<img height="1" width="1" style="display:none" src="https://www.facebook.com/tr?id=131147930823002&amp;ev=PageView&amp;noscript=1">
Advertising & Editorial Policies

We all have coulda-shoulda-woulda stories about money and investing.

You know, that red-hot stock you never saw coming. Or your brother-in-law's stupid business venture you lost a bundle on. Or that now-valuable collectible you tossed out years ago.

Some financial flubs are easily shrugged off. But others can't be forgotten quickly, because the dollar amounts end in way too many zeroes.

What's the worst investment or financial decision you've ever made? Check out some of the epic errors with money that Reddit users are willing to admit to.

And if you need investing help, automated investment service Wealthsimple is offering to manage up to $10,000 free for one year for MoneyWise readers.

16. When cash is trash

Cropped image of man counting fifty dollar bills at home
Andrey_Popov / Shutterstock

For me it was taking my entire IRA and selling everything — holding cash.

I did this in late 2012 when someone told me that 2013 would see another big dip. I've been in cash since watching the market hit record high after record high.

I won't buy in now because "it can't possibly go any higher and must come back down eventually."

My account would likely have been double by now.

| danlozo

15. Dad, you're embarrassing me!

An investor is looking at screen showing stock market crash
Kenishirotie / Shutterstock

When I was in high school, with the help of my dad I bought 100 shares of WorldCom when it was at $15 with some money I had from summer jobs.

I wanted to cash out when it went up to $30 to double my money. He wouldn't let me :(

My dad wanted me to keep the stock as a long-term investment. WorldCom execs were fraudulently adjusting the books to show profits and when it was found out, the stock almost instantly became worthless.

| Micotu

14. Take my timeshare, please

Asian businessman is selling timeshare at ocean shore to his rich client. Concept of realtor's work
ImageFlow / Shutterstock

Timeshare!

We got a great deal on a secondhand timeshare. I foolishly thought it would appreciate like real estate. We can't find anyone to take it for free.

We are wasting $600 a year and are thinking of recursing ourselves. That would mean that we pay three years upfront and are done with it.

| yoeddyVT

13. Panic-stricken

Market Rebounds
2121fisher / Shutterstock

During the 2008 financial crisis, I sold a bunch of stocks at a loss. Ended up with, I think, $15,000 in actual losses and more in paper losses.

A couple years later, everything I sold had more or less doubled.

I'm never panic selling again.

12. Bad Investing 101?

Recent college graduate upset about tuition debt, horizontal
Burlingham / Shutterstock

Worst (investment)? Honestly, college.

I'm $100,000 in debt for a bachelor's degree where I'll never make more than $40,000 a year.

I thought my major was more lucrative, but definitely not.

| alrashid2

11. An Apple iMiss

Berlin, Germany - February 7, 2018: iMac G3 computer. The iMac G3 is a series of personal computers designed, manufactured, and sold by Apple Computer, Inc. from 1998 to 2003
Cineberg / Shutterstock

I thought it would be a good idea to invest in Apple in the 1990s when they were first coming out with the iMac.

I was in middle school, had $30,000 or so in the bank from inheritance, and I told my mom I wanted to invest in Apple, but she shut it down.

A friend of mine who was a fellow Apple enthusiast thought I'd end up losing money, too, so I didn't press for it too hard.

The stock price at the time was around $40, and I know since then it has had two 2-1 splits and a 7-1 split. I'd be a millionaire.

| kjuca

10. Lost the relationship, then the house

lost keys on the floor in front of the door
OndroM / Shutterstock

Stupidly getting married at 19, and then immediately putting all of my savings and gifted money over the years into buying a newly built house for us.

I had no idea who I was at 19 (neither did he), and the home was in a dead-end country town that I just always assumed I'd never leave.

I couldn't afford the house payment on my own when the relationship deteriorated, and I ended up owing money at closing to save my credit.

Luckily I learned my lesson and have made much smarter choices since then, but I do wish I hadn't blown all of that cash so young.

| Ualritem8

9. The wrong chemistry for investing

Confused Nerd
lassedesignen / Shutterstock

None of my biotech investments have made money, and some have tanked more than 50%.

I have an advanced degree in the sciences (specifically pharmacology) so I thought that I understood the value of the products being developed and the quality of the leadership teams running the companies.

