Not sure about cost of living in Boulder (though I suspect it is high-ish), but in the summer, my gosh is that part of the world wonderful. Very, very beautiful, and if you like outdoor activities, it’s hard to beat. I’ve not spent time in Fort Collins, but I’m pretty sure the vibe there would be very different from Boulder (not nearly as hippie/stoner/liberal as Boulder is).
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[New here, so I’m just catching up on the discussion]
Let me put in my two cents for Chicago. It’s the sweet spot of culture + affordability + great people.
In this lovely Midwestern town, you can eat any type of food, hear any type of music, see fantastic theater/improv any night of the week, attend any type of professional sporting event, visit world-class museums, hang out at the Lake Michigan beaches (in the summer!) and live in/amongst beautiful 1920s architecture on tree-lined streets in walkable neighborhoods.
You can do all this without needing a car (we’re one of a small handful of U.S. cities with serious public transit) or breaking the bank (a one-bedroom apartment in a nice neighborhood will cost you around $1000/month, a half-to-a-third of what it would cost in NYC or SF).
People here strike the right balance between “nice” and “get stuff done.” They say Americans are most uptight on the east coast, and loosest on the west coast; Chicago is the perfect middle ground, both in terms of geography and temperament. We work hard, we don’t take B.S., we’re friendly but not cloyingly so. There’s a hospitality here that’s simple, direct and honest – not unsophisticated, mind you, just honest. It’s the perfect bootstrapper’s town.
I’ve gone on long enough. I didn’t mean for this to be a sales pitch – I get excited when talking about this place. Let me know if any of you come visit – it’d be fun to connect in real life.
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I’m brand new to this group, but have to warn you NOT to move to San Francisco (at least for the first few months of your startup). My rent is $2,500 per month for a one bedroom apartment. Commercial rent is exorbitant as well, most co-working space hot desks starting from $300 per month.
A close second would be Sydney, Australia… which is where I lived before SF.
Interesting. I have to say I never really considered Chicago 
Might have to take a look.
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Surprised nobody has mentioned South East Asia yet. I’ve spent a few months in Kuala Lumpur, Malaysia, and love it. I wrote about why Malaysia is a good place to move to here: http://www.manuelflara.com/why-move-to-malaysia/
Then there’s Thailand, very famous for expats as well.
I’m currently in Bali and it’s pretty good as well. Just as cheap as KL ($1-$2 for a local meal, $4 delivered pizzas, $500 monthly rent at a nice villa with pool (not all for ourselves, though) in Canggu, next to Seminyak and Kuta (the most popular areas), $50 monthly rent for a scooter, amazing surfing and diving spots, etc. And monkeys! I think I’d like it here very much for a few months, but not longer. It’s an island in a developed country, don’t expect many of the luxuries of back home. But Kuala Lumpur does have pretty much everything you’d want for a fraction of the price, and they speak English almost everywhere.
Feel free to ask me anything about Kuala Lumpur (my wife is from there), Bali (although not an expert here) or Barcelona (where I’m from).
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I’m bootstrapping out of Bangkok, Thailand (I’m Swiss). Not really a digital nomad anymore, as I’m kinda settled at the moment. It’s got it’s fair share of advantages and disadvantages.
Disadvantage: Timezone difference to US is huge +/- 12h (to Europe however it’s very convenient especially if you hate getting up early), internet is fast enough but there is a noticeably lag, Visa situation requires you to travel out every once in a while, but i quite like these enforced holidays.
Bangkok is quite a modern city, so you can find anything you want, food, crossfit gyms, great coffee, beers, international food. Transportation is ok if you can manage when and where to travel (unlike normal office-worker expats here).
