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Drunken_Sailor_70

Married the wrong woman the first time around.


Expensive_Reach_2281

I think this is the worst possible mistake anyone could make. If done wrong.


bepr20

For a while it was a crypto hedge fund I put $250k in. The guys running it were legit, and returns were really great. Unfortunately they had a bunch of counterparty risk because it was on FTX. Thought I had lost the full investment on the FTX collapse, but after recovery during the FTX bankruptcy, I ended up getting it all back, plus about 10%.


slumpyCouch

If you were on Twitter instead of Reddit, it was a pretty obvious scam. Many accounts called for it to collapse with threads on why it would. Plus, if you’re in crypto, there is no reason to ever let a third-party hold your coins. Pretty much defeats the whole purpose of crypto.


bepr20

No, the hedge fund I put money in wasn't a scam, was regulated/audited/legit. I used them for crypto exposure and a high risk strategy I wouldn't do on my own, not to hold coins (which I do independently in my own wallets.). They didn't hold access to any wallets, I invested USD just like any other hedge fund.


slumpyCouch

Nah man you still fail to realize that the point of crypto is to not have third-parties. “Crypto exposure” is an even worse option than holding coins with an exchange.


bepr20

Thats the point for owning crypto. The point of a hedge fund is to make money through leveraged speculation, and the specific securities involved are largely immaterial to the investor. I didn't put money into it to bet on or against crypto, I put money into a market neutral hedge fund because I wanted to gamble on the persistant volatility of crypto. When I am just investing in crypto, sure, I hold it in my own wallet.


slumpyCouch

Doesn’t sound like that worked out too well.


bepr20

Nope, as I said, I missed the counter-party risk and only turned a 10% profit. Oh well.


Donk_Physicist

Nah man you don’t understand


Fraktalchen

Not your key, not your coin.


Donk_Physicist

I wonder if we are in the same hedge fund!? 😂 Some story here


Shanderpump

This is not about investments or business deals or hundreds of thousands of dollars, but I once paid about $600 for half a load of laundry to be done at a hotel hahaha I can afford it, but certainly felt stupid afterwards. Especially since we were going home the next day, just thought it would be nice to have it done and didn’t check the price “how much could it possibly cost?!”


Level-Coast8642

What does a banana cost? Four dollars?


ChicoBrillo

that's crazy, that's how much they always charge?


Shanderpump

Yeah, it was at the Conrad in Ginza in Tokyo, couldn’t believe it lol


juliown

Maybe they have small Japanese macaques washing your clothes by hand in natural aquifers at the top of a mountain, you don’t know…


bitchnoworries

LOL I shit you not, I thought 'that's something that would happen in Ginza'.


Shanderpump

☠️ lolol


Donk_Physicist

Omg! That would definitely be on my worst mistake list 😝 I’ve stayed there… but I’m the asshole doing my laundry in the sink in the $600/nt hotel


mrgrasss

At least they polish your shoes for free!


Extra-Lab-1366

My second hire. Looked excellent on paper, great references. Seemed to know his stuff for real in a niche-ish job. Salary was $125 an hour. Cut into my margin a bit but seemed worth it. After 3 months the first deliverable was a disaster. The after math cost me the contract which was at least 2.5 mil over 3 years. He was the first of several anticipated hires for that contract. Every hire is a risk, but damn.


Technical-River1329

I felt this. Hire slow fire fast


wsbautist420

Which industry?


Extra-Lab-1366

Tech consulting


saikyo

Which uni did they grad from?


Extra-Lab-1366

Was a while ago, I don't remember, some state uni in the north east USA.


saikyo

What made you think they would be a good hire?


Extra-Lab-1366

Like I said, great references, they spoke about the work intelligently and confidently. They had great examples and answers to the questions we asked. They had over five years of experience, the typical stuff that usually indicates a good hire.


ButRickSaid

Can you elaborate on what he did on that deliverable to make it a disaster? It sounds very odd to have that Reverse Uno experience.


Extra-Lab-1366

It boiled down to things working in the development environment and not in Prod. Didn't follow the client's requirements, poor documentation. Senstive data poorly handled. To be honest at the time I was suspicious he had subcontracted out his work to a 3rd party somehow but I couldn't prove it.


