Personal Assistant Tips: Paying the Bill (When Working for Celebrities & Billionaires)

When working with billionaires, PAs need to have a lot of cash on hand


If you work for a VIP, celebrity, or high net worth family, paying bills needs to handled with discretion. It is not uncommon for ultra-exclusive restaurants to charge $500 or $1000 per person. With six people in your party eating the most expensive items on the menu, and adding a bottle or two of rare wine, the bill could easily be $30,000. Most personal assistants will never get to experience dinners like these, but I was fortunate enough to get to with the Royal Saudis (Click HERE to see a list of desserts that range from $14,000 to over 1 million dollars).


When I felt the dinner was winding down, I would excuse myself and ask our server for the tab. I would then diligently go through each line-item on the bill to make sure everything added up properly. Because I usually tipped 20%, I always put the wine on a separate check. If, for example, a bottle of wine was $15,000, I’m certainly not going to tip the waiter $3000 for pulling the cork out of the bottle. So the 20% came off of the food items.  By the way, I cleared this policy with my boss and he agreed.


Being meticulous with the paying my various bosses bills, especially with the Royals, saved my employers a lot of money. When I had large Saudi groups staying at 5-star hotels for weeks or months at a time, the tally could easily be in the hundreds of thousands. This opened up all kinds of fraud opportunities for the hotel staff.  On more than one occasion I caught hotel employees adding services to the bill that were unauthorized, like massages for example ($300 a pop).


You may be asking yourself what the employees got out of it. It’s simple: kickbacks. Many stores in hotels: gift shop, valet parking, dry cleaners, and salons are usually independent contractors.  They just rent space from the hotel.  Anyone at the front desk or concierge can do what’s called a “paid-out,” which means they give cash out of their till (usually they have $2000 on hand at a 5-star hotel) to cover an order that the hotel guest  requested.  Simply put, if the charge is fraudulent, then the hotel staffer is keeping the money and forges the signature on the “paid-out” slip.  That signature can easily be copied because it’s on the registration card the guest signed when they checked in to the establishment.


Because the final bill could be as thick as a phonebook, some unscrupulous employees counted on the fact that busy rich people aren’t going to take the time to scour the invoice with a fine-tooth comb.  What the sneaky hotel clerks never counted on was my overzealous need to please my boss.  On the few occasions I did catch employees trying to skim, and my boss gave me a reward for the recovery of his stolen money.


To be fair, I also caught our own staff members trying to steal as well.  I had to fire one security guard who had over $4000 in unauthorized charges.  I took that amount out of his last paycheck.  The same is true for the car rental companies.  Sometimes we had up to 20 cars rented at one time when visiting a major city like Los Angeles.  So the general manager of the car company would throw an extra Rolls Royce Phantom on the bill (at $3000 per day) and hoped I wouldn’t notice.  On one occasion, the manager tried to pay me off not to turn him in.


Sometimes I attempted to save money on the front-end as well.  If the Saudi group was traveling to a city that gave me more than one choice for 5-star hotels, I met with the General Manager and negotiated a discount.  The GMs happily reduced the $10,000 per night Presidential Suite to sometimes half the price because they knew the entire group was going to be spending a lot of cash at the property.  On one occasion, our stay was over one million bucks!  Click HERE to see the world’s most expensive hotel suites.


Buy the PDF ebook with 97 pages of text, photos, videos and other resources: How to be a personal assistant