While managing the Ceilidh Connection Internet Cafe and Lounge as an all-ages venue, numerous issues arose with the Alcohol and Gaming Authority (AGA). Although the cafe was a licensed restaurant, which allowed both the serving of alcohol within a designated area and the presence of minors within another area, the AGA felt the presence of entertainment created a lounge atmosphere within the establishment that was inappropriate for minors. This decision meant the immediate termination of shows involving minors at the Ceilidh Connection.

With the support of the all-ages community, Ryan and those who had been volunteering at the Ceilidh organized a protest concert outside of city hall. Dubbed the Tumbleweed festival, the event provided a stage for both musicians and the audience to voice their opinion on the importance of the all-ages scene within Halifax. Although a compromise was met before the event date, the festival proceeded as a celebration of the music scene within Halifax and the Maritimes in general.

Over the next few years, four more Tumbleweed festivals would be organized. All of these festivals were free for those who attended, none of the musicians were paid for their performance, and each event was organized and overseen by Ryan and a team of volunteers, all of whom were minors.