Joey Flores | The First Country on the Internet

Timothy Allen: I think what you do is very relevant to our listenership and our crowd. But you were talking about basically creating a system which travels with you. Is that right?

Joey Flores: Yes. We’re effectively building a new social safety net, which generally would include things like healthcare, income protection and retirement. If you think about social security and things like that, these systems are generally provided by people’s countries. But when you become a global citizen and start living a more borderless life, they don’t always follow you beyond the borders of your home country. So we are building a social safety net that is global, and ultimately our plan is to launch the first country on the internet, which will allow people to become membership-based citizens and have that safety net follow them everywhere they go.

Timothy Allen: Right. That’s a big ask, a country on the internet. Obviously, you know about The Network State.

Joey Flores: Yes.

Timothy Allen: Right. When we talk about countries on the internet, we tend to think of The Network State. Same idea, probably a completely different modus operandi. Network states amass people online and then hope to create something in the real world. You’re talking about creating a bunch of services, but really also a country. Or is that just a term to group all your clientele together? How would it work?

Joey Flores: I wouldn’t say they’re two separate visions. They’re all one cohesive vision. We have a nonprofit division called Plumia, which is the one working towards building a country on the internet. Lauren from our team, who runs Plumia, has spoken at the United Nations. We take that vision very seriously. SafetyWing is building the social-safety-net infrastructure to support the citizens of that country, but only for as long as the country feels SafetyWing is doing a good job would it be required to continue working with SafetyWing. If there is another aspect of the safety net that it feels some other company would be better able to provide, the country would be at liberty to make those decisions on its own. It would be a membership-based citizenship. We’re looking to have our own passport. We’re definitely aiming to be the first country on the internet.

Timothy Allen: At what point would you consider yourselves a country? Is it acknowledgement by the United Nations or other diplomatic relations? What would it be?

Joey Flores: We talk about that quite a lot. I think one of the major benchmarks would be having our own passport recognised by certain countries. Right now, our most recent consumer product, called Nomad Citizen, is a membership-based product. It comes with income protection, healthcare, life insurance and many other things. It also includes visa assistance. Right now, we’re tapping into existing digital-nomad visas and making it very easy to apply for them. If you want a digital-nomad visa in Thailand, you may have to fill out an application in Thai. Then you want to go to Spain on its digital-nomad visa and have to fill out another one with completely different requirements. We’re connecting our back end to those systems so that you can apply for digital-nomad visas through us. I think that will progress into us having our own passport, which is recognised and allows you to go to different countries. Those countries would welcome you because they know that, if you have the SafetyWing passport, you’re bringing your own social safety net. You’re not going to rely on their healthcare or income protection. One of the things countries are sceptical about when they welcome long-term travellers is whether they will become a drain on the economy. We talk about paying taxes into the places you go, so those countries would welcome you and feel you are a responsible citizen arriving with your own safety net, making sure you are not a drain on the local economy or tax base.

Timothy Allen: Would you at that point have two passports? Would they expect to see your home passport as well, or are you thinking you would just have a Plumia passport?

Joey Flores: Essentially, yes, it would be a Plumia passport. I think there will be a progression. At first, you might need your normal passport, but having the Plumia membership and an ID would make them recognise that you’ve got the safety net which makes you a desirable visitor or new resident. Eventually, the idea is that you would have a SafetyWing passport and that passport would be sufficient to get you into places.

Timothy Allen: How far down the road is that? You’re not Plumia yourself. Plumia is separate from SafetyWing, right?

Joey Flores: Yes.

Timothy Allen: SafetyWing is the insurance and social side of it. Is that right?

Joey Flores: Yes. We are providing the social-safety-net infrastructure to keep the citizens happy, healthy and safe. Plumia is more of the, I wouldn’t say lobbying arm, but the nonprofit organisation leading this narrative. It’s very involved in things like Edge City.

Timothy Allen: Wait a minute. I’ve heard of Edge City, but I don’t know what it is. What is Edge City?

Joey Flores: It’s a one-month pop-up city where network states are discussed extensively, along with lots of other things. I’m not really an Edge City expert, but it’s a pop-up city which is very aligned with network-state thinking.

Timothy Allen: Okay. So part of your social safety net would be income insurance, would it?

Joey Flores: Yes.

Timothy Allen: Insurance in the ordinary sense as well, such as crashing your car or going to hospital? Is it all based around insurance?

