The story
Founding and early growth
Chegg originated as Cheggpost, a Craigslist-style message board for Iowa State University students launched in October 2000 by Josh Carlson, Mike Seager, and Mark Fiddleke. Carlson teamed with Osman Rashid, an avid user of the site who recognized its potential to disrupt the textbook market, and together with Aayush Phumbhra they incorporated the company in 2005, initially offering scholarship searches, internship matching, and college application advice. That same year, the founders purchased 2,000 textbooks and launched Textbookflix.com, a rental service modeled on Netflix.
After Carlson's departure in February 2006, Phumbhra and Rashid rebranded the service, launching it as Chegg in December 2007 with Rashid as CEO. The name Chegg is a combination of the words chicken and egg, and references the founders' catch-22 feeling of being unable to obtain a job without experience, while being unable to acquire experience without a job.
Growth was rapid: revenues exceeded $10 million in 2008, and the company surpassed that figure in January 2009 alone. That June, former Ask.com and Match.com CEO Jim Safka replaced Rashid as CEO, and in November 2009 the company raised $57 million in a financing round led by Insight Venture Partners.
Expansion and IPO
Dan Rosensweig, formerly CEO of Guitar Hero, took over as CEO in February 2010 and began shifting Chegg from a textbook rental business toward a broader digital learning platform. Under his leadership, Chegg added course selection and homework help features in 2011, raised an additional $25 million from 17 investors in 2012, and pursued an aggressive series of acquisitions (see below).
In November 2013, Chegg went public on the New York Stock Exchange at $12.50 per share, raising $187.5 million and achieving a valuation of $1.1 billion. The following year, Chegg partnered with Ingram Content Group to handle its physical textbook distribution, allowing the company to focus on digital services.
In April 2017, Chegg and Pearson Education entered a partnership whereby Pearson made 50 textbooks available exclusively for rent on Chegg. The relationship soured, however, and after the partnership ended in May 2021, Pearson sued Chegg for copyright infringement, alleging that Chegg had profited from selling answers to end-of-chapter questions in Pearson textbooks.
AI disruption and restructuring
In June 2021, Chegg launched Uversity, a platform for professors and educators to share content. The company's core business, however, came under severe pressure from generative AI. In May 2023, Chegg acknowledged that ChatGPT had become a serious competitor, and its stock fell 38% in a single day; the company responded by announcing Cheggmate, its own AI-powered platform.
Rosensweig stepped down as CEO in June 2024 after 14 years, becoming executive chairman, and was succeeded by longtime Chegg executive Nathan Schultz. The transition did not arrest the company's decline. By late 2024 Chegg was steadily losing subscribers, and in February 2025 the company sued Google, alleging that its AI Overviews feature diverted traffic away from Chegg's website.
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Chegg cut approximately 248 employees, or 22% of its workforce, in May 2025. In October 2025, after a year-long strategic review conducted with Goldman Sachs that considered a sale and a go-private transaction, the board concluded that Chegg would remain a standalone public company. Alongside that announcement, Chegg laid off a further 388 employees (45% of the remaining workforce) and shifted its focus toward business-to-business skilling model, including professional language learning, workplace readiness, and AI-related skills courses. Chegg Skilling generated $68.7 million in revenue in 2025. Rosensweig returned as CEO, replacing Schultz, who became an executive adviser.
Chegg received notice from the New York Stock Exchange in December 2025 that its average closing share price had fallen below the exchange’s $1 minimum. The company regained compliance with the minimum share-price requirement on June 1, 2026, but received a second noncompliance notice in July after its average closing share price again fell below $1 over a consecutive 30-day trading period. The company was given six months to regain compliance.
In September 2026, Chegg repaid at maturity the remaining $33.9 million aggregate principal amount of its 0% convertible senior notes due that month, leaving the company with no outstanding debt.
Acquisitions
Chegg acquisitions include:
CourseRank (August 2010), a website for rating and reviewing courses, disabled in 2014.
Cramster.com (December 2010), a provider of online homework help.
Notehall (July 2011), an online marketplace for class notes.
Zinch (September 2011), a scholarship search service for high school students and college recruiters.
3D3R (November 2011), software company, to develop its digital textbook product, kickstart its mobile product group, and open an engineering office in Rehovot, Israel.
InstaEDU (June 2014), an online tutoring platform obtained for $30 million, which was renamed Chegg Tutors.
Internships.com (October 2014), for $11 million.
Imagine Easy Solutions (May 2016), a provider of online bibliography and research tools, for $42 million.
RefME (February 2017), a free citation management tool available on web, iOS and Android. It was shut down on March 7, 2017, and user accounts were transferred over to CiteThisForMe.
Cogeon GmbH (October 2017), a German mathematics education provider, for €12.5 million in cash.
WriteLab (May 2018), which uses artificial intelligence to analyze text and suggest improvements, for $15 million.
StudyBlue (July 2018), an online flashcard tool, for $20.8 million.
Thinkful (September 2019), an online coding, design, and data science school for $80 million cash, plus $20 million in cash or stock based on performance.
Busuu (November 2021), a computer-assisted language learning service, for $436 million in cash.
From Wikipedia’s article on Chegg, shared under CC BY-SA 4.0.8