Matt Bowles: My guest today is Sondre Rasch. He is the co-founder and CEO of  Safety Wing, a fully remote team that is building a global social safety net. Safety Wing offers Nomad Travel Insurance that covers you while traveling worldwide, including COVID 19, quarantine coverage, medical and political evacuation, and even lost luggage and trip delay coverage. They also offer remote health insurance for nomads that includes comprehensive coverage in your home country such as vision, dental and preemptive screenings. Safety Wing also offers a comprehensive health insurance solution for remote companies that covers all team members globally, no matter where they are in the world. Safety Wing’s long-term vision is to remove the role of geographical borders as a barrier to equal opportunities and freedom for everyone by creating a home country on the Internet as well as bundling the financial security of global health insurance, disability insurance and pension savings into one global membership. Born in Bergen, Norway, after getting a degree in economics and computer science, Sandra worked for the government of Norway advising on social policies and then left and founded his first company, Superside, as a platform for freelance designers. It was here that he discovered the lack of a safety net for online remote workers and subsequently co-founded Safety Wing in 2018. And Safety Wing has since raised over $13 million and has grown their community to nearly 100,000 happy customers.

Sondre, welcome to the show.

Sondre Rasch: Matthew, thank you very much. That was the best intro I ever heard.

Matt Bowles: Man, you deserve an amazing intro because you guys are fundamentally disrupting the health insurance space and doing amazing things in the nomad world, man. We know a lot of people in common so I’m super excited to finally have you on the show.

Sondre Rasch: Thank you. Glad to be here.

Matt Bowles: Well, let’s start off just by setting the scene for folks and talk about where we are recording this from today, unfortunately, we are not in person. I am actually in San Salvador in Central America, the capital of El Salvador. And where are you today?

Sondre Rasch: I am in San Francisco in the Bay Area, formerly known as the tech capital of the world.

Matt Bowles: That’s an amazing city to be in, man. A lot of love for the Bay Area. I have a lot of friends from the Bay, currently in the Bay and all of that. So, love getting up there to visit as often as I can. Well, let’s go all the way back, man. I want to start off with your background a little bit. Can you share where you grew up and as you were growing up, how your interest in international travel developed?

Sondre Rasch: Yes. So, I grew up in Bergen, Norway, which is on the west coast. It’s historically an international city. It was a Hanseatic trading town, so it had German names. It was like a free town separated from the rest of Norwegian society in the Middle Ages for a little while. So, I grew up there and it’s a medium sized Norwegian city and it’s a wonderful place. You know, Norway is beautiful nature wise fjords and the mountains and the northern lights and the nature is dramatic and it’s a beautiful place to visit and the people and the culture is also remarkable thing. It’s kind of like, it’s the most like the Shire kind of almost that I know about, you know, it’s very sweet and innocent and people are very trusting. They don’t lock their doors and if you forgot your wallet at the store they’re going to say like, oh yeah, just come back and pay tomorrow or like the next time. So, it’s this like very, very high trust environment.

And yeah, so that was where I grew up and I got to know international travel in multiple ways. There was a one trip to Cuba and a camp there with a lot of international people. There were people that came from 140 different countries. And so that really inspired me to go all those places they were from. And another one was just the discovery of Interrail. So of course, being young and not having money, there’s this great invention. If you haven’t tried it yet, you can buy this plane ticket in Europe where you kind of have unlimited rides. And I just love going to the train station and deciding where to go on the train station, like just checking weather reports where it’s next, Brussels or Venice and then we would go and I’ve done that three summers.

Matt Bowles: That’s amazing, man. Well, if you can believe it, I have actually not yet been to Norway. It is super high on my list. I mean the whole Scandinavia; northern European region is high on my list in a place that I have not spent time. So, for other folks like me that haven’t been there, can you share a little bit about sort of top highlights in Norway? And if people were going to come there to visit and maybe even spend an extended time, you know, based there for a little bit as a nomad, what would be your top recommendations? Especially even for people that haven’t really even there, not even familiar with the fjords and what some of the big international highlights are. Can you sort of describe that?

Sondre Rasch: Yes. So, Oslo is sort of fine, but that’s like in a regular cosmopolitan city. It is surrounded by some great nature though, so a lot of people would fly in there. But I would probably put my hometown Bergen as the base if I were to go, because that’s, you know, it’s more Norwegian in some sense, more different. There you have Bargen, which is this like thousand-year-old harbor and these colorful quaint houses. At the end of that harbor is this 1200-year-old castle, which you know was at the time, you know, the gathering of Norway, which was back in the Viking age. You know, that was the seat of the crown in that city. And you know, that town has so many curiosities. You know, there is this tram that goes up a mountain. It’s surrounded by seven mountains. It also has a bunch of famous historical figures and composer like Edward Craig would visit their homes. It’s a great base to go to a few of the other places.

So definitely on like a fjord trip there is this boat trip called Hurti Rutten that you can take out of there. You can also take it out of other places, but I think that’s a good place to start that kind of goes with a boat, kind of like a cruise, but up the fjords. That’s a good one. You can also go to Voss, kind of famous extreme sport place that’s about an hour drive from Bergen or you can go with the train one step further. Just a train ride by the way, from Oslo to Bergen. Great. There are big windows on this train. It was built 1905, so it actually goes through an amazing terrain like on the mountains. You know what awesome thing that not many people know about that I would recommend is to stop at Faenza station with a train and then you rent a bike. If you’re in the summer and you just drive, you go with the bike. It’s called Roller Wagen. It’s this Old Road made for the people who are building the railway.

And it’s so cool to go down on bike. It’s just like downhill all the way for hours and hours and hours in a very cool dramatic landscape. And then if you’re a nomad, you know, you could live there. There’s actually pretty kind of for the size of the city, great music scene there and every kind of convenience co working spaces. Or you could go up to Lofton if you want that kind of most dramatic Norway scene there. You have mountains coming up out of the water and it’s like, how did this even form the most unusual landscape? And you have northern lights and all kinds of. There is a significant contingent of nomads there as well, even though it’s a small town, so. But, you know, less urban. If you’re going to focus on work and just be in a spectacular place and do some great hiking, then Lofton is the place.

