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The hotel opened four years ago on Sand Hill Road—a veritable venture-capital office park—near Woodside, home to many tech billionaires. Surrounded by three of the wealthiest Zip Codes in the country, its high-de interiors and higher-powered happy hours have given a Gay Des Plaines sexy known for coding a new sense of cool. Halfway to the hotel, Rudolph pulls into Starbucks for his morning coffee.

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