Twitter might make buying a “small sweaty” business look easy, but let’s be real – running one is an entirely different ball game. While buying a business might give you the illusion of being a successful entrepreneur, the journey that follows is often filled with unexpected surprises, challenges, and moments that can only be described as “kicked in the nuts” experiences. Here are 13 hilarious and oh-so-relatable times when the realities of running a small business made life interesting, to say the least. So, grab your popcorn and let’s dive into the comical chaos of the SMB world:
1. The Suspiciously Frozen Funds Saga
We almost ran out of money just five days in because Quickbooks decided to freeze a whopping $100,000 for almost twenty days. And guess what? Their explanation was “suspicious activities.” Sure, Quickbooks, because freezing funds with no context is definitely a logical response. Thanks for the mini heart attack.
2. When Shipping Times Went to the Dark Side
Remember that time when the port backlog hit like a freight train? Well, it hit us too. Our product shipment times transformed from a cozy two weeks to an agonizing two months for our most popular product. Port backlog, you’re like the unwanted guest who overstays their welcome at every party.
3. The Great Money Tango
Growing sales rapidly is exciting, but it can also lead to hilarious financial acrobatics. We found ourselves juggling nearly $700,000 in sold but uninstalled work while having a mere $19,000 in our checking account. Let’s just say, untangling that mess took some serious financial gymnastics.
4. The Front Desk Revolving Door
Front desk personnel changes are supposed to be occasional, not a monthly sitcom. In just five months, we managed to go through five front desk folks, each with their own set of wild issues – from alcohol problems to disappearing acts. So, we redesigned the role, went global, and saved the office fridge-checking for ourselves.
5. The Not-So-Loyal Long-Time Employee
Imagine discovering that a trusted long-time employee was stealing from the company. They took customers’ payments, only to pass the work to competitors. The real kicker? We found out when a customer called us to inquire about the shoddy service. Well, thank you for the unexpected twist in the plot.
6. When the US Marshal Calls
Just your typical day when you get a call from the US Marshal, asking you to coordinate the arrest of one of your team members who happens to be a fugitive. Oh, and did I mention this happened while the said team member was at a customer’s house? Who knew a fugitive chase could be part of the job description?
7. The Labor Attorney Extortion Episode
Getting a nasty letter from a labor attorney is just another day in SMB life, right? They tried to shake us down for a whopping $150,000 on behalf of a former employee I had the pleasure of firing. The audacity was strong with this one.
8. The Drunk Ride Home Adventure
Picture this: driving an employee home at 10 AM because she’s too drunk to drive herself. And just when you think things can’t get any crazier, you catch her chugging a mini-vodka bottle while you’re innocently putting change in the meter. Cheers to alcoholism and unexpected roadside dramas.
9. The Invisible Broken Opt-In Form
Who needs a functional opt-in form on the website anyway? Certainly not our head of marketing, who managed to blissfully ignore a broken form for a whole ten days while we hemorrhaged $40,000 in monthly PPC. Pro tip: when it comes to PPC, working opt-in forms are pretty darn important.
10. The Mysterious “Customers”
Ah, the infamous “customers.” Let’s just say this category is a catch-all for all the bizarre, demanding, and downright perplexing characters we’ve encountered along the way. If you’ve been in the SMB trenches, you know exactly what I mean.
11. The Partner’s Promise Predicament
Discovering that a minority partner promised to give away 10% of our profits to a non-profit while negotiating with a disabled veteran at the helm – well, that’s just another day in the wild world of SMB. Who needs reality TV when you’ve got partners with questionable sanity?
12. The CEO Turned Roulette Gambler
When an investor steps in as interim CEO after firing the previous one, you’d expect them to make responsible decisions, right? Nope. Try witnessing the same CEO-turned-roulette-gambler bet a staggering $50,000 on a single spin at a trade show in Vegas. Talk about having your priorities in line.
13. The $25K Amex Loan Leap
Leaving a cushy $125,000 base salary job with guaranteed $200,000 earnings, car allowances, and a generous expense account to take a $25,000 Amex loan to bootstrap a business four months before a wedding? Yep, that happened. My wife loved that conversation, but hey, it all worked out splendidly.
And there you have it – 13 hilarious and utterly relatable tales from the SMB trenches. While running a small business might have its fair share of nut-kicking moments, it’s also an incredible learning experience that can’t be traded for anything else. After all, who needs smooth sailing when you can have an adventure-packed journey that shapes you into a battle-hardened entrepreneur? Remember, behind every laughable obstacle lies a valuable lesson that shapes the quirky path of entrepreneurship. So, buckle up, fellow SMB warriors, and let the chaos continue!