I'd trade places with Person A any time!
If what made him tick was a sense of purpose, of seeing the company he founded continue to grow there aren't many options apart from go back to the company, found a new one, or ??? Maybe option 2 is too much work, and without the carrot of a big payoff he'd lack the drive.
You'd happily trade places because you believe money buys happiness. This person has learnt it does not.
He touches on this in the article, he was interested in starting new projects but they went nowhere. So I am reading this as "no, he cannot just go do that", he is worried he only was able to do it the one time.
Which is not to say that the person with money can't then find additional problems, or use the money such that they reintroduce a class of problems.
I am happy. My life is amazing in terms of health, fitness, diet, family life, where I live, travel etc.
But I am also without a driving force. It gives me a new appreciation for the athletes or musician who un-retires.
I have a friend who phrased that very well: the problem is "you're waiting for death" because a life without a "driving force" is just waiting for death, as it will eventually do its part.
> I am happy. My life is amazing in terms of health, fitness, diet, family life, where I live, travel etc.
Waiting can be happy, but it's still waiting. Also, how things are during the wait will change: fitness and health aren't perfect forever, likewise family members aren't immortals
No judgement value is implied: that's what retirees do, and what most people aspire to do, so it shouldn't be so bad.
Yet I believe we as human beings need things to do.
Was a really interesting read and gave me a lot to think about as a (hopefully) future founder!
Of course, not everyone matches the writer's motivations, and he went and told the reader what those motivations are.
I love the movie birdman, on the topic.