Alphabet Inc. (Google) vs Amazon.com, Inc.

Larry Page and Sergey Brin met at Stanford in 1995. By 1996 they had built a search engine called BackRub — named after its method of analysing backlinks. It ran on Stanford's servers and consumed so much bandwidth that the university repeatedly asked them to take it down.

Sun Microsystems co-founder Andy Bechtolsheim wrote Google a cheque for $100,000 in August 1998 after a brief demo in a Stanford parking lot. There was one problem: Google Inc. didn't exist yet. Page and Brin had to incorporate the company before they could cash it.

In 1999, Page and Brin tried to sell Google to Excite CEO George Bell for $1 million. Bell turned them down — the search was too good, it would send users away from Excite's portal too quickly. Bell later called it the worst decision of his career. Excite filed for bankruptcy in 2001. Google became worth more than $2 trillion.

When OpenAI launched ChatGPT in November 2022, Google declared an internal "code red." The company that had invented the transformer architecture — the technology that made ChatGPT possible — had published its research openly and was now scrambling to compete with the system it had inadvertently enabled. Google rushed Bard to market. It made a factual error in its first public demo. The stock dropped $100 billion in a single day. Google's search share fell from 80% to under 70% as users migrated to ChatGPT, Perplexity, and Claude.

In September 2025, a U.S. federal court ruled that Google had illegally maintained its monopoly in search, ordering the company to end exclusive distribution contracts with Apple, device manufacturers, and browser makers. The Apple deal alone had been worth approximately $20 billion per year to keep Google as the default search engine on Safari. The court stopped short of forcing Google to sell Chrome or Android, but the ruling was the most consequential antitrust action against a technology company since the Microsoft case of 1998. Google announced it would appeal. The case is expected to reach the Supreme Court.

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.