Jeff Bezos recalls toughest moment from Amazon’s early days

Jeff Bezos may now preside over one of the most valuable companies in the world, but the Amazon founder says his toughest ordeal came long before the company became a global powerhouse.

Speaking at New York’s DealBook Summit last year, Bezos reflected on the grueling process of raising Amazon’s earliest funding in 1995, describing it as the most difficult challenge of his career.

At the time, Amazon was little more than an idea built around selling books online, a concept that many investors struggled to understand.

Bezos recalled holding roughly 60 meetings with potential angel investors in an effort to secure his first million dollars.

The overwhelming majority ended in rejection, with about 40 investors ultimately turning him down after multiple discussions.

Bezos said the process was emotionally draining, not only because of the repeated “noes,” but also due to the effort required for each pitch.

He offered investors a 20% stake in Amazon at a $5 million valuation and eventually convinced around 20 individuals to invest approximately $50,000 each.

“People would ask, ‘What’s the internet?’” Bezos recalled, noting that few understood the World Wide Web or its commercial promise.

He also admitted that his unusually candid approach may have scared investors away.