The lottery

In 2002, a man named Jack Whittaker won over $300 million in the lottery. He was already a millionaire at the time, but like many other lottery winners, his life took a turn for the worse. He did donate 10% to churches and even more to charity, but he had a bad habit of leaving cash in his car and getting it stolen, he blew a lot of it on casinos, his house got robbed, and his granddaughter got killed, presumably for drugs or money.

I was surprised when I read it because rich people seldom play the lottery (except when the prize is high, and I'll get into that in a minute). Especially someone like him.  Jack lived simply.  Not many people knew he was wealthy. Self-made rich people tend to be very calculating with their money and know that the probability of winning is so low as to be non-existent. You'd be much better off just putting the money in a savings account. One reason most lottery winners tend to lose all their money within 3 years is that they overspend. Friends and strangers ask them for money, and many oblige. They buy luxury stuff that only makes them happy briefly. It strains their relationships.

Do you know what the difference is between someone who made $30 million and someone who won it? The first had to work for his/her money and the second was simply given it. Money you earn is much more difficult to part with.

Poor people play the lottery regularly, while rich people are more calculating and only tend to play when the prize is very large: http://www.businessinsider.com/how-rich-people-and-poor-people-play-the-lottery-2012-3

I still buy a lottery ticket every now and then, in spite of knowing that the lottery is a "stupid tax". If you ever win, make sure you set aside a good portion of it into low-cost investments (diversified index funds are my suggestion), and feel free to splurge the rest. Just make sure you can actually cover the whole cost of that house/car/island with the remainder and not have to dip into your investments.