Joey Flores: It’s not all insurance. The most important aspects of our current product, Nomad Citizen, which is the closest thing we have to the full social safety net, include health insurance. I have Nomad Citizen insurance. It’s incredible insurance, the best I’ve ever had. It also has income protection. You have to pay into it for two years, although we’re trying to shorten that timeline. Once you have, if you lose 90 per cent or more of your income, it doesn’t matter whether you’re a business owner, freelancer or contractor, if you can demonstrate that loss, we will pay you $4,000 a month for half a year while you get back on your feet. That’s more than double what I would get from the state of California, so it’s a very good plan. We have life insurance and permanent-disability insurance, which could cover you for many years if you became permanently disabled. It covers repatriation if you pass away abroad and your body needs to be taken back to the United States. It has evacuation insurance. So it has all of those things, but we also recently launched visa assistance covering the application process for about eight digital-nomad visas worldwide, and we’ll be expanding those. We offer community tools too. We’re hosting dinners in different countries, talking to digital nomads and finding out what’s important to them. Those dinners and community events are starting to shape the direction the product takes.

Timothy Allen: So you join, travel wherever the hell you want and all these things apply in whichever country you’re in? Whenever I renew my travel insurance, it’s always a list of: do you want this, do you want that, do you want America? Obviously, that adds a massive amount to your premium. Is it the same with you, or do you join and then forget about it, knowing you can travel the world and everything should be covered?

Joey Flores: Generally, yes. The exception is that, to be honest, I don’t know about Nomad Citizen specifically, but with our base travel and medical insurance you need an add-on for the US, Singapore and Hong Kong because they are so expensive. Everything else is included. Those plans also have an adventure-sports add-on for very active people doing more dangerous activities which would not normally be covered. So there are a couple of add-ons, but for the general person they aren’t really necessary. You’re pretty much covered. Nomad Citizen is more comprehensive. I can’t remember whether there are restrictions for the United States. I live in Mexico right now, and when I go back to the US to visit my family, I have coverage for a certain period without needing an add-on.

Timothy Allen: That’s the problem I’ve got. This is a six-week trip for me, and normally my current insurance says four weeks and then you have to return to your home base. I travel a lot, and what annoys me is the amount of time I have to spend dealing with things like this. It would be great if there were just an option to click a button, know I’m covered and even spend six months in the UK while still being covered there, despite it being my home country.

Joey Flores: We have three plans on the consumer side. Nomad Essential is basically emergency medical and travel insurance for a broken arm, a sudden illness or something like that. Nomad Complete is more of a traditional healthcare policy, and that policy does work in your home country. These things can be different for US citizens, but generally speaking, in most countries Nomad Complete would cover you even when you go back to your home country. Nomad Citizen is the most robust package we have.

Timothy Allen: And the passport and Plumia side of it: have you any idea how far down the road towards that kind of sovereignty you or Plumia are?

Joey Flores: We take a very long view on a lot of this. I think we’ll make a great deal of progress. As we discussed, perhaps the passport won’t get you into a country in the next ten years, but it might be the identification you need, in addition to your existing passport, to be welcomed into a country. We tend to look at this vision on about a 25-year timeline. We just had a company town-hall meeting and talked a lot about the vision. We’re mapping it out to 2050.

Timothy Allen: Okay, 2050. Is it fair to say that by 2050 you expect to have a recognised passport?

Joey Flores: I’m putting a flag in the ground by saying that for sure, but we’re an ambitious company. We always aim for the ideal and try to work out how to do things. Yes, I would say that’s the plan.

Timothy Allen: Make some predictions for me about the remote-work world as well. There are a lot of people here concerned with remote work. What do you see in the current state of remote work and its future? Is it growing or shrinking?

Joey Flores: I think it’s growing. You hear some bubbles talking about the return to the office, but remote work continues to grow. When you think about issues happening in the world, look at people in countries neighbouring Iran who are affected by conflict and don’t want to be in those places. Think about water shortages starting to happen in different places. Mobility is going to become increasingly important to a larger group of people, and remote jobs are the easiest way to give you the flexibility to move. More jobs are being born out of the information age and can be done from anywhere. I don’t think many people would argue that there will be less remote work in the future. I’ve got a friend developing a plane which can get you from any city to any other city in the world in under two hours. It’s a Mach 10 passenger plane. They’re looking at about a six-year timeline to start flying passengers around the world in less than two hours, from somewhere like New York to Tokyo.

Timothy Allen: What? Hold on a minute. Two hours from New York to Tokyo?

Joey Flores: Yes.

Timothy Allen: In a private jet? For billionaires? What’s going on?

