‘I had to take 60 meetings’: Jeff Bezos says ‘the hardest thing I’ve ever done’ was raising the first million dollars of seed capital for Amazon

Today, Amazon’s market cap is hovering around $2.38 trillion, and founder Jeff Bezos is one of the world’s richest men, worth $236.1 billion. But three decades ago, in 1995, getting the first million dollars in seed capital for Amazon was more grueling than any challenge that would follow. One year ago, at New York’s Dealbook Summit, Bezos told Andrew Ross Sorkin those early fundraising efforts were an absolute slog, with dozens of meetings with angel investors—the vast majority of which were “hard-earned noes.”

“I had to take 60 meetings,” Bezos said, in reference to the entrepreneurial effort required to convince angel investors to sink tens of thousands of dollars into his company. “It was the hardest thing I’ve ever done, basically.”

The structure was straightforward: Bezos said he offered 20% of Amazon for a $5 million valuation. He eventually got around 20 investors to each invest around $50,000. But out of those 60 meetings he took around that time, 40 investors said no—and those 40 noes were particularly soul-crushing because before getting an answer, each back-and-forth required “multiple meetings” and substantial effort.

Bezos said he had a hard time convincing investors selling books over the internet was a good idea. “The first question was what’s the internet? Everybody wanted to know what the internet was,” Bezos recalled. Few investors had heard of the World Wide Web, let alone grasped its commercial potential.

That said, Bezos admitted brutal honesty with his potential investors may have played a role in getting so many rejections.

“I would always tell people I thought there was a 70% chance they would lose their investment,” he said. “In retrospect, I think that might have been a little naive. But I think it was true. In fact, if anything, I think I was giving myself better odds than the real odds.”

Bezos said getting those investors on board in the mid-90s was absolutely critical. “The whole enterprise could have been extinguished then,” he said.

You can watch Bezos’s full interview with Andrew Ross Sorkin below. He starts talking about this interview gauntlet for seed capital around the 33-minute mark.

What stands out in Bezos’s reflection is not just the number of rejections, but the emotional toll behind them. Each “no” represented weeks of preparation, travel, pitching, and follow-ups, often ending without a clear explanation. For many founders, that kind of repeated rejection can quietly drain confidence, making persistence harder with every meeting. Bezos’s experience highlights how resilience, more than raw brilliance, often determines whether an early-stage company survives long enough to succeed.

The context of the mid-1990s also matters. Venture capital as we know it today was far less accessible, and the idea of investing in a company with no physical storefront and no proven online market sounded reckless to many. Investors were trained to evaluate businesses with tangible assets and predictable demand, not abstract concepts tied to a technology most people barely understood. In that environment, skepticism wasn’t irrational—it was the default.

Jeff Bezos’s approach to transparency, while costly in the short term, likely helped establish trust with the investors who ultimately said yes. By openly acknowledging the risks, he filtered out anyone uncomfortable with uncertainty, leaving behind backers who genuinely believed in the long-term vision. That early alignment may have helped Amazon weather its later challenges, including years of losses and relentless reinvestment.

Looking back, the story serves as a reminder that even the most iconic companies were once fragile ideas held together by persistence and belief. Amazon’s early fundraising struggle underscores a simple truth: success narratives often erase the grind that came before. Behind every trillion-dollar company is a period where failure felt far more likely than success—and where giving up would have been the easiest option.