Amazon.com, Inc. vs Walmart Inc.

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.

Sam Walton bought a Ben Franklin variety store franchise in Newport, Arkansas in 1945 after returning from World War II. He grew the store's sales from $72,000 to $250,000 in three years. His landlord, recognising the store's success, refused to renew the lease and gave it to his son instead. Walton was forced to start over in a new town.

Sam Walton opened the first Walmart Discount City in Rogers, Arkansas on July 2, 1962. Walton's insight was geographic: he targeted small towns that other retailers ignored, where there was no competition. His pricing strategy was radical: he passed every possible saving on to customers, operating on margins that competitors considered impossibly thin. Walton believed that a smaller margin on a much higher volume would generate more profit than a higher margin on lower volume. He was right.

Sam Walton made a bet with his CFO in 1983: if the company achieved an 8% pre-tax profit, Walton would dance the hula on Wall Street. The company hit its target. Walton, then 65 years old, wore a grass skirt and danced the hula on Wall Street in front of television cameras. The story illustrated his management philosophy: celebrate success, keep employees engaged, and never take yourself too seriously. Walton drove a beat-up 1979 Ford pickup truck to his stores until his death in 1992.

Walmart became the largest retailer in the United States in 1990, surpassing Sears and Kmart. The company's logistics and distribution infrastructure gave Walmart cost advantages that competitors could not match. Walmart's information systems could track the sales of every product in every store in real time, allowing precise inventory management that reduced waste and ensured shelves were stocked. The technology investment was decades ahead of competitors.

Walmart reported revenues of approximately $648 billion for fiscal year 2024 — the largest revenue figure of any company in the world. Walmart employed approximately 2.1 million people in the United States, making it the largest private employer in the country. E-commerce, which had been Walmart's most persistently difficult challenge since the rise of Amazon, grew to represent approximately 15% of U.S. revenues — with Walmart's fulfillment centre network and curbside pickup model finally giving it a viable answer to Amazon's delivery capabilities. The man who had danced the hula on Wall Street in a grass skirt had built the largest commercial enterprise in human history.