What’s The Silliest Business Mistake You’ve Made? — Experts Weigh In

Have you ever accidentally hit reply all on an email everyone wasn’t supposed to see about your post-work agenda? Did you once call your boss ‘mom?’ We all cringe when we make a silly mistake in the workplace, but the good news is everybody does it at least once. 19 experts revealed to us the goofiest slipup they made in the office and how they were able to laugh it off.

1. “This one was painful at the time, but I can laugh about it in retrospect. I run a small gaming company and I was ramping up for our product launch. I finally had found our first review channel to record a video review of our game. I was ecstatic! I grabbed the prototype, rushed to the post office and eagerly awaited a response. About a week later I see a post fly up on a board game community with a picture of an empty envelope. It said, ‘Any idea who Hill Gaming Company is? They sent us a game and didn’t seal the envelope.’ I looked at a picture of a mailing bubbler with the adhesive cover over the sticky part still on untouched. I hadn’t closed the envelope with my game inside. My heart sank. Not only did I make a bad first impression, but now I was on public blast! Luckily, the channel promptly took down the post after I messaged to them. Afterwards, we got them another copy of the game (properly sealed!) they left a glowing review.” — Casey Hill, Founder, Hill Gaming Company

2. “Recently, we redesigned our welcome email that goes out to all of our new customers. In the design we hardcoded a placeholder name of the famous WWF wrestler Randy Savage who was popular in the 1980s. A couple of us in the office get nostalgic from time to time about wrestling in the ‘80s and so one of the designers hardcoded that in as a joke. We shipped it live and it literally went out to all our users for two weeks until we discovered it. Silly mistake and all of our new customers were greeted as a famous professional wrestler.” — Zach Hendrix, Co-Founder, GreenPal

3. “We just had moved to South Jersey and purchased a cleaning franchise. I wasn’t familiar with the area, but our advertising took off and within our first month had over 100 customers. A customer called complaining the cleaners were an hour late to her home. I logged into our check-in system and saw the cleaners were already in her home. I called her back and said looks like they’re there. She screamed at me that they weren’t. I called the cleaners on their cell and asked where they were. They said they were at the house and almost done. Confused, I decided to drive over to the customer’s home and upon pulling in front saw my company car parked on the street. I went to the customer’s door, knocked and said that I was sorry, but I saw their car. She said, ‘Well, they’re not here.’ I called the cleaners and asked if they could walk to their car from where they were. The customer and I saw the cleaners walk out of the house across the street. We both laughed — they had cleaned the wrong home! Funny thing though, these teenage girls ended up doing me a favor because the home they cleaned was so happy they signed on as customers also.” — Mike Kawula, Co-Founder, Dinner Table MBA

4. “The silliest thing I have ever done was sending an email to a supplement brand trying to convince them to work with us, but calling them by the name of their competitors the entire time. They were so mad at us because they thought we have copied and pasted an email that according to their version we had sent first to the other brand, which we never did, and it was frustrating to try to explain that to them after they have received that email. Check twice before sending emails!” — David de Ponte Lira, Founder, FullMusulo.com

5. “We accidently cleaned the wrong apartment. Imagine coming home after work to a perfectly clean house! I can only imagine what they were thinking or why someone would break in their apartment just to clean it. How did this happen? One of our customers had moved to another apartment. They were recurring and forgot to inform us they were moving. Our cleaning team arrive on the scheduled day and the apartment staff provided the key — which they shouldn’t have, but gave out of habit. Our cleaning crew did their job and cleaned the apartment. A couple of days later we discovered the mistake. I had to call the apartment office, so they could inform the new tenants what had happened. The tenants were not freaked out or mad. They liked the cleaning so much they became our customer!” — Greg Shepard, Owner, Dallas Maids

6. “I’ve launched and ran several websites. My first site launched when I was about 16 and I had got some Indian developers to build it. I launched the site without testing it thoroughly and received an email about three weeks in from a potential customer saying that he had been trying to sign up for a few days, but the site would only accept Indian postal codes (zip codes). Being 16 I had spent most of my available marketing budget by this time and it had a big impact on the success of the site. We live and learn!” — Daniel Hall, CEO, Hubbite