Matt Bowles: That’s amazing, man. Norway is so high on my bucket list. I really got to make this happen imminently. So, let’s talk a little bit about that Cuba trip. So, you’re a teenager and Cuba is obviously extremely different from Norway. So, can you share a little bit about what that trip was like for you and what impact that had on you at that age?

Sondre Rasch: Yes, Cuba is very different. It’s changing. So, it was first year in 2006. Impacts besides like practicing salsa dancing and trying cigars and rum. Of course. It’s a bizarre society. You know, it’s like you come there. I read this newspaper Gramma on the way down and I did recall having this experience, like, why are all these newspaper stories about the same thing? Because there’s like five stories which kind of goes on repeat. And they’re all kind of various stories around how the U.S. blockade is the cause of their misery, whichever misery it happens to be. And there’s this like five stories that goes circles. I remember that was the first one because I wasn’t familiar with this angle then.

But of course, they do have this revolution that’s been going on, still going strong since 1950 something. And they sing and celebrate a lot on that. They kind of laugh at the television being repetitive, but they have the great spirit about it still. And they still find it very romantic. And it’s very romantic people. So that’s one, you know, seeing people. People dance in the streets. People don’t do that in Norway. So, it’s like Tuesday in Havana. You cross a corner; someone is just playing music in the street and dancing there and why shouldn’t they be? No, that’s just normal. That was just seeing a different place, meeting people from all over the world. I was probably the best thing there. Getting to know them really well and seeing where they were from and hearing about their takes on things. And it was an incredibly fulfilling experience to get to know people from 140 different countries and becoming friends with them. It was really an inspiration to explore more and meet more people.

Matt Bowles: That’s awesome, man. So, from there, let’s talk a little bit now about your professional trajectory and the path that ultimately led you to entrepreneurship and becoming a digital nomad. Can you take us on that journey?

Sondre Rasch: Yes. So, I had a little stint in my teenage years. I had this little web hosting company in my room. I was trying. I would try to set up a server, had customer service on my newly acquired Siemens C25 mobile phone. And I did that with a Dutch and Romanian person that I met online through a game called Planetarian. So that was my, like my little foray into that. So, I even tried kind of remote work. We’re talking here in 1999, 2000. So, I was an early adopter of remote work and the possibilities. So, I grew up in the Internet in some sense, and so I was native to that. I went off and did other things, as you mentioned in the intro, got interested in economics, advised the government of Norway on the social policy.

And then I got a bit disillusioned. Government is. There’s big important topics, but it’s also a big slow organization. And so, I returned to startups. And that was kind of like my second foray into remote work, you know, because then I had to quit my job and actually loved this job. I had a great job, it was really a nice time, but I had to do it. And so, I planned to quit my job. And I knew about the concept of digital nomad isn’t at the time. I had this idea that I would cut my expenses, I would save up some. I would try to get some freelance writing income and move to Berlin. I was going to quit my job on a date and I believe it was August 1st. I think it’s like six months away when I make this decision. And I try to save up a lot and really cut my expenses to build up a runway, a personal runway.

Another great idea I came across at the time. I think I was able to save up $15,000. And then I thought I could have like a year in Berlin or something. And I also was able to get a freelance writing job on Upwork. And then I also started work the weekends and evenings on my startup, Superside. And as it happens, the day comes, I quit my job and it’s. That’s super scary, by the way. And then what happens is that that goes really well quite fast. And we apply to this program called Y Combinator. And so, what I envisioned of, like years of very relaxed Nomad experience became very fast, like a rocket. And I was on some plane to San Francisco to participate in this program with my company. So that was the beginning.

Matt Bowles: Can you share a little bit more about Y Combinator for people that have not heard of it? I know you have now done the program twice, but it is an extremely prominent and revered incubator. Can you share a little bit about what Y Combinator actually is, what it does, and how your experience was doing that program?

Sondre Rasch: Yes. So, Y Combinator is. Well, I guess it’s the original accelerator and it was founded by Paul Graham, who has already known before that. I mean, he was kind of the inventor of software as a service, I guess, which is now a startup category. And he has this book, Hackers and Pinterest. He also had a blog, which I read, where he writes a lot of startup wisdom that I would definitely recommend. And I was also paying attention to this kind of news site, sort of Reddit clone that White Combinator had called Hacker News.

So, I was paying attention to this and it was a bit of a dream. You know, Silicon Valley is this mythical place, but White Combinator is like, you know, the Hogwarts of Silicon Valley. I thought that would be amazing. And I applied, not actually expect thinking to get in, but it was. Somebody said, oh, I should fill out the Y Combinator application to improve my idea, which was a good idea, actually a good suggestion. And then they fly you in and you go through this program, very intense three months, and then there’s demo day and you raise money and you also get this cohort of call. Like, it’s like you get peers, other founders who are at the beginning of that journey. And it’s great. And many of those are my best friends to this day. So, it’s a lovely program and I would very much recommend it to anyone considering.

Matt Bowles: What tips do you have for someone that is interested in applying for Y Combinator in terms of what they’re looking for and application suggestions for increasing the likelihood of being accepted into the program?

Sondre Rasch: Yes. So, I would say you want to have something that can become huge, have an idea that can become huge. I definitely think that’s a qualifier. They’re trying to build big things. So, two, write the application very concisely and confidently. All the applications I’ve read, always I’ve given that feedback, like, cut it by half. And I don’t mean like the bottom half, but like make it more precise. And I guarantee if I was reviewing your Y Combinator application, that would be part of the feedback. Make it more confident, you know, don’t give too much a defense or context. Just say what you think it is and yeah, then I think you might have a chance to get in. Oh, and the other part is if you don’t get in the first time, make a lot of progress till the second time because they do track that and then be growing like 10% a week for two, three months, then you’ll get in.

