I'm all for starting pretty much anything at any age. Now that I have that out of the way, the larger issue is if he will find anyone to employ him at that age

I'm all for starting pretty much anything at any age. Now that I have that out of the way, the larger issue is if he will find anyone to employ him at that age. Ageism is a real thing! I spent the last 5 years working at an outfit that the recruiter described as "they seem to prefer seasoned employees..." take that however you will, but half of my co-workers were over 50 and I had at two people reporting to me that were older than I am. BUT, they were all experienced engineers. I think it will be hard for him to find a job as an entry-level programmer at his age. But if he's been an executive, he probably has enough of a network so he can find freelance clients. The reality of software development is that there is a huge body of work that can be done by someone who's new to the field. This is probably the most worthwhile path for him.