This is just specifically for your friend's situation; as it seems he has experience in running a business, dealing with customers, and doing it solo. I would

This is just specifically for your friend's situation; as it seems he has experience in running a business, dealing with customers, and doing it solo. I would point him in the direction of learning tech skills that compliment him in an entrepreneural sense, versus aiming for an outright switch in his career. Good examples would be web and frontend design, server administration, e-commerce and payments, etc. Those are the kinds of things he can use to automate his business and even make inroads within his "industry" — with the added benefit of not having an extremely steep learning curve for producing something useful at the end of the day.