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Milan (Italy), September 2018. The Strategic Lab at De Agostini, part strategic think-tank and part assessment tool for the next-generation talent of the Drago-Boroli family, owners of De Agostini, was brainstorming the future direction of the diversified, family-owned group. After almost 100 years in the publishing and printing business, the third-generation family leader Marco Drago set the family firm on a radical new course, which included globalization and diversification across media and communication, gaming, and financial services to create a powerhouse, with entities listed on three different stock exchanges. However, diversification did not come without its challenges. Could portfolio repurposing also serve to anchor the family's identity? Were family values properly embedded in the current structures and investments? Should the holding structure be perennialized or be treated as a temporary arrangement until the next major liquidity event, when assets would again be refocused on a single industry? Did the legacy publishing business still serve a purpose or should it be disposed of? Emotional ties ran deep, but so did the losses... and those were not sustainable. Could it be turned around or pivoted to capture the latest digitalization wave?