This chapter adds to a growing subfield of music festival studies by examining the business practices and cultures of the commercial outdoor sector, with a particular focus on rock, pop, and dance music events. The events of this sector require substantial financial and other capital in order to be staged and achieve success, yet the market is highly volatile, with relatively few festivals managing to attain longevity. It is argued that these events must balance their commercial needs with the socio-cultural expectations of their audiences for hedonistic, carnivalesque experiences that draw on countercultural understanding of festival culture (the countercultural carnivalesque). This balancing act has come into increased focus as corporate promoters, brand sponsors, and venture capitalists have sought to dominate the market in the neoliberal era of late capitalism. The chapter examines the riskiness and volatility of the sector before examining contemporary economic strategies for risk management and audience development, and critiques of these corporatizing and mainstreaming processes.