I can imagine it'd be like fishing or hunting. Relaxing if you're doing it as a hobby, potentially frustrating if unsuccessful and your livelihood depends on it.
It's more like being a journalist with billions of dollars behind you.
Or a detective investigating situations in which a favourable outcome means you make boatloads of money.
If you're at the executive level you likely have enough connections and savings that you can afford to occasionally fail without substantially affecting your quality of life.
Anybody can risk enough to fail in an irreparable way.
That doesn't mean anybody _will_ risk enough to fail in an irreparable way.