TMBA603: Returning to Nomadic Life

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Summer is here, and it’s starting to feel like things are returning to “normal.”

For many of us in the community, that means that we’re finally going to have the opportunity to pick up our backpacks and return to nomadic life.

Jesse Schoberg is the co-founder and CEO of, a Software as a Service platform that helps users add blogs to their websites.

Jesse has been a full-time nomad for over 7 years, and he joins us on this week’s podcast to discuss how he was able to transition from running an agency to creating a product, and why he finds the nomadic life so appealing.

If you’re ready to get back on the road, or perhaps you’ve decided that it’s finally time to double down on entrepreneurship and go remote, this is the episode for you.

See the full transcript below

Listen to this week’s show and learn:

  • The origins of (3:32)
  • Why agencies are great entry points into entrepreneurship but so difficult to scale. (10:05)
  • What motivated Jesse to live a nomadic life. (19:27)
  • How you can still “have your own place” while living a nomadic life. (30:18)
  • Jesse’s advice for people who are considering a nomadic life. (46:08)

Mentioned in the episode:

Before the Exit – Our New Book
Partner With Us
The Dynamite Circle
Dynamite Jobs
Dynamite Deals
Tropical MBA on YouTube
Post a Remote Job
Dynamite Jobs – Remote Recruiting Sales Page
Let’s Talk High-Level Podcast Strategy for 1 Hour
Jesse Schoberg on Twitter
The 4-Hour Workweek by Tim Ferriss
Noah Kagan

Enjoyed this podcast? Check out these:

TMBA590: Mailbag: How Long Does it Really Take to Achieve Freedom?
TMBA591: The Surprising Habits of Wealthy People with Noah Kagan
TMBA602: 5 Strategies for Growing an 8-Figure Business

This week’s sponsor:

Today’s podcast is sponsored by Dynamite Jobs.

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Thanks for listening to our show! We’ll be back next Thursday morning 8AM EST.


Dan & Ian



Full Transcript

Jesse: No one in my SaaS is offering me $15,000 today. Agency life is – you hit a big contract, and this big chunk of cash hits the bank account. There’s that kind of rush to it. And it’s really hard to say, ‘No, no, let’s don’t go out and celebrate, let’s focus on working on this product that’s going to release in a year’. Who wants to do that? When you can go make 500 bucks today,

Dan: Alright, we’re back. Welcome back to the pod. This one came directly from a conversation I was already having. Many listeners know that this is the longest I’ve spent in the United States consecutively since 2007/8. So it’s been a big adjustment for me. And there’s a big part of me that just can’t wait to go visit some amazing places around the world. It’s not just me, it’s the listeners of this pod. That’s in part why we’re hosting our first event since the pandemic started in Mexico City this autumn.

So I was on the phone with an old friend who happened to be in Mexico City. And was helping and giving us his insight into what venues will be good and what neighbourhoods and party venues and all this kinds of stuff. And we just got onto talking about business, and lifestyle, and the permanent travel lifestyle and all these TMBA themes started coming out from this podcast. Like how he started from a services business and then productized it a bit and now he’s running a software product business with a big upside. And I’m just having so much fun with this conversation. I said, ‘Hey, Jesse, would you mind calling me back in a few days and flipping on the microphone? Can we do this for the podcast?’ And he agreed. So happy to bring this one to you.

Today’s guest is Jesse Schoberg. Someone I’ve known for a long time and have met in many wonderful places around the world. He has been a full time Nomad with no permanent home, living out of Airbnb for over seven years now. So we’re gonna talk about why not only he finds this Nomad life so appealing, but also extremely practical in the second half of the show.

But first, what we got started with was what turned out to be really interesting for those of you running services businesses and looking for ways to progress into product because in this realm, Jesse has walked that hard path of sort of being stuck in services ,not really stuck, but it was really good. And how he finally made that transition onto a path that has the potential to be much more profitable.

Jesse is the co-founder and CEO of ‘Drop in Blog’,, which is a SaaS platform that allows users to put a blog on any website that was not built in WordPress. So if you run a website on Lead pages, or Shopify, you can use Drop in Blog to host a blog on your site. Now his background is as a developer, but he’s got chops in a lot of other areas, as you’ll hear. And Jesse has two co-founders, whom he’s worked with over many businesses over the years. And they have around 10 members of their remote team all paid hourly. So it’s a pretty tight operation. So I started out by asking Jesse about the journey that brought him to where he is today.

Jesse: Before Drop in Blog, I did a lot of stuff. But I started building websites and running an agency and the scalability difference here is just, I mean, it’s one of those things where, you know, you mentioned it in a recent episode, the difference between making a living and making a killing. Well, as an agency owner, I made a living, a good living for a long time, but it kind of became golden handcuffs in the way that like, you know, I needed to start over to find something that I could make a killing with. And that’s where Drop in Blog finally came along. But it came a lot slower than it would have if I would have started with something that would have scaled a lot better.

Dan: Is that a regret that you have?

