In February 2021, Chegg was worth $14.5 billion. It was an online learning platform - students paid $19.95 a month for homework help, exam prep, problem-solving. It was profitable, it was popular, it was the future of education.

Then, on November 30, 2022, ChatGPT launched.

Today Chegg is worth around $115 million. A 99% collapse in under four years. The CEO admitted it himself in May 2023: AI is negatively impacting our ability to acquire new customers. The stock dropped 48% in a single day.

By early 2025, subscriber numbers had fallen 31% year-on-year - down to just 3.2 million users. Revenue dropped 30%. Two waves of mass layoffs followed: 248 employees (22%) in May, then another 388 (45%) in October. Half a company - deleted with a few clicks.

Chegg tried to fight back: it launched its own AI assistant CheggMate. But students already had Claude, GPT-4, Gemini - free and better. Google started showing AI answers directly in search results, bypassing Chegg entirely. The traffic vanished.

This is not just the story of one failed business. This is a warning. Every industry that relies on a middleman role between people and information - education, legal services, consulting, even journalism - needs to ask itself the same question: Can AI do our job better and for free? If the answer is partly yes, Chegg's numbers show where that road ends.