You are indeed the genuine loyal friend that he needs to get re-established. Some of the comments here are good suggestions.
Assuming that you are also involved in IT (well you do read HN) are you able to help him get some consulting gigs? If he is motivated and able to get some basic support, then doing small, well priced jobs for local businesses is a great way to ramp up.
Being a consultant avoids the employer background checks and helps him avoid the low pay trap of menial jobs. You may need to monitor his manners and speech as after 18 years, he may have picked up some habits that are uncool in our current society.
Assuming that you are also involved in IT (well you do read HN) are you able to help him get some consulting gigs? If he is motivated and able to get some basic support, then doing small, well priced jobs for local businesses is a great way to ramp up.
Being a consultant avoids the employer background checks and helps him avoid the low pay trap of menial jobs. You may need to monitor his manners and speech as after 18 years, he may have picked up some habits that are uncool in our current society.
Best of luck to you both.