This article assesses the development of Vancouver as an entrepreneurial region. Using data collected from commercial startup databases, we find that Vancouver produces more startups and receives more venture capital financing per capita than any other major Canadian city. However, we also find that Vancouver lags many U.S. cities on these same metrics. In light of our empirical findings, we explore whether differences in entrepreneurial activity between Canada and the United States are due to differences in the countries’ legal environments. We conclude that legal differences do not explain observed economic disparities, and that differences in entrepreneurial activity are due to broader institutional factors, including underdeveloped business networks, a lack of Canadian venture capital, and "brain drain" to the United States. Although some of these challenges are amenable to policy reform, others are beyond the scope of government intervention.