Matt Bowles: Awesome. That’s amazing. Cool. We’re going to link up all of the stuff we’re talking about in the show notes so folks can just go there in one place and they’ll have all the links to everything that we just discuss on this episode. Sondre, let me ask you this now. You did your first startup; you went through Y Combinator. Can you share a little bit about from there? How did the idea for Safety Wing eventually come about? What were your personal experiences? I guess both from the company side in terms of running a company as well as from the customer side of being a digital nomad and needing health insurance. Can you go through that experience a little bit and talk about sort of the origins of the idea for Safety Wing, the pain points, the void and the problem that you observed?

Sondre Rasch: Yes. So, the problem I discovered was I running this company, Superside Freelance design platforms. We wanted to provide benefits. That came up as an idea quite early on, actually, right after Y Combinator. You know, both me and my co-founder were interested in that sort of thing and we looked at income protection. We knew that this was a problem freelancer had of very variable income and not having necessarily benefits like health insurance either. So, we looked into it and then we found that it wasn’t available because it’s like our freelancers were all over the world and it had to be flexible.

And that was kind of when I realized it. I didn’t think we were like doing something that was niche. I thought we were doing something that was early, meaning that I understood that we were working remotely with online freelancing and in the future most people would be working like that. Now that’s kind of common knowledge, but back then it wasn’t, which meant that I also realized that the fact that we had this problem, we wanted to buy this and couldn’t meant that in the future this is going to be a big problem. So that’s why I realized that somebody had to build a global social safety net. And the underlying problem, the way I see it now, and actually still saw it then, is that remote work makes the world a global labor market where people can hire or apply for jobs across borders. Hire across borders, but the infrastructure that supports the labor market is national. So that has to be rebuilt in a global, national way on the Internet.

For a year, I actually went around saying about what I said now and then I said, do you want to start this company and we’ll be your first customer. That was my pitch. And then everyone was like, nah, that sounds too difficult. So, after a little over a year during back in Norway for Christmas holidays, and I was just talking to my co-founders now and we were like, you know what? Nobody else is going to do this. We don’t know anything about insurance and stuff. But I actually did work with this in Norway. So how about we build something like the Norwegian social safety net, but available globally and digitally on the Internet? And that was what we set out to do.

Matt Bowles: That’s amazing, man. Well, let me just ask you a couple fundamental questions just about the economics and the financial infrastructure and the profit model and everything else of this company. It strikes me that in the United States, especially for example, where I am from, that there is an incredibly adversarial relationship, it appears, between an insurance company and their customers in that the profit model is basically to sell as many insurance policies as possible and then try to pay out on as few of them as possible to create the highest price profit. So, with this concept in mind, how did you assess that and navigate that and create a different type of insurance model?

Sondre Rasch: Yeah. Yes. I mean, this is so true. I mean, there are only two pieces to fix the kind of incentive mess you described there. So one is that the distribution model. So, the way insurance is sold today, you know, when we were first starting out, a lot of people were telling us a lot of these like truisms, like things they think are true in the industry, which are not true, but it’s so established knowledge that people can’t imagine anything else. So, for example, we just set up a website and we said people are just going to go to this website and buy it via word of mouth. That was kind of how we started out. And that seemed like a joke to people in the industry because they had this. That nobody would do that, but that’s because their products suck. And then instead they would incentivize these very aggressive salespeople who would then get 30, 50 for life insurance, even 90% commission to kind of put this insurance on people, which made the distribution very expensive. And that’s like how most of these products are distributed to this day.

So, by us just selling directly, that’s a big, like that whole thing on the distribution side goes away. Okay? So that’s half the incentive issue and then the other half, because if you can distribute directly online, then you don’t have that. And then on the other side, you just have to set up the structure so that you can’t make more money by not paying claims. You just have to set that. And obviously that’s easy to set up. In our case, it’s just as it is right now. There’s a fixed fee we can get. So, if claims go up, you know, at worst, prices over time will go up. Right. If you think about what insurance is, it’s like we as a community pool money. And then there are rules for when you can take money out of the pile and the cost is the average expected payout. Right.

And we as the company kind of administering that pool and say that it’s fair and well administered. We are administrating that community service in a way. So that’s, I think, the appropriate way to set up the incentives. And as long as you solve those two sides, then I think you avoid coming in that adversarial relationship and then insurance will return to being what it really is. You know, we don’t really see ourselves as an insurance company, you know, a community product, global social safety net that happens to have built a few insurance products. And that’s purely because we had to.

Matt Bowles: Well, one of the first questions that I get when I tell people I’m a digital nomad. I’ve had no permanent base for nine years. I’ve lived in 65 different countries. They say, what do you do about health insurance? It’s literally one of the first questions I get along with dating and like, you know what, how does it work, right? How does that lifestyle work? Health insurance is always one of the at least top three, if not top one question that I get. So, what I would really love to do for all of the nomads, aspiring nomads and everybody else is just wondering how the nomad thing works. To go through a couple of the insurance products or services or opportunities here that you have available. And let’s just start with the Nomad Travel Medical Insurance offering. Can you share a little bit about what that is and what that includes?

Sondre Rasch: Yes. So, if you are a nomad or an aspiring starting out nomad, then you can buy the Nomad Insurance at $42 a month outside the U.S. there’s an add on, slightly more expensive if you’re in the U.S. and that’s fully flexible. You can also buy it for a specific number of days. Sometimes you need that for a visa letter, but generally people use it, they would buy the product, you can pause it whenever, so you can kind of go month by month and if you return home, you can pause it. It covers you at home for up to 30 days, every 90 days. So, you can’t perpetually be at home, but it does cover you if you go back home for a visit or something. Yeah, it covers like you mentioned in the intro, medical expenses, things that happen, reason, you know, for you get ill or injured and you need to get treated and then also travel things, things like political evacuation, a natural disaster evacuation, lost luggage, et cetera. So, it’s meant to be this like what you need as a nomad. The different thing from regular travel is that you just have it on a subscription indefinitely. So even if you’re out for years, you can just be on the Nomad Insurance plan perpetually.

