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Roll a 20-sided die, keep it or re-roll once

Asked at Jane Street, Optiver

You roll a fair twenty-sided die (faces 11 through 2020) and are paid its face value in dollars. You may either keep it, or discard it and roll once more, taking whatever the second roll shows.

What is the optimal strategy, and what is the fair value of the game?

Show a hint

The re-roll is worth the mean face of a d20. Keep only faces above that mean.

Your answer

This one is open-ended. Work it through, then check your reasoning against the full solution.

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