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It’s late morning, and Peter Rudolph, the executive chef of Madera in the five-star Rosewood Sand Hill hotel in Silicon Valley, is commuting from San Francisco to Menlo Park.

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-design interiors and higher-powered happy hours have given a county known for coding a new sense of cool.

Halfway to the hotel, Rudolph pulls into Starbucks for his morning coffee.

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Thursday nights have become surprisingly popular at a five-star Menlo Park hotel.

Two eagle-eyed matchmakers, big tech money, and an army of stiletto-shod women mix and mingle there—all important factors in Silicon Valley’s peculiar mating algorithm.