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Entrepreneurship is ubiquitous, but it is not unequivocally a human force for social and economic good. Critical perspectives of the entrepreneur, entrepreneurship, and entrepreneurial success (and failure) are evolving in the scholarly literature. Dark side theory has emerged as a language for critiquing the dominant narratives of entrepreneurship portrayed in scholarship, education, planning, policy, and other forms of practice. This chapter draws from dark side entrepreneurship theory, Baumolian entrepreneurship, and exemplars of counterculture to craft language for an emerging theory of misfit entrepreneurship, which consists of misfit entrepreneurs and alternative enterprises. Alternative enterprises and misfit entrepreneurs are conceptualized, and literary examples (i.e., Robin Hood and Song Jiang) and modern-day examples (i.e., Hacker groups) are supplied. The unique actions and impacts of misfit entrepreneurs and alternative enterprises are offered for discussion. This new theory of misfit entrepreneurship leaves readers with exploratory questions that enhance critical perspectives and modern understandings of entrepreneurship today.