Jeff Bezos’ Hardest Challenge
Amazon founder Jeff Bezos recently shared that securing the company’s first $1 million was his most daunting task. Speaking at The New York Times DealBook Summit in December 2024, Bezos revealed that he had to pitch to 60 angel investors in 1995 before securing the necessary funding. He sold 20% of Amazon at a $5 million valuation, warning investors of a 70% risk of losing their investment.

Bezos emphasized that this early struggle shaped Amazon’s culture of persistence. “Conviction matters,” he said, highlighting the importance of overcoming initial skepticism. Amazon was founded in 1994 in a garage in Seattle, initially selling books online before expanding into various sectors like cloud computing, streaming, and artificial intelligence.
The Early Gamble
The early investment turned out to be highly successful. Today, Amazon’s market value is nearly $1.99 trillion. If the original 20% stake hadn’t been diluted, it would be worth about $400 billion. A single $50,000 investment in 1995 would now be worth around $18 billion.
Advice for Founders
Bezos also shared advice for entrepreneurs, cautioning that founders often “overestimate risks and underestimate opportunities.” He emphasized the importance of thinking differently and focusing on possibilities rather than dangers. What appears as confidence, Bezos explained, is actually compensating for human bias.
Perspective on Trump’s Second Term
During the conversation, Bezos also touched upon Donald Trump’s second term as US president. He suggested that lighter regulations could boost business activity and that Washington should focus on controlling spending while encouraging faster economic growth. The goal, Bezos said, should be to grow the economy by 3% to 5% annually, ensuring that the national debt grows more slowly than the economy itself.
Bezos’ insights offer valuable lessons for entrepreneurs and business leaders, highlighting the importance of persistence, conviction, and strategic thinking in overcoming challenges and achieving success.