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When Peter Thiel ventures outside for a run, typically in the early-early morning, when the fog drifts low and slow into the San Francisco Bay, he's often drawn to what the poet Lawrence Ferlinghetti called "the end of land and land of beginning." That means the San Francisco waterfront—especially the one-and-a-half-mile stretch of pathway hugging the marshy shoreline from Crissy Field to the base of the Golden Gate Bridge. Aesthetically, the appeal is obvious—a postcard view of the bridge and the bay, the lapping tidal rhythm, that sort of thing—but for Thiel, a 43-year-old investor and entrepreneur whose knack for anticipating the next big thing has yielded him a $1.5 billion fortune and an iconic, even delphic status in Silicon Valley, there's a symbolic angle as well.

