

Speaker B: So the way that uh, the way that it's broken out is it's probably better as well to kind of explain why the content looks like. So in the really early days, some people had, it was very flattering to me, had described the remote based newsletter as like Scott's cheap flights for Airbnb. So, um, maybe people are familiar with these like flight hacking emails where they monitor all the airlines and they send you the best deals. Kind of what we. Yeah, yeah, like what we were basically doing is this exact system but for uh, Airbnb on like long term bookings, like one month or more. So an email would look like a list of 10, 15, 20, uh, accommodation listings with the details around where it is, the price, the rating, things like this. And putting these emails together is as you allude to, quite arduous. It's a little bit tedious to have to slowly move things over, especially, um, without the ability, even in Beehive, like on the plan that we have we can't create via API the, the email. Um, so a lot of time goes on like building the email, um, in the way that we need it to look and feel. So I have a, I have an assistant that helps me with all of that stuff. Um, there's one assistant, she helps me on this publication, on another publication and some like, general operational stuff. Uh, I then have somebody who helps me part time on like business ops. Um, things like invoicing and chasing things and some calendar stuff. Not anything. It's not like we have a huge team. You know, it's super. Email is super, super lean. Um, and that's it in terms of how we actually source the deals. That is a little bit of. There's a lot of time and a little bit of magic with like, we automate what we can, but it can't all be automated and there's always like a final check. And that final check I think has it. It's taken me. I've probably put out like hundreds or maybe thousands of hours into these, into these emails over six or seven years. But I think that's paid off hugely when I think about the quality of the subscriber that we have even today. And like people like you, right, who joined right at the start and stayed on the list. Um, yeah, true.

Speaker A: Yeah. Who. I mean, I'm just like anybody else who doesn't like a good deal. Right. So I definitely can't stay out of that loop. So for sure. Um, one thing. I have noticed this, and you could probably answer this because I've been dying to ask this question to you. Uh, every newsletter creator is told that stick to a schedule. Let people expect your newsletter every time on Saturday morning at 4, 4pm or 4am Sorry. And you know, people would like to stick to a schedule. It also keeps them sane, I would say, amongst everything going on in their lives. But your newsletters are bi weekly, if I understand it correctly. But they sometimes arrive on Mondays, on Saturdays, on Wednesdays. So I look forward to it. But the suspense keeps killing me. So I want to know what's the science behind it or is there no rhyme or reason behind it and you just want to make me mad. Yeah. So tell me, which one is that?

Speaker B: I love the, the attention. First of all, thank you for paying such close attention. Uh, I think that's incredible. Um, we do, we do keep a schedule. Um, but it's not. Maybe it's. It's less obvious as daily or weekly we send. Remote base sends the free newsletter, uh, the second of the month and on the 18th of the month, which is like, roughly, you know, roughly two weeks, um, in between. So it's roughly every two weeks, but it's always on a slightly different day. And honestly, the stupid reason for this or the. It makes no sense. It's a very selfish reason, actually. I didn't ever want to have to send an email on New Year's Day. I always wanted to have that day completely to myself. And I also. So my birthday is on the 19th, so I also didn't ever want to send an email on. I didn't want to have to work on an email campaign on my birthday. So I was like, okay, roughly two weeks. It's the 18th. That's. That's fine.

Speaker A: We'll.

Speaker B: We'll roll with that. And it stuck. It just stuck, um, over time. Like, you're not the first person to have said. I keep you guessing. Uh, and I think actually now it's. Maybe it's nice because it. People don't always know to expect on a certain day, so it feels like a surprise when they get this email and it's got thousands of dollars of savings on accommodation, and they're like, oh, I must quickly go into it and see it. So there's a little bit of a mistake of anticipation that's created. But, uh, that's the real reason behind it.

Speaker A: Awesome. Glad that you told me that. Finally, the cat's out of the bag. So I know that, Chris, you're doing not just Remot Remote Base and the premium version of Remote Base, we're doing Digital Nomad Trip Reports, and there are other businesses I'm sure you're spinning up on the side. We'll talk more on that. But Digital Nomad Trip Reports, right? I'm guessing this is something that came out of your unique perspective that you get. Being able to curate travel listings, being able to understand how people travel, and book and accommodations, too. Did that come about with spending a lot of time with the audience at Remote Base, or is that something that is completely siloed outside of Remote Base?

