Business, Rewritten by AI

Strategies to avoid getting Chegged in 2025

It’s been an intense—if exhausting—few weeks as I’ve crisscrossed the country speaking on the future of AI in business. From private events in Palm Beach, New York, and Los Angeles to co-hosting the AI Trailblazers Agent Summit in Las Vegas, I’ve already logged more travel in March than I’d like to admit.

A highlight: I spoke at an intimate 25-person event in Palm Beach alongside Professor Scott Galloway of NYU and Professor Sandra Matz of Columbia University—both outstanding and great company to be in.

The downside? The newsletter slows down when I’m on the move. Thanks for your patience—regular rhythm resumes now.

Selfie with Prof. Scott Galloway after we spoke — his podcast is a must listen.

What hasn’t slowed, of course, is the pace of AI. Every week seems to bring another wave—faster, deeper, more disruptive. In just the past few weeks, Google introduced “AI Mode” in Search. Claude integrated live search queries. Nvidia’s developer conference revealed a new generation of AI-first chips, cementing its role at the core of this transformation. At the Adobe Summit, generative AI stole the show, offering a glimpse into how creative workflows are being radically reimagined. Adobe also released 10 new AI agents.

Last week, Puma even launched an ad built by autonomous AI agents—an early signal of a future where creativity and execution blend seamlessly. Meanwhile, broader political currents are colliding with AI’s trajectory. Reports suggest a potential Trump administration may pressure AI companies to remove ‘ideological bias’ from models—raising complex questions about control, governance, and freedom of thought. And DeepMind’s CEO made headlines with a chilling forecast: humans may have just five years before AI surpasses us in general intelligence.

It’s a lot. And it’s accelerating.

But beneath the surface-level noise is something more profound: AI is no longer just enhancing tools—it’s rewiring the frameworks of strategy, operating models, marketing and competitive advantage. It’s changing how we acquire customers, how we create value, how we build brands, and ultimately, how businesses survive—or don’t.

Which brings me to Chegg.

The Chegg Collapse: A Cautionary Tale

One story in particular caught my attention recently: Chegg is suing Google, claiming that recent changes to Search have unfairly decimated its business. For years, Chegg made its money by attracting students to its platform for textbook rentals, tutoring, and homework help. Its model relied on two pillars: subscription-based services and search visibility.

Then, the double blow.

First, students began turning to large language models like ChatGPT and Perplexity to get instant, free answers—reducing the need to pay for Chegg. Then, in mid-2024, Google launched AI Overviews (AIO), which deliver rich, AI-generated responses directly on the search results page—further diverting traffic from sites like Chegg. Chegg has claimed that Google is using its SEO-optimized pages to train and power AI Overviews—effectively appropriating its content and displaying it within search results.

The consequences have been brutal. Chegg’s stock is down nearly 90% over the past two years. In Q4 2024, the company reported a $6.1 million net loss on $143.5 million in revenue. It has since announced layoffs, office closures, and is now exploring strategic alternatives while suing Google.

Chegg’s astonishing five-year stock price decline

Whether Chegg can recover remains unclear though I hope it does. But whether others can learn from it? That’s essential. Because this isn’t just a Chegg story—it’s a preview of what’s coming for businesses across sectors.

Five Strategic Lessons from the Chegg Saga

1. Knowledge Businesses Are Ground Zero for AI Disruption
   If your core offering is information delivery, AI is already a substitute—and, so far, the courts aren’t offering much protection. What happened to Chegg is now unfolding across industries: for example, expert-driven businesses—legal research firms, financial advisory platforms, publishing companies, and educational services—are feeling the squeeze. The value that once came from proprietary knowledge is being rapidly commoditized.

2. Community Is a Moat. Build It.
   As AI makes information instantly accessible and increasingly commoditized, the true differentiator isn’t what you know, but who you're with. Products that foster human connection—where users come for answers but stay for relationships—are more resilient. Think Reddit’s discourse, Stack Overflow’s peer recognition, or the creator-driven communities on TikTok and Instagram. When knowledge is no longer scarce, value shifts to context, emotion, and social capital. Community builds loyalty, creates switching costs, and delivers the kind of emotional stickiness AI can’t replicate. Community is your new moat.

3. SEO Is Being Rewritten—Literally.
   The days of keyword optimization as a strategy are numbered. LLMs don’t search like humans. They summarize, synthesize, and serve answers now. If you want to show up, your content has to be structurally relevant, deeply contextual, and widely cited so that you’re providing the LLMs with multi-modal comprehensive answers. You’re no longer optimizing for a search engine keyword—you’re becoming a credible source for an AI service whether it is ChatGPT, Perplexity, Gemini, Claude or Meta AI. Get to know them well and fix your content libraries.

4. Brand and Experience Are Your Lifeline.
   In a world flooded with AI-generated alternatives, only true distinctiveness endures. If you haven’t built a strong brand, cultivated customer loyalty, or created experiences that spark word-of-mouth, your performance marketing costs will keep climbing while returns diminish. SEM is getting more competitive. SEO is becoming less reliable. And undifferentiated, “me-too” products will be swept away. What’s more, this shift won’t be linear—it’ll be unpredictable and uneven. You won’t know when you’ll get hit or when your once-reliable acquisition channels will suddenly stop working. A single Google algorithm update could be the trigger.