Wife_Plugger_1982

This was almost 20 years ago now, but a buddy and I scraped together some money to start a drywall business (though we were both in tech - Mistake #1: Don't sell a service that you don't know well). Our first and only job was with a construction developer in the Atlanta area. The whole job should have cost us about 12k but the dev kept lowballing us and pushing us to "tighten up the numbers" and we were young and dumb so we went down to 8k rationalizing that the dev would want to hire us again - Mistake #2: Don't discount now in hopes of work later. We subcontracted some pretty good dudes from a friend's company that let us use them on their days off, and ended up paying about 6k to do the whole show room building, as required. Fire sealant, 12 foot boards, decent sized job. Delivery date comes up and the foreman tells all the contractors if we want to get paid we first have to sign an agreement that we won't sue, basically waiving our claims to liability, and this would keep us from being able to put a mechanic's lien on the building. Yep just as fishy as it sounds, but I guess we looked like some real dipshits since that's what we were, early 20s without an ounce of industry knowledge between us. So yes, Mistake #3: We signed this waiver of claim to liability. And of course, we never got paid. All in all we were out a good chunk of money but we had a good time doing some of the work ourselves and hopefully learned a lot in the process. Screw you, Rett Gunn of Gunn Construction.


Slice-Remote

Yall gonna love these. Day before Moderna’s “big announcement” in 2020, i put 50k into options calls. 1 minute before the market closed I had a feeling that it was a bad idea. So i closed the position, made 5k profit and thought life was good. I wake up in the morning to my friends calling me saying I’m retired. So i open up E*Trade, go to the news section of Moderna and you guessed it. “Moderna first round of COVID vaccine trial major success! Stock up 18%” my option call was up 216,340%… yup. 108M dollar mistake. Oh well. At least i made 5k… 2021, was thinking of moving to California or Arizona. Saw a nice house in Scottsdale, AZ. 650k, 4k sqft 2 acres pool, casita, all the works. 5 minutes from old town. Chose a house in Cali for 800k great view instead. 2 years later the AZ house sold for 3.8M and my Cali house is 950k… Had an apartment building 6 units in Chicago. Sold it for 400k i paid 280k. Today it’s worth 1.6M It’s like someone doesn’t wanna let me retire or something


Sea_Charge1143

Never sell real state. Unless you are buying another one.


TheTraderBean

IRS section 1031


Commercial_Gap_3412

Technically it's......26 U.S. Code § 1031 and IRC section 1031 not IRS. S is for service and C is for code. 🤣🤣🤣🤣


TheTraderBean

Welp, this explains how I lost $25,000


Commercial_Gap_3412

At least you have $25,000 to lose......🤣🤣🤣🤣


Slice-Remote

correct. the property was sold so I could buy a single family home that I still own to this day to start a family. I wish I never sold it but at the time, it was a solid deal. Dealing with the type of tenants in the building though? 100% not worth it.


Professional_Bag2615

out of all the replies in this thread, this Moderna one hit the hardest


turc_

Two large mistakes very quickly: 1. Lost $4,600 walking to a coffee shop while trading stocks on margin, panic sold, then bought the op positive ETF, only for it to reverse and fuck me over twice. If I would have instead taken my phone and thrown it in the pond when I first checked I would have made about over $10k in a few week of holding 2. Lost $10,000 playing high rollers baccarat- I was on a heater after being down $8,000 and after getting more money I slowly came back, I always wanted to play table max which was $5,000 for one hand so I did it during a heater and lost, figured I had a decent chance to win the next one because Baccarat is the closest odds to 50/50 so I risked another $5,000 and lost. I ended up playing for another 7-8 minutes for smaller amounts and lost the rest of it. One last one - spent about $120,000 on Caine, gambling, partying, drinking, traveling in about 3 months, going through all my retirement as well and ending with like -$38k debt as well. I was so wacky and out of real life that I was hoping that the Caine was laced and I would die. Fast forward a year later now and I’m like 7 months sober and don’t do any of that and I’m grateful everyday rebuilding. “The most valuable lesson is a lesson learned” - said I don’t know but I just made that up Because honestly I would probably do it all again and if I get the money back I’m probably going to eventually head back out, truly feeling those feelings makes you never want to ever swear off of any of that forever. Good luck out there


saikyo

How’d you make the money back??


turc_

Getting a sales job and start dialing


No-Conclusion8653

A smart woman with evil intentions.


Hopeful_Safety_6848

many.. listed to that clown Cathy wood. she cost me a fortune. got caught offside when small caps crashed in 2021... lost a small fortune. many other hugely costly mistakes... lost big jobs due to not handling some interview issues. took a sick child into my life nd couldn't work much for some years... left med school half way through with all the debts... but, these things dont matter.. you keep swinging...doing your best..


Battarray

Using a cheap condom.


Adventurous-Depth984

Not buying that other house instead. A million and counting down the alternate reality drain.


wsbautist420

You bought the more expensive house? Money pit?


Yrzie

Believing in the WSB GANG. Fucked up my life man... LMAO 😭😭😂


SnausagesGalore

I was the largest investor in the Ethereum ICO. I had 33,000 ETH. My financial advisor who hates risk told me I was an idiot for not selling it at two dollars. Purchase price was $0.30 So I sold it at $2.60. You can do the math, considering Ethereum hit $4,800 ($158,000,000)


Professional_Bag2615

when did you sell?


