Digital Nomad Life
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Brian: [00:00:00] you're about to hear my conversation with Dru Riley, where we get into the lifestyle of a digital nomad. Let's get into it.

So I'm about to roll my conversation with Dru Reilly. He's back on the show today and on this one, we talk all about his. Work life as a digital nomad. So in the previous episode that I did with Dru, we talked all about his business, trends. vc, it's a fantastic newsletter business, tons of systems and incredible operation and business that he's grown there, but he's been able to do that from living.

All over the world in different locations. So I wanted to really unpack this and understand what that lifestyle looks like. It's a really good, it's a really great conversation. Here it is. Here's my chat with Dru about digital nomad life. Enjoy.

So we're back here with, with Dru Riley. Dru, thanks for coming back and we're gonna continue [00:01:00] our conversation. Um, in the last episode, we talked all about your business trends vc. That was a really great chat. But in this one I wanna talk about Nomad life.

Dru : okay. I'm looking forward to it.

Where in the world is Dru?
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Brian: Where are you right now? That's, that's my first question.

Dru : Yeah, so I'm in Mexico City right now, my favorite place in the world. And it's kind of ironic we're talking about nom matting because. This time in particular, I've 90, I've made the decision like 95% certainty. I'll make this my base next year. So what does base mean?

Yeah. I spend six months at least out of the year here. And then, you know, I may like travel the other six months, and Mexico City is good for that because they have a rainy season and then they have times like this where every dish is just beautiful.

Brian: Yeah, I hear so many great things about me, Mexico City, and I've never been there. I gotta get down there.

Dru : I would recommend it. Let me know when you come. I have, I think 230 pinned places in Google Maps,

Brian: Oh, wow.

Dru : I think it's hard to compare to any [00:02:00] American city because American cities, it feels like they're built for cars first. And that's not the, the feeling that you get here at all. It's a very it's a, it's a proper city.

Brian: Yeah, yeah. Very cool. So how long have you been doing this, like, moving around and, and you know, nomad life, if you will?

Dru : Almost, almost three years. February of 2024 will make three years. And I did a trial run of this back in, maybe that was 2018 when I did a solo trip through Europe and I learned some things that I was able to apply to when I eventually started Nomad Full-time. The biggest thing I learned is that if you switch places, I'll speak for myself.

If I split switch places too often, I sort of stop trying to build relationships or, you know, invest in friendships. And that's why this time around most places I go to, I typically stay there for three months. So I was three months in Turkey, three months in the Canary Islands. And then places like Mexico City that I come back to a lot, you can just sort of

You know, [00:03:00] pick up those relationships and keep running with them. That's how I found my Juujitsu gym here. Yeah.

Brian: Oh, nice. Yeah, I was, I was gonna ask you like, how long in each place? Like three, three months or so. That sounds, that sounds pretty cool. I mean, what is like the benefit of,

Dru : like,

Why choose the digital nomad lifestyle?
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Brian: of doing this? Like why do you love it so much? How come you've been at it for three years? Uh, yeah. What, what's the, what's the draw for, for people who, who don't do this kind of thing?

Dru : It has its drawbacks. But first let's talk about the draws.

So I have this idea of comfort challenges that I talk about a lot where I consider a comfort challenge. Like anything you do that's new and or uncomfortable. And I feel like that's just the way we grow. That's the way we expand our world, is by doing these new and or uncomfortable things.

And no mading feels like a way to kind of turn that idea into like a life where. I'd never been to Grand Canaria before. So, you know, there are infinitely [00:04:00] like new things there and like in terms of for example, that was the first coworking space that I went to where they had monitors and you can't see it.

But now I have like the secondary monitor because I was able to draw this connection between how productive I feel and how much screen space I have. I'm sure there's some upper limit, but there is . You know, this I don't know, before the, the, the, the benefits start to even out there,

Brian: funny, I'm, I'm, I actually just got rid of my second monitor. I'm just like trying out, like going back to the single thing. A little bit more focused. I

Dru : Yeah. I had a big curved monitor, like 34 inch in Atlanta. So it's not about multiple monitors for me, but it is about having enough real estate. But yeah, that's just one example of okay, I don't think I would've discovered that, and that's a tiny example, but discovered that if I was just sort of in, you know, locked in, in Atlanta, uh, yeah.

Different cultures, the way they treat people. I try to, it was Becky Food for the first time in Turkey. I love, love, love it. So, it's, it's, [00:05:00] it's, it's. It's a way to turn comfort challenges into a way of life, just because if you're just trying to live, but you're in a new place, you can't rely on the old habits that have gotten you to where you are.