Joey Flores: No. They’re developing a plane that can take off from any normal airport. It will carry about 200 people, and they’re trying to make it cost about the same as a business-class ticket. They’re going to start with cargo and a Mach 5 plane, then work towards Mach 10.

Timothy Allen: That sounds ridiculous.

Joey Flores: They have 12 people right now. Eight of them are PhDs, and the founder formerly worked at NASA.

Timothy Allen: He’s not here by any chance, is he?

Joey Flores: No, he’s not. I went through Y Combinator, and he’s a friend of mine who also went through Y Combinator with his previous company. They’re already doing wind-tunnel testing on prototypes.

Timothy Allen: You’d better explain what Y Combinator is. Not everyone knows. It’s a San Francisco thing, right?

Joey Flores: Y Combinator is probably the most prestigious early-stage funding programme for entrepreneurs building ambitious, billion-dollar unicorn start-ups. It’s usually the first money into a company. It has been the catalyst behind Airbnb, Dropbox and many of the biggest and best companies you’ve heard of. They were originally funded by YC. It’s also a tight-knit community, so I know quite a lot of founders because I went through the programme myself. My friend’s company is called Stratos Industries. He went through YC previously, but with this company it doesn’t make quite as much sense to do it again. When technologies like that emerge, people will start working in other places. The world is shrinking in terms of how difficult it is to get from one place to another. Even people who normally work in an office are going to spend more time working remotely once they can fly to Japan in two hours.

Timothy Allen: You live in Mexico, did I hear you say?

Joey Flores: Yes.

Timothy Allen: Why? You’re from the US?

Joey Flores: I’m from California.

Timothy Allen: Right.

Joey Flores: I increasingly spend a lot of time in Mexico. I really love it there. In my spare time I create art, and I live in Oaxaca. It’s a cultural epicentre in Mexico. The art scene is amazing. There are so many galleries, murals and artisans of all kinds.

Timothy Allen: The reason I asked is that you’re basically a remote worker as well. I was interested in why the inclination to live in Mexico came about. Obviously, tax and standard of living are factors too.

Joey Flores: I’m on an American salary. I’m about to move into a very nice apartment which would probably cost about $10,000 a month in Los Angeles, and I’m going to pay $1,300. It’s close enough for me to visit my family in California once a quarter. There are other places in the world I might like to live, but I want to be close to my family. Mexico is a great place to do that while enjoying a very high quality of life on a budget.

Timothy Allen: Do you think it’s possible to create a Silicon Valley-type experience somewhere else, perhaps where you are in Oaxaca or elsewhere in the world? How do you do that? If someone says they want to start a business, they’re almost certainly going to say they will try San Francisco first. How do you start that somewhere else? What does it take to amass enough people in one place to create the kind of start-up environment you get in San Francisco, but in a completely new location?

Joey Flores: I think there are two core things that make San Francisco an amazing place to start a company: access to talent and access to funding. There are other cities in the world where talent is plentiful. Mexico City has an amazing start-up community. I’ve been an entrepreneur a couple of times and mostly built my companies out of Los Angeles. Even there, the funding scene and requirements are very different. Investors tend to be a little more risk-averse. They’re more focused on the business model, unit economics and whether you are generating revenue today. In San Francisco, investors are willing to take a very big leap very early on companies which could be massive but are still moonshot ideas with very little traction. They do look for traction, but they’re willing to take risks to create unicorn companies. Talk to a founder in Indiana and that isn’t their experience. People ask when they’re going to be profitable, and they’re saying, ‘I’m trying to build the next Instagram. Instagram probably took years to become profitable.’ You can solve the talent issue in a number of cities around the world, but until investors in those places are willing to take bigger risks, you aren’t going to get another Silicon Valley.

Timothy Allen: How does that happen, though? On this podcast, we’re very interested in new places and jurisdictions, especially those with a slightly different regulatory environment. Austin is a good example because it’s outcompeting a lot of other places in the US. It’s drawing talent from everywhere. There’s a specific set of ingredients behind why that’s working, I imagine. I’ve only been here a few days, but I really like what’s going on. How do you rectify the funding problem and create a San Francisco-type environment somewhere like Mexico?

