Chaos is generally referred to in mathematics as a kind of nonlinear dynamic process (Krakauer et al., 2019). The most significant feature of chaos is that a tiny change in the initial conditions can result in a much bigger, unexpected change in the final outcome (Churchill & Bygrave, 1990). The same phenomena happens in entrepreneurial and innovative activities, especially in the context of digital economy organized by a ubiquitous network of digital technology. The analogy has interested scholars in exploring the common endogenous features in complex systems. this chapter describes the generalized characteristics of innovation and entrepreneurship driven by digital technology from the perspective of chaos and complexity science, and then proposes research topics that deserve further study in management science.