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Welcome to Travel Buddy
In episode 20 of the Travel Buddy Podcast we sit down with Switchfly's CEO, Nowell Outlaw, to learn more about the realities of true remote work. We explore lifestyles that go beyond the norm including what it's like traveling the world while maintaining a job. Gain insights on the logistics and challenges of balancing work and travel from diverse locations, along with the cultural shifts that facilitate such lifestyles. Are you interested in embracing a nomadic work life?
Key Highlights
- Detailed experiences of people working from unconventional settings, such as off-grid locations and traveling in vans.
- Use of TrustedHousesitters as a cost-effective solution for travelers managing pet care.
- Challenges and solutions for maintaining work schedules across different time zones.
- Impact of long-term travel on family bonding and educational experiences for children.
- Discussion on the balance required between employer expectations and living a nomadic lifestyle.
Quotes
- "People have figured out this lifestyle where you can go to different places. And as long as you have internet, you can work from anywhere." – Nowell Outlaw
- "Traveling when you're going day after day after day is really hard and it's exhausting. It's better to live in a place, immerse, and then move." – Nowell Outlaw
Transcript
Brandon Giella (00:01.512)
Hello, Noel, and welcome back to the Travel Buddy podcast. Today, we are going to be talking about remote work and not just remote work because everybody's been talking about that for years ever since COVID and even before. But today I want to talk about like real remote work, like people that are literally like off grid or are traveling all year or I had a colleague who would take, get a, like a van.
during the summer and drive all across the country and was working from the back of her van out in the middle of nowhere, you know, with some kind of satellite deal. So that's what I want to talk about. But I also want to get your take on as an employer, what you, how you think about remote work in that way for your team or what expectations you have and their culture, just things like that I think would be helpful. And I know this is a big complicated topic, but tell me a little bit about
How do people do this? How do people do real remote work for a long period of time? How does that happen?
Nowell Outlaw (01:05.098)
It's one, it has to be the right skill set, right? So, you know, we were just talking about like a physician, probably not, unless you go to, know, physicians without borders and one of those, those kinds of things. I think that what's interesting. So my wife and I were just in Scotland, right? For a couple of weeks. And we found a website, I'll plug them here called trusted house sitters.com, right?
Brandon Giella (01:10.323)
Hmm.
Nowell Outlaw (01:33.332)
And you register for trusted house sitters.com as a pet owner. And basically I think it's 150 bucks for us to, to apply for this or whatever. And you can go find someone. it's like dating for people who are going to stay in your house and watch your animals. Right. So, you know, we filled it out and literally within 24 hours had a couple that, that basically sent us a note.
We did a zoom call with them. We're like, yeah, let's do it. Right now, because the rates just went up for us to board our dogs. I fell over when I heard this the other day for two dogs at this boarding place, it's $190 a night. It's a hotel room a night. And this is not a fancy place. like, and you bring the dog food, right? For them to basically watch your dogs.
Brandon Giella (02:21.841)
What?
Brandon Giella (02:29.278)
Yes.
Nowell Outlaw (02:31.338)
And basically self-service, it's $190 a night. And I'm like, wait a minute, if you're taking a two week trip, a three week trip, this is crazy. Right. And, and, and so we use trusted house sitters one, there's an economic benefit of it, but the people that stayed with us, very nice couple. He's from, England and she's from Michigan. He's a programmer and she's a German tutor.
Brandon Giella (02:41.574)
Yeah.
Nowell Outlaw (03:00.384)
online for people, right? And so they have this very remote oriented thing and they've figured out how to really live without having a house payment, right? Because I don't pay them to stay in my house. They just do it for free. So they're getting an income, but they don't have a mortgage. And literally they, they were at another place in Colorado. Then they came to our house and then they went to Portland, I think.
And then they were in Costa Rica and then they're like they're all over the world, right? Just doing this kind of, you know, staying, watching people's animals, you know, living this kind of virtual nomadic lifestyle, right?
