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It’s really hard to see people go through very difficult times because of bad financial decisions that they’ve made in their lives.

And, as you probably know, it happens to quite a few people.

So what’s the worst financial decision you’ve seen someone make?

Let’s check out some interesting stories from folks on AskReddit.

1. Irresponsible.

“People who make over $250k (sometimes WELL over), no withholding, not paying estimated taxes throughout the year, can’t afford the tax bill with the return EVERY YEAR, then b*tching because they can’t afford the installment payments on the taxes they owe from two years ago.

Motherfu*ker, sell your gaudy McMansion, take your teenage daughter’s credit card away, let your drunk driving son stay in jail and get a public defender, and tell your wife to stop spending all day at the tennis courts sipping mimosas.

Get your sh*t together and pay taxes throughout the year like the rest of us. You aren’t being persecuted by the IRS, you’re just an idiot.”

2. Sad.

“I work for a bank.

One of our branches had a customer who was basically homeless. Then, he wins the lottery! Over the next few months, the staff watched him come in to withdraw thousands of dollars every day to spend on extravagances.

Everyone tried to convince him to sit with a financial advisor to help him make the most of his money. Less than a year later, he’s in slightly better shape than when he started; he’s at least able to live in the car he bought.”

3. Yowza.

“I’ve had a client where I noticed this guy’s credit debt always remained hovering $13k to $15k.

I asked him why he only makes minimum payments on his credit card instead of paying it off, because I see he has roughly $11k sitting in a bank account. Interest per month on that credit card bill is roughly $250, and according to his repayment patterns it will take him roughly 19 years to pay it all off.

His answer to me is the bank charges him $7.99 per month for his bank account if his balance dips below $10k… So to save the $7.99 per month this guy is paying $250 in interest on his credit card.”

4. Do your research.

“What I’ve seen, countless times, is someone who started a business with ZERO research, no understanding of what running a business involves. (Here’s a hint: practically every business involves paperwork and deadlines.).

The business models come in waves… for awhile it was Barbecue shacks, then it was cupcakes, then house flippers, then food trucks. I think they see it being done on TV shows that make it look fun. It isn’t fun when they come to me with debt, tax levies and lawsuits.

IRS and state labor department and health department on their backs, and suppliers taking them to court for unpaid bills. Some of them cashed out their retirement account to buy a business; others put their house up as collateral for an SBA loan. it’s a nightmare.

If they had come to an accountant first, we might be able to help them (or even better, dissuade then). I usually see them after 18-24 months of screwups and by then it’s usually too late to rescue them.”

5. Uh oh.

“An older gentleman came in worrying about a ton of overdraft fees on his 18 year old sons account. The fees added up to a hefty amount and he was worried that the charges were fraudulent.

Upon looking at the account history, every recent purchase was to OnlyFans. The fees were happily waived and no detail was given as to what OnlyFans is, as the kids old man clearly didn’t know.

I think about that kid often. I wonder how he’s doing.”

6. Car problems.

“Claims Adjuster here, and I see it happen all too often – trading in vehicles with negative equity.

Why? Why can’t you be financially responsible and pay off your vehicle instead of rolling the leftover loan onto that new shiny machine you just can’t resist, and rinse/repeat a couple of years later. Your loan is just getting bigger and bigger.

I had one client (recent, otherwise I had more than that) – who totaled his vehicle. He blew pass a stop sign and collided with another vehicle. Guess what friend, out of that $70,000 you still owe to the bank because you’ve traded in 4,5 vehicles over the years – we are only covering you for what your current vehicle is worth today, around $25,000 or whatever it was – depreciation applies unless you have the proper endorsement in place. That means you will be paying the bank for the leftover loans of some vehicles, none of which you own.

Own one vehicle, one loan – if you ever totaled your vehicle, insurance will provide you enough to cover the loan. If it doesn’t quite cover it because of high interest, it sure as hell isn’t a $45k loan left.”

7. Bummer.

“I had my former boss decide it was a great idea to buy land in Texas, our company was based in PA, in the middle of nowhere because he talked to another business owner who told him it was going to take off.

Myself and my co-worker advised against it but things were slow and he didn’t listen. At first it was going to be a place of operations but then he decided we would just rent out rooms to the people who worked down there in the oil industry. Dumped loads of money, time, and blood, sweat, and tears into it for it to just go bust not even a year later.”

8. Play nice.

“Worked in a family law firm.

Way too common of an occurrence is a client ignoring the lawyers advice for a balanced separation agreement and instead ambushing their spouse with an agreement that says they are getting everything.

Now instead of a relatively amicable breakup and maybe some mediation to sort out some sticking points it’s tens of thousands if not hundreds of thousands of dollars in litigation costs.

If you are going through a divorce play nice. The only ones that win in a bad divorce are the lawyers.”

9. Hmmmm…

“I audit larger companies so I don’t work with individuals. However, my friend’s dad mentioned that he pays 3.5% annually in advisor fees to his financial advisor, and that’s not even including the fees that the mutual funds he’s invested in are charging him.

So annually, he’s paying out in the ballpark of 4.5% of his portfolio. That’s right, every freaking year. I tried to explain to him that these fees are potentially costing him millions more than a reasonably priced advisor who recommends low-cost mutual funds would charge him throughout a life time. He just kind of shrugged and told me that he felt comfortable with the guy.”

