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How do billionaires handle risk?

Short answer

They take risks, but they think about the downside first and size their bets.

What Billionaires Told Us

Tim Draper
“It’s to avoid fear, don’t make decisions based on fear. Go ahead, use your fear to figure out what could go wrong, but then always invest for what if it works?”
Tim Draper, in our interview
Pearl Kapur
“Now, is the time to take risks. As you get older, obligations increase, and once you have a family, you start taking risks not just for yourself but for your family as well, it gets much harder to do things that might not work out.”
Pearl Kapur, in our interview