Third-Generation iPad Jailbroken on Launch Day

This is an ongoing chess game. As for "winning" I know lots of people that make six figure incomes in the information security arena.
Loosers?

I know many people over the past decades that started in the "blackhat" arena, and then went on to run companies doing information security.
Loosers?

These people are currently designing the information security systems that people are learning how to attack.
Loosers?

If people that do information security don't "win", how come there has to be new exploits?

I'm obviously not understanding what it means to "win," or "loose."

Apple won't loose anything. Even they make 0 dollar from selling software if the user jailbreaks the iPad, they still make money from the selling iPad hardware itself.