# What's the most money you lost in the dumbest way? **URL:** \ **Category:** Miscellaneous and Personal Stuff I Must Share\ **Created:** [December 18, 2019, 4:59pm UTC](https://boards.straightdope.com/t/whats-the-most-money-you-lost-in-the-dumbest-way/845030 "2019-12-18T16:59:07Z")\ **Posts on this page:** 20\ **Page:** 4
**Author:** ![BrickBat](https://avatars.discourse-cdn.com/v4/letter/b/ac91a4/32.png) [@BrickBat](https://boards.straightdope.com/u/BrickBat)\ **Post date:** [December 21, 2019, 7:11pm UTC](https://boards.straightdope.com/t/whats-the-most-money-you-lost-in-the-dumbest-way/845030/61 "2019-12-21T19:11:18Z")
> [@Nightfall1](#): > > If you EVER loan money out think of it as a gift. That will keep you sane. Blunt but true; though it took me years to figure out. In the vast vast majority of cases, if they need money that acutely, they can’t afford to pay it back and likely never will be able to afford to pay it back. Oh, I’ve seen some inklings of good-faith effort, such as paying back a small portion…once, or a pretty good sized hunk of it mailed to me as a check…only to have them call me back very shortly after and ask me to please not deposit said check. When I hear the gushing "thank you, thank you, thank you"s and “I’ll pay you back…I will”, I just wave a hand and say “Ahhh, forget it”. ---
**Author:** ![Corry\_El](https://avatars.discourse-cdn.com/v4/letter/c/ecae2f/32.png) [@Corry\_El](https://boards.straightdope.com/u/Corry_El)\ **Post date:** [December 21, 2019, 8:49pm UTC](https://boards.straightdope.com/t/whats-the-most-money-you-lost-in-the-dumbest-way/845030/62 "2019-12-21T20:49:06Z")
> [@Nightfall1](#): > > 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. Right in which case you won’t really think of it as losing money. 🙂 In our case it was lending to (my) inlaws, (a classified amount, unfortunately larger than your case). What added insult to injury was that I couldn’t talk to anyone about never getting most of it back. According to my sister in law, and nominally agreed by my wife, it was all paid back (by some kind of new math, this included a currency conversion and occurred over years, but we did _not_ get nearly all our money back 🙂 ). And I didn’t want to admit to anyone else I’d gone along with such an idea in the first place. Wife and I have reached a peace accord over it: we agree to disagree whether we got paid back (she knows we didn’t, but knowing it and saying it are different) but not discuss that particular loan again; and we both committed to only ever ‘lending’ to family again if it’s considered a gift and approached that way from the start. ---
**Author:** ![DummyGladHands](https://avatars.discourse-cdn.com/v4/letter/d/49beb7/32.png) [@DummyGladHands](https://boards.straightdope.com/u/DummyGladHands)\ **Post date:** [December 22, 2019, 1:33am UTC](https://boards.straightdope.com/t/whats-the-most-money-you-lost-in-the-dumbest-way/845030/63 "2019-12-22T01:33:14Z")
Beta & VHS libraries my late husband built ---
**Author:** ![TokyoBayer](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/tokyobayer/32/13989_2.png) [@TokyoBayer](https://boards.straightdope.com/u/TokyoBayer)\ **Post date:** [December 22, 2019, 1:55am UTC](https://boards.straightdope.com/t/whats-the-most-money-you-lost-in-the-dumbest-way/845030/64 "2019-12-22T01:55:33Z")
My best friend of 20 years carefully constructed a lie over the course of a year and got me to invest with him in a business. I put in $20,000 but fortunately got wise early enough that i only lost about $3000. I met him when we were both working at Trolley Square shopping mall \*for those who know Salt Lake(. Both of us were students and we both had gone to Japan on LDS missions. He and I went on to both marry Japanese women. He was the best man at my first wedding. We worked together from 6 am to 10 pm, six days a week, remodeling my mother’s home over a summer. We were closer than brothers and kept that way for 20 years. For one fucking year, he lied about everything, big and little and it was all a hoax. He was teaching English and had gotten tired of it. He had a plan of how to get out of it with a particular type of business and needed some money to try it out. For a year, he carefully lied to me, telling me how one particular aspect was working well, then how another was succeeding. Little hickups, some setbacks and then more success. Once I was convinced, I invested and he started, but things didn’t go like he said they would I became suspicious and asked to see the books from the initial phase. He made excuse after excuse and I finally realized my best friend was lying through his teeth to me. Fortunately, we had only spend several thousand dollars and not the entire $20k. We haven’t spoken since. ---