Jesse: I don’t think it’s a regret because I lived very well, in a lot of places for a long time, because as we’ll get to a little bit, you know, living Nomad life, I’ve been living out of the states for about 12-13 years. And, I left the states, I already had the agency, and I was already making over six figures. I just kind of like coasted and enjoyed that and started a bunch of side projects, but didn’t get that serious about it. The thing about agency work is – when somebody shows up and says, ‘Hey, would you want to do this project, it’s $15K’, and you say, ‘Well, yeah, that’s nice to have $15K in the bank, and then I can keep living my life’. But then, of course, then that puts you into doing a lot of work to get that done, and keeps you away from doing something that will actually scale. And scaling an agency is a nightmare. I know a lot of people that have agencies that have 150 employees and are doing three, four, or five million dollars a year, and it’s a nightmare to run. I never had any interest in doing that. So it was always like, ‘Well, I’m going to keep this at this level so that I can have sanity and still give good work. But then I need to work towards something else’. When Drop in Blog took off, we had four projects that we were working on. And then when that started jumping, then we sold all the other ones, to give us some runway and went for it.

Dan: So you had like a classic agency, where y’all basically did like web development and digital marketing for local businesses.

Jesse: We did have a little bit of a niche that was different from other people in that we did wholesale to other agencies. I was living in Madison, Wisconsin, I just went to all the other agencies there. And I said, ‘Hey, we have a better team, and I can develop faster and keep up with the technology better than your in house can. So why don’t you just outsource everything to me?’ So we had the agency, we’re making static sites. And then that’s where the idea came from. Because we had this demand, ‘Oh, we love the site. But we want to add a blog’. So then we had to add WordPress in its sub domain and create another theme and all this. And then so that’s where the idea like, oh, if we could just Drop in Blog into the existing platform, that would be great. And that was pending for a few years. And then we finally built it. And then we just used it for those clients, and it was making something like $2,000 a month or something. And it was just another one of our projects. And we didn’t really see how it could scale. Because if you look at the keywords that we were ranking for, there’s barely any traffic. And we thought, well, this probably can’t turn in anything. But hey, maybe someday, it’ll be 10 grand a month.

Dan: So in other words nobody was looking for a Drop in Blog before you built it.

Jesse: Right. We got an inquiry from somebody, awhite label person actually, that wanted a few accounts. And we were like, ‘Oh, ok’. Before that we were like we ran around like $2k a month for like a while. And then this was like an extra $4K. And one thing we noticed was that in a bunch of our signups, we were starting to get more signups on Drop in Blog, and we noticed that they were integrating, you know that they weren’t static sites, they were on these builders. ‘Oh, they’re using Weebly and they put our thing … and they’re using WebFlow and they put our thing … and oh, they’re using Leap’, and then it’s like, ‘Oh, whoa’, like, then all of a sudden, the aha moment hit that. Now we have someone to market to. So then we start looking at – well, turns out our product will actually work, or we can make it work with basically any platform. So then we started doing some research and we found about 50 platforms that we can target. And now we kind of look at their audiences and we go, ‘Oh, okay’. So now all of a sudden we got say maybe like $8k in MRR. And then at the same time, we were looking through the data and the signups and saw the potential and we were like,’Oh, this this is it like I can’t see the ceiling like we need to, you know, stop everything else and run’.

Dan: What you’ve done here is identified a moneyed problem. You were solving problems with money, and that money led you to product. I think that’s a really important lesson. Because when people just see, ‘Oh, here’s a guy with mid five figure MRR, he’s got a real slick software product’, as people who aim to either want to become entrepreneurs or want to transition to product that can look really intimidating. I’m wondering if you can kind of add some texture to that. Because, for me, it’s really inspiring to hear the story of how you got there, because it makes me think that I can duplicate what you’ve done.

Jesse: The lesson that I guess that is the takeaway is that we were actually solving a real pain point. And finding what that is – they needed a blog that went on the site, instead of you coming up with an idea like, ‘Oh, maybe people will think this is fun’. There’s so many SaaS products that are like 10 bucks a month that are some random add on that everyone could use, but no one really needs. And I think that trying to find an actual pain point, and ideally, something that’s going to add to their bottom line so then when the recession hits, you’re not the first thing that comes off of the list. I mean, as anyone who runs a company, right, we all are subscribed to a bunch of SaaS products for this and that and the other thing, right? Well, when money gets tight, the first thing you do is run through and you say, you know what, that A/B testing thing that I feel like I tested it, I used it, we made some nominal results. And you know, that’s 80 bucks a month, like we’re cutting that immediately.

Dan: But you’re like the plumbing of a business at this point.

Jesse: It’s a little more resilient, I guess we’ll say. Solve a problem that’s an actual problem, not a pretend problem. You know, I mean, not that conversions are not important, to use that example, or whatever, of course, but, you know, there’s things that you know, it’s like, You’re not leaving your email provider. It doesn’t have to be that big of a problem. But it has to be a problem. That’s an actual problem, not a pretend problem.

Dan: You mentioned this period, where you were just making a living and things were going really good. Did the fact that you didn’t arrive at product and scalability sooner have something to do with the quality of your lifestyle, or the fact that you were nomadic.

