So I would love to share some stories I have read on Quora about people whom have gone from been wealthy to been poor.

I can tell the experience of a friend. who married a woman who was multi-millionaire since birth. Saying that they were rich is an understatement. They only flew first or business class, he got a new Porsche or Mercedes every single year and they always lived in the best areas in Manhattan,
I remember when he and his wife moved to New York they hired an interior designer from Milan to do the decoration. They spent around a million dollars only with the renovation and furniture for the apartment.
They had it all, and not even in my dreams I would imagine that one day they would lose it all.
However, like many other stories, they didn't lose it overnight, but little by little.
I never imagined they would lose all their money because apart of being filthy rich, they were really lucky.
My friend's wife grew up being a millionaire. Annual trips to Aspen with her family, then summer in Europe and everything we imagine rich people do. I was lucky to enjoy some of these perks when I was invited to one of their vacation homes.
They had a lot of money but they didn't work. After all, they never needed to do it. She received a monthly allowance from her family that I believe was around 700K to 1M per year so they would probably not bother to work 9 to 6 to make $100K more.
They lived this life for around 10 years. Then, they had some disagreement with their family and they stopped receiving the allowance. They lived by their savings for around 3 years. During those years they lived a very good life, but not so lavish as before. After 3 years, when they were about to start selling everything so they could have some money, her uncle died. He didn't have any kids so she received a good sum of money that was sufficient for around 3 more years.
When their bank accounts were about to run dry again her mother passed away and she inherited, along with her brothers, around 4M each.
For most people, it would be sufficient for a lifetime, but they made very bad investments along with some poor decisions and I don't know how, but they ended up losing everything in around 3 more years.
After losing all their money they started living with the money of a trust her parents left to her, Something around 5K per month. But they are on their 50s, they never worked and have no professional skills and they have to pay rent (as they don't have a home), pay all their bills and above all, health insurance with that amount.
I saw them around 6 months ago and they were miserable. My friend developed a neurological disease due to the stress he endured in the last years. His wife was making all decisions as he wasn't able to do it anymore. Unfortunately, he is so sick that he couldn't work even if he wanted to.
I was really sad it happened to them because they were really nice people, It's easy to judge them for never bothered to have a job or be wiser with their money, however, she was born in a different universe for most of us. What we see as a lavish lifestyle she sees as a regular day since birth.
I asked them if they needed anything and obviously what they need is their old lifestyle back. They moved to a modest apartment in a different state.
She told me that the biggest issue is that they don't know how to live like that. She can't imagine what's like to do their own grocery shopping, and worst than that, go to Walmart with a shopping list. She said that if she spent a little more on things she like she might not have money for the supermarket next week.
I would not dare to say that this experience was humbling to them because they were always nice people, the difference is that they were nice people with lots of money. The only positive thing I believe this experience brought to them is that they are no longer superficial. They used to see everything like poverty, sorrow, and problems from a different perspective, and I used to see them through a mask that looked like they were using all the time
Now, for the first time, I was able to see who they really are. What are their emotions, their fears, their desires, and their regrets… For the first time in their lives they desire things, they no longer pull their credit card and immediately satisfy their desires and in that sense, they look like real people for me.
Every time I visited them over the years I always invited them for lunch, breakfast or coffee and even though I'm not wealthy I always offered to pay, and 6 months ago, when I saw them for the last time, I invited them to have a coffee at Starbucks and that was the first time in more than 15 years that they said thank you after I offered to pay for our breakfast.
It felt different. They don't need to thank me for anything because during their life, just by inviting me to stay with them, they offered me much more than anything I've ever offered to them, but for the first time in their lives, they are learning to value every small good thing that life gives to them.
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UPDATE
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Thank you all for the upvotes and feedbacks to this story. In fact, I had two stories about the theme but Quora doesn't allow to publish two answers for the same question, so, for those who are interested I'll post the second story here.
In 2007 I was hired by a medium size tech company. The company had around 150 employees and they were growing fast. When I was hired they told me they would be moving to better offices in two months and they really did it. The new office was really impressive. Huge, very modern to the point it made the cover of a magazine.
My boss and her husband were the owners of the company. They were simply amazing. She was sweet, very polite and it was a pleasure to work for them. They were also very rich. In fact, she was so down to earth that it took me two months to realize that she was one of the owners of the company. It happened one day that we had a meeting with a client and she told me if I was OK to be squeezed on the back seat of her car, as another person was coming with us. I Imagined that she had one of those very small cars, but she showed up on a brand new convertible Porsche .
Little by little, we became acquainted. They invited me to have dinner one night and I was impressed by how rich they really were, They lived on a mansion, the land was so big that they had a tennis court, swimming pool and a stable with 5 horses on their land. He also was a motor enthusiast and had 9 cars. They owned a farm and a beach house in another city, even though we lived in one of the most beautiful beach cities in the world.
They made money fast because I was hired in 2007 and the company was founded in 2002 and it looked like they had a good lifestyle for some years.
They were amazing people, very humble, very calm and you would never say they had so much money just by talking to them.
I left the company by the end of 2007 because I received an offer to work in another place. I talked to them before accepting the offer, I explained my reasons and they were really supportive and told me that if I changed my mind the doors would be open.
By the end of 2008, a former colleague contacted me asking for a reference as he was leaving the company. I asked why he was leaving the company and the told me that the company had gone into receivership. Basically, they were impacted by the GFC.
They were so rich that I imagined that although the company had bankrupted they probably had a lot of savings.
I never heard from them again until 2017.
I had a health issue and I needed to see a specialist. When I got to the doctor, I was talking to the receptionist when I saw a sign with her name over her desk. (Let's say Jennifer Parker - I'll omit her real name). So I said to her. Hey Jennifer, what a coincidence, I had a boss with exactly the same name.
Then she told me that she was not Jennifer, that Jennifer was the other receptionist, that she worked Monday and Tuesday and Jenniffer Wednesday to Friday. I saw the doctor and two weeks later I came back for my return and when I arrived who I see working as a receptionist there? My former boss.
When she saw me she recognized me and told me that the other receptionist told what happened and when she saw my name she connected the dots.
She told me what happened to the company, basically was a problem with the contracts they made and as they weren't able to get a new loan from the bank they could no longer keep the company and pay their debts. With that, they lost everything, not only the company but literally everything.
Their kids moved from private to public schools, they had all their cars, properties and assets confiscated and ended moving to a small apartment near the city. Her husband was able to get a new job (at nearly 60 years of age) and she had to go back to work to complement their income.
It was a huge surprise for me because you always expect that these things will happen to bad people, but never to nice people like them. They were honest, decent, hardworking, family oriented, and everybody in the office liked them.
Coincidentally I bumped into them again 3 months later in the mall. What surprised me the most is that they were able to go from a very rich to a very modest lifestyle without changing who they were. We sit together to have lunch in the food court and they were living like that was the life they always had. They were exactly the same people I met 10 years before, they were happy, making jokes with their kids (that were teenagers by then) and even when she told me what happened she didn't do it with sadness.
I don't know how they managed everything so well. Going through an experience like that could be very damaging, but it looks like they had a way to cope with everything.
It taught me a lesson that money can't be trusted, life can be full of unexpected events with many things out of our control.