We've all heard the phrase "money is no object." Well, these people take up a notch. Or ten.
How Much Cable Is Too Much Cable?

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I work for a luxury home builder. Very big, very expensive houses. We are building a home for this guy & he calls freaking out at me because AT&T would only provide him with 9 DVRs when he needs 11. They would provide him with more, but he would need to open a second account to do so. I don’t know why, I guess they had some kind of weird limit at the time. I’m the CTO of the homebuilder, so he expected me to get AT&T to change this policy so he could have a TV with DVR in every bathroom as well as the normal TV-viewing rooms. I obviously couldn’t do this, so he cancelled his contract with us through his lawyer & never spoke to us again. His deposit was non-refundable, in fact we had already spent most of the money on the initial part of the build. So he walked away from over $100,000 we wouldn’t give him back without ever saying a word to us. It was no biggie to him I guess. It also made NO SENSE. (Source)
This Guy Really Wanted Internet

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So, this is obscene, but not really in a hugely bad way. Many moons ago I worked at a cable company. This guy calls in because his internet sucks. Sadly, there was about f_ck-all we could do about it as his home was out in the boonies. We could only get him internet through a wireless tower, and those things will have connection hiccups if a butterfly passes by. He asks us how much it’d cost to run a wired line to his house. At first, we assumed he was either: a) stupid or b) crazy. Turns out he was serious. We got a contract put together in a few days and he paid for a new line to his place, which let us run connections to a few other houses in the area. I can’t remember if it was a 7 figure or 6 figure deal, but that sh_t wasn’t cheap. So, hats off to crazy old rich guy in bum-f*ck-nowhere. I hope your porn streams are still flowing like a river. (Source)
Weird Gifting Laws in Dubai

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My boss was a military liaison in Dubai and told me a story about a guy he became friends with there. One night they are driving back from a night of debauchery in this guy’s brand new Ferrari and it breaks down. He pulls over to the side of the road, gets out and starts walking while calling his people to come get him/bring him another car. He doesn’t mention anything about the broken Ferrari so my boss asks him about it. His response was “what about it? It’s broken. I’ll just buy another.” People have stupid amounts of money in Dubai. (Source)
One Guy Transformed an Entire Town

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My hometown of Hobart is a working class city right at the end of the world in Tasmania, where nothing much ever happens. In the past not many people came here except a few hikers / outdoors people to admire the natural beauty of the place but that’s about it. A guy who made hundreds of millions of dollars gambling opened his own private $150 million art museum, and has turned the city into a major tourist drawcard. Best of all, locals are allowed in for free whenever they like, and free parties/festivals are thrown year-round. In under 5 years he’s single handedly transformed the entire city. (Source)
Invisible Renters

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I was helping an owner rent his apartment, which is an investment property. It’s a 2,500 sq ft condo with 4 balconies and 360 degree views of midtown east in Manhattan asking for $15,000/month. Rented it for 6 months upfront with option to renew to someone who has ties to oil families in the Middle East. The person never moved in. (Source)
That’s High-Stakes Gambling!

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We owned a karaoke service in Las Vegas. Got a call one day at 7:30pm from a party planner we often worked with. They wanted us to be at the Venetian in 1.5 hours for a 4 hour event. “Price is not an issue” We gave them a decent last minute deal ($2000). Turns out this was for a private gambling club. They had a special room with the big table games set up. Minimum buy in just to attend was $500,000 actual cash on hand and another $500,000 line of credit. Minimum bet was $5000 with no max. Most bets were $20k or more (a stack of 20 $1000 chips.) I forgot to mention, there was also a $1,000,000 membership fee (one time, lifetime) to get invited to these kinds of events. The smallest chip in the room was $100, and that’s what they used for tipping. I made over $3000 in tips that night, plus my pay of $2000. In 4 hours. Rumor was that one guy lost $3.5 million. In 4 hours. (Source)
My Other School Bus Is a Helicopter

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One of my students gets dropped off to school in a helicopter. (Source)
This Ain’t Your Mama’s Halloween Party

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A party at the CEO’s house for Halloween. Insanity. I thought I was going to get kicked out of the neighborhood because I was only driving a 30k car, not a 300k car. Anything you can think of, he had at this party – staff with signature cocktails at the door, a fully staffed bar for liquor, a fully staffed bar for wine, an entire table made of ice with ice shot glasses and ten different vodkas. He was wearing a costume made of leather that his wife commissioned for him, handmade in France. The 400 yard bridge to his private lake was strung up with extra lights, and the dock had a separate bar for those who wanted to sit on the lake. (Source)
Affluenza Gone Wrong

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I had an obscenely wealthy kid in my graduating class. His parents bought him a brand new Range Rover on his 16th birthday and he crashed it into a school bus. They got him a new one and he crashed it road racing. They got him a new one and he got a DUI and finally the police took away his license (thank the lord). (Source)
Loads of Shoes Aren’t Just for Women

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I work in a shoe store. I once had a customer walk in and say “give me one pair of every men’s shoe in a size 10.” Didn’t want to try them on or look at them, he just needed some shoes for each of his houses. I work on commission so it was a huge sale for me. But holy f*ck, man. That was about 140 pairs of shoes. (Source)
Those Must Be Fantastic Strawberries!

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I work for a wealthy man and he once had me fly on a private jet to the other side of the country to pick up 6 perfect heirloom strawberries that cost 100$ per six pack. They were placed in Chinese silk hand molded box so each strawberry wouldn’t be jostled during the trip. He ate 3 and gave me the rest for my trouble. Not gonna lie, it was the most amazing strawberry experience I have ever had. They probably cost him 25k all said and done between flights and my wage. (Source)
The Bentley Bounch

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My boss once had me drive him to an exotic car dealership to pick up his new Bentley… 3 days after my paycheck had bounced. (Source)
Kids Without a Care

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I once won a VIP ticket for a Moscow night club (don’t ask). I saw three kids test the waterproof capabilities of their 100k watches by emptying 4k bottles of champagne over them. One of the watches wasn’t, and they found that fact very funny. (Source)
Wearing Something That Costs More Than 10 Houses

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I met the CEO of the company I work for and I complimented his watch. The first thing he did is take it off for a day to let me wear it. Come to find out after doing a little research, the watch he was wearing is a Patek Phillipe that cost $1.75 million. That watch alone cost more than every asset in my family for the past 4 generations. (Source)
Location, Location, Location

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A guy who moved 300 miles away just so he could buy a plane to fly to work every day. (Source)