In the prelude to Amazon.com, Inc.’s emergence as a dominant force in e-commerce, Jeff Bezos faced a defining career crossroads during his tenure at a Wall Street firm. The contemplation of resigning from his secure position to initiate what would become Amazon began with a forthright conversation between Bezos and his superior that could have fundamentally altered the trajectory of the company.
During a 2001 interview with the Academy of Achievement, Bezos recounted approaching his manager to disclose his intention to start an online bookstore. The notion itself was not met with outright dismissal. Instead, his boss proposed they take a walk in Central Park, a stroll that extended to nearly two hours. It was amid this dialogue that his boss conveyed a nuanced perspective: while the idea held merit, it seemed more fitting for someone not already established with a comfortable job.
Reflecting on this counsel, Bezos noted the advice to take 48 hours to deliberate on the decision before quitting. This pause was designed to encourage a thoughtful appraisal of the long-term implications. At the time, Bezos enjoyed a stable career and was positioned to receive an annual bonus, which he would forfeit by resigning midyear. The weight of the decision was significant.
Central to Bezos’ framework for making this leap was what he later termed the "regret minimization framework." He conceived of projecting himself forward several decades, to age 80, and envisioning reflecting back to identify potential regrets. The motivation was to choose the path that would minimize future remorse.
Bezos articulated that failure was not the paramount risk. Instead, the true risk lay in never having tried to pursue the venture at all. He was confident that the regret of not attempting to realize his vision would be more burdensome than the possibility of failure. Supporting him in this endeavor was his then-wife MacKenzie Scott, who stood behind the decision despite the uncertainty engulfing the move.
Before the inception of Amazon, Bezos held the position of a computer engineer on Wall Street. His academic background includes graduating Summa Cum Laude from Princeton University in 1986 with degrees in computer science and electrical engineering. His fascination with technology was evident from childhood, exemplified by transforming his parents' garage into an experimental space and constructing electrical devices, such as an electric alarm to protect his bedroom from intrusion by his half-siblings.
Amazon was founded on July 4, 1994, initially as an online bookstore. Following its initial public offering in 1997, Amazon’s stock experienced exponential growth, increasing by approximately 40-fold. During this period, Bezos’ net worth escalated beyond $12 billion. However, the tech bubble crash resulted in a dramatic decline, reducing his holdings to under $2 billion by 2001.
Approaching his 62nd birthday on January 12, Bezos’ net worth currently stands at $267 billion, positioning him third on the Bloomberg Billionaire Index. Concurrently, Amazon holds a market capitalization of $2.63 trillion. According to Benzinga Edge Stock Rankings, Amazon ranks in the 75th percentile for Quality and the 54th percentile for Momentum among its peers, including Apple, Microsoft, and Meta.