Matt Bowles: Awesome. Okay, and you mentioned in the future the price could potentially adjust, but at the time of recording to book this particular policy for a month-long period, if you’re in that 18- to 39-year-old age group and then as you get older in different age groups above that, the price adjusts. But I love that you guys have a calculator on your website and we’ll link that up in the show notes so folks can go and type in their exact information. But just using as an example, if you’re in that 18- to 39-year-old age group, it comes with a $250 deductible. And I’m on your website right now checking this out. But 42 bucks a month and that includes hospital rooms, nursing services, intensive care, ambulance, physical therapy, all this kind of stuff, emergency dental, as well as the COVID 19 quarantine requirements outside of your home country. So, if you come down with COVID and you are required to quarantine, you actually get a daily payout to cover your expenses while you’re in quarantine, right?

Sondre Rasch: That’s correct, yes. That we have done to adjustments on the policy during COVID First was 2020 to actually cover COVID, which was actually a controversial move at the time because in the beginning people didn’t know how it was going to go and how many would get it. Then later, when the quarantine thing started being an issue, and then we also added the quarantine coverage, which has been both of them very popular.

Matt Bowles: That’s awesome. And I love also that it includes trip interruption, travel delays, lost luggage, all of that kind of stuff, as well as if you a political or medical evacuation. So that’s really amazing. And we’re going to link it up so folks can go and read all of the exact details and put in their own age and their own details and stuff like that. And it covers also, let me see if I understand this correctly, if you’re abroad for at least 90 days, you can then also come home and visit your home country and be covered for 30 days in your home country, unless you’re an American, in which case you could be covered for 15 days in your home country.

Sondre Rasch: Correct? Exactly. Yes.

Matt Bowles: That’s awesome. So, let’s now talk a little bit about the other insurance product because that one that we just discussed does not cover your preemptive pre screenings and your regular sort of dental and vision and stuff like that. That’s more of like if something befalls you while you’re out in the world and you become sick or you have an emergency need for something that happens or something like that, you’ll be covered on the road. But it’s not. It doesn’t cover your annual pre screenings and your regular dental cleaning visits and your regular vision and all of that kind of stuff. So, if somebody wants that, the more comprehensive policy. Can you talk about your remote health insurance plan?

Sondre Rasch: Yes. You’re a great explainer. We need someone like you on the team. So. Yes, exactly. That’s what it does. If you’re a veteran nomad, you have preexisting conditions. Like you said, you want a more comprehensive plan that covers those preventative things, not just when something happens, but the checkups. Then you want to get Remote health or Nomad health that it is called if you’re an individual. So, this is like a full regular Health Insurance. You’re familiar with the sort of U.S. context that would cover anything roughly. Like there are no big exclusions in the same sense that Nomad Insurance has a few big exclusions, biggest of one being the preexisting conditions exclusion. So, if you buy Nomad Insurance and you have like an ongoing treatment program, you can’t use the insurance to pay for that. That’s how that works.

But with Remote Health, you can and you can also add dental and vision. And that’s also why this is also offered then as a benefit for, for remote teams. So, companies who want to offer benefits, but they have remote teams, employees or contractors in many different countries, they can then offer the same benefit to everyone. And there’s like a dashboard very easily it can add members to the plan and those members can even have dependents. And it’s a global plan. So, it still has that benefit of being global, meaning that if they move to a different country or if their spouse is in a different country even, than they, you know, they still have that same high-quality coverage. So that’s how that works.

Matt Bowles: So, we mentioned with the Nomad Travel Medical Insurance that if you’re from the United States, you’re allowed to go back for 15 days and still be covered. What about for this Remote Health Insurance plan, what if you’re from the United States and that’s your home country, or you’re talking about a company that has some remote workers, some of whom are in the United States or from the United States. What restrictions are there in that case?

Sondre Rasch: Yes, well, I mean, I wish you didn’t say the United States, because that is the one where we still are working on getting a full perpetual coverage. Unfortunately, you can only have up to six months. If you have more than that, then it’s a local plan, it’s not the remote health plan. But any other country in the world. 180 countries, that’s the big difference. If you’re from Mexico and you’re in Mexico, you can have remote health and have that as your regular health insurance in your home country. So, it’s a truly global one.

Matt Bowles: And what if you’re from the United States and you’re out of the United States for like 11 months of the year, let’s say there’s a lot of Americans that get the foreign earned income expense exclusion for tax purposes, and they’re out for 11 months and they’re in for a month visiting family and stuff like that. I mean, that’s a lot of the time. You know what I’m doing, right? How does that work? Is the remote health insurance plan still available for Americans if they’re out of the U.S. for most of the year?

Sondre Rasch: Yes.

Matt Bowles: So, if they just come back for, let’s say, one month out of the year, are they able to get their preemptive screenings and dental and vision and kind of like pack it all into a month and then they’re out in the world for 11 months? Is that still a plan that’s available to them.

Sondre Rasch: Yes. So, for trips, you don’t even need to have the U.S. Add on. So, if you’re just going home in that example for a trip, then you would still be covered in the U.S. during that time with remote health. If you plan to live in the U.S. for up to six months out of the year, then you need to get the U.S. add on, which increases the price a little bit. But yeah, so that’s already available today.

Matt Bowles: Awesome. Amazing. Okay, so we are going to link all this up in the show notes and folks can go directly to the links. You can see all of the details about exactly what’s covered, what’s different for Americans versus everybody else in the world, and then how the different age categories break out in terms of your monthly fees. One of the things that I love about these policies though, is that you can buy them while you are abroad. You don’t have to be in your home country to start the program. You can just go to the link wherever you are, whatever country you’re in. I’m in El Salvador. I can just click on the link and I can buy it and then you can renew it as a subscription every month and just rock and roll, man. So, I love that feature.

Sondre Rasch: Absolutely. I mean, we built it. We obviously were nomads ourselves, the co-founders, and we just looked at our own situation and we built it so that it would work for us. And of course, then it also works for a lot of other people in the same situation.

Matt Bowles: Well, I want to talk to you a little bit now about your entrepreneurial journey and lessons and insights a little behind the scenes about how you’ve been able to do some of the incredible stuff that you’ve been able to do. Let’s start at the very beginning because I feel like one of the things that is incredibly important at the very start is selecting the right business partners and the right co-founders. Can you talk a little bit about your co-founders and how you found them and selected them and teamed up?

