Financial Experts Break Down The Worst Financial Decisions They've Ever Seen A Client Make
Image by Arek Socha from Pixabay

The world of finance is a constant gamble. Algorithms change, dows drops, stocks pivot.... it's a never ending game, more intense and bloody than Game of Thrones and a 007 film. That's why its so important to find and listen to the people who become experts in this field. So why do so many of us gamble with our coins based on our own thoughts? Or intuitions? Especially since most of us never got past Algebra II.

Redditor u/weekendbrainsurgeon wanted to hear from those in finance field about bad decisions they've witnessed that we all should never try by asking.... Bankers, Accountants, Financial Professionals, and Insurance Agents of reddit, What's the worst financial decision you've seen a client make?

Tilray Down

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I had a client in her 70s put her whole savings in Tilray stock.

Tilray at the time was trading above 150 per share. I told her it was a terrible idea to put all of her savings in one investment but she told me I was wrong. She argued with me for a good 15 minutes until I relented and said okay, it's your money. So she put 300k into Tilray.

Couple weeks later it starts dropping, I call her and get no answer. It's sitting at 6 dollars a share now, her account is down to about 12k. Last time I spoke with her I took no pleasure in telling her she's no longer my client.


The Truth is Out

Had a client who was extremely wealthy about eight years ago tell us he was no longer going to use our services. Last year we get an extremely angry phone call from his wife asking us why we haven't been filing their taxes. We showed her the paperwork where her husband said he was no longer going to use our services. And then crap hit the fan. This dude apparently just decided he wasn't going to pay taxes anymore and didn't file a return for eight years and had been lying to his wife.

They were rich and owed almost 1.4 million dollars in taxes not including interest and penalties. And oh yeah they got absolutely fried by the IRS. If you are in a relationship with someone you need to be involved in financial decisions. Never let one party handle all of the money and make all of the decisions. That is how bad things happen in both business and in relationships.



I had a client Buy numismatic gold coins with an entire retirement account. She bought 266k worth of coins at almost double the price of bullion. I got the gold salesman on the phone and asked him to justify the reasoning and I he said it was because the dollar was paper money and worth nothing and that gold was going to go to 10000 a coin. I asked him what he exchanged this gold for and he said "well she paid me dollars". Then I said "why would you accept a worthless currency for your rapidly appreciating gold currency?" He cursed at me and hung up and said I didn't know what I was talking about.

I still haven't met a gold salesman that can answer this. Their whole pitch is that the dollar isn't worth anything but they happily take them in exchange for gold coins. The whole thing is crap. Poor lady. She can't sell them now even with gold bullion as high as it is for anything close to what she bought them for.

I am a fully registered advisor just to disclose.


600 Down

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Not my client.

Saw a guy invest about 600k in a start-up. He confirmed in the 1.5 pages agreement that he was fully informed about everything going on.

Please if you invest in that size, ask a lawyer to at least review the agreement.

Needless to say, said guy's net worth is 600k less now.


The Accountants Know

Accountant here.

If you're a small business owner and your business provides you with even a remotely significant amount of income, then get a separate bank account for your business income and expenses and never, never, never commingle your accounts. If you find that you need to make a business payment and you don't have that money in your business account but you do in your personal, then write it down in your books as money that you give the business that then gets spent on the business expense. Likewise, if you want to use your business income, pay yourself a wage or a 'dividend'. The moment you cross your accounts is the moment that you put yourself into tremendous financial paperwork frustrations.


The Lotto Scam

Former manager at a credit union. One seemingly smart lady in her 70s got one of those lottery scam letters saying she won, but needed to send them money to process her winnings. They kept getting her to send more and more money. We were telling her it was a scam from day 1, but we couldn't stop her.

She burned through her IRA which had about 200k. Took out a loan against her paid off house for another 200k. Sold her jewelry. Probably paid out 500k total before finally realizing.

We truly did everything we could. Got her family involved. Several of us would confront her every time she came in and would plead with her to stop.

It was sad but at some point you have to cut your losses and realize it's a scam.

Edit: I was the assistant manager at that point. We brought our risk management department and other higher ups in but they wouldn't close her account.

The whole 500k was not with us. We had no idea about the loan, jewelry and some money in other accounts that she gave out until after it was all over.

She even thanked us later on and wishes she listened to us.


100% Gone

I've made money with both stocks and options but I get on r/wallstreetbets sometimes to see how tf someone can go tits up so easily and omg.... "I have $50,000 in my account, let me throw 100% of that on Amazon puts that expire Friday." Ive also seen people who pull in $1m in their first year and try to tell everyone else how to trade. That's like me hitting it big on a slot machine and then pretending to be an expert.


Chose HULU

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Using ALL of his "retirement" and daughters college tuition to short Netflix. He lost over a million dollars.


"sovereign citizen"

Best friend is a CPA, and when he had his own practice, he had some pretty big-name clients (Senators, musicians, pro athletes, etc.) One of the biggest mistakes people made were thinking they were smarter than an accountant. His biggest challenge were the people who heard about the "sovereign citizen" nonsense. To no one's surprise, a random guy on YouTube doesn't know more than an actual CPA with 40+ years experience. At least a few of these new-found "sovereign citizens" ended up doing time for tax evasion.