7. “The silliest mistake I’ve ever made was sending one of our smallest customers an invoice for one of our biggest ones. Obviously, they were not happy about getting a bill that was nearly 10X normal. However, after talking to them to calm things down, it opened a conversation about whether we could do more for them. In the end, we couldn’t and I’m lucky they weren’t angrier, but I hope it did at least help educate them on our capabilities. Lesson learned — I know to triple check invoices before sending.” — Ian Wright, Founder, British Business Energy

8. “Ever since becoming an entrepreneur my wardrobe has gone from suit and tie to t-shirt and slippers. Working from home has improved my lifestyle, but it has created some embarrassing situations. There has been more than one occasion when I’ve answered a Skype chat from a client only to remember that I was sitting at my desk in my robe. I guess the key to working from home is to be comfortable, but doesn’t get TOO comfortable.” — Evan Roberts, Founder, Dependable Homebuyers

9. “The silliest mistake I ever made was when I was ending a conversation with a client. I meant to say, ‘Have a good game!’ (he was on his way to a pick-up soccer game), but I combined it with ‘Have a good day!’ so it came out like ‘Have a good gaaaaaime.’ We both started laughing hysterically, and now it’s an inside joke between us. Whenever we email or talk we end our conversations with have a good gaaaaaime. I actually think this has made us bond more and we have a more personal relationship because of it, so it’s actually helped our business.” — Sarah Moe, Co-Founder, Flauk

10. “I have found major success in connecting with people on LinkedIn. Once,  I was sending messages to the masses (first mistake — always personalize messages) and I forgot to change the name on my template. I sent out about 10 messages and closed my blurry eyes to finally get some rest. The next morning, I saw my mistakes and my stomach jumped into my throat. I successfully sent 10 messages to big time people in my area addressing them all (including men) as Susan. I didn’t even say anything afterwards, but now I am able to laugh about it. Moral of the story: Don’t send invites on LinkedIn at 3 AM and always personalize invites.” — Secret Bridgewater, Chief Amazement Officer, The Social Secret

11. “The silliest mistake that I made was in my first business, a sportswear brand. I was in college and hadn’t told anyone that I was starting the venture so never ran ideas past people and we all know how things can go wrong if you’re stuck in your own head. I wanted to order some stickers and didn’t have a ruler. I Googled a ruler, and long story short, three weeks later ended up with 500 stickers triple the size I needed them! Safe to say that was a total muck up on my point. Always run things past other people!” — Vivien Conway, Co-Founder, Ace The Gram

12. “A couple months ago, we were in the process of launching an equity crowdfunding campaign through a platform called SeedInvest, who assists in filing the correct documents and working with major regulators and agencies. As part of SeedInvest’s due diligence on KPOP Foods, they performed a quick check to make sure we didn’t own any taxes to the government. I remember them asking me if I was aware of any outstanding tax payments and I told them no as we had filed our tax return and had been making all the tax payments, or at least that’s what we thought. Our point of contact at SeedInvest called us a couple days later and said that we owed a tax payment to Delaware for incorporating there and operating in California. She sent over a link and said that this was typical as a lot of new companies simply miss this. I clicked on the link, went through the page, and saw that we owed $750,000! My face literally went white as we barely had $10,000 in our account. Mike, who was sitting across from me, immediately asked what was wrong and with things moving so fast, I honestly thought the company was done. We eventually discovered that the information input to calculate our taxes owed was wrong and after making the adjustments, the final amount turned out to be closer to $600.” — Theo Lee, CEO and Co-Founder, KPOP Foods

13. “Once, I emailed myself about an employee who was about to be let go along with my talking points about their dismissal. I accidentally sent it to the employee instead of myself. It was not nice, but we both agreed on the points brought up in it. I still can’t sleep over that mistake.” — Daniel Nyiri, Founder & CEO, 4U-Fitness

14. “The silliest mistake I ever made was when I was starting out my company. A large part of SEO and content marketing is doing outreach. There is both mid-range outreach, and highly targeted outreach. At the start of the company, we were doing mass outreach like most companies — quantity over quality. Unfortunately, it turned out that one of the people we emailed ended up being the founding member of the CAN/SPAM Act! Understandably, it was less than ideal, and she sent a spam report email (CCing us in it) to every company that was contained within the email header HTML. The day I got this email, I thought everything was going to fail and didn’t know what to do. Luckily, as our email wasn’t spammy (there is a thin line between spam and outreach) we were able to do away with the solution without any problems — just a simple apology. Since then, we’ve upgraded our outreach solution on multiple levels, so we can avoid issues like these.” — Peter Selmeczy, CEO & Founder, SEOTech

