When Jon Winkelried abruptly resigned from Goldman Sachs last year after 28 years at the company, there were questions. Questions about whether he had been pushed out by his co-COO, Gary Cohn, whom CEO Lloyd Blankfein had always liked better. Questions about Winkelried 's personal liquidity, since he chose to cash out his shares at essentially the worst time in history, when they were worth only a fractional amount of their value, and soon after put his $55 million house in Monomoy, Nantucket (known as "Money-moy" to the locals) on the market. But now, a year after his resignation, Winkelried comes clean to Fortune about the real reason he left.
He left because he was burnt out. Sick of the lifestyle. Tired of jetting around the globe and coming home to one of his four multi-million-dollar estates too tired to do anything but sink into a vast marble bathtub full of gold coins.
"I was about to turn 50," he says. "I was running around all over the place. This whole notion of 'Was I in the slipstream to become the CEO?' — I imagine I was one of two candidates, and I don't know whether or not I would have gotten it. But here's the important thing: It was no longer important to me. It just wasn't ... It changed for me somewhere. I don't know where."
It was time, he decided, to do something real. To become a cowboy.
Wait, stop: Winkelried knows what you are thinking:
"The question of how a suburban kid from New Jersey became a cowboy is one that Winkelried gets all the time. The short answer is that the family used to ski in Telluride, Colo., among other resorts, but grew tired of the crowds and the glitz."
What he wanted was to get back to nature. To get back to the land. Lots of land. All his.
Winkelried's love of fishing took him deeper and deeper into the backwoods of a number of Western states. After a four-year search for the perfect ranch, he and his family purchased adjacent ones in Meeker, Colo.: the Marvine and the Pot Hole.
He wanted to wake up and smell the earthy musk of manure, hear the whinny of a pony. Not just any pony. A prize pony. The best goddamn pony money can buy.
In 2005 he spent $460,000 on a stallion named "I Sho Spensive."
God, it sure feels good to be so far away from all that glitz.