Jesse: I didn’t have a lot of motivation. That is really the honest part about it. I was making enough money that I had a really good life. When you have cash flow the pile doesn’t matter, you know, and it’s a lot easier to spend cash flow than it is to spend pile. Piles are scary. It’s nice to have a pile but piles are scary to spend. Cash flow is easy to spend. It’s really hard to get motivated to say, ‘Oh, starting this thing from zero, or whatever’, but the difference is, the advantage, I guess, that I had is that, you know, when I’m running an agency and building product, everyone else’s products for 10 years, I know how to build a product. I know how to manage a team, so that part was easy for me. Sure, I wish I would have hit this landmark. 10 years sooner, I feel like it would have been possible if I would have really focused, but, you know, having that much experience with team management and just building stuff paid off now. We now actually have a very stable company. I’m not worried about the quality of our back end. It’s not a house of cards. It’s something that, by having that experience, I was able to actually build something more solid, I guess,

Dan: As a founder of a company at this scale, what does your day to day look like? What is your actual input into the company,

Jesse: I found that my best focus in the company, or in life really, is I’m really good at zooming in. And I’m really good at zooming out. So I’m really good at vision, I’m really good at trying to figure out where the company is going to go and what are the big steps that we’re going to take. And then I’m also really good at jumping into the last detail of the thing to make sure that the UI and the drop down is not messed up on this thing, and can get that perfect. It’s the middle stuff that I’m not good at. So I try not to spend too much time there. So as I mentioned, I have two other co-founders, so one of my co-founders is operation head, she’s the one who’s a little bit more in with the team and kind of doing the middle stuff that I’m not as good at. And then my other co-founder is the technical co-founder, and he manages the back end, and then also the staff that’s involved with the programming and that kind of stuff. I’m kind of the ship captain. And so my focus is usually trying to make sure the ship is headed in the right direction.

Dan: It’s interesting that you have a technical co-founder, given you’re technical. And I was also interested that you just had an agency for a long time. And now your product I feel like that transition is, is one that so many people want to make, but they just never quite get there.

Jesse: It’s hard. It’s really hard.

Dan: Why?

Jesse: Because the money is too good.

Dan: It’s like, a really high high. You get paid a lot in agency work.

Jesse: Yeah. And you get the money today, right? Like, it’s right, you know, no one in my SaaS is offering me $15,000 today, right? It’s just not the case. It’s just not how it works, you know, they sign up for 50 bucks or 30 bucks or whatever, and so it’s this very slow, long, like grind, which is great, because it’s very stable and whatever, but it doesn’t have that rush. I mean, agency life is like, Oh, you hit a big contract, and this big chunk of cash hits the bank account. And you go out and have drinks and we’re doing a project for *insert large company name or you know … there’s that kind of rush to it. And it’s really hard to say, ‘Don’t go out and celebrate, let’s focus on working on this product that’s going to release in a year, and then we’ll slowly get some customers and then in a couple years after’, you know… 1000 day rule stuff, right? Who wants to do that when you can go make 500 bucks today.

Dan: So one of the theories on the show that we roll out often is if you feel like you, and that you’re wired to be a hustler, and an entrepreneur, that the easiest way to get that done and to create a sustainable nomadic income is to essentially start a agency or even a more focused productized service, do you believe that to be true?

Jesse: It’s definitely the easy way in, I think that the productized service is better than the regular agency, I love that that kind of came about. We never really transitioned to that, that kind of like, showed up a little bit after us. And we kind of did some things like that with some of our customers, since we were doing wholesale work for other agencies, we did have a very priced out, you know, ‘This is how much it is for the custom WordPress theme’. And ‘This is how much it is if you had a forum’, and ‘This is how much it is, if you skin out a Shopify store’, but it wasn’t truly productized like things are now. So I would definitely say that, if you’re gonna go with client work, that productised is the way to go. Because then you at least have a chance at scaling. The problem is, even that is really hard to scale. Even the people that we know that have really scaled productized, you’re still running an agency, like you can tell yourself, you’re not running an agency, but you’re still running an agency, there’s a lot of human capital involved, and it’s really still really hard to scale. It doesn’t become exponentially profitable, like products do. And so you still need to get that team and keep growing that team. And before you know it you’re managing 150 people, and that’s hard.

Dan: I’ll say a couple things about the productized thing in response to that. I think you’re spot on. One of the things is just the general opportunity of being a wholesale productized service for agencies like this is a real opportunity. It’s something that people are doing really well with sizable products. I thought your ‘Skin a Shopify site’ is a great example. It’s easy to identify agencies, because they’re trying to market themselves. So then you get in front of 100, a couple 100 agency owners, and you’re, ‘I’m the skin a Shopify site person, we have a whole system for that’, that’s an opportunity. The other thing I’m seeing is this, I know that there’s like really successful agencies out there, just like there’s really successful law firms and oil companies and stuff. But in the niches that I’ve seen, the people in this community, it feels like the agency owners that are doing really well. They’re talking about making multi six figures a year. And the productised service owners that are doing well, they’re talking about making seven figures a year. And then it’s like the people who build products, they’re the people that are talking about eight figure exits.

Jesse: Totally. I mean, the agency thing and the margins, the further you go up, the worse the margins get. We were able to keep good margins at, you know, running at low to mid six figures. You want to run mid seven figures through an agency, the margins go down, down.

