Based on mediatization theory, this article tracks how skateboarders experience and negotiate the entry of social media into their subculture. Building on existing scholarship, I show how social media and digital devices retain existing values within the culture while simultaneously introducing new challenges. To illustrate the phenomena of continuity and novelty in the online skate subculture, I analyze two case studies pertaining to YouTube. The first is a textual analysis of a typical skate video. Released on YouTube in 2020, the BE FREE video exhibits neoliberal, apolitical, masculine, and individualist values that go back decades in skate culture. The second case involves one of the most popular hubs of online skateboarding today: The Berrics YouTube channel, which claims 1.3 million subscribers and over 4,500 individual videos. I show how The Berrics maintains a one-dimensional positivity through its posts and interactions with fans, and I argue that it is still experimenting with the handling of negative feedback that participatory media allow. I also provide a brief history of skateboard media to properly contextualize these case studies.