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Ep. 271: How This Developer Created A Freedom Lifestyle with Jesse Schoberg

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In this episode, I speak with Jesse who is a developer who has been living around the world for more than a decade.

He has recently sold his other projects and is now a co-founder of DropInBlog where he focuses his time as CEO.

Listen on to find out how Jesse has been able to live a freedom lifestyle as a developer and online CEO.


Listen Below:


Ep. 270: How This Travel Writer Designs Her Life Around Freedom and Helps Others Do the Same with Rosie Bell
Ep. 269: How This Former Chef Became A Remote Serial Entrepreneur with Jaiden Vu
Ep. 268: How This Bougie Backpacker Travels the World as a Remote Freelancer with Leah Arao




Hey everyone! Thank you so much for being here. 

I am really excited to speak with my guest today. I’m here with Jesse. 

Hi Jessie. How are you? 


Good, how are you doing?


I am wonderful. Thank you so much for being here with us.

Can you tell us about you and why you live an offbeat life?


Sure, my name is Jesse Schoberg, I founded a company called Drop In Blog and I live an offbeat life because I couldn’t see another way. 


Wow, so you mentioned that you have a company called Drop In Blog, what is that? 

What does that entail? 



Drop In Blog is a software product that basically just allows people to put a blog on any website that wasn’t built in WordPress. 

So, let’s say, for example, you built your site in Shopify or Webflow, for Kartra, or Teachable or Thinkific, or any of these types of platforms. These no code builder platforms, you can use Drop In Blog to add a blog to that software and it actually drops in to the existing platform. 

So, normally if you had built your side and one of those other things and you wanted to start blogging, you would essentially have to install WordPress on a subdomain or a folder and then you’re managing two systems and it’s kind of a mess. 

So, we kind of basically can think of it as like a plug-in for all of those systems that allows you to have a very robust content marketing system. No matter what they offer whether they have something available or nothing at all, then we can be the block solution for you. 


That is a really great idea and super efficient for a lot of people who do need it. 

How did you come up with that idea? How did this all get started? 


Well, many years ago I used to have an agency and we were just doing web development. So we were building static sites, just coding by hand. And then we had some very light CMS that would allow people to update those sites, and this is kind of before even WordPress became the big, big thing for building all of the sites and so people loved what we were building for them. But then, as their businesses grew and things progressed, then they got to a point where they wanted to do some content marketing. 

So, then they would ask, “hey, can you add a blog?”, and we didn’t have a solution. So then we started re-theming WordPress to match this site that we already built them and putting it in a subdomain or something like this. And then now, they’re running two systems and the whole reason that they went with the static site in the first place is because they didn’t want to deal with WordPress. And so, we kind of built it out of that. And then we thought, “What if there was just a blog we could just drop into these static sites that people could just have the blog part instead of this whole robust site building system that WordPress is.

And so, that’s where the idea started. And then after that was kind of marinating for a couple of years, then we eventually decided to build it out for our clients and then we did and then it was kind of just kicking along as side project for a while, just for our clients. Like that was kind of it and then it wasn’t until even a few years after that, that we noticed all these people that were using all these no code builders that kind of hit the world by storm, started using our product. 

And that’s when we saw, “well, this is going to be a big deal”, and we had a few other side projects and the agency. And we sold and wound down all of those. And then we went full in on Drop In Blog.


That is definitely a journey that you’ve been through and I’m sure you’ve learned a ton of that, and it seems like, Jesse, that you are somewhat of a serial entrepreneur. 

Is that correct? Or am I just assuming?


Well, I’m going to say I’m a recovering serial entrepreneur, because as one of my business partners likes to say that, like, I’m not allowed to start new projects. 

So, now that we have, now that we have the one that’s actually the, the winner, the big winner, it’s no more no more side projects until it gets big enough that we exit or something like that. 

So, but, yes. Yes, lifelong, serial entrepreneur, many, many different ventures from when I was a little kid, all the way up until now. But yes, now, I only have one project and that’s, those are the rules. 


Your partners are like, “that’s enough, Jesse, we can’t take on any more right now. We need to focus on this.”, but that is pretty amazing. 

