Entrepreneurial intention research requires further examination of systemic relationships between constructs of comprehensive models that will more closely approximate the ontological realities of individuals. This research jointly examines relationships among basic individual values and constructs from the theory of planned behavior, entrepreneurial orientation, and entrepreneurial intention while accounting for multiple contextual factors. Situational factors are accounted for by random determination of mediators, examination of 23 model configurations, and use of quasi-random samples (e.g., respondents with different demographic factors from different organizations, industries, and regions) from two culturally and economically contrasting countries, the United States and India. Models were analyzed using PLS-SEM. Contrary to the “common view”—the idea that Western countries are individualistic and Asian and Latin American countries are collectivistic—individual personal focus values and passion relationships were stronger for India’s sample than for the United States. Contrary results were found for basic individual social focus values and subjective norms relationships. Results show a lack of stark disparities between the two country samples. Hence, it seems that between-country differences have been overemphasized, while more attention to context and to within-country variability is required. This study expands the entrepreneurial orientation nomological network by jointly considering basic individual values and TPB’s and EO’s constructs anteceding entrepreneurial intention and examining a large set of model configurations while accounting for multiple situational factors in two culturally and economically contrasting countries.