It sounds to me like a major obstacle for him is lack of experience. I'd have a quick answer for that by offering any company I interviewed with (where I wanted

It sounds to me like a major obstacle for him is lack of experience. I'd have a quick answer for that by offering any company I interviewed with (where I wanted the job) a "free trial", and work for free for 1-2 months as a consultant/intern. The trick is just getting in the door.