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Ep. 238: How the founder of SafetyWing is changing digital nomad’s lives by giving them a safety net with Sondre Rasch

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In this episode, I speak with our sponsor, Sondre who is the co-founder and CEO of SafetyWing.

Which is A travel and medical incident insurance that is made specifically for digital nomads.

Born in Bergen, Norway, Sondre was a policy advisor for the government of Norway advising on social policies. 

After getting frustrated with the slow pace of government change, Sondre first founded SuperSide, a platform for freelance designers. 

It was here where he discovered the lack of a safety net for online remote workers. 

Then SafetyWing was born in 2018 and has since raised over 8 million dollars and is serving 60k+ happy clients as of today and still growing.

Listen on to find out how Sondre and SafetyWing are giving digital nomads and remote workers the same benefits as 9-5’ers!

Listen Below:


Ep. 237: How to make slow travel sustainable with Frank Thomae
My Offbeat Journey: Learning to Prioritize the Right Tasks!
Ep. 236: How this amateur traveler turned into an award winning globetrotter with Chris Christensen

Feel Safe While On the Road with SafetyWing™

This episode is sponsored by SafetyWing. 

Travel is no longer the same for nomads, and neither should our travel insurance.

Gone are the days where we have a one size fits all coverage, when our life is anything but ordinary.

That is why I am so excited to partner with SafetyWing, an insurance founded by nomads for nomads!

They know exactly what you need because they’ve been there too!

So if you are ready to get coverage from anywhere in the world, visit for more info.



Hey, everyone. Thank you so much for being here. I am really excited to be with my guest today. I’m here with Sondre.

Hey, Sondre. How are you? 


Hey, Debbie. How are you?


I am wonderful. Before we get to all of the journeys that you’ve had, can you tell us about you and why you live an offbeat life? 


Yes. I was born in Norway on the west coast, in a small town called Bergen. Everything is small in Norway population-sense although big mountains and vast fjords, few people. And I guess from an early age, I was interested in internet things. And I had this little venture, started a web hosting company, and had a server in my room. 

But I knew I wanted to somehow get to San Francisco where I’m currently at. But I got a bit knocked off that path, that kind of entrepreneurship path when I was drafted into the military because there’s a draft in Norway. And so that kind of made me a bit more of a conformist, I guess, for a few years. 

And so, I stayed and worked on different things. I worked in policy for the Norwegian Government and then I realized I needed to get back out. And I had discovered this possibility of digital nomadism and freelancing. 

So, I started part-time to do freelancing at Upwork as a writer. Writing for a finance magazine whilst at the same time, I was planning to quit my job and move to Berlin; was the first path that was much cheaper back then, this is 2014, 2015. 

And then I started the company part-time as well. And then, that actually worked out, not this company but the previous one. 

And that’s how I kind of got out, I suppose. 


Well, it’s not such a bad place to be in, right? You’re talking about fjords, all of this greenery, and just vast land of amazing things but I guess you wanted something more. And I think that’s most of us, right? 

You want something outside of your scope of reality and go out into the world and now you’re in San Francisco. Pretty much the dream that you had, being intact and San Francisco is literally, like, the number one place right now to be in if you want to be in that area of expertise. 

So how did that go about, Sondre? Because you’re talking about this guy who just had these big dreams and then that kind of, you mentioned, you lost all of that pretty much for a little while because of being drafted. Now, how did you go from zero to now having this incredible company that you had, SafetyWing, which is amazing? 

A lot of digital nomads use it and you’re pretty much one of the number one insurance for that. How did that go from zero now to where you are?


Yeah. I mean, a big part of it is motivation and goal-setting, I think. It definitely didn’t happen on its own. Some key things I think were important. My story was that when I was a teenager, like, 14, 15, I had this brush with, I guess what you could have called self-improvement literature which was super helpful. 

And I kind of learned goal-setting and I started from then on to write down a list of goals which I didn’t hit, like, 0%. Over the years, I kind of gradually reduced my goals. And when I was 23, I learned about planning, and then I started making plans which increased the achievement for a little bit. 