Advantages are that it’s quick to get setup, arrive here and within 1-2 days get a nice fully-furnished appartment on short term rental lease, co-working places, 3g, internet and everything else you need. You can outsource every mundane task for little money, cleaning, laundry service, cooking (eating out is cheap). Budgets: Below 1000$ it’s doable but hard (IMO also for middle-class thais). Realistically 1K$ for bootstrapping/ramen-profitable, 2000-3000$ for a good lifestyle, and for 4000-5000$ you live like a king. Other niceties of living in Bangkok is close proximity to the whole area, especially singapore and its many tech and startup events.
Interesting observation is that living in a place where things do break down gets you into a mindset of planning well ahead and setting up your systems to be more fault-tolerant. So setting up servers and human processes in a way that they can function without me become a priority.
To sum up, you can live a very nice lifestyle here for a lot less, vastly superior to the west in my opinion. I see it like with uptime SLAs, Europe/US gives you a 99.9% reliability of infrastructure and bangkok 99% which makes everything cheaper (and more exciting) but you need to adapt.
If you have any questions, feel free to ask or send PM.
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I love Pittsburgh and partly moved here because it’s a great place for a bootstrapper (came from DC where it’s very hard).
You can rent an apartment in a hip area for <$500 per month, or own a mansion in the nicest part of town for $250k (regular house in still decent part of town is easily done for $100k). Throw out your images of steel and smoke, it’s very high tech these days and has a supportive tech scene, with lots of smart people to hire out of Carnegie Mellon and U of Pitt.
Taxes are not great, but there are lots of incentives if you decide to get an office, such that it basically is free (by selling tax credits).
The weather sucks, but how many of you actually leave the house? 
Downtown Boise, ID
Pros:
- Cheap living compared to other cities in USA
- If you live close or in downtown, you won’t need a car
- Four distinct seasons (mild winters)
- Good size tech community
- If you drive more than 10 minutes, it’s a “long” drive
- Safe
- Friendly people
- Low taxes
- Boise State Football
- Appears in many “Top 10” lists such as:
No. 1 Best Cities for Men
No. 7 Best Places for Women
No. 4 of Top 10 Downtowns in America
No. 6 Most Inventive State
No. 3 Best River Town in America
No. 2 Best City for Raising a Family
No. 6 America's Hottest Music City
No. 3 Lowest Cost of Business in Pacific Northwest
Top 20 Fastest Recovering Cities
Fittest Towns of the West
No. 5 Healthiest City
Source me for 1-9, 10 from here: http://www.boiseidaho.gov/notes-info/boise-list-of-lists/
Cons:
- To get to another state or big city fast, you have to fly (and usually at least one stop-over)
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Los Angeles, CA.
Pros:
- no polar vortex.
- great outdoor activities to unwind
- good startup community
- did I mention the weather? the beach? the surfing?
- excellent food
Cons:
- pretty expensive
- traffic is very bad, but I would think most bootstrappers wouldn’t affected daily.
- home of the vain, land of the selfie.
Overall I like LA. Does it make the most sense financially? Surely not. But to me it’s not all about the finances. I already sacrificed a lot of quality of life in a previous career so I can justify this choice.
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Bucharest, Romania
I’m a local, maybe biased or missing things, but here goes;
Pros:
- cheap living, compared to Western Europe or US (rent 2-400 euros, with 2000 euros/month you can live pretty well)
- growing startup ecosystem
- big talent pool(devs/designers/sys admins/dbas)
- lots of english-speaking folks
- cheap beer & tigarettes
- good restaurants with reasonable prices (2 person meal, for an average restaurant, will set you back around 15 euros)
- beautiful and plenty of single women (can’t say about men)
Cons:
- bureaucracy and some corruption.
I work and live just outside of Toronto, Ontario Canada. Having read through a lot of these posts and talked extensively with many people across North America who run freelance/bootstrapped business I think operating from Canada offers a few unique advantages over that large capitalist country to my south.
-
Healthcare - this is a huge deal for anyone, especially if you have a family. In Canada we have universal health care covered by our taxes. The system isn’t perfect but it does prevent people from falling through the cracks, if you have a medical emergency you get care and coverage without worrying about having to mortgage your home
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Education - if you have children the public education system is here ranks very well globally. You don’t need to spend a crazy amount of money on private education.
