A Country on the Internet, a Passport by 2050, and the Death of the CV

- Joey Flores is Head of Marketing at SafetyWing, the Y Combinator-backed company building a global social safety net for remote workers. A two-time startup founder whose YC-funded music startup was acquired, he dropped out of high school at sixteen and now lives in Oaxaca, Mexico.

Timothy Allen sits down with Joey at the Running Remote conference in Austin, Texas, for a conversation about building for the 21st century nomadic life. SafetyWing's pitch is simple and audacious: your healthcare, income protection and pension come from your country and stop following you the moment you live a borderless life, so they are building a safety net that travels with you instead. The endgame is to launch the first country on the internet, through Plumia, the nonprofit think tank spun out of SafetyWing and run by Lauren Razavi. They have mapped the vision to 2050, passport included.

Around the edges, the conversation ranges widely: why you cannot simply build a new Silicon Valley wherever you fancy, an unusually honest insider's view of what digital nomads are doing to cities like Oaxaca, a company culture involving rented hotels in Patagonia and a houseplant stipend, a friend allegedly building a Mach 10 passenger plane, and what AI is doing to hiring, including Joey's own story of how resume-screening software made a company founder without a degree invisible to employers.

In this conversation:

A social safety net that travels with you
The plan to launch the first country on the internet
Plumia, network states and Edge City
What would make an internet country a real country
Nomad Citizen: income protection, healthcare and one-click visas
A passport that brings its own safety net
The 2050 timeline and a flag in the ground
The future of remote work
A Mach 10 passenger plane, allegedly six years away
What Y Combinator is and why it matters
Why Joey lives in Oaxaca on an American salary
Talent, funding and why Silicon Valley is hard to copy
How exits create angel investors and startup cities
Nomad gentrification: tipping, housing and behaving well abroad
Why long-term expats reject the nomad label
Is there such a thing as nomad culture?
Hunting the next great nomad hub, and why Florianópolis keeps coming up
Patagonia retreats, Build Week in Norway and houseplant stipends
What AI is doing inside SafetyWing
Solopreneurs and who loses their job first
Dropping out at sixteen and being filtered out by hiring software
Should your kids skip university?
How to actually stand out and get hired

Timestamps (audio version, includes Timothy's episode introduction):

0:00:00 - Welcome
0:00:30 - Introduction to episode
0:06:04 - Veritas Villages
0:11:43 - Start of conversation: a safety net that travels with you
0:12:40 - The first country on the internet
0:14:07 - What makes a country a country?
0:14:28 - Nomad Citizen and one-click visas
0:15:19 - A passport that brings its own safety net
0:16:31 - Plumia, Edge City and the nonprofit arm
0:17:28 - Income protection and what is actually in the products
0:19:15 - Travel cover without the endless add-ons
0:21:42 - The 2050 timeline
0:22:44 - The future of remote work
0:23:53 - A Mach 10 passenger plane?
0:24:58 - What is Y Combinator?
0:26:03 - Why Joey lives in Oaxaca
0:27:11 - Can you build Silicon Valley anywhere else?
0:30:00 - Exits, millionaires and angel investors
0:32:39 - Nomad gentrification: an insider's warning
0:36:35 - Why long-term expats reject the nomad label
0:37:59 - Is there such a thing as nomad culture?
0:40:10 - Hunting the next nomad hub
0:40:48 - Florianópolis and Ipê City
0:42:05 - The future of work is global
0:43:12 - Patagonia retreats and Build Week in Norway
0:46:33 - Houseplant stipends and remote-first perks
0:47:50 - What AI is doing inside SafetyWing
0:49:13 - Solopreneurs and the jobs question
0:51:40 - Breaking in when AI already does the job
0:53:45 - Should your kids skip university?
0:54:24 - Dropping out at sixteen and beating the CV filters
0:56:16 - How to actually stand out and get hired
0:58:49 - Founders who cannot work for anyone else
1:00:40 - Where independent, self-driven people thrive
1:02:45 - Wrap-up and how to support the show

Guest: Joey Flores - LinkedIn | SafetyWing | Plumia

The Free Cities Podcast is the official podcast of the Free Cities Foundation hosted by Timothy Allen. New episodes every Friday. Long-form, in-person conversations with the builders, investors, residents, and thinkers shaping the future of Free Cities, charter cities, special economic zones, network states, private cities, and governance innovation worldwide.

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