There's a moment in every entrepreneur's story where everything could have gone differently. For Amazon.com, Inc. (AMZN) founder Jeff Bezos, that moment happened during a long walk through Central Park with his boss at a Wall Street firm.

The Walk That Almost Stopped Amazon

Speaking in a 2001 interview with the Academy of Achievement, Bezos described approaching his boss with an unconventional career update: he wanted to quit and start an online bookstore. His boss didn't laugh him out of the room. Instead, he suggested they take a walk to talk it through.

That walk lasted nearly two hours.

"The conclusion of that was this," Bezos recalled. "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.'"

It's the kind of advice that sounds reasonable, even generous. You have stability, a career trajectory, money coming in. Why risk it all on something as uncertain as selling books on the internet?

Thinking It Over For 48 Hours

Bezos said his boss encouraged him to sleep on the decision for 48 hours before making any final moves. It wasn't just a polite suggestion. Bezos had real stakes on the line, including forfeiting his annual bonus if he left midyear.

The decision forced him to think beyond the immediate financial hit. He developed what he later termed a "regret minimization framework," a mental exercise designed to strip away short-term noise and focus on what would matter decades later.

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

The Real Risk Wasn't Failure

When Bezos played out that scenario in his head, the answer became clear. Failing at a startup wouldn't haunt him. What would keep him up at night was never trying in the first place.

"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 of the leap, even though it meant abandoning financial security for what many at the time considered a far-fetched idea.

From Garage Experiments To Wall Street Engineer

Bezos wasn't new to taking things apart and building them back up. As a kid, he turned his parents' garage into a makeshift lab, assembling electrical devices all over the house. One of his first creations was an electric alarm for his bedroom, specifically designed to keep his younger half-siblings out.

He studied computer science and electrical engineering at Princeton University, graduating Summa Cum Laude in 1986. From there, he landed on Wall Street as a computer engineer before deciding to start Amazon on July 4, 1994.

The company began as an online bookstore. After going public in 1997, Amazon's stock surged nearly 40 times, pushing Bezos' net worth above $12 billion. But when the tech bubble burst, his holdings dropped to under $2 billion by 2001.

Where Things Stand Now

Bezos, who turns 62 on January 12, currently has a net worth of $267 billion, placing him third on the Bloomberg Billionaire Index. Amazon now has a market cap of $2.63 trillion.

It's hard to imagine that trajectory starting any other way than with that two-hour walk and a decision to prioritize long-term regret over short-term comfort.