Today, Amazon’s market cap is hovering around $2.2 trillion, and founder Jeff Bezos is one of the world’s richest men, worth nearly $219 billion. Plus, Amazon just snagged the top spot on the Fortune 500 from Walmart, dethroning it from a 13-year reign.
But about 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.
A version of this story was published on Fortune.com on December 15, 2025.
More on Amazon:
- Amazon takes the No. 1 spot on the Fortune 500, ending Walmart’s 13-year run
- Amazon exec says the most important lessons from Jeff Bezos were the 16 leadership principles he once dismissed as cultlike
- Larry Ellison and Jeff Bezos have seen more than $66 billion swiped from their net worths since the start of this year as AI-driven slump sees tech billionaires’ wealth free-fall
