To lose a lot of money.
たくさんのお金を失う。 (takusan no okane o ushinau)
"He lost his shirt gambling last night."
"彼は昨晩ギャンブルでシャツを失った。" (Kare wa sakuban gyanburu de shatsu o ushinatta)
to continue believing in your goals even when it's hard
to remain valuable or successful for a long period of time
to settle and become established somewhere
To use all your energy and resources to achieve something.
There is no point in worrying about past mistakes.
In a position to be injured or in danger.