“He was on holiday in the Caribbean and decided he wanted to have his dogs with him so he chartered a private jet for them.”

"He was very easy to relate to, great to work with and — having earned his wealth — he understood what it was like not to be wealthy. Occasionally, however, the vast difference between the genuinely rich and the rest of us showed… A couple of examples that stand out:

When Wimbledon was on, he was leaving work early on a Friday. I happened to ask him what he was doing at the weekend. He mentioned he was watching the Wimbledon men’s final, as Andy Murray was playing — the first British male finalist for ever. I said I’d be watching too and asked where he was going to watch it… He was going to Wimbledon. To Centre Court. With tickets he’d decided to buy on spec when Murray won his semi-final. They’ll have been at least £20,000 each.

"Once saw a rich person's son go buy a £100k+ truck to move a bed because I wouldn’t let him borrow my pick-up. Fun fact: I didn’t know him; I was in the neighbourhood visiting friends."

"There's one homeowner who does that anyway, and just pays a probably five-figure fine every year as a cost of business. So, from his house, probably 100 yards from the river, he can see across the river to the trees on the other side.

I kind of feel like eventually, knowingly breaking the same law repeatedly every year should stop being a fine that's probably just a rounding error for this guy, and more like a go to state prison thing."

"He was on holiday in the Caribbean and decided he wanted to have his dogs with him. So he chartered a private jet for them because he didn't trust airlines to make sure they were safe in the cargo hold.

I can only imagine the crew getting the passenger list and being like, ‘Uh… so… it's just two dogs?’

A lot of examples are people buying ridiculous stuff and showing off, but I really liked the idea of being like, ‘My dogs would love this place. Fuck it, I'm going to spend $20k flying them down so I can watch them have fun.’"

"After about two years, we got a new manager, and we had to say that, as a chain, we're limited to what we can keep adjusting, because stock is controlled pretty heavily, blah blah blah.

The matriarch just said, ‘Oh, that's a shame, we'll take our business elsewhere.’ They bought a building less than a mile away and turned it into a country pub, and they employ staff to run it so they can eat there every week.

Crazy waste of money when they could have hired a chef to come to their house, but I guess they want the traditional pub feel for their family meals."

"The boyfriend ordered three shots of Johnnie Walker Blue with picklebacks for him and the other two guys (he didn't offer me one). JW Blue is a decent but overpriced Scotch, $75 a pour at this particular place. A pickleback is a shot glass of pickle brine. I asked Dr. Boyfriend what the point of it was. He explained that the idea is to down the whisky in one shot, then immediately drink the pickle juice to, in his words, ‘kill the taste of the whisky.’

So, basically, the only reason he ordered JW Blue instead of something cheap was to show off that he could afford to drop almost $250 on drinks."

Additional thumbnail credits: Warner Bros. Pictures, Warner Bros. Pictures