I clearly don't and generally stay away from them now.

There's no lesson there other than I don't know what I'm doing.

| knotswag

8. A yogurt swirl

Cup of Vanilla Frozen Yogurt with Sprinkles Against a Purple Background
appleboxcreative / Shutterstock

I took $135,000 and opened one of the first frozen yogurt shops in our area. I was advised against it because it was a "fad." I profited $90,000 in the first year.

Fifteen months after I opened, there were 11 shops within a 10-mile radius. I lost $45,000 in year two and $60,000 in year three.

I closed the shop down (and lost) $150,000 overall when the landlord strolled in one day and offered me an out because a neighbor wanted to expand.

Luckily I was able to sell equipment for a decent amount — but still a major mistake with zeroes at the end of it.

| cjw908

7. Bad pennies

Pennies Scattered on White Background
tylercb54 / Shutterstock

My first trade was $10 of some penny stock.

The fee for buying these stocks was $10, same for selling them.

So I was down 100% from the get-go, and if I wanted to sell them immediately after I would be down 200%.

| Tresher

6. Beers or company stock? Beers, please

Multiracial group of friends enjoying a beer
DisobeyArt / Shutterstock

I worked for Nortel — we had an employee stock purchase plan, and over a couple of years I bought a few thousand dollars' worth.

There was a joke that the people that bought beer instead of company shares came out better because the deposit on the empty bottles was worth more that the shares at the end.

[Phone equipment maker Nortel Networks' 2009 bankruptcy was the largest in Canadian history.]

| SomeGuyInOttawa

5. Why you should never raid your 401(k)

401k penalty warning, Yellow and black warning road sign with text 401k penalty with sky background 3D Illustration
karen roach / Shutterstock

(My worst investment was in) a small startup that was supposed to revolutionize the marketing industry back in 2003 using subjects shopping with small wearable cameras.

A co-worker sold me on the idea — he actually quit to work for them.

I didn't have the money, but didn't want to miss such a great opportunity, so I pulled it out of my 401(k).

Completely losing the $5,000 wasn't the worst part. Owing the IRS taxes on the money and an additional 10% was the worst part.

| gravityrider

4.Orange would have put you in the black

Orange Is the New Black, Season 6, Taylor Schilling
JoJo Whilden / Netflix

I bought in to Netflix when it bottomed out in 2005.

I thought it wasn't going to get any better than $60-$70 a share, so I sold.

[Today, Netflix is the home of hit shows like "Orange Is the New Black," and the stock is worth about 300 times what it was at its low point in 2005.]

| captkrisma

3. The bottom of the deck

House of cards close up.
Zharate / Shutterstock

I owned 700+ shares of Sprint. WorldCom offered to buy them out at $65 a share. I was sure there would be a bidding war so I held on to the shares.

As you may or may not remember WorldCom was a house of cards, one card slipped and the entire deck collapsed along with the $65 bid and my fantasized bidding war.

So instead of $45,500 for my Sprint shares, I eventually sold them for $3,800 and got to take a tax loss.

What I learned is that if you own a stock and you get a buyout, sell the sucker. Don't hang around waiting to make an extra buck. Deploy the capital into one of the stocks on my wish list right away.

| txholdup

2. Two the hard way

Concept of classic casino code 7-7-2-7-7 lucky numbers roulette wheel with black and red sectors and white ball
Sergey Hmelevskih / Shutterstock

The year is 2008, and half a dozen giant banks are on the verge of bankruptcy. There is talk of a government bailout for some, but not all of them. The stock prices are very low, but this is a gamble if there ever was one.

"Why don't I pick two?" I think. Which two should it be?

I go all-in on Lehman Brothers and Washington Mutual.

[Both collapsed in 2008. Lehman Brothers was the largest bankruptcy in U.S. history, Washington Mutual was the largest U.S. bank failure.]

| danlozo

1. His most ex-pensive investment

summer holidays, dating and relationships concept - stressed man with woman outside
Syda Productions / Shutterstock

My ex-wife.

No, seriously, that choice of spouse cost me more than I will ever lose investing.

(Bleep), it probably cost me more than I will ever make.

| Resipiscence

Via Reddit.