Freelance game coaches monetize their gaming expertise by offering personalized instruction to players seeking to improve, working through gig platforms, yet little is known about how they operate. To address this gap, we conducted semi-structured interviews with 20 experienced freelance coaches across 17 competitive games on Fiverr. Despite lacking shared formal training, these coaches converged on similar practices centered on rapport-building, individualized diagnosis, and adaptive feedback. We identify two structural conditions shaping this work: dual precarity, in which coaches navigate both gig platform instability and the lifecycle volatility of live-service games; and earned authority, in which coaches must continually establish legitimacy through visible competitive achievement within the same gaming spaces as their students. These coaches welcomed AI for administrative and analytic support but resisted its use in live interactions where trust, relational engagement, and situated judgment remained central. We discuss implications for Games HCI and the design of computational coaching systems.

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