What's the most money you lost in the dumbest way?

Timeshare

Was it a really good taco, served with an extra napkin?

Do opportunity costs count? I saved for several years to buy a new car. If instead of just dumping all that money in a savings account I’d put it in an index fund, I’d have had enough extra to buy a much nicer car. Of course, if I could predict the stock market then money wouldn’t be an issue.

Another opportunity cost that is much more predictable, and completely my fault was when I moved from my condo to my house. The plan was to rent the condo out, but it had to be prepped for renting. Because I’m lazy, I ended up taking about six months to do two weeks worth of work. So that ended up being 4-5 months of missed rental income, which would have been real nice with two mortgages.

When my brother died, his widow asked me for a loan to tide her over until the insurance kicked in. I wrote her a check for $5000 on the spot. Last I ever saw of that money. Much as I loved my brother, I could never stand my SIL. He told me once that he had $2,000,000 of insurance.

I think I’d win this thread but I don’t feel like talking about it right now. It was a lot of money, and a stupid reason.

The company I used to work at had a 401K. Then it got bought by a competitor. The new owners didn’t do 401Ks but we could move our 401K money into the new owners Employee Stock Ownership Plan. It went up for a while and then the new owners went bankrupt and I lost it all. About 13,000 bucks.

Oh, a friend of mine told me I should check out this store. So I checked it out.

First red flag–not a literal red flag. It’s an entire building in a prime real estate area dedicated to this one store.

Second red flag–it has its own parking lot. See there is really no such thing as free parking. If there’s a place to park, someone is paying for it, and if it’s adjacent to retail, that person is…whoever buys there. Oh, it’s you either way, if you don’t put money into an actual meter you will pay some other way. Yes.

Third red flag–I walk in, and there is a marble bar with champagne in an ice bucket, and orange juice in another ice bucket. As soon as I walk in someone asks if I would like champagne, or a mimosa, or maybe just water?

Guys, I did not leave. I should have, and I knew it. Just get right the hell out of there. But I didn’t.

God knows what I’d have spent if I’d had the champagne.

I divorced in 1979. In February of 1980 we sold our house, on contract for deed. He got the down payment, less fees, and I got the difference between our mortgage payment and the buyer’s. So I got about 470 a month for thirteen years. More than he got.

But…when I would pay the tax bill for the house it still had both our names. Found out that to get that changed I had to do what is called “a petition of quiet title.” **See, some paperwork that should have been done at time of sale, in which the ex would formally declare he had no further interest in the house, had not been done.
**
Since I had no idea where the ex was(it had been twenty-eight years) there were all kinds of fees for publishing legal notices. I even had to fork over money to pay a second lawyer to represent his interests. All in all I was out about $2500 dollars.

We dilly dallied on our way to the airport and ended up missing our flight. Ended up buying tickets on another airline for a total extra cost of about $1,000. On the upside we got an extra day of vacation.

And timeshares. I have to wonder if anyone has ever had a good experience buying a timeshare.

It happens. My gf bought a timeshare in St Martin back when timeshares were a new thing, maybe 30 years ago. I’ve gone there with her the past 13 years, it is our “second home”.

Although the various maintenance fees and such mean that it wasn’t the best financial choice, we do not mind putting money into their economy. When the opportunity has arisen to unload the timeshare, she has chosen not to.

Spent about $80,000 to go late model stock car racing. Brand new racing chassis, brand name racing engine, lease truck and trailer to tow it all around. Had a sponsor for tires, that alone saved me $15,000. My goal was to do well enough that someone would consider me to drive their car. Learning curve was steep but made good gains. Towards the end of the season put together a string of good runs, including a 3rd place at Anderson Speedway in California against some of the top late model drivers on the West coast. Sold the car and equipment at the end of the season for $22,000. The buyer took the car to Phoenix International Raceway that November for a NASCAR Southwest tour race and won the race with a much more experienced driver than me. The only thing he changed on the car was the number. I figured the whole experience cost me $64,000.

Forty years ago I borrowed $10,000 from a friend. Paid him back $200 a month plus any overtime I made. All well and good. Ten years ago he came to me needing $6000, he helped me so I returned the favor. Never saw a penny paid back. More disappointed than angry. Then he died. I could afford to loan him the money so it didn’t disrupt my life in any way. If you EVER loan money out think of it as a gift. That will keep you sane.

Yeah, I loaned a friend $20,000, with no time limits, no interest charged, and no payback plan. Though he’s a generally honest guy, I don’t really expect to get it back - it was a gift in all but name. Though if he does pay me back it’ll be one hell of a surprise windfall. (I specifically told him I’d prefer to be paid back all or nothing, mostly on the thinking that that would be the funnest way to get paid back. I suggested that if he really wanted to pay me back he should put together some kind of savings fund and dump money into it until he felt he could afford to pay me back out of the surplus.)

I didn’t mention this in this thread previously because, like with most of my silly and/or reckless expenditures, I don’t regret them or think they’re dumb.

Well, in the Midwest US, my house that was purchased in 2001 was worth less than the mortgage until around some time last year. It probably still is because it needs some repairs I really can’t afford.

When I was 17, staying in a hotel waiting to be shipped off to basic training, I got taken for $60 by a guy running a 3-shell game in the lobby. I was so young, it looked so easy to beat. At least I learned from it.

As I write this, around $4700 Canadian, but it varies.

You see, I have half a bitcoin. I bought it on a whim for $10, back in the year of the big quake in Japan (2011). I played around with it for a while, then stuffed it into an encrypted disc image and forgot about it.

A couple of years later, when I was at school, someone mentioned that bitcoins had gained a lot of value. I suddenly remembered my half-a-bitcoin, and, being a starving student, went to get it out and maybe sell part of it.

I quickly found the file containing the half-a-bitcoin. But there was a slight problem. The file was an encrypted Macintosh disk image… and I had no idea of the password. None.

I remembered making a special difficult password that was a sentence, and putting the extra-strong encryption on the disk image, but i remembered nothing more. Without the password, there was (and is) no way to open the disk image and retrieve the bitcoin wallet file within.

So there it remains, in my computer, taunting me: a Mac disk image with potentially thousands of dollars inside. As the price of bitcoin rises and falls, I occasionally think about ways to get at it. One time I actually spoke to a hypnotist to see whether she could help me remember. No such luck. Laughing, she said that hypnotism doesn’t work that way…

Maybe someday I will remember that password.

My neighbors had a timeshare up in Park City near the ski resorts. Although it’s an easy drive from Salt Lake City, using it they had a great time up there.

When I was setting up a PGP account, for the password I used the first complete sentence at the top of page 25 of a favorite book of mine. All I had to do then was not lose the book, or at least ensure the library had the same edition.

Tripolar is like me, but I only come in 4th place: divemaster and racer72 also had bigger losses than any of my individual blunders.

… Unless I count my entire career as a big mistake. I was making $100/hour (and enjoying the work) in the early 1990’s with my prowess still growing, but said Screw It! — retired (with a relatively meager nestegg) to spend my final decades relaxing and raising kids with the woman I loved.


Necessarily frugal, but happy.