One of the most famous examples: Jesse Livermore[1], whose Reminiscences of a Stock Operator[2] is one of the most recommended trading books ever. (I recommend it too. It's awesome.)
He never climbed the corporate ladder, but did start out writing prices on a blackboard for a brokerage. He went on to become a hugely successful trader, only to lose it all, and repeated this cycle many times.
[1] - https://en.wikipedia.org/wiki/Jesse_Lauriston_Livermore
[2] - https://www.amazon.com/Reminiscences-Stock-Operator-Edwin-Le...
https://www.amazon.com/Reminiscences-Stock-Operator-Edwin-Le...