I'd highly recommend starting your own software company. And I'd highly recommend traveling around the world. I've been doing both for the better part of 10 years. At the same time.
So my advice is to do a quick search & replace on your question. Switch "or" for "and", turn it into a statement, then go do it.
Also, do you think having such a lifestyle can have be called as truly financially independent?
In the meantime, here's a quick overview of what I've been up to since I started working from the road:
From a financial perspective, it's completely counterintuitive that traveling is actually a lot cheaper than staying at home. But if you think about it a minute, it starts to make sense. Imagine you cut your rent and car payment down to zero (by ditching both car and apartment), as well as all the little bills that went along with them. Now replace that with the comparatively small expense of staying in $5/night accommodation, and otherwise living on about $20/day.
When I was planning my first long trip, taking the $2,000/month "keep life in the US alive" line-item out of the spreadsheet extended my $10k budget from 2 months to 10 months. Bill a day per month, and yes, you're pretty much set for life. Of course, you're only set for life if you don't plan on coming home, so it's probably best to leave a bit in reserve for when you do.
Out of curiosity, are you writing software or managing programmers remotely?
I tried traveling and working as a consultant but dual screens and comfy chairs don't do well in a suitcase.
South America is more realistically $25/day all in. SE Asia, as mentioned is about $20. Indonesia is more like $10. Africa is free.
For western european hostels budget about 16 euros per day. It used to be closer to 8 but the supply of budget travelers has increased sharply in the last decade.
I always feel like the lack of a universal healthcare system in the US discourages lots of people from pursuing a startup full-time.
If by startup, you mean a one man website that is some kind of low-maintenance subscription service, then yeah sure, go travel the world.
But if you define startup as I do, as a venture-backed, aggressively growing company employing people, then how the hell are you going to travel the world while managing that? Please tell me if you have a way, because I would be genuinely interested :)
I put my thoughts together here too: http://swombat.com/2010/12/27/startup-vs-travelling-lifestyl...
With a small, niche, business; I can see it happening no doubt. Like running a small remote consultancy or e-commerce site selling drop shipped products. But a startup needs its founders present, communication face to face is unbeatable and often times your cofounders aren't set to travel the world with you.
So, what's my advice? Live some life while you're building your startup, man; go on short trips, go to Burning Man, visit Prague or fly to the B.V.I for four days. Be sure you have some fun. Once you've either succeeded in making FU money from your startup, or your startup has failed, then go experience the world (you don't need FU money to see the world, hence why you do it even if your startup fails).
My plan? Either FU money, passive income, or a failed startup. Once one of those things happen I'm planning on crewing on a sailboat to get to Europe (or SA, or Aus) and living life for a while outside of the USA (think...years).
I've done my share of remote consulting for venture-backed, aggressively growing startups. For the last 6 years, at least, I haven't physically set foot in any of their offices.
If you want to do it with a whole team, here's how I've done it in the past:
Now that the site's starting to take off we're planning on staying in the same place for a few months (still outside of our home country), but so far we've found balancing the two less difficult than we had expected.
Now paraschopra's definition of a startup is closer to the traditional VC backed, big payoff definition. He hopes to make it big, become a leader in the field of A/B testing and get FU money...
None of those two ways of thinking are bad. It's essentially a question of risk and reward... The first can lead to financial independence with a nice recurring revenue (for example letsfreckle.com or one of my customer who earns 20 000$/month profit with his website while delegating all the work) and is usually less riskier and less stressful.
The second type of company is more of a high risk high reward scenario where if you get bought or IPO, you get enough FU money to truly have financial independence...
So, it depends on where you stand on the risk/work reward scale... I don't want to look back in a few years and feel that I've wasted my life trying to earn it. So, while I do work long hours, I take breaks, I go on holidays and I travel and use Wifi connections to do any urgent work that comes up. I don't expect my business to be the next google, facebook or flickr but if it's profitable and allow me to support a comfortable lifetime while eventually not taking too much of my time I'll be happy..
I think that if I can sum it up in a thought it's this: there is a remarkable difference between reading and thinking and reasoning about a subject, and actually experiencing it. Even if I don't use many of the facts I learned while traveling (i.e. the odds and ends of the Knights of St. John's defense of Rhodes against the Turks and their subsequent move to Malta), I learned that it's one thing to read about the layered defense of Rhodes, and another to actually walk among it.
