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To understand the word yuppie, I believe a mini-geneaology is helpful. Many yuppies, during the 60s were hippies who opposed the Vietnam War with their slogan of peace and love. At the beginning of the 70s, this movement died and most of the hippies sold out. The energy and momentum they had created, they poured into the capitalist market, and rather than make love they started to make money. That´s why I believe the term yuppie has connotations of inauthenticity because many yuppies once had a higher ideal; they were playing a bigger game and they traded it in for consumerism.
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