It’s been five years since the Canadian government legalized and regulated non-medical cannabis cultivation, commerce, and consumption. California is ahead of us by two years, having followed a similar experiment in 2016 when it legalized recreational cannabis. Today, California and Canada are facing similar challenges though they have adopted vastly different regulations. The two jurisdictions offer an interesting contrast in how regulatory frameworks can support or undermine a nascent legal cannabis industry. Evidence from the past five years suggests that the regulations have failed to provide equitable access to the industry and develop balanced tax structures. Legalization in Canada and California also remains hampered by the legacy of global cannabis prohibition.