Next to avoiding bad elements, employment is the biggest challenge I have seen ex-inmates face. I watched as my friend responded to over 200 jobs on Craigs List, Monster and Hot Jobs. Most of the time he never got a response back. When he did get interviews, they would practically offer him the job, remark how qualified he was, and promise to call him for a second meeting. He would then hear nothing. What happened was, after he left the interview, they would run a background check and find his arrest record and disqualify him as a felon.
After 7 months, he got a job. He had left the question about arrest and felony blank on the application. After working for two weeks, doing excellant work, he was let go. I was a month more before he finally met a business owner who would give him a chance. He is doing very well and is very appreciative of hiss new boss.
All this trouble and his crime was DUI!!! I can't imagine how hard it would have been if it was a violent crime.
My suggestion is to support him and constently encourage him as it will be a long process. Don't let him get down. He needs to apply to everything, everyday and be honest about the past.
Good luck to you