Precautionary Tales From Ex-Millionaires Who Lost it All

1. “I have a relative who is a self-made millionaire many times over. He was the hardest working person I’ve ever known. As soon as he graduated from high school he got his real estate license and became a successful realtor. Within 30 years he opened a successful construction company, a store that sold kitchen cabinets, and owned over 20 rental properties. This wasn’t enough form him and he started renting out his properties to people that would pay him more to grow pot in. His granite company was used to ship the pot across state lines and now he’s sitting in jail facing a minimum of 10 years. The government is coming after all his rentals and money.”

2. “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.”

3. “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!”

4. “My dad is an Ex-millionaire. He’s a fucking 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.”

5. “Somewhere here there’s a billionaire laughing because they’re an ex millionaire too.”

6. “I was a multi-millionaire for two weeks. Then the vacation was over and we exchanged our Dongs for Euros.”

7. “A common template for wealth loss is underestimating the role of luck in the initial wealth accumulation, and, as a result, taking irresponsible risks on new ventures and/or maintaining lifestyles that overestimate future earning potential. I have seen this with some folks who made money in finance in the 80s and 90s. While extremely smart and hard working, their path to tens or hundreds of millions of dollars were also pretty lucky.”

8. “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 pissed and shit themselves and were still sitting at the blackjack table gambling.”

9. “A lot of people who win the lottery will blow their money on big purchases, like a house or a yacht. Then they have no money left to pay the yearly costs of those items, and they lose everything. Invest all your money in safe stocks, get a mortgage on a house, and chill the fuck out if you win the lottery.”

10. “You know how to end up with $1M after a year of day trading? Start with $2M!”

11. “My alarm clock that woke me up”

12. “Divorce. 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.”

13. “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. The kids and I can take comfort in knowing that truly, there was nothing else possible. His millions bought his kids two more years of dad. And I’m glad for him that he enjoyed his life while he could.”

14. “My favorite investment advice: Same car, same house, same spouse”

15. “Gambling and spouse terminal illness.”

16. “Crypto millionaire. Still worth a lot, with my accounts about $850,000 today (I have a lot of xrp) But in 2017 I was worth about 3.5 million before the crash. Lowest was $300,000. I’m a holder so I don’t day trade usually.”

17. “We were close, then the great recession hit. Lost 60% in 3 years. Just updated the balance sheet today, we’re almost back!”

18. “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.”

19. “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.”