It took me ten years, I think, from starting, setting yearly goals to starting to reach them. I do think it was a key part of my story. But what was my motivation for the goals that I did set? I very much relate to the sentiment behind your podcast, and I’m sure also your listeners, which can probably be described as freedom. 

There are different kinds of freedom. We can approach it in a philosophical way like freedom from constraint or violence. The other kind of freedom is to do what you want to do. And there are even more kinds of freedom, I suppose. Like, some people talk about freedom over yourself, there’s something there as well. 

But whatever it was, it was kind of this sound of wanting to somehow get control of my own life and shape my own destiny – not in a hubristic way. It’s not that it’s so important for me to be recognized for that or anything, I just wanted my own freedom.


Yeah. That’s extremely understandable because, especially now with what the world is going through, I don’t think we appreciate it more than we do now because of what is happening around the world. Just traveling now is a true privilege. I mean, it was before but now it’s even more so, right? 

But I do want to go back to when you were a teenager when you had goals, and then when you figured out how to actually achieve them by planning. Can you explain that to us? Because people are probably saying and thinking, “What does that mean? Of course, you have goals, what does that have to do with planning? How does planning go into that to actually make you get those goals that you want to reach?” 


So this is evident. I’m sure I remember seeing research on it at some point that writing a plan increases the chance to reach your goal by something – I can’t remember. But it’s a significant percentage. 

In my case, it was from nothing to everything. Like, it was the big difference. So planning in the sense that I used to hit none of my goals and after I hit most of them. So, what is a plan? Plan is a step towards your goal. 

And I can’t remember where I learned this but for some reason, I just did it once. In some fit of inspiration, I just wrote down a plan for each of my goals and they all follow the format which was kind of, like, bullet points. Like, five, six, seven bullet points in each goal ordered in the sequence I would do them in. 

So, this first and then that and then that. And that was a really crucial thing to learn. So to give an example, when I set the goal that I wanted to become a digital nomad and quit my job, I wrote down this plan. I’m doing this maybe six or nine months before I actually quit my job at the beginning of the year.

And I wrote down steps and one of the steps was, for example, to get freelance income. Another was to cut expenses a lot. And I was trying to achieve the kind of digital nomad reasoning, which is if you’ll just have some financing coming and have low cost, I can work on my start-up most of the week and just, like, freelance part of the week. 

And so I had these steps written down and there was also time. So I knew I was going to quit my job in August, which was very terrifying. I had an interesting job, I was a policy adviser for the government of Norway. It was a very creative job, I was kind of thinking up new policies, gathering research, and presenting them. It was quite meaningful. 

But of course, I also was a bit frustrated because the government is a big organization. Very slow, kind of the opposite of startups in that way? 

So, yeah, so that’s an example. And by making that plan, I had something I was starting with the day after, right? So it wasn’t just this, like, a very difficult thing that was a goal in the future but I had the next step and later implemented that. Like, when I write a plan, I add all the first steps into my to-dos that day or the next day. 

Sometimes. I wonder if they seem to almost happen automatically. Sometimes a good plan is like a domino.




Where it’s like I want this big domino to fall and then you just put out these dominos in between, and then you just push the first one.


That’s a great analogy of that, actually. That is pretty excellent.
Because it’s true, right? It’s like you want that whole domino to fall but it only takes one for that little push and then it all falls into place. I love that. 


Yeah. So that was roughly it and I did that plan and that was how I was able to eventually quit my job, move out to start a company, get a freelance income, and all of that.


So when you were creating those step-by-step things, the plans that you had and, like you mentioned, were a little bit at a time, it was obviously realistic. One of the things that I always find when you are planning for something, for you to achieve that bigger goal that you have, a lot of the actions that you take are pretty monotonous, right? 

You have to do something over and over and over again before actually starting seeing the results. But you have to do it over and over again for a period of time. And I think a lot of people lose interest or they become bored or they don’t have the patience to do that, to wait for it to finally take effect. 