Joey Flores: When I talk about access to funding, I’m generally talking about very early-stage funding. Once you have a certain level of traction, it’s easier to raise money from people who aren’t in your local region. At an early stage, you often want angel-investor money, and angels like to be close to the investments they make. The easiest way to produce more angel investors is to create more millionaires, and often the way to do that is through strong liquidity events for existing companies. As Austin has larger companies which go public or get bought, perhaps 75 people from the earliest days of one company become multimillionaires. Many of those people become angel investors. Strong exits and unicorn companies breed more angel investors, and angel investors create early-stage capital. That’s one way a city can quickly become a good place to raise early-stage capital: have an exit from a larger company which creates a lot of local millionaires.

Timothy Allen: Do you think lifestyle reasons and a better standard of living are enough to attract those people? You moved to Mexico for a specific reason.

Joey Flores: Absolutely, increasingly. Oaxaca, where I live, isn’t somewhere I moved to in order to build a start-up. If I were going to build another one, I would go to Mexico City. Oaxaca is an amazing place to live, but it isn’t going to become another Silicon Valley, and I wouldn’t want that for Oaxaca anyway. I know a number of founders from the Y Combinator network who are based in Mexico City. Their companies have the opportunity to become very big. If they create a lot of local millionaires there, it will continue to become an easier place to start companies.

Timothy Allen: Oaxaca is roughly in the middle of Mexico, isn’t it?

Joey Flores: It’s very far south. It’s the second-most-southern state in Mexico, about eight hours south-east of Mexico City.

Timothy Allen: What’s the big town there?

Joey Flores: I live in Oaxaca City, which is the state capital and its biggest city.

Timothy Allen: And the coastal region is there too? Puerto Escondido?

Joey Flores: Puerto Escondido is the popular beach.

Timothy Allen: That’s right. It’s a very big digital-nomad hub, a Bali-esque type of hub, isn’t it?

Joey Flores: It’s probably not as big as Bali, but for Mexico it’s very similar. People go there to be digital nomads. They have Starlink in lots of places. People go there when they want to build a company while surfing and doing yoga retreats.

Timothy Allen: What’s your view of the digital-nomad scene in general? You seem deeply embedded in it through your business. Is everything good in the digital-nomad world?

Joey Flores: I think it’s getting easier and better for digital nomads. As somebody who spends a lot of time in places like Oaxaca, I hope digital nomads take a little more care with how they approach the cities where they live. I have many local friends in Mexico. When I ask how they feel about people coming there, they say, ‘For many years we fought to increase tourism here, but what’s happening now isn’t tourism. People are coming and staying.’ Take me as an example. I arrive with an American salary and I’m happy to pay $1,300 for a really nice apartment. People start upgrading apartments and pricing them at levels which only people from richer economies can pay. That creates housing problems for locals who don’t earn those salaries. I come from America, where we tip, so I tip my cab driver and waiter 20 per cent. That isn’t normal in Mexico. You might think that’s a nice thing to do and that you’re helping the waiter, but then waiters start paying more attention to foreigners than locals. Locals no longer receive the same level of service. A taxi driver might pass three people from Oaxaca to pick up the tourist 15 feet behind them because they think that person will probably tip. We need to be careful about that dynamic. If people become more aware of these effects, digital nomads can be a great way to boost local economies, but it has to be done responsibly.

Timothy Allen: Do you think digital-nomad culture is still growing, or has it topped out? One solution to the problem you describe is for people to embed themselves in society long-term. One reason people find it easy to be annoyed by digital nomads is that they do what you just described, stay a few months and then leave a footprint behind. If you embed yourself deeply and stay, perhaps there is less animosity. Prices may still rise, but at least you’re eating out constantly and continuing to add to the economy. One of the things people find disconcerting about nomads is that they come and then they go.

Joey Flores: I think it comes down to how you behave in these places. Make your best effort to learn some of the language. A friend and I live down there, and we take a lot of care in the way we act. We have many local friends. We love getting to know the culture. We’re always buying work from local artisans and genuinely supporting the economy. There are a few weekends which are major events and attract many tourists. You watch people doing things and think, ‘I wish they would act a little more responsibly and not be such conspicuous foreigners.’ Try to understand the place you’re in and appreciate its culture. Don’t try to bring your culture down there. The term ‘nomad’ is fine, but I think it’s becoming a little like the term ‘influencer’. That doesn’t mean I dislike content creators. I follow many of them, but people associate ‘influencer’ with someone obnoxiously taking photos where they shouldn’t. A little of that is happening to the term ‘nomadism’. We talk to many digital nomads, expats and families who have moved to another country, and increasingly they don’t attach the nomad label to themselves. Our product Nomad Complete is designed more for people who want a real healthcare plan, not just emergency medical coverage. It includes preventative care and everything else. When we speak to those people, the word ‘nomad’ signals instability and they don’t feel it describes them. They’re staying somewhere long-term and probably identify more with ‘expat’ or ‘resident’. That shift has come partly because digital nomads can arrive in a place and change how it feels and looks in ways local communities don’t appreciate.

