This chapter develops a thesis which is twofold: On the one hand, there are tipping points in our founder cultures, according to which both the way firms are built and the specific founder personalities can change fundamentally. On the other hand, it is argued that we face two global (“global” in the mathematical sense according to which we refer to properties that are not related to a specific environment.) tipping points in our startup cultures. The first, heralding Entrepreneurship 2.0, challenges a key characteristic of startup formations and of startup founders, namely that these activities and personalities are associated with a comparatively high level of risk-taking. In the era 3.0, by contrast, companies will no longer be established and run solely by human entrepreneurs, but in (a large?) part also by artificial intelligence (AI). In a later section of this article, I outline the requirements that AI systems must fulfill for qualifying for this era 3.0.