Explicit formulas are found for the payoff and the optimal stopping strategy of the optimal stopping problem supτE (max0≤t≤τXt − c τ), where X = (Xt)t≥0 is geometric Brownian motion with drift μ and volatility σ > 0, and the supremum is taken over all stopping times for X. The payoff is shown to be finite, if and only if μ < 0. The optimal stopping time is given by τ* = inf {t > 0 | Xt = g* (max0≤t≤sXs)} where s ↦ g*(s) is the maximal solution of the (nonlinear) differential equation under the condition 0 < g(s) < s, where Δ = 1 − 2μ / σ2 and K = Δ σ2 / 2c. The estimate is established g*(s) ∼ ((Δ − 1) / K Δ)1 / Δs1−1/Δ as s → ∞. Applying these results we prove the following maximal inequality: where τ may be any stopping time for X. This extends the well-known identity E (supt>0Xt) = 1 − (σ 2 / 2 μ) and is shown to be sharp. The method of proof relies upon a smooth pasting guess (for the Stephan problem with moving boundary) and the Itô–Tanaka formula (being applied two-dimensionally). The key point and main novelty in our approach is the maximality principle for the moving boundary (the optimal stopping boundary is the maximal solution of the differential equation obtained by a smooth pasting guess). We think that this principle is by itself of theoretical and practical interest.