I’m really excited today to bring on Chris Cerra, who is the founder of Remote Base, a really cool startup.

I saw you made a post on LinkedIn about meeting some brothers. Was that on your travels to Chiang Mai?

No, that was years ago. So, I’m doing a challenge at the moment of writing every day for 30 days and sharing that across Twitter, LinkedIn and other media. I thought it would be a fun thing to write about the magical moments that you experience when you’re just on the road. The idea is not to make a sweet big assumption that everyone’s done some aspect of travel because it’s a privilege to be able to do it. But, one of the things that I thought would be good to share is just reminders of how fun it is and those small moments that in the moment they seem very small and very insignificant, but when you reflect later you realize that actually a really cool thing happened today, or actually a really cool thing happened three years ago. When I look back and piece it together, the stuff that happened years ago changed the entire trajectory of your life.

That was a story about two brothers who were also actually from the US and they were in Italy in Tuscany, piecing together some of their family history. I think maybe they’d use some inheritance to get themselves there and go and find out more about their millennial roots.

I like to dive into what makes people who they are. Can you explain a bit about your background?

I’m originally from Manchester. I lived in London for a long time, and I think that London is one of those places where anybody who spends enough time there forgets where they’re from, and all of a sudden, they identify as a Londoner. Now, I don’t think I’m really from anywhere. People are like, where are you from? I have no idea.

I always wanted to travel and international travel wasn’t something that I did a lot of when I was growing up. So I took it upon myself at the earliest possible opportunity to go and do as much of it as I possibly could. Basically, when I graduated, there was this small window that I had and now I need to fill this window that I have with travel because once that window closes, then I’m going to have a job. If you don’t go now, then you’re never going to go. So, that’s what I did.

I did this thing called interrailing. It’s this company called Interrail. I think it’s called the Rail Pass and you pay for one ticket and it’s a ticket for any train in any country in Europe for 30 days. You don’t have to do any of the planning ahead, booking this train at this time. You just turn onto the station and travel. The trains are mostly quite quick and clean and on schedule, so it’s a really convenient and cool way to get around. It’s a lot cheaper than flying and a lot better for the environment.

I planned a 30-day trip, but I actually got sick in Barcelona, which meant I had to fly home on day 22 or 23, and that was it. I toured a lot, I was like 90% of the way there. The only country that I really missed was France. Then I came back and I got a job. I worked in some different startups and then moved into technology companies. I ended up working in a really niche area of tax consultancy for technology companies. Now, I run Remote Base.

Did you get all the way to Istanbul and Turkey using Interrail?

No, I didn’t. This was my first foray. I guess I romanticized it a little bit. I think everybody romanticizes travel to some degree. Google Maps wasn’t what it is today, but Google Maps was a thing and you could use it to get around. But I had a little take on maps and tried to remember the names of the streets between the station and the place where I was trying to stay. I wanted to try and navigate it in the least tainted way. I wanted it to be pure. I was trying to avoid scenarios where I would rely on technology and that would mean that I didn’t have a conversation with somebody. If you are lost in some random country, you should go and ask somebody for directions. You shouldn’t just pull out your phone and try to figure it out that way. I wanted to have as many human connections as possible.

Rome, Italy

I started in Germany and I did Germany, the Czech Republic, Hungary, and Italy. I probably spent about a third of my time in Italy – in different cities there. When you’re traveling on a budget, there are some things that you decide, okay, I’m going to go above and beyond here and pay for this. And instead of taking the train from Italy, I took what they call a one-night cruise from Civitavecchia, which is the port closest to Rome, across the Mediterranean to Barcelona. I wanted to pay for it as my splurge, but I didn’t want to pay for a cabin with a bed. So, I had to sleep on ferry seating. That’s how I got to Barcelona where I eventually flew home from.

Would you recommend the one-night cruise from Italy to Spain?

I slept terribly, but one of the benefits of that was when I went up to the top deck and some of the colors I saw were colors that I’d never seen before and I don’t think I’ve ever seen again; such a stunning sunrise. I’ve been on some ferries and they’ve got a bar and a vending machine. But these had proper stuff. They had cabins with beds if you opted for that. I was just on budget at that point.

What are some travel-related issues that you’ve come across while traveling?