When you have that type of mindset, when you can just go and create these ideas and make them into a reality and obviously you’ve always been like that because you mentioned being a kid and doing this. Now, what were you doing? Like, did you go to school and then you thought up of these ideas? or you went to school for something else and then just pivoted and now you have all of these different types of business.


No, I actually didn’t go to college or university. I kind of started, I mean, ever since I was a kid, but I mean, the real hustle kind of started when I was in high school and we were doing, like, all kinds of weird stuff, like we were selling Thigh Masters on eBay. Like flipping video game consoles. T-shirt company, jean company, all kinds of stuff. 

And then, after I got out of high school. Then, I kind of got interested in web design stuff and kind of started learning about coding and that kind of thing. And so that’s when I started building websites and started falling down the sort of internet rabbit hole around, yeah, just like a year out of high school so, I didn’t actually even consider going to college. 

I just felt like it’d be a waste of time, there’s just like too many opportunities, so, I kind of felt like that would just put me in debt and four years behind on whatever businesses I was going to work on so, it didn’t really cross my mind to go to college.


Yeah, so as you can all tell, Jesse is very smart, because he didn’t go into debt going to school. instead, he started all of his businesses and also I do have to mention, Jesse, that, you know, for most of us in high school, we had no idea what making money was like, I mean, we all had jobs, right? But it wasn’t like what you were doing, starting these online businesses, online ventures. But, with you, you’re like, “I’m going to sell this online. I’m going to have this and that”.

Did you have that entrepreneurial mindset? Because maybe you had family members, who are doing that or you just found this out yourself? 

How did that even happen? Because most high school students don’t even think about those things, right? Like, we’re still juveniles at that age, not thinking about, like, “what can we do online to make a profit or make income?”.


Yeah, honestly I’m not super sure. I mean, my parents were entrepreneurs, they owned a retail men’s wear store in the small town, where I grew up. So, you know that they think they were business owners and they were running that business themselves and in this retail environment and I did work in their store, and kind of got to see how some of that stuff worked, but it wasn’t really, you know, they weren’t like, serial entrepreneurs trying to do all this different stuff.

It was just, you know, they were working for themselves. So, I did see that influence for sure. 

But you know, honestly, I don’t know. I guess I always just kind of, I like the chase of it. Like, my brain would always just see arbitrageurs and kind of like the rush of the hustle of this kind of stuff. 

And I always kind of saw the, the key of money and freedom kind of going together, where it’s like, you see, like, “oh, well, if you had some money then you could solve this problem or you could live where you wanted or you could, you know, go on vacation, or you could have the object that you want.”, or whatever, everything kind of, you know, when money is used as a tool, it’s very powerful, right? So, I kind of, I don’t know, I always saw that being very obvious and I thought, “well, even if I don’t know exactly what I want to do, I know that if I have some cash from any cash flow of anything, I’m doing, that will make my life better”, whatever the thing is that I decide to do. When I decide, “oh, I want to get into tennis or something.”, it’s like, “well if I can afford a tennis coach and a tennis racket”, and I don’t know if membership or something, I don’t know, it’s just a random idea, right? But the point is, you have to be ready by like, having some income, it always seemed like that would be the smartest way to go about it. 


And yeah, one of the things that I hear this word that I hear a lot from from people who are location independent, who are entrepreneurs, who are remote workers, is that idea of freedom. 

That was one of the first things that a lot of us found really appealing, is this idea of freedom, not being tied down to something that we didn’t want, having that freedom to, like, you mentioned Jesse, live where we want, purchase what we want, enjoy the life that we want. 

So, that is definitely one of the things that we all have in common and also I wanted to talk to you about, you know, because I’ve seen this a lot especially on social media and some of the people that I talked about the idea of passion, you know, doing something that you’re passionate about versus something that you’re doing and you’re following the money so you can create freedom. 

How do you feel about that? How do you align yourself with that? Is it one or the other or both? 


I think passion is a great idea, after you make enough money to do the basic things that you want.