**Author:** ![Musicat](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/musicat/32/20189_2.png) [@Musicat](https://boards.straightdope.com/u/Musicat)\ **Post date:** [December 22, 2019, 2:45am UTC](https://boards.straightdope.com/t/whats-the-most-money-you-lost-in-the-dumbest-way/845030/65 "2019-12-22T02:45:35Z")
“Lent” $20 to a neighbor I had the hots for, and who gave me some sob story about not having cash to pay some bill. Fully expected to be scammed, but sex trumps logic, and I was right, dammit. ---
**Author:** ![JKellyMap](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/jkellymap/32/15880_2.png) [@JKellyMap](https://boards.straightdope.com/u/JKellyMap)\ **Post date:** [December 22, 2019, 12:27pm UTC](https://boards.straightdope.com/t/whats-the-most-money-you-lost-in-the-dumbest-way/845030/66 "2019-12-22T12:27:44Z")
1. Stepping off the bus the first day in Istanbul, Turkey, I miscounted the zeroes on the lira bills, and paid ten times the price for some sandwich or something (the seller knew he was fleecing me). 2. Afraid of capital gains taxes, I ignored my advisor’s advice to sell stock in a certain bank early in the 2008 economic crisis. Ended up losing several grand, needlessly. ---
**Author:** ![bizerta](https://avatars.discourse-cdn.com/v4/letter/b/3be4f8/32.png) [@bizerta](https://boards.straightdope.com/u/bizerta)\ **Post date:** [December 22, 2019, 11:44pm UTC](https://boards.straightdope.com/t/whats-the-most-money-you-lost-in-the-dumbest-way/845030/67 "2019-12-22T23:44:26Z")
> [@HMS\_Irruncible](#): > > 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. I was watching a game of Follow The Queen. At one point, I was pretty sure it was #2, but I knew for sure it was either #2 or #3. Someone eventually bet $50 on #3, but it turned out to be wrong. Then the grifter offered anyone else to bet on either #1 or #2. I was seriously tempted, but someone else bet $50 on #2 faster that you can say Jack Robinson. Apparently he had reached the same conclusion I had. Needless to say, the Queen was #1. I later suspected the first bettor was a shill. ---
**Author:** ![StGermain](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/stgermain/32/2868_2.png) [@StGermain](https://boards.straightdope.com/u/StGermain)\ **Post date:** [December 22, 2019, 11:53pm UTC](https://boards.straightdope.com/t/whats-the-most-money-you-lost-in-the-dumbest-way/845030/68 "2019-12-22T23:53:49Z")
Not counting horses? When I was in my 20’s my sister and I lived together. She was a single mother with 2 kids, I was a hard-working wage slave making slightly more than minimum wage. She was constantly borrowing from me. I kept the running balance of loans/pmts on a wipe-off board on the refrigerator. At this point that the board was “accidentally” erased, she owed me about $1200 - a lot of money when you make $6/hr. She gave me $200 and told me she thought that covered it. And then there was the time I was staying with my brother. I’d driven out to Tacoma in my bright yellow ragtop VW beetle, classic 1965. The Rockies pretty much killed the engine, so I flew home and told him I’d send him the money to put a new engine in it (not an expensive thing in the '80’s). His car died so he traded my car and his for something drivable. I never saw a dime out of that one. Family…what can you do? StG ---
**Author:** ![River\_Hippie](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/river_hippie/32/26_2.png) [@River\_Hippie](https://boards.straightdope.com/u/River_Hippie)\ **Post date:** [December 23, 2019, 12:32am UTC](https://boards.straightdope.com/t/whats-the-most-money-you-lost-in-the-dumbest-way/845030/69 "2019-12-23T00:32:45Z")
> [@DummyGladHands](#): > > Beta & VHS libraries my late husband built That made me think of my music/movie collection. I tossed a ton of old LPs but still have 100 or so. I have hundreds of cassette tapes (pre-recorded and ones I recorded), I have many, many CDs. Lots of movie and music DVDs. Very rarely listen to the CDs or DVDs, no way to listen to LPs and only the most rudimentary means to listen to cassettes (old boom boxes, IF they still work). Also have many, many VHS tapes with no way to watch them. I like to think I got my money’s worth out of them back in the day when I bought them but damn, I spent a lot of money on stuff that’s no use to me now. If I started down the road of hobbies I sunk a ton of money into and have lost interest in… I guess I couldn’t have foreseen losing interest in things I was so passionate about at one time. ---
