I personally find the topic interesting for various reasons. For once, because i've been living a "nomadic-founder" lifestyle for the last 17months (sidenote: rather "nomadic broke" than "nomadic rich" :) and because my startup creates a platform that tries to free more people from classic employment and enables them a global "workdesk".
My whole journey was inspired by someone's travelling-story on reddit, which is why i'd like to share mine here. Maybe someone thinks about doing something similar, in which case i hope my story can give insights/inspiration as well.
I'm in my mid-20s, IT-guy for >14years, YC alumni, don't have kids, speak 2 languages (english & german) and in the process of learning spanish (thank you duolingo!). When i started, i moved out of my apartment, gave away all my belongings but a backpack of clothes, my camera and thinkpad. I had only little money on the side and apart from my role as a startup founder, not really any perspective on regular income in the near future. Never had plans for more than 1 month ahead, sometimes plans would completely change in matters of hours. I was expecting to be living very low profile and in case money runs out completely, find some simple job to get by. Money and materialistic belongings became my lowest priority pretty soon. On the upside you gain a completely new sense of freedom. (A particular quote from "Fight Club" immediately comes to mind)
So moneywise, in the first few months i was still employed and working remotely for a befriended company as a programmer. But that ended soon, because i wanted to focus more on the startup. One of my co-foundes had some funds from his former startup with which he could support the team for some time. Not overly much, but enough to get by without much luxury. Earlier that year i got the opportunity to build a funded art-installation[0] that won a price and some money. But to be honest: I'm constantly broke, but somehow there's always a way if you want to.
You'll learn to enjoy your life with the little you have. You get creative eating healthy for little money (have never eaten so much good fruit in my life) and finding places to stay. Mostly i stayed in hostels or i could live with people i met on my journey. Sometimes only due to their hospitality, sometimes in exchange for work (small IT stuff, built a hostel, crafted a "designer locker", gardening and so on). When you stay in inexpensive hostels (my only requirement was wifi), you'll also meet interesting people that are in a similar situation and learn new ways to get by.
For the last 6 months i've been in south america. Life here is comfortably cheap. Most of the time you can easily get by with 10$ a day or even less. And if you're schedule is flexible and you're not in a hurry it's easy to experience some of south-america's incredible nature for little or no money. And you will meet interesting people and life-changing moments travelling outside the usual touristic way of moving around these countries.
What i'm trying to say: If you feel your situation is similar and you maybe even have some money on the side for the beginning: do it. You will not regret it. Don't be scared and never give up. Just always remember that, even if hard times come, there's always a way and surviving those will only make you stronger. You'll find a simple way making money on the side for food & shelter (heck, here in south america you could just be making and selling bread or cake on the street for some hours a day and get by).
Needing only your laptop and wifi to work is an incredibly enabling gift. Pretty much everywhere i went i had access to wifi and could work on my startup and communicate with my co-founders. Take use of that gift and you will have a life-changing experience. Founding a startup in such a globalized way _is_ possible with some coordination skills. Our whole team is spread around the world for the whole time being and we successfully launched a couple of months ago.
Shameless plug: We[1] are building a plattform that enables many many more people to live a location-independent lifestyle like ours. Our vision is that you'll be able to work directly on our site, offer your expertise and/or being presented with jobs directly targeted at what you're good at, always knowing how much money a finished job will make you. We're still in the process of collecting feedback and iterating. Getting a two-sided marketplace off the ground is hard :)
If you have any questions about the story or feedback on our startup, i'd be happy to answer them here or contact us at hello@workio.com