I know this is from a while ago, but I re-read our discussion and would like to offer the following comments.
Looking at Bob and John, this is what I believe your misunderstanding is...
You feel that any new robots that automate their (or just John's) labor will be owned solely by Bob and that John will never be able to see any benefit from them.
I don't think that holds water, though, when you look at actual results of actual history.
Every major automation and technology eventually (usually pretty quickly) became available to the masses.
From the wheel and fishing nets, to the automobile, airplane, computers, internet, telephones, smartphones, air conditioning, medicine, etc., etc., etc...
Not ONCE was the rich able to solely reap the benefits of those advancements in technology.
Even an average (or even poor) person today can at any time jump in their car, drive to the grocery store (with the AC on and while talking to their friend on their smartphone), and buy some mangoes.
Rockefeller couldn't have done any of that at any time in his life.
Automation made that possible, and the benefits are reaped by everyone, not horded by the rich. They might have liked to horde the benefits, but they couldn't.
In other words, Bob has never in history been able to use the fish catching machine only for himself.
Once you understand that all these super amazing future technologies that replace human labor will become available to everyone (in the same way that the telephone is now available to everyone), you'll understand why people will no longer need to derive their "making a living" from providing labor for others.
This is a world of complete abundance for everyone. In a world of complete abundance, you don't need to exchange your work to make a living...
In the same way that you NOW don't need to exchange your work for gravity, sunlight, or air.
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