Business Owners Tell All: What Are Your Scariest Workplace Horror Stories?

Avatar photo

Bat invasions, technology terrors, money mayhem – oh my! This time of year brings to light a whole new slew of terrifying tales about menacing monsters and spooky spirits, but perhaps the scariest stories are the ones that hit closest to home. For entrepreneurs, what’s scarier than something happening to your business?

In this edition of Business Owners Tell All, 11 entrepreneurs are sharing their most harrowing tales from the workplace. Be warned – these horror stories would send a shiver up any business owner’s spine!


business horror storiesI Accidentally Deleted My Company’s Website

I was hired as the marketing manager for a startup company and my boss asked me to update a few pages on the company website. I knew how to use our website editor so I was comfortable with the task at hand.

I logged into the website editor and saw a notification that said New Plugins and Software are Now Available: Click Here to Update. Naturally I went ahead and clicked the button to update.

The page refreshed and I was unfortunately greeted with an error message instead of a newly updated website editor. I refreshed a few times and kept getting the error message. I tried to load the website in a new tab and it said that the URL did not exist. Yup, I deleted and took down the company website.

We were able to get the website back up after a few hours but I felt terrible and wasn’t sure what to expect (I was hired only 3 weeks prior). Luckily everything turned out fine and I’m still the marketing manager at the company. My biggest takeaway is that when it comes to technology and software, if you’re not sure what you’re doing while using it, ask someone who does.

Travis Sevilla, Marketing Manager at GoShare



workplace horror storiesOur Website Fell to Page 10 Literally Overnight

In December of 2015, in the peak of the holiday sales rush, our website was hit point-blank with an SEO penalty from Google due to a negative SEO attack by a competitor. We went from ranking 1-3 for all of our top keywords to page 10 literally overnight. Sales tanked from thousands per day to a few hundred dollars, an employee was fired – it took months to recover (many sites never do), but as a result we’ve implemented intense backlink monitoring and ensure that we follow all best practices to a tee. I wouldn’t wish a manual SEO penalty on anyone.

Kiran Ravindra, Chief Executive Officer of Carbon Trim Solutions



workplace horror stories

My Former Boss Sued Me

When I think about mistakes I’ve made in the past, I have to look at the first company I had. After 16 years working for a cutting tool company, I decided to branch off and start my own cutting tool company. My former employer sued, alleging breach of a non-compete clause. Without the resources to fight the lawsuit in federal court, I had no choice but to shut down.

But I never gave up. A year and a half later, I was ready to start again, on my own terms. I worked night and day, mortgaged everything I owned, maxed out my credit cards, and just kept going. And here I am, 13 years later, with a multi-million dollar company that employs nearly 60 people. Don’t be afraid to fail, but never, ever give up!

Mike Moore, Owner of Wholesale Lanyards



workplace horror stories

I Sent Top Secret Information to a Competitor

What I suggest may seem minor, but it actually can have fatal consequences if not practiced. I religiously check email addresses before I hit the “send” button. A couple years ago, I accidentally sent an internal email – laying out my grand strategy of how to decimate the competition – to a key competitor. It was one of the absolute worst moments of my professional life. I decided I would never let that happen again. I preach to everybody who will listen to check the send-to email addresses before hitting “send”. I also made it official company policy.

Christoph Seitz, Chief Executive Officer of CFR Rinkens



business horror stories

Manufacturing Mayhem Made Us Miss the Holiday Season

Launching a new product is always stressful but when your manufacturer continues to delay your shipment it can turn into a nightmare. When I launched Ice Shaker, We were supposed to have our product in hand in October. We were all geared up to make a run during the holiday season.

Our product continued to get delayed and arrived the week of Christmas and we completely missed the holiday season. Never promise your customers a delivery date until your manufacturer has confirmed shipment of your product.

Chris Gronkowski, CEO of Ice Shaker


workplace horror storiesMy Office Was Invaded By Bats

I’m ready to leave the office, on time (for once!). As I go to open the door that leads down the stairwell, a bat appears! I saw it swish by my head and quickly ran back into the office. Being scared, I sat and waited for a coworker to leave . Since she wasn’t ready, She assured me that I should just suck it up and run quickly. She finally convinces me.

