parlay, parley

Parlay or parlay means to bet again when you win, wagering the original bet and the winnings--
If he wins he will parlay it on the favorite in the next race.
He won the bet and the parlay; now he has a heap of money.
Parlay may also mean to increase a sum of money by some form of wagering or deal-making--
He hopes to parlay his stake into a few thousand dollars.

Parley or parley means a discussion or conference between spokesmen for two opposing sides or camps, as during a war--
They are waving a white flag; maybe they want to arrange a parley.
They want to know if we'll agree to a parley.
Parley may also mean to hold a discussion or conference with an enemy; or to discuss or confer with an enemy as to terms--
The captain wants to parley with the enemy; but the major says no.
The cease-fire will begin at noon; then we'll parley.

Now that you know that, you can say--
"He hopes to arrange a parley with the loan shark, if he can parlay his winnings into a respectable sum."