I would recommend he take operations roles at a tech startup.

Growing companies really need people who can keep things running as they grow. Experienced people want more senior and sexy roles, and inexperienced people can make fatal mistakes.

It's a nice combination of getting the logistics and relationships right, and the latter can be very rewarding.

He should shop himself to VC's as team filler. They'll relate to him, and can plug him in to gaps as needed.