And if they expand their business and go into more markets and become a technology company like Amazon (which started by only selling physical books online) or Google (who started with just a search engine), then how would the decision to not sell be viewed?

Or if he did sell and used the money to go on a cocaine bender and died in a hotel pool from an overdose - would selling have been the best thing for him?

Do you see how pointless "what if" scenarios actually are? There are too many variables to properly account for - you can't just change one variable (like a decision) and assume everything else turns out exactly as you would like.