Do you remember this TV advertisement for the Apple Macintosh from 1985?

In the advertisement, it shows people stepping off a cliff like lemmings. One of the great advertisements of all time.

Have you ever felt like one of those guys stepping off the cliff when it comes to investing? Just about every time I’ve put money into the stock market, I’ve lost money.
The biggest problem with investing in an individual stock is that you can’t see all the things that are going on in the business that business. They may be cooking the books, or that they may be having problems with sales. You as an investor in a company like that don’t get wind of those types of problems until it’s too late. When you finally find out, everybody else know and your investment has already taken a hit.
But when you have almost complete control of your business, like for instance, if you’re buying and holding properties. In that case, you get to see everything that goes on AND you can have a direct influence on everything that happens. You have ultimate control on how you do in the business. That’s why I believe you can be so much more successful with type of business/investment.
You know just from common sense that people need a place to live. And you know times can get pretty tough, and there’s still going to be people who needs a place to rent.
A tough economic time is just a good indication that there will be more good real estate deals to be had. The tough economy creates uncertainty in the mind of the average investor. But I think just being able to control your business is the difference between making money and loosing money in this tough economy.
Every time I’ve gotten away from real estate as in investment, I have lost money. Particularly in the stock market. When you invest in stocks, you have two basic choices. The first option is own the stock (buy and hold). The second is to sell it. But with real estate, you have numerous choices. You can make any number of changes to a property to affect it appearance and/or function. You have rent it many different ways. You can sell it many different ways.
That’s why I prefer real estate to all other investments / businesses I’ve ever seen.
If you keep things simple, and do the things that make common sense, you’ll do fine in real estate investing. People have use buy and hold as way to get rich with real estate for hundred of years. If I can do it, you can as well.

Do you have any stories about money you’ve lost from investments where you should have know better in hindsight? Please write a comment if you do.