Tim Draper

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Outside the Office
Captain America vs. the Cape Buffalo

Between reviewing business plans from entrepreneurs, and meeting his investors to raise capital or deliver updates, Tim manages an amazingly diverse schedule. He speaks at business conferences, events and corporate launch parties worldwide in his own inimitable fashion, dressing up like Batman or a space man, once singing as he performed a video strip-tease, posing for a business journal in a spandex Captain America outfit, and for another in a bunny costume for reasons yet undiscovered. His wife introduced him to painting as a hobby, and he’s quite proud of a series of lobster portraits that hang in space of honor in his home.

An avid athlete, he skis on holiday, and still tries to make his regular 6AM basketball games with friends, though he says these days he’s abandoned jumping for “just shoving people around.” His sports interest sparked his personal investment in an independent professional baseball league, a challenge he says, to the “status-quo monopoly of Major League Baseball.”

Tim travels in rarified circles outside of work. He enjoyed visiting Neckar Island, Richard Branson’s private playground in the British Virgin Islands, and hanging with his fellow business leader. Draper had such a good time, he decided he simply must have an island of his own. So while flying in a private jet over Lake Tanganyika after an African safari, Tim spotted a pretty looking island to buy.

Typical to Draper’s venture capital due diligence, he worked with an expert local entrepreneur to qualify, close, and develop the property, now called Lupita Island. Tim bought a boat from “Bob” Mugabe, the dictator of Zimbabwe to use in the lake, had it trucked hundreds of miles only to find it was too big to fit through a highway tunnel. It had to be sawed in half and reassembled at the lake. For entertainment, Tim flies over the lake in his personal helicopter—and jumps in from about fifty feet. “The only rule for me and my friends there, is that there are no rules!”

And like Branson’s island, Tim rents Lupita out as an island retreat for couples or groups who want to “chill out” after a safari, for a cool $2,000 per room for the night. But mind the buffalo when you get to the mainland: Tim talks of the time he had to “juke out” a big-horned, two-thousand-pound angry Cape Buffalo that had chased him toward a tree during a walking tour. As a reminder, Tim has the mounted head of a “distant relative” of that buffalo by his office.

Continuing to enjoy both his business and his free time, Draper doesn’t see an end to his adventures any time soon. The businesses will change, the technologies evolve, but his passion and persistence will remain for the ideas and innovators that continue to “overthrow the status quo.”

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