Language is the first thing that comes to mind for me. I think I have a bit of a complex when it comes to languages. I feel guilty that I’m a native English speaker. I’m in Thailand and I meet somebody and they’re from Germany. Guess what language we converse in? English. I’m in Spain and I meet somebody new from China, and guess what language we’re conversing in? English. It makes me feel lazy and as if I’m entitled.

If I could have any superpower, I’d want to be able to speak every single language. How amazing would it be to be able to speak to people in their native language? How much closer would you get to all of the different cultures that exist and nuances in language, and jokes, and play on words in another language? I think that’d be amazing, but there’s no incentive for me to do it because everybody’s English will always be better. It’s a long way off and it feels like an uphill battle if I go to a country and I try to speak their language, they know that that’s not my first language and they default to English. If you are a linguist and already want to travel or have traveled, you are less turned off by the idea of that being a problem.

Also, probably the other thing is that the more you travel, I think you become more aware of the differences that you observe in the world in terms of social demographics, socioeconomic standing, and the privileges that you have, especially if you’re coming from a western country or any developed country and you go somewhere less developed. Being aware of it is enough because slowly it will impact the way that you think, the way that you see the world, and the actions that you take.

What is the story behind the platform that you’ve developed, Remote Base?

Remote Base is an email newsletter. I think it’s probably really important to let that stand by itself for a moment. It’s not a booking platform, we don’t own property, and we don’t manage property. It’s not a travel agent. I don’t like being a travel agent, since it’s just the same solution to a problem repeated as opposed to a slightly different solution being applied. So, it’s a free newsletter and that means that you give me your email address and I send you emails full of accommodation deals.

We basically specialize in long-stay accommodation that is perfect for remote work and travel. The digital nomad audience are the people that we send our deals to. Long-stay is anything more than one month or more than 28 days. The way that we find most of these deals is through Airbnb, but 5-10% of them come through our relationships that we’re able to build because of the audience. So, because of the sheer size of the audience and how niche it is, people are happy to offer special rates or discounts that are exclusive for Remote Base members. And that’s it. Remote Base is an accommodation newsletter for digital nomads.

Remote Base logo

Is Remote Base global or regional? What kind of deals do people get from the Remote Base newsletter?

The high-level answer is global and then, the slightly more detailed answer to that is we will tell you about the deals wherever they are. People always would ask me, ‘Hey, I just signed up, next week I’m going to Prague, tell me where I can stay now?’ I can’t do that. I don’t control what’s available in Prague next week. What I can do is always have our finger on the pulse or on deals that are emerging, where they are, and we just scoop them up, pick the best ones.

There’s a lot of stuff that might be highly discounted or be available at a really good price, but it’s total junk and you don’t want to stay there. I consider this to be part of the service and that is curation. We find it all, we filter out the bad ones, and we just give you this nice list for you to pick from and for you to kind of be inspired by. You might sign up to this and we might send you a handful of bios and you might literally be interested in none of them. The whole point of this is to give you inspiration on where you can possibly go in the world and serve those up to you. Basically, it brings the deals to you instead of you having to go and do that hard work.

I’ve been living out of Airbnbs and traveling the world, working online for four and five years. Sometimes, it is really hard to find a place or you find a place and it turns out not to be very good. We do as much investigation and due diligence to help you relieve yourself of that stress. So, it’s a curated list of the places that are possible to go to, and one of the things that I think is important is that if you live this lifestyle, you have the option to basically say, ‘Hey, this email looks great, this place is available within three months time. I don’t know where I’m going to be in three months’ time, I’m going to go there’, and you book it.

What is the timeline of the deals in the Remote Base newsletter and how frequently does it go out?

So, the free newsletter goes out twice a month. It used to just go once a month, but we recently started going twice a month because people want more deals, and all of the deals are available three months from now. We know through surveys and general market research that people are looking at places about three months in advance, so that’s why the free newsletter is built around that to cover the most bases and to give you enough time to plan ahead, book a flight, or whatever else it is that you need to do to make that booking possible. But in terms of how quickly you have to act, I think that really depends on the place.

How many people are on the Remote Base newsletter?

About 2,200 people.

So, you have to act quickly to get that property.

