In a candid reflection on career choices, Lyft CEO David Risher shared how Bill Gates once sharply criticized his decision to leave Microsoft for Amazon in 1996. According to Risher, Gates dismissed the move as “the stupidest thing,” a remark that has since become part of his professional journey. Despite the criticism, Risher’s leap into the then-nascent world of e-commerce helped shape his leadership philosophy, one he now applies in steering Lyft with a strong focus on customer experience.

Bill Gates’ Reaction to Risher’s Departure

At the time of Risher’s exit from Microsoft, the company was already a dominant force in the technology sector. Gates reportedly expressed disbelief at why anyone would leave such a secure and influential position for what was then an unproven online bookstore. His blunt assessment underscored how unconventional the decision appeared in the mid-1990s, when internet-based businesses were still viewed with skepticism.

A Bold Move Toward Amazon

Risher joined Amazon during its early years, long before it became one of the world’s largest companies. The choice reflected not only a willingness to take risks but also an interest in building something new from the ground up. While Gates questioned the wisdom of leaving Microsoft, Risher saw potential in Amazon’s vision and embraced the challenge of helping shape its growth trajectory.

Shaping Leadership Through Customer Focus

Looking back, Risher credits that career shift with influencing his management style today. At Lyft, he emphasizes a customer-first strategy similar to what he experienced at Amazon. By prioritizing user satisfaction and streamlining services, he aims to strengthen Lyft’s position in a competitive ride-sharing market. The lessons learned from taking risks and focusing on long-term value continue to guide his leadership approach.

An Unexpected Connection Between Gates and Bezos

Although Gates and Jeff Bezos took different paths during those years, their business interests have intersected in surprising ways since then. Both have invested in ventures beyond their original companies, including co-investing in a robotics startup. This convergence highlights how leaders who once diverged can later find common ground through shared innovation goals.

Lessons From a Controversial Career Choice

Risher’s story illustrates how decisions that may appear questionable at one moment can ultimately prove transformative. What was once labeled “stupid” by one of technology’s most influential figures became a pivotal step that shaped his career trajectory and leadership philosophy. His willingness to embrace uncertainty continues to resonate as he leads Lyft through its own period of reinvention and competition.

In retrospect, Bill Gates’ sharp critique underscores how unconventional choices often spark debate but can also lead to groundbreaking opportunities. For David Risher, leaving Microsoft for Amazon was more than just a job change—it was a defining moment that continues to influence how he approaches leadership and innovation today.