Do you feel like that happened to you when you were in those steps to get the essential goal of SafetyWing and the other businesses that you have?


I had my particular struggles when it comes to my own productivity. And some of them are things that I think a lot of people have, for example, when I’m not in a scenario where I have to do something. It was like, it’s hard to focus and not be distracted. 

That was like a bit of a monotonous struggle to figure out. TLDR: I had to work from different places where I’m relaxed – that was really important. The slow and boring steps. 

So the reason I’m struggling is because half of those slow and boring steps, I actually don’t think are worth doing, which is a bit of a mystery. From the first start-up to the second, the biggest difference was that I knew everything I didn’t have to do.

So in the first one, I didn’t know what was important so I did a lot of stuff. Basically, everything except gathering your team and making a product, something customers will love. It’s almost a waste of time and can be done later. 

But a lot of people only do those steps which aren’t those. Like, learning accounting, registering a company, or something.


Things that you can hire out for pretty much, right?


Yeah. And do later. Like, things that are only relevant if you succeed in making something anyone wants to buy.

Some things are really big. This is another kind of truism but it is so true, that kind of an 80-20 thing. I basically discovered that just a few things make almost all the difference in finding a company for me. 

And by only doing those, you can make it a lot easier. So that’s definitely something that was very useful for me. That said though, there are still things that are boring that you do have to do. There are just a few of them when I’ve gone through it once. 


Yeah. And now you can hire other people to do the boring stuff that you don’t like and maybe they actually enjoy them. 


Yeah. That’s the lovely thing, that people are different. And some people love what other people hate which is fantastic.


It’s amazing. And I love that you talked about understanding what you really have to prioritize when it comes to your task because you’re right, there are a lot of things that we do, especially when you’re just new at this, right? 

Whether you want to be an entrepreneur or a freelancer, you do a lot of things that you think are going to move the needle that really doesn’t. And then it takes a long time sometimes to find that out. But then after, like, months of doing it, you’re like, “Oh my gosh, this is actually not productive for me. So I’ve been wasting my time, all of this.” 

But then it’s actually also sometimes a good thing because now, you know where you need to go in that sense. So yes, it is kind of annoying but it’s a lesson learned that a lot of us have had to go through. 


Yeah. And there is a kind of thing that is super useful which is the difficulty of, like, doing something for the first time, repetitive thing. Almost everything, you’re bad at the first time and then you have to do it a few times before you get good at it. 

But it’s so easy to forget this when you get into the professional realm.




You have to expect to suck at it the first time, it doesn’t reflect on you. Like, that’s just reality. That’s how it is to do something for the first time. No one is, like, the world champion, the first time they do something. So that one, I also find really important but I keep forgetting. 


It’s true. I think we have these really high expectations on our performance right off the bat and it’s like, “We’re going to be really amazing at this,” especially for people who are high performers like yourself, Sondre. You really expect a lot from yourself and then, like you mentioned, you tend to forget that because even though you’re doing really well, there are certain things that you have to learn and you’re brand new again and it sucks. It sucks a lot. 

But like with most things, as long as you can get over that first time and you accept failure, ’cause it happens a lot even when you’re successful, failure still happens. And I think for the most part too, failure happens a lot more for people who are successful but they just keep going and that’s why they win a little bit more than everybody else ’cause they fail a lot more. 


Yeah, absolutely. This is something I wish I could get, like, perfectly comfortable with, failure, because it is true, it is the method.

It’s even more true in startups because there, you have the thing that you want to do a few times to get even adequate at it. But you also have the thing where you have to try a series of things until you find the one thing. That’s not just, like, on the idea but it’s like, “How am I gonna market this product or how should this particular sign-up flow look?”

You kind of have to cycle through ideas. And that is the method to get lucky, to succeed. So you kind of just have to understand that that is the process you’re engaged in and not the process of getting it right the first time.


Yeah. I was talking to somebody and they were saying it’s kind of, like, being a scientist. You’re always experimenting with something. So when the first experiment doesn’t work, it’s okay because you’re going to experiment with the next one and the next one until you get it right. 