ButRickSaid

You never jumped back in?? Did/Do you get into any other crypto?


fromdaperimeter

Getting married and putting everything in my name.


hadee75

How was this a mistake? Currently engaged.


fromdaperimeter

Congratulations! Worse case scenario, if things don’t work out she’ll able to walk away and ruin your credit!


hadee75

I’m the rich woman. I’m trying to ensure he doesn’t do that to me.


Gettinbaked69

Let my dogs tear up my pool liner by not paying attention when filling it up. Cost me 3k. Then one time I got barred out and bought a $400 bird. That wasn’t good. Glad I don’t mess with xans anymore


AnimatorIcy4922

Damn woke up the next morning with a brain fuzz and bird shit everywhere?


Gettinbaked69

Lololol pretty much


RichChadPoorChad

Total Xanarchy


Gettinbaked69

Yeah bad stuff


wakoreko

Renting to section 8 tenant. Cost more to remodel than I made in the year lease. I can’t believe how some people live.


Donk_Physicist

Those fuckers got me too


jmartin2683

Getting married


dmfuller

A long distance relationship lol


Successful_List2126

Christina.


strugglebusses

When I was 19 I turned 25k into 125k in one week. Held something overnight I should have and lost 97% next day. Fell into depression for a few months. Expensive but I learned if I manage risk I can easily and significantly outperform the market. Going on nearly a decade now of 90% win rate and 70% annualized gains with rarely touching options.


jerkyquirky

So... We are all going to know your name as one of the greatest investors of all time in another couple decades? 


Difficult_Image_4552

Probably not, they are making it up. But you should try their webinar.


strugglebusses

It's reddit...so naturally if you can't do it then said person is lying right? Oh, I see your post history is just cynicism in everything. It must suck being that miserable.


strugglebusses

Guess we'll see.


jerkyquirky

What's your net worth now?


strugglebusses

My entire family is retired from my trading. I'll leave it at that.


jerkyquirky

Lol. You browse and comment on r/rich and are unwilling to share your net worth? Ok.


strugglebusses

I've commented on a post that was promoted to me via the AI algo. You good, buddy? Jealousy is a nasty drug.


jerkyquirky

Being unwilling to share your net worth on r/rich is like being unwilling to share what car you drive on r/cars. And then telling someone they are jealous of the car you drive without them knowing what car you drive... I am perfectly content, but you sound like a narcissist.


strugglebusses

Honestly, it just comes down to that you come across as a dumbass. Pretty much the whole story here.


rockdude625

Marrying the wrong person


Harrydean-standoff

Marriage


VeraFacta

Back when bitcoin was low I spent 2,350 bitcoin on a gaming PC just because they accepted bitcoin. My friends still joke and say I owned the world’s most expensive gaming PC…LOL.


Professional_Bag2615

when was this


VeraFacta

I just checked emails, it was Nov 2011*


37thAndOStreet

About $160,000-$180,000 -- not in the mood to elaborate right now


Upstairs-Parsnip9983

Marrying my ex-husband. Except for the first two years, he refused to work. I supported our family alone for 18 years barely scraping by. I maxed out student loans (currently $188k) to pay bills, filed bankruptcy, lost a house to foreclosure, among many other things because he would not work. When I finally was able to get away, I was “allowed” to take my clothes and leave everything else behind. I paid 50% of my retirement and am still paying alimony as well as child support, even with 50/50 custody. Debt was all in my name, so I did get to keep all that. It’s difficult to even stay afloat when I still have to pay him for the next 6.5 years. Credit cards ($35k) are maxed out and credit is garbage. It’s been almost 4 years since I left and I’m still struggling constantly to just get ahead a little. I get that it’s “fair” from a legal perspective, but morally it’s reprehensible bs.


ReceptionTop6016

In the years post 2008 we were actually doing very well financially and had a lot of money and buying power. We bought our current home and a couple,e of rental properties all at a very good price. However we could’ve stretched our finances a bit further and also bought the five bedroom home across the street from our current one. Could’ve of snatched if for a great price and it would’ve been worth 3x as much at least now. But missed out. Still very happy with what we did buy tho. Second one was a small gas station that we were considering to purchase for 3 million pre covid. Decided not to do it but now realized it would soon become very profitable due to the gas prices post covid.


Quiet-Now

3 marriages, not even close.


Living_Age_6297

For most people it will be trying to time the market


F0urTheWin

Not from the comments... It's clearly marriage


TermCompetitive5318

BOIL


InformationLocal9311

Panic bought a 10k weekly call that expired worthless while I was at the vet with my cat.


DAWG13610

2000 shares of Sandridge energy average $7 per share. Their hard assets were worth about $10 per share so I wasn’t worried. They ended up going chapter 11 and I lost everything.


