The cryptocurrency market is very young, volatile, and highly risky. By the end of 2020, a new bull run started, and the prices of several cryptocurrencies reached record-breaking highs. The factors affecting this rise of cryptocurrencies include the impacts of the COVID-19 pandemic, the economic crisis and the global increase in the inflation rate, as well as the gradual acceptance and adoption of cryptocurrencies by people worldwide. This exploratory research is focused on this last factor, i.e., using cryptocurrency and with it, the associated support of its ecosystem (e.g., mining, staking). A survey was carried out investigating the motivational factors and barriers to investment in cryptocurrency for Czech representatives of Generations Y and Z (18–42 years; n = 468). The geographic scope was nationwide, and quota sampling was used. Notably, this survey was carried out prior to the global COVID-19 pandemic outbreak, and it is thus not affected by the pandemic and its related economic impacts. The article investigates the dependency between the individual motivational factors and barriers from the perspective of the tendency to take risks (using the risk propensity scale), according to gender and representation of Generations Y and Z. The lack of information on this form of investment is considered as the main barrier to investment in cryptocurrency, with respect to sex and generations. Compared to that, a negative experience with investment in cryptocurrency constitutes the most minor barrier. Respondents that have a tendency to take risks are mostly put off by their lack of experience with investment in general. The main motivational factor for investment in cryptocurrency, with respect to sex and generations, is considered to be the speed of increase in cryptocurrency value. On the other hand, the least encouraging factor is the opportunity to use the high volatility of cryptocurrency for speculative trading. Interestingly, this factor mostly encourages respondents that do not have a tendency to take risks. The findings are discussed, along with the presentation of their implications for practice and the directions of further explanatory research.