**Author:** ![River\_Hippie](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/river_hippie/32/26_2.png) [@River\_Hippie](https://boards.straightdope.com/u/River_Hippie)\ **Post date:** [December 23, 2019, 12:41am UTC](https://boards.straightdope.com/t/whats-the-most-money-you-lost-in-the-dumbest-way/845030/70 "2019-12-23T00:41:09Z")
> [@River\_Hippie](#): > > 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. Quoting myself because I should have added why it was so dumb. When the new owners took over they sent a guy from the home office to run our plant. That guy set off my BS alarm right off the bat. I should have trusted my gut feeling about that guy and put the 401k money in an IRA or some other investment program (or Beanie Babies!). :smack: ---
**Author:** ![Eyebrows\_0f\_Doom](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/eyebrows_0f_doom/32/3119_2.png) [@Eyebrows\_0f\_Doom](https://boards.straightdope.com/u/Eyebrows_0f_Doom)\ **Post date:** [December 23, 2019, 1:47am UTC](https://boards.straightdope.com/t/whats-the-most-money-you-lost-in-the-dumbest-way/845030/71 "2019-12-23T01:47:03Z")
> [@Hilarity\_N.Suze](#): > > 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 have no idea what this is referencing. How is a single store with a parking lot a “red flag” for anything? That’s like every big box store. Offering you drinks? Was this a casino? ---
**Author:** ![River\_Hippie](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/river_hippie/32/26_2.png) [@River\_Hippie](https://boards.straightdope.com/u/River_Hippie)\ **Post date:** [December 23, 2019, 2:17am UTC](https://boards.straightdope.com/t/whats-the-most-money-you-lost-in-the-dumbest-way/845030/72 "2019-12-23T02:17:50Z")
> [@Eyebrows\_0f\_Doom](#): > > 😕 I have no idea what this is referencing. How is a single store with a parking lot a “red flag” for anything? That’s like every big box store. Offering you drinks? Was this a casino? I assumed this meant a retail establishment that could only exist on it’s expensive real estate by selling high end, high mark up merchandise and amenities. ---
**Author:** ![kaylasdad99](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/kaylasdad99/32/3398_2.png) [@kaylasdad99](https://boards.straightdope.com/u/kaylasdad99)\ **Post date:** [December 23, 2019, 3:35am UTC](https://boards.straightdope.com/t/whats-the-most-money-you-lost-in-the-dumbest-way/845030/73 "2019-12-23T03:35:46Z")
> [@Sunspace](#): > > 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. Be funny if it turns out to be _Rigardu\_kaj\_vi\_ekvidos_… ---
**Author:** ![mandala](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/mandala/32/95_2.png) [@mandala](https://boards.straightdope.com/u/mandala)\ **Post date:** [December 23, 2019, 10:39pm UTC](https://boards.straightdope.com/t/whats-the-most-money-you-lost-in-the-dumbest-way/845030/74 "2019-12-23T22:39:27Z")
A decade ago, I lost tons of money day-trading in the Indian stock market - I would estimate about $20,000. After a day of crushing losses, I would bravely venture in again the next day. I was astoundingly, ridiculously dumb. And greedy - one windfall profit and I would erase all my losses. Finally I weaned myself off the damn stock market. Now I am somewhat saner, and have pinned my hopes on Powerball. 😃 ---
**Author:** ![Renee](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/renee/32/287_2.png) [@Renee](https://boards.straightdope.com/u/Renee)\ **Post date:** [December 24, 2019, 2:55am UTC](https://boards.straightdope.com/t/whats-the-most-money-you-lost-in-the-dumbest-way/845030/75 "2019-12-24T02:55:54Z")
> [@Eyebrows\_0f\_Doom](#): > > 😕 I have no idea what this is referencing. How is a single store with a parking lot a “red flag” for anything? That’s like every big box store. Offering you drinks? Was this a casino? Yeah, this one went completely over my head. Other than various bad investments, which happen sometimes, the one that comes to mind is this: I had put $100 bill in the ID holder of my cell phone case for emergencies. Threw the case away when I got a new one, completely forgetting about that bill. ---