It's just like habit rot isn't real when you're constantly on the move, and that's one of many benefits.

Brian: I, I could totally see that. I mean, my family and I love to travel. We, we did like a mini nomad thing back in 2015. It was basically just around the us just, you know, Airbnb in different places for a couple months each. And we've, we've done a bit of travel through Europe, but other than that, we just do a lot of like vacation travel, which is like very, very different from what, from what you're talking about.

Like you like. You're really setting up shop and like living in a place for, for three months and, and really in, you know, getting like, ingrained in it.

Dru : Yeah. And to go back to habits like this way of life, I'm really, really big on habits. And you can probably pick that up from our previous conversations on systems, but it forces you to design your [00:06:00] habits and design your life in a way that's. Anti-Fragile isn't the word, but robust where it can withstand different environments.

Right. So back in Atlanta, to give you a very specific example, I like doing debt lifts with hex bars, but maybe 10 or 20% of gyms actually have hex bars. So you know, you better learn how to debt lift with a regular barbell. That's just a tiny example. But you may not have a bike everywhere you go, so figure out other ways to exercise.

Or some cities like Istanbul aren't conducive to biking, so you just learn to roll with the punches and build like a very, you know, robust system around your

Brian: Yeah, you get like super flexible, like in instead of like, oh, they don't have my my workout system or, or, or this or that food. Instead of saying like, oh, I'll just take a break from working out. You're gonna have other, other ways to get it done.

Dru : absolutely.

Favorite places (so far)?
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Brian: I love it. Um. Favorite places like you, obviously Mexico City.

Dru : yeah, Mexico City is

Brian: other, other, like highlights that, that you'd like point out to as like some, some favorite [00:07:00] spots.

Dru : As much crap as I give American cities, I still love Atlanta. It doesn't have, it's next, not next to a body of water, which some people will critique. Traffic can get pretty crazy, which some people can critique. But just in terms of food, the mix between sort of urban living and nature, uh, is great.

The airport, you can have a direct flight to almost anywhere in the world.

Brian: Yeah. It's a big hub.

Dru : Yeah. Great mix of cultures. So Mexico City, I still love Atlanta. What are some other places? Lima, I was surprised by Lima and I think I went at a good time of the year because as I would interact with different people and talk about how much I love it, people are like, you love it now?

Like, wait until a few months from now. And it's called like the, a foggy desert, so it won't rain, but it becomes very foggy and very hard to see at certain parts of the year in Lima. So.

Brian: Hmm.

Dru : Yeah, I tried surfing there. Surfers loved that. That

Brian: oh yeah.

Dru : Yeah.

Working across timezones
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Brian: How has it been for you going, whether it's Europe [00:08:00] or like Asia, you know, like, and dealing with time zones and I, I'm sure your whole team is remote, obviously, but like, has, has that had an impact on how you work and, you know, 'cause like, I, I've had some friends who they, like most of their company is based in the us but then they go live in Europe for, for a period of time. and it's pretty disruptive. Like they have to literally do their work in, at like nighttime hours and, and shift their schedule around. Have, have, you have to dealt with any of that?

Dru : Yeah, this gets back into, I guess, management and sort of, so we only have one call per week, like everyone's calls are on Mondays with our analyst slash editor slash marketer. We have monthly check-in our monthly one-on-one. And then with our operations person, we have biweekly one-on-ones, and then just the team has a 90 minute call each Monday.

So that kind of limits the need for everyone to be running, you know, on. At the same time, I would co-work with some people in [00:09:00] Istanbul where they have to be online from like 8:00 PM to 4:00 PM 'cause it's like the company is in California, things like that. So we don't necessarily have those issues. And I actually like the jump from, you know, America's type time zones to Europe or even Istanbul because I can start my day later if I want to.

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Dru : and you know, our check-in call instead of being at 10:00 AM it might be at 4:00 PM or something, which is okay.

Brian: Nice.

Dru : It has kept me from Asia. I've been to Asia before, but that was back before trends vc because I think . That will become very hard to navigate, right? Where you're almost on the opposite time as everyone else.

Yeah.

Brian: Just a few months ago we, we were in Philippines and Cambodia and and yeah, that is my, um, I. It's literally out, especially when you're in the Philippines, you're literally a 12 hours difference from, from where I live in the us And [00:10:00] it's I mean it's literally night and day like, you know, not, not only the jet lag just getting there, but like, like when I'm working, my team is you know, just getting up or something like that. Different thing.

