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A study of the globally oriented expansion strategies of Uber and Airbnb offer business leaders insight into dealing with the ups and downs of the sharing economy. Although both firms have suffered operational and managerial setbacks and face logistical and regulatory hurdles, they continue to enjoy remarkable international growth. Thanks to their entrepreneurial initiatives, application of digital models, savvy branding, and customer‐centric focus, Uber and Airbnb remain staunchly competitive in each of their demanding sectors. Their experiences highlight the value of efficient business models, niche strategies, and connectivity.