How to Make Yourself Into a Learning Machine: A Startup Case Study


Hatched by Glasp

Sep 21, 2023

4 min read


How to Make Yourself Into a Learning Machine: A Startup Case Study


In the world of startups, success is not guaranteed. Many new businesses struggle to gain traction and find their niche in the market. However, there are always valuable lessons to be learned from those who have managed to turn their startups into thriving enterprises. In this article, we will explore the journey of Chegg, a company that started as a platform for college students but eventually became a leader in the textbook rental industry. We will also delve into the concept of becoming a learning machine and how it can benefit individuals in their personal and professional growth.

The GLEe Model - Get big, lead, and expand:

Chegg initially positioned itself as the "Craigslist for college students," but it wasn't until 2008 when they launched their textbook rental service that they gained significant traction. This move allowed them to provide overwhelming value to students who could rent textbooks for a fraction of the cost of buying new ones. Physical books offered advantages that eTextbooks couldn't match, such as the ability to highlight text using a marker. This unique selling point became a key factor in Chegg's success.

The DHM Model - Delight, Hard to copy, Margin-enhancing:

To further expand their offerings and cater to student needs, Chegg implemented the DHM model. They enabled students to buy and sell class notes, creating a "student graph" that included all the textbooks and content related to each course. By developing unique personalization technology using this data, Chegg was able to provide a more tailored experience for their users. However, not all experiments yielded immediate success. For example, their Facebook-style newsfeed based on student graph data failed to gain traction. Nonetheless, the company remained focused on their growth strategies.

The Rolling 4-Quarter Product Roadmap:

Chegg's brand experienced viral growth through their step-by-step solutions to textbook answers. This success prompted the expansion into other areas of homework help, including writing assistance, tutoring, and flashcards. This diversification led to the creation of a monthly subscription service called "Chegg Study." The company's product roadmap provided a high-level view of how these strategies would evolve over time.

How to Make Yourself Into a Learning Machine:

Transitioning from the startup world to personal growth, we explore the concept of becoming a learning machine. Simon, an individual seeking to optimize his own brain, treated his mind as technology infrastructure. He discovered that reading extensively was the best way to improve his skills and knowledge. By reading broadly, he gained a deep understanding of various subjects, allowing him to excel in his work.

The Importance of Going Deep and Wide:

When faced with the decision of whether to go deep or wide in his reading, Simon chose to read widely. He believed in being T-shaped, meaning having expertise in a specific area while also having a broad foundation of knowledge. This approach aligned with the philosophy of continuous learning and personal growth.

The Power of Highlighting and Note-taking:

Simon's core system for retaining information was highlighting important points while reading. He used a Kindle to highlight text and then transferred these highlights to Readwise, a tool that compiled all his annotations in one place. Additionally, Simon utilized flashcards through Anki to reinforce his learning. This habit of highlighting and note-taking proved to be highly impactful over time.

Building Connections Through a Zettelkasten:

To further enhance his learning process, Simon employed a Zettelkasten, a system that allowed him to connect different ideas and concepts. Instead of just memorizing individual facts, he focused on understanding how they interconnected. By organizing his notes in a plaintext editor with Markdown, Simon created a system that he could use for life.

Actionable Advice:

  • 1. Embrace Broad Reading: Just like Chegg expanded its services to cater to student needs, embrace the idea of reading widely. By exploring various subjects, you can gain a deeper understanding of the world around you and make connections across different domains.
  • 2. Develop an Effective Note-taking System: Whether it's highlighting important points, creating flashcards, or building a Zettelkasten, find a note-taking system that works for you. This will help you retain and connect knowledge, making your learning more impactful.
  • 3. Invest in Tools for Learning: Consider using tools like Readwise or Anki to enhance your learning experience. These platforms can help you organize and review information effectively, maximizing the benefits of your reading and note-taking habits.


The journey of Chegg teaches us the importance of adapting and evolving to meet the needs of our target audience. By implementing the GLEe and DHM models, the company was able to provide value and stand out in a competitive market. Similarly, in our personal lives, we can become learning machines by adopting strategies like broad reading, effective note-taking, and utilizing tools that enhance our learning experiences. Just as Chegg saw success by prioritizing growth, we too can achieve our goals by embracing continuous learning and personal development.

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