Inside Celebrity Spending: True Tales From Personal Assistants

If you’re not extraordinarily wealthy, you’ve probably spent some quality time daydreaming about having loads of dough. What’s it like to jet from LA to Paris on a whim or promenade The Croisette at Cannes? How great would it be to surprise Mom and Dad with a weekend trip to the Loire Valley? Let’s not get started on zillion thread-count sheets.

But for an inside look at how the rich and famous spend their cash – and at their attitudes toward spending that cash – some of the best sources are the people who spend that cash for them: personal assistants. They’re not just fetching sugar-free macchiatos. They’re filing their tax returns and picking out their parent’s anniversary gifts. Does wealth make people selfish and greedy, like the recent New York magazine article suggests? The assistants know best.

All industries have their idiosyncrasies, but the film industry can claim a very special brand of bonkers behavior when it comes to bosses behaving badly. Hollywood is full of lunch tables occupied by haggard assistants complaining that their boss a) threw a blunt object at their head, b) called them an “idiot” for not knowing the number for Gjelina by heart or c) threatened to fire them for buying the wrong shaped pretzel for their precious client – a client that probably never even touched the cursed, carb-riddled pretzels. These are true stories. Not all wealthy, powerful bosses are horrible. In fact, less power/more tyranny seems to be a pretty fair equation. Still, money can do funny things to people.

A common theme among the personal assistants I spoke to (all on condition of anonymity) was that their bosses spent lavishly when it came to themselves (the bosses not the assistants) or their makeup artist or trainer, but when the time came to buy gifts for their own flesh and blood and longtime friends, it was a different story.

“She once had me buy some luggage for her makeup artist, two bags for $5000, and yet for her best friend’s birthday she told me to find a used bike on Craigslist for under $100,” he said of a multi-million dollar actress. It’s the thought that counts but this is your best friend, right? He also said that the actress’ mom needed a new TV, but instead of buying a new one she had him dust off an old TV that was missing a remote in her garage and drive it over to Mom’s house. Now, maybe this actress didn’t care for her mom – it happens – and a makeup artist can be an actor’s real BFF, but this tendency seems to be a recurring theme.

“Yes money mattered to her,” he went on. “She seemed to want to flash it with inconsequential people, but with family and friends she was extremely frugal.” Another assistant to a well-known actor also noticed similar attitudes towards spending. One minute she would be frantically chartering a jet for her boss, or arranging $10,000 a year in doggie daycare stays, and the next she would be ordered over to the 99 Cent Store to pick up some items for charity. “For gifts for the kids’ teachers or friends he would have me shop at Rite Aid,” she admitted.

People can spend however they want, obviously, but it’s enlightening to hear about these habits. It illuminates what’s important to the people doing the spending. Makeup artist before Mom, or pooch before teacher. This assistant also got to shop at Neimans and Prada, “not that I paid with my own money of course,” she joked. “It was kind of fun,” she said of browsing Beverly Hills shops. “People would sometimes think it was for me, and I was like ‘I’m just picking up a bag for my boss’ wife,’” she continued. If they caught on that she was the assistant, the preferential treatment quickly disappeared. “That scene in Pretty Woman is very true,” she admitted.

We all know extreme wealth can lead to eccentricity. Howard Hughes and his germ phobia, Big and Little Edie and their decaying mansion – the list goes on. Any of us could fall victim to the “crazy rich person” persona if someone threw enough money our way. A third former assistant I spoke to said that his boss “did not like change.”  Instead of finding a new pair of shoes, she would have him spend his time on the clock searching for a pair of discontinued sneakers that “fit her foot size perfectly from ten years ago or a deodorant she couldn’t find (anymore).” He would comb eBay for discontinued items she had to have. Some bosses think this is money well spent. “When I turned in my timecard… she would doubt my hours. That sucked,” he admitted. He would have to sometimes explain to her exactly what he’d done on certain days. Clicking through eBay for shoes was OK evidently.

Did money matter to this creature of habit? “It mattered,” her former assistant said. “She wanted to be a good example to her kids and it seemed like she had something to prove. But she didn’t do anything about it.”  So does all of this make these moneyed bosses selfish, or hateful, or mean? The answer might just depend on whether you’re the makeup artist or the Mom. Another former assistant says her actor boss was actually very generous and hard working, despite their “astounding” wealth. He “laughed at the celebrity-ness of it all,” she said. Even though he took his good fortune in stride, the assistant sometimes wondered how a person could keep their cool with that kind of money. Like many assistants, she dealt with his bank accounts and taxes. “You see the amount of money and wonder how they weren’t ping-ponging around with glee,” she admitted. They probably did ping-pong around gleefully at some point. Then they got used to it.