Just Exercise

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A private company announced a special dividend to all shareholders as of date of record one-month in the future. $1.30/share dividend.

There was an option holder with 300,000 options at a $0.10 strike price.

He did not exercise them. Had he exercised his options for $30,000, he would have been paid $390,000 the following month.



Not an accountant but I used to do Social Work that included some budget coaching. I was going over one family's monthly budget and trying to figure out how they were going to rearrange so they could pay the subsidized $10 copay for court ordered counseling that would make or break them keeping custody of their children. Now, budget was a little tight because only the dad worked. But he was making just under double what I made for helping them with the budget. And they were living in a gross trailer park where they paid next to nothing for rent.

And this was a step up from the gross motel room they had been living in before. And when I was nicely chewing them out for missing a counseling session, they were all too happy to explain the problem. Which, of course, was dad got paid on Thursdays (weekly) and the Counselor had them scheduled for Tuesdays (weekly.) So, there was no way they would have the $10 left to pay the Counselor on Tuesday.

The solution to this was they had to start driving across town to pay the Counselor on payday, and then drive to their (already paid for) session 5 days later. I was just getting my mind wrapped around this concept, when the mom called me all excited. She had fixed their financial problems. She refinanced their (POS 12+ year old) car. And she was so excited to tell me that instead of paying $385 a month, their new payments were only $115 a week. I still have no words.


Send in the Cars

I've seen people finance cars at over 30% interest. paying $500/mo for a 8-year old mustang, and will end up paying well over 2x the cars value, assuming they pay the loan off.

Edit: since this kinda blew up, here's a PSA for all the active duty (American) military people - any loan you took out prior to either enlistment or deployment is eligible to have the rate reduced to either 6.99 or 7.99% (google it before you call your bank, as it's been a couple years and laws change.) all you have to do is call your creditor and provide them with your orders and they have to reduce the rate, even retroactively, to the date you deployed (or enlisted.. again, google it).



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  1. The client who joined an MLM and racked up half a million dollars worth of losses before finally listening to us and quitting.
  2. The client who spent $40k on Farmville over 3 months.
  3. The clients who give their adult children allowances that exceed my salary, fancy cars, and houses without expecting them to ever hold down a job themselves. vwh808

The Shoo-In....

Payroll accountant. I used to work for a company with an actuarial Department. There was a lovely young woman working in the call center with a masters degree in data science. She was constantly talking about how frustrated she was with making $16/hour in a call center when she had a masters degree in data science, yet no matter how many times I told her to apply to the actuarial team she wouldn't do so.

The actuarial team was HUGE about promoting within. I saw many people who wanted to learn more about what they do who had no experience whatsoever get excepted into the team because they wanted to learn. This girl was a shoo-in. And yet she never even tried despite the fact that there were always openings. She also shared with me that she was $180k in debt for that master's degree. Last time I checked in with her she had left the job completely and is now in school for art. (Insert facepalm emoji here.)

But my favorite was before I was even an accountant. I worked for a small CPA firm as a receptionist during tax time. I saw a full-grown woman sit down on the floor and start crying because she owed $900 in taxes that year when she had made about $150k that year. I rolled my eyes so hard that I hurt myself. Later that day I had a guy who owed $750k to the IRS and said "woohoo! That's way less than last year!"


The Lost Seat

Watched a client walk out of my office after I explained the risk in liquidating his 401K to start his own business. He started it with no management experience or business model, real "fly by the seat of his pants" kinda guy. Wanted to start a career flipping houses in a college town, turn them into upscale rentals. Did it in a bad neighborhood and lost EVERYTHING.


The Background

I'm a CPA and had a client whose business was going under. He started taking out payday loans on his own salary to pay his staff. When it gets this bad with no end in sight, time to reduce staff.

Also in r/accounting someone posted about wanting to file bankruptcy over $900 in credit card debt. This person was about to graduate college with an accounting degree and would have been making $50k starting out.

We all thought he was trolling us, but somehow ended up coming off as a legitimate situation. Who wants to hire a bankrupt accountant which shows up in background searches?!?!



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Probably not the worst, but one of the more perplexingly common...

Making 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 complaining because they can't afford the installment payments on the taxes they owe from two years ago.

Moron, sell your gaudy, gross 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 horrible wife to stop spending all day at the tennis courts sipping mimosas. Get your mess 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.


Don't Spend It! 

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.


Countless Screw-ups....

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 screw-ups and by then it's usually too late to rescue them.


ATM Issues

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Banker. Banks charge fees for using other bank's ATMs.

I had a customer that would check his balance and then do withdrawals daily at a foreign ATM. Guy did not have a lot of money to begin with and because he did this, would overdraw his account and get slapped with an overdraft fee which put him in the hole further. We ended up taking away his ability to overdraw his account. Dude was pissed, but it helped right the ship a little.


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