However, I don't agree with your second part. 4 years in prison isn't just 4 years in prison. It is 4 years in a situation that is widely out of your control, and opens you up to a host of threats that you didn't consider during your 'outside' life. Sure, you can be hit by a car and killed during normal pedestrian action, but it's quite hard to be the victim of prison violence when you're a normal citizen.
Imprisonment is terrible, don't sell it short. It is a completely different world than every day life, including that of an expat, and it very well may stay with him for the rest of life in the form of a crippling physical or mental injury or even death.
He runs a SaaS, not a hot-dog stand. The power of the internet is internationalism and non-locale.