Stack the deck so you win, even when you lose.
Contrary to popular belief, the greatest investors don't take gigantic risks. Average investors, certainly. Good investors, maybe. But not great investors. Rather, they minimize risk and maximize return.
Richard Branson, creator of the world renown Virgin brand, started Virgin Airlines by hedging his losses. He made a deal with Boeing that if, after two years, the airline wasn't doing well, they could return their fleet of airplanes at no risk. It's not quite free airplanes but it's as close as you'll get.
Stacking the odds in your favor is important to consider so that even when you're wrong and you take a loss, you come out ahead of where you were before. It's what Tony Robbins calls, "asymmetrical risk-reward." For Branson, if the airline failed, he didn't lose much and he gained the experience and knowledge of that industry. If he won, he made billions. For us folks who aren't starting airlines in our spare time, it might look something like this:
Imagine you're face with two job opportunities. One is a large company that pays really well and provides you with incredible benefits but operates under lots of bureaucracy and will take you years to move up the corporate ladder to a position you really love. The other is a small company with less pay and virtually no benefits but lots of opportunity to take on projects that you wouldn't touch at the large company, learn in a fast-paced, hands-on environment and do what you love more quickly.
If you choose the large company and it fails, you no longer have the cash, nor the benefits, nor the experience. On the other hand, if you choose the small company and it fails, you walk away with knowledge and experience that you can leverage for a better position in a larger, more stable company later.
I'm not saying everyone should go work for a small start up - your season of life might be better suited for the large company. But...