" I’m not so naive as to think that everybody always succeeds, right? I mean, half of Shakespeare’s stories are tragedies – right? "
- Michael J. Saylor

The quote suggests that it’s unrealistic to expect everyone to always succeed or have positive outcomes. The speaker acknowledges the existence of failure and adversity by referencing Shakespeare's tragedies, which often depict characters facing significant challenges and negative endings. This comparison underscores a fundamental aspect of human experience and storytelling.

At its core, the quote speaks to the nature of life's unpredictability and the inevitability of encountering obstacles and setbacks. Just as Shakespeare’s tragic plays illustrate the harsh realities of the human condition, the speaker implies that it is naïve to believe in perpetual success or smooth sailing for everyone. The reference to half of Shakespeare's works being tragedies serves not only to highlight a literary truth but also to remind us of the cyclical nature of life, where both triumph and tragedy coexist. This perspective encourages resilience and acceptance, reminding individuals to prepare for adversity rather than expecting constant success.

Michael J. Saylor is an American businessman known for his work in technology and finance. He founded MicroStrategy Incorporated, a company that specializes in business intelligence software and analytics platforms. Beyond his professional achievements, Saylor is also recognized for his philanthropic efforts and contributions to the tech industry through education and advocacy. His quote reflects a blend of pragmatic realism and philosophical insight, which aligns with his role as an influential figure in business and technology.