This study focuses on the differences in perceived conditions reported by Baby-Boomer (BB-er) and Generation X (G-Xer) entrepreneurs and the consequent strategies used by each group to respond to these perceived conditions at different points in four business development stages. Although there are more entrepreneurial-based characteristics attributed to G-Xers than to their predecessors, the BB-ers were involved in more entrepreneurial activities than G-Xers. To understand more thoroughly this inconsistency, the conditions perceived by entrepreneurs of different generations as threats imposed to their businesses were identified, examining each business stage separately. We base our empirical foundation on the research literature concerning the adaptive model (Chaffee, 1985), on studies concerning the adaptation of business capabilities to external environmental conditions, and on models of business development stages.