Amazon is a $2.38 trillion company today (as of Dec. 15, 2025), and founder Jeff Bezos remains one of the world’s richest people, worth about $235 billion. But Bezos says the toughest part of building Amazon didn’t come later with scale, competition, or logistics—it came at the very beginning: raising the first million dollars.
At the 2024 New York Times DealBook Summit, Bezos told Andrew Ross Sorkin that early fundraising in the mid-1990s was an outright grind—dozens of angel investor meetings that mostly ended the same way: no.
“I had to take 60 meetings,” Bezos said. “It was the hardest thing I’ve ever done, basically.”
60 meetings, 40 rejections, and a bet on a brand-new internet
Bezos said the pitch was simple on paper: he offered 20% of the company at a $5 million valuation, ultimately bringing in 22 angel investors at roughly $50,000 each—about $1 million total.
But he didn’t get there quickly. Out of those 60 meetings, 40 investors passed, and Bezos described many of those rejections as “hard-earned noes,” because they often came only after multiple conversations and a lot of effort.
Part of the struggle was timing. Bezos said he spent plenty of those meetings explaining the basics because many potential investors simply didn’t understand what the internet was yet—let alone why anyone would buy books over it.
Bezos’ pitch included a brutal warning
Bezos also admitted his own transparency may have contributed to the rejection rate.
“I would always tell people I thought there was a 70% chance they would lose their investment,” he said—adding that, in hindsight, he may have even been too optimistic about those odds.
Still, he argues the seed round was existential. Without those checks, the entire company could have died before it ever had a chance to prove the model.
“The whole enterprise could have been extinguished then,” Bezos said.
For anyone who wants the full context, Bezos begins recounting the seed-capital “gauntlet” at roughly the 34:30 mark in the DealBook interview, depending on the version/platform.