15. “At PPC Protect we work in an open plan office meaning instead of hiding in an office all day, I work alongside my staff. Not so long ago I was listening to music on my headphones and had my Spotify playlist on shuffle. Around that time, I was just getting up for my morning coffee and completely forgot I didn’t have my wireless headphones on. As I walked to the coffee machine the cable came flying out of my computer and my music started blasting out on my speakers. Since the playlist was on shuffle I had no control over the music and it just happened to change to Justin Bieber’s ‘Baby’ at the exact moment my headphones came out. The whole office turned around (as most of them recognized the song) and started to sing along. I had to run over and turn it off as quickly as possible while telling everyone that’s not on my playlist I swear! As you can imagine, I was rather embarrassed as everyone thinks I enjoy the Biebs. To top it off, the following Christmas one of my staff actually got me a huge Justin Bieber poster which I keep hidden in the office.” — Alex Winston, Managing Director, PPC Protect

16. “We have made several silly mistakes with our clients in the past and they all seem to stem from text messaging! A few months ago, I was in the middle of multi-tasking. I was on the phone with my husband and was planning life and was also texting a potential client about the details of his romantic rendezvous. I texted my client ‘I LOVE YOU, MY KING.’ I hadn’t realized until after I had disconnected the call from my husband and about 45 minutes had passed and I was wondering why the client hadn’t responded back to me. When I looked at my text messages, I was so embarrassed, I called my business partner and told her and asked how I should approach the client. I didn’t want to send the wrong message and come across as being unprofessional or crossing boundaries. She told me to call him and explain. So, I called him. He literally answered the phone and said, ‘Hey, I’m going to assume you texted me thinking I was your King! I got to admit initially it left me puzzled, because our conversation allowed for it to be sent now. No sweat, glad you called to explain. Now, let’s get back to planning MY Queen’s romantic birthday surprise!’ Whew, glad he understood and was able to laugh it off!” — Ta’Veca Collins, Co-Owner, Romance on the Go

17. “The silliest mistake I made as an entrepreneur was arriving at a lunch meeting early. This may not sound too bad, but I arrived 24 hours too early. I only realized I was a day early when I called my client and asked them was everything okay. You could hear the confusion in their voice as they answered, Yes. Then they said, I am still good for our meeting tomorrow. I busted out laughing and had to tell them that I was already at the restaurant waiting for them, a day early. They found it amusing and felt good that I was anxious to meet with them. So, my little mishap worked for me and my company’s benefit.” — Vid Lamonte’ Buggs Jr., Author/Athlete/Philanthropist, vidbuggs.com

18. “Aside from running my own business, I help others marketing their businesses. One of those people owns a company Dekomats, which makes printed custom golf cart mats. I sent out an email blast to 7,000 people at the Villages in Florida about the golf cart mats, but put a link by mistake to my business that offers a medical device for women who suffer from pelvic pain! Let’s just say we got a lot of phone calls and emails from surprised customers. It blew over in about a week. It was so embarrassing then, but something I can laugh about now.” — Tara Langdale-Schmidt, Co-Founder, VuVatech

19. “A few years ago, I decided that I needed to have a MacBook. I was convinced that I would be more productive creatively and that it would help sync all our music and photos, thus making my personal and professional life seamless. Unfortunately, I could not make the computer work as I am a PC girl. It was simply foreign to me, so my husband helped me get the basics set up. Fast forward to Monday and my first corporate retreat for the afternoon.  We started with a power session meeting, sharing ideas and successes and failures to be followed by a fun dinner and night out in the town in Nashville.I set up my computer for a presentation and in the middle, I received an iMessage from my husband that was intended for my eyes only — it was a little dirty. It projected onto the screen for all to see. After an initial embarrassment, my team knows we have a strong marriage — and I was able to laugh it off — that 15 years in, we are still attracted to each other.” — Libba Durrett, Founder, Sparklers Online

Every entrepreneur makes silly mistakes, but the one you don’t want to make is not incorporating your small business. Let us help legitimize your company for you! Give us a call at 1-877-692-6772, or visit us at mycorporation.com.