3Risking

Without risk, there is no reward.

You can't win if you don't play.

The most admired businesses in America today were built by those who risked their own futures and financial solvency to translate their dreams into an industry. In this chapter, I'll explore what it means to take a risk, covering those who gambled and won big, as well as those who played it safe to their own detriment. I'll talk about how a culture of risk‐taking shaped who I am and the business we'd go on to create, the checks and balances we put in place to ensure its success, and the one thing you must know above all else.

While I can't make the decision to take a risk for you, I will repeat the adage that fortune favors the bold.

Changes in Attitudes, Changes in Latitudes

My early life was shaped by my parents taking the risk to move to Portugal in 1974, a time when going the expat route wasn't so common. The world was far less connected in the 1970s and some of my parents' peers questioned our family's decision, peppering my folks with what‐if questions and speculations on worst‐case scenarios. But my parents weren't impulsive people, and they weighed all the possible outcomes, comparing risks to rewards, long before they placed any of our belongings in a cardboard box. If my father had his druthers, he and my mother would have moved to Spain in 1961, the year after they got married, ...

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