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Exchange rates - this is potentially a win for most countries outside of the US. Over 90% of my revenue comes from the US. Until the last few years the exchange rate between Canada and US meant I could charge $1 US and make between $1.20 - $1.35 Canadian. That offers a huge advantage. I can charge the same price as US based counterparts and automatically gain an extra 20 - 35% just by exchanging the money when it hits the bank, or if needed I can lower my rate slightly but still come out ahead. In the last few years the exchange rate hasn’t been as great but I still make a few extra points on every invoice
Overall the cost of living is slightly higher than the US however one could argue the additional cost is worth points 1 and 2 above.
Derrick
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FWIW, a list of most to least economically free countries: 2014 Index of Economic Freedom
Hong Kong, Singapore, Australia, Switzerland, New Zealand and Canada top the list.
Interesting post. I’m looking to move to Spain, it seems a relatively cheap place to live with great culture and vibe.
However, this might help you out: http://www.expatistan.com/cost-of-living
I’m based just outside Bristol, UK. Rents in the city are high compared to some places listed here (2 bed flat - £600/£900 ((half the cost of London)) and cost of living standard for the UK
It does have a very vibrant startup scene (SecondSync just sold to Twitter), close ties to London and some incredible countryside on your doorstep.
I’ve just moved out to the countryside and have an hours cycle into shared office (I love both the ride and the office) and £600 rents a beautiful cottage
Cost of living with wife and no kids £1500 p/m
If you’re connected to New York as we are (my family is here, my wife’s job too), then I highly recommend Fairfield County, Connecticut.
For the NYC / tri-state area, it’s surprisingly affordable (and nice) here. Taxes are a way lower (like less than half) of what they are in New York. Awesome area to raise a family. And we’re a 45 minute express train ride to midtown Manhattan.
I recently started renting an office space 5 minutes from home, here in Norwalk, CT. I pay $500/month for it, and it’s probably 3x larger than most apartments in NYC.
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The best place for bootstrappers to live is…wait for it…
Close to their supportive friends and family. This talk of relative costs, weather, nature, infrastructure is good for daydreaming, but as someone who has tried working in various countries and on the road, you can’t beat having good social and professional networks nearby.
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Hi
I have to little boys as well. How do they cope with living there? Did they find friends? Would love to know more about your lifestyle. Thanks!
Bettina
+1 to what @SteveMcLeod said. Losing my friends/network would be a big deal for me.
I’ll share my limited experience here as well.
I grew up in New Delhi, India and moved to USA (Denver, Colorado) in 2006 for better opportunities. Since 2008, I have lived in Dallas, TX and really like it here. Compared to the rest of USA, the housing is much more affordable in TX in my experience.
I am still working on getting my Green Card (long and painful process). My wife and I had the option to move to Australia last year. We visited Sydney for a vacation, and while it’s a beautiful place, it’s really expensive. So,we decided to stay in Dallas.
I’m currently based in Holland, Michigan.
It’s the perfect small (but not too small) town. I live roughly a mile away from Lake Michigan and there is a growing entrepreneurial / art culture in west Michigan (see http://startgarden.com and http://www.artprize.org).
The cost of living is ridiculously cheap compared to SF (I’ve lived here before too and loved it) and other large cities. My 3 story, 4 bedroom house payment is cheaper than what you’ll pay monthly for a tiny apartment in SF.
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I moved from northern California (Roseville area) to Indiana, primarily due to cost of living, but also weather. I have 4 kids and my wife loves the snow. I’ve been here for a year and a half and have absolutely no regrets. I’ve never lived in the midwest before (grew up in New Hampshire, then moved west) and I love the friendly folks and family-friendly activities.
As far as tech, it’s on the weak side. There are a few tech companies, but not many. And while there are a good number of tech meetups, they tend to be in northern Indianapolis. I live on the west side, so it’s a 45 minute drive.