Chegg: When a Subscription Moat Met Free AI
Chegg was a US-based online education company that built its business around paid academic support — textbook rentals, homework help, step-by-step solutions, and tutoring for university students. Founded in 2005 and listed on the New York Stock Exchange in 2013, Chegg became a staple of the US student ecosystem during the 2010s.
At its peak in 2021, Chegg was valued at over $14 billion, powered by subscription growth, pandemic-era remote learning, and the belief that education support was a durable, high-margin recurring revenue business. Investors saw a classic SaaS-style model: sticky users, predictable cash flow, and pricing power.
They were wrong.
Why the Money Was Lost
Chegg didn’t fail slowly — it was disrupted almost overnight.
Generative AI made its core product obsolete. Tools like ChatGPT offered instant, free explanations across almost every subject Chegg monetised.
The value proposition collapsed. Why pay monthly for answers when AI could explain concepts conversationally, repeatedly, and at zero cost?
Students churned fast. Chegg’s subscribers were young, price-sensitive, and highly adaptive. Loyalty evaporated.
Brand and content moats proved illusory. Years of curated solutions were no defence against probabilistic, on-demand AI reasoning.
Pricing power vanished. Chegg couldn’t raise prices, and discounts only accelerated margin erosion.
Growth assumptions broke instantly. What looked like a linear decline was actually a structural demand cliff.
Crucially, this was not a recession story, nor a cost-inflation story. It was technological substitution — the most brutal kind. The product didn’t get worse; it simply became unnecessary.
The Market Reaction
From its 2021 highs, Chegg’s share price fell by over 95%, wiping out billions in market value. Revenues stagnated, guidance was repeatedly cut, and the company was forced into layoffs, restructuring, and strategic retreats. The stock chart didn’t show panic — it showed a long, grinding realisation that the business model no longer had a future moat.
Chegg still exists, but as a shadow of its former self — a reminder that even profitable, subscription-based platforms can be rendered fragile when the underlying problem they solve disappears.
The Lesson
Chegg wasn’t destroyed by poor management, excessive debt, or macroeconomic weakness. It was destroyed by abundance.
When answers became free, instant, and conversational, the idea of paying for them collapsed. In that moment, Chegg joined a growing list of companies that didn’t just lose customers — they lost relevance.
This wasn’t a bad quarter.
It was the end of an era.









