You know how it is. If you habitually wear rags, the reactions depend on who you are. If you ARE poor, it is the poor-fellow-he-cannot-afford-anything-better reaction you get. If you are in the middle class, the reactions range from 'miser' to 'uncouth', taking in 'tasteless' on the way. If, however, you are uber-rich, it will be 'how simple and unassuming the man is'. (If you also have charm and presence, who knows rags may become haute couture, and become totally unaffordable for the poor!). Unless, of course, the other guy is also uber-rich!
If you did not know this basic truth, you would consider it ironical that a guru, who is supposed to be spiritually enlightened and above all this social climbing, is respected ONLY if he is a success by the mundane standards of society. Enlightenment is validated only if the said guru runs a successful charitable or religious organization or rubs shoulders with the high and mighty or both, failing which he is considered only a loser masquerading as a guru. In other words, you would prefer to learn about the futility of chasing material success only from someone who has achieved material success!
Needless to say, it is also mandatory that he be perfectly coiffed (NOT Mohawks and all, thank you. Yet! Flowing hair and flowing beard, but not unkempt, oh no! How can one take someone to be one's guru if one is ashamed of his haircut?), impressively dressed and articulate. If a spirit that is free of all these material considerations of life fails to even notice how it is clad, let it roam the Heavens in bliss, no quarrel with that. But we shall not respect it for its enlightenment or seek to learn from it. (Yeah! Such a spirit will probably not even notice the disrespect, maybe, but what do we care about what it notices or does not?)
That, though, applies only to gurus who started out that way. The other lot who get respect are the ones who abandoned their careers and became spiritual. In which case, it is probably not necessary to be running a famous organization and all that. Note, though, that they have to abandon SUCCESSFUL careers if they are to be respected and not middling ones. (Unless, of course, they make a success of being gurus - the successful charitable/religious organization, coiffure and all that jazz.) In other words, you need to have BOUGHT that Ferrari first and THEN sold it, if you are to gain respect. Of course, you can be enlightened even otherwise and be a blissful spirit, but a guru of many you certainly shall not be.
It does not do, of course, to reverse the order. I mean, if you start off being a guru, THEN start a successful business and all, you probably may be respected as a businessman but you probably blotted out all your chances of becoming a successful guru. It is no help to be the monk who BOUGHT the Ferrari in becoming accepted as a guru. You could try to later sell it off and re-establish yourself as a guru but I rather doubt that it will work as well.
Ergo, to be successful at teaching people to abandon the stress of striving for material success, you first need to be successful at achieving the same sort of success. Talk about the irrationality of the human species!