Love Tough Mudders? Then You Have to Try ‘Everesting’

The sun is still below the horizon and the temperature barely above freezing when Jesse Itzler gears up to ascend a black diamond ski slope. “We’re going into the clouds!” he exclaims, eyeing the snow-covered summit of Vermont’s Stratton Mountain, which is ominously concealed by dense fog.

Never mind that Itzler, a 51-year-old serial entrepreneur and former rapper, has enough money in the bank that he never has to work another day in his life, let alone scale a mountain on a chilly October morning. He’s out here anyway, clad in blue shorts, a wind jacket, and a headband, accompanied by roughly 200 others who range from veteran endurance athletes to people for whom exercise is more of a goal than a habit. They’ve all paid about $4,000 for the privilege of joining him.