Lyft's David Risher: From Microsoft to Amazon, a Bold Leap of Faith

In the mid-1990s, David Risher made what seemed like an unusual career move, departing from Microsoft, a corporate titan with nearly $8.7 billion in yearly sales, to take a role at Amazon, then an obscure online bookseller.

Reflecting on this decision, Risher, the current chief executive officer of Lyft, acknowledged during a session of the Fortune Leadership Next podcast on September 30 that the choice to leave wasn't entirely logical. Between 1997 and 2002, he was Amazon's senior vice president for U.S. retail.

Bill Gates himself attempted to dissuade Risher from leaving, pointing out his successful tenure at the tech behemoth. At Microsoft, Risher had been instrumental in developing Access, the company's pioneering database software.

During that era, Gates, who was the world’s wealthiest individual with an immense fortune as noted by Forbes in September 1996, found it baffling that Risher would abandon Microsoft for a fledgling internet venture like Amazon, which was recording minimal revenue shortly after its establishment by Jeff Bezos.

"You're doing well here, and you're going to leave for some unheard-of internet bookstore? That might be one of the most nonsensical decisions I've ever encountered," Risher quoted Gates. Despite his surprise, Gates didn't change Risher's mind as Amazon's founder had laid out an irresistible proposition.

Amazon's Promising Future According to Bezos

Risher's initial interaction with Bezos took place over a phone conversation a year before he joined Amazon, where Bezos was conducting a background check for a prospective employee.

Risher was taken by Bezos' inquisitive nature and the fact that the company’s leader personally devoted time to such matters, sharing this insight with journalist Danielle Newnham.

By 1996, Risher decided to actively pursue a position at Amazon, driven by two compelling aspects of Bezos' personality and vision. Bezos' intense focus on enhancing customer experience stood out to Risher.

"The prospect of positively impacting the lives of countless customers was very compelling," Risher remarked to Newnham.

Another compelling aspect of Bezos' proposal was his assurance that Amazon was on the path to becoming a major tech powerhouse.

Although the company was modest at the time, Bezos anticipated a diversified future beyond books, expanding into various product lines, which was part of his grand plan.

Bezos assured Risher, "If we execute correctly, we could be a billion-dollar business come the year 2000." This bold prediction was crucial in convincing Risher.

An Alluring Adventure at Amazon

Bezos' vision resonated with Risher, who saw the potential for massive, rapid expansion as incredibly appealing.

"How often does one have the chance to be part of a company at the nexus of technology and culture, aiming to build a billion-dollar venture?" Risher mused to Fortune.

They outstripped Bezos' optimistic forecast, with Amazon achieving $1.6 billion in revenue in 1999. Risher played a significant role, being one of the first 40 employees, tasked with broadening Amazon's product range to include items like music and toys.

By the time he left to teach business at the University of Washington in 2002, Amazon's sales had soared to $3.9 billion.

Now leading Lyft since 2023, Risher, at 60, continues to draw leadership inspiration from his time with Gates and Bezos, reminiscing fondly about the exhilarating beginnings of Amazon.

"That period was like riding a rocket ship—a thrilling venture. Building something unprecedented at such scale was incredibly exciting," Risher reflected.