Of course, strategy is one thing; execution is quite another.

"I sometimes fear that, despite the $45 million in capital behind me and my years of hard-earned business savvy, I’m going to screw up one day and lose everything."

Overcoming the fear associated with investing has been a gradual process. My biggest breakthrough came when I started thinking like a CFO, and not as a cash-strapped consumer. Most of us have been raised to believe that debt is a bad thing, and that is not entirely wrong. Anybody who is dumb enough to pay 19 percent interest on his credit card balances or lease a fancy sports car for $2,000 a month deserves what he gets. Personally, I take great pleasure in annoying the consumer finance companies by paying my credit card bills in full every month and driving a two-year-old PT Cruiser that I bought for cash. When it comes to my investment portfolio, however, I now feel very confident in using leverage to boost the returns on my real estate and other investments–as long as my inner CFO first checks out the numbers and decides they make sense.

Command and Control
It may seem odd that a woman sitting on $45 million should play such a hands-on role in the management of her portfolio. Some affluent investors simply turn it over to their wealth advisors, with whom they meet quarterly. Well, I do have wealth advisors–and accountants, attorneys, real estate brokers and plenty of other service providers who help me. Yet, because I did not start life with a silver spoon in my mouth, I will always think like a small-business owner with my hand on the throttle and my eye on the checkbook. This is probably, to some degree, an issue of trust. Even more so, it is an issue of control.

That is why I do not make a single investment decision without crunching the numbers in an Excel spreadsheet. While math was never my best subject in high school–I was the kid who was reading Pride and Prejudice and writing poetry in the park–it does not take a rocket scientist to put together a quick profit and loss statement to analyze the best- and worst-case scenarios of a particular investment decision. As I tell the clients who come to my small-business consulting firm for help, you must fight the battle on paper (or, in this case, a computer) before you risk deploying one dollar in the field.

I have also learned to continually reevaluate my investment strategy as the market changes. That is why I religiously read the New York Times, the Financial Times, the Wall Street Journal and anything else I can get my hands on. That is also why I keep a monthly spreadsheet (ah, yes, those spreadsheets!) that shows me to the penny how much each of my investments is worth. While it is tempting to blindly follow the advice that most wealth advisors offer about sticking with an investment strategy no matter what, your soup will burn if you are not watching the pot. Just ask anybody who bought dot-com stocks in February 2000 figuring that the market could only go higher.

When people meet me for the first time, they often wonder about my transition from newspaper reporter to dot-com CEO to management consultant and investor. How did I manage to learn all this stuff without having taken a single business course? To me, it’s all part of the journey that began back when I bought my first house in West Palm Beach, Fla. I didn’t make much money on that little house, but I did not lose it in a foreclosure sale, either–and I learned a lot of lessons about fear, investing and myself along the way.

Photograph by Thomas Hart Shelby.