Many digital platforms thrive on the contributions of volunteers—whether as content creators, moderators, or community developers. Yet, as platforms scale and introduce monetization strategies, they risk alienating these communities. When Reddit changed its API pricing in 2023, what seemed like a routine business decision triggered mass blackouts by volunteer moderators, hobbling the platform. A decade earlier, unpaid Huffington Post contributors, feeling exploited, staged strikes and filed lawsuits following AOL’s $315 million acquisition. These cases highlight a recurring challenge: how platforms can commercialize without undermining the volunteer-driven systems that make them valuable. This article—drawn from our ongoing research—will offer lessons from companies that stumbled and insights from organizations that navigated these challenges successfully.