The 5 Best Cities to Live in as a Bootstrapping Entrepreneur

Written by Andrew Henderson

If you’re a young entrepreneur starting a business, you need all the advantages you can get. That means keeping costs low and building advantages over your competition. If your business isn’t rooted in one place, you can use geoarbitrage to take advantage of cost differences between countries. Why start your online business in California where rents are thousands of dollars a month and the cost of living is through the roof?

There are places all over the world where you can live relatively well for as little as $500-1,000 a month. Even better, you can tap into the local talent pool for pennies on the dollar of what you’d pay in the western world, if you need employees to come into the office. This cheaper cost of living will allow you to pump more money back into growing your business, all while enjoying a new culture and networking with like-minded expat entrepreneurs overseas.

But what are the best cities to live in to cut costs, enjoy a better lifestyle, and find a network of talented employees and business contacts? Here are our picks for digital nomads…

Top 5 Best cities to live as a bootstrapping young entrepreneur

The best cities to live for an entrepreneur include Montevideo

Montevideo, Uruguay: while it is more expensive for digital nomads than other cities on the list, it offers some of the best living in South America

5. Montevideo, Uruguay

A lot of bootstrapping young entrepreneurs love the Latin lifestyle, and while South America doesn’t offer the extremely cheap prices, cheap labor, or go-go-go attitude parts of Asia do, it can still be a great place to get your business of the ground. While Uruguay may not be tops on your travel list, it’s one of the best cities to live. Prices are not as cheap as in Southeast Asia, but manageable if you live more like a local. If you have a location independent business, Uruguay has some of the world’s cheapest internet, with the fastest speeds in South America. Uruguay has one of South America’s freest economies and is an emerging offshore banking country. Beaches in Uruguay are great, healthy food is widely available, and things move at a little slower pace (worth considering if you’re hiring locally). However, like many countries in South America, it really helps to learn some Spanish. Uruguay has an educated middle class labor force and is regarded as one of the safest countries in South America. While Chile is another great choice for expats – and arguably cheaper than Uruguay – the tax consequences for those who become tax resident there are more troubling.

Best cities to live include Ho Chi Minh City, Vietnam

Ho Chi Minh City, Vietnam: whether you’re a bootstrapping young entrepreneur or have a family, “the Hoch” is one of the best cities to live in Southeast Asia

4. Ho Chi Minh City, Vietnam

In addition to being one of Southeast Asia’s most livable cities, Ho Chi Minh City is a great place for a bootstrapping young entrepreneur. In fact, the city is filled with expat entrepreneurs, including thought leaders like Tropical MBA’s Dan Andrews (hear my interview with him here). You can easily rent a serviced apartment near the city center for $500 a month, and there are plenty of expats looking for roommates, as well. English is improving in Ho Chi Minh City, which is Vietnam’s most livable city and the most friendly to business and foreigners. With its huge population, there’s plenty to do and endless international food options abound at cheap prices. Plus, wifi speeds have improved dramatically.

Best cities to live for entrepreneurs include Chiang Mai

Chiang Mai, Thailand: a favorite city of digital nomads, it’s also third on our list of best cities to live if you’re a new entrepreneur

3. Chiang Mai, Thailand

Long a favorite of digital nomads and the young entrepreneur, Chiang Mai is one of the best cities to live when starting a business for one simple reason: it’s cheap. While Thailand has long been a top destination for Asia expats, Bangkok has become rather expensive and doesn’t even top the list of best large cities in Asia. However, Chiang Mai is the dirt cheap, highly livable alternative in Thailand. Situated in the north of the country, Chiang Mai is a much smaller town – and much quieter – with world-class services like really fast wifi. Relatively nice apartments here run $500-600 a month, often with utilities included, but smaller apartments can be had for as little as $200 a month. And because Thailand is a strong area for expat entrepreneurs, you should have no problem networking here, or after a short flight to Bangkok for the weekend. On top of that, medical care in Thailand is excellent and extremely affordable.