I think that a lot of people fall into the trap of saying, like, “oh well I’m really into playing guitar so I’m going to start like a guitar lesson course”, or “I’m going to, I’m going to sell guitar strings on Amazon”, or something, you know? And just because you like it doesn’t necessarily mean it’s a good idea. Doesn’t mean that it’s a profitable niche. It doesn’t mean that there is a big opportunity, it doesn’t mean that it’s not overcrowded. 

Usually, actually, that’s a problem with most passions is that a lot of other people are passionate about those things because they’re fun, whatever it is, right? Say, a guitar for example, right? A lot of people like to play a guitar so that means a lot of people had that same idea that said, “oh well I love guitar, so, I’m going to make my guitar lesson course on…”, you know, whatever, yeah, you and 10 million other people. 

So, I feel like the trap of the passion is that a lot of, whatever people are passionate about there’s probably a lot of other people that are passionate about it as well. So, it’s a crowded market, right? So, I generally tend to say, depending on your goals, but I mean, most people that I talk to, that are trying to become location independent. You know, they have sort of like a baseline amount of income that will allow that to happen. So, if you’re interested in living outside of expensive countries, you can do that for fairly cheaply, say, 1 to $3,000 a month, you can live in a lot of places in the world. So, a lot of times I kind of say, “just do literally anything, any type of coaching, consulting, development, selling of products, like, literally anything, you can figure out how to do location independently, that you can make that base amount of income so that you can live your life and not have to have a job”, and, you know, then maybe consider things that are your maybe more passionate about and that kind of thing. And I think it just kind of depends on if your goal is to be just rich from earning money from doing these things. Or, if you know, kind of want to combine that and say, “well if I’m spending a lot of time on this work, then I want it to be something that I’m super into”, you know, and there’s a balance there but I generally say to start off, do not do anything based on your passion, do it based on if you think that it’s going to actually be a successful business.


Yeah, I absolutely agree with that and I think being realistic is the thought of something that’s bad, right? Because, “oh, well, you’re telling me I’m not supposed to do something that I enjoy.”. You can actually enjoy something that maybe you’re not passionate about and actually, it may be better because you’re not emotionally involved in it. 

And, you know, I’m sure you’ve gone through this too, Jesse, and definitely, I have where I did go after something that I was passionate about. And that’s exactly what happened. No money came because I wasn’t really thinking about the financial aspect of it, and guess what happened? It went nowhere. 

But, when you find something that you’re maybe interested in, obviously, you don’t want to do something that you absolutely hate. It can really align with what you’re talking about, Jesse, which is your lifestyle, what type of lifestyle that you want. There’s definitely people who want a lot of money, because they just want to build wealth, and that’s a completely different lifestyle than somebody who just wants a freedom lifestyle, who wants location Independence and wants a lot of their freedom to be there on their own terms as well. 


The other thing I’ll say on that topic that I find interesting as well. First of all, whatever it is your passionate about, if you can figure out a way to actually make money in any way, this will give you time to enjoy that passion or do that passion as a side project, right? If you can figure out how to make 5, $10,000 a month, doing some other hustle that isn’t your passion, that’s going to create this freedom in time-space for you, to either just enjoy that thing that you’re passionate about or build a side business about that. 

So, that’s one way to look at it. The other thing that I’ll mention that a few people have talked about, which I think is interesting, is that if you do your business as your passion, you might ruin your passion,




because then, it becomes your job, you know?If you look at the Hot Ones Guy, he hates chicken wings now and it’s like someone asked him like, “oh, do you ever just like, you know, when you’re in a new town, do you just like go look for the best chicken wing joint and he’s like, “Absolutely not! Like, I literally only eat chicken wings when I’m filming an episode”. 

And, yes, because he ruined his own passion because that’s the thing that he did, right? So, imagine that you’re into guitar for example, and then you spend all your time making guitar courses, and then you spend up all this time doing tech support for people who took your course and trying to teach them stuff, and you kind of forget that, why you like playing guitar was because you like to create music and you enjoy that, not that you like teaching people how to tune your guitar or what, you know, these kind of things. 

So, that’s what I thought, an interesting kind of comment and note about the concept of making your work, your passion, is that you might actually ruin it for yourself.