Brandon Giella (03:43.508)
But for the economic benefit, like for you, is of course I'll do that. I'll pay whatever. But I have so many questions. mean, do you feel like you had to lock up your valuables? how did you, it didn't really matter, I guess?
Nowell Outlaw (03:46.604)
That's
Nowell Outlaw (03:56.844)
Not really. yeah, I mean, we don't have stuff that is laying around for people to, I mean, I guess they could, but, you know, but it, but it's, I think for us, it's more about, you know, taking care of your pets. All right. That's the hardest part in it. And, you know, and they, they actually came over ahead of time, which we got really lucky, but you know, they did tell us some people need to show up and the, the keys under the mat.
Brandon Giella (04:04.993)
Sure, yeah. Yeah, sure.
Brandon Giella (04:12.648)
Yeah, of course.
Nowell Outlaw (04:24.332)
the people have already left and the dogs in the closet, right? Basically are in the storage room or whatever. And that's it. You never actually meet the person that for my wife, that's, that's pushing a little bit. But I think the, I think that there is a world out there of people that travel, right? And they do this. her name's Lisa, right? She actually spent, I think she said two months in the Galapagos working on a horse rescue thing. Right. And so she, you know,
Brandon Giella (04:42.151)
Yeah.
Nowell Outlaw (04:54.19)
people have figured out this lifestyle where you can go to different places. And as long as you have internet, right, and let's be real, Zoom is the way of the world now, right? No one's going back. That what you have is you have environments where people either, you know, we have remote employees, right? So we have people in India, we people in Mexico, we have people, 26 states, right, all over the place. So as a company, we're
Brandon Giella (05:01.651)
Mm-hmm.
Mm-hmm. Mm-hmm.
Nowell Outlaw (05:23.828)
always used to having remote people just in general. And what we've seen is we do have some employees that are kind of travel working professionally, right? And some people are very good at that, right? Some people aren't so good. And that's where my employer hat goes on, which is, you know, I think it can't be
Brandon Giella (05:26.856)
Mm-hmm.
Brandon Giella (05:38.803)
Hmm.
Brandon Giella (05:45.907)
Hmm.
Nowell Outlaw (05:51.182)
disadvantage to the employer, right? And when, you know, and also, you know, you have to have approvals and all this other stuff. But, you know, I think the other piece is, you know, you can take your laptop and you can be anywhere, but you also have to maintain the work kind of hours with your team, let's say. And what I mean by that is, you know, if you're in, you know, Germany,
Brandon Giella (06:14.792)
Mm-hmm.
Nowell Outlaw (06:20.056)
you know, you're eight, nine hours ahead. Man, if you want to be out drinking a beer at seven o'clock, it's probably not going to happen, right? Because you might need to be on calls and your, your company is not going to necessarily bend all the rules to fit your time zone. Right? So you're going to have to live like, one of our employees just left for Thailand. He's there for five or six weeks. Guess what? He's having to work.
from like 10 PM like he's having to work the midnight shift but that's expectation so it's like well if you want to do that you know that's okay so so think i think you have to pay attention to the hours right unless you're just a programmer at night no one cares and you don't have to interact with anybody but that's not the norm these days
Brandon Giella (07:10.824)
Yeah, I think it's becoming more common. think it's like, I was thinking of, when Airbnb came out or Uber came out, there was this like cultural shift, like I'm gonna use somebody else's house or somebody else's like car. But then when it, as it relates to remote work, I think things are becoming more asynchronous. Like people are writing things down more and there's more like cultural practices around that. But there is a lot of that synchronous work. I mean, we have seven team members on our team. A couple of them are in Africa.
Nowell Outlaw (07:22.03)
Mm-hmm.
Brandon Giella (07:40.89)
They work overnight and I've had I've had to be able to on Sunday night I've got to set them up well because they're gonna be working while I'm sleeping So there's a bunch of that kind of thing, but but I'm curious. How do you how do you recommend people?
Nowell Outlaw (07:47.798)
sure.
