In the late 1990s, the textbook industry witnessed the rise of a new player that promised to revolutionize how students acquired their study materials. BIGWORDS emerged as a beacon of innovation, attracting significant investment and attention. However, the company’s journey was not a smooth sail; it faced the turbulent waters of the dotcom crash, leading to bankruptcy, before charting a course back to profitability.
The story of Kayak For Textbooks: How BIGWORDS Raised $80M, Went Bankrupt, Then Got Profitable Again is not just a tale of business ups and downs, but a testimony to resilience and strategic thinking in the face of adversity. Let’s delve into the history of BIGWORDS and uncover the strategies that brought this once-struggling company back to the shores of success.
How did BIGWORDS start in the textbook market?
BIGWORDS was founded with a vision to simplify the process of buying and selling textbooks. Jeff Sherwood recognized the need for a platform that could facilitate better deals for students and saw the potential of the internet as a means to achieve this.
The company quickly made a splash with its innovative search engine that helped users find the best prices for textbooks. Online textbook comparison was still a novel concept, and BIGWORDS was at the forefront of this burgeoning market.
Despite its early success, BIGWORDS was not immune to the challenges of a rapidly evolving tech landscape. The company had to adapt to changing consumer behaviors and technological advancements, striving to maintain its position in the online textbook market.
As students sought ways to reduce their educational expenses, BIGWORDS’ platform became increasingly relevant, offering price transparency in education and helping to democratize access to learning materials.

What challenges did BIGWORDS face during the dotcom crash?
Like many tech startups of its era, BIGWORDS was hit hard by the dotcom crash. The sudden shift in market sentiment led to a stark decrease in investment and consumer confidence.
The company, which had been on a trajectory of rapid growth, found itself struggling to secure the capital needed to sustain operations. The impact of the dotcom crash on BIGWORDS was severe, leading to considerable downsizing and a reassessment of its business model.
Despite the turmoil, BIGWORDS’ core mission remained intact. The team continued to seek ways to provide value to students, even amidst financial constraints.
How did Jeff Sherwood revive BIGWORDS after bankruptcy?
After the bankruptcy, Jeff Sherwood’s commitment to BIGWORDS did not waver. Jeff Sherwood’s unique approach to textbook pricing involved repurchasing the BIGWORDS brand and reimagining its business strategy from the ground up.
He focused on lean operations, minimization of overhead costs, and a reconceived platform that prioritized user experience and efficiency. This new iteration of BIGWORDS placed a strong emphasis on customer-centric services and profitability.
The turnaround was a testament to Sherwood’s belief in the company’s potential and his entrepreneurial spirit, which refused to let the BIGWORDS vision die.

What strategies is BIGWORDS using to achieve profitability?
Today, BIGWORDS stands as a profitable entity, thanks in part to its strategic reinvestment of revenue. The company operates with the agility of a startup, but the wisdom of a seasoned player.
- BIGWORDS eschews traditional marketing in favor of word-of-mouth referrals and organic growth.
- It maintains a lean operational model, which minimizes expenses without sacrificing quality or service.
- The platform’s algorithms constantly scour the internet, ensuring that students receive the best possible deals on textbooks.
The company’s role as an unbiased broker in the textbook industry is central to its success, helping students save on textbooks and fostering long-term customer loyalty.
How does BIGWORDS help students save on textbooks?
BIGWORDS’s platform aggregates prices from various sellers, presenting users with a comprehensive view of their options. This approach empowers students to make informed purchasing decisions, accessing savings that were previously obscured by the fragmented nature of the textbook market.
The company also educates users on the art of buying and selling textbooks, providing resources and tools that extend beyond mere price comparison.
The result is a service that not only saves students money but also time and effort, transforming the typically arduous task of textbook shopping into a more manageable and less daunting experience.
What are the main competitors of BIGWORDS in the market?
Despite its innovative platform and customer-centric approach, BIGWORDS operates in a competitive market. Major players like Amazon and Chegg are well-established entities with significant resources at their disposal.

However, BIGWORDS distinguishes itself through its specialized focus and commitment to neutrality. Unlike some competitors, BIGWORDS does not sell textbooks directly, which allows it to maintain an impartial stance in the price comparison process.
Other services such as BookScouter also vie for market share, but BIGWORDS’s robust search engine and user-friendly interface keep it competitive.
Frequently Asked Questions on BIGWORDS’ Textbook Services
How did BIGWORDS manage to recover after bankruptcy?
BIGWORDS reclaimed its foothold in the market by doubling down on its core mission of providing value to students. The company’s recovery strategy hinged on efficiency, scalability, and a relentless focus on its user base.
Through tactical financial management and a revamped platform, BIGWORDS not only recovered but also thrived, proving that with the right approach, a second act in business is more than possible.
What makes BIGWORDS different from other textbook services?
BIGWORDS sets itself apart with its dedication to price transparency and its role as an unbiased broker. Its service is designed to be user-friendly and comprehensive, offering a level of convenience and savings that is hard to match.
The company’s commitment to students and education, rather than direct sales, positions it uniquely in the market as a trusted adviser rather than a mere retailer.

What are the advantages of using BIGWORDS for students?
Students who use BIGWORDS benefit from a platform that simplifies the complexity of textbook shopping. The advantages include significant cost savings, time efficiency, and a single destination for price comparison.
Additionally, BIGWORDS offers alerts and mobile apps to keep students updated on pricing changes, ensuring they never miss a deal.
How does BIGWORDS ensure price transparency in its services?
Price transparency is at the heart of BIGWORDS’s business model. The platform employs sophisticated algorithms to ensure that students are presented with the most up-to-date and accurate pricing information available.
By aggregating prices from multiple sources, BIGWORDS guarantees that users have all the data they need to make an informed decision.
What future plans does BIGWORDS have for growth?
Looking to the future, BIGWORDS is focused on expanding its services and technological capabilities. The company plans to continue its mission of supporting students by enhancing its platform and exploring new ways to optimize the textbook purchasing experience.
Growth strategies may include partnerships, expanded offerings, and continued investment in technology to maintain a competitive edge in the evolving educational landscape.


