I know a guy who rented a whole mountain—in order to climb it 17 times in a row
Usually when you hear about the rich and famous buying a mountain or a private island, it's with the idea that 1) it's a status symbol and 2) you can resell it later on and, hopefully, make a profit.

But who would just drop a huge sum of money to rent a mountain?

My friend, Jesse Itzler.

You can't call him old money or new money. He's really more "experience money."

Ever since I've known him, Jesse has been into crazy stunts and challenges. He once ran 100 miles straight in under 24 hours. He also spent weeks on a monastery living with monks to test himself mentally. And then there was the time he jumped into a frozen lake with a Navy Seal that he'd hired to live with him for 31 days.

I sort of think of him as a modern day Evel Knievel.

So it came as no shock when he mentioned he was planning to rent Stratton Mountain in Vermont for a few days in October for a new challenge.

"Of course you are," I said. Being friends with Jesse, you come to expect this sort of answer when you ask, "So what are you up to these days?"

This time, Jesse got the idea that it would be fun to see if he had what it would take to climb Mount Everest — and invite others to take the challenge as well.

Of course, for most of us, we don't have the time or money to go to Everest. According to a Time Magazine article, "The Economics of Everest," you're looking at $8,000 for training, $10,000 on gear and a range of $35,000 to $100,000 for the climb. It takes a few months. And of course, it's extremely dangerous.

So, Jesse decided to bring the Everest Challenge, or 29029 as he calls it (the elevation of Everest), here. He did the math: Hiking Stratton Mountain gives you an elevation gain of 1,750 feet. So, you'd have to go up it 17 times in order to reach the equivalent of Everest.

Jesse won't say how much he paid to rent to the mountain, but the fee is $3,500 to join the challenge and he's capped it at 150 people. If you do the math, that's $525,000. And, then you have to subtract the amount he's spending to create a base camp at 1,800 feet – there's a village featuring bands, bonfires, inspirational speakers, food trucks, sports drinks and adult beverages. (And, of course, tents.) Jesse describes it as "Burning Man meets Iron Man."

Participants have three days to try to reach their "Everest." Jesse says Grizzly Adams could do it in 25 minutes, if you're really in shape, maybe 45 minutes and someone who's in decent shape, it would probably take an hour. So, 17 hours, give or take, spread over three days.

Naturally, the event has piqued the curiosity of more than one Wall Streeter.

Robert, a hedge-fund trader said he's doing it, in part, because it's a personal challenge but also because it's a great networking opportunity.

"I'm sure I'll meet a lot of new and interesting people. I think it's going to be a lot of fun," Robert said. "I just hope I don't end up puking."

That sentiment was shared by other financial industry people who are planning to attend. "I think it's something I'll never forget," Mark, a bulge-bracket analyst said. "But I have to admit—I'm a little nervous."

Jesse thinks everyone who signs up is capable of completing the challenge, but he's curious to see who has the capacity/mental toughness to finish – and how they approach it. His guess is that some participants will try to complete it straight through, while others will use the full three days.

"It's not a race. It's you versus you," Jesse said. "But we live in America, so it's always a race." The person who finishes first will have the World Record because it's never been done before. (On Wall Street, we call that a dare.)

Jesse's a little more heady than that.

"I learned a Japanese ritual from Kyle Korver," who used to play for the Atlanta Hawks, Jesse said. (Jesse's a part owner of the team.) "The idea is to do something really hard on one day of the year, something that challenges you so much internally. If you can accomplish it, the power of the experience will pay dividends for an entire year."

Tune in to CNBC tonight (Tuesday, Sept. 19) at 10pm ET/PT for "The Filthy Rich Guide." Turney Duff comments on lifestyles and purchases of the filthy rich.