10. Time to mitigate the damage.

“A 94 year old woman withdrew a $540,000 annuity that she THOUGHT was a TAX FREE life insurance policy. She owed the IRS over $90,000 and the State of Michigan $14,000.

When I explained it was an annuity and not a life insurance policy she panicked. What was done was done and we just had to mitigate the damage.”

11. That’s not good.

“The parents of a young woman bought her a condo. They paid cash so she wouldn’t have a mortgage. She sold it so she’d have party money.

Not only did she no longer have a place to live, she owed taxes on the gain. But she’d already spent the proceeds so didn’t have money to pay the taxes.

Oh, and she didn’t have a job because it would interfere with her partying schedule.”

12. Family drama.

“Grandma pulls 50k to help grandson pay off college debt. He blows all the money, steals another 10k from her.

She won’t file police report because “they are family”, daughter steps in, grandma is furious with daughter for telling police what happened. Grandma takes daughter off as beneficiary, replaces her with grandson.”

13. “Still haunts me…”

“I’ve seen plenty that made me cringe, but the worst one wasn’t because there was a lot of money involved.

So I’m working at this bank branch years ago, I was tired of being stuck in the drive thru so I made a lateral move to be a floating teller among other things. But occasionally I’d have to fill in at the old branch, which sucked because the manager there hated me.

Anyway, during my time there I became acquainted with an older gentleman, he was a world War II vet and was always wearing his navy vet cap. I talked to him every time I saw him and he was always really nice, had a great sense of humor, and even in old age he was still mentally sharp.

So this one day I’m filling in at the branch covering for the new accounts person. This guy walks in and I immediately knew something was off. I greeted him and asked how I could help him, and what he said broke my heart. He told me that he wanted his daughter off of his account, that she had been taking advantage of him and his money was being wasted.

I did my due diligence and brought up some history and asked him about specific charges, I remember there were a bunch for a couple of salons, so clearly those weren’t his transactions. The last few times I had seen him, there was a younger woman with him that I hadn’t seen before, and he was pulling out cash and giving it to her.

It dawned on me that each time I had seen him, he was there with someone else that did all his stuff for him, and that this time he had come in alone, which never happened.

So while looking at his account I noticed that his daughter is an owner on the account, meaning he can’t just remove her, she has to consent to it. When I asked him if he thought she would agree to that, he said no and started crying.

Normally we weren’t supposed to keep pushing a situation like this, but I really wanted to help him. I told him I couldn’t get her off the account, but I could open him a new one where he would be the only one on it, and then we could transfer the money over.

I could tell he was relieved when I said that to him, so after a few minutes I took care of everything for him. I specifically remember that after I finished, I gave him my business card, and told him that if he had any issues he could call me. A few minutes later he left happy, and I briefed the manager on what had happened.

A day or two later I’m working at another location when I get a call on my cell from my boss, she asked me if I had helped an older gentleman with his account when I was at my old branch. It turns out that after I had helped him, his “daughter” had tried to use the account to pay for more of the sh*t she was wasting his money on, and the card was declined.

She had gone into the branch and raised hell, screaming at the employees there and demanding they bring her the person responsible. The business card that I had given the man didn’t have my direct number on it, the number went to my boss. She had screamed at my boss and demanded that I be fired for what I had done.

My boss as well as the branch manager that hated my guts had both defended me and neither of them would give in to her demands. But I found out later on the next time I saw my boss, she had forced the old man to either move all the money back to the old account or to make her an owner on the new one. When anyone asked her about the situation, she just claimed that he had dementia and didn’t know what he was doing.

I honestly hope she was telling the truth, but I never saw that man again, and had moved into another role and then to a different company not long after. I went to anyone that would listen about what happened, but no one could do anything because elder abuse is so difficult to prove.

The whole thing still haunts me, I saw an old man asking me for help and did the best I could for him. In the end he either made the decision to keep her around or was forced to, and I worry I just made things worse for him.”

14. Wow.

“My brother had a long standing client of around 10 years get married after only knowing a woman for 12 months. He was almost 55, she was in her early 30s.

55 y.o. man wanted to add her as a signatory on his retirement account. Basically giving her 100% power over the account. A quick soft credit check showed she was not good with money. My brother offered up many different options as to how to give her access to the money but with limitations. He even straight up refused to do it, saying that he needed to think about it for a few days.

The guy came back in the next morning saying he would file a complaint against him if he didn’t set it up. My brother said that he would need to get the documents notarized, and sign a waiver that this is against the institutions advice.

The guy comes back in later that day and finalizes the deal.

You can guess what happened within about 6 months.

The account had around 600k in it to begin with, and she had managed to run off with about 65k before the account was frozen by my brother for review of withdrawls.

The man was p*ssed and tried to lawyer up twice. Neither time did it even go to court.

His advice is that if you are married and have investment accounts, just keep them separate unless you REALLY have a reason to give them access. You can totally notify the agency about your marriage, and sometimes in certain situations the spouse can get limited info confirmed for medical bills and such.”

How about you?

What’s the worst financial decision you’ve ever seen someone make?

Tell us your stories in the comments! Please and thank you!


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