Sondre Rasch: Yes, absolutely. I’ve started two companies, so there are two sets. So, you know, let me start with the first one; Frederick Superside. So, Frederick and I, we met first day in college and we were kind of disagreeing on a lot, but in a very productive way. So, we were like just got into this conversation on economics or. And we would just go for hours and hours after school and suddenly it was evening and we had to bike home. So, the main thing that I really was fortunate with Frederik was the thing to look for is, you know, creative and determined. The program has this expression, relentlessly resourceful, that kind of James Bond. But it’s kind of you’re looking for someone who comes up with ideas to get you out of situations and to generate ideas. And then the other part is someone you can trust and you know long enough to know for sure. And definitely had that with Frederik because we had many projects together throughout college. We had a relationship that transcended the startup.

So, when we started and when we ended, you know, still a good friend, great friend to this day. So those are some of the key pieces. The second one had a similar thing, you know, then I knew what was important. And so, both Hans, you know, and there also looked a bit for complementarity. Another kind of Y combinator thing is like one person has to be the technical and, in our product, you know, that was like we needed a developer. So that was Sarah. She’s worked on projects, building things together. And she was also a nomad working on this kind of financial product herself and was like ultra-nomad, like traveling the world, being a musician, being going on meditation retreats. And then you had Hans, he was a lawyer, head of legal at a Fintech fast growing company. And together with my experience from knowing the problem, we had what it took together to build it.

Another thing that I really appreciated with them and I really put a lot of emphasis on second time around is I just knew how intense it gets when things are hard in a startup. And so, one thing I’ve been really appreciating this second time around is they’re really good when things are hard for different reasons. So, I am good in a way because, I’m positive. So, I’m always looking for the good thing, the way out, the solution. And Hans, he just makes things simple. He doesn’t get stressed out like extremely low neuroticism as it says in the personality test, which just means that he copes very well with the difficulties. And then you have Sarah, she just believes she’s just like it’s going to be okay and doesn’t need assurances for a bizarre reason. So anyway, that’s another thing that I really put a lot of weight to and been very grateful for as time passed on.

Matt Bowles: Well, you have scaled Safety Wing at an incredibly impressive rate. 100,000 customers already. You’ve raised over $13 million. Can you talk a little bit about how you did that? Just sort of take us behind the scenes a little bit and maybe talk about some of the biggest leverage points that allowed you to scale the company that quickly?

Sondre Rasch: Absolutely. I tried Superside. One thing, a benefit I had with Fredrik, which was amazing, is that we both didn’t take ourselves too seriously. And so, we just tried many things until we find one that worked. And we made decisions very fast. Like just I remember the first day, we had already settled on the name, registered the domain, made the logo, and we were kind of set the pricing. We were off to the races immediately. A lot of people, they just spent so much time in the beginning to get everything right. So, we got through a lot. So, the second time around, I kind of knew some things for sure that I learned the hard way. One of them was that the fundamental part of a startup is to make a product people love so much, they tell their friends about it.

That sentence has like so much meaning in my head. I realized that if I was hearing it for the first time, it probably wouldn’t register. But now after two stripes in I’m like, that sentence has everything you need to know if you just meditate on it long enough. You got to make something people love. And you do that by talking to your users, making something you would love. And then if they love it so much that they tell their friends about it, that’s a growth strategy. That’s product, market, fit, product and growth. That’s all it is about in the early days. And so, we optimized heavily to making this sentence true. And we succeeded with that with Safety Wing, with Nomad Insurance, which was kind of growing by word of mouth from day one due to really doing that. And one thing that we did, which not many people know is on the sort of brand side, I realized that important.

So, this is number two. We were very authentic and creative with our brand and product. Like, we were really trying to think for ourselves there. We were like making a product and a brand that we liked. And in a way where we were completely ignoring what we thought people wanted to hear. And people were shocked at this thing in the beginning. Like, our insurance partners were like, are you insane? What are these birds? And nobody’s going to take you seriously. You got to have light blue and white and maybe black. And we were like, no, we would like this teal and pink and these birds and they’re cute. And we weren’t trying to make an impression. We just had this idea that we thought this was cool. And so many people were like, I love this look you had, but other people are going to hate it. Well, it turns out that wasn’t true. And thankfully we didn’t listen to them. What that did was make us different. It gave us a distinctly different vibe in the company and that made us memorable. So, thinking for ourselves and being authentic to ourselves became a differentiator. And I think that was the second part that was really important.

Matt Bowles: What have been your primary marketing channels and the way that you’ve built your brand and gotten it out to the world? What would have been the most effective techniques for you in that realm?

Sondre Rasch: Yes, that’s really important. I would say with three and four, that would be number three. The first time around, I just tried everything. And everyone starts by trying this. They’re like, did you know you can segment based on anything on Facebook and Google? Yes, that is true, you can do that, but that does not automatically make that a good channel. And I did spend, you know, a few years and a couple of million dollars to learn that. So, the second time around, I had a lot more thinking about what channel was best. And a key insight is to look for something where we had a competitive advantage. So, the thing about Google AdWords is that it’s a public auction. Even if you succeed, which takes a long time just to get good at it, you’re still competing with huge incumbents who have much larger marketing budgets than yours, and you quickly run out of the sort of very targeted niche keywords that only apply to you. We just said no ads, and then we instead focused on what we could do that others couldn’t.

And for us, that was an ambassador program. We have this thing where we sponsored cool stuff and we would sponsor people to do reviews of our product and things like that. And that really worked. And this ambassador program has scaled with us since the beginning. The other thing we had was we knew we were good at software. And by the way, the reason they can’t do an ambassador program is that a lot of ambassadors won’t work with lame companies, but they love to work with us. So, we were playing to our strengths here because we were nice people. We were like the people we were, our ambassadors. Not that the others weren’t nice, but it’s like we were in our target segment ourselves, right? And then another one was we were good at software. So, we built this platform API that was only ready in 2020. It’s been remarkably successful. And that was something I realized from knowing this Freelancer platform. I knew if we made an API that the platforms could use to distribute the product, that would work. So that was another one that we did. And so, these three words of mouth, ambassador, platform API, those are our three channels.

