Risk is the ultimate differentiator. I have always had a deep and complex relationship with it. I am not a reckless person, but taking risks is really the only way to consistently achieve above-average returns — in life as well as in investments. My father proved that when he left Poland. I am probably more comfortable with risk than most people. That’s because I do as much as I can to understand it. To me, risk-taking rests on the ability to see all the variables and then identify the ones that will make or break you.

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There’s a line from an old movie, Wheeler Dealers: “You don’t go wheeling and dealing for the money, you do it for fun. Money’s just a way of keeping score.” And that’s how I see it. I’ve always been much more drawn to the experience.

While I was unaware of it at the time, my real compensation for that job wasn’t monetary. It was learning about and getting comfortable with rejection. And as I would later realize, indifference to rejection is a fundamental part of being an entrepreneur.

In addition to looking at worst-case scenarios, I look at how hard something is to execute. The simpler the goals and the steps to reach them, the more likely I’ll be successful. And if they aren’t simple to begin with, I look at how I can untangle the complexities.

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Jay taught me to use simplicity as a strategy. He had an uncanny ability to grasp an extremely complex situation and immediately locate the weakness. He always said that if there were twelve steps in a deal, the whole thing depended on just one of them. The others would either work themselves out or were less important.

I was targeting good real estate assets overburdened by excessive debt. Well, I began seeing similar scenarios unfold in the corporate world and realized I could provide equity to those companies for a stake at a discounted price, and that would help them position themselves for when the market recovered.

I said, “You’ve got to be able to look at the deal and know what it hinges on to know whether it works or not. If you realize that the key component works, then you use the numbers to test it. You don’t do the numbers to find out eight hours later whether it was worth starting.” I’m sure his IQ was higher than mine. But that isn’t how we operate. You have to be able to effectively assess the initial picture and see where the greatest risk is most likely to be, or you’ll spend your life doing numbers just to find out if a deal will work. And all that time lost is time you could have been looking at other opportunities.

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The third acquisition was a big single-family house. I found an architect, a small local general contractor, and we created a design for four separate units. Then I went to the bank and got loans to do the renovation. I was twenty-three, with a BA in political science. I didn’t know anything about financing. But it never crossed my mind that I might be too young to start an investment business or that I couldn’t do it. I didn’t know any better, but was able to sell the banks on my ability to get it done. Our management company took over the property, did the renovation, and rented the units. The asset did very well.

In real estate I’m known as the Grave Dancer. That was the title of an article I wrote back in 1976, and the nickname stuck. Some might see buying and creating value from others’ mistakes as a form of exploitation, but I see it as giving neglected or devalued assets, in any industry, new life.