Dan: You can have a pandemic or whatever. And it just kills your very fragile House of Cards, like how you’re gonna make the money. I’ve personally worked on a p&l that I contributed to where you’re talking about, like, a whole year’s worth of stressful sales calls, like million dollar clients, close to $4 million in revenue. And at the end of the day, a founder who’s no dummy, who’s very smart, who went to one of the top business schools in the country, is writing himself a check for $215,000.

Jesse: Totally. But the original question here was like, ‘Should you get started, should you do agency work? Should you start a productized service’? I would probably go back to the idea of – do anything. Whether be agency or anything that you have some skills in to cover your expenses, get your baseline covered as efficiently as possible and just stop there. That’s where we always get caught. It’s like, ‘Well, now that’s going pretty good. And maybe I should double down on that’. No, that’s probably not that, you know, now focus on the big thing, and, you know, suck it up and just live on that amount of money for a couple years. And work on the big idea. Again, I got stuck there for longer than I would have liked. I started about 20 years ago, doing this kind of stuff. I started making decent money about five years in. And it wasn’t until just a couple of years ago that I was able to flip over. So that’s a long time of being stuck in agency life. I was making a living, I wasn’t making a killing, that’s for sure.

Dan: Alright, I want to lay out the framework here, the inception moment for you to not be a normie and to be a digital nomad instead. And then I want to circle back to that. So what was the inspiration for you to go nomad, versus to go normie, so to speak?

Jesse : Well, there were kind of two chapters for me actually. I went expat before I went Nomad, before Nomad was a thing. So around 2008, I was living in Madison, Wisconsin, and was looking for a change of pace. I wanted to be in a bigger city around more interesting people and kind of what we talked about, community and life adventure and this kind of stuff. And at that point, I was kind of looking for other cities to move to. I had this location independent income that I created with the agency, and so started looking at are initially other cities in the States. So I was like, ‘Oh, I’m looking at Austin. I’m looking at Denver, you know’. I had been on a vacation to Panama City, Panama, a couple years earlier. And I was like, ‘Oh, man, I remember Panama. That was pretty cool. Like, I could probably live there’. And kind of went on another trip to like scout. And then that’s where that arbitrage hit me – oh, yeah, I can live like I’m living in Miami here. For the price that I was living in Madison. If I moved to Denver, or Austin, my lifestyle is gonna go down. And that was kind of it, it just kind of clicked.

And it actually took some time because I was living a more normal life, I owned a house. And so I sold the house, and I actually bought an apartment in Panama, and moved there and then set up like an expat life there, which was way better than my normal life in the States. I was doing the great things that we do as nomads, but there was like a fair expat scene there. So I had a lot of friends. It was the first time I had met other entrepreneurs that were really doing the kind of stuff that I was into and interested in, and people making products and software and that kind of stuff. Whereas in Madison like I had zero peer group, it was just very not a fit for me. And then when I got to Panama, that’s when it all kind of clicked and I met interesting people from all over the world that were doing interesting things. We were renting beach houses and renting boats and going to islands and doing stuff with people from all over the world that was very interesting. So that was kind of my first chapter. I lived there actually for quite a few years. I mean, officially, probably like eight years, but the last two years is kind of when I started nomading. Then I then I kind of started learning about the Nomad community, and started listening to the pod a little bit, and I actually went to a co living month. That’s where I kind of got exposed to people who were actually nomadic. When I moved to Panama, I looked for other people. This is 2008, so the ‘Four Hour Workweek’ wasn’t even written. I was already living in Panama when someone handed me the ‘Four Hour Workweek’, then it wasn’t until, man not that long ago, I think it was around 2014 or something.

Dan: That’s kind of long ago, at this point.

Jesse: I went to this co living month that someone randomly on Facebook was like, ‘This sounds like something you’d be into Jessie’, and I went to this co living month and met a bunch of people that were more in the Nomad community. I had been going to Chiang Mai and listening to the pod and and you know, working on their products, going to Bali and all this kind of stuff. I didn’t know anything about any of this stuff. Like I just kind of was living in a bubble working on my stuff. And then that’s kind of when it all changed because at that same moment, I was kind of getting bored with Panama. People were moving on to different things. And just kind of sick of being in the same place for so long. And then that’s kind of when I spent a couple years kind of in and out of Panama, floating around the world and said, ‘I’m definitely leaving Panama, put my place on Airbnb full time’ and moved to Thailand as the first like base. I think that was like 2016 or something like that.

So I kind of went opposite like a lot of people they like, go into Nomad life and then they slowly work their way kind of back into normie life. And I kind of started in normal life and slowly worked my way into super Nomad life. So when I first got to Thailand, I got a year lease in Chiang Mai, and had a nice place and kind of got my feet wet there and then travelled around the region, but then I realised I only spent six months in the apartment out of the year lease paying double rent, etc. So then after that lease was up, I just went Airbnb full time forever. And then through that, I kind of got sick of dealing with managing this apartment in Panama. So I sold that apartment to become that kind of asset and worry free, and then just being really agile and living full time Airbnb without having a real home.