Matt Bowles: Amazing. That’s awesome. Well, I also want to ask you a little bit about executive leadership and maybe just start off by asking you what is your personal leadership style and, in your opinion, what makes a great CEO?

Sondre Rasch: My personal leadership style, I guess starts with being vision and values oriented. This is something I also learn that you want to have a vision that is so interesting that it’s uniting and motivates day to day that kind of can pull people through difficult times. And you want to have values that if they’re optimized on everywhere, always, it will increase your chances of succeeding over time. That’s, I guess, the center piece of my leadership style. Other thing you know, I’m very leaning towards autonomous and responsible responsibility, meaning that I sort of try to hire people who have the same goal and then I’m just like, figure it out, sort of. I find that if we hire people who want the same thing, we don’t have to manage each other. We’re more like allies. So that’s my ideal management style is free thinking people with a shared purpose. And another set, I would say, is people make mistakes and that’s okay. I do a lot of work to preserve creativity and I don’t want to work at a place that is frantic and where I wouldn’t like to. Where I don’t like to work. I find that a forgiving place to work and an optimistic place to work. All problems are solvable. Those are kind of other two key pieces that I can contribute to as a leader to provide momentum and an interpretive framework that keeps people engaged and motivated, inspired.

Matt Bowles: I also want to get your tips on managing a distributed team for people that are building fully remote companies. Can you share a little bit of behind the scenes in terms of what your operational infrastructure looks like and how you oversee and manage a fully distributed team?

Sondre Rasch: Yes. So, a few key pieces are you got to measure outputs, not inputs. So, if you previously had an onsite company, you can’t use the input of whether people are in the office. So, your kind of just have to let that one goes and instead look at outputs. What are we getting done? Are we hitting our goals? Are we producing what we intend to? And you have to build it up like that from the ground up. And that’s what we did. Office hours, time zones are a challenge for distributed teams. Office hours is a way, you know, without going full async. First company was full async, meaning we had zero meetings. I mean full async. That is a big cost though. You know, there’s some things that Just is much better. You know, there are problems that are resolved in five minutes that can take endless slack threads to resolve otherwise.

So, some minimal meetings that I do find useful. So, we have office hours. So, you put 8 to 10am PST. That’s the hours that works for most people in the world. And we say Monday, Wednesday, Thursday, all internal meetings will be in those buckets. So outside of that, you plan your time. Internal meetings in those three, that’s the second one and then the last. I would say you got to have intentional meetings for various things that people take for granted in the onsite world. So, you have to have planned meetings for serendipity. We have this thing called lunch where people go into random groups before the weekly goals. Plan meetings for creativity. We have this thing called planning and prioritization where there’s a format for generating ideas and prioritizing them. Or plan problem solving where people bring up their problems and we literally go for a walk and everyone has to go outside for a walk while you talk in small groups about their thing. So those are some ideas. Those are some key things of making distributed teams work.

Matt Bowles: I love that man. Let me ask you this as well, about your personal productivity techniques and stress management techniques as an entrepreneur, as a CEO, how do you mitigate or manage stress and how do you organize your day and optimize your productivity to have the incredible output that you have?

Sondre Rasch: Yes. You know, some things actually have a great morning habit going these days. I get up with my wife and we go for a morning run and we stop by, we have this meditation session, we buy a coffee and then we go for a walk on the way home. And there’s this groundhog moment every day. And just this morning where there’s like Chinese couple playing this like tennis on a fence and every day, they’re like the tennis balls are stuck in the fence. It’s so weird because it’s like every day it’s like the first time it ever happened. Anyway, that’s my morning habit. And then I do meetings in the morning because, you know, it’s like European time zones. I would have preferred not to because my most productive times in the morning, but it has to be done. If I’m in Europe, then I do meetings in the afternoon much better for me. Other productivity habits I have this fantastic journal open all the time in that you have my goals, plans, journal where I kind of write when I have something to write. Not like a diary, but like when I have something to reflect on. I also take continuous notes there that I can get down everything on paper and have ways to categorize if something valuable comes out of it, like to dos and capture that immediately.

And that’s been a real great one. I would definitely recommend all of the things I just said there. Have a journal, have this unsorted text thing. Have a way to capture to do’s look at your goals and plans every day, set at the beginning of the week to write down your goals for the week. We do that with the whole company, but that was a private one I had, which we just implemented in the company, which was to write down 15 top goals. Now we say that for the week and then you choose three of them. Great way to, you know, imbue some prioritization in your daily week. In the evening to read, go for a walk-in nature every day. Yeah, because people who watch me, they’re like, how do you get anything done? Because I’m very much like in the moment a lot of the day. I think I can be productive because I’m fast, but I’m not sort of typical productive person who’s just like sitting kind of churning out work. I am fast because I have often a clear idea of where I’m going and the vision. It’s often very easy to know what’s right like, and I make that effortlessly. And that I think I’ve noticed that that helps me a lot because often, you know, where people get bogged down is based on the decisions.

Matt Bowles: And do you have any particular stress management techniques for those moments when the entrepreneurial roller coaster takes a downswing, there’s a big setback, something really major happens. How do you, as a CEO, how do you respond to that? And what sort of personal kind of stress management techniques do you have that you employ?

Sondre Rasch: So, I have this wonderful habit, which is reflection time at night. So go out on the porch and I would just like have a conversation with myself. And I often have this little thing where I just look up at stars and I just imagine seeing myself from up there. And like looking down on the planet, you could see yourself. You’re standing with a house or wherever you’re standing. And it just gives this like that perspective shift. Has this instant view of giving whatever you’re doing into perspective. Great stress management technique to give what you’re doing perspective. And that kind of visualization thing just does it every time. And then I would kind of reflect, okay, where am I physically? How old am I? What am I doing? You know, what am I doing tomorrow? And that reflection time just pulls everything down, just gets you out of the being so in your problem to being a bit out of it. I find that to be a really good one.

Matt Bowles: That’s awesome. I love that. Well, let me ask you a little bit about your future vision, because you are thinking, not just big man, you are thinking at an enormous level in terms of where you want to build things, where you want to take things. You’re talking about building a Borderless Country on the Internet. Can you take us a little bit on that path and share a little bit of your vision and what you’re up to in that realm?

