The Joys of Small Business Ownership

Small Business Ownership

Hi everyone! As you are all aware, my brothers and I went in together to buy an industrial service related business last August. And prior to the purchase of that small business, we already operated a financial service related business. With two businesses with a combined value in excess of a couple million dollars and dozens of employees, you can bet we have had a few occasions where we pull our hair out in clumps.

You’ve heard of my joys of home ownership, so today I thought I’d share some of the joys of small business ownership…And if you are a small business owner and have experienced some of your own “joys”, please share in the comments below!

Joys of Small Business Ownership: The Craziest Things We’ve Experienced

  1. An employee drinking on the job. Crazy and shocking for sure, and you can bet he was fired immediately…
  2. An employee failing a drug test so bad that the lab testing company recommended serious help for the employee. The test results were worse than the lab tech had ever seen before…
  3. A brake pad falling off one of our work trucks. Unsafe…just a little! Fortunately it happened in our parking lot and nobody was hurt.
  4. One of our employees dating a new hire. They moved in after a month to a much more expensive apartment. A month or so later she dumped him and left town, thus leaving him as the only signer on the apartment he could no longer afford. He’s a good employee we don’t want to lose so we offered to help him out with temporary loans until he can get out of the lease to a cheaper place. What a deal…we lose our new hire and one of our good employees is now strapped for cash.
  5. The background check on a new hire turned up that he was a sexual predator. Obviously grounds to be fired immediately. It was a silly issue from 20 years ago when he was 16 and he is working with an attorney to get it permanently expunged from his record. We gave him some time to get it expunged; however, it wasn’t resolved quickly enough so we were not able to keep him employed.
  6. One of our marketers getting in a bad car crash and having to be out of work for a prolonged period of time. We kept her position open for her to return to for quite a while, but unfortunately she ended up quitting. Talk about us being behind the 8-ball on finding her replacement!
  7. An employee developing serious back issues requiring surgery and being away from work for four months during our most busy time period. Thankfully he is back now and recovering well!
  8. An employee developing cancer. She went on leave as she fought it off and has successfully returned to work. She’s been a good long-term employee and we couldn’t be happier for her.
  9. An armed robbery at one our financial service business locations. Crazily enough, an employee tried fighting him off. A shot was fired through the struggle and it went through the roof. Nobody was injured, and the robber took off running. Unfortunately we didn’t catch the guy, even with our video surveillance, and we lost out on a few thousand dollars of cash stolen plus the repairs, etc.
  10. We’ve also had two separate occasions where employees tried to steal from us from our financial service business. They opened up fraudulent accounts / loans. Crazy situations with each having unique background stories, but suffice to say we have good measures in place to catch such activities quickly.
  11. Lastly, and most recently, we had one of our favorite and most experienced employees get in a hit and run accident with our work truck after hours. When I told my wife about this she jokingly said, “Well he wasn’t the one who ran was he…” Uh, yeah hun, he was. Horrible and disappointing deal…including having to fire one of our best employees and find a replacement for our now totaled truck.

I initially started this post off as the top 5 crazy things we’ve experienced as small business owners, but the list quickly grew. Including the hit and run that happened just a month ago. I thought about stack ranking these too, but that was too difficult. They are all so crazy!

While small business owners certainly have to put up with a fair amount of frustration, there is also a fair amount of joy and pride.

The Trade-Off

Fortunately I have my three brothers as co-owners to share these experiences with and I have confidence we can figure anything out together. I’m willing to put up with these “joys of small business ownership” for two reasons:

  1. The expectation to make out-sized returns. By that I mean for the business value to grow well in excess of the 7-8% returns the S&P 500 generates over the long term. My personal goal and expectation is double that, around 15% annually. While the industrial service business has started off a bit slower than expected, we’ve met or exceeded budget in each of the last six months with continued momentum. And the financial service business has been a strong, stable performer.
  2. The joy and pride of working with my brothers, building a business, and providing a stable place of employment for many others is a very rewarding experience.

Opportunities Multiply as They Are Seized

Plus, as I’ve written before, opportunities multiple as they are seized. My brothers and I took a risk in buying the industrial service business. It was clearly more of a turnaround than we initially expected, but we have confidence in turning it around successfully at this point. We’ve made lots of progress and have a number of good things going for us.

