From 2000-2004 I worked for a pretty small start-up company. The CEO was a super down-to-earth, open door policy kind of guy. He knew me (and likely everyone else) on a first name basis. Just an all around good guy. Fast forward to 2007. This CEO, now at a different company (he had sold the one I used to work for) called me out of the blue because he knows I dabble in video production (that's how good he is - a CEO of a 700 person company, and he remembers a hobby of mine). He needed me to do a video project for a group/club/organization that he is a member of. I gladly accepted the work and he put me in touch with the person that I would collaborate with.

That's where this story really begins. I was hired to do video interviews with several individuals who were "graduating" from this club. The group is called Young Presidents' Organization, or YPO for short. You can read about it if you'd like, (http://www.ypo.org/why-ypo/) but essentially, it is a organization where young (under 50) CEO can network and exchange ideas. They also socialize - going on pretty elaborate trips all around the world. Most of them are bankers, equity investors, some tech CEOs, but mostly just "money people". These are the guys that buy and sell 35 million dollar companies like you and I buy a pair of headphones.

I begin filming these people, mostly men, in their homes and offices, and even one in the cockpit of his personal jet (more on this character later). The first year I did this, I was just enjoying myself. I'm getting paid to do video work while seeing amazing architecture and design in these peoples' homes and offices. I'm getting offered bottled water by the most beautiful women outside of New York fashion week. It was a little view in to how this segment of the world works. Then I edit the footage together and show up the night of their annual party and press play on the DVD player.

I've done this for four out of the five last years. Every year, I get to meet more of these people. Some of them I have interviewed more than once. Some of them are really cool, very down to earth people who have done very well for themselves because of good ideas, good timing, good luck, or good heritage. But there are some that are straight up douchebag. Speaking in generalities, it's the old money that are the bad ones. And you can tell the difference between them pretty quickly in conversation.. more on that later (see point 4).

In my experience with YPO, I've noticed a few common characteristics:

1. Trophy wife. It's sad, it's predictable, but it's true. With one exception, every wife there was 10-30 years younger than the YPO member and a size 0-1. Not as many were blonde this year. Last year it was a blonde year. Brunette must be the new blonde.

2. Eccentricity for eccentricity's sake. - these guys become pilots because they have nothing else to do with their time. They go to Las Vegas and race Indie cars because they can. They buy expensive art… because it is expensive.

3. Double-standard for "late" - I showed up about 10 minutes early for an interview this year at a local executive jet terminal (frigging cool) to interview a guy in the cockpit of his helicopter (see point 2). At interview time his administrative assistant notified me that he was running just a bit late, and that he would still need to get the helicopter out of the hanger, and then fly it over onto the tarmac where we could shoot the interview. 20 minutes later he shows up, gets his chopper out of the hanger, goes through the pre-flight procedures and checks (I can see this from across the tarmac) and then flies over to where I am. It's now 45 minutes after the interview time - now don't get me wrong, I'm sitting in the most posh little lounge flipping through this month's Private Jet Lifestyle magazine: http://www.elitetraveler.com/ and sipping a coke. He finally shows up, I walk out on the tarmac, shake his hand (we've met before, but he wouldn't remember) and proceed to set up for the shot. I'm no uber professional, but you know, there are mics and lights and lens changes and tripod adjustments, and compensating for the noise from the nearby jets idling and white balancing and all kinds of things that take me about 15 minutes to set up. About 4 minutes into the set-up, while reading mail on his smartphone with reading glasses outside of his sunglasses (yes… actually at the same time) he looks up at me and says "is this going to take long?"

4. Inability to be social with "the help". To continue the story from above, pilot boy almost immediately followed his question with "I mean, I know I was the one who was late…" and then continued stammering about something, but I just kind of ignored him. It was like he was a pompous prick, but he didn't mean to be? It's like he knows how to deal with other equity investors, CEOs and people of wealth, but lacked basic social graces with "lowly normal working people". I didn't take offense. I think I almost felt bad for him. It was like watching some one with Aspergers. He didn't mean to sound like a douche - he just doesn't know how to talk to people of lower social standing. A different example came from one of the trophy wives. While setting up the equipment for the shoot, she and her husband are talking to one of their friends (who is there to be interviewed after them) about the game "Words with Friends". She asked a question that neither of the other men heard, and when I answered her, she was a little taken back and said slowly and loudly (as if to a servant who barely understood English) "OH, YOU PLAY WORDS WITH FRIENDS?". I smiled and nodded while I fiddled with the audio recorder and choked back the urge to challenge her to a game.

Mind you, I'm really not complaining. I'm happy to bill them hourly rates (especially when they are late) and get practical experience doing a job that I enjoy. I have made some good connections with some of them. I have gotten some more side work from this. Yet each year, I go through this experience where I am in the midst of their collective wealth while I live in my humble reality. It's a strange and sometimes jarring juxtaposition. It takes me a couple days to process and file away what has happened. As I was processing today, I think what got me was the following paragraph from their website:

"Leading a company is energizing, challenging– and often lonely. Isolation can be part of life at the top, so YPO provides the confidential sounding board you need: Forum."

I dunno - it just shook me a bit. I mean, I guess I get it a little. In a traditional company, it could get lonely at the top. It could be isolating, but knowing these people, and knowing their inability to connect with the "common man", I would think that the last thing they would need would be MORE exclusive contact with people like them. The social scientist in me thinks that this club serves as a artificial insulator that keeps them out of touch with the lives of the rest of the population. I get it. I guess I just don't like it. I don't really want their money, cars, trophy wives, or homes… okay, maybe some of the homes (I'm a sucker for architecture). I think for the YPO members that are grounded - it's a good thing - it puts energetic, intelligent, entrepreneurial people together with investors that have money, which can foster growth and create jobs. But I think for some of the old money (the great grandson of an oil man who's who family has been in oil and gas since) it just maintains a social and economic gulf that keeps them comfortable. Anyway, back to the anticlimactic story.

So there I am last night. The event is in a swanky lounge in the lower lever of the opera house downtown. There is more top shelf liquor at the open bar than most regular bars have in their storerooms (perhaps it's a shame I don't drink). This isn't really a party, it's an event.; a gala. Not that they are dressed up in tuxedoes - but the women are certainly dressed to the nines. I show up early to do a soundcheck and make sure everything is going to work - then I wait. the party is still a few hours away. I wander the opera house admiring the art, the architecture of the building, the historic costumes hung on the wall for display. The party begins and I wait for my various cues to show the videos and that's when it hits me…

I could get a hold of the local Occupy movement and tell them about the event. There's one kid sitting at a nondescript door who can't weigh 150lbs soaking wet. What's he going to do if a mob of 200 angry Occupiers storm the party? He might just join in. I had visions of project mayhem in FIght Club. I smile to myself.

That idea bounces around my head for a while before I realize it might be the dumbest thing I've ever thought…. but it would have been entertaining.

maybe next year...