Best cities to live for entrepreneur include Bucharest, Romania

Bucharest, Romania: the best city to live for entrepreneurs who want a European base

2. Bucharest, Romania

Love Europe, but thought it was out of your budget’s reach? Romania is making a name for itself as a great yet affordable place for a young entrepreneur as well as a budget traveler. In addition to having some of the fastest internet speeds in the world, Romania is one of the most emerging countries in Europe. That means costs are cheap (one study suggests a backpacker can make it on $23 a day), as is labor you may need. Romania is one of the top countries in Europe to find outsourced labor on sites like Odesk, and you should be able to easily find relatively qualified technical gurus for as little as several hundred dollars a month. On top of the cheap cost of living, Romania’s position in Europe gives you great access to tons of other affordable travel destinations by train or cheap flight, from the castles of the rural areas, to Hungary to the beaches of Montenegro.

Davao, Philippines is a great city for location independent entrepreneurs and digital nomads

Davao, Philippines: the best city to live if you’re an entrepreneur… Davao City offers a slower pace, while the surrounding areas offer idyllic beauty

1. Davao, Philippines

While many expats scoff at the idea of living in Manila (an opinion I don’t share), plenty of digital nomads are happily residing in Davao. The entrepreneur community there is substantial, thanks to its substantially cheaper cost of living over the “big city”. Located in the south of the Philippines, Davao is one of the safer parts of Mindinao. Davao’s low cost of living and laid-back atmosphere has attracted its share of online business gurus. Expats claim Davao’s weather is better because the city is outside the typhoon belt, and it mostly rains at night. And you can live like a king for little cash; a small apartment outside of the city center can go for as little as $150-200 a month. That should leave a lot of extra money to build your business while networking with others in Davao.

You can see that living overseas not only helps you save money – money that can be plowed back into your ventures – but offers great networking opportunities with forward-thinking global entrepreneurs.

If you want to create a business empire but aren’t sure how to start, I recommend Chris Guillebeau’s Empire Building Kit. It’s a 365-day battle plan for creating a lifestyle business so you can enjoy your time overseas. The kit includes real case studies from entrepreneurs who launched businesses that now pull in six figures. And it’s easy to absorb the information because it’s available in a series of articles and videos. Check out the Empire Building Kit here.

Andrew Henderson
Last updated: Jan 13, 2020 at 2:54PM

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  1. Pete Sisco

    Great list. Hard to restrict it to five, I’m sure. There are so many great places to live and work, especially when you do it online. Honorable mention to Kuala Lumpur and Penang in Malaysia. It’s also pretty easy to stay in that country a long time because they offer a lot of visa options.

    • Nomad Capitalist

      Thanks, Pete. There are a lot of great places, but these should work well for those with limited funds who need to pump money back into their business. As you know, I’m a huge fun of Kuala Lumpur.

  2. anarchobuddy

    Thanks for the list. I find it especially helpful for someone like myself who wants to bootstrap. Now it’s a matter of getting the business off the ground…

    • Nomad Capitalist

      Thanks for commenting. Now find your business and get packing!

  3. Joseph Magnotti

    Glad to see Davao maybe number one! Thanks for the mention and see you soon.

  4. Steven

    Very interesting post.. I’m breaking my head here on where to go and live for a while this time 🙂 I’d love to go to a place to meet up like-minded internet entrepreneurs

  5. chasingplaces

    Wow, Davao. I saw a growing number of expats here, mostly working on a variety of web-based businesses.

  6. The Allegiant

    Wish Taxes where a factor in this list

    • Global nomad

      I agree with Allegiant. The most important things in choosing a place are visa and taxes – which I don’t see mentioned. If your business is actually making money, you can’t ignore these factors.

  7. Victor Nobrega

    Excellent article!! Heading to Davao in two months to have a look!!



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