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16 people share their family's 'we could've been rich' story.

16 people share their family's 'we could've been rich' story.


We all have that one uncle who loves to tell the story about how the potential family fortune was squandered by a bad stock choice, unfortunate timing, or an unlucky gambling session...

'We would all be living in a golden castle right now if your great grandfather hadn't sold his house on the beach in 1910.' So, when a Reddit user asked, 'What's your family's 'we could have been rich' story?' people were ready to share the 'so close but so far' financial tale that still haunts their family.


My grandfather helped with construction on Disney World. He was offered either stock or a lump sum. They didn't particularly need the money, but my grandmother wanted to order something expensive out of a catalog, so they took the cash.

Thanks, Grandma. I don't know which of the hundreds of useless, never-used knick-knacks it was, but I'm sure it was well worth the millions your stock would have been worth today. - CmplmntryHamSandwich


When I was in college I was working for UPS BEFORE they went public so back in like 96-00 anyway I had worked there long enough that I was eligible for buying stock before it was offered publicly and at a huge discount.

My parents and I talked and agree they would lend me 75K to buy as much stock as I could get with that amount, then after it went public pay them back the money with a 'tip' and the rest would be mine for school, home car whatever.

Well, they drug their feet on it and I missed the boat. There were employees that made so much money they quit on the spot the day it went public. I have never done the calculations but I am sure I missed out on at least 400-500k. - maschine01


My grandfather was a cattle broker, commodities trader and businessman living in Wichita, KS in the 1950s and 60s. He was offered a significant share in Pizza Hut by its founders at the outset of the venture. Unfortunately, he did not think that pizza would ever take off as a fast food option, so he declined.

As it turns out, people really like pizza. My grandfather did actually manage to get quite rich from cattle and commodities, but he could have done much better as founding investor in Pizza Hut. - Kittens-McTavish


When my grandparents died, they were going to divide their assets equally between the grandchildren. There are 8 of us. My uncle didn't like that my mother owned 4 of the grandchildren, and he only had one. So he let the government take it. The amount? 8 million. I missed out on a personal million dollars. My uncle is a d*ck. - toreadorable


My family immigrated to the US during the potato famine in Scotland, hoping for a better life. Well, skip a few generations and my great great grandfather gets a letter from Scotland. He inherited a castle and LARGE estate after someone died. However, no one in my family was able to afford a boat back to Scotland to claim it.

I guess it went to the government? I don't know. My great Uncle still has a copy of said letter. I assume it gives the details and one day, when I can afford to go visit and see Scotland, I'm going to go get the letter from my great uncle and see if I can't track down the castle my family would have inherited. It's my dream. - WifeyP


My now deceased Grandfather had an opportunity many years ago where he could have invested in a new burger chain which is known today as McDonalds.
I'm sure he knocked himself over the head a few times for not doing it but tis life! - Trevo91


My mother always says that my Great grandmother had the best pasta sauce. Well apparently my great grandmother's cousin stole the recipe and started a restaurant. And was never heard from again. My mother is convinced that the recipe is used by Ragú. - Raph_E


My late great-aunt won the 'Win $1 million every year of your life' contest from Publisher Clearing House about a year after she had passed, we found the letter in her mailbox before the house was sold. The promotion said that, had she been alive, she could have given the award to a member of her family. - [deleted]


I heard stories a while back my family owned a significant portion of Long Island, NY. My family was wealthy around 1500s or so. Their wealth began to drain so they moved here in the 1600s. We owned several farms, a couple mansions, a homestead, 1/3rd of the Tuder patent. I know of 2 family cemeteries on Long Island. Sold a well known island to NYC in the early 1900s I think it was.

Today I sit broke working 2 jobs hoping for my big break to come. No significant pieces of property remain in the family that I know of. If only there was a developer or architect in the family. This isn't just lucky break in stocks money rich, this is like significant Vanderbilt type rich and power that was missed. - Annihilating_Tomato


My dad was at a pub in Toronto on Halloween 1997. He was drinking when this guy came up to him dressed up like Austin Powers and started talking to him- he bought a couple rounds. My dad was joking around with him and doing impressions. The guy says he's Mike Meyers.

My dad says 'F*ck off, you're not Mike f*cking Meyers.' Cue my dad arguing with this guy about who he is, and joking with him some more. The guy starts telling my dad he's hilarious and that he can help him out with a comedy career if he wants- he was really adamant about wanting to work with him. My dad just says 'Yeah sure buddy, like I believe that.' They parted on amicable terms and my dad stumbled home.

The next day he goes back to that pub for dinner with a friend and the bartender says to him, 'Hey, you're that guy who was talking to Mike last night. Isn't he awesome?' Finally my dad realized that it was the real Austin f*cking Powers he was drinking with. He left that bar and never returned. F*cking christ dad, you could've been a f*cking comedy star. All that money because he's terrible with recognition. - BitchMagnets


I remember holding out on buying some bitcoins because the price had just jumped from ~$2 to ~$4. I thought, f*ck that, I'll wait 'til it comes back down. It never did. - mystache_


My Dad owned IBM stock(~500 shares) back in the 70's, he sold it when he doubled his money. - PlaneFxr


My dad prematurely selling his Apple shares - [deleted]


My great grandfather owned a small soda company in NYC. Coca-Cola offered to incorporate it into their business. He said no because he wanted to keep it a family business... - Teddie1056


Parents almost bought a house in London back in the 70s… - [deleted]


When Subway was just starting to become known to the general public my parents were offered to get into the business for a very cheap price. They turned it down because they wanted to take me (was about 6 at the time) to Myrtle Beach instead that summer. Was not worth it. - doubstep

Sources: Reddit
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