Building legitimacy is one of the main challenges of every entrepreneur, especially transnational ones. The study has employed a combination of qualitative and quantitative methods including grounded theory and Borda count method to capture the perception of new transnational ventures (NTVs) from the sources of legitimacy for financiers and grant providers and the most important challenges of NTVs. The results from studying six Canadian-Iranian NTVs show that the most important challenges face NTVs to obtain legitimacy are "Insufficient understanding of Canadian business environment and business language", "Procuring funding", and "Building a network" Also, the most important perceived criteria of legitimacy are "the amount of investment in the business", "experience and background of the founder and director", and "credit history" of the owner(s). The contribution of the research is providing an examination of the intersection of NTVs and legitimacy. NTVs may use the results to manage their legitimacy.