This study focuses on the analysis and evaluation of various ways of generating progressive passive income. The relevance of the work is caused by the rapid development and implementation of information technology at all levels of the life of a contemporary person. For the financial market, digitalization is a particularly relevant trend - the financial sector does not require the binding physical mobility or consumption of values, but is based on the circulation and accounting of information that is easily converted, accumulated and processed using escalating progress of computer technologies. Moreover, in the financial sector, there is an active phase of automation and algorithmization of processes (algorithmic trading, robo-advising, smart contracts, etc.), which significantly increase operational efficiency. The analysis of the Russian market of robo-advisers and other methods of generating passive income in the era of “generation Y” showed how effective and relevant recommendations for managing savings and investment portfolios using new financial technologies become.