Jeff Bezos Once Faced A Dilemma Over Quitting His Job To Pursue Starting Amazon, His Boss Said This To Him During A Walk In The Park

Jeff Bezos once revealed that before Amazon.com, Inc. (NASDAQ:AMZN) ever existed, he had a candid conversation with his boss during a long walk in New York that could have stopped the company before it began.

A Two-Hour Walk That Nearly Changed Amazon's History

Bezos, speaking in an interview with the Academy of Achievement in 2001, recalled going to his boss while working at a Wall Street firm to explain his plan to start an online bookstore.

The idea itself was not dismissed.

Instead, Bezos said his boss suggested they take a walk through Central Park — a walk that lasted nearly two hours.

"The conclusion of that was this," Bezos said. "He said, ‘You know, this actually sounds like a really good idea to me, but it sounds like it would be a better idea for somebody who didn't already have a good job.'"

48-Hour Pause And A Life-Defining Choice

Bezos said his boss urged him to think about the decision for 48 hours before quitting, advice that forced him to step back and consider the long-term consequences.

At the time, Bezos had a stable career and stood to lose his annual bonus by leaving midyear. The final decision, he said, came down to what he later called a "regret minimization framework."

"I wanted to project myself forward to age 80 and say, ‘OK, now I'm looking back on my life,'" Bezos said. "I wanted to minimize the number of regrets I would have."

Why Bezos Says Failure Wasn't The Real Risk

Bezos said he knew he would not regret trying — even if the venture failed. The real risk, he explained, was never attempting it at all.

"I knew the one thing I might regret is not ever having tried," he said. "I knew that would haunt me every day."

His ex-wife, MacKenzie Scott, was fully supportive, Bezos added, despite the uncertainty of leaving a stable career to pursue what many viewed as a risky idea.

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From Childhood Experiments To Wall Street Engineer

Bezos, once a computer engineer on Wall Street, founded Amazon on July 4, 1994, as an online bookstore.

Following the company's initial public offering in 1997, Amazon's stock skyrocketed nearly 40 times, pushing Bezos' net worth past $12 billion. However, after the tech bubble burst, his holdings were worth under $2 billion by 2001.

Bezos studied computer science and electrical engineering at Princeton University, graduating Summa Cum Laude in 1986.

His fascination with technology began long before college, when he transformed his parents' garage into a makeshift laboratory and built various electrical devices throughout the house.

One of his earliest projects was an electric alarm for his bedroom, designed to keep his half-siblings out.

Bezos, who will celebrate his 62nd birthday next week on Jan. 12, currently has a net worth of $267 billion, making him rank third on the Bloomberg Billionaire Index.

Meanwhile, Amazon currently has a market cap of $2.63 trillion.

According to Benzinga Edge Stock Rankings, Amazon ranks in the 75th percentile for Quality and the 54th percentile for Momentum. See how it stacks up against peers like Apple, Microsoft and Meta.

Photo Courtesy: Lev Radin on Shutterstock.com

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Disclaimer: This content was partially produced with the help of AI tools and was reviewed and published by Benzinga editors.