Yeah, I’ve definitely heard that, and it is, it is true, you know, and there’s definitely exceptions to the rule for the most part, if you are doing it 24/7 and you’re not just doing the fun part because that’s the thing, right? When you’re doing your passion and you make it into a business or a job, you have to do the other stuff,




that is not as much fun and you’re probably going to do a lot less of the fun stuff and more of the non-fun stuff. So, it becomes pretty similar to just doing a job that you can tolerate or you enjoy maybe but you’re not super passionate about and yeah, I love that, Jesse.

Do it on the side. Build that, do it for fun. Maybe delegate the stuff that you don’t want to do, because you can afford that, because you do have this other job and you just do the fun part of it. But if you just do it solely and you’re just trying to make money from it, then all the bad stuff is going to happen too.


The other thing that’s cool about doing it as a side project later, if it’s something that you’re passionate about, for example, is that, you know, then it doesn’t have to be profitable. So, you can like, use some of the tools that you’ve learned from your other business and it could still be a business but it doesn’t, the goal doesn’t have to be to like make tons of money, you know? So say you’re into photography and you want to start a side project of your photos or something, you know? It’s like, “well look it, now you learned social media and some other marketing advertising stuff from your other hustle. You could apply that to that and maybe hopefully you have some money coming in that you could even dump in some advertising in some of this marketing skills into this new side project. But, since it doesn’t actually have to make money because it’s not, you’re not doing it for a living, you don’t have to make any artistic compromises and it doesn’t even ever have to make money, it can just be cool and fun for you. 

So, I mean, that’s kind of the dream of passions, right? That you can just do this stuff as you said that you actually want to do. So, there’s a lot of ways to cut that.


Yeah, absolutely. 

And speaking of doing what you love, being freedom lifestyle type of thing that you’re doing right now, Jessie, because before we did this interview before we hit record, I asked you where you were and you’re in Asia right now, right? 


That’s correct, that’s correct. I’m currently in Bangkok, Thailand, which is definitely one of my favorite places. 


So, tell us about this because you are obviously location-independent you have this online business. 

How did you end up in Bangkok?


Well, I was in New York last week, and then I got on a plane and came here. That was, that’s pretty much the whole story. 

I mean, it’s like, Asia has always been a hotspot for location independent people, particularly Vietnam, Thailand, Philippines, Taiwan, these are, you know, always been hot spots for nomads and location independent people. 

So, I’ve been coming to Asia for about 7 years I guess. And so you know, there’s a lot to explore here. There’s lots of great lifestyle food, all that kind of stuff. So, I like to base over here, a lot. 

Also, Latin America has a lot of great things to offer, so I’ve based there quite a bit as well. Yeah, just kind of depends on what you’re into and in that kind of stuff. 

So, but I’ve always been a big fan of Asia, I spend quite a bit of time over here in Thailand and other places in Southeast Asia. 


Did you stay there for a long period of time? Or are you somebody who likes to just stay there for a week or two and then move on to a different country? Or are you more like a long-term traveler type of person?


Yeah, I’ve been doing this for a long time. So, I kind of found that the perfect amount for me and I always say everyone’s, my amount is, is a little bit different on this kind of stuff, and I do think it’s a mistake that a lot of people when they first start nomading, that they travel around like a backpacker and they just do, you know, are in a new city, every three days and they’re touristing the whole time and it’s really hard to build a business when you’re doing that. 

So, a lot of people end up failing and returning back to zero because you know, “oh they started this business, they were making a grand or two a month. They decided to come to Chiang Mai or wherever and then they end up partying and traveling and touristing around all the time and then lose focus on the business. And so there’s a balance there, you know? 

But what I found is that I think the perfect amount of time in a place is generally 1 to 3 months. Anything less than a month, I find that it’s too hard to get settled and get work done and get any routine. 

And then when I start to get past three months, then it starts to feel too routine and gets a little bit boring and it’s kind of time to jump to a new spot. 

Now, what a way to hack that as well as if you return to the same places fairly regularly, you can slide right into routine very quickly. So, you know, a lot of cities that have become my favorite spots, I go to very regularly and so, then it went out when I show up. It’s not that it’s not like, I’m starting from zero and I don’t know anything about the neighborhoods or the culture or just kind of stuff. 

