Worst investment decision ever?

There's a difference between kicking yourself for some something you actually did vs. something you "shoulda woulda coulda" done.
 
There's a difference between kicking yourself for some something you actually did vs. something you "shoulda woulda coulda" done.

Too true. What was that quote from that Sam guy?

“Twenty years from now you will be more disappointed by the things you didn't do than by the ones you did. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.”
 
There's a difference between kicking yourself for some something you actually did vs. something you "shoulda woulda coulda" done.
OK. I shoulda stuck with my Total Stock Market fund purchase instead of getting intoxicated as a consumer and buying that stock. :cool:
 
My dumbest 'investment' was buying a house I was only planning to live in four 4 years. When I started medical school, I decided to buy a house instead of rent. I cashed out my brokerage account ($30k) to put as a down payment. I bought the house for $100k. I sold it five years later for $80k. My portfolio (assuming I didn't make any changes in investments) would have tripled in that time period. Never have I ever had a portfolio that would have tripled in five years since or before. lol. Actual dollars lost isn't all that much, but it's always been a tough pill to swallow for me.
 
^^^ Moral of the story.... think of real estate more as a place to live rather than as an investment. Lots of stories going both ways.... we've been lucky, but that is what it was... luck.
 
My aged mother purchased Portland General Electric. A well-managed local utility that was suitable for a retiree. Enron bought it when I was managing my mother's portfolio. I couldn't figure out what Enron did but their stock was doing very well so I let it be. BIG mistake.

If you don't know what the company is doing don't keep or buy it.
 
Remember Washington Mutual... oh yes. I loved the bank and during the time that I lived on Bainbridge Island the SO of the head of their Mortgage Department helped me resolve a couple of computer issues. One day he said that his companion was leaving the bank, they were moving to Florida, after a big blow-up with bank executives.

A couple of years later WAMU imploded because of bad loans.
 
Worst was a movie investment trust a broker sold me long ago.
 
I had $64,500 in a little company called Hansen's. It made 'triple filtered' sodas and specialty drinks. Knew it was a great company. Met my soon to be wife, and decided to use that money to pay off her house. This was around the beginning of the year 2000. Hansen's went on to become Monster Beverage Corp. The $64.5k would now be approx 60.5 million. Sad thing is, this is the 2nd 'worst investment decision' I've made. Don't want to even get in to the first....sigh.
 
About a year after I was let go from Megacorp, and while we were getting ready to move home from the US to Canada, I decided to liquidate my portfolio of Megacorp stock and put it into Vanguard target funds. The stock was trading at an all-time high, and once we were back in Canada, it would be difficult (if not impossible) to trade in our US investment accounts (so a target fund that adjusted over time was perfect).

I did make a significant profit (I had acquired about half of the stock in the depths of the recession) and the Vanguard investment has done well, too, but the Megacorp stock traded up even further - about 80% higher than the prices I sold at.

It's not an investment, but the other money decision I regret is selling our Canadian house in 2013 when we were having trouble finding a reliable renter. If we had hung on to it, we'd have a nice, paid off house closer to the centre of the city. We are very happy with the bigger house that we acquired, after the market had trended up significantly, but we'd be better off financially - and much closer to retirement if we'd hung onto the smaller house.

Both decisions were made because I'm relatively risk-averse and those decisions allow me to sleep at night. But still ...
 
I had $64,500 in a little company called Hansen's. It made 'triple filtered' sodas and specialty drinks. Knew it was a great company. Met my soon to be wife, and decided to use that money to pay off her house. This was around the beginning of the year 2000. Hansen's went on to become Monster Beverage Corp. The $64.5k would now be approx 60.5 million. Sad thing is, this is the 2nd 'worst investment decision' I've made. Don't want to even get in to the first....sigh.

Oof! That hurts. I guess I should have also mentioned the five bitcoin I sold about a year ago for $50k. I doubled my investment when I sold and was happy... However, those same five bitcoin are now worth over a quarter mil now... I don't consider it a bad investment because I doubled my money in just a few months, so really it was a great investment... But I never expected it to keep climbing like it has.
 
Oof! That hurts. I guess I should have also mentioned the five bitcoin I sold about a year ago for $50k. I doubled my investment when I sold and was happy... However, those same five bitcoin are now worth over a quarter mil now... I don't consider it a bad investment because I doubled my money in just a few months, so really it was a great investment... But I never expected it to keep climbing like it has.


And you should feel good that you kept track of your key and the location in which you held your Bitcoin. On podcasts, I’ve heard horror stories of people who bought Bitcoin years ago when it was a couple bucks but now have no ability to trade them, because they got rid of the old computer without transferring the old files, lost track of the digital wallet or the key.

