“I May End Up Homeless”: 71 Former Rich People Share How They Ended Up Broke

My grandfather (mother's side) owned a large ranch. My grandmother became sick with cancer. He spent everything on treatments. Nothing worked. He lost everything trying to save her. They were left broke and heartbroken.

Father blew generational wealth on gambling. Had multiple shoeboxes full of horse racing bet tickets in case he hit big and had to offset taxes. He lost it all and ended up embezzling money to keep shooting for the big win. Mom paid the price. She and I ended up on food stamps and moving in with her mother and sister. I shared a bedroom with my Aunt as a teenage boy. I have a big aversion to gambling and know way too much about needlecraft.

I grew up in poverty and in my twenties hit my stride doing admin work where every time I got poached my salary went up by a significant amount and suddenly I was an *executive assistant* and making the big bucks... at least for me... at least for back then, lol.

But some issues I had with my feet turned out to be just the most visual of a bunch of issues I have with my hips and back and after my last pregnancy my body just kinda fell apart. Suddenly I was struggling to get to the mailbox and had to take breaks to get the dishes done.

An accident, an illness, a complication ... you never know. Your health is not a given. But hey, at least I already knew how to live in poverty!

It was depression. I lost my son and daughter and didn’t care about anything. Screaming every night to nightmares where I tried in desperation to save my children. I let everything go. Stopped managing my life and myself. I was unrecognizable. Banks and creditors took most of what I had. Money was nothing to me. Didn’t care if I had to take the bus everywhere. Took over 20 years to recover. My lost decades.

I had a really good remote job. I was making 6 figures and really took for granted that income and the job market. I could've made a lot of smart choices, but I ended up embracing alcoholism.

Lost the job, got into debt, several years of applying and starting and bailing out of positions. Finally realized how valuable employment is and got my [life] together. Now I've held a good in person job for 2 years and am trying to climb out of debt and gain sobriety. [Things] fall apart slowly, and then all at once.

Laid off, then cancer. 3 years later I can't afford to live on my own.

Not me, but someone I know.

She joined an online investing group, and was convinced to "invest" most of her wealth into an online crypto scheme. When she tried to withdraw her "profits", they demanded additional "fees" and "taxes" to release them. And she sent in those fees, but there was always some other "good faith payment" or "deposit" to pay.

It was the classic "pig butchering" scam.

Now she's practically broke, but thankfully she didn't sell her home. Her relatives, who she had lent money to long ago, are paying her back by paying for her basic living expenses, making sure she doesn't receive too much lest she fall for another scam. So at least she lives OK, but nowhere in the luxury she would have had she not been victimized by these criminals.

I don’t know about wealthy, but I went from making 180k as a software engineer to barely anything now due to battling a chronic illness (long covid). I’m living off my prior investments and hoping I can figure something out before the money runs out.

My parents opened a small business back in the 2000s.

Made close to 200-300k a year.

Then my little sister got sick, medical bills were close to a million by the time she [passed].

Then about 6 months after the 08 crash happened.

For the majority of my childhood my parents worked 60 hrs a week plus, and brought home at best 30k a year.

I was far from rich, but as a single guy with no kids making close to six figures and being relatively responsible with the money, I was doing pretty well. Unfortunately I made the mistake of having some major medical problems in the US. Now I'm being sued by my former creditors, but the joke is on them, there's nothing left to take. I have the paperwork to file for disability next to me right now. I kept putting it off hoping one doctor or another would figure out what is wrong and how to treat it. A bit worried I waited too long and may end up homeless before it goes through.

Not me but my parents. In Vietnam, they went to private schools, had maids and nannies. They had a big house and owned a factory. But the communists took cover and both my mom and my dad’s families fled. They both started off from nothing in America and relied on church donations. They both became engineers, and became extremely frugal. Still are. They have an extremely hard time spending money.

My grandma kept her wealthy mentality. She would still help people and lend them money as if she were a billionaire. She conducted herself with the ultimate grace and always had an abundant mindset. She wasn’t haughty or spoiled at all; her idea of wealth was to help people and never ask for a dime back. She treated everyone well. Even if she wasn’t rich anymore, she was able to lend money because she again was extremely frugal and business minded. She would treat all of her grandchildren well and save all her social security checks to give us cash in red envelopes for our birthdays and holidays. She was the epitome of regal and gracious and selfless. Miss you grandma 💗.

My family was middle class for a very expensive town, which is wealthy by country standards. I got kicked out for being gay so I was effectively homeless in high school and had to work a bunch of jobs to put myself through school. I'm finally in an okayish financial situation in my mid 40s. It's amazing how expensive it is to be poor, and how hard it is to survive, much less build wealth and security. Apparently I also have a ton of genetic disorders and health problems plus mental health stuff, so that makes it even harder to keep a job, plus healthcare is expensive.

I escaped a [toxic] relationship. Had to start over from scratch while 7 months pregnant with 2 toddlers.

Grandma gave away everything to a church.

Oh I have a good one that happened to a family friend. Trust fund kid, never worked a day in his life. Trusted a financial expert to manage his fortune and lived 50 years in luxury off of dividends and distributions. The expert had pretty much everything in a single, very well performing, Chinese stock. Chinese company went POOF. Financial Advisor also went POOF out of the country. This guy went from literally riches to rags. He has rich friends, one of whom let him live in their cabana (a massive pool house; still nicer than most people on earth live), but he had to go to work as an uber driver since his only skill was being able to drive.

Grew up affluent - country club membership, private school, the whole shebang. Then dad got cancer, which ate up a ton of money, and after he [passed away] mom wildly mismanaged what was left. Wound up bouncing from one job to another while I tried to get my [life] together to go back to school. Eventually did okay, but I still live in a [trashy] apartment while the house I grew up in is worth well over a million bucks now.

I was badly bullied and discriminated against at work. I was one of the top women in my field. It was either stay, earn six figures and be humiliated or leave with my head held high and be unemployed. I chose the latter, sold most of my stuff, travelled around Europe and loved it. Then got a job on my terms later.

My dad was the rich one. When my parents separated due to domestic violence, he told me to choose between either him or my mom. I chose my mom. He kicked us out in the streets.

Yeah, my mom got child support but she always had spending habits so... I never saw that money go towards what we needed.

Spouses father sold a shipping company for a million bucks back in the late 80s or early 90s and put it all in Enron.

Not me but a guy i went to school with. His family was stupid rich, his dad [passed away] when he was 21, left him with millions. He [spend] it all in 3/4 years. His mom squandered her share too. He still posts pictures of helicopters on social media asking if he should buy this one or that one. It's a little sad bc everyone knows he is broke and can't even afford a car, nevermind a helicopter.