When can you be confident that you are a winner?

[Mr_J]

Nope. 374x$110 bet = $41140.
2644/41140= 6.43%.

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I would adjust my unit when my bankroll has grown 20%, and never adjust when my bankroll is down.

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I prefer to resize everyday when you are betting a small unit size, but plenty of people use thresholds and there's not really anything wrong with it. However, not adjusting when you are losing is a recipe for disaster.