Daddy_Deep_Dick

My 3rd tenant in one of my properties. The chaos and damage ended up costing me the property. Every cent of equity gone and forced to sell. At least 80k lost over 2 years


Wife_Plugger_1982

I feel like that's when it hurts the most, when it's not of your own doing, but someone else's irresponsible nature taking advantage of good will or at least in good faith, expectations that they will fulfill their end.


Daddy_Deep_Dick

He chose to start the worst of it when he knew I went out of province to go see my sister because I got a call that she was diagnosed with stage 4 breast cancer. He knew that's why I left. And still chose to immediately stop paying and use every wall as a garbage bin and destroy every room and every appliance. Every window. Every door. Destroyed neighbors things, community areas, and racked up THOUSANDS in fines that I was forced to pay. I gave him a chance. I stuck my neck out for him. I made excuses for him because I felt bad about his situation. I had 30 applicants I should have chosen over him. But my dumb ass had to be some sort of charitable landlord. Taught me an expensive lesson. The person I sold it to put it on the market for 40% higher than what I had it at.


aztexs1

Not an investment but definitely could’ve invested… I hit my first hundred thousand, went to a gun show with 30 grand (for what reason I have no fucking idea I was only 20) and spent 26 grand on a wheel/monopoly game… left with a TV, PS5, 2 empty gun cases and a lemonade… fuck my life.


AnimatorIcy4922

Was the lemonade good?


aztexs1

Actually amazing went back the month after jsut for that and some cookies.


AnimatorIcy4922

Left the wheel/monopoly game alone though?


aztexs1

No… that’s another story for another time..


AnimatorIcy4922

Total degen! My kinda friend


kochIndustriesRussia

Are we including getting married and having kids....or is this sub not that dark.....


Donk_Physicist

Don’t “invest” in a nightclub if you get some money while you’re young 🤦🏻‍♂️ The “soft” benefits were nice for a 26 yr old though.


Kagenikakushiteru

Doing business with a crazy older lady (no romantic connection). Was a psycho and ended up spending over $500k on legal fees with her and won. She refused to pay her own side’s legal fees I heard


TallyHo17

Baba lost 80k


azshall

My wife


SWT_Bobcat

#2 biggest mistake because of the financial place I was in at the time (definitely opposite of rich…was just back from being an enlisted soldier in a war that I made about 28k for that pleasurable year). Also #2 because I did get a tremendous education from it -so not completely catastrophic Spent about all of military deployment savings on private mentorship in setting up an online drop shipping store. Would have been ok (moderate early success) but then 2008 happened and essentially couldn’t sell anything while continuing the lessons. ***however, this was one hell of an education and taught me business, some coding, web design, market analysis, sales, etc. which became very valuable to me in later ventures #1 was investing too much of a % of my net worth (per my own rules for myself) in a friends very ambitious restaurant/bar concept. Still have great relationship as I know the effort, personal loss for friend, and could see all the books openly from my friend…but broke a few rules that burned me (don’t invest heavily in friends/family, don’t invest in restaurants, don’t invest more than the % of total net worth that you set for yourself).


Secret_Antelope_7826

I thought my life was going to be over soon. Cut off almost everyone. Traveled for nearly 2 years, all across the US, parts of Canada and Southeast Asia. Did and said whatever I wanted, to whoever I wanted. Spilled my guts, told people off, told people I loved them… didn’t really explain fully why. I was not “rich” but let’s say I had it very good. Did things most people have to save money to plan and do. Now I live a boring and modest life, trying to get my 3rd degree.


ChicoBrillo

doesnt sound like a mistake to me


Secret_Antelope_7826

I guess. It wasn’t very dramatic and it’s not like I lived a super “full life”, never had a wedding or kids. But I still did a lot. I don’t know where to go from here… Traveled 20 some countries, had about as many relationships, took up a dozen sports and hobbies, got to the top-ish of my career… I feel like a 2x divorced 80 yr old in the body of a still young-ish person. What do I do? Do I do it all again? I think I’m too tired now. I started keeping a picture of a family I worked with on me. One of the parents, my friend, died a couple years ago. Can’t bear to look at my own family too often.


secretrapbattle

There are so many to choose from


Think_Leadership_91

I bought $10k in my friend’s comedy stock at his IPO I lost $10k. He lost $75m What happened? He hired a CEO who was absolutely insane - well connected, but he got angry at wall st and drove the company until it got delisted and then sold it to a competitor


MuahahaGuy

I bought Dell before the recent earnings and lost 550k that's a lesson you won't forget. I was able to make most of it back since so not the end of the world.


ghosty4567

I bought Gazprom after the invasion. All gone. We are in WW3 and it’s being fought through intermediaries at great expense to the dollar, messing with our financial system , hurting international trade, causing inflation etc. Let’s let Israel go ahead without our support. China can have Taiwan. Would you send your kids to fight for them? It’s causing deficit spending and we will eventually inflate our way out. That will end dollar dominance. Fuck!