Although federal law in the United States continues to list cannabis as a Schedule I drug, making it illegal, states across the country have legalized the cannabis industry. But the conflicting public policy creates numerous challenges for those in the industry. James Schwartz, CEO of Cascade High Organics, leads a startup in the cannabis cultivation industry in the state of Oregon. The fourth quarter of 2017 saw a huge glut in product in the cannabis industry resulting from activities in a black market that provides almost 65% of black market cannabis trade in the United States. This case examines the unique entrepreneurial challenges created by conflicting public policy, including the absence of the banking industry and the competition with an existing black market. This case explores the way public policy shapes industry growth and opportunity and applies a Porter’s Diamond Theory analysis to compare the cannabis industry in Canada and the state of Oregon to determine strategic advantage in a global market. These tools can then be used to stand in the CEO’s shoes as he considers his options regarding new product introduction or moving operations to another country.