Amazon.com

Jeff Bezos quit his well-paying job at hedge fund D.E. Shaw in 1994 to sell books online. His boss thought he was crazy. Bezos drove from New York to Seattle while his wife drove — he typed the business plan on a laptop in the passenger seat. He made the decision using a "regret minimisation framework": at 80, he knew he'd regret not trying far more than failing.

Amazon went public in May 1997 at $18 per share. Barron's ran a cover story calling it "Amazon.bomb," arguing the company could never generate enough profit. Amazon lost money for nine consecutive years. Bezos kept investing in fulfilment, technology, and selection. The analysts were right about the losses — and completely wrong about everything else.

Amazon Web Services launched in 2006 as an internal tool to help Amazon's own engineers deploy infrastructure faster. The company realised other businesses needed the same thing and opened it to the public. AWS is now responsible for the majority of Amazon's profit, despite being a fraction of its revenue. It is the most profitable cloud business in history.

Jeff Bezos stepped down as CEO on July 5, 2021 — exactly 27 years after founding the company — handing over to Andy Jassy, who had built AWS from scratch. Bezos announced plans to fly to space on Blue Origin the same day. His net worth at the time was approximately $200 billion.

Amazon invested up to $4 billion in Anthropic in 2023, securing preferred cloud provider status and deploying Claude across AWS Bedrock. By April 2026, over 100,000 businesses were running Claude on Amazon Bedrock. AWS was growing at 17% annually in 2025, crossing $100 billion in annualised revenue. The company that had started by selling books online had become the infrastructure provider for the AI revolution — and was charging every major AI company for the compute to run it.