I saw the bat waiting right next to the stairwell door. I ran as fast as I could in 3-inch heels (of course) and I tried to open it quickly. All of a sudden, it BEELINED for my head, missed and bounced off of the wall beside my head. I swung open the stairwell door, only to see ANOTHER bat diving for the opening!

Needless to say, I screamed like a maniac and ran back into the office suite and waited two hours for someone to remove the bats. #worstworkhorrorstoryever

Kaitlyn McIlmail, Fashion Stylist at 7 Charming Sisters



workplace horror storiesI Made a Hiring Manager Cry in an Interview

When I was interviewing for a my first managerial position, I was instructed to have a power point presentation about myself and my plans on how to grow the business ready to present.

I knew the hiring managers that were going to be in the interview so I wanted to make it personal–trying to show that I would do my research on our customers to make a more strategic approach to our sales plan.

So I got some background info on the managers and included some of their likes and dislikes in my presentation. One of the managers was a huge dog lover and I snagged a picture of her dog from Facebook and included it in my slide.

Little did I know that her dog had passed two days before the interview. She saw that pic on my slide and immediately started crying hysterically. She then proceeded to leave the room and that is when one of the other managers let me in on her dogs passing.

Still got the job but was THE most horrifying work experience I have ever had.

Gene Caballero, Co-Founder of GreenPal



workplace horror storiesI Learned Friends and Family Don’t Mix with Business

When I look back at mistakes I made in early on in my entrepreneurial journey, I realize that my early hiring practices were terrible. Like everyone else, I thought I could get my entire family working with me and it would be the best company because we all think the same. That was a big mistake. Friends and family have no place in business and I learned that the hard way, so now I make sure that doesn’t happen. We always hire people that have no other ties to us other than the work itself. That way we both understand where the relationship starts and ends.

It’s important to be careful with your hiring, take a lot more time, look at a lot more candidates, check a lot more references, and don’t just make a hire out of desperation. A bad hire is more painful than no hire. A mediocre hire can be the worst, because someone just doing the minimum and taking up space on the org chart and payroll is preventing a good hire from being there for years.

Dan Roberge, President of Maintenance Care



business horror stories

The Click of a Button Cost Us Nearly $30,000

When my dating business was covered in the New York Times over seven years ago, we got site traffic from all over the world until crashed (mild nightmare). Once the site came back to life, we got orders all over the country. The Cheekd business model, at the time, was based on a recurring subscription model. It was the biggest day in the history of Cheekd.

Soon after, we realized that our web developer based in London had the button ticked OFF that captured our users credit card information and were unable to enroll them into our recurring subscription. With hundreds of new signups, we lost nearly $30,000 from this simple mistake. I joke now that our London based web developer is lucky that he didn’t live in America at the time. We immediately hired someone else and got that button fixed.

Lori Cheek, Founder/CEO of Cheekd



email marketing

I Decimated Our Marketing Budget

In the early days of our experimentation with digital marketing, we decided that the best use of our measly budget would be to start bidding on a few competitive keywords through Google Adwords. After setting up the account, we let it sit for a bit, and essentially completely forgot about it. When we logged into our account over a month later, we realized the mistake we’d made. Not only had our ads been getting clicked on for completely irrelevant keywords, they were also expensive keywords. Once we payed the sizeable bill, we decided to get the help of a professional!

Max Robinson, FishTankBank


why I love my businessWe Went Days Without Power in Our First Office

There was a power outage the first day we moved into our first office. I wasn’t worried until it had been hours with no power. I started to worry a little more after we went one whole day without power, and a little more after we went two days without power. By the third day without power, I thought it was a sign from above that we shouldn’t have started a business. Thankfully, the power came back on the fourth day, and my team got to work. We haven’t stopped since!

Vladimir Gendelman, Founder & CEO of Drinkware Company

Have you experienced any workplace horror stories of your own? Sound off in the comments!

Leave a Comment

Start typing and press Enter to search

What is HTTPS?influencer marketing