The hours may be long, but few professions offer as much flexibility as that of the software developer. I'm not just talking about not needing to dress or bathe properly. If you're a programmer on vacation somewhere and never want to leave, maybe you shouldn't. Many places will welcome experienced software developers with entrepreneurial spirit.
What does the welcome look like? In Thailand, the Board of Investment can help you with tax incentives, including an eight-year tax holiday that can be deferred for up to five years if you lose money during your first few (which is common with any start-up). The Board can help you with visas and all the standard legal stuff that might arise. If you become rather successful, there's a "one-stop shop" in Chiang Mai where they can connect you with various agencies for visas, taxes, and real estate.
A tale of two expats
I spoke to John Douglas, the head of Mycos Technologies in Chiang Mai, who's been in Thailand for more than 12 years.He started out in Colorado and worked in Texas for a larger company. Having no previous experience running a company, he moved to Thailand. He was originally on vacation and immediately fell in love with the culture, food, and people. Luckily, his daughters were young and his wife was agreeable.
He took advantage of Thailand's untapped talent and lower cost of labor (45,000 baht or about $1,400 per month is considered high) and developed charting components for .Net, achieving "modest" success without marketing or sales departments. From there he was able to land a few clients from Ireland, Australia, the U.S., and France, mainly doing offshore programming work. Currently, Mycos has grown to about 45 people primarily through word of mouth.
I also spoke to Steven Prussky, who started two companies: SiamMandalay and Aware Corporation. In 1993, Steven visited Thailand and witnessed the artistry and crafts in the northern area around Chiang Mai. By 1997, he'd moved and incorporated as a limited company in Chiang Mai and has since expanded. I toured his compound, and it's an impressive combination of Thai and Western architecture, which Steven understandably takes great pride in, since he designed it and focused on small details like exposed brick (which in Thailand is seen as odd).
Because Steven was an IT guy by trade, he automated and built software around his business. While doing trade shows around the world, including in the United States and his native Canada, people would see his software, which delivered the real-time inventory and supply chain management we now take for granted to the crafts industry. Other companies started to want that software, too.