Yes, being an entrepreneur can oftentimes be an “expensive” learning experience. While I’ve been involved in the financial services and insurance business for most of my career, there was a point in the mid-2000s where I considered changing careers to become a real estate investor. Unfortunately, timing is often just as much of a factor in your business success as money, experience, and well, just about anything else. In this case, I went on a property buying spree at the top of the market – just a few years before the big market crash of 2008. This meant that I not only purchased several properties that were essntially way over valued (and overpriced), but when I went to sell them in 2008-2009, I didn’t get nearly what I had planned on. In fact, in one particular case, I spent in excess of $5,000 fixing up a house (after my tenant destroyed almost every inch of it), and then still had to bring $17,000 with me to closing as the seller! The lesson learned here, among others, was to stick with what you know…especially if the endeavor requires a large out-of-pocket financial commitment from you.