Potential answers for "___ to something (be successful)"

⭐⭐⭐⭐ AMOUNT
⭐ LOSERS
⭐ TROPHYWIFE
⭐ HIDDENBALLTRICK
⭐ BOFFO
⭐ FAR
⭐ BEARSFRUIT
⭐ INS
⭐ HITS
⭐ FILTHYRICH

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Loud sleeper   Gloomy ___ (pessimist)   Side of a cut diamond