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This chapter provides valuable insights around the entrepreneurial landscapes of the twenty-first century, as well as the inherent stressors that may impact entrepreneurial well-being and performance. As the World Health Organization declares stress as the epidemic of the twenty-first century, entrepreneurs face increasingly volatile, uncertain, complex, and ambiguous contexts, or what the Army War College refers to as “VUCA” environments. In these contexts, traditional models of leadership and stress management in entrepreneurship require tapping into new, sometimes previously untapped and underdeveloped resources. Resources such as Psychological Capital (Luthans, Youssef-Morgan, & Avolio, 2007), Algorithmic Leadership (Harms & Han, 2018), and wearable biometric technologies (Tsuji, Sato, Yano, Broad, & Luthans, 2019) that exploit big data analytics powered by artificial intelligence will be invaluable to entrepreneurs as they manage stress, and build and maintain their competitive edges.