Can Chegg turn its fortunes around?

6/18/24 11:49AM

Like a student who starts the homework the morning that it’s due, digital education company Chegg is trying to adapt in the face of AI, with its April-appointed CEO announcing yesterday a major restructuring plan. The strategy includes cutting its headcount by 23%, as well as an ambition to build a “platform that incorporates artificial intelligence verticalized for education”. Investors appear to like the plan, with the stock currently up around 15% on the news, but some might be thinking it’s too little too late.

Textbook troubles

Renowned for providing homework help, Chegg is seeking to reinvent itself as students increasingly turn to free AI tools like ChatGPT for assistance, a trend that’s compounded a brutal 3 years for the company.

During the pandemic the company’s online platform became a lifeline for many as schools shut down and students "chegged" their way through homework and online tests by paying to access Chegg’s wide database of millions of textbooks to get the answers. Revenues at the company doubled between 2018 and 2020, turning Chegg into a business worth some $15 billion at its peak.

But, like so many pandemic-era trends, once schools opened back up, Chegg found itself losing ground. Shares lost an eye-watering 49% of their value in a single day in 2021. That misery was made worse when execs announced that ChatGPT's popularity was impacting customer growth — and its fortunes never really reversed. Once proclaimed “the most valuable edtech company in America” by Forbes, Chegg has lost some 98% of its peak market cap.

Max Knoblauch

Reddit bounces on report that it’s in talks with Google, OpenAI on fresh data-sharing deal

Reddit shares were down 5% in Wednesday trading before news that the company is in early talks to make its next AI content-sharing deals with Google and OpenAI sent them back up to roughly flat.

According to reporting by Bloomberg, Reddit is seeking a new data deal structure that includes dynamic pricing and would encourage the companies’ AI users to contribute to Reddit.

Reddit reportedly struck deals of $60 million per year with Google and OpenAI last year. The company scored $35 million in “other” revenue — which includes content licensing agreements — in its most recent quarter. That accounted for about 7% of the company’s overall revenue in the period.

“One of the things that we’ve learned, particularly through the data licensing deals is... how essential Reddit is to AI or LLMs as we know them and the next generation of search,” Reddit CEO Steve Huffman said on the company’s July earnings call. “And so I think a lot has changed over the last couple of years. Every variable has changed since we signed those first deals.”

Reddit Seeks to Strike Next AI Content Pact With Google, OpenAI

DO YOU EVEN SIP, BRO?

Adam Chandler

Hyunsoo Rim

VF Corp. is shedding its century-old workwear icon, Dickies, after years of struggle

The brand’s sales have been going backward for three straight years.

$100B

Nia Warfield

9/16/25

Alphabet’s YouTube said it’s paid out over $100 billion to creators, artists, and media companies over the past four years — cementing its place as one of the internet’s biggest talent magnets. The Google-owned platform, which turned 20 this year, credited connected TVs as a major driver of growth.

YouTube said the number of channels earning over $100,000 from TV screens has surged over 45% in the past year alone. Meanwhile, ad revenue for YouTube grew double digits in Q2 to $9.8 billion, topping the Street’s estimates.

Nia Warfield

9/16/25

Webtoon surges after Disney plans to invest and partner in digital push for brands like Marvel and “Star Wars”

Webtoon Entertainment shares jumped 36% in premarket trading Tuesday after Disney said it’s buying a 2% stake in the digital comics platform. The investment is part of a deal to bring Marvel, “Star Wars,” Pixar, and 20th Century Studios titles into a new streaming-style app run by Webtoon. The offering will launch in Q4 across the US and nine other countries.

“With a new platform that will combine our product and technical expertise with Disney’s full comic catalog, we’re giving new and longtime fans all over the world a new way to discover these legendary characters and stories,” said Junkoo Kim, founder and CEO of Webtoon Entertainment.

The platform is expected to host more than 35,000 titles, mixing archived comics with Webtoon originals. Disney+ perks could also be on the table, giving the service a natural tie-in to Disney’s broader streaming play.

The arrangement isn’t final yet: Disney’s stake and the platform details are still under negotiation. But with Webtoon’s ~155 million monthly active users, the partnership gives Disney a mobile-friendly channel for its comics while Webtoon gains the ultimate IP access.