This historically-informed study examines how entrepreneurship has taken hold and developed different forms during different time periods, particularly its most recent manifestation of so-called unicorns (VC-backed private companies with billion dollar valuations). Using the intersection of history and biography as a theoretical lens, we compare companies from two analytically distinct eras—the dot.com era (1985-2000) and the unicorn era (2000-2015)–to determine when, why, and how, the form of entrepreneurship as practiced in society changes, and with what effects. This historiographic approach reveals diverse generational units of entrepreneurs and prompts a rethinking of entrepreneurial opportunity as a historical construct.