Brandon Giella (07:54.558)
think about, I guess, like pulling this off, like as it becomes more of a cultural norm. And I'm, I'm trying to think like, okay, I want to do that. I want to go to Europe. I want to work, you know, I can work mostly asynchronously and I can go to Europe and live there, but I've got a, a little tiny baby girl that I love so much and she is going to be two years old in February. And I'm trying to think like, how do I have a baby? How do I run a company? How do I work with my team? The Schengen visas, I think if you go to Europe, you get 90 days there.
Nowell Outlaw (08:20.686)
Yeah. Correct.
Brandon Giella (08:24.454)
then you gotta take 180 days back. Like what are all the things that you would recommend for people or at least to think through as they're trying to do that life?
Nowell Outlaw (08:32.096)
Yeah, I think that, so, you know, we spent six months driving through South America, right? And what you learn, you know, first of all, when you're traveling for longer than two weeks or three weeks, you're the way you travel is different, right? So you're not, you know, you're not going and doing like, you have a lot of people, they get one week, they go to Disneyland, they're doing something every day, go, go, go, go, go, before you can get on a plane and go back home, right?
Brandon Giella (08:51.479)
Okay, yeah.
Brandon Giella (09:01.085)
you
Nowell Outlaw (09:01.774)
And when you're taking a longer period of time, you know, you're more immersed in what's going on around you and you're just living. Right. So it doesn't really matter if you're living in your house now, or you're living in a house in another country, right? You still are going to make dinner. You're still going to go to the store. You're still going to do this stuff. And what you end up doing is okay. On the weekend, just like if you're in Dallas, right? let's go to the park on the weekend. Right. The,
the normalcy, right, just starts to appear. And so like when we did it, you know, we would go and we would, you know, stay in a place for three weeks and then we would move. And so we'd have a couple of days of moving and then back in a place for three weeks, right? So you're, you're more structured. I don't think, you know, traveling when you're going day after day after day is really hard and it's, it is exhausting and I've done it and
Brandon Giella (09:56.166)
exhausting.
Nowell Outlaw (10:01.154)
I think that you need to, I would rather go and say, we're going to live in Scotland, or we're going to live in Ireland, or we're going to live in Chile. We're going to do that for six weeks. And then we're going to go and do the, that we're going to move everybody. And now we're going to go be in South Africa for six weeks. And airplane there, get settled, get to know it. Okay, now we're going to move to the next place for six weeks.
And I think people do more of that than you realize, right? I think the moving someplace every week is crazy. Like, I don't know if that's even possible. So I know people do it, but man, it's insane.
Brandon Giella (10:40.308)
Yeah. Yeah. Yeah, it's grueling. It's grueling. One thing I do think is like, I would love to travel that much, but also relationships and community is really important here locally. You know, I mean, yeah, I just think like, it's so hard to like have family and things like that when you're traveling so much, but it's, maybe it's just seasonal. Maybe it's just a season in your life.
Nowell Outlaw (10:59.874)
You know, it.
I will tell you, it goes really fast. Right? So, you know, we pulled the kids out of school for, you know, the back, the back half a semester and we're gone for six months. Like we, we had a lady that rented out our house. She actually watched our animals as well. And we were gone, like just, and you came back and there, there is that reentry, like, Whoa, like welcome to lots of plastic and stuff that you're not used to, but.
Brandon Giella (11:06.195)
Hmm, really.
Nowell Outlaw (11:32.398)
you realize like not much changes really like you're gone for six months you've done all this stuff but you come back and it's like yeah hey like how's it going everyone's still getting the mail doing the normal stuff what did you do we went here for spring break and then we're back at work kids are at school it's it's in six months not that much changes right
Brandon Giella (11:44.084)
That's interesting.
Brandon Giella (11:55.774)
Did your kid's school give you a hard time? Because I can imagine some teachers being like, hey, we got geometry going that whole month, you know, or whatever.
