Last month, we talked about small things that almost took down a company or a person, and here are nine of my favorite stories you shared.
1. The $5,000 thank-you note
I had a friend working as admin staff in a law firm where they lost out on literally millions of dollars in legal fees and a partner was disbarred over an unjustified $5,000 bill to the client.
The firm was representing a client on a high-eight-figure settlement and the legal fees were in the low seven figures, so it was a wildly profitable project for the firm, but greed knows no bounds. After the case wrapped up and the “final bill” went out to the client, she received an additional bill for $5,000 for “post settlement services.” It was really a drop in the bucket for what she had paid so far, but she couldn’t get a clear answer on what the those extra “services” were.
She was so annoyed she complained to the law society over it and the firm finally gave an explanation: all the lawyers on the file, including the partner in charge of her case, billed her 15 minutes of their regular hourly rate to read her thank-you note that she sent after getting the final bill. The law society’s auditor then demanded a detailed list of all their billing rationale and found that at least a quarter of their billings to the client were for dubious at best and totally fraudulent at worst reasons. The firm had to refund that all back, plus pay a huge fine, and the partner was disbarred when it came out that he had been the one directing the firm’s lawyers to bill this way. It also destroyed the credibility of the firm and the other partners went after the disbarred one to recoup the losses.
All over an extra $5,000 bill for reading a thank-you note.
2. The ice supply
A good friend got a job as the business manager for a graduate school department at a major college several years ago. Among her tasks was budgeting and taking care of bills. Shortly after she arrived she noticed that one sub-department had a budget line for $200 a month marked “Ice.” She assumed “Ice” was an acronym (“ICE”) or something college-y and didn’t look into it, as she had bigger fish to fry.
A year later the budget request for “Ice” came in for $240 a month. While a small dollar amount increase, she was asked to look into any increase requests over a certain % increase, so she followed up with the department chair.
Turned out that “Ice” budget was for actual ice. An old professor each week had ice delivered to his office by a local ice manufacturer. So that he could have cocktail parties in his office. With old-school ice cubes. The cost? $50 a week.
When confronted about this, the professor insisted he needed the ice and had been getting it delivered weekly since he got tenure in the 1980s. That’s $2,400 a year, or $50+ grand probably, for something he could get for nothing at the cafeteria or make himself in the office fridge.
Plus, his “cocktail parties” often featured certain attractive under-age undergrads.
The professor decided to retire before the campus ethics board got involved.
3. The eighth grade debate
When I was in the eighth grade, the school’s principal decided he would teach a weekly class of “current events” where the students were asked to bring in newspaper articles and we would discuss them. Since the principal didn’t have a classroom of his own, he used the science teacher’s classroom, which had an office for the science teacher attached.
One day, one of the kids from the class brought in an article about how someone had found “evidence of satanic rituals” in a local park. One of the boys said “Satan, cool!” or something like that, because, well, he was a 13-year-old boy. I’m pretty sure he did it in the voice of Beavis and Butthead. The principal sent him out of the room as punishment.
Our class ERUPTED in accusations of religious intolerance from the principal. We argued and argued, giving him scenario after scenario to determine where his line of religious tolerance was. “Would you admit to this school someone who was of a religion that worshipped the devil?” we asked. “Isn’t it illegal not to?” (We were a private school.) Our interrogations led him to state that he would not admit certain students due to their religion. He kept trying to send us out to recess, but we refused to leave! My class passionately defended the rights of Americans to practice whatever religion they wanted and accused him of practicing discrimination.
As it happens, the science teacher was listening to the entire conversation from his office. Later, I overheard him discussing the incident with another teacher and saying how problematic the conversation was and how he was shocked at the principal’s statements.
About a month later, we received a letter saying that the principal was resigning. I don’t remember exactly what it said, but I do remember my dad saying, “Wow, it sounds like he got canned.”
I’m not 100% sure that the two incidents were related, but also, if they weren’t, it’s quite a coincidence.
4. The misspellings
During my time as a government auditor, the biggest fraud I ever uncovered was a result of inconsistent spelling of a key person’s name in official documents. Think Anderson, Andersen, Andersin. It was annoying me, so I looked for the correct spelling in other documents, which ended up not existing. Which lead to a lot of other things.
5. The budget documents
A long-time CFO at my small nonprofit was brought down by a grumpy board member who couldn’t understand why the CFO could not simply provide the reports she wanted to see directly from our financial system. The CFO had been giving the board heavily edited and formatted budget documents for years and, because she and the rest of the leadership team were so well-respected in our small community, no one ever questioned it. Turns out, we were over budget by about $1 million (on a $7 million budget that had basically doubled over the course of three years) and no one realized it. The grumpy board member kept asking questions and the CFO couldn’t cover her tracks any longer, which led to the firing of the CFO, a major restructure, and two CEO transitions over the next 18 months.
We’re okay again but for a while there, our 100+ year old organization was almost brought down by a lack of checks and balances. The grumpy board member chose to step down after her first term and while no one exactly misses her, we owe her a great deal for not putting up with any prevarication during her time with us.
6. The fancy car
A coworker of mine at a former job worked for our state’s department of revenue. He told me about a time when a colleague of his noticed a Very Fancy sports car in the middle of Absolutely Bloody Nowhere, which was not one of those quiet little town that secretly has a Google data center or something. Colleague, a fellow tax agent, found this odd and when he got back to the office cross-checked the registrations of Very Fancy Sports Cars with the people living in Absolutely Bloody Nowhere. Sure enough, they found him, and after a very little research figured out that he’d been defrauding the company he worked for to the scale of millions.