Sondre Rasch: Yes. So, Safety Wing is we’re building a global social safety net, but we were also born with the idea that that would be the beginning of the first country on the Internet. Although we didn’t know exactly how it would come about, now we know a lot more of that. So, we started a little over a year ago. Now, Plumia, the associated nonprofit to Safety Wing, Lauren Rozavi was fortunate to join and like a thousand volunteers now are working on trying to figure out the ideal country on the Internet, as well as doing lots of other things like advocate for nomad visas, which has been remarkably successful and we think also can be a good springboard to potential future passport for the first country on the Internet that we intend to make.

We look into our glass ball. You know, what we see is that the Internet has solved these boundaries. We’re looking at things slightly the wrong way because technology has changed the constraints of the world, we live in. And like with every other industry that has kind of transitioned to the sort of Internet world, that’s going to happen in this realm too. It’s going to be quite a ride. And we’re trying to kind of get ahead of that with something that is very friendly and positive and pro social as well as work. Try to encourage all the governments of the nation states to like, don’t fight this. There’s a great opportunity here because we think the transition can be much more positive if people try to succeed, attracting nomads and Remote Companies as opposed to trying to outlaw them. And we see both on the possibility horizon.

Matt Bowles: That’s amazing. Can you talk a little bit more about some of the details of what you envision for Plumia? What are some of the key sort of pillars or attributes of what that will eventually entail?

Sondre Rasch: Yes, I mean, the key thing is passport, as we say, the first merch when we started safe doing was a passport. A passport, of course, is the symbol of citizenship, but it also means identity in the sort of formal meaning of the sense, not as like identifying as something, but as I am this person, right. And because I am this person across time, I can enter into agreements, for example, or contracts. And this is really key part. And you can also use that to passports, hence the name. So, making a passport that you can use in both analog realms, the two passports and the digital realm to create trust and enter into contracts on the Internet. That’s the key component of it. And we imagine people listen in the beginning will have this as their second passport and that will be a great.

I also suspect, you know, at some point maybe company registration, similar reason. Both of these things are really clumsy when you’re in Asian states like, I mean, you register your company where Delaware. I’ve never been in Delaware. That’s for some reason where Safe Twin is registered. Or other popular jurisdictions are of course Hong Kong, Estonia, et cetera, or it used to be Hong Kong, Singapore. But it’s odd. And you hire someone and you hire them as a contractor, but they’re still regular full time. It’s just no other way to do it. And then it says in that contract that there’s a legal dispute that’s done in Delaware of which neither I am or the person hired. And it’s probably not going to happen ever. This whole thing is just obsolete. We’re just trying to kind of make do with a lot of duct tape. And of course, the way it should be done is we need a global thing where people can make contracts and company registrations is on the Internet. And there is a proper way to adjudicate conflicts and clear rules that actually apply. So that’s clearly what needs to happen and that’s where we’re trying to get.

Matt Bowles: So, when you think about this over the next five years, let’s say you’ve now got staff, you’ve got volunteers, you’ve got a lot of people power and you’ve got a lot of brain power and you’ve got a lot of expertise that are putting resources into this project. When you think about sort of the roadmap for the next five years and the different pieces and benchmarks and things that need to be achieved, where do you see this going? What does that roadmap look like?

Sondre Rasch: Yes. So right now, one piece is kind of R and D. We’re trying to gather all the knowledge that have been created since we last made countries, which is a while ago, and everything we’ve learned in between to make some really good ones. That’s one we’re building the community of volunteers and founders and leaders, pioneers, you know, early citizens who are participating in that conversation. And third, and maybe one we’re spending the most time with is to try to. That thing I mentioned, I guess you could call it like lobbying. But it’s like, you know, Lauren Rozavi, who lets that she talked at the UN just like a couple of days ago about the nomad visas. And we are very active promoter of the nomad visa. The nomad visas are not a parenthesis. This is a central part of the solution, especially the way we see it, where we imagine that in the future you could make a nomad visa block.

So, you get one visa and then you kind of get a visa in a lot of countries at the same time. And encouraging these countries, we’re making this white paper for it, we’re making an index. You know, these are some of the near-term things. We’re trying to spur this positive competition between countries, you know, make sure that that dynamic gets shifted into the right direction and doesn’t get this kind of kicking and screaming, outlawing vibe, but instead get this like, oh, here’s all this opportunity for us. And because there is, you know, there’s a great opportunity to attract knowledge working nomads to your country and Remote Companies.

And if you act quickly, you can really win out in this new world. And that’s what we want a lot of people to see. So that’s what we’re doing right now. But as you look at the five-year roadmap, where does that want to end? We want to end those five years by being live with a passport. That’s the outcome of those five years. I do think it might take possibly that long though. We have a fairly realistic plan, but we do want to launch Passport that actually works in the real world and beyond. The community building, the research, the launching of the actual country. It is the big product that I want to see out of Plumia is passport 1.0.

Matt Bowles: Amazing. All right, Sandra, let me ask you one more question and then we’ll wrap this up and move into The Lightning Round. When you think back about all of the international travel and nomading that you have done, how has all of that impacted you as a person? And why do you continue to travel today? What does travel mean to you?

Sondre Rasch: Travel is exploration and I love exploration. You know, I love new ideas, discovering new people, new perspectives. And I have this need for it in a way, but I like to be on the frontier. And one way to personally be on the frontier is to travel. It Restarts my mind. Everything becomes vivid again. I’m in the same place during COVID over and over again. It’s like, when was this? Was this autumn? Oh, it was last autumn. Such a sad thing how when you live the same day over and over again, it just doesn’t stick in your memory. But like, one trip would suddenly be filled with color and life again. And it’s like I live more and live longer and then I meet people and I learn new things. And because I break up my habits and thought patterns, I suddenly see my existing life in a new light as well. And I discover solutions to problems that I was stuck in. So, travel is amazing. It keeps you alive.

Matt Bowles: That is an awesome note to end the main portion of this interview on. And at this point, Sandra, are you ready to move in to The Lightning Round?