Nowell Outlaw (11:59.214)
we, yeah. So our boys, when we did this, Gavin was fifth grade and Hayden was, I think, eighth grade. And that's the hardest part, right? And I think as kids get older into high school and the, know, unless you can teach the chemistry class, you have to find a way around it, right? And some, some high schools and things support this and kids can dial in over Zoom and things to learn. For us,
Brandon Giella (12:20.69)
Yeah.
Nowell Outlaw (12:29.302)
the our middle school basically gave us here's what you have to keep up on and for Gavin, you know, we did the same kind of thing. And it was great, right? I mean, we were doing natural science, learning, reading about volcanoes while we were hiking a volcano in Chile and looking down the chutes, right, where the lava comes out and stuff. And then when we were leaving, like two days later, it exploded. But, right. But like there's real life lessons there. And I think that for kids,
Brandon Giella (12:57.223)
Yeah.
Nowell Outlaw (12:59.054)
It's great. We as a family, having done that, it is a bonding thing as a family. Even now, we still refer back to that time as just we make jokes about it and things that happened on that trip that only we know about as a family. I think it actually brought us closer together. Yes, there's tense moments and there's that.
Brandon Giella (13:05.235)
Mm-hmm.
Brandon Giella (13:18.163)
you
Nowell Outlaw (13:27.552)
Okay, trying to find your way into a place and getting in and getting settled and the kids and we got robbed and all this other stuff. But, you know, I would do it again and a heartbeat, right? And, I think it's, it's well worth it to do it. And, know, even at 18 months, you know, you know, maybe a little bit older, but the difference to your kid between being in Dallas and being in Iceland, they don't know.
Brandon Giella (13:56.638)
Yeah. Yeah. Yeah.
Nowell Outlaw (13:57.39)
They have no idea. I think the community that you have will be the community that is there when you come back. People are connected in all kinds of different ways.
Brandon Giella (14:05.848)
I def-
Brandon Giella (14:11.432)
Yeah, 100%. Yeah. Yeah. Yeah. I definitely can't study a volcano here in Texas. So that is, that is a great education. No, I love that idea. I mean, we talked to, as a family about wanting to travel like that, but having a baby would be hard, but maybe there is that window that it's actually not too bad. Let's say from like two or three years old to eight, nine, 10 years old, it's actually pretty doable.
Nowell Outlaw (14:18.186)
No, you cannot. Yeah.
Nowell Outlaw (14:34.584)
Yep. We met a couple from Australia. Like whenever you're traveling the world, you meet Australians and go, they're crazy. Like they're, they're doing what? And same thing. They were, they were traveling for six months. They had a newborn. And I mean like under 12 months old newborn, a three year old, and I think a six year old. And they were just doing it. They rented these houses and they were like cranking through. They would be there for two weeks and then moved to another place for another couple of weeks.
Brandon Giella (14:41.077)
I agree, yes.
Nowell Outlaw (15:04.36)
And they were just living, right? Is I think the way to look at it is like, okay, I'm going to live here now for two to three weeks, then we're going to move someplace else. And it's just how nimble are you, right? You can't take the pack and play and the this and that, like all the stuff that we build up. Our kids have slept in a drawer, like pull the drawer out, put a blanket in, that's your bed, right? When they were little.
You you can, you just have to be flexible.
Brandon Giella (15:33.95)
Gotta be flexible. Yeah, I like that.
Well, there's so much that we could dive into to this topic. I would love to hear more maybe in a future episode about you being an employer and what that is like, because I think that is such a tension between a lot of conversations that are happening in the news today and the way that employees feel about their organization and the way that work gets done. mean, there's so much to explore there in a way, especially as a travel company and you guys the way that you can execute on it. So I'd love to talk about that sometime.
But Noel, as always, thank you so much for this, this thought. I, I am excited to try to plan a trip and maybe, live my life somewhere else. And I know a lot of people feel that way. So, yeah, thanks to you so much. All right. We'll talk soon. See you.
Nowell Outlaw (16:10.574)
Thanks, Brandon.
