Great Transformations like the Digital Transformation and Sustainability Transformation, their challenges and their consequences for society are increasingly discussed in theory and practice. In this context, especially the issue of dealing with fundamental and profound changes in economy, politics and society is coming to the fore. In countries with liberal democratic systems such as Germany, an entrepreneurial mindset is granted an important role in dealing with these transformations in a proactive and formative way. Thus, the issue as to how more entrepreneurial individuals and organizations—and therefore more “out of the box thinking”—can systematically be tapped and developed in Germany becomes essential. To this end, this chapter proposes a newly conceptualized interdisciplinary and integrative approach, which was distinctly designed for the addressing and winning of entrepreneurial individuals and organizations in a systematic and targeted manner. Because it is specifically tailored to the prevailing circumstances and structures in Germany, the approach emphasizes enlightened, voluntary and self-sustaining actions. Doing so, it offers an effective, but also legitimate way to address and win entrepreneurial personalities and organizations to contribute to actively shaping the Digital and Sustainability Transformation.