While the setbacks I listed above seem daunting at the time, in most all situations they’ve worked out for the best. For instance, we’ve had good luck finding an even better replacement employee than the employees who quit or were fired.

Also, we’ve started to build a reputation for ourselves. By successfully changing the culture of our business, improving the operations, developing close relationships with other related businesses, and actively pursuing multiple new lines of business and revenue growth, new opportunities have now been presented to us.

Specifically, one major new opportunity that we are currently working through that could drastically change our business for the better and enhance the potential financial gains of the business. Not to leave too much of a cliff hanger, but I’ll save this update for another time. Check back next Monday for the update.

Thanks for taking a look!

The Green Swan










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  1. Wow. Sounds like a lot of work (and a lot of stories). Glad to see you’re still enjoying the experience and creating your own opportunities!

    1. Some pretty crazy stories for sure… Of which I could have never anticipated or dreamed of. It’s been a good journey so far though!

  2. Lots of stories in small businesses. I know when I worked for the bookstore company, my co-manager came in early to find a bunch of people (only one of whom was an employee) passed out on the floor after a raging party. Frankly, I was glad it was him and not me who found it.

    We had to fire people for theft at least once a year. There were numerous dating shenanigans among are mostly 20-something employees. And that doesn’t even start with the crazy customer stories that come up in retail, and the insane things people brought to the store in the boxes of books they wanted to sell…

    1. Haha that must have been some party! I’m just in shock by some of this crazy stuff that comes up. Thanks for sharing your stories!

  3. Thanks for sharing your crazy stories! Stuff like this unfortunately happen. I have a fair amount of my own stories from our company. It’s crazy the things that happen and the types of things you have to fix on a daily basis. I don’t know how much on the litigation side of things you’ve gotten into. But that can get hairy pretty quickly too.

    1. Funny you mention that as something may be looming, but too early to tell how it’ll go. I’ll save that for another update. Otherwise we’ve been involved in various court proceedings but no major litigation… Knock on wood!

  4. These are great stories. Keep ’em coming.

    There are happy endings, too: I started Monday with a tenant problem that I didn’t know how to fix. The first two shops I called couldn’t get out to the property in less than a week. I was bummed until the tenant called back, said he’d found the burned out part, was getting a new one at lunch, and would install it after work. I told him he had just made my morning!

  5. Great to see these worked out well in the long wrong run – hard to believe some of these stories. Talk about perspective awakening lol! We tend to think that people have the same values as us, sometimes this isn’t the case eh?

    1. Definitely. Life always had a way of working out.

      And yes it is eye opening to how different life is for everyone! It’s grounding.

  6. Some of these are really crazy stories. Thieves, drug addicts, sexual predators, a love affair… And this all happens at a company with a few dozen employees. Next business idea might be to write a movie script 🙂

  7. Those sound like the restaurant shenanigans that went on at nearly every restaurant I worked at, lol. We just didn’t have company vehicles to add into the mix of things people could screw up. 🙂 That’s got to be great knowing you can provide employment and a good place to work for a lot of people. It seems like the upsides far outweigh the downsides in your situations.

    I second the idea that a movie script should come out of some of these stories.

    1. Sounds like you had some interesting employment in the restaurant biz! Workplace shenanigans are always a lot more fun as employees than for the owners. 🙂

      Yes that may be the case… Perhaps it’s time I should enter the movie biz 🙂 It’s quite a tale that a simple post can’t do full justice!

  8. Geez, you got enough material for a reality TV show! But you are right, of course; returns of private business are higher for that exact reason. I invest in publicly traded companies and for the peace of mind and convenience of not having to deal with any of this will cost me. Lower returns than a small business. Much lower returns if you believe Jack Bogle with his 4% return prediction.
    Great post, as usual!!!

    1. Thanks ERN! Besides the above market returns it is a nice side project for me and my brothers and I enjoy working on it with them. Entrepreneurship definitely would need to be an itch you want to scratch to make the hassles worth while.

  9. I’ve always been a fan on doing your own thing. There’s no punch clock, but the hours, especially if you have family, are way worse than a full time position. Though with a full time position you could just be called into the office and sent home packing for no reasons at all. Seems like you guys had it covered for the most part.

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