Sondre Rasch: I’m ready.

Matt Bowles: Let’s do it. All right. What is one book that has significantly impacted you over the years you’d most recommend people check out?

Sondre Rasch: Definitely check out The Beginning of Infinity by David Deutsch, the book that really convinced me that all problems are solvable and the only thing standing between where you want to be and where you are is knowing how to.

Matt Bowles: Awesome. What is one travel hack that you use that you can recommend to people?

Sondre Rasch: I would say ride on the plane. It’s one of the few places where you can’t do anything else and all the distractions are gone. So, charge your laptop, open up the notepad, and get to writing. Whether that is your personal plans or the hardest problems or your biggest fears, or just some cool writing project you’re working on right on the plane.

Matt Bowles: Awesome. Who is one person that’s currently alive today that you’ve never met that you’d most love to have dinner with?

Sondre Rasch: One person that I find it bizarre that I’ve never met because I’ve almost met him a dozen times is Balaji Srinivasan. He’s one of the few other people in the world talking about building a country on the Internet. And for some reason I’ve never had a chance to talk with him. And there’s been this like serious unfortunate events. We’ve been booked on the same panels; we were traveling the same place multitude of times and always something has come up. So, I’ve yet to meet him. So, I got to talk with him soon.

Matt Bowles: Awesome. All right, knowing everything that you know now, if you were able to go back in time and give one piece of advice to your 18-year-old self, what would you say to 18-Year-old Sondre.

Sondre Rasch: I would say there’s no need to wait or to prepare. Just start on the dream right away. You know, I wanted to found these companies but I thought I needed to study work and it wasn’t a terrible idea. But I realized now I could have just done it directly and then I would have been seven years further along.

Matt Bowles: Awesome. All right, of all the places you have now traveled to, what are your top three favorite travel destinations you would most recommend? People check out.

Sondre Rasch: You know, Tulum, I still love it. Of course, it has growing pains, but it has a great charm and a density of remote workers and nomads and a cool vibe. Another one is, you know, the area north from like Tuscany that, you know, if you just want beauty and a good life, that area is hyped because it’s great, it’s really lovely. And then three, you know, one place that I really loved more recently is Iceland. Iceland is cool. You can stop there on the way to the U.S. from Europe. And the nature is weird. It’s an alien landscape. The people are really cool. It’s a great place to stop off and work for a bit. It’s very convenient and you get to see some weird stuff that you didn’t think existed.

Matt Bowles: Amazing. All right, what are your top three bucket list destinations? These are places you’ve never been highest on your list, you’d most love to see.

Sondre Rasch: I would love to go to Shenzhen, China. So that’s one of those cities. You know, there’s Hong Kong and then on the mainland you have Guangzhou and Shenzhen. It’s like this one of these cities that have gone from 0 to 20 million in like a couple of decades in China. When I first arrived in Silicon Valley, I met this guy. I was just so fascinated with this person’s mind. And he was this Indian who has like a child went to Shenzhen where he learned to hack mobiles and it was just his brain worked so differently. It like really reminded me of this like cyberpunk aesthetic but like in a person. And I was like, wow, I got to go to this place because this is like another world. So, I’ve always wanted to go to Shenzhen to just check out what is going on there.

Another one is embarrassingly; I haven’t traveled around Thailand yet. It’s just. I know, it’s awesome. We have so many nomad customers in Thailand, obviously in Chiang Mai and other kind of Thailand cities. Everyone who’s been there says it’s fantastic. I just haven’t been yet. Gotta gets going. And then lastly is my co-founder. He went and lived in Buenos Aires for a while, and he totally changed his personality to be, like, Argentinian. And this is a dramatic change. Suddenly he was, like, going out, drinking wine and dancing salsa in the evenings. And to be clear, this is the person who typically, like, watches football and drinks beer. And I was like, what is with that city? So, I really want to go and live in Buenos Aires for a while.

Matt Bowles: That’s amazing, man. Yeah, I was just down in Buenos Aires in December. Actually, pretty recently, they had a conference down there I was speaking at called the Nomads BA Conference. And sort of in line with some of the stuff you were just talking about. The city of Buenos Aires is trying to attract digital nomads to come down and use Buenos Aires as a nomad hub. And so, they sponsored a conference and brought a bunch of us down there to speak. And it’s a pretty amazing place I’ve been a few times. It was actually the place where I started my Nomad journey back in 2013.

Sondre Rasch: Oh, really? Yeah.

Matt Bowles: It was literally the first city I went to for three months after I gave up my primary residence and started my nomad journey. So, a lot of good memories from there. So, when you’re ready to plan that trip, hit me up and I’ll give you some tips.

Sondre Rasch: Thanks, man. I’ll definitely show up when that visit comes along.

Matt Bowles: Awesome. All right, Sandre, I want you to let folks know at this point how they can find you, follow you on social media, learn more about Safety Wing, learn more about Plumia. Maybe they want to volunteer, get involved, or at least follow the progress. How do you want people to come into your world?

Sondre Rasch: Yes. So definitely go to safetywing.com if you’re nomad or have remote teams. We’re hiring a lot. Definitely check that out if that’s relevant and you’re looking for a cool remote job. And secondly, we have a podcast, buildingremotely.com and a project to kind of like make a textbook for starting remote startups. So, if you’re doing that, definitely pay attention to buildingremotely.com and Plumia. Plumia Country. We’re onboarding the pioneer citizens. We have some exciting projects along the way and remarkable traction on that project. So, if we succeed, that’s one of the big projects of this generation. So that will be looked back to and you have the possibility to be a founding citizen pioneer. Go to Plumia Country to do that.

Matt Bowles: Awesome. We are going to link up all of that in the show notes so folks can just go to one place at themaverickshow.com and there you’re going to find links to all of the things that we discussed on this episode and how to connect with Safety Wing and Plumia and Sondra and all of that. So just go to themaverickshow.com, go to the show notes for this episode and there you will find it all. Sandra, this was amazing, brother. Thank you for coming on the show.

Sondre Rasch: Thank you. It’s been a fantastic conversation. Thank you so much.

Matt Bowles: All right, good night, everybody.