Timothy Allen: Do you think there is a digital-nomad culture? Here’s my interpretation. Bali would be a good example: lots of good and healthy places to eat, opportunities to do healthy things, a nice environment and co-working spaces. Is that nomad culture? I travelled around Bali in the 1980s and haven’t been back for a long time. I almost certainly wouldn’t recognise the place. You could argue: did Bali ask to be turned into that? I’m not trying to piss on anyone’s grave, but I’m sure some people think that way. Is there such a thing as nomad culture, and is it a good thing?

Joey Flores: It depends how you define culture. The things you mentioned are what make a city a good hub for nomads. But to me, nomad culture is entrepreneurship, exploration and freedom. Those are the pillars of nomadism: the ability to roam, to find a place which feels like home, to explore places and learn about other cultures. Digital nomads are very inquisitive people. They appreciate learning about other parts of the world. Good Wi-Fi, good housing and those other things make a place inviting, but nomad culture is about pursuing your dreams and ambitions wherever they take you. I think it’s lovely. I was relatively nomadic for ten years and met incredible people. They’re building things and creating the lives they want for themselves. Those are beautiful things. There are places which make that very enjoyable. Bali is amazing. I’ve been there, the food is insane, and if you’re a surfer it’s great fun. We’re actually running a creator residency right now and are about to extend the deadline for another two weeks. We’re looking for a creator who will explore what might be the next wave of nomad hubs. They’re supposed to pick three cities which aren’t Bali or Lisbon, go there, check the Wi-Fi and co-working spaces, document the experience and start figuring out where the next hub will be.

Timothy Allen: That’s interesting. When will it happen, and do applicants have any ideas about where they’re going yet?

Joey Flores: We’ve been accepting applications for almost a month and we’re going to extend the deadline by two weeks. We’ve had amazing proposals. Some interesting cities have appeared repeatedly. I had never heard of Florianópolis in Brazil, but lots of people suggested it. I thought, ‘I’m going to buy some real estate in Florianópolis because apparently they know something I don’t.’

Timothy Allen: Florianópolis is a very interesting place. I recently did a two-hour interview in Honduras with a woman who’s part of a project there called Ipê City. It’s fascinating. It was built in the 1950s almost as a private city, although without a border around it. It’s a very well-loved place among Brazilians too, the kind of place a Brazilian might aspire to retire to. There’s a lot of interesting stuff going on there. Were there any other places around the world which made you think, ‘That sounds good’?

Joey Flores: I was only on one call where we briefly browsed the applications and saw what people had proposed. Florianópolis was the one that stood out because I had never heard of it and saw it four or five times in different people’s suggestions. I saw Oaxaca and thought, ‘Let’s not pick that person. I don’t want more digital nomads in Oaxaca.’ I’m kidding. There are definitely trends in the proposals, and I find it interesting that people already seem to know where the next hubs might be.

Timothy Allen: Final question, since we’re at the Running Remote conference: what is the future of work?

Joey Flores: The future of work is definitely global. We were interviewing our founders about why they decided to build a remote company. First, they weren’t in the same place themselves when they started SafetyWing, so it wasn’t even a decision which needed to be made. It was remote from day one. When we interviewed a few founders about remote culture, one thing they all said was that a main driver is access to the best talent around the world. Even if you’re in New York, which seems like a large talent pool, at the end of the day it’s still just the people in New York. We have people in more than 45 countries and no offices. The calibre of the people I work with is unbelievable because the whole world is literally our hiring pool. That’s a compelling sales pitch for being a remote and global company.

Timothy Allen: Do you ever meet physically as a company?

Joey Flores: Yes. SafetyWing invests a great deal in its culture, and I’m very grateful for it. I’ve only been at the company for eight months. In November, they took us to Patagonia and rented an entire hotel on a lake overlooking the mountains for six days. They catered every meal. We went rafting down the river one day, but spent a lot of time planning for 2026 and talking about the mission. We had a talent show and did all kinds of things. In two months, at the end of June, we’ll go to Norway for what we call Build Week. We form teams. I’ve put together a team of four people to work on a specific project leading up to it, and Build Week is the climax where you come together and try to finish it. We’ve broken into nine or ten teams, each with an ambitious thing they want to accomplish which would be much better worked on in person. The company has rented the whole hotel again. Probably 60 to 70 members of our team will go and work there. We also do ad hoc gatherings. If you feel you’re doing something interesting with your team and it would help to work together, you can submit a request and the company might fly everyone to one location for four days so you can work feverishly together.

