Good advice, check out joining IT organizations that keeps up on the latest IT, also. Apply at CSC they always have open jobs for all range.
I totally agree with this advice but would add one thing.
Tell him to make the moves and find the energy and drive to start his own business.
The time to think and act is NOW.
Don't let him set himself up to fail again by being at the whim of an employer.
Tell him to find a product or service he believes in and build a customer base of his own.
It won't be easy, but the rewards can be phenomenal.
I've been through it. Using up the retirement account just to scrape by until someone tosses a few scraps at you. It stinks!
With a lot of work and God's help, my family made it. Your friend can too!
Good luck and God bless.