In other words, I can read and reason all I want about the situation of my customers, and their problems and solutions to those problems, but until I actually get about working with them, in their space, on their problem set, with their data, and within their constraints, I'll never really get their issues and thus never really provide a 1-1 solution for those issues.
It might seem like a simple concept, one I thought I understood before I set about traveling far and wide, but I really grokked it much better after seeing the world and trying to understand.
(oh, and the never ending different national interpretations of historic world events I find endlessly fascinating and very perspective setting -- very helpful when understanding how to think like your customers)
But I still don't agree with that premise..
100 + hours of work per week?!
What kind of startup is this? That's 14 hours / day!
My rule of thumb is I need to stay about a month at each location, so that I don't feel rushed and it's worth the time to setup a temporary base.
A week-long vacation, trying to cram everything in the shortest amount of time, is not real "traveling" for me.
In fact, it can be quite refreshing to meet different kinds of people (not just more startup people). I did this for three months this year (lived in Saigon) and I look forward to doing more of this in the coming years
That's probably true in the US, and to a lesser extent Europe, but in places like Southeast Asia, Central & South America, etc., the internet is everywhere. As in, pick the most remote beach you can find, and so long as there is a little grass hut to sell you beer, there will also be an internet cafe.
The cool part is that the more off the beaten track you go, the cheaper things get. Look in the jungle behind that beer-selling, wifi-having, hammock-laden beach bar and you'l find rows of little bungalows that you can rent for $200 per month.
Bootstrap your startup on a beach like that and suddenly "ramen profitable" becomes "paradise profitable", and you'll discover that you can live there indefinitely on just a few dozen new paid accounts per month. Or, if you prefer, do one day's worth of billable work per month to keep you living like a king.
Don't forget to send us a postcard.
Wifi might be prevalent in most places but quality and reliability will always be am issue. I've found it to be ubiquitous is SE Asia, however I've had days where slowness could cause even SSH to bog down to a few characters a minute.
Bigger issue, do you mean travel or live in a foreign country? Because yes, you can very easily find a cheap country with good internet, but traveling itself can be a full time job when you're only spending a week at a time in one place.
If it were me, I'd just travel, and do the startup later.
- Do you create a company before leaving, or after coming back home? (That would allow you to charge for early versions of your product, thus verifying people are interested to buy)
- How do you tap in the local developer/designer community to outsource part of your project?
- How do you decide whether to rent an apartment/stay in hotels? I would prefer to stay in an apartment, however I imagine you stay first in a hotel in a couple of days before deciding to rent an apartment.
- What kind of place did you find more energizing to work at? A busy metropolis, or a remote village with fantastic views but no like-minded people?
2. Be on a lookout for local barcamps/tech events. I attended Barcamp Saigon last month and it was big - http://twitpic.com/3f8gn0
3. Start off by staying in a hotel and then move into an apartment if you want to.
4. I think this depends mostly on where you come from. Since I come from India, I like the hustle bustle of a place like Saigon. Also there are a lot of clubs there and I like that. The best part is that you can easily move to another city if you want to. You just have your backpack to carry around :)
a) telecommuting employees
b) visiting customers
c) potential recruiting
d) valuable conferences
Startups are a crazy crazy adventure.
This of course has disadvantages, I cannot speak to local customers in person, but on the other hand living is much cheaper and more interesting than at the current place I call home.
I wouldn't want to manage a startup while traveling from place to place, but I think it should be no problem to just work from somewhere else and do weekend trips. This is exciting enough for me and I think I can get to know the world better with a couple of short term stays than traveling non-stop.
If I feel I need to go home to make progress, I go home, otherwise I will continue to live in different places all around the world.
While it's possible to travel and do certain kinds of "lifestyle" startup, I think traveling around the world, or even extensive personal trips, are incompatible with a high-intensity venture funded startup. It's just not fair to the other team members who depend on you, your investors, etc. I can see taking 4 weeks a year off (spread out a bit) as long as you stay reachable, but that's about the limit.