Dru : and that's the only thing that's kept me away from Asia in the last three years, because otherwise there's so many places. The Philippines, I would love to go Cambodia, Vietnam, I would love to go, but.

Brian: Yeah, there's so much to see out there and that, that I, I've, we've only been, we've been to the Philippines three times. My wife has has some family there and and then we try to hit like one other spot, one every time we go there and done, like Bangkok and Cambodia haven't really done too much in China other than Hong Kong.

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Brian: but

it's like

Dru : like

Brian: that, that whole side of the world. is, is where every culture is, is different in its own ways. But that's where I feel like, wow, this is like a whole, literally a whole other side of the world here, [00:11:00] you know,

Dru : Mm-Hmm.

Processes for life as a nomad
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Brian: Crazy. All right. I want to get a little bit back into like the systems and processes, Um, like
What is your, so you know, you talked about like three months, give or take in, in each place. Like what is your process for like. Identifying like where to next? You know, researching and, and, and preparing and then, and then landing in the place and getting situated. Like, how, how are you, you, you've been through that enough times now, like I'm sure you, you've, you've figured out some hacks and some streamlining things and,

Yeah.

Dru : Yeah. Yeah. One of the first things I do to go back to I talked about having like 300, 230 pins in Mexico City of like sort of places to check out. That's the first thing I'll do before I book a flight or before I seriously consider going to a place. And I think this strategy like. For me, it exposed the weaknesses of American cities because any place I go to, I try to look for where can I build my 10 minute town?

Meaning that the place that I'm gonna work from, whether it's a cafe [00:12:00] or coworking spaces that in relation to my gym, in relation to good restaurants, in relation to where I'm staying, they're all like within a 10 minute walk of each other. Just because it reduces friction, it means that I work out more often.

I Get access to better food without wasting too much time transitioning between places. So if I start to drop these pins and there are no, like concentration, like very convenient areas, I just, that goes to the bottom of my list. And I, I just won't go. What else goes into this process?

Researching upcoming destinations
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Brian: I guess like in the research thing, 'cause I run into this when I'm just planning upcoming trips and stuff to, to new places. Like do you, how, how are you able to like, get a feel for deciding on your your home base from being afar? Like is it literally just like.

Dru : just like

Brian: The concentration of like restaurants and businesses in this area. That, that looks pretty good.

Dru : I mean, that, that leads the research process for me. Another thing I'll do, [00:13:00] but I wouldn't say that this is one of the first things that I'll do but go to YouTube and look at like walking, not walking tours, but people who just have cameras on their neck and they're just, they're not talking, they're just walking the streets.

And that gives you a completely different feeling than you might get from like a travel PIA type video where someone put together a documentary about the place. Like what is this like? On a Wednesday at 2:00 PM in the afternoon and you're just walking. So I'll, I'll tend to do that with some places, but it really just comes down to like quality of life, convenience.

I also check out the weather of like, what is the weather like this time of year? But the thing that really rules the day for me is that I'm looking for a very, very high concentration of sort of places that I would be interested in and that I would use a lot. Right? Not the . You know, is this tourist destination next to where I'm living at?

I don't care about that. Like, I went to Istanbul and I don't think I, I'm not saying this to brag, but went to the Grand Bazaar at all. Like I'm just, you know, really interested in quality of life [00:14:00] and, you know, show me the laundromat, give me a bus ticket. You know, what is life like here?

Brian: Nice.

Finding places to stay
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Brian: Are you using like Airbnb or other, how, how are you finding places to stay?

Dru : Yeah, I'd say 80% of the time it's Airbnb. And in some places not this time around, but the last few times I've come to Mexico City I took advantage of this like apartment, hotel, they're called Sonder, where they're like apartments, but you can just rent them out in a more flexible way. And then that's another thing that when it comes to picking a place, I try to look for over time, you build these preferences.

So I know I want a washer and dryer, a patio, a full kitchen, a separate bedroom, so not a loft, right? I need to separate where I work from, where I lay my head at.

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Dru : and then it's can you find a place at a reasonable price next to all of these other things? So it's really this crazy optimization problem.

Brian: Yeah. All right. So. Getting there. You, you land like day one or week one, like what's your, [00:15:00] what's your process for like get getting, getting all set up,

Dru : Week one. I wanna walk, no, I'd say a tour. I prefer biking tours over walking tours, just because you cover more ground, but it kind of exactly gives you this sort of context or depth for where are you at, like what's the history of this place. And it completely changes your experience Once you have that context where, where you're at within that first week, I'll join a gym.