Ugh. Is “Password Risk” a new investing phenomenon?
 
Last edited:
And you should feel good that you kept track of your key and the location in which you held your Bitcoin. On podcasts, I’ve heard horror stories of people who bought Bitcoin years ago when it was a couple bucks but now have no ability to trade them, because they got rid of the old computer without transferring the old files, lost track of the digital wallet or the key.

Ugh. Is “Password Risk” a new investing phenomenon?

I bought mine through Robinhood. They don't have many choices for crypto, but it's all commission-free. To be honest, I have no idea how that crypto key stuff works. I've read these types of stories too, including some with hundreds of millions of dollars worth of bitcoin, but no way to access them. How sickening.
 
Okay, I'll play. In the early 1980s, DW and I bought Willie-Nelson style "abusive" tax shelters. We bought from a dealer - "friend." To add insult to injury, the underlying deal was a FRAUD - the guy was selling the same thing over and over. SO the tax people crucified us and the investment itself was worthless. As best we understand it, the original "guy" did no time and don't know if he was even fined. For certain, there was no restitution. But, in the end, we made the tax man happy. Another notch on the belt. It was an expensive lesson - well learned. YMMV
 
I put 1/3 of my net worth in SDLP at $5/share. Now it's worth around $.10/share after a negative 10/1 split making my $80K investment now worth about $160.
 
I put 1/3 of my net worth in SDLP at $5/share. Now it's worth around $.10/share after a negative 10/1 split making my $80K investment now worth about $160.

I am sorry you had that experience Aaron. If it helps any, and it probably doesn't, consider that there was one man who lost 800K in March of 2020 putting it all in 2X mortgage reits. Another individual lost 700K in the same type of product. Poor guys. They both lost everything.

I invest in mortgage reits , but not 2X. After I lost 5k in 2000 during the dot com craze investing in a single stock,I am more careful now. 5k doesn't seem a lot to me now, but back in 2000 it had a much bigger impact to my bottom line and it taught me a lesson.
 
Last edited:
So far I've dodged major bullets. But tomorrow is another day. :)

Seriously ... I got snookered by a whole-life insurance guy when I was 22. It took me till I was 51 to wise up and cash it in ... after all those years of paying $25 a month.

My wife and I have no kids, retirement savings are solid ... and the last thing I need is whole-life insurance. My $25 a month is better spent on takeout dinner to support a local business.
 
I put 1/3 of my net worth in SDLP at $5/share. Now it's worth around $.10/share after a negative 10/1 split making my $80K investment now worth about $160.


I had to look up SDLP because I had no idea what it was. I wasn't too surprised it was oil related. Oil is famous for boom and bust.
 
A Piper Jaffrey broker talked my dad & I into buying 100 shares of Beefsteak Charlie's...... I still have the stock certificate in my file cabinet..lol
 
I was 100% in dotcom mutual funds in the 90s. My net worth went from 276k down to 15k after the crash. I switched to S&P 500 index fund after that. Amazingly I had enough money by early 2017 to retire at age 51. I never had a large salary, I hit 30k in salary at age 41 and made around 48k my last 6 years or so before retiring. My net worth is up 74% since retiring.
 
Last edited:
I was 100% in dotcom stocks in the 90s. My net worth went from 276k down to 15k after the crash. I switched to S&P 500 index fund after that. Amazingly I had enough money by early 2017 to retire at age 51. I never had a large salary, I hit 30k in salary at age 41 and made around 48k my last 6 years or so before retiring. My net worth is up 74% since retiring.


That last part would be a cool thread in itself "My net worth is up 74% since retiring". Seems most retirees on these boards have seen net worth go up since retiring, wonder what the average is.
 
That last part would be a cool thread in itself "My net worth is up 74% since retiring". Seems most retirees on these boards have seen net worth go up since retiring, wonder what the average is.



There’s a different string happening now about that. Most seem to have several sources of income and, therefore, have very low withdrawal rates, so no wonder their portfolios have grown a lot.

I’ve been fired 6 months at 54 and just have a different strategy to spend more up front while we’re healthy, before SS and, eventually, liquidated home equity engage. The trade off is, I likely have to watch the portfolio drift downward until about age 70, when it stabilizes and increases later in life. It could turn out to be “my worst investment decision ever” or the best. YMMV.
 
Left Apple a year before Jobs returned. Stock price at the time (accounting for splits) 0.15/share.
 
Back
Top Bottom