In my opinion, risks taken and loses suffered are a great way to know about someone's skills and quality. You can't expect great stuff from people who have never put anything at stake.

This thinking makes me hate when people glorify executive leaders in big corporations as if they were touched by god just by being there. I've met many of them, and many are just obedient bees whose biggest credential is patience and loyalty, but have never actually done proper business. Not even a fucking lemonade stand.

Some others do have taken professional and personal risks, and it shows.