RWL053 Greg How to Quit the 9-to-5 and Build a Remote Career Around the World with Greg

Living and Working Abroad Success Story

Speaker 1

0:00

Greg. So where are you at the moment? Where are you jumping on this call from at the moment?

Speaker 2

0:05

Hey, alex. Today I am in Mexico City. This is my home base these days, but last week I was in Italy and the week before in London. I like to be all over.

Speaker 1

0:15

And that is the beauty of setting up your own company that allows you to be here, there and everywhere, right?

Speaker 2

0:23

That's right. It's a priority for me, so I've sort of made that happen.

Speaker 1

0:27

Nice, you've got to tell me then. So how did you get from where you were to being basically a jet setter? Well, I don't know if it's a jet setter, but having a lifestyle where you can actually you've aligned with your passion for traveling and remote work to, um, you know what you're doing now. How do you get to that point?

Speaker 2

0:50

for sure. So I'll take you back 2014. Uh, and I was living in chicago and I grew up in chicago. I'm from chicago. I've never lived outside of midwest before this and, uh, when I was in university, uh, my friends all got to study abroad. I didn't actually get the opportunity to do that, but I went and visited some of them and just had this amazing experience and this romantic idea of living outside the country that always stuck with me.

Speaker 2

1:14

And you know, I was living in Chicago, working in Chicago the nine to five. You know you commute the same way every single day into sort of a sea of death full of people kind of uninspired by what they're doing, and I just kind of felt stuck. You know, I wanted to do something different. I had this, this romantic dream of living in different countries and, you know, eating local foods and meeting people and having these kinds of just unbelievable life changing experiences. And so what I did was I said I want to do this sustainably and I want to do this in a way that I can do more than a week or two at a time. So the first thing is I found work I could do from anywhere and at the time 2014, I didn't really know about remote work or the fact that you could do it full time for a company. So what I did is I went out and I reached out, reached out to my network and I asked people, do you need some help with strategy or with marketing or anything like that? Um, and one of my friends thankfully had a company and he he needed some help. So we signed a deal for me to start helping them out on a ongoing basis with some marketing strategy, putting up their sort of paid marketing strategy and infrastructure. Um, so that that was it. That was like the day.

Speaker 2

2:26

So when that happened, that night I went to dinner with my group of best friends and I said hey guys, I got this work I can do from anywhere. Do you guys also want to get remote jobs or jobs you can do from anywhere and go travel together? And they all kind of looked at me like I was crazy. These are investment bankers and consultants and professional types of folks and they just didn't even wrap their heads around it. They said that doesn't make any sense. We're not going to go do that with you. What are you talking about? And so the next day I quit my job and I started traveling. I, the same day, wanted to have a group of people to go do that with. So I put up this website and it said who wants to travel together for a year while working remotely? And I sent the link to a couple of friends and they sent it to a couple other friends apparently, and before I knew it the first day, over a thousand people had signed up.

Speaker 1

3:22

Oh my gosh. Wow, totally unexpected, so right when I just got started the same day, over 1,000 people had signed up.

Speaker 2

3:25

Oh my gosh, wow, Totally unexpected. So, right when I just got started the same day, all these things sort of happened, like I got some remote work, I quit my job and then I put up this website and it just sort of all kind of was happening like really fast at the same time, and then over the next few months, more people kept talking about it, journalists started writing about it in the US and then abroad, and before I knew it, 50,000 people had signed up. Totally unexpected, yeah. And so during this time I was traveling, I was kind of you know working and you know doing all these things, but all the while, all these people were saying I want to do this experience, I want to come do this with you from all over the world.

Speaker 2

4:05

And during that I said, wow, there's something here, there's something more. Um, this, this, this could really be something. And so that's when, um, you know, I was talking to one of my best friends, sam, talking about this interest and excitement that this idea was getting, um, and that's when we kind of decided to formalize this into a more formal program and say we can help people do this and really make it into something more than just a group of friends traveling. And so during that experience I sort of went from, you know, working freelance and traveling to building Remote Year over the next you know, couple months, which was sort of unexpected and came about really because I wanted a group of people personally to travel with now that is has got to be the ultimate story in turning your passion into like a successful business.

Speaker 1

4:52

If I ever heard one and I, well, a lot of people I mean when you, when you see all these videos, all these gurus on youtube talking about traveling and and working a lot there's a lot of, obviously, fakers out there, obviously, but for sure you've turned it into something. You've not only have you turned your passion into something that you can do, but you've also brought along with you people who want to do the same thing and doing it really and truly in real life, and they're doing it for a year at a time, right, totally.