So I’m like, “I love that. We’re like scientists in a way. So it’s not really a failure, it’s just a bunch of experiments and we figure out what works for us.



I first started one company, Superside, which is still active –  doing well. It’s a design platform that does projects for companies. And then it was there that I discovered this other problem, which was freelancers wanted some kind of benefits. We didn’t know where to get it then and that became the Genesis of  SafetyWing. 

So when I did that the second time around, one thing that was lovely is that I’m so thankful that there is knowledge to be had also in startups. It’s not only those specific to your problem. There are these lessons that are true across startups, which was a huge time saver the second time around.


Well, talking about SafetyWing, one of the things that I really love about your company, this insurance company, is that it was and is still run by digital nomads, right? And that’s really one of the things that make you stand out is because you know what digital nomads need because you’ve been in their shoes and you have employees who are remote workers, digital nomads. So this is really for them and they run it themselves. 

So can you tell us about how you got the idea for SafetyWing and really just give us a gist of everything that you do because I think it’s such an interesting time right now because there are so much more remote workers that you can reach. 



I was holding my own problem in the sense that I was a digital nomad myself as well as my co-founders. So we knew exactly the problem, we knew exactly what this product needed to be attractive to us. And I was a huge help.

When I think about, like, start-up ideas, I pondered upon before that actually wasn’t good but that seemed good for a while. They all have the same thing, it wasn’t really my problem. And it is possible to do something that isn’t your problem but you’re much more likely to fool yourself into thinking it’s a good idea when it isn’t. 

So that was really good, being around customers, building something for ourselves first, and being, like, one of our customers in a way. We were very excited for a product to be done because we needed it. 

It later became true when we launched Remote Health, a health insurance for remote teams. So this is part of that. The vision is to make a global social safety net for a country on the internet but I have to make each piece at the time. 

So health insurance was the next one and by that point, we had become a remote company, like you said. So we were also very excited for that product to be done because then we needed that for our new fledgling company and remote team to be able to get health insurance even though they were in many parts of the world. 


Yeah. So what would you say that you found, as digital nomads as remote workers, was the difference? Because what is really the difference between a digital nomad insurance, remote work insurance, and just like a regular insurance that somebody would have?


Yeah. So the key part is digital nomad and remote work, health insurance is global. Meaning that it works in every country. So digital nomad insurance is different from the remote health thing in that it doesn’t work in your home country. So that’s only when you’re abroad but it works everywhere else. And remote health, which also works in your home country. 

So it’s literally your primary health insurance. You can add, like, dental and vision, and it’s sort of just the regular good, easy to use, and cool kind of health insurance. But if you do move or if you do stay abroad, 3 months of the year, six months out of the year, you’re on the same health plan and have the same coverage there as when you’re home. 


That’s pretty incredible. That’s amazing because then you can truly be a digital nomad in that sense. You don’t have to worry about insurance when you’re at home when you’re abroad and it’s kind of all-encompassing everything that you need, right? 

So for somebody who already has maybe health insurance in their home country, is there any difference with that or that they can look at in terms of which ones to look for? How can they sign up and all of that? 


Yeah. So, pricing-wise, the nomad insurances are pretty light. So that’s, like, $40 a month. 


Oh, wow. That’s really cheap.




‘Cause, Sondre, here in the US,  I don’t even want to say how much I’m paying right now for health insurance.


Yeah. It’s kind of the rest of the world and then the US.

If you compare it to having health insurance in the US, remote health is like the standard health insurance. Nomad insurance is like lightweight health insurance. What I mean by lightweight, it covers up to $250,000 while remote health covers up to kind of, like, a million-and-a-half which is roughly kind of everything for a thing. 

And remote health costs more, it depends if you buy us a group and which add-ons you have. But, like, from ninety to a hundred and fifty or even higher.


That is super affordable. That’s really good. 

Alright, how can we all sign up for this though? 