Timothy Allen: You’re making me jealous. I work with a fully remote team. We have a yearly gathering. The time before last it was at a firing range, and the last one was at a casino.

Joey Flores: I think that’s normal for most companies. SafetyWing is special in this regard, but it pays for itself. We had a very stressful project just before one gathering, and the way the gathering reset and reunited everybody was powerful. It’s played out to call a company a family, and our founders don’t really like it, but I had joined in August and then went to Argentina in November. I thought, ‘I’ve found my people.’ It wasn’t just work. We were hanging out and getting to know one another. People were DJing at night in the recreation room. It creates cohesion. Our retention rate is through the roof. People love working at SafetyWing. Those investments pay off in big ways.

Timothy Allen: I don’t know much about this because I’ve never worked in that kind of structure, but I remember when Facebook, Google and similar companies were starting. We saw games in the office and all those perks for the first time. This sounds like a newer version of that model. Instead of Google creating free food and a playground at work, an upwardly mobile remote company does these incredible trips. Is that fair?

Joey Flores: Not only that, but we have a home-office stipend every year. I think it’s $500, which you can invest in your home office. I bought a new desk and chair. Every year you have money to upgrade your working situation at home. We have a houseplant stipend too. If you buy houseplants, take a picture and submit it to finance, they’ll reimburse you because we feel it makes your living situation better and healthier. The company has some interesting ways of doing this. We’re replicating the games and pleasant things you might have at an office, but letting you do it at home and making the financial investment there.

Timothy Allen: Have you got any Japanese employees? Imagine if they bought bonsai trees for their home office. Some of those are very expensive.

Joey Flores: Apparently the houseplant stipend used to be uncapped. Then an employee bought about $3,000 worth of houseplants and they thought, ‘Oops.’ So now there’s a cap, although I don’t know what it is. I’ve only bought one houseplant with my stipend. We also have a personal-development budget for every employee. If you want to take a class, join a gym or hire a personal trainer, anything which will make you a happier, healthier or better employee, you can invest your personal-development budget in it.

Timothy Allen: One last thing I should mention before we go: AI. What is AI doing to your company, your work, the way you operate and where you’re going in the future?

Joey Flores: The obvious answer is that it’s increasing the output of every team member. When AI tools first became big, I was running my own company in the fine-art space. It was slow-moving and not mass market, so I wasn’t using the tools in the same way. When I joined SafetyWing and a couple of other projects last year and really started using them, I thought, ‘The work I just did this month would have taken me five months in the past.’ The output of our whole team is getting much greater. We’re also going to use AI to make claims processing faster. It can let people know immediately if they haven’t submitted sufficient documentation for a claim, rather than waiting four days for a team member to review it and ask for another document. AI will look at the documentation immediately and say, ‘We’re going to need one more document from you.’ We’re using AI internally to make every employee better, but also in systems which will make the customer experience much faster and more efficient.

Timothy Allen: What do you think about the idea that a lot of us will be out of jobs in the next ten years?

Joey Flores: I think there will be a shift towards solopreneurs. There’s no question that it will be tough for graphic artists and many other people. I had an argument with someone about this. Several years ago, I tried to create a children’s book and spent time in Facebook groups watching how the process worked. He said AI was going to destroy the illustrator’s job. That’s true, and I feel for illustrators, but there were many people in those forums trying to create books who were schoolteachers. They had seen something among their students and wanted to get a beneficial message out to children, but on a teacher’s salary they couldn’t afford to pay $100 a page for illustrations, which was the going rate for a decent illustrator. Their books would never see the light of day, despite being beautiful stories. The illustrator might lose work, but another person will be able to create a children’s book which could never have existed without AI. There will be a shift. Many people will be able to do things they couldn’t do before, and some people will have to adapt. It isn’t just graphic designers. I use AI to review legal contracts. It’s going to affect lawyers. I don’t think my job is insulated from what AI will be able to do. I’ve heard the line many times that AI isn’t going to replace people; people who know how to use AI will replace people who don’t. I use AI all the time, but it’s my 25 years of marketing experience which helps me get the right result. It isn’t yet at the point where I can say, ‘Create a marketing plan for SafetyWing for the next 12 months,’ and receive something usable. I have to push back, say what won’t work and know what to ask for.

