25 Devastating ‘We Could Have Been Rich’ Stories

‘In ‘99, my dad was told to invest in Lululemon. He didn’t’
25 Devastating ‘We Could Have Been Rich’ Stories

Imagine finding out that the reason you have to work for a living is because one of your idiot family members didn’t cash in on a potential windfall when they had the chance. Whether it was a disapproving wife (ugh, women, amirite?) or a grandfather who didn’t believe in the future success of Trivial Pursuit (ugh, grandfathers, amirite?), Redditors have disclosed the reasons they’re not rolling in cash right now. And while in a lot of cases, “almost” doesn’t count, it’s hard to read these stories and not feel at least a twinge of empathy for the “what-if” of it all. 

why_renaissance . . 9y Henry Ford wanted my great-grandfather to be his business partner. My great-grandfather said no because he didn't think it would be successful. God DAMNIT. ... 3
 . . 9y My grandfather was a player for the NFL back in the early fifties, before the sport had millions of dollars in it. Не would travel the county playing football and barely getting paid. Had he been born 10 years later we'd be rolling in his football money ... 15
BitchMagnets 9y My dad was at a pub in Toronto on Halloween 1997. Не 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 Fuck off, you're not Mike fucking 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
dnteatyellwsnw 9y This is what happened to my father, albeit before I was born, so had this happened, I probably wouldn't exist today. Instead of money, my father got the richness of me and my brother. My dad used to be a manager for Rent A Center in the 70s. Не was damn good at it too. Не managed a tough store in south Boston, the war zone. Не has tons of crazy stories about being held at gunpoint, having a hit placed on him by someone he fired, etc. But one day he told me this and my jaw
Kittens-McTavish 9y My grandfather was a cattle broker, commodities trader and businessman living in Wichita, KS in the 1950s and 60s. Не 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. ... 20
SlimTim222 . 9y My great grandfather owned a small grocery store in Upstate New York. Не was approached to help another competing grocery store expand and he turned it down to maintain his own. That competing grocery store is now worth billions and has a cult following in most North Eastern states. It starts with a W. ... 188  6 9y Goddamnit do I love Wegmans. ... 193
Bradboy 9y My great grandparents moved to Australia (We live in the UK) and bought a silver mine and land for a banana plantation. One year the banana plantation failed and all the money from the silver mine was put into the next years' crops. Next year the crops failed again and they were broke. The sold the land of the banana plantation to raise funds to get back to the UK where my Granddad grew up. To this day the Silver Mine still technically belongs to us as it was never sold and the family name has stayed the
 . 9y Parents almost bought a house in London back in the 70s... ... 494
wz226 . 9y My great grandfather had a friend who owned a McDonald's right when then we're starting up. Не offered my great grandfather a partnership but he turned it down because 100 dollars was too much to invest for him back in the 40s ... 8
cheeseuh . 9y Back in 99 my dad was told to invest in lululemon but he didn't. Не now regrets that choice. ... 9
yen223 . 9y Relative of mine was once offered an opportunity to invest in a coffee-shop chain, back when they were about to expand into my country. When he saw the prices, he asked Who is going to pay $10 for a cup of coffee?! Turns out a lot of people like Starbucks. ... 1.4k
Teddie1056 . 9y My great grandfather owned a small soda company in NYC. Соса-Соӏа offered to incorporate it into their business. Не said no because he wanted to keep it a family business... ... 460
Nairobicowboy . 9 9y Dad owned shares of the football team Tottenham Hotspur. Sold them in the 90s when he could've kept them for the summer of 2010. ... 10
Natillym . 9y In the 70's a scraggly hippy named Ben asked my Grandpa to invest in his ice cream shop and in return he would get a share of the business. My grandpa laughed in his face and said no. To this day my family refuses to eat Ben&Jerry's ice cream. It's a painful reminder of what could have been.... ... 3
CmplmntryHamSandwich .  9y My grandfather helped with construction on Disney World. Не 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. ... 1.3k
The_Prince1513 . 9y Back in the late 90s early 00s my Dad thought that internet pornography was going to be a huge cash cow, and wanted to quit his job to design what are basically the tube sites of today. My Mom was like we have two kids in elementary school wtf. So he didn't do it. ... 781
lyssinator . 9y I know I'm really late but my uncle Со created shazam, but didn't file the paper work to stick it to his wife. They could have been riiiccchhh. ... 2
maschine01 9y 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
notheebie . 9y My mother inherited about 150 acres from her grandfather down in Lousiana. It was about 10 miles off of the Tuscaloosa Marine Shale. We could have been rolling it :( ... 21
BourbonScotchWhiskey .  9y My great great grandafather loved to collect art. Не had an antique shop in New York in the 20s. Не sold them all before he died unfortunately. All Rembrants. ... 2
epiccheese2.9y My (now deceased) grandfather was approached by the two makers of Trivial Pursuit (before they had made the game) who he worked with, and they asked him for $1000 as an investment. Не said поре! My grandmother then proceeded to tell him that he should have invested, that didn't change his mind. Dammit grandpa. ... 217
Devator22 . 9y My mom knew Mrs. Portillo when they just had a couple hot dog stands. My dad could have invested in their first full restaurant. If you're not from Illinois, look up Portillo's. ... 177
mr--empty . 9y Before Bill Gates was married, his mother and father worked with my mother. Не asked my mother out on a date and she turned him down, because he wanted to go to a football game and she didnt like sports. I was about 10 and my parents had gotten divorced a few years before. I have been sad for over 25 years.... ... 2
doubstep . 9y 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. ... 464
 . 9y two brothers owned a lot of oil land. that is land with oil in it. One of them did not think there was any future in oil and sold his share to the other. guess which one im descended from. here is a hint i have to work for a living. ... 303


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