Amazon.com vs Alibaba

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.

Jack Ma graduated from Hangzhou Teacher's Institute in 1988 after failing China's university entrance exam twice. He applied for 30 jobs and was rejected from all of them. When KFC opened in Hangzhou, 24 people applied. 23 were hired. Ma was the only one turned down. He applied to Harvard ten times and was rejected every time. He became an English teacher earning $12 a month. He later described the rejection years as the best education he ever received.

Jack Ma founded Alibaba in his apartment in Hangzhou in February 1999 with 17 friends and colleagues. He gave a speech — later called the "Crazy Jack Ma Speech" — telling them they were starting a company that would compete with American internet giants. He warned them it would be hard, that they might fail, and that they should not expect to get rich quickly. Several people in the room were crying. Within fifteen years, Alibaba would be worth more than $800 billion.

Alibaba went public on the New York Stock Exchange on September 19, 2014, raising $25 billion — the largest IPO in history at the time. Jack Ma, the English teacher who had been rejected from KFC, became the richest person in China. SoftBank, which had invested $20 million in Alibaba in 2000, saw that investment become worth $60 billion on IPO day alone.

In October 2020, Jack Ma gave a speech at a financial conference in Shanghai criticising Chinese financial regulators, comparing state-owned banks to "pawnshops." Two days before Ant Group was set to complete the world's largest IPO at $37 billion, Chinese regulators suspended it. Ma disappeared from public view for three months. When he reappeared, he had given up effective control of both Alibaba and Ant Group. The episode was the most dramatic demonstration of regulatory power over private enterprise in modern Chinese history.

In early 2025, Jack Ma began reappearing at Alibaba's Hangzhou headquarters, taking a direct role in strategy for the first time since 2020. His return coincided with a softened regulatory stance from Beijing and Alibaba's aggressive pivot to AI — pledging ¥380 billion ($52 billion) in cloud and AI infrastructure over three years. Alibaba's stock surged over 90% in 2025. The company that had been kneecapped by a speech was back — powered by AI, led once again by the man who had started it all with $12 a month and a refusal to accept rejection.