So, anyway, as 1 to 3 months is kind of the magic number for me. 


I agree with that, because I’m also a more of a slow traveler and you know, in my early twenties especially, I was very much like that backpacker too that you had mentioned. I think we all go through that motion of like, trying to check off our bucket list and putting as much countries as we can, right? 

And then as you get older you’re like, “oh my gosh! This is tiring. I don’t want to be in a hostel with like bunk beds anymore and I want to see things so much more, better, so much more slower and it gets tiring too when you’re working and traveling at the same time and you had mentioned that Jesse, like you can’t really get enough work done or at least enough for you to make it very sustainable for yourself so that you know,1 to 3 month period is definitely a good amount, so that you can see as much as you want, but also do as much as you can, if you are working remotely or building a business. 

So, you mentioned, Jesse, that you do have favorite spots that you liked to frequent that you like to go back to, what makes a spot, or a country, or city, a good one for you, like a favorite? 

What would take off your list of favorite places?


I personally like cities more. I’m into big cities. So, I do spend a lot of time in Bangkok, in Mexico City. Like, so I mentioned, I was recently in New York for a month. Sometimes, I go to L.A., Taipei sometimes, Ho Chi Minh City, Vietnam. These, like major, are the major hubs for me, you know, that’s always good. 

And then if I want to go somewhere a little more low-key, I like to do Bali or Chiang Mai or some of the islands in the south of Thailand. 

So, those are kind of the best spots for me and I mean for everyone, these things are different. I think having a community wherever you go is generally something that people like and having people around and whether that’s people that are also doing online stuff like us, which is always helpful and inspiring and that kind of stuff, most of those places I mentioned do have a pretty strong community. 

The other thing could be just if you’ve been going to a place for a while, I like to try to make local friends who are not also location independent travelers, you know? So, that when you actually go to the place that you have friends to hang out with that are kind of there all the time versus when you’re always connecting with other nomad type people, the good news is you could show up in any city and there could be any of these people could be there. So that’s really fun and exciting to like meet people in four different countries, you know, that’s really cool, but then you know, sometimes you get to a place and there’s no one you know there and then that can be a bit isolating. 

So, it’s spinning, putting in some effort to kind of join some sort of local communities a little bit and try to make some local friends in cities is really fulfilling, also will help you connect with the city, and the culture of the place a lot more as well.


What do you do when you go to a new place and you don’t know anybody there? Because I know it can be really nerve wracking, especially for people who are introverts, right? Maybe great they’re on their own but to have that community that you’re talking about, Jesse, it can be really tough for somebody. I mean, I guess even if you’re an extrovert too. Just going up to somebody, making conversations, do you do anything to make that easier for yourself? 


Yeah, I mean, there’s a lot of like hacks that you can do. I think, like, Facebook groups are really helpful. So, if you have any interests, a lot of times there’ll be a Facebook group for any of these cities around a specific interest, so of course, there’s going to be expat groups of any city. So, yeah, you can join like expats in Mexico City. Expats in Playa del Carmen or whatever. 

And then that’ll give you kind of like a base point for a bunch of other people who are sort of in your same boat and then they’ll be sort of events and this kind of stuff that you can kind of pull yourself into or if you want to, you can say, “hey, I’m new to town, does anyone want to meet for a drink or something?”. You know, that can work well.

The other thing, if you have any other, like, cultural interest, or whatever, there’s usually groups of, like one, like you being Filipina, for example, my fiance also a Filipina, so when we’re traveling around, she’ll join like the Filipinos in whatever country group and then, you know, then you it opens you up to this whole other group of people that are there for a different reason than we are usually. And so then that can just, you know, you have some cultural ties, but then also it’s just a new group of people doing different things. It could also be some sort of sport or activity that you’re into, doing that kind of saying, another one that I’ve used before is the couch surfing community. So, I don’t know if you’ve ever done couch surfing before, even if you don’t stay at people’s houses, like the original purpose of couch surfing, the couch surfing community, they have meetups in most cities around the world. So, that’s kind of an interesting way to meet interesting, open-minded people that are either locals or people that are traveling as well. 