Dan: I think it’s worth just in the American context, and then people who are, you know, they’re normies in Australia, or if they’re normies in Europe or whatever, they can paint it for their own context. We’re both Americans. One of the things I think it’s worthwhile pointing out like normie versus like Nomad versus expat is because the expense of being a normie if you want to live a reasonably middle class or upper middle class lifestyle that’s been afforded to you by your business is incredibly high, as is the price of nomadic. So you have to be quite wealthy to sustainably support both of them. And so that I do you think that there is this diametric quality to it. The idea of just having a high quality lifestyle in America, and then nomading in half the year. That’s like, we’re talking about a high level of income there. And so kind of my first question, that kind of my first question is the kind of lifestyle that you live full time, Airbnb, Nomad lifestyle, how much does it cost?

Jesse: The level of life that I live, I generally spend probably like $6-9,000 a month on, you know, everything.

Dan: So I’ve been spending that much here in America, maybe we could do a little bit of lifestyle comparison. I mean, what do you get for your $6-9,000 a month?

Jesse: You usually get a pretty nice apartment. As my income increases, that’s the first place that I spend more because working from home, we spend a lot of time in the house. So I continually scale up the apartment. You can live in Airbnb around the world for around $1,000 a month. And that was kind of my budget for a long time. But then as my income kind of grew a little bit then I started moving two to $3,000 a month and especially in some cities that are a bit more reasonably priced than what you’d see in the more expensive countries, you get quite quite a bit so I think that the apartment is the first thing.

Dan: As a rule of thumb, we were brainstorming. It depends on the city. But I think that, as a rule of thumb, living the Airbnb life, which I have my credentials as well, I’ve done this for years at a time. It costs about three to four times what the local rent would be.

Jesse: I would disagree. I say it’s about 2x the monthly Airbnb price, not the weekly. If you rent by the month, which usually then Airbnb will have a separate discount for that.

Dan: I think my apartment would be about $5000 a month on Airbnb. And I’m paying $18-1900. So that’s an American ratio. I’ve often said that to live like the Airbnb life in America, you kind of need like 4500 bucks a month to chuck at rent, if you want to live in a decent kind of place.

Jesse: Yeah. Let’s be clear, like what you’re getting for $4,500 a month in the states is nothing compared to what you get everywhere else.

Dan: Oh, you’re getting like a normal apartment.

Jesse: The other thing that I found talking about that ratio is that if you build relationships, and even just by staying a month or more, they’re not used to that, a lot of their pricing is built around people staying for a week or a weekend. So, when you rent for a month, or say you’re gonna rent for three months, you have some negotiating power there. When I was living in Manila, I was actually able to get down to the lease price at one place that I frequented. Just because they liked having me there. I think a lot of these Airbnb people, they get sick of dealing with the Airbnb. So what if you can offer them, you know, a solid booking for a few months, which they’re not used to having now that hassle becomes off their plate, you have a little bit of negotiating room there. But either way, I’d say 2X is what I would say is the average.

Dan: So let’s discuss some common objections to nomadism. What about this idea, like people say, like, nobody and takes a lot of energy to do travel plans and organise your stuff and all that?

Jesse: It is true that there is more planning involved. That said, depending on how often you move, at my peak, I was doing a month in each city. Most people find it more sustainable to do three months. So if you do three months in a city, that means you only have to book four places a year, that’s not a terrible amount of work. And the thing about Airbnb is, they’re actually kind of more serviced than a regular house or apartment would be in the fact that you basically have a built-in assistant on some level. You can ask them about things in the city. Or you can say like, you know, if there’s a problem with your internet, or with your water heater, they’re there to take care of that. If you own a place, there’s endless amounts of stuff you have to do, right? You got to clean the gutters and paint the house and mow the lawn, etc.

Dan: One of the things that shows up on my hypothetical line items for home ownership is you’re essentially buying yourself a part time job, you’re buying yourself a tax liability. You’re also like buying yourself visibility on where you sleep every night, and you’re projecting that to the whole world. There’s this idea that homeownership is sort of the end all be all and I think that you know, the nomadic movement challenges that in some important ways. There’s a lot of rote, boring and non value generating tasks. From a financial perspective, not from an emotional perspective, homeownership has a long heritage, and I respect that and all that. And a lot of people love doing that kind of stuff. But from a financial perspective, you’re right, you’re buying yourself a to do list. And so this brings me to the next objection, which is like, what do you say to people who are like, ‘I just want to have my own place and like my bookshelf and bed sheets, and I couldn’t possibly live the Airbnb lifestyle, because I really like to have my own place’.

Jesse: So there’s a couple kinds of ways to look at that. It depends on how particular you are with that stuff. So one thing I’ve noticed is – once you move up the scale a little bit, a lot of people who are living Nomad life are baselining, so it’s the cheapest, cheapest, cheapest, cheapest, cheapest. Well, once you have a little bit more money: when you rent a place on Airbnb for three $4,000 a month you get nice sheets and like, you get nice kitchen stuff, Yes, it’s not necessarily all your perfect stuff. But it’s generally pretty nice stuff.

Dan: It depends what you’re good at. And what your focus is, I’ve found that as I went up the price ladder in Airbnb that the hosts became good at real estate and decoration and buying stuff. And so like I would learn things coming to places as when I compared to my current apartment, which is much less … In fact, I was speaking with potential interior designers recently, because I realised that I couldn’t get my apartment to the level of the places I was staying at for $2500 a month or $3000 a month when I was living in foreign countries.