Speaker B: I think I was encouraged by the Remote Base audience and seeing everything there. But this was a. There was a two, maybe two or three different things that encouraged me to launch that. First of all, like, I'm. While I'm moving around, traveling one, two months at a time, staying in these amazing. Getting these amazing deals on apartments. Um, I was also having, like, you meet other people that do the same thing and you have conversations with them. And one of the, like, the number one conversation is, where have you been and where are you going? And what tends to happen is these, all of these conversations happen, they all happen in the same kind of format, roughly. And it's like a knowledge exchange. It's a one to one knowledge exchange. And I, I think they're amazing because you get so much more rich information out of that conversation than you do if you try to Google what to do in a place or where to stay. Um, so I wanted to take the magic of that conversation and make it a one to many conversation. And this was already happening in like different corners of the Internet, places like Reddit, there's a whole subreddit for uh, digital nomads and people would post their uh, experiences there. I decided to test the idea a little bit by sharing these trip reports on LinkedIn where in a kind of post pandemic world there was more interest in travel and remote work and all of these good things. And they were really well received. And I thought, okay, how can we like take more, take more ownership of this and take it off LinkedIn, right, because we don't want, we don't want an algorithm layer between us and our readers. So that was kind of where the idea came from. And there's an interesting story behind that list, which was somebody else had a list that they were closing. It wasn't really the same kind of content, but it was very similar. It was a guy who was interviewing remote workers who had gone to another country to work remotely. So he, his mission was to, to do like 192 emails and each one would be like one somebody from one each, like one of each country from around the world working from somewhere else. And I think he did like 50, he'd done a lot and he got a bit bored or he wanted to move to another project. But he'd grown the list and it was only a small list, it was less than a thousand people. Um, but he announced, hey, I'm gonna stop doing this. And I, being a nerd, I had been on the list for a long time and loved reading it. And I'd engaged with him before and I messaged him back straight away. I was like, hey, I'm about to launch this thing. It's very, very aligned. Maybe there's a way that we could do a deal. Um, because the format for trip reports is that I never write the content. In the early days I kind of submitted some reports, but the intention was always to grow it and have it be community led, community generated. Um, especially in this world of like AI, AI driven content. I Wanted to have verified accounts from real people who'd been to these real places and had real experiences to share that they could give. Um, so that's all. It's a very community led publication. All of the content is sourced via an airtable form and then an assistant just formats it into beehive and tidies it up if it's necessary. And then it gets scheduled and it's ready to send. So um, that's super light touch. I never have to worry about content generation. Um, and because of that, like, that aspect being very similar to this idea of interviewing remote workers, we managed to come to an agreement where he announced it to the list that this would be happening and gave people the chance to like unsubscribe and leave. And then of the people who were remaining, I would pay a per, ah, subscriber rate and I got a really good deal on it. Um, and a lot of the original subscribers actually never left. So it was, it was a really good, um, yeah, it was a really good deal for me and I think for him it meant that he got to see this project kind of not die, uh, not. It got to continue in a slightly different form. So it worked really well for everybody.

Speaker A: Amazing. So the Digital Metric reports, I'm guessing it's probably not as big as Remote Base is, or I could be wrong.

Speaker B: It's just over. Somewhere over 2,000. Somewhere between 2,000, 2,500. And that sends weekly on Friday and it's completely free. We just run, we run small sponsorships on it and that's it.

Speaker A: So yeah, that's the schedule for you folks who would like to stick to a schedule if you don't want to, you know, Ms. M. Christmas, birthday and New Year's, that's the schedule you look forward to for Digital Nomad Trip Reports. But there's Digital Nomad Trip Post that's remote based. There's Remote Based Premium. But I hear that you are not sitting on your laurels yet. You're spinning up yet another venture. I, I believe I. You have learned a lot being on the field, being able to understand the discipline and the rigor it takes to publishing a frequent newsletter. And I'm guessing that you're also building a venture which puts you in a consulting role, if I might put it that way. Uh, and I understand it's called Mad Banana Media, is that right?

Speaker B: Yeah, there's a.

Speaker A: What's that all about, Chris?