Timothy Allen: What would someone without 25 years of marketing experience do to get into a job like yours? I agree that your experience gives you the know-how to use specific tools in a specific way which AI doesn’t yet understand. It doesn’t have your macro view, but it knows how to do all the little bits and pieces. How does someone starting out get in when their entry-level job is what AI is already doing?

Joey Flores: The best thing they can do is use AI as a teacher. I use it to teach me Spanish. There are all kinds of apps, but I can tell AI the exact experience I want and the things I want to improve. Most Spanish-language apps focus on vocabulary and formal grammar, but I’m in Oaxaca, where people use slang which the big apps don’t teach. I’ve asked ChatGPT to help me learn Spanish in that specific way. We do role-playing and it tells me there is a more natural way to say something. If somebody wants to become an amazing marketer, they can lean into the educational side of AI. Ask it to do a deep-research project on ten incredible, unorthodox start-up marketing campaigns from the past five years which produced outsized results. Then study them and ask more questions. The other thing anyone can do is use these tools to build something which demonstrates their own marketing capabilities. When I’m interviewing a candidate, it’s fine if they say they have experience doing something. But if they say, ‘I built an Instagram account last summer, grew it to 15,000 followers and here’s how I optimised it,’ and they used AI to understand how to optimise and create the content, I see a go-getter and think this is somebody I might want on my team.

Timothy Allen: Could you hypothesise about this, because I’m thinking specifically of my own children? My oldest is 14 and she’s growing up in this world. I’m thinking it may not be worth going to university. Perhaps it would be better to spend that time building something. By the time you’re sitting in front of a potential employer, they may be less concerned about your degree than what you’ve actually done. If you can use AI to create something interesting, that’s a much better way to market yourself than getting a bachelor’s degree in business studies or something similar.

Joey Flores: You’re going to get a very biased answer from me. I dropped out of high school when I was 16 and didn’t go to university. A few weeks ago I was talking to our CEO and mentioned it. He said, ‘I didn’t know you never graduated from high school. I didn’t look at your résumé.’ I like that about SafetyWing. They looked at what I’ve done and accomplished and didn’t care about the degree. I think that will become more common. There was a period when not graduating from high school was fine because people looked at your résumé, saw your experience and didn’t care that there was no education section. They saw I had been director of business development at a company and all the other things I had done. Once people started using technology to filter résumés, they would add ‘minimum requirement: bachelor’s degree’, thinking there was no harm in filtering out people who didn’t have one. What I found was that I suddenly stopped getting interviews because applicant-tracking systems were excluding me before the hiring manager ever saw someone like me. I hope we move beyond that and train AI to look for what a person has done rather than which credentials they have. I also think people will increasingly be able to educate themselves using modern tools. It takes the education system a long time to catch up with technology. Interview somebody with a marketing degree from a four-year or even six-year college and they’re often learning marketing tactics from four, five or six years ago. Somebody who builds a project at home and takes it to 10,000 followers on Instagram probably knows more about marketing than a typical MBA in marketing.

Timothy Allen: What about actually getting a job? Would you apply for lots of jobs, or try to meet people at conferences, tap them on the shoulder and introduce yourself? What would work best with you personally?

Joey Flores: The best way for anybody to get a job is to stand out. Meeting somebody in person and talking to them is a great way to do that. I don’t think merely submitting an application is very effective. Track down the hiring manager or founder and say, ‘I built this thing and I’m really interested in your job.’ Show me something special or different. Get aggressive and try to stand out. We hired for a job recently. One person interviewed well, seemed competent and completed the test task. But another person went far beyond what we asked, and we thought, ‘That is incredible.’ It’s very competitive. Anybody who thinks they can simply submit an application and do an interview isn’t going to be picked over somebody who goes the extra mile, gets aggressive, reaches out to four or five employees and asks, ‘How do I thrive at your company?’ They genuinely find out what will help them stand out. It is tough out there and I don’t want to downplay that, but most people are doing the basics. The people who try to stand out are the ones who will get the job.

Timothy Allen: Joey, many thanks. Thanks for letting me tap your brain. That was good. I’m always interested in how to advise my own children because the world is changing so rapidly that it’s overwhelming. I’ve only ever worked for myself. I’ve only ever had my own companies, or things like this where I do my own thing. It’s easy to get a job doing that because you just give it to yourself. But I couldn’t necessarily advise my kids to do that.

Joey Flores: It’s very stressful. You have to be a certain type of person. I built two start-ups myself and drove one to acquisition. I’m not going to lie: I have scars from that experience. It’s very hard.

