re: "The next big question is: Can you scale it ?"
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.
I may have accidentally implied the semi-retirement angle more strongly than my point regarding tending to the first business as if a garden instead of trying to scale it, which was more what I wanted to focus on. Apologies if that wasn't as clear as it could be.
Perhaps I should also have mentioned that he is diversifying, where diversifying is certainly distinct from scaling the first business up.
As far as his first business goes, I still think it is worthwhile questioning the common automatic assumption that the next goal should be to scale it.
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.