I'll try to figure out, I'll try like a lot of different coworking spaces and cafes to sort of build a short list and I want at least three just because I don't want to go back to the same place every day in a row, but kind of switch them up of, this is my Tuesday and Thursday's place. if I didn't, I think I already mentioned a gym.

That's really it. Other than that, I just, you know. Certain places have strengths that other places don't. I really like the Hamams in Istanbul, but there's no Hamam that I know of or that I would trust in Mexico City . So, you

Brian: What are you

Dru : Yeah.

Social scenes as a digital nomad
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Brian: what about like, like social scene and like, you know, both like work scene and just, [00:16:00] just getting out and meeting people? I. I don't know if it's like, 'cause like how like shy I am as, as an adult and like, and I, I find like actually like hanging out and like making friends locally a lot more difficult here in my hometown than like online and through our industry and at, at conferences and things like that. And on social and stuff like that. So like how do you.
I I almost feel like doing what you do, like, like nomad life. It, it might make it easier to like kind of, I'm, I'm here for three months. Like this is an Opportunity to meet some people. How, how are you going about that?

Dru : I think that question is also a function of sort of place and culture. For example, Istanbul, very, very, very open culture. Like I remember going to this cafe. mEt a guy, I think he was from Afghanistan, and then the next day we're coworking from a library, just because I didn't consider, like, again, it goes to different places, have different strengths.

The library's in Istanbul, I can't speak for all of Turkey, but they're very, very good places to cowork from. But that wasn't on my radar. And we [00:17:00] just struck up a conversation because he needed a like Thunderbolt cable or something . And then the next day, you know, we're co-working out of a library together.

But would I expect for that to happen in, you know, grand Canary? No. Just because there's a different culture there.

Dru : I also find myself meeting a lot of people at the gym, and I don't like small gyms, but a benefit of small gyms. Sometimes you have to share equipment, so you end up striking up a conversation there.

Yeah. So gyms, cafes tender if you're single. Yeah.

Challenges of living and working as a nomad
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Brian: Very cool. All right. I want to kind of circle back and we'll, we'll wrap this up here, but like, you know, Maybe some of the challenges, but I, I think it's interesting that you talked about how Mexico city is sort of becoming your home base or even just the idea of having a home base.

Dru : home base. Mm-Hmm.

Brian: Yeah, like can you speak a little bit about that? Like what, what do you think now are like the benefits of like, like, so you're, I guess you're still nomad life, you know, doing that, [00:18:00] thing, but you'll sort of like return to, to Mexico City.

Dru : yeah. Yeah. And. I, I typically say like, I'm slow matting, so it doesn't feel like that much of a dif difference for me. I wouldn't be surprised if we did a breakdown of the last three years and I've spent, you know, close to six months in Mexico City as is. I would just break it up instead of it being a continuous stretch because it's a place I come back to more often.

And then even if that wasn't the case, it's not that much of a switch because I'm spending, you know, . Three months in Portugal, or three months here. So it's like the difference between spending three months in a place and six months in a place, I don't think it's a huge jump. Right. And then I, I, I don't see a, an end in sight when it comes to no mattering, just because of those benefits.

But there are, you know, some drawbacks, right. Of, I feel like. A lot of visas are designed this way where as an American you may get an automatic 90 days, but it's like, I feel like I just, you know, started to wrap my head around this place and get some of those efficiencies [00:19:00] of, you know, living here and knowing where to go and now I have to leave.

So,

Brian: Mm-Hmm.

Dru : I can start to kind of, I guess, benefit from that more of having more of a base.

Brian: Yeah. Yeah, I can see that. Super exciting, man. I, I wanna, like, I, you know, my wife and I always talk about like, doing this thing again, but now that we have kids growing up in the, in the schools and everything, I feel like we're kind of locked down. And then we we we do most of our traveling in the summer, but, it, it, it's exciting. I'm always kind of jealous of folks like you, who you have to travel the, the globe and do this thing.

Dru : They, I think school is sort of a big objection or reason not to do it. But I'll try to send you some episodes. I listen to a lot of nom matting podcasts where you have families that do this and you know, they have different ways that they solve, like schooling challenges and things like that.

Yeah,

Brian: Yeah. Very cool. Good stuff. Great to catch up, Dru.

Dru : likewise.

Brian: All right. See you.

Dru : So, yeah.