Entrepreneurs from generation to generation play a significant role in the business environment. Understanding this issue, especially by policymakers, is crucial for development. Misunderstanding or lack of interest often leads to inaction or incorrect decisions, creating barriers for current and potential entrepreneurs. Each generation evolves in its own era, and over time, each will fade and be replaced by a new, undefined generation. Policymakers would be interested in understanding these changes and providing targeted support for the needs of different generations, together with removing barriers that arise over time. This paper explores the differences in entrepreneurial motivation. As times change, entrepreneurs must adapt, leading to shifts in behaviour and personality. The study examines motivations for starting businesses across generations, considering variables such as business field, experience, age, sales, and type. Primary research in 446 business entities using the CAWI (computer assisted web interviewing) method tested generational differences in business motivation and participation. The statistical method, Cramer’s V, identified interrelationships between variables. Four hypotheses were tested, revealing an influence between necessity motivation and financial results, and a significant tie between generation type and company establishment. These findings could increase interest in this topic, which is expected to revive interest among researchers and policymakers. Simultaneously, the output increases awareness of this issue and brings knowledge to improve the quality of business conditions for all generations.