Right. Yeah. I mean, we talked about freedom in the beginning. We do have the help that, like you said, to reduce the barrier to move abroad. One of the things is, like, there are a few things that are important if you want to become a digital nomad. 

Maybe number one is to have remote internet income of some sort but, after that, deciding where you want to go and then figuring out the basics so you’re not getting, like, insurance. So by making that super easy and straightforward, I do think we are making the barrier for people to make that escape themselves a little bit easier.


Yeah. And are there any specific requirements for somebody to be approved with SafetyWing or is it just anybody who’s a digital nomad or maybe moving abroad can be approved for it? 


No. So nomad insurance can be bought by anyone. We have one limitation from 70-year-olds that we want to get out of but that is a constraint with our insurance partner. But if you’re younger than 70, then you can sign up. 


Perfect. That’s pretty amazing. I mean, it seems, like, it’s very affordable, doesn’t really have a requirement unless you’re over 70 and yeah, that’s pretty great. Because now you can literally move wherever you want and not have to have that extra worry. Because I think a lot more people are worried about health insurance with what’s happening in the world right now. 

And it is amazing that we have a company like yours, Sondre, because, again, it was started by you, a digital nomad, your co-founders are all digital nomads, you’re a remote working company who knows exactly what we’re all going through. So I think it’s one of the best places to really look into this. 

I love that and you guys could go to and take a look at the link to apply. I’m sure you’re going to get approved for it, for SafetyWing. I love that. 

So for you, Sondre, how does it feel that you finally have this company? And I’m sure you still have these big dreams for SafetyWing and what you’re going to do with the world. Because now it is really a very remote work, friendly environment that you have. And I’m pretty sure that these visions have changed in the last two years. 

Where do you see yourself in a few years, like, what do you want your legacy to be in about 30 to 50 years from now? 


So SafetyWing’s mission actually hasn’t changed since the first day, which is very cool. And the main legacy I can imagine having right now is to completely fulfill the project, to complete it. Because the project is to build a global social safety net. Meaning that anyone in the world can and also the first country on the internet. That’s the mission of SafetyWing and it is a big project.

So it is to make the health insurance as we have now and make that even better and better and then add other services like remote retirement, and other things until we have a membership that’s, like, equivalent to what we had back in Norway when I was working with the government there, to be sort of a citizen of this internet country in addition to your regular ones. 

I think it still sounds esoteric but much less so than it did when we started out, I should say because of the remote work change that has happened. I broadly think that the shift to the internet is still the big thing of our age and we’re still in the middle of it.

Some industries went first like, I don’t know, music or video. Video stores and music stores are closing and now everyone is just using Spotify, Netflix, and YouTube to do that. But similar changes will happen also in areas that today are done by governments or insurance companies, the things that move a bit later, the slower.

And we think we can contribute to building solutions that work also in the future. And if we’re right, then this is a big deal, that it’s very important that we succeed. That is the main thing that I want is to fulfill the project.

I should also say I recently got married, love to start a family, and build a happy life with them.


That’s amazing. Congratulations.

And I’m really excited about this, like, internet country that you want to create ‘cause I’m like, “I’ve never heard of that. That’s really interesting. As long as I don’t get drafted into your military, I’m okay.” I’m like, “That sounds like a really cool idea. Sign me up for that. I love it.” 

And yeah, congratulations on getting married and this is definitely something you’re creating for yourself and also for your future, for your children, and so forth. So, It’s a great legacy that you’re building for yourself, for your family, and everyone else in this space. 

Well, thank you so much for being here with us. If our listeners want to know more about you, where can they find you?


So is the website for the company. We also have a project called Borderless, if you want to see, like, updated twice a week, travel restrictions around the world, that’s on Borderless with 

And we’re also doing a project to help people start a remote company called where there’s a podcast and some writing. So if you’re considering starting a start-up remotely, you might want to check that out of


Love it. There are so many resources that you have there for us, Sondre, we really appreciate it. And we really appreciate you for being here and sharing your journey with us.


Thanks, Debbie. Great to be here.

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Show Credits:

Audio Engineer: Ben Smith

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