Worst investment decision ever?

[JoeWras]

Oh boy. If Domino’s Pizza is the food the built America, that explains a lot. In my life, it was just the food that fed the late night munchies in college.

That subject is addressed. And it was THE reason for their initial success. Later was the 30min guarantee.

 

[kcowan]

I think we all have some sudda-wudda-cudda events that could have gone differently. One thing I know is that everyone thinks people are crazy if they hold too much of a stock!

FIL held only his company stock forever until it was worthless Addressograph-Muiltigraph. The people that made the hard copy credit card click-click machines. We advised him to sell and he said that would be disloyal. Inheritance = 0!

 

[pacergal]

Universal Whole Life Insurance.
Didn't't really understand it when we bought it in our early 20's( mistake #1), was pitched as "an investment" that was life insurance, where "dividends would pay for insurance within 10 years".(believing that--mistake #2)
Expensive, never really got to the point where the dividends covered the premium.
We cashed it out several years ago.

 

[pdxgal]

It's said you regret the things you DIDN'T do, rather than those you did. My worst investment decision (in hindsight of course) was to NOT buy a condo in a San Francisco building where my boyfriend at the time had just bought a pied-a-terre. I was in escrow with a $10k down payment, when I decided I didn't really like the place that much (the cheapest in a high end building, basically a concierge unit on the ground floor, next to a public right of way). In retrospect it would've been good to buy it anyway as a rental. Today would be worth about $1M. The condo I did end up buying for myself (and turned into a rental when I was laid off and moved) has turned out to be one of my better investments, thanks to the power of leverage and the appreciation of the SF real estate market. Hindsight's 20-20.

 

[Bryan Barnfellow]

Not an investment decision, per se; but I was offered a job in the 1970s as the first employee of a small store near my university. It sold peasant dresses, lava lamps, and various household stuff. Loved the store, but hated the prospects, given the owner was a recent Peace Corps volunteer and had a dream of a second suburban location. Also I was on track to get a PhD and work in academia.

You know it today as Urban Outfitters. :-(

-BB

 

[pdxgal]

Bryan, your story reminds me of a similar shop in my CA hometown in the 70s. They sold army fatigues, incense, parachute pants and other funky stuff. It was called Banana Republic. Then there was the guy who bought an old postal annex in town and started selling gardening supplies. That was Smith & Hawken. We may need to start another thread about six degrees of separation from successful entrepreneurs (though maybe there are some of the latter on this site!)

 

[Walt34]

My most expensive mistake was marrying the wrong woman. But as Dad was fond of saying about life's screw-ups "You chalk it up to tuition and life goes on". And I'm fairly sure that I wouldn't appreciate DW as much as I do if I hadn't been through that experience first.

The second most expensive purchase was an airplane (a Piper Tri-Pacer) in 1975 for $3,900. It is a four-passenger airplane, if the people are skinny and like each other. I kept it for two years and had a ball with it and it was the fulfillment of a childhood dream of learning to fly an airplane. I do not regret that choice. It was the money from the airplane that paid for the wedding and honeymoon with wife #1. It would have been cheaper to keep the airplane.

 

[CyclingInvestor]

Buying my first house in 1981 rather than starting my stock investing career earlier with the $20k down payment. My rent at the time ($240/month in Manhattan Beach) was less than half my new mortgage payment.

 

[Onward]

Selling a bunch of Yahoo! in the single digits, before it took off.

What a yahoo I was.

 

[Ronstar]

Apple was also involved in my worst investment decision. In 1983, I couldn’t decide whether to buy an Apple II computer or invest the money in Apple stock. I bought the computer.

 

[CRLLS]

Heck, I could put up with a "maniacal narcissist",
for a lot less than $200 billion.

Once I had enough annual return on my investments to cover my expenses I would be out in a flash. See the all of the threads titled "How much is enough." or "Enough - How much is that?". I do admit to sucking it up to a boss like that when I wasn't financially ready to leave.

 

[Markola]

Should have stayed in our small starter house longer after we remodeled it, rather than moving to a larger and more expensive one whose mortgage and maintenance pinched our ability to save in our retirement plans during those earlier career years. Oh, well. Can’t look back.

 

[MRG]

My worst was leaving some retirement money at Megacorp in their profit sharing. I did that to have a second source of monies when I retired at 56 via rule of 55.

It was a good fund for many years, turns out the fund manager allowed Megacorp to tilt the fund into some hot sidebets. Our existing Megacorp management team had recently retired and the new management team was a bunch of good looking idiots.

