Read Next

Enjoying Paying for Value

Beginning around high school, one of my major core values was paying the least possible amount for everything. I was always trying to figure out how to get things for massive discounts or to orchestrate some complex trade so that I got whatever I wanted for free in the end. I got so good at it that my first real income-producing business was in high school when I was buying and selling Palm Pilots and Apple Newtons. I started that business with the purchase of a $70 Newton and never invested more outside money into it.

Being frugal can be good. At it's best, being frugal is the practice of deciding whether you actually need something or not, whether it will be worth it to you, and carefully stewarding your money. Most people should probably be more frugal.

Over time, however, I realized that my frugality had turned into something different. I felt as though I didn't win unless someone else lost. When I went to a buffet, it was important to me that I ate so much that the casino lost money on me. Either I was the sucker or they were the sucker, and I didn't want it to be me. One of the best things at the Bellagio buffet was the pesto mashed potatoes, but I would only allow myself tiny amounts of them because I didn't want to fill up on cheap potatoes.

My business immediately after the Newton trading business was professional gambling, which was very much a win-lose situation. The casinos were trying to force me to lose and I was trying to do the opposite to them. The experience of being a professional gambler was very valuable to me, both financially and mentally, but I wonder if it helped ingrain into me that idea of not wanting to enrich companies.

Rendering New Theme...