Rylan began playing ice hockey with boys on the Tampa Bay Junior Lightning as an elementary school student.

[5] Prior to joining Northeastern University, Rylan played one season with the Division II club program at the Metropolitan State College of Denver, a men's team that competes in the American Collegiate Hockey Association.

[6] Rylan was inspired to create a women's league while watching the United States and Canadian national teams play in the finals of the 2014 Winter Olympics and began researching the new business opportunity.

Rylan remained with the league to oversee the Beauts, Whale, Riveters, and Whitecaps while it searched for independent ownership of the league-operated teams before resigning from that role in March 2021.

[6] After college, she moved to New York City and opened a coffee shop named Rise and Grind in East Harlem.