**Author:** ![Treppenwitz](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/treppenwitz/32/3445_2.png) [@Treppenwitz](https://boards.straightdope.com/u/Treppenwitz)\ **Post date:** [December 24, 2019, 9:39am UTC](https://boards.straightdope.com/t/whats-the-most-money-you-lost-in-the-dumbest-way/845030/76 "2019-12-24T09:39:52Z")
Well, if we’re allowing stocks and shares, I can tell you the story of an eye-watering “loss”, though it wasn’t particularly dumb (unless you allow for 20-20 hindsight). Back in the last century I was working for a small US company which was in the habit of giving out stock options as bonus. When the company got taken over we all had to either sell the options (that is to say, buy them at the issue price and simultaneously sell them at the currently traded price) or buy out the stock. Everyone sold the options, and we all made a tidy sum of cash. Scroll forward to a couple of years ago - the value of the stock had risen approx 30-fold. Had I bought the stock and sold in, say, 2017, I would have cleared - _cleared_, mind you - over $1M. Well, they do say it’s never wrong to take a profit. Eh? j ---
**Author:** ![phantom\_lamb](https://avatars.discourse-cdn.com/v4/letter/p/5f9b8f/32.png) [@phantom\_lamb](https://boards.straightdope.com/u/phantom_lamb)\ **Post date:** [December 24, 2019, 1:03pm UTC](https://boards.straightdope.com/t/whats-the-most-money-you-lost-in-the-dumbest-way/845030/77 "2019-12-24T13:03:31Z")
> [@Eyebrows\_0f\_Doom](#): > > 😕 I have no idea what this is referencing. How is a single store with a parking lot a “red flag” for anything? That’s like every big box store. Offering you drinks? Was this a casino? I didn’t quite get it either but figured since everyone else seemed to, that I’m just the dumb/naive one here 😃 ---
**Author:** ![DesertDog](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/desertdog/32/11503_2.png) [@DesertDog](https://boards.straightdope.com/u/DesertDog)\ **Post date:** [December 24, 2019, 1:28pm UTC](https://boards.straightdope.com/t/whats-the-most-money-you-lost-in-the-dumbest-way/845030/78 "2019-12-24T13:28:01Z")
> [@Treppenwitz](#): > > Had I bought the stock and sold in, say, 2017, I would have cleared - _cleared_, mind you - over $1M. I can feel your regret but at least you made a profit. Unfortunately I never had the chance. I hired into an internet-heavy company and one of the perqs was a stock option, 100 shares. Unfortunately I’d been hired just as the dot com bubble burst and the option’s price was set at the average price for the previous quarter, about $138 a share. The stock was selling at the time for around $60 a share and in the four years I worked there, continued its downward slide to wind up bouncing around a buck and a quarter a share. Needless to say, I never pulled the trigger on that option. Luckily, it was neither the main reason I’d hired on with them nor the reason I left but it was the only option I’d had in my career. ---
**Author:** ![Zyada](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/zyada/32/3028_2.png) [@Zyada](https://boards.straightdope.com/u/Zyada)\ **Post date:** [December 24, 2019, 8:30pm UTC](https://boards.straightdope.com/t/whats-the-most-money-you-lost-in-the-dumbest-way/845030/79 "2019-12-24T20:30:31Z")
> [@Eyebrows\_0f\_Doom](#): > > 😕 I have no idea what this is referencing. How is a single store with a parking lot a “red flag” for anything? That’s like every big box store. Offering you drinks? Was this a casino? You’re looking at the suburbs. I assumed this store was in a densely populated/densely built up area like New York or San Francisco, where real estate is extremely expensive. ---
**Author:** ![Shodan](https://avatars.discourse-cdn.com/v4/letter/s/9f8e36/32.png) [@Shodan](https://boards.straightdope.com/u/Shodan)\ **Post date:** [December 25, 2019, 6:06pm UTC](https://boards.straightdope.com/t/whats-the-most-money-you-lost-in-the-dumbest-way/845030/80 "2019-12-25T18:06:26Z")
Our company kept getting sold during the days of Y2K. Eventually we were bought by a large consulting firm. A couple of months later, the former president of our firm left suddenly. I had lunch with him a couple of weeks later to find out what happened. He only told me, “get everything they say to you in writing”. I didn’t listen. Cost me about $1250 when I refused to do something that verged on, if was not outright, fraud (charging the client for work I was doing for a different client). So they just refused to pay me for that work. I talked to a lawyer, who said I might win but would probably not collect anything. Fortunately or otherwise, it was not long before they tried to rip off the client in similar ways and it did not work out well for them. Regards, Shodan [Previous page](https://boards.straightdope.com/t/whats-the-most-money-you-lost-in-the-dumbest-way/845030.md?page=3) [Next page](https://boards.straightdope.com/t/whats-the-most-money-you-lost-in-the-dumbest-way/845030.md?page=5)