Psychosmurf comments on Political ideas meant to provoke thought - Less Wrong
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Well more than zero is still more than zero, right? I think if you expect to be disappointed by the results of an endeavor, then you may as well revise your expectations downward from the start, so I don't see that as much of an obstacle. (I also don't believe in the existence of values, so no problem there either).
I actually agree with your friend that you don't need any special skills to get rich(er) (neither in capitalism nor in any other socioeconomic system), you just have to do the bare minimum required not to sink your business, (and yes you can pay other people to do the work and the thinking for you), but I would disagree with the notion that this will lead to automatic success.
Since there are many more poor people than rich people, it follows that not only is it difficult for poor people to become rich but also that it is easy for rich people to become poor. Some rich people get richer, but most get poorer. (Nonetheless, I do believe that the richer you are the harder it is to fall to a given level of wealth) Hence, it is my belief that the most successful businessmen are outliers and their success is mostly due to variables that are out of their control.
Ultimately, I think your friend's reluctance toward your plan was justified (though maybe not for the same reasons he had).