So, those are some kinds of things that will happen. I mean, if you’re single, dating is, you know, an easy way to connect with local people and meet a lot of people. When I was single and traveling around the world, I found that that was a good way where even a lot of the time like, even if you don’t like super hit it off with people, you end up starting to make friends around and then they kind of teach you about local food and whatever. 

It’s kind of like a kind of secret way to sort of find out about restaurants and culture and learn things and connect with people from other places, right? So, these are some of the ways. So, there’s lots of ways, but you do need to put an effort in. It’s different than when you have a regular job in your, or you’re in college or whatever, and all your friends are just default, you know, you need to, you need to put the time in, you need to bring those relationships and then when you are away from these people, when you are traveling, and you want to keep those relationships, you need to keep them up. You need to, you know, even just like, replying to their stories are like, whatever, you know, to just kind of keep those relationships brewing. 

But of course the benefit is that when you’re not getting these default friendships that are from your, you know, regular job or university or whatever, you’re actually choosing these people right? 




So, you can actually be a bit more selective in choosing people that do have more common interests or common mindset or these kinds of  things versus just the random person who sat next to you or whatever. 

So, those are kind of my meet people tips. 


Yeah and also if you decide you don’t want to talk to them anymore, you may never see them again anyways. So, it really becomes relationships that you have to put effort in


For sure.


and they become so much more valuable that way because you’re both giving your time specifically to them. And it’s not just by happenstance that you do it or, you know, like you mentioned being in the same class. 

But yeah, it’s so interesting that you know, you mentioned all of these things because there is a lot of options and you even mentioned your fiance being Filipino and she reaches out to the community and I do know that the Filipino Community like once they know you’re Filipino, it’s like “oh my gosh!”. It’s a huge deal especially when you see each other in the different parts of the world and there’s a lot of us everywhere and you know this too, I’m sure, Jesse.


And yeah, then you know they got the hookups for the, you know, food that you want that they don’t have in the place where you are and this kind of stuff. So, little things like that, you know, and that can not just be for Filipinos, that could apply to any anyone or also just any interest or commonality, right, is kind of the main thread here, right? 

It’s like, “oh, maybe you’re into succulents or something.”. Well maybe there’s a succulent, succulents, you know in Lima, Peru group or something, whatever.


I love that. 

Thank you so much, just for giving us all of these different tips on how to meet people and sharing with us your journey. 

Now, let’s look forward to about 30 to 40 years from now and you’re looking back at your life, what legacy would you like to leave and what do you want to be remembered for? 


Wow, that’s a heavy question. I don’t think I spend a lot of time thinking about my legacy. I guess I would just, I would just hope that some of the people that haven’t taken the leaps that I have in life, maybe would see some of that as some sort of inspiration and realize that like, “oh, you can do these things. You can change your life. You can live in other places, you can be with other cultures, you can learn languages, you can try new food”, just, you don’t have to do what happened within a 10 mile radius of where you were born. 

There are many great things out there and hopefully, by leading by example, some people will get inspired to hear my story and say, “hey, I could do that too”.


Yeah and I feel like this is just the beginning for you, you know, there’s so much more that you’re doing, and we can definitely take a look at you and what you’ve done and see what’s possible. 

So, thank you so much, again, Jesse for being here with us. 

If our listeners want to learn more about you, where can they find you? 


The easiest place to get me is on Twitter, I’m pretty active there, so, it’s just  @jesseschoberg and you can check the show notes to get the spelling on that or if you are looking to add a blog on your website, as I mentioned, check out, which is where our main company is and we’re doing lots of cool stuff. 



Thanks so much again, Jesse, we really appreciate you!


Thanks for having me on!

Listen to Jesse’s extended interview where he talks about how to negotiate AirBnB stays.

What you’ll find:

In this episode, Jesse talks about how to negotiate AirBnB stays, so if you’ve ever wanted to learn how to get more out of your AirBnB rentals, listen now!

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Show Credits:

Audio Engineer: Ben Smith

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