They allowed a side bet to become over 50%, yes over half the fund, was allocated to a risky biotech, that went bankrupt! This company borrowed business practices from pharmabro and were shut down.

Thanks to a friend I joined the proper lawsuit and have collected 10k, from the fund managers, to date. I should have arbitration against Megacorp sometime this year. So far we have been winning all the judgements and it looks like people are being made whole. I thought my friend was awarded 100k, I reviewed our communications and the attorneys were awarded 100k for her settlement, she got 250k. Since it'san ERISA protected retirement fund the attorneys fees are awarded separately. I'm glad I got into this suite, about 10k of my former co-workers are in another suite where they will each receive $47. For many this was their entire retirement, they'd been convinced of the safety of this fund.

 

[JoeWras]

Should have stayed in our small starter house longer after we remodeled it, rather than moving to a larger and more expensive one whose mortgage and maintenance pinched our ability to save in our retirement plans during those earlier career years. Oh, well. Can’t look back.

I like neighborhoods with modest homes. It also keeps you grounded.

I don't know if this was true in your case, but for many people, when they move up they not only have the mortgage and maintenance, but they also tend to get infected by a bit of lifestyle creep which can be very costly.

 

[kcowan]

Apple was also involved in my worst investment decision. In 1983, I couldn’t decide whether to buy an Apple II computer or invest the money in Apple stock. I bought the computer.

Never owned an Apple computer until 2010. Bought their stock just after Jobs came back. Still hold half of it!

But I am on my second wife. Thought it would be costly but she ended up being worth what I am due to divorce settlement and inheritance. I invested the inheritance for 5 years for MIL. Followed exactly what her AUM did but saved her mega bucks by doing it better and cheaper. Switched to equity after the inheritance.

 

[Fermion]

Actually an Apple I computer is worth about $900,000 today so it wasn't the most horrible of investments..what did it cost, $500? That isn't a bad return.

 

[BoodaGazelle]

During the Internet heyday, I turned down an offer to be an early employee at a Boston-area startup. The founder must have made at least $100M. I would certainly have made a few $M.

I ended up okay, and made far less at another startup, but I have a good cocktail party story.

 

[stephenson]

Being an absolute Apple fanatic from the first Mac - and never buying a single share of Apple.

Buying, in 1976, the incredibly gorgeous, to a 22 year old Navy guy and wife, house in Lisbon Falls, Maine that had been the rectory for the Catholic church. Beautiful.

Sniff.

 

[Markola]

I like neighborhoods with modest homes. It also keeps you grounded.

I don't know if this was true in your case, but for many people, when they move up they not only have the mortgage and maintenance, but they also tend to get infected by a bit of lifestyle creep which can be very costly.

No doubt about it. Perhaps unconsciously, one’s spending is influenced by how others in the neighborhood are spending.

 

[RobbieB]

We ate a lot of Dominoes "double cheese, sausage and mushroom" back in the college days. They were better then.

 

[unclemick]

Still have 5% share in a Gold mine in Colorado.

Non Working. Came close to selling it to The Boy Scouts for a campground in the 70's.

Heh heh heh - Nothing close to the original post though.

 

[dmpi]

Remember Fannie Mae? Remember Washington Mutual?

 

[pb4uski]

Buying Evergreen Core Bond Fund in my employer 401k in the early or mid 2000s thinking it was a core bond fund... perhaps it was when I bought it. Anyway, when the Great Recession hit it took a much bigger hit than Vanguard Total Bond did and after further research I discovered that fund management had made big bets on mortgage backed bonds that had sh!t the bed.

 

[JoeWras]

Being an absolute Apple fanatic from the first Mac - and never buying a single share of Apple.

Buying, in 1976, the incredibly gorgeous, to a 22 year old Navy guy and wife, house in Lisbon Falls, Maine that had been the rectory for the Catholic church. Beautiful.

Sniff.

Being an absolute XM radio fanatic in the early 2000s, and buying 100s of shares. Watching it go down, getting gamed by reddit-bro types, and getting fed up and selling near the all time low.

Hey, at least the loss was a balance against some gains I was finally getting.

 

[Still Learning]

My wife joined me in early retirement January 2020 and our Vanguard funds were very conservative at about 20/80 stocks/bonds. In March with the Covid hit we became even more conservative at 90/10. My mistake was to wait too long getting back into stocks. Today our funds are roughly 55/45 and doing much better.