Jesse: I will say that there is something to be said about having your stuff or having it just like something that’s comfortable and normal that you know. The other step two way to solve that or to to beat that objection a little bit is return to some of the same apartments. So I do that in some of the cities that I like a lot, I have a couple apartments that I stay at regularly. I generally buy stuff for the apartments too, because I’m staying there for a while. So that’s the other thing, a lot of people, they just think, Oh, well, man, this place is great, but they just don’t have a good knife. My life sucks’. It’s like, ‘Well, go spend $15 on a nice kitchen knife’. I’ll do that often, you just spend a couple $100 on little things around the apartment that are the things that you want, that would make it better. And then when you come back, those things are probably going to be there. The hosts are very appreciative that you added some nice touches to their apartment. And then when you come back then they have a nice knife or whatever.

Dan: It’s interestingJesse like, you know, part of it is like this deprogramming of like, these were genuinely large problems 20 years ago, when we got started our careers. And Airbnb is just like, come along and sort of evaporated them, you know, in the same way that Uber has done it for car ownership in some metropolitan areas. I mean, it is really fascinating to kind of see the ground shift within our underneath our feet. And that’s why I think it’s cool to talk to you as an edge case, one of the things you brought up earlier.

I want you to vamp on this idea a little bit like, okay, so you live in Madison, Wisconsin, it’s famous for having a really good university, smart people live there. And you’re like, ‘I had no peer group’. And then you move to Panama, which isn’t as nice as Madison by a lot of standards, you know, and all of a sudden, you’re describing like, meeting people who are building products. And this has been my experience. And honestly, if I’m being honest, like I have a great network here in Austin, Texas, but I still find myself around like normal people all the time. Describe like, what this x pattern Nomad, like kind of community, what is it? How does it happen? Why are we attracted to it?

Jesse: It’s pretty simple, it’s a great filter. If you had the foresight, and just plain the balls to leave your country and go live in another country for really any amount of time. Right there that’s a huge filter. You just think outside the box, if your brain isn’t just like, ‘Well, after I make more money, I’ll just buy a bigger house in the next neighbourhood’. That’s a big difference to, ‘I guess I moved to Panama because it seems interesting’. All the other people who had that same thought process, they felt the same way. And so then like, instantly, you just have this peer group of people that are so much closer to you, and they’re also working on online and they have some,

Dan: As this has gotten popularised, though, isn’t that filter becoming less compelling? What’s happening to that filter?

Jesse: Yes, and no. You’ll see this in the super level one hotspots like Chiang Mai for example.

Dan: What are the level one hotspots?

Jess:I think Chiang Mai is number one for sure. Bali, there’s Medellin. I think Playa Del Carmen these days has bubbled up. Saigon as well. Basically places that afford a great life and are inexpensive.

Dan: There are some European ones.

Jesse: The Canary Islands I can’t think of the town right now. And then also Lisbon.

Dan: You’ve got some Eastern European cities too.

Jesse: Georgia.

Dan: So why haven’t we mentioned an American or Canadian city?

Jesse: Number one is that they’re expensive. The value that you get for your money, it’s just not there. You can’t have a good apartment for $1,000 a month anywhere in North America.

Dan: This is like something that I just really wanted to underline on the podcast because I’ve been living here now for a year and a half. And I make a good income. But it is expensive and time intensive. So I think it’s me reflecting on the value that the nomadic lifestyle gave me and, and like a lot of the things that I took for granted in the nomadic lifestyle, like networking with highly filtered people, those filters here in America take time to implement and to execute.

Jesse: People are less open as to meeting people in the States because they kind of have their normal life.

Dan: So these aren’t profound truth of the universe kinds of things. But it’s the difference between making $3,000 a month and $10,000 a month. It’s probably like an interesting geopolitical conversation we had about relative wealth, and how national economies and currencies work together, but for whatever reason, there are certain things in North America that are expensive, and there’s certain things that are really, really cheap. You know, like, if you want to, like IKEA out your house, like that’s going to be maybe potentially cheaper in North America than it would be in Europe or Asia, certainly. But if you want to have a great apartment, spend a bunch of time with friends, and not do any lifestyle overhead tasks. That kind of thing is really expensive.

Jesse: I think this is the thing that gets missed when people say, ‘Oh, it’s cheap to live there. And so that’s why you only move to Chiang Mai, so you can live for $1,000 a month’. But this thing scales a bit like, one thing that you’ll find in America, anywhere that’s expensive, in Europe as well is like all the personal life admin that you have to do just to live. And you don’t have to do that anywhere else. So how much time do you spend a week, washing the dishes, cleaning your house, doing your laundry, running errands, all this stuff, that adds up and it’s there forever.

