Amazon founder Jeff Bezos: I was a little naive and told all my investors they had a 70% chance to lose their money

Early Struggles and Honest Pitch

Amazon founder Jeff Bezos spoke openly about the tough early days of his company at the DealBook Summit with Andrew Ross Sorkin. He said raising the first million dollars of seed capital was one of the “hardest things” he had ever done. Back in 1995, Amazon was just an idea in his head, a plan to sell books on the internet. At the time, the internet was still new to most people, and the concept of online shopping was unfamiliar.

Bezos admitted he was “a little naive” when pitching investors. He told everyone he met that there was about a 70 percent chance they would lose their money if they backed Amazon. He now sees that as straightforward honesty, but back then it may have hurt his chances to win support.

Raising Seed Capital Was Tough

In his push for seed funding, Bezos offered 20 percent of Amazon at a $5 million valuation. He met with roughly 60 potential angel investors, hoping to raise $1 million. Out of those meetings, 40 investors said no. Some of the “noes” weren’t quick or casual refusals. They were hard-earned, with long discussions and repeated meetings before investors decided against putting money in.

Eventually about 20 investors agreed to invest about $50,000 each. Those early backers believed in his idea even when most people did not. Without their support, Bezos said, “the whole enterprise could have been extinguished then.”

Bezos called those early meetings some of the hardest of his life. Investors didn’t just question his numbers or projections. Many asked what the internet was, because so few truly understood it yet. That uncertainty made the pitch even harder, since his business model depended entirely on internet commerce.

The Hardest Meetings in Bezos’ Life

Bezos said the experience left a lasting mark on how he thinks about business and risk. He sees raising that first million as a lesson in persistence and conviction. Even though he was honest about the risks, he kept pushing until he found the right people to believe in his vision. Without persistence, Amazon might never have reached the size it is today, with a market value vastly larger and more influential than anyone expected in 1995.

Looking back now, Bezos frames his candid approach as both a strength and something he might rethink. Telling investors their money was likely to be lost was rooted in realism and caution. But it may also have discouraged some potential backers who were otherwise interested. That honesty helped him stay true to his vision, but it came at the cost of many rejections.

What Early Investors Asked About

One common question from early investors was simple and revealing: “What’s the internet?” At that time few people truly grasped its potential. Books were familiar, but buying them online was not. Bezos found himself explaining the basic concept of the internet before he could even make his case for an online bookstore. That hurdle, more than anything else, showed how ahead of his time he was.

Despite the early skepticism, those first investors paved the way for what Amazon would become. Their willingness to take a risk on something unfamiliar helped Bezos build a company that today touches everything from retail to cloud computing and beyond.

Why Naivety May Have Helped Bezos

Bezos now reflects that telling people there was a 70 percent chance they would lose their investment might have been naive. But he also thinks that being honest helped shape Amazon’s culture of transparency and long-term thinking. The early setbacks taught him that not all good ideas are immediately understood, and that belief in a vision often outlasts early doubt.

His candid approach and persistence helped turn Amazon into a massive tech force, even if it meant facing many rejections at first. That early grind, meeting after meeting, now feels like an essential part of the story of how one of the biggest companies in the world got started.