Speaker 2

5:25

So we have four month programs and we have 12 month programs. So in each one you live and work in a new place each month throughout the experience, together with a community of 30 to 50 people. So you're doing this, you're working remotely, living in different places, and it is an unbelievable life changing experience to have that opportunity to live abroad, that opportunity to live abroad. But the thing that people really love about Remote Year is the community, is you build this relationship with these folks you share the experience with in ways that you just can't even understand or dream of. It's unbelievable.

Speaker 1

5:58

It's amazing. I've been trying to get hold of Greg for a while to interview him. I'm so glad that he's come on here to really talk about it, to let you know that this is happening. People are doing this.

Speaker 1

6:11

Um, people are, you know, not only working remotely I think remote work is still still people still trying to get to grips with the actual idea and the concept of remote work but they're traveling, they're doing their, what they do professionally, but taking it on the road for four months a year, you know, up to a year at a time. Road for four months a year, you know, up to a year at a time. So it's real and if you want, you know, you should get in touch with Greg. I'm gonna leave a link, obviously, around, just so you can actually see what you're going to. Have a look yourself as well, because if you're dreaming about doing that yourself, greg can make it happen for you.

Speaker 1

6:48

You know, and what I'd ask Greg is I know there's lots of people listening to this that there are remote people listening to this. There are also people who are trying to make not just remote work happen for them, but they're also trying to make traveling while they're working happen as well. So if I'm, you know, I'm now sitting in my cubicle in my digital marketing agency or wherever it may be. Think to myself I need to convince my boss to let me go remote. What steps should I take to do that?

Speaker 2

7:22

Yeah, it's a challenging conversation, right, it's a big ask for lots of people and we've had now over 2, over 2500 people come on our programs and we've we've been part of that conversation thousands of times now. Um, so we've really perfected how to do that best and we actually have a full-time team dedicated to helping people have that conversation with their employer and that's all they do every single day is they help people that conversation? So if people really want to do this and they want to make remote work and travel work for them, they should reach out to us. They should come to remote year.

Speaker 2

7:55

Um, they should reach out to me personally, greg at remote yearcom. Feel free to email me direct and I'm happy to help anyone in the audience that wants it. Um, and we have a team dedicated to helping you do that. So, um, we're we're happy to get on the phones, understand your specific situation, understand what your company's like, and we've built out business cases and all kinds of supporting materials to help people really make the case to their employer to make this possible. So if people want that help, we're here to support. Just come on to remoteyearcom or send me an email, greg at remoteyear, and we'll help you guys out.

Speaker 1

8:26

You might be hearing from me All right, let's do it. No, well, yeah, I eventually want to do it. I mean, I I'm at the point now where I'm probably not quite ready to do it yet. But what I really want to know is, what is there a certain type of? Obviously my community is is a mix of digital marketers and people in tech, for example. But yeah, is there a aside from this, the sort of hard skills? Is there a certain type of person that is part of your community? Are they, you know, are they quite young? Are they what? What sort of demographics are we looking at?

Speaker 2

9:01

yeah, well, first of all, we. Our community is full of curious, driven professionals, and we mean curious and driven professionals all three words very specifically. Everyone is pursuing something professionally throughout the experience and they're really excited to learn and grow as a person on the experience, both personally and professionally. And so that's really who, psychographically, the people are in our community. Other than that, it's pretty diverse. So we have people 22 up until 76. So super, super wide range of folks from over 40 different countries participating. So it's a diverse group of people, all kinds of experiences, all kinds of backgrounds. We are an American company, so there is a larger proportion of Americans than other backgrounds. But other than that, it's really really diverse. And the thing that really binds these people together is that these are people that are excited to learn about new people and ideas and excited to grow personally and professionally and they're really growing while being productive and working throughout the experience.

Speaker 1

10:06

No, I mean, it's great and well, I'd never have thought that. I suppose you don't think again when you see all these images of digital nomads. They're all sort of like Millennials and young looking people and you never imagine so. The reality is far different from the images that we see, and I think another thing that's that, so go ahead I will say that there are a lot of millennials, of course, um, that is.

Speaker 2

10:34

That is a big part of the demographic, for sure, um, but it is more diverse than I think you'd imagine and I think I mean as much as it's it's a great.

