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After the third variation, the lines repeat.
Also, you can win back 150% your investment later on, but only up to 90$, so stop investing after you've heard the third line. ;-)
Actually you can get more than that back if you stack gear that boosts money gains. With Fatbeards Blade, the Assassin costume set and the two "Magnet" patches I managed to win back $150 or so from him.
He's an easy fight, so the equipment change isn't really an issue. Just remember, no more than THREE investments.
To specify, the hole is to the left of the room behind the bank counter along with a chest in the room with him.