I had an experience over the Christmas holiday that made me think a lot about investing, and particularly about what holds back many smart, capable people from becoming successful investors.
At a family dinner party, I sat next to the spouse of one of my wife’s cousins.
We are about the same age, have similar backgrounds, interests, family dynamics, etc.
While we were talking, my brother-in-law, who just got married and is attending a local university interrupted our conversation to ask about renting a condo I own near the university.
We briefly talked about its location, features, price and availability. After making a note to let my property manager know that my brother-in-law wants to rent it as soon as its available, I came back to the conversation I was having with my wife’s cousin.
This interruption shifted our conversation onto me. He asked me about the property and real estate investing.
As he went deeper with his questions he discovered that I own over 20 similar properties. What fascinated him more was these were not all in my backyard but they were spread across the entire country.
He asked me to elaborate so I shared with him that I also regularly participate in investments such as apartment buildings, hotel developments and renovations as well as large office buildings.
Then he made this comment: “I wish I could invest like you but I’m just not a risk taker.”
It made me think a lot about myself and my investing philosophy.
You see, I don’t view myself as a wild-west, gunslinging, riverboat gambler type.
On the contrary, my natural tendency is to research and fact-find. My background is accounting and statistics, and data and analysis often trip me up and slow me down.
As I thought about this, I remembered a great book written by one of my mentors Michael Masterson called “The Reluctant Entrepreneur.”
In the introduction, the author described himself and why he titled the book the way he did.
“I started my first business because I wanted all the benefits of entrepreneurship–the independence, the prestige, and the money.
But I have never been willing to risk much to get those benefits.
In other words, I wanted my cake. And I wanted to eat it too.
That’s why I call myself a “reluctant entrepreneur.”