Speaker 1

10:43

It's a great. I love the concept, I love the idea of traveling and working. As I said, and there's so many people out there who like it as well. There's still a component of adaptation, especially if you haven't worked remotely before, and I know one big issue in the remote community is and I know obviously you being in a group or community kind of perhaps negates that in some ways, but there are people that might feel a sense of isolation or a sense of loneliness. How are you as a group sort of dealing with that? But also, what sort of recommendations can you make?

Speaker 2

11:22

Yeah, well, I think the way that remote work can become lonely is if you just are working from home and you never leave your home. But we're all about co-working and bringing communities and people together and I think if you ask anyone on our programs, I don't think anyone would say they're lonely, because there's this constant, high energy, social interaction happening at all times. Interaction happening at all times. So that is a really supportive, amazing community that we build. It's outside of the workplace, right, this is more of a social community. But I would say, if you are lonely, if you can't do remote year or you can't do a program that's going to help you have that kind of experience, I would say, at least join a co-working space, because those are some great places to have some social interactions. It gets you out of the home, even if you don't have to go into an office every day.

Speaker 1

12:08

No, definitely. I think the key is I think actually I suffered this myself when I first started working remotely. I worked from home a lot and perhaps at that point, going back 10 years ago now, I did tend to just really sort of engross myself in the work so much that I just kind of one moment I looked out and it was sun and the next minute it was sort of dark outside. So yeah, greg hits on a great point. It's that we're human beings and we need that interaction, we need community, we need people around us, we need that inspiration around us to actually get to do our best work.

Speaker 1

12:50

But, greg, what I want to ask you as well is, again there's a number of people in my community that have their own businesses as well. Well, when I say businesses, they may be freelancers or they're working in relatively small teams. So one big question is as well is about uh, community, so not just community but but um culture as well. I don't know if you, if you're sort of, if this is an area that you delve too much into, but people, a lot of questions I get are around actually building teams, so like building remote teams, and I know that's obviously something that you're doing right now actually, yeah, how do you go about what's your hiring process? How do you go about it?

Speaker 2

13:36

Yeah, I mean. The cool part about remote teams is there's a big talent pool. Lots of people want to work for remote companies. If you put out a job that is open to remote, you're going to get a lot of applicants usually. So that's the great part about remote work.

Speaker 2

13:52

The hard part is vetting those candidates right. You have to understand the right way to get to know people throughout the experience and filter through a big stack of folks. I like to figure out what are the motivations of the person, why are they looking to have this job? And if their motivation is they just want to work remotely, I'm probably less inclined to want to hire that person. I'm looking for people who are much more connected to the mission of what we're doing, and so I like to really find people that we call zealots, people who just love remote year and are so passionate about our mission, and I think any company should be able to really clearly articulate what your mission is, their purpose for being there, and if you can articulate that well, then anyone that you talk to you could find out if the reason they want to work for you is aligned with your mission or if it's more of a mercenary engagement and they really want to work just for the money or just because they have a certain perk or benefit.

Speaker 2

14:48

So that's the first thing that I like to do, and then the other is you really get to know people. We like to do a pretty aggressive referencing process where we get to know other folks that you worked with, learn what that's actually like. We like to get to know people through multiple interviews. For some roles we bring people out and meet them in person. So it's really, you know, taking the time to make sure that the folks that you're bringing onto your team is the right person for the role and for the org you know, and bringing a different, diverse sort of perspective to the table.

Speaker 1

15:21

Okay, and your team must be. I mean, is your team based different parts of the world, or are you mainly America or Europe?

Speaker 2

15:30

Yeah, we have about 110 people now and we're fully distributed all over the world. So we have people across Asia, across Europe, some in Africa. We have people in India, all over LATAM and then a bunch, of course, in North America as well.

Speaker 1

15:45

And typically I mean of that 100, what does your, what I mean? Can you sort of dissect how your team is sort of split up?

Speaker 2

15:54

Yeah, about half the team is on a global operations team. So we have people full time in each of the cities that we operate in. We're operating in 12 different cities globally. We're operating in 12 different cities globally and so we have that infrastructure in place to plan and provide the experience and the what we call infrastructure so the apartments, the co-working spaces, the transport, things like that. So we have a really, really amazing team all over the world to really deliver that experience. And then the rest of the org is on the experience team the product, the finance, the marketing, the set sales and people operations, sort of you know technology, all the different parts that you'd sort of think about.