I’d love to find the clip, it was a long time ago, I remember when I was living in Panama. And at the time, since I was there full time, I had a full time maid that would come in every day and clean and cook and this kind of stuff. It’s very common, basically everywhere else in the world. And I remember watching a clip from Timothy Ferriss, and I don’t know what year this was, it was a long time ago. And he was talking, you know, because he was like, the God of our movement, right and and everyone was like, following what he did, but then he moved back to San Francisco and went back to like, living like VC life is very confusing. But what I thought was funny as he was was at the time when he was starting to work on I think he was starting to work on ‘Four Hour Body’ and, he was he was at a video about how his Morning Routine is and how he’s like, you know, hacking things and, and he was he made some scrambled eggs with … he put some eggs and some salsa in a Tupperware and cooked it in the microwave, and then ate it. And then he talked about how this is so optimised so he can just rinse that out. And it’s only two ingredients, but it’s tasty and it’s healthy. And I thought this was like the dream, this was the lifestyle design that you put on your, your dream line was that like, you can finally make it and have the best selling book about how to live our lifestyle so that you can make eggs in a Tupperware in San Francisco, meanwhile, my maid is like bringing me huevos rancheros and a fresh latte that she like, made for me at a set time when I like arrived in my office. What is going on here? I’m so confused about the life that you designed for us, you know?

Dan: What about the people who say, especially like, during COVID, there was a lot of kind of ‘a return to basic values movement’ in the community, I think. Because, you know, globalisation and the access that the middle class has to it is such a new thing, we’re kind of on this high with it, you know, I’m gonna go here, I’m gonna go there. And a lot of people sort of return home and they say, ‘I lived that it’s not for me’, you know,’ I couldn’t sustain relationships’. Let’s focus on the relationship part. People say, ‘How can you really have friends, if you’re moving around all the time’?

Jesse: It’s a valid thing, I think that one thing you’ll find is, first of all, when you hang out with nomads, you’ll tend to find that they’re moving around. And once you do it for a while, you start to meet enough people that there’s usually somebody in the city that you’re in, because we kind of tend to circulate through a number of hotspots and places that you tend to like. So a lot of times, you show up in Mexico City, and then you kind of check around in the Nomad or the expat Facebook group and kind of see who’s in town or this kind of stuff, you know. But when you’re starting, you can use a hobby, or some other thing to meet local people. And that’s generally the best way because then you can start to make local friends in those cities. And then when you come back to those cities next time, you already have some friends there. And then there’s some kind of excitement about, ‘I haven’t seen him for eight months, like, you know, what have you been up to?’ And you actually have stuff to talk about, instead of the same guy, you had beers with every week for 20 years? So yeah, you got to brew friends. It takes work, you know, you want to go to different meetups of your interests or other things, and you can meet local people and brew those relationships. But then yeah, you can kind of keep those going. And then when you come back to those places, then you start to have friends in those cities.

Dan: It’s interesting because I’m on the Jersey Turnpike a couple weeks ago, I’m hearing guys that are 70 years old talk about their their plan to do weather arbitrage, financial arbitrage, you know, down in Florida, they have friends that they look forward to my folks used to go to the Jersey Shore during the summer, they knew people down there. And in some ways, what’s happened with globalisation, and the access that the middle classes folks, like, I’ll call us middle class, like we have sort of access now to this amazing sort of global palette for the same thought exercise. And so part of me was like, ‘Am I taking crazy pills here? Because like, I’m, I’m spending the winter in Thailand’ or no, like Thailand, for me is like Florida was for the previous generation, all the same arguments can essentially be made. And it’s more financially viable for me to do it now because the quality of my income is location indecent.

Jesse: Not to mention life is way better in Thailand than it is in Florida. It’s not just about the money, it’s a good life in a lot of these places. And we’re so trapped in this bubble of like, ‘Well, should I move to Austin, or should I move to Miami?’ There are other options.

Dan: Let’s talk about the tech maximalists. I have a buddy, Noah Kagan, who would listen to this. And he thinks it’s interesting, nomading and all that stuff. But what he would say is, ‘Why don’t you just make enough money to live in the city you want to live in? Just move to San Francisco so what if you have to make hundreds of 1000s of dollars a year? Just do that, you’re smart. You’re in tech, go do that’.

Jesse: Because I don’t really find the US cities attractive like that. There’s something interesting about being in a culture that’s not your own. You can learn a language, you can walk down the street and see a food vendor that sells something that you’ve never seen before. And for me that just doesn’t get old. Living in San Francisco, and listening to VC guys talk about their great idea and then watching someone shit on the sidewalk, that’s not my dream life. I don’t find it great. The weather’s not great. I don’t think these utopias in the States are as utopian as people think they are, after being in other places. It also depends on what you find interesting. Talking about Noah’s argument. He likes living in Austin, and he likes the scene there’. Also maybe his status there. I think that that could have something to do with it. I kind of like the anonymity of living in different places, and I find seeing the different cultures around all the time I find that interesting. And if you don’t think that’s interesting then yeah, just move to Austin.

Dan: I just love thinking about this, because there is a big part of me that’s often asking myself, ‘Am I taking crazy pills?’ And I think back to the first time I stepped foot in Mexico City, it was the first foreign place I’d ever been. And it blew my mind. It was so much fun. And I kind of feel like you, it doesn’t really get old. It’s tempting to psychoanalyse yourself and say, ‘Is something wrong with me that I want to do something different than the mainstream or whatever?’ Do you ever think about that? Is there some sort of broken quality to somebody who wants to live abroad and not in their home culture?