Yeah, very true. And probably the other thing is the day after I send the newsletter, maybe the price changes. Airbnb has a lot of smart algorithms that decide what price is best for a property based on things like the lead time between now and the check-in, and a whole load of other factors. Maybe if you wait a day, everything can be booked up or be more expensive.

Some people want to have deals sent to them that are more immediate and other people are power planners and they want to see really far in advance. We also have our premium membership. It’s $68 a year and for that annual price, you basically get to set your preferences like what continents you’re interested in visiting, how many bedrooms you need, and you also get to share your budget preferences. So, that means that we only send you the things that are applicable and you get to see lots more stuff than the free members get, and part of that includes getting stuff available either very far in advance, so you can power plan to your heart’s content, or stuff that’s available on a very short notice like it’s available next month or it’s a last-minute deal.

How do you go about finding the Remote Base deals? Have you created algorithms or is it manual labor?

For anybody listening with a technical mind, I’ll say Airbnb has an API, but it’s closed. It’s invite only. And it’s more geared toward property managers who want to serve their own properties to an audience on a white-label site. For less-technical people, like me, I would say it’s also very against Airbnb’s terms of service to try and scrape Airbnb. So, we automate as much as possible, but there’s always some aspect of it, which has to be manual. We can’t automate the entire process, but I think that’s good. I’m quite happy with the balance that we have at the moment because it gives us the opportunity to quality-check everything and catch things that otherwise would slip through the net. For example, sometimes stuff comes in and it’s golden, but then you realize there’s no Wi-Fi.

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This newsletter should exist so that as many people as possible can enter the world of remote work and travel. They can test it out if they want to test it out and they can see if it’s for them. Because of that, it’s really important to me that everything we send is super high quality. I don’t want people to have a bad experience. For me, working remotely and the freedom that it gave me to travel and pursue all of the other things in my life that I wanted to pursue is fundamentally life-changing. So, Remote Base exists as a vehicle for me to give that gift to other people. So I don’t ever want it to be subpar quality. I want it to be good stuff.

How can you make the digital nomad global mobility space more enjoyable?

I wish all of the stuff that’s available now was available when I started because it would’ve made life so much easier. Now is the best time to start because there’s so much available to support you on that journey. So, anyone listening who’s thinking about it, you just have got to do it, you just have got to try it.

I meet people and they ask loads of questions and you don’t really realize how much you know. You forget all of the things that you had to learn and struggle with. For example, I’m going to this country and I know that my phone plan doesn’t cover me there. I know I’m going to need to get a local sim and I probably have two or three different ways to get it. But if you’ve never been to Asia, you’ve probably got no idea about how telecoms work here. So, if you’re somebody in a position to share that knowledge, answer the questions that the new wave of nomads have. I think it’s important.

How would you recommend experienced travelers give back besides building companies?

The example I gave of just answering questions that people have is an option. Right now, I’m here in Chiang Mai and there’s so many people here who are on their first trip, or their first solo trip, or their first time in Asia, their first time in Thailand, and they have questions. I think there will be questions that you find yourself being asked and you’re probably in a really good position to answer them. What I would like to advocate for is that people don’t just say, people don’t just think to themselves, ‘This is annoying, all these people asking me about sim cards’. Try and remember that actually there was a time when you didn’t know a telecom provider and you needed to ask that question. It’s like paying it forward and helping people on that journey.

What was your experience starting Remote Base?

I had a bit of a peak and trough experience, but that was more Covid-induced. When I started Remote Base, it was early 2019. It was like a cool toy that I could play with in my downtime. It all started because I found really good discounts and when you have 10-12 tabs open, you need to close everything down. So I put all of these cool deals into an Airbnb wishlist. Then the wishlist started to get really big and I was probably not going to be able to stay in all of these, so maybe I should share them with other people who might be able to stay in them. I was in some Slack communities at the time, so I shared them there and that’s how it started.

It was just something that I was doing for fun. But I knew eventually, if it goes really well, there’d probably be a way to monetize it. I didn’t really know what it was, maybe I could get commissions from bookings and stuff like that, but that wasn’t really the goal. It was more like, let’s get these deals out there – let’s get some people moving around the world here.

