We investigate the entrepreneurial opportunities and ethical dilemmas presented by technological turbulence. More specifically we investigate the line between Baumol’s [J. Polit. Econ. 98 (1990) 893] productive (e.g. innovation), unproductive (e.g. rent seeking) and destructive (e.g. criminal) entrepreneurship through three examples of Internet innovation – spam (destructive), music file sharing (unproductive), and Internet pharmacies (potentially productive). The emergence of accessible Internet technologies, under present norms, has created the potential for all three entrepreneurial activities. Because of the propensity for self-serving biases (...) and for bending the rules, the need for creativity in overcoming obstacles and overall liabilities of newness, entrepreneurs are likely to challenge established industrial morals and laws. Unlike new entrants, incumbents must abide by the currently accepted norms, and thus suffer from “liabilities of oldness”. The challenge for new entrants is to change sociopolitical legitimacy, whereas incumbents need to defend the established norms. We discuss competitive and other issues that result from technological turbulence and innovation. (shrink)