Jesse: I’ve mentioned this to you before, but I feel the longer that you have the exact same routine and the exact place and do the exact same thing, your life just kind of evaporates. If you’re in the same house, in the same routine, in the same desk, in the same friends, in the same everything for five years, it’s the same as if you did it for one year, or 10 years. And then you’re just like, ‘Well, what happened in my life?’ I feel like the amount of time that I lived in Madison, for example, I couldn’t really tell you off the top of my head how long that was, because it all felt like one moment sort of. So I feel like you kind of hack life a little bit by getting to know different locations, because your brain sort of resets and everything’s sort of new and interesting. You’re like, ‘Oh, wow, these guys have chicken skewers on the street, that’s interesting’. And, ‘These people talk this language, or they wear this kind of clothes or whatever, that’s your brain kind of notices all that stuff’.

Dan: It’s like the two sides of the sword. I compare the last year where I had a routine, the same place. It felt less dense, like I did less things, whereas I think it would take me days to catalogue one year with a more nomadic theme. Because you just have so many more interactions. I even feel myself slipping back into that thing because I’m on such a schedule, and I have such a routine here. Meeting new people is much more of a liability for me here than it is when I’m away.

Jesse: You don’t want to meet people and you’re the one who wants to meet people. Whereas if you were in Mexico City tomorrow, and you’re like, oh, like you meet chatting with some dude at the coffee shop, like, ‘Hey, what are you up to?’ Like, ‘Hey, maybe we should get lunch tomorrow?” You’re in Austin.‘Dude, I don’t wanna have lunch with anyone. I need to focus on my routine’.

Dan: It’s pretty interesting to have that tool at our disposal. And I think it’s why I wanted to speak with you here today, Jesse, just to get a sense for – as travel becomes an option for a lot more people, it’s not an either or thing. You don’t have to be a nomad or a normie. So many people have gotten themselves to a place where you can basically have whatever you want to design for yourself. I think it’s really exciting. Do you have parting shots you want to offer to folks listening?

Jesse: To kind of recap what you were just saying there or go a little deeper, you know, you can, you can build your own path, right? If you want that routine and that house in your home country, and that’s fine too, and kind of on Noah’s point, you just earn more money. And then you can have that, and you can go to Mexico City for two months a year, and Chiang Mai for two months a year. If you want. There are a lot of ways that you can build this puzzle. And you know, it doesn’t have to be my way, and my way may change and your way may change. And that’s okay. Money solves most problems. And you know, there’s a lot of interesting ways to live life. And it’s gotten a lot easier than it used to be with all of the resources that are available. So you just need to kind of open your mind up a little bit.

Dan: I don’t think it’s an unsubtle thing to say that money solves all these problems. And that’s why the financial puzzle was so intriguing to me. I remember part of what was so cool about nomadism for me is that I got to meet a lot of wealthy people. Basically, I was blocked out of all those conversations in America, but somehow I just found myself at the table all the time abroad. And one of the things I realised about wealthy people that were even entrenched in their home country, is that they basically lived like nomads. The nomadic caricature is of the baselining ‘selling a course online’ person, but when you meet, like hyper wealthy people that have 1000 employees, and they run a global company, they are going to the F1 race here, and then they’re spending two months with them in their house here. And then they’re going to that thing over there. They fundamentally adopt what is a digital nomad life.

Jesse: They live all over the place. And I think that’s the thing that gets missed. I guess part of the point we’re trying to make is that the lifestyle does scale. And it gets better and more interesting. So it’s like, yeah, you can live in Chiang Mai and get started for $1,000 a month. And that’s great. And you should do that and get your business started. But once you start making $5,10, 20, 50,000 a month, this lifestyle scales great. There’s amazing places that you can live all over the world. And then you can live in any of those cities, you can live anywhere you want, anytime do amazing things. And you know, the money solves all of that stuff.

Dan: Jesse Schoberg Thanks so much for coming by the show.

Jesse: Thanks for having me man.

Dan: Big shout out to my guy Jesse Jesse Schoberg of Drop In Blog dot com. Check them out on Twitter at Jesse Schoberg. We got off the phone and Jesse and I were texting back and forth, producer Jane said we could have really dug deep on things like lifestyle ladder on percentages of costs in different regions and how it plays out hypothetically, in different businesses. And honestly, I feel like we could do a multi multi part series on that. If that’s something you want? Email us, let us know about that. What specifically do you want to hear more about? These topics are on the tip of the tongue for so many of us in the location independent community who have been locked down for so long, even though our organisations are, by and large, remote first and completely international. It’s been a really, really interesting time looking forward to just a little bit of normalcy. It’s been interesting to sort of shelve a lot of these questions for the past year and a half or so. And now to begin to revisit the opportunities and sort of the new context. Whether or not things return to the normal we once had this question of internationalisation of lifestyle and doing so with your business as well are absolutely going to be critical, strategic advantages in the future. Also just a lot of fun. So hope you enjoyed this one. Let us know what you’d like to hear us talk about on this topic in the future. We’d love Love, love to do another one. This is like total nerd out for us. Hope you enjoyed it, too. All right. That’s it for this week that next Thursday morning.