He seems to? How do you judge that? I feel like most people who make statements like that really mean "if I were given the choice between the two lives, I would

He seems to? How do you judge that? I feel like most people who make statements like that really mean "if I were given the choice between the two lives, I would choose Tom's over Zuckerberg's." That doesn't tell you anything at all about who's enjoying their life more, since you're neither Tom nor Zuckerberg, and their goals/priorities/values are probably very different from yours.