Speaker B: There's a running joke, um, is that uh, sometimes when people like friends always comment that I always have a Banana close by because I really like bananas. And that was kind of where the name came from for Mad Banana Media because I wanted to have something that didn't sound like a traditional media company name. I wanted it to be a little bit wacky and represent uh, like I actually have a banana on my desk even now. Um, but uh, no joke, um, yeah, I wanted it to kind of represent this new world of media and I wanted it to be something that would stand out and I think it does. Um, but really that's about giving all of my current publications a home. Um, because things were a little bit not disjointed but they just weren't so connected. Um, so now remote based Digital Nomad Trip Reports I work on another publication with a partner and uh, I, and we, I do, I was already doing like informal consulting for uh, other entrepreneurs in my network with their businesses or their uh, publications. And so I wanted a way to wrap all of this activity in one, in one place. And Mad Banana Media is basically that. So we offer three, roughly three services. Um, the first one is like auditing your existing email operations, everything that you're doing and the idea there is to just course correct you and stop you from doing all the things that you shouldn't do and make you do more things that you should do. Beyond that we can do a full strategy. So we'll, we'll help craft a full kind of all encompassing email newsletter strategy. And we do this for uh, business owners or brand managers or creators, um, I think a lot of creators now after seeing what happened to bloggers with Google updates, creators, especially in the video world or the more visual creators, start to understand that actually there's real power in owning the relationship with your audience. So we help those um, and then the final service that we offer is something that I call the email doctor service, which is basically where we, it's very light touch. We subscribe to your email and we just respond, we reply to every email and we give you feedback and critique things. So there's a bit of an onboarding process to make sure that we understand what you're trying to achieve. And then once that's done it becomes very light touch. Uh, and that means that we can do it at a uh, very kind of affordable, reasonable price, especially for people who are early. Um, and they get a lot of, they get a lot of value out of it is the purpose of that. And I say roughly three services because there's the hidden service which I don't like to talk about, which is when People come to me and they say, chris, I've been writing my email newsletter. It doesn't work. I don't like it. Everything's not, it's wrong, it doesn't work. I write it and it doesn't work. So the problem is you need to write it, we need somebody else to write it, and then the problem, then that problem will be solved. And I say, okay, sure, we could do that, but let's not do that because probably that's not the real problem. The real problem isn't that you can't write it. You probably can write it. And if you have the time and the resources to write it now, then let's build a strategy that will be, that will be successful and then continue to write it and build it according to a strategy and probably then you'll have a lot more success. Um, so we can do that, but I don't like to say that we can do it because it's not always the right way forward.

Speaker A: True, but, but that's a lot of things being done under one umbrella. So I'm glad that you're going through it without getting your hat on fire. So kudos to you to be able to compartmentalize and give each of these ventures dedicated time and effort. Plus, I know that, um, you know, this is also very cataclysmic event, if I might put it that way. You know, a lot of jobs are being obliterated by AI, A lot of people are getting laid off, but they also have had never had a better time to be able to explore where their passion projects could take them. And I believe just like you took that LEAP somewhere in 2019, 2020, I'm hoping that a lot of people are also wanting to do that. So if you were to be in their shoes today, uh, could you offer any tips on, um, what could people do to build the next remote base that blows up in probably 26, 27? Any, any tips from your end to start today?

Speaker B: Um, it's a really good question. I would say start organic and I guess start because a lot of people will, will block themselves before they even get started. Um, so just get the landing page. You know, all of the best, all of the best providers now, whether it's Kit or Beehive or Mailerlite, whatever, they all give you the option to just have one login that does everything. So just get the login and play around and treat it like, treat it like a game, get started. And when it comes to maybe more serious tips, start organic early. Go and find out where your perfect reader is and just be there and get early organic subscribers because they will set you up for future success into like far into the future. Um, and engage with them very, very closely. Like follow up with them personally. Try to create early relationships. Um, yeah, I think that, I think that's the perfect way to start. After that you can then worry about like optimizing and how to, how to think about click rates and all this other stuff. But I think if you're looking to get started, don't try not to go into that rabbit hole because that can be really off putting and overwhelming and just start with the basic stuff.

Speaker A: Yeah.

Speaker B: What do you think? What do you think?

Speaker A: No. Yeah. Get to 110 subscribers and then you realize, oh my God, I've got to do this every week now just to keep those 112 people happy. Same here. Letterstack is not that big. Uh, you know, we are close to thousand right now. But I'm writing as if I am having thousand people in a room. Yeah, I get to talk to them every day. Even getting to talk to them every day would be great. If some of them choose to leave the room, that's okay. But the fact that 900 odd still continue to stay in the room is good enough for me. That's enough validation for me to keep going.

Speaker B: Yeah.

Speaker A: And, uh, this is an exciting space. I believe. Even with you starting five years ago, I would wager that you still think that the space is still getting warmed up. There's more to come. Especially with TikTok losing its audience. You know, uh, sometimes it gains it, sometimes it loses. That depends on what month of year is it. Right. Ah, so the only way to be able to own an audience is either through community, which takes a lot of effort, and email, which does not. So all it takes is for you to show up every time. Right. Uh, so if you are able to do that, I think that would be great. That's my two cents. But you have lived the dream and you're doing it multiple times over. Uh, Chris, so I'm glad that you know, we had you on the show. So thank you so much for coming on the show. Thanks for taking out the time. And folks, if you love traveling or if you love bananas, go check out Chris's website. You should be able to check out both Remote Base and Mad Banana Media. And if you have any questions, drop it to Chris himself. He responds to every dm. That's how he came onto this show. So I'm guessing he will respond to your DM too, so feel free to reach out to him. Thank you so much once again and look forward to many such episodes from Letters Tank. Thank you.