Timothy Allen: How do you find working in what you might now call a corporate structure, going from your own company to working for somebody else? I don’t think I’d be able to work for anyone else in that sense. I like people and listening to them, but I don’t like them telling me how to run my company.

Joey Flores: I felt exactly the same way and would probably agree that I wouldn’t fit well in most companies after many years of entrepreneurship and being a founder. It’s very difficult to take orders you don’t believe in, follow a strategy you don’t quite buy into or simply defer to the founder. SafetyWing is a very different kind of company, and I feel fortunate to have landed there. One of our values is ‘let the best idea win’. Sometimes that means the founder’s idea isn’t the one which wins the day. SafetyWing has about 60 employees and does tens of millions of dollars in revenue, yet sometimes it’s almost too start-up-like even for me. I think, ‘We’re too big to behave this way in some respects.’ I feel as though I’ve found my home, but I know it’s very unusual. Working at somewhere like Google would not work for me. Many corporations hire specialists. After being a founder, I’m a supreme generalist. I’ve done all kinds of things and need to be somewhere that values that and wants me to go where the ball is and where the greatest impact can be made. I don’t want to be siloed doing one thing, which is what tends to happen in bigger corporations.

Timothy Allen: Do you find that’s a common experience in the remote-work scene? Is it a good place for people like that to work? I looked at the speaker list here and didn’t recognise a single name, but if you’re in this world you probably know all these people. Is part of remote-work culture choosing people through interviews which are more rounded and less narrowly focused on their past, and creating work environments like the one you describe?

Joey Flores: A natively remote company is likely to be more flexible not only about where and when you work, but also about the kind of people it hires. To be a good remote worker, you have to be a self-starter. Nobody is watching over your shoulder, or at least I hope not. I see some productivity tools at this conference which track time, and I don’t know how I would respond to that. Measuring people by their output rather than their logged time is a better way to make sure they’re doing great things. A typical remote company is probably more forward-thinking. Being a contractor also gives you the freedom to pick and choose your clients, which helps you make sure your values and lifestyle align with the people you’re working for. It isn’t always easy to say, ‘This doesn’t feel aligned, so I’m going to drop this client.’ You need another client waiting in the wings. But the remote ecosystem is probably a nicer place for someone who is very independent and self-driven. Other aspects of those companies and their cultures are also likely to feel more aligned with those people.

Timothy Allen: Lovely. You heard it here first. If you’re that kind of person, go to a remote-work company. Joey, many thanks for speaking to me. I really enjoyed this. You’re a wealth of information. Thank you very much.

Joey Flores: I appreciate it. Thanks a lot.

Notes

This transcript was reconstructed from the raw timestamped video episode text. The opening “Coming Up” montage, chapter labels, Veritas Villages sponsor read and closing music were removed. The transcript above starts at the beginning of the conversation, around 0:00:59 in the video-timing transcript, and ends at the close of the conversation, around 0:52:48.

Speaker names were added and formatted in bold. The source transcript did not include reliable speaker diarisation, so speaker turns were inferred from the flow of the conversation, context, questions, interruptions and repeated references. Short interjections and overlapping speech were lightly consolidated where doing so improved readability.

Timestamps, filler words, repeated false starts and obvious transcription artefacts were removed or lightly normalised. The conversational tone, meaning, jokes, scepticism and main order of the exchange were preserved.

Proper nouns and likely ASR errors were corrected where possible. The main corrections and normalisations include: Joey Flores; SafetyWing; Plumia; Nomad Citizen; Nomad Essential; Nomad Complete; The Network State; Edge City; Y Combinator; YC; Stratos Industries; Oaxaca; Oaxaca City; Puerto Escondido; Mexico City; Florianópolis; Ipê City; Running Remote; Patagonia; ChatGPT; and SafetyWing’s Build Week.

A few names, figures and phrases remain context-dependent and should be checked against the audio before publication, especially the exact company name “Stratos Industries”; the Mach 5 and Mach 10 aircraft claims and timetable; the precise Plumia passport timeline; product coverage, waiting periods and benefit figures; the number of countries and employees mentioned; and the exact home-office, houseplant and personal-development stipend amounts.

No independent fact-check has been applied to claims made by either speaker beyond checking spellings and likely identities of proper nouns. Insurance, healthcare, visa, passport, employment, technology and company claims should be treated as speaker claims, not editorial assertions. Current product terms and legal or financial implications should be checked directly with the relevant provider or qualified professional.