Youth content creators have been under-researched on video platforms such as Snapchat, YouTube, Instagram, etc. In order to better understand the ways that technology could support youth as content creators we conducted a 30-week series of workshops with an intergenerational design team including pre-teen youth and undergraduate designers-intraining. Qualitative analysis of workshop videos and notes revealed underlying challenges in video creation related to the social dynamics of creating videos in groups. In line with previous work, we note that a primary motivation for using social media is to spend time with friends. We found that existing video technology reveals opportunities and challenges to support the collaboration and interaction that motivates youth creators. We offer illustrative designs of potential collaborations in video sharing technology and propose that some of the concerns of youth social media use could be addressed by incorporating more opportunities for social creation.