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My Ten Most Outlandish Expenses

on May 03, 2021
An excerpt from “The Autobiographical Account of the World’s Most Controversial Employee”

You see, it’s a common misconception that the world’s most remarkable artists are painters or sculptors. But making art – being an artist – is nothing more than the act of capturing perfection. And so, there are artists in every walk of life. I consider myself such an artist.

My canvas, as it were, is the expense report. And though you won’t find my name in magazines or elsewhere in the halls of history, I must admit that my work is simply breathtaking.

For a great many years, I carried on in this way, carousing about the country in first-class seats, eating and drinking mightily at the finest restaurants and generally living high on the hog. The company at which I was employed was as flush with cash as it was lackadaisical in its expense reporting systems, and nobody knew it better than me. And I mean nobody. It was as if I had a magical, unlimited card whose bill never came due.

What did it buy me, you ask? Well, everything, of course.

Ready to experience a few of my greatest tales? Read more for my top 10 expenses:

Ye Olde Liquor Switcheroo

My introduction to the power of an unchecked expense report came in the form of a covert offer, whispered by a bartender at my favorite watering hole. That glass of Pappy Van Winkle I’d been eyeing could go down on my receipt as Office Supplies, a timely idea for a tasty treat. My dinner? A fine cut of Kobe beef they’d aptly named Printer Paper.

Upping the Ante

Seeing that I could indeed expense away my occasional taste for the finer things, I thought it wise to invite more of my friends. Though the details get blurrier as the fog of fine whiskey and wine washes those fateful nights, I can recall with great aplomb the steak dinners tallying into the thousands, the $500 rounds of shots for the entire bar and indeed at least once I can admit to slumming $1500 at McDonald’s with, well perhaps 150 of my closest friends.

Viva Las Vegas, I Always Say

When you have access to a corporate-sponsored lifestyle, it seems silly to waste it at home. Particularly so when your closest friends are engaged to be married. With nuptials on the horizon, we set for Las Vegas for a week of gambling, drinking and otherwise celebration, all on my company card. It was me, the groom-to-be, and 200 of our colleagues and friends. A true test of the expense reporting system, I admit, but one that once more proved my unlikely power.

West Coast, Best Coast

Amidst a lofty debate on America’s great golf courses – and by now on our third Office Supply – we agreed then and there to set course at first light for an impromptu tee time at Pebble Beach, courtesy of my corporate card. Perhaps because of the whirlwind nature of our trip, I recall leaving home without sunglasses. Staring into the rising corneal threat of the California morning light on my whiskey-weary, east coast eyeballs, I purchased a second pair on my way out west for the lowly sum of $600. It was a trip for the ages.

Super Bowl Winners and Disney World; Name a More Iconic Duo

And who could forget our jaunt to the Super Bowl? It was a trip fit for a king, first-class all the way. We wined and dined and bought drinks for the entire bar just to make an impression on our guests. And when our team won? We all set course for Disney World together, on a whim! It was then that I was most thankful for my unchecked expense reports. I only had to expense an additional $10,000 to celebrate like an MVP.

Showering Love on my Tiny King

When I returned home from Disney World, I assure you no one was gladder to see me than the true world traveler among us, my dog and copilot, Baxter. After admonishing me for being gone for too long, we traipsed off together for a dog pedicure and lunch, where I ordered and expensed us each an entree. And then I used my corporate card to pay my full-time dog caretaker, whom I’ve put on my expense account since learning of Baxter’s distaste for boarding.

A Regular Wildlife Sanctuary

As Baxter will tell you, I love animals. I’ve expensed monkeys, racehorses and the car repairs needed when an elephant sat on the hood of my rental car. There’s no expense I won’t afford for the friendly little creatures of our world.

Softails, for One and All

But the day I realized the true power of my expense report was the day I bought everyone in the office a motorcycle. The joys of the open road. The creativity that springs forth from a wind-whipped commute. The exhilaration when the first two of your 400 horses in power are named Harley and Davidson. What an expense! What a time to be alive!

The Lap of Luxury

If I can expense a few dozen Harleys, what is stopping me from the finest bottles of wine? $1,000 per bottle? Uncork it! Lamborghini dealership? Swipe away. Private jets! Half million-dollar watches! The world is our oyster, and the expense report is us, polishing the pearl with paperwork destined for a rubber stamp and a drawer somewhere.

You Think I’m Setting Records Here? Try Again. 

After all, I’m just the world’s most terrible employee. A middleman. Now, my bosses? There is a group that has it all, and then some. Indeed, I was there when they bought a yacht just because. The ship’s captain? Put her on salary! Because when it comes to expensing your wildest dreams, it’s not enough to have a racehorse when you can buy the whole polo team and let payables sort it out.

Yes, I know what you’re thinking: world’s most controversial employee, how did you get away with it? Well, the answer my newfound friends, is that in the long run, I didn’t.

Along came the software to “bring attention” to my “unusual expenses” and my “patterns of non-compliance.” Where once our corporate auditors pulled small samples of our expenses manually to look backward at our reports long after they were filed, suddenly there was real-time monitoring, and a well-oiled machine looking over my shoulder before my expense reports were even processed. Whoever was pulling the strings was crushing the status quo.

It didn’t take long for the board of directors to see that my boss and I were indeed the world’s most terrible employees. Do you know anyone hiring sales managers?

**Not a real book, but all of these stories are based on real things that employees have tried to expense.

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