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Expense Reporting Horror Stories
Expense Management

Expense Reporting Horror Stories

12 min read

At Divvy, we’re all about streamlining business spend. The finance leaders who come to us are fed up with their current expense reporting processes. Not only do they have to deal with messy paperwork and manual data entry, they have to deal with employees expensing ridiculous items—and expecting to be reimbursed. 

These are our favorite expense reporting horror stories: the reimbursement requests you never saw coming.

(Disclaimer: While these stories are entertaining, they’re also a little embarrassing. Save your company from writing a horror story of your own and try Divvy.)

13 Real-life expense reporting horror stories

1. Pick up your severance package and keep the boat

Matt says, “I knew a guy that purchased a boat on his company expense card. It not only went through, but they were on their way out, and wound up getting fired, and finance decided it was going to be too much of a hassle to try and recover it so he wound up keeping the boat. 

Had I known that, I would have bought a boat and quit too.

His co-worker, Stephen, confirmed and added: “That really happened. I thought it was a truck and a boat…because boats don’t pull themselves!

2. Everyone loves a good slasher movie

Austin says that he paid for and got reimbursed for his boss’ vasectomy. “Still takes the cake.” 

Expense Horror Stories

3. When a dog sitter calls

Two different employers received expense reports for dog sitters. Jenifer says, “We had an employee expense dog sitting since he had to travel for a few days.

Tara says, “I worked at an agency that was getting recognized at a big partner trade show. To celebrate, the company invited all 35 employees, many of whom were fresh out of college. One person charged their dog boarding to the company card and couldn’t believe it was rejected.

4. Eye scream, you scream

From Stephen: “One of my college jobs was as a purchasing clerk for the university. The science department made some weeeeeird purchases. The one I remember the most was three cases of pig eyeballs (I don’t know how many eyeballs were included per case).

5. Til death do us part

Sterling says, “I heard of someone who paid for their wedding on a corp card…and got reimbursed!

6. Skin and bones

Todd’s experience resulted in an unpleasant conversation for him: “I had a sales manager use his company credit card to take his team to a strip club. Certainly the most awkward termination I ever had to contact.

Expense Horror Stories

7. Haunt your own home

Alexander says, “Someone from investors relations had his first floor of the house painted and redecorated because he ‘couldn’t entertain clients in the condition the house was in.’

8. Here for the boos

From Elliot: “About 20 years ago, I had a dinner meeting in San Francisco with our CEO and our PR professional. The dinner was in the restaurant on the first floor of the Carlisle, a small, boutique hotel, recommended by one of our board members. 

Along with our meals, the CEO and PR guy ordered a bottle of wine to share and I ordered a glass of Sprite.  My Sprite glass was short and slender with four large ice cubes filling it, leaving room for only three or four actual swallows of beverage. As the meal and meeting continued over 90 minutes, I asked the server to refill my drink six times. 

When we received the bill, we learned that those Sprite refills were not free and each glass of Sprite had cost $7.50. So my personal drink tab for seven tiny glasses of Sprite was $52.50, more than the bottle of wine the other two had shared. 

It was hard to explain to accounting when we returned, but at least I had witnesses who teased me about it for some time after.

9. Trick-or-TNT

At least Matt had fun with this crazy expense: “I expensed a case of explosives for a team building video shoot. Each team was given a budget to do a team video to share with everyone and our team decided to get some Landesk Product boxes and blow them up. So I ordered some Tannerite and expensed it and the bullets to blow it up. I was a little nervous submitting that. It was less than 100 bucks though, so we were WAY under budget and nobody cared.

10. Don’t be a chicken

Daniel says, “I worked for a company previously that had an employee who was notorious for interesting expense reimbursement requests (think car payment, car wash multiple times a week, custom swag, expensive coins, etc). ⠀ 

At some point, we noticed this person ate at Chick-fil-A way more than any other restaurant. Eventually, we made a game out of it, guessing how many times they ate at Chick-fil-A in a week…It was almost always more than five times a week (multiple times a day).

Expense Horror Stories

11. The cask of Amontillado

From Gabe: “One of my favorites is an employee trying to submit an expense report for a dinner. She had spent around $350 for herself and was having a hard time understanding why we were declining the majority of her reimbursement. Once we got a hold off the itemized receipt we found she had purchased a modest dinner and a case of wine. 

The dinner was reimbursed, but not wine much to the employees dismay. We had to reach out to that department to re-educate them on the meal policy.

12. Flight fright

While Alexander’s expense might have been justified, it was still a bit ridiculous: “A new analyst who started to cover the Brazil markets had to fly down to Brazil for a week because he’s never been to Brazil and how could he cover a market that he has never been to.

13. Double, double, toil and trouble

And finally, Brian shares, “A coworker took eight people from the UK office to dinner, and paid for entertainment on it, as well as a $300 tip (in 1998). Total bill: $2,500. Entertainment? Lap dances. Expense was declined and he had to pay the entire bill on his own.

Have you experienced an Expense Horror Story of your own? Save yourself from future nightmares and try Divvy—the free platform that says R.I.P. Expense Reports.

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