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Best threshold for a d20 roll-or-cash game

Question

You have 100100 moves and a fair 2020-sided die whose top face currently shows 11. Each move is either a roll, which re-randomises the top face, or a take, which pays you the number currently on top in dollars without ending the game; takes do not require a roll in between (so taking 100100 times immediately guarantees $100). You commit in advance to this plan: roll until the top face is at least nn for the first time, then take on every remaining move. Choosing nn optimally, what is the expected payout?

Short answer

5320/3≈1773.335320/3\approx 1773.33 dollars. With threshold nn the face you lock in averages 20+n2\tfrac{20+n}{2} and reaching it takes on average 2021−n\tfrac{20}{21-n} rolls, leaving about 100−2021−n100-\tfrac{20}{21-n} takes. The product is maximised at n=18n=18: 19⋅(100−203)=5320319\cdot(100-\tfrac{20}{3})=\tfrac{5320}{3}.

Adapted from QuantQuestions.io; question and answer rewritten by SelfMadeQuant.com.

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