The Most Outrageous & Hilarious Work Expenses Ever
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— Updated on 24 July 2020

The Most Outrageous & Hilarious Work Expenses Ever

— Updated on 24 July 2020
Sera Bozza
Sera Bozza

As the old saying goes, “it takes money to make money.”

Expense allowance typically “advance the development of respective business.” But there are some cheeky individuals who take a more “let’s see what I can get away with” approach. And we’re happy they did.

Software systems like Certify, manage travel and spending work expenses for companies worldwide. They analysed millions of entries over the last few years and have provided us with the goods.

There’s the typical flash of the corporate Amex for:

  • Gambling in Vegas
  • Strip club visits
  • Cigars
  • A tepee
  • Tattoos
  • Hot tub supplies
  • Porn
  • Watches and jewellery
  • Guns
  • Spa trips
  • Hotels for office affairs

Pretty standard, right? But even better than the claims themselves are the reasons given for each claim.

Beers ($100)
Liquid to maintain life in the tropics.”

Second computer monitor ($780)
I have two eyes.”

Armani jeans ($250)
Protective clothing for painter and decorator.”

A garden shed ($450), rental costs of the space it takes up in the garden ($650) 
For personal use.”

Hang glider ride ($2,000) 
To avoid a divorce.”

Boarding for a pet snake ($30)
Critical expertise needed with limited resources.”

Human skull ($800)
Purchasing skull for a medical experiment.”

Hyperbaric oxygen chamber ($5,000)
Went diving earlier.”

Separate hotel room for vegetables ($85)
I wanted a separate room for garlic samples; couldn’t stand the smell.”

llama rental ($150)
Photographer wanted a llama in the picture.”

Hotel maintenance $1,200
Repairing hole I punched in the wall.”

Helicopter ride to work ($6,500)
Needed to make it to a client meeting.”

Most of the work expenses above were approved. Not because they slipped through the cracks, but because often the cost of the claim is cheaper than investigating it and confronting the employee. Sometimes, it’s simply easier to give the go-ahead than investigate further.

Not to mention the fact that the policies themselves are often purposefully vague, confusing, and outdated. But there is a fine line between taking advantage via submitting multiple claims and fraudulent expenditures. The latter can lead to being asked to pay the money back or legal action.

Travel Writer, Karl Taro Greenfeld, recalls his fond memories of the golden days at Time Magazine to the LA Times.

Things can get overlooked when you’re bringing in a lot more than you’re spending, but some of the cases below were escalated to the US Financial Industry Regulatory Authority (FINRA).

  • Dareth Martin (Creech Financial Group)
    Charged for spending US$33,402 online shopping for clothes.
  • Tina Newman (Corby Capital)
    Charged for spending US$10,166.34 on her corporate Amex for a family vacation to Disney World. And for transferring reward points from the Amex to pay for her family’s flights there.
  • Matthew Kaplan (Lazard)
    Charged for spending US$4,950 on an escort service for his client who was having marital difficulties. He claimed the charge was for concert tickets to see Bruce Springsteen at Giants Stadium.

Needless to say, all three are no longer employed by those companies.

The most underrated excuse from all our research? “It just happened.”

RELATED: How To Deal With Your Asshole Boss.

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Sera Bozza


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