I worked full-time alongside that for a year, maybe two years. It still wasn’t monetized at this point, and then early 2022 was when I was able to monetize and stopped working on my day job. I remember the first time I loaded the new subscriber page and it was like 112 people and I thought, ‘Oh my God, there’s more than a hundred people here and I can press buttons and they’ll get an email from me. This is insane’.

Then very quickly, it just trickled up through that year and Covid happened. Through the pandemic, it didn’t really sit very well with me personally from a moral standpoint to be promoting travel and encouraging people to move around the world. So, I paused all operations, and when borders started to finally open and airlines started to make announcements about flights, and there were fairly consistent testing regimes and testing requirements emerged, that was the point when I figured people might be into this again. And actually, more people than ever went into it because they’d had two years of being trapped in one place.

For the people who’d been through training camp for remote work and had decided they wanted to be on the team, they leveled up, they wanted to go and travel and try and do it from somewhere else. So, there was a lot more engagement generally speaking. Now, we’re well over 2000 people, and we monetize with the premium membership and some sponsorships of the free newsletter. We work with people like VPN companies or travel insurance companies and relevant products.

How did it feel to actually be able to commit to Remote Base full-time?

It’s definitely a nice feeling. I think after two years out of a pandemic, I was ready for the next chapter of work and I was ready to just put time into this.

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If I was more dedicated in the earlier days, I probably could have got things off the ground quicker. I think when you are starting out, there’s always a bit of introspection and a lot of stuff going on internally. Is this a good idea? Is this going to be successful? Am I the right person to make it work? All of this stuff. And every day is different, you ebb and flow through this cycle of ‘This is amazing, we have a new sponsor’ or ‘I’m on the podcast’, and then the other days ‘That campaign went out and I don’t like how many people unsubscribed’. You have to take it as it comes and just have some balance, but fundamentally, it’s a lot of fun.

What makes Malaysia (where you have settled) attractive as a location? Do you see yourself there long-term?

I think this is just where I am right now. If you’d have caught me in January, I would’ve been in Columbia. Between then and now, I was in Europe, I was in Portugal for a long time, and now I’m on this side. So, it really depends. We tend to move around every couple of months, from country to country. If we’re on a continent, then we’ll try and move around within a continent. Basically, the end goal is just to have two or three places around the world that we know we like and be able to just cycle through them, and spend time in the same places at the same time of year and get to experience some of the variety. For most people, if you work a day job or you are based in one location, you might spend 50 weeks of the year in one place, and then you have two weeks when you go on vacation. Wouldn’t it be nice to have like four months in the mountains in Europe, four months by the beach in South America, and then four months in like a big city in Asia, or some combination of those things? That’s the end goal for us, to narrow through travel and shortlist places that will end on this two to three-place list that we cycle through.

What two or three places anywhere in the world are best to visit?

That’s hard. I think probably Porto in Portugal. I’m torn between the last two places that we have been to. So, here in Chiang Mai, because I love it here. It’s one of the first places that we came to when we came to do a long stay. So, I think it’s got a piece of my heart. Just before this, we were in Malaysia, in Kuala Lumpur, and the food is just insane there, so it’s a very convenient place. And then, the final place would have to be somewhere by the beach. I’ve never been, but I’d really like to explore Central and South America more, so maybe some beach over there like Costa Rica. It changes based on the last place that we went to, but I think Porto is definitely on the list and now we just need to find the other places.

What one piece of advice based on your experiences would you give?

I would say never make any assumptions. I think it’s really important when you travel to go to every place without any preconception of the place, or the people, or anything. Just go there with your eyes wide open.

Where can people sign up for the Remote Base newsletter?

If you’re interested in the idea of a newsletter and you want to stop overpaying for Airbnbs, then come and sign up to the newsletter that’s at remotebase.co. It is as simple as just putting in your email address, pressing the big orange button, and I’ll see you in your inbox. If you want to contact me, you can just reply to the welcome email and it comes directly to my inbox. You can also follow me on LinkedIn or Twitter. Remote Base is also on Instagram. That’s a good place to come behind the scenes on some of the deal-finding stuff and see the latest things. If people are interested in the premium membership, we’ll put together a discount code, just for Random Citizen listeners.

Chris, thanks so much. I’ve had a blast and really excellent insight.