I would like to suggest a potentially more interesting question (or set of questions) :
_Should_ he scale it? If so, why? Why would so many HNers assume the next step to be scaling it? Might he not instead tend to his business like a garden, to ensure that it continues to be healthy, and use his remaining time to enjoy semi-retirement?
I think a lot of HNers could do with considering the above kinds of questions a bit more often. Why are you _really_ doing your start-ups? What are you _really_ looking to get out of them? Is it just to hear the 'ding!' of the cash register more frequently? I hope you're looking for more/different than that.