Jeff Bezos Says The 'Hardest Thing' Was Landing Amazon's First Million, Says He Warned Potential Backers Of A '70% Chance' They'd Lose Their Money

Jeff Bezos says the toughest test of his career wasn't building a trillion‑dollar tech empire — it was scraping together Amazon's first million dollars.

What Happened: Speaking at The New York Times DealBook Summit in December 2024, the Amazon founder recalled 1995, when "to raise the first $1 million of seed capital for Amazon, I [Bezos] sold 20% of the company at a $5 million valuation… to 22 angel investors, roughly $50,000 each." 

He said it took 60 pitches to secure those checks. "The 40 ‘no's were hard‑earned ‘no's… The whole enterprise could have been extinguished then." Potential backers' first question: "What's the Internet?" Bezos even warned prospects that there was a "70% chance they would lose their investment."

“It was the hardest thing I've ever done," he added.

The gamble aged well. Amazon's market capitalization hovers near $1.99 trillion today, according to TradingEconomics, making that early 20 percent stake, had it survived dilution, worth roughly $400 billion. A single $50,000 slice would be about $18 billion.

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Bezos told moderator Andrew Ross Sorkin that the ordeal shaped Amazon's culture of persistence. "Conviction matters," he said, adding that overcoming early skepticism was "the hardest thing I've ever done."

Amazon, launched from a Seattle garage to sell books online, now spans cloud computing, streaming, groceries and artificial intelligence. Yet Bezos noted that success began with convincing two dozen believers when the Internet itself was a curiosity. "If those 22 had said no," he said, "none of this would exist."

What To Know: Bezos, in the same talk, told DealBook that founders often "overestimate risks and underestimate opportunities," so he deliberately tilts the other way. What looks like confidence, he said, is really "compensating for that human bias." Thinking small, he added, is "a self‑fulfilling prophecy" — act modestly and your results will match.

Bezos, at the time, also sounded upbeat about Donald Trump's second term as president, saying lighter regulation could spur business. He urged Washington to pair spending restraint with faster growth, aiming for 3‑5 percent annual GDP gains so the national debt rises more slowly than the economy.

Image via Shutterstock

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