Ken Jennings's Five Essential Business Reads

All-time "Jeopardy!" champion Jennings Photograph by Ben Hider/Getty Images

From June to November 2004, Ken Jennings accomplished a daunting feat: He became the only Jeopardy! contestant anyone can actually name. He won 74 straight games, taking home a staggering $2.52 million. A former software engineer, he’s since become a bestselling author. In his new book Because I Said So!: The Truth Behind the Myths, Tales, and Warnings Every Generation Passes Down to Its Kids, Jennings sets out to debunk common myths. (For instance: “Your first answer is usually the right one.”) While Jennings admits that he does not read business books—his 4,575th answer, about H&R Block, ended his winning streak in 2004—he uses strong business themes to explain his favorite American novels.

Bartleby the Scrivener, by Herman Melville. “At just 18,000 words, this is a novella at best. But hey, even that puny word count probably makes it longer than half the business best-sellers I see advertised in in-flight magazines. Subtitled ‘A Story of Wall Street,’ Melville’s story introduces us to the title clerk at a financial firm, who begins replying to every single office request with the phrase, ‘I would prefer not to.’ We’ve all worked with a Bartleby or two, I assume.”

Then We Came to the End, by Joshua Ferris. “I worked for a little Internet startup around the time of the dot-com bubble, and Ferris’s remarkably assured and darkly funny debut novel absolutely nails the reality-challenged corporate culture of the era. It also has what I consider to be as perfect a final sentence as any novel ever written. Ferris’s 2010 follow-up, The Unnamed, about a Manhattan litigator who develops a most unusual psychiatric disorder, is just as good.”

The Bonfire of the Vanities, by Tom Wolfe. “Speaking of books that sum up their business eras, let me re-introduce you to Wolfe’s nominal protagonist, Sherman McCoy, a self-described Wall Street ‘Master of the Universe’ with a Park Avenue penthouse and seven-figure income to match. But is he untouchable?  SPOILERS: No. Wolfe’s real protagonist, of course, is New York City itself. And the junk bond-trading, power tie-wearing, coke-vacuuming 1980s. Good times!”

The Last Tycoon, by F. Scott Fitzgerald. “Fitzgerald’s unfinished final novel is obviously not his only work about the complexities of achieving the American dream, but movie magnate Monroe Stahr is no Jay Gatsby. Based loosely on Hollywood legend Irving Thalberg, whom Fitzgerald admired, Stahr is a genuine talent who fully deserves his success—and a decent and honorable man to boot, an even-rarer type in American literature than it is in American life.”

The Toothpaste Millionaire, by Jean Merrill. “Of all the great children’s books about entrepreneurship and marketing—well, actually, this might be the only one. Two Cleveland sixth-graders realize that they can undercut Big Dentifrice by mixing up baking-soda toothpaste in their basement. In the end, their success gets a bit ahead of them, just as it was with so many of the real-life tech billionaires they probably inspired. Merrill is better known for another ingenious business parable, The Pushcart War, in which New York’s food cart vendors battle their natural enemies, big semi trucks, armed only with tire-deflating pea-shooters. But a lot of my book choices were already looking a bit ‘pink’ for Businessweek, so I went with the mini toothpaste capitalists instead.”

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