What's done is done. No matter how much thought he has or has not given to it, no matter how well or disastrously it has worked out, whatever he leaves behind is his legacy. The world he leaves -through death, disability or retirement - belongs to those who come after him, his successors. For better or worse, they have picked up the baton and are carrying on his dream.
All that has gone before, the events I discussed earlier, all good and bad decisions, come to roost on shoulders of the successors. They inherit restrictions, frustrations, and deficiencies at the same time they inherit opportunities. It's a package deal, a deal they have to live with. As much as they may want to at times, they can't bring back the departed founder and set him up in a boardroom chair and beat him up because of what he did or failed to do.