Ex-Millionaires Share How They Lost Their Fortunes

Man holding an empty wallet
Unsplash | Towfiqu barbhuiya

We live in an increasingly expensive world. While one might expect millionaires to be insulated from all of this, that isn't really the case. In fact, the world is full of millionaires who lost it all (or at least lost enough that they can't call themselves millionaires anymore).

If you want to feel at least a little bit better about your financial situation, check out these anecdotes from former millionaires who lost their fortunes.

Never emulate Nic Cage.

The Vegas strip at night
Unsplash | Kiefer Wright

"Gave most of it away in the divorce. Took what I thought would be enough to pull a Leaving Las Vegas. But Ben Sanderson had a big head start on me on the liver damage, so I outlived the money. Started over from zero sixteen years ago. Halfway back."


Two paths diverge.

Air Force jets flying in formation
Unsplash | James Lewis

"Grandfather and great uncle both went into the US Air Corps as bomber pilots. After the war, they both were offered prestigious high paying job flying for some airlines. Great uncle took the job, made a fortune flying and then got in the car business, becoming VP for a large American car company. Died rich in Jupiter, FL. Grandpa found Jesus during the war, declined cushy jobs to go to the seminary. Preached hell and mayhem as a Southern Baptist minister. As you can imagine I’m poor as my distant cousins grimace about two-year old Maseratis being out of style."


At least they kicked the habit.

Pile of assorted pills
Unsplash | Myriam Zilles

"Oxy and crack. $1500 a day habit got me high for a few years. Then the other half was when the dealers infiltrated and took me for 10's of thousands at a clip. Oh and a sibling stealing 400k was a dent as well. It's truly a miracle I'm alive. Nine years removed and finally dug myself out and back on top."


This might be the dumbest one on the list.

A monster truck
Unsplash | Gabriel Tovar

"I’d like to add something because its so ridiculous..my uncle and aunt inherited a lot of money. They paid to get a speedway fire truck restored that went straight to a storage unit. Wasn’t even theirs LOL. They took multiple trips to monster truck races, WWE events and the casino.. The funniest thing of all was they needed a new car badly but decided against it. They blew through all their money in less then a year and are now making car payments."


Financial smarts: not a genetic trait.

Rows of black and white shoes
Unsplash | Riyan Ong

"Not me but my grandma. She started a shoe company, it became one of the biggest retails in the south part of the country. Then as her retiring days got here she passed it on to her kids who ran it to the ground. She came out of retirement and within a year she she got out of debt and made it profitable again then went back to retirement. They ran it back to the ground and even put a mortgage on her house."


When you divvy it all up and only crumbs are left.

Hand holding some coins
Unsplash | Senad Palic

"COVID and divorce. We were invested in a small brewery that did not make it through COVID. We had two rental properties generating income in vacation spots that were shut down due to COVID. Had to sell one off at a huge loss. Ex wife then wanted a divorce and raked me over the coals. I won the other rental in the divorce and that's about it."


Terrible luck can strike anyone.

Stack of US $100 bills
Unsplash | Giorgio Trovato

"Twelve years ago, I was making 95K as a software engineer. I was in an accident, suffered a brain injury, lost everything, and haven't worked as a programmer since then. My injury easily cost me a million dollars."


Sometimes success comes before financial literacy.

Microphone in a recording studio
Unsplash | Leo Wieling

"My cousin was a big rapper in the 90s, when I say his name you probably know him or heard his music. It is still used today in the USA.

Anyway he became a millionaire really fast at 20 something years old after being a dishwasher.

His manager made him sign bad contracts and almost all of the money after a year or two went to his manager and accountant."


What happens in Vegas doesn't always stay in Vegas.

Famous 'Welcome to Las Vegas' sign
Unsplash | Grant Cai

"I was a flight attendant and once had a passenger in first class out of Vegas who looked distraught, handed me a 20 and said, 'Please keep the bourbon coming.' Inflight, he just drank looking down. I asked how he was doing. He said he was trying to figure out how to tell his wife he had lost their home gambling. That was the moment I decided I would never participate in a town that made its money that way."


You may not find love again, but you can find money again.

