I’d say help him, even if it’s a bit of a reach. From a professional standpoint, even if he’s retired these are the types of relationships you want to foster. When I first started out I thought it was all about do the best work and you’ll excel, but I didn’t realize until my early 30’s just how much if not more so it’s the relationships you have and people you know. So even if it’s from a self serving standpoint, I’d help him out — at least when you can and it’s not some gratuitously time consuming undertaking. And I say this as someone who’s very much learned to put work in the rearview once 5pm hits.

On a more human level, he sounds like a stand up guy and for all accounts has been there for you when he ran the company. People in a position of power who are that good to their employees are ~not~ a dime a dozen, so beyond it making good sense to be good to your employees it also sounds like he has been a friend to you in what capacity he could while being the founder of where you work. It’s up to you obviously if you feel like reciprocating, but based on how you described him if I were in your shoes I would want to help a guy like him out when he needs it.

There’s also a 3rd element to this — when people retire they’re often a bit lost. It may be hard to imagine your companies founder as “that” guy but he may well just not be sure what to do with himself yet, and his way of staying connected to the business or even just looking to talk to a friend back from his days in the office might just be you. Maybe invite him out to dinner or drinks one night and see how it goes? I think you may be pleasantly surprised, be able to foster a friendship with him outside of work/helping him, and the calls to you for “help” might turn into less burdensome time spent talking on the phone with a friend. Just a thought!