Sharon Pomerantz’s debut novel, Rich Boy, features a man who spends his life trying to outrun his humble beginnings, initially to thrilling (though familiar) results. As a portrait of the 20th-century American man, Rich Boy is a competent bildungsroman right up until its protagonist stops learning from his own mistakes, and its predictable structure proves not so sturdy.

Raised in a working-class Jewish neighborhood in Philadelphia by a crossing guard and a postal worker, Robert winds up jettisoning the most embarrassing details of his upbringing and recreating himself at an early age in order to get what he wants, from the best-looking girl at the bus stop to a scholarship to Tufts University. In college, Robert runs with the idle offspring of the rich who were rejected from Harvard, and he moves in with a beautiful British political activist. Meanwhile, he picks up shifts at the college cafeteria and scrambles for overnight cab-driving shifts so he can buy food. Watching Nixon’s resignation prompts him to enter law school, where he forges a path into real estate, juggling the mandates of developers and the efforts of artists and historians whose backgrounds hew closer to his own. Aided by an impending marriage to a Manhattan socialite, Robert hopes his new pedigree and charm will forever efface the threadbare tracks of his past.

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Pomerantz’s favorite description of her protagonist is “unaware,” as he carefully navigates his social world without realizing the degree to which others will take his new persona on faith. (His friends, too, are often hiding something; certainly his closeted college roommate has more to lose if his background is revealed.) Robert constantly hears a drumbeat of “make money, make money,” but what he wants from it is the power that will smooth his way through life, just as his moneyed WASP friends unwittingly employ it to their benefit.

Yet a number of evolutions later, Robert Vishniak looks like a cipher, and Rich Boy begins to collapse in on itself. Robert can’t enjoy the fruits of his deceit, and his desire to keep reinventing himself inevitably leads to trouble. Pomerantz’s prose loses its satiric bite as it follows him, lending gloss to a world that had earlier been exposed to a younger Robert as hollow. His recognizable trajectory doesn’t work against him until Pomerantz forgets what made him so interesting in the first place. Once she stops reminding us of his aloofness and how unaware he is that he’s playing the role of “poor kid who makes good,” his background fades and he becomes just another arrogant asshole.