Torn paper heart on a string
Unsplash | Kelly Sikkema


I was a millionaire, got divorced which nearly sent me to insolvency, buckled down and worked my butt off and am re-millionaired.

Guys, don't underestimate the pernicious impact on net worth a bad divorce can have."


To be fair, they're two very different skillsets.

A barn and farmer's field in autumn
Unsplash | Frances Gunn

"My great grandparents were farmers and lived in North Dakota. In their prime, their team and them were absolutely great farmers. This along with some other factors made them suuuuper rich. For an example, they owned multiple planes and even had a hangar built to store them. They also had a really nice house (not a mansion, but a really nice and large one).

Well, it turns out they were really great at farming but not so much at paying taxes."


I wish I had a time machine.

One gold bitcoin
Unsplash | André François McKenzie

"Hypothetical millionaire.

I bought $100 worth of bitcoin when they were about $1 each. I sold them when they were about $2.50 each and was so happy I made money from 'internet coins.'

As of the moment I am typing this those coins would be worth $1,855,000."


The recession took a bite out of all of us.

"It's not a recession, it's a regression' graffiti on red wall
Unsplash | Annie Spratt

"We were close, then the great recession hit. Lost 60% in 3 years. Just updated the balance sheet today , we're almost back! Who knows what will happen in the next 24 to 36 months though."


Real estate can be volatile.

Keychain with a miniature house
Unsplash | Tierra Mallorca

"I got pretty close by selling my company to a bigger competitor. Reinvested most of it since I had not much use for the money but then got scammed for about half a million on buying some real estate. They smelled a newly rich kid from miles away. I still like to think I was worth a million at some brief point in time."


The more you make, the more interested the IRS is in you.

Folder full of tax paperwork
Unsplash | Kelly Sikkema

"Not me but an acquaintance. He got caught not paying taxes and dealing in stolen goods. He spent time in federal prison and lost everything, including his wife. Crime does not always pay!"


One guess as to that company's name.

An Enron logo
Wikimedia Commons | Paul Rand

"Not me, but a close friend's parents worked at a well-renowned American company in Houston in the early 2000s. They were really high up in the management chain and enjoyed a lot of the perks that came with their position, after sticking through thick and thin, especially during the dot-com bubble. Said friends parents were also very good in managing their money, living very frugally, and investing for their future nest egg.. Unfortunately, therein lied the rub.. All that investment (401Ks, extra cash, etc.) was on a single pot. I believed, with all their allocation (back in 2000's or so), they have had invested close to $5-6M and was due to pull it out so they could finally retire.

But a company scandal brought all that to a collapse."


Need to keep those ledgers in the black.

Hand holding a phone displaying stock trends
Unsplash | Javier Esteban

"I work in finance and my team and I work with all very affluent clients. I’ve seen so many millionaires lose it all not from investing in the markets, but from: Taxes, Lifestyle and poor business decisions.

Once had a client who was making 50k a month, but was spending 60k a month and perpetually dipping into his investments. There were months where payments bounced because he was living a lifestyle and always wanted more."


Probably the easiest way to lose your money.

Roulette table in a casino
Unsplash | Kaysha

"I watched a guy at a casino somehow get a loan against his house, about 200k and lose it. He looked suicidal. Apparently he was already in almost 50k and thought he could win it back. I got hired there, and I would leave on Friday and return Monday, and see the same people in the same clothes, who [soiled] themselves and were still sitting at the blackjack table gambling."


That's quite a track record.

Man holding an empty wallet
Unsplash | Towfiqu barbhuiya

"My dad is an ex-millionaire.

He's a wizard at starting successful businesses...

His problem is he can't let them go. He's the boss/owner who never hires a manager that's not family because he just doesn't trust anyone else to run it.

He drove 3, million dollar companies into the ground because he couldn't keep up with his own success, and refused to hire people to do it for him."


Money can't buy everything.

Bed in a hospital room
Unsplash | Martha Dominguez de Gouveia

"First husband. Was making a million a year. He was enjoying life- spending frivolously, but bringing in enough that it didn’t matter. We divorced, but amicably (no alimony, no ‘child support’, he just paid for whatever the kids needed). Then he got leukemia. He fought like hell for three years. The last two years were very expensive. It was worth it. Money won’t make you happy, but the lack of it can destroy you."