Speaker 1

16:36

You know you need to support that org. It's amazing. It's an amazing story. It's like you've gone from sort of wanting to travel yourself for work to setting up a business that's distributed across the world. You've got more than 100 people in that business. Did you ever imagine that it would get to this level?

Speaker 2

16:51

You know it, it didn't start there. You know it started with I was kind of looking for sadly, looking for friends to travel with, but it became pretty clear early on from the reactions that we got the excitement, the interest that there's something bigger here and that it could become something pretty important. And you know that's really been, as we've seen that opportunity. Our mission is to build that and we really believe fundamentally that as we enable more people to have this kind of experience who maybe otherwise wouldn't have that opportunity, we build that kind of global understanding and empathy in a way that really makes the world a better place. And that's really important and that's really valuable. And we want to try to have that impact on as many people as we can. And so that's that's why we're, you know, focused on how do we continue to evolve our experience, evolve the way we communicate with the world and evolve the different type of experiences that we offer to make this accessible to as many people as possible wonderful and managing a hundred people.

Speaker 1

17:57

Obviously you've got your managers, who, who help you out, but how do you guys all stay connected in different corners of the of the world? What and what sort of?

Building a Remote Work Culture

Speaker 2

18:07

so I guess, what sort of apps are you not apps, but sort of tech are you using to stay, stay in touch, and sure yeah, I mean, the cool thing about remote work is it didn't used to be possible, but now connectivity is just seeped into every corner of the world and, anywhere you are, you have to be way outside not to be able to have a really strong connection at this point to the Internet that you'd expect. It's, it's zoom, or you know maybe other video conferencing tools. Um, slack is great. We spend a lot of time on slack, um, obviously it's a tool. It's got to be used correctly or else you could waste a lot of time.

Speaker 2

18:45

Oh yeah, chatting and slack, um, and emojing and sending giffies all day. But, uh, slack is a great tool, um, if you use correctly. Obviously, email as well, um, but you know, we like to also have people come together, um, and we have budgets for people to come together, uh, once a year and meet in person, which is a really great way to get to know each other and build trust, so that when you do have these online digital interactions, you do it from a place of empathy and understanding um, a little bit more. But you know, all these things are tools. Any video conferencing tool should be fine. Any chat tool or messaging tool should be fine, as long as you set the right culture around how to use them and how you want to get things done as an org.

Speaker 1

19:30

That's great. And is that those meetings Because I mean speaking to Nick Francis from Help Scout and a number of other remote CEOs like yourself, they have meetups baked into their actual way that they work so that they can, like you said, build that trust and that collaboration that sort of community feel. Is that something that is baked into your culture as well?

Speaker 2

19:59

that sort of community feel. Is that something that is baked into your culture as well? Yeah, yeah, definitely we have. Like I said, we have budget and process for people to meet up once a year with different teams, and that's a big part of it. But I think, you know, truly the digital components are the way that that culture gets reinforced and the work actually gets done. I mean, I think most companies, even companies that are co-located most of that stuff actually happens digitally and that's a big part of how we get things done at Remote Year and, I think, how most people get things done otherwise.

Speaker 2

20:29

You know, one thing that I've been thinking a lot more about is this idea of asynchronous for synchronous communication and there's this big meeting culture and, I'll be honest, at Remote, you're pretty guilty of this. We have all kinds of meetings for all kinds of things. If there's something going to get done, we'll call a meeting and bring everyone together to talk about it live. I've been diving in and talking to a lot of other remote leaders about how they do things and I've been learning about ways that they really sort of inspire and encourage asynchronous written communication, and I'm trying to think about how does that work for us at Remote Year how can we sort of build out some more processes so people can do less meetings and spend more time actually working and being productive through asynchronous written touchpoints? That, I think, is a really exciting idea that some other remote companies, I think, do better than us.

Speaker 2

21:22

One cool example is GitLab. I don't know if you've heard of GitLab, yes, oh, very cool. For anyone who doesn't know, it's a large software tool that helps people collaborate and build software together and they are fully remote and distributed and they have the GitLab handbook, which is publicly published. You can Google it and it has all the different processes that they have internally documented really well and written very clearly. I think that's a really, really cool idea, a really cool concept that I'm trying to think about for us at Remote Year formalizing and publishing different processes that we have around how we do one-on-ones, how we do video conferencing, how we do Slack to sort of take the best practices that we've developed over these years and share them out with the world, but also formalize them a little bit more clearly for folks within our org so there's less confusion.