ONCE UPON A NIGHTMARE, two of my buddies, Kurt and Ed, took a flight to L.A. to meet with a few customers. While there, they decided to connect with a new colleague who was based on the west coast.
Now. Kurt and Ed knew the new guy, Jim, didn’t really need a job. His wife was a hedge fund manager and She. Was. Loaded. Like, “I just changed the rules of grammar to emphasize how loaded she is” loaded. Clearly, Jim only took the job to battle the boredom of being his wife’s eye candy.
Even with this knowledge, Kurt and Ed could barely pick their jaws up off the floor when they entered Jim’s $22M mansion.
For context, Kurt and Ed were the breadwinners in their families at $90K apiece. They’d started their days in two-bedroom apartments but were now touring Jim’s wine cellar, taking in Beverly Hills from the rooftop, and dangling their feet in a saltwater infinity pool.
Needless to say, Kurt and Ed were in heaven.
Kurt kept joking that he was going to live in Jim’s pool house, and Ed couldn’t stop counting the bathrooms. After a while, Jim got hungry, but said he didn’t want to eat at home because his private chef was “too chef-y.” The guys had no idea what that meant, but they went along with it.
They hopped in a cab for a bite to eat.
They did not, however, arrive at a casual sushi joint or vegan sandwich shop, as Kurt and Ed had expected.
Instead, Jim took them to some schmancy steakhouse. Think dark colors and leather chairs. The works. This was the kind of place guys go to show off their young girlfriends and old money.
The trio sat down and Jim immediately ordered a bottle of wine.
After two hours of eating and drinking from a menu that (conveniently) didn’t list prices, Jim stood up and went to the bathroom. Just then the waiter came by with the bill.
Without looking at it, Kurt said, “You’re expensing this, right?”
Ed looked at the bill. “Umm. I don’t think we can expense this one.”
Kurt looked at the check and damn near shat his pants.
The damage? $2,700. For three people.
Both Kurt and Ed knew that if they tried to expense a $2,700 dinner, their CFO would have a coronary. But they didn’t want to look like schmucks in front of Jim, so they scrambled to come up with solutions before he got back.
“Wait,” Kurt said. “Expense it. Say we took a group of clients out for dinner. They’ll never bat an eye and you’ll get it back.”
Neither of the guys had a company credit card and Ed wasn’t thrilled about throwing $2,700 on his personal Visa, but Kurt claimed he was too close to his credit limit and his card wouldn’t work.
Panicking, Ed reached into his wallet and pulled out his personal card just as Jim returned to the table.
“We good?” Jim asked.
“Yeah,” Ed said. “We, uh, we got it.”
Ed was a wreck the rest of the trip. He worried his wife would check their balance and be furious – and he was even more terrified the office wouldn’t buy the story about taking out a group of clients.
When he finally got home, his wife was…totally unaware. Damn near miracle. She hadn’t looked at the account yet.
Ed didn’t say anything, swiftly submitted an expense report, and prayed for the first time in fifteen years.
After two stress-filled, sweaty weeks, Ed was reimbursed 100%. His wife never found out, and, thankfully, everything turned out fine.
Moral of the story: whenever you’re taking colleagues out to dinner and they’re filthy rich, you pick the restaurant just in case.