I once asked my handyman what was the easiest money he had ever made in his life. His answer was that although he had been in many small businesses and had done countless handyman/contracting jobs over the years, the easiest money he made was in roofing. He explained how that roofing work is higher risk work that many folks dislike and fear doing, therefore the mark-up is tremendous.

He especially likes smaller flat or semi-pitched roofs. For about $250 in materials he could charge $1,000 for a roof which he could install in a day. Larger, shingled roofs have even better mark-ups, although more time consuming.

I then began asking myself the same question. What was the easiest money I had ever made in business or investing?

There are 3 ways or modes (versus tools and techniques) that came to my mind quickly.

1. By far the easiest money I have ever made was from real estate appreciation. I have been fortunate to have been in the game long enough to ride two giant waves of appreciation and inflation. The price run-up that occurred in the mid to late '80s, and the current bubble we have going now. Any dummy can make money in real estate during strong seller's markets. It makes you feel smart, but the main smart thing you really did to achieve it was to be smart enough to buy it.
   
    

2. Next, buying discounted property through patient tracking and buying of properties is the next easiest money I have made. Like when I bought a $20,000 house for $2,800. Nuts, but true. Or, like the $20,000 purchase with 100% owner financing which was resold via lease option for $39,000.
   
   Thoughtful and determined deal making is the second easiest way to make money in real estate. The cliché is true - you make your money when you buy. One caveat: Lower-income grade deals must be outrageously beneficially-priced to be worth the risk. Solid, middle-grade properties need not be "steals" to be good buys. A few years ago, I bought 2 houses from my attorney at decent to fair prices, but they were in excellent areas and have ALL brick exteriors with new roofs. They weren't steals, but they have appreciated by $20,000 each since acquisition.
   
    

3. Lastly. Rents. This takes time as I mention over and over, but once properties become seasoned and rents rise and debt drop off - rents are easy money. The problem - few have the future sight to maintain their hand in the game. It is a wonderful business to learn. Most landlords don't work very hard.
   
    

4. Rehabs and Interest Profits. Yes, these could be debated as easier than rents, but without rents you can't get number 1 - Appreciation and Price Inflation from governmental debt-driven inflation. And, you pay a lot more taxes, therefore limiting your net worth growth.