7. The rejected edits
I had a manger that believed he was best writer in the world. Our company had an editing team that wildly disagreed with that and he greatly resented their “overreach” when they edited his reports to clients. He complained and was eventually told he could have staff familiar with his projects review his reports. So he had me do it, bragging the entire time that I wasn’t going to find anything to change.
I looked at it and pretty quickly found some problems, namely he had taken a report for an entirely different project and done a find and replace for the client’s name. But he hadn’t caught when the clients name was pluralized, which was almost every page. When I told him this he was pissed, argued that he was just being efficient, that no one was going to read it that closely anyway, and I was a terrible writer so what did I know. He refused to fix that problem or make any other edits I suggested, turned it into the client early even because he firmly believed that would make us look good.
The client was the U.S. Air Force.
I wasn’t privy to everything that happened next. But in rapid succession he was let go, we came close to losing all our government contracts, which would have shut down out office, and me and my new boss spent the next six months redoing everything he had previously delivered because we figured out he had been making up data. Data we had on hand! He was so lazy he wasn’t bothering to read my field reports and carefully made maps in favor of writing stuff that he thought sounded right. It was stressful and a mess and cost the company so much money.
If he’d accepted my edits or better yet kept letting the editing team continue to fix his reports, none of that would have happened.
8. The artwork
At a small marketing agency, our biggest client wanted to use a specific piece of artwork in a national ad campaign. Our principals reached out to the artist, who quoted around $50k in licensing fees. The client balked, but still wanted to use that piece of artwork. The principals decided to commission a much smaller artist for a similar piece for $2500, with our agency retaining all the rights.
The client kept nitpicking and asking for revision after revision, until the commissioned piece was extremely similar to that artwork they really wanted. The new artist expressed multiple concerns about copying, but the principals kept pushing to get to where the client wanted the artwork to be. The ad campaign was published, and the client put out plenty of press releases and social content showcasing the art.
Allllllllll of this communication was done over email, which made the original artists’ lawyers’ jobs extremely easy when they sued our agency and the client for a couple million in copyright infringement a month later. The case eventually settled in the original artist’s favor, and both our agency and our client had to pay out the original licensing cost, plus legal fees, and take down all content featuring the copied artwork. I was one of the few agency employees unlucky enough to survive the layoffs afterward, and the cost-saving measures the owners took in the years after got pretty interesting.
9. The treasurer
15+ years ago, I joined the (volunteer, unpaid) board for a youth performing arts nonprofit. At my first board meeting, I found out that our treasurer was under investigation for stealing up hundreds of thousands of dollars from our organization, his employer, and the booster group at the school where he taught jazz band. (Y’all, this isn’t even the thing that almost brought the org down!) The result was that we were without a treasurer and couldn’t find anyone to do the job on a volunteer basis.
Instead of paying to hire an hourly accountant, the board decided the president (who was a freelance writer for financial publications so of course he’s qualified) would serve as both the president and the treasurer. Safeguards were put in place so that any purchases or withdraws over $500 would require two signatures. This went on for six years without much turmoil. Books were balanced every year, and the president/treasurer was so fiscally conservative we had to fight tooth and nail to buy equipment that should’ve been replaced several years prior, so things seemed fine money-wise.
In year six, we had an actual CPA elected to the board as an at-large member, and in her second year she ran for treasurer. The president-treasurer seemed genuinely elated he no longer had to do both roles after seven years, but that whole next year, he threw up blocker after blocker for her. Things like QuickBooks “couldn’t transfer access” to her or they could never agree on a time to meet at the bank to get her added to our bank accounts. He also insisted that he’d file our taxes so she wouldn’t have to deal with that hassle. For some reason, these things weren’t red flags for the rest of us, partly because he was still around and partly because he was a “nice” guy.
At this point, I’d transitioned out of a board role and into a paid staff role. When the new treasurer started creating paychecks and mileage reimbursements, I told her that my mileage checks were wrong and much higher than normal. The old treasurer been using the IRS standard rate for charities ($0.14 in 2026) instead of the IRS rate for business ($0.72 in 2026) which is what the new treasurer was using. He doubled down on the charity rate being the correct one even though the staff were all paid contractors. The new person was, of course, correct, and this mileage fiasco made her look into more and more of the documents from previous years.
And that’s when we found out he hadn’t filed our taxes in the past seven years, which included the form for our 501(c)3 status. The same status that allowed us to be tax exempt on every purchase we’d made for the past seven years.
The president-treasurer was immediately removed from the board, and the new treasurer and VP started down the nearly two-year road of retaining legal counsel, rectifying our taxes, re-applying for our tax-exempt status, calculating the back taxes we’d owed not just ot the IRS but all the sales tax for seven years, and doing damage control with the member groups we served. As a staff member, I know there were discussions and details I wasn’t privy to, but I do know legal action against him was talked about and then dismissed as an idea.
I’m happy to say that I’ve been involved with the org for almost 20 years now, and we are thriving. We’ve more than doubled in size in that time and finally have a paid executive director, about 30 paid staff members (so the board can actually be a guiding, “volunteer” board), and most importantly — a paid accountant.
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