This chapter deals with the entrepreneurial key element of the “investor pitch” and examines by means of a combination of speech-production and perception experiments if and to what extent the acoustic parameters of a charismatic tone of voice can be improved by rehearsing a pitch in a virtual presentation setting in comparison to a traditional setting in which speakers rehearse their pitch alone in a quiet room. About 5000 measurements were taken from the elicited investor pitches, and the acoustic results were cross-validated by 31 listeners who judged excerpts of all pitches in terms of perceived speaker charisma. On this basis, this chapter provides empirical evidence that the traditional rehearsal setting degrades the charismatic tone of voice of a speaker with each new repetition of the investor pitch. Rehearsing in a virtual reality (VR) environment, on the other hand, counteracts this erosion effect and even results in a gradual improvement of the speaker’s charismatic tone of voice. Initial findings also indicate that this positive VR effect persists when speakers return from the virtual to the traditional rehearsal setting. The results are discussed with respect to their implications for practitioners and for further research and development of digital learning technologies in entrepreneurship education.