Business Education, Career Management, CEO, Entrepreneurship, Private Equity

Did Chegg get egged by AI?

“Video killed the radio star,” sang the Buggles in 1979. Fast forward to 2024, the British group formed in 1977 is still performing. Here’s a request for their next hit: how about “ChatGPT Killed Chegg”? After all, bassist Tom Horn foresaw this future, once predicting, “We had this idea that at some future point there’d be a record label that didn’t really have any artists—just a computer in the basement.” His prediction, it seems, was eerily accurate.

Chegg, once a dominant force in EdTech, revolutionized learning by offering affordable textbook rentals and subscription-based academic tools. Valued at over $12 billion during its peak, the company thrived during the pandemic, serving millions of students as remote learning surged. Yet, within just a few years, Chegg’s value plummeted by over 99%. The cause? The rapid rise of artificial intelligence.

Disruption by AI

The emergence of tools like OpenAI’s ChatGPT fundamentally changed how students sought academic help. Unlike Chegg’s subscription services, AI platforms offered instant, free solutions. By 2023, Chegg acknowledged losing subscribers, and by 2024, over half a million users had abandoned the platform. Although Chegg launched CheggMate, an AI-powered tool, it failed to compete with the widespread popularity of free alternatives.

Financial Struggles

Chegg’s financial performance deteriorated rapidly. In the third quarter of 2024, it reported a $212.6 million net loss and laid off 21% of its workforce. The company’s heavy reliance on a subscription-based model and slow adaptation to AI technologies left it vulnerable in a market transformed by innovation.

Lessons Learned

Chegg’s fall is a cautionary tale for businesses in tech-driven industries. It underscores the importance of anticipating disruption, diversifying revenue streams, and embracing innovation. Companies must stay agile and adapt quickly to new technologies or risk irrelevance.

The Path Forward

For Chegg to recover, it must focus on unique offerings, strategic partnerships, and rebuilding trust. Its future depends on its ability to innovate and redefine its role in education.

The story of Chegg is a stark reminder: in the age of rapid technological change, staying ahead isn’t optional—it’s essential.

Business Education, Career Management, Entrepreneurship, Personal Finance

Passive Income for an Active Life

The value of passive income has been recognized for years, but its importance was brought into sharp focus when a friend in his 50s confided in me. He admitted that neglecting to learn personal finance and build passive income streams is now holding him back from pursuing his entrepreneurial dreams. Despite decades of experience, he’s stuck. Why? He’s “paycheck dependent” and can’t afford to take risks.

Passive income isn’t just about money; it’s about time—the most valuable resource you have. Time, not money, is the real luxury. Ideally, one should start learning personal finance in their early teens. Data shows that the wealthy are more likely to invest in stocks, a key source of passive income. In 2020, 53% of the ultra-rich—the top 1% by wealth in the U.S.—owned stocks, compared to only 0.6% of those in the bottom 50%. Additionally, between 2006 and 2021, stock market indices in major economies such as the U.S., India, Brazil, China, and Japan appreciated by approximately 225%, 700%, 330%, 200%, and 160%, respectively. If we consider 2022 and 2023, the appreciation would be even greater.

The earlier you start investing and building passive income, the more control you’ll have over your time and your future. As I reflected on my friend’s situation, I realized: “The best time to learn personal finance was 35 years ago. The second best time is now.”

Business Education, Career Management, CEO, Entrepreneurship

Why do some CEOs hesitate to be entrepreneurial?

In a recent session in my CEO-2035 class, a student asked this question. Here’s how I answered it:

CEOs of established firms often hesitate to be entrepreneurial for several reasons:

  1. Risk Aversion: Established firms typically have significant resources, reputations, and shareholder expectations to consider. Entrepreneurial activities often involve high levels of uncertainty and risk, which could jeopardize the firm’s stability and profitability.
  2. Focus on Short-Term Performance: Publicly traded companies are often under pressure to deliver consistent, short-term results to satisfy shareholders and analysts. Entrepreneurial ventures can take time to generate returns, potentially affecting quarterly earnings and stock prices.
  3. Organizational Inertia: Large, established firms often have deeply ingrained processes, cultures, and structures that can be resistant to change. This inertia makes it difficult to pivot or take on new, innovative ventures that require flexibility and adaptability.
  4. Resource Allocation: Established firms often prioritize the allocation of resources to proven, profitable areas of their business. Investing in new, untested ideas may be seen as diverting resources away from these core areas, potentially diluting focus and performance.
  5. Complex Decision-Making Processes: In large organizations, decision-making tends to involve multiple layers of management and bureaucracy. This can slow down the ability to act quickly on new opportunities, which is often necessary in entrepreneurial ventures.
  6. Fear of Cannibalization: For companies with established product lines or services, there may be a fear that new, entrepreneurial products could cannibalize existing offerings, leading to internal competition and reduced profitability.
  7. Regulatory and Compliance Concerns: Established firms are often heavily regulated, and entrepreneurial ventures may involve navigating complex legal and regulatory environments. The potential for regulatory challenges can deter CEOs from pursuing innovative, but potentially risky, opportunities.
  8. Leadership Style and Experience: Many CEOs of established firms have built their careers on managing large organizations rather than on entrepreneurship. Their leadership style may be more suited to optimizing existing operations rather than fostering new, disruptive ideas.

These factors contribute to a more cautious approach, making CEOs of established firms less likely to engage in entrepreneurial activities compared to those leading smaller, more agile companies.

Business Education, Entrepreneurship, Tech

I classified the entrepreneurs who create software platforms under 3 categories.

In the class I discussed that while creating hosted platforms that bring demand and supply together to transact, entrepreneurs may restrict their roles solely to developing the platform and hosting it, to functioning exclusively as Subject Matter Experts who hire third party software developers, or to acting as both SMEs and software developers. Which option an entrepreneur picks depends on his/her background and other exogenous and endogenous factors. I agree it may be argued that certain types have inherent disadvantages/disadvantages and that’s up for discussion. Click the image below to download the slides I used in the class. Hope you had some takeaways and points to ponder from this class. I admire your entrepreneurial drive and enthusiasm. I didn’t spend much time on monetizing APIs and if you have questions, please contact me in my Stanford email ID.


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Career Management, Entrepreneurship, Fintech, Python, Tech

IIT Madras launches online Bachelor, Diploma in Datascience and Programming

It’s here finally! It has been my dream that a reputed school in India offer an online undergrad degree in Computer Science and now IIT-M is doing it. Now it’s open to all. Well, almost to all. I wish IIT-M opened it to all, not solely to those who completed 12th grade! I see a big demand for this course and wish IIT-M success. This is going to open doors to so many poor, bright students. Please send me your views to my Stanford email ID.


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CEO, Entrepreneurship, Private Equity

Remember our discussion on Hostile Takeovers in the PE, CEO classes and on how countries are vulnerable?

The heading in one of my slides was ‘How to take over a country peacefully?’. My answer was ‘by taking over the vital companies in that country’. I hope you remember that discussion in the PE/CEO 2030 class. The COVID situation may make scuh scenarios a reality. India is addressing this issue. Please read on. As usual send your views to my Stanford email ID.

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CEO, Entrepreneurship

Remember our discussion on how important timing is for funding? Here is an invaluable example.

In our Entrepreneurship class, we discussed how long one can wait to obtain funding and the factors influencing the timing. In the following piece, a founder is discussing how his decision not to prioritize funding cost him heavily. Please read the part about what to and what not to outsource especially. Click on the image below. As usual please send your comments to my Stanford email ID.

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Career Management, Entrepreneurship, Machine Learning, Tech

The 10 most in-demand skills of 2019, according to LinkedIn

I don’t like it, but the four of the 6 top skills required are IT skills! Please read on. Analytical reasoning is not exclusive to IT and I haven’t considered it as an IT only skill! Others are.

1) Cloud Computing
2) Artificial Intelligence
3) Analytical Reasoning
4) People Management
5) UX Design
6) Mobile Application Development

Click the URL and read on……

The 10 most in-demand skills of 2019, according to LinkedIn

Ram Subramaniam Stanford
Entrepreneurship, Tech

IT for Startup Ventures – IIM Rohtak

Hi all,

You will find the slide deck I used in the class in this blog. I know the class was short in duration and one core issue everyone wanted to discuss was finding a tech co-founder. While this is not easy, it’s not impossible. This requires efforts from your side to meet people outside your network and establish connections. Over time you will meet tech experts who you can trust. But you need to be relentless.

Click Here to Download Slides

Ram Subramaniam Stanford