Andrea Olshan was one of a small set of women to move into leadership roles as second- or third-generation members of New York-based, family-owned real estate companies. Olshan joined Olshan Properties, the 60-year-old firm her father had founded, in 2004 and stepped up to the CEO position in 2012. Reevaluating her father’s “buy, hold, manage” business model, Olshan took steps to de-centralize decision-making and to transition to a more institutional platform. This case provides background on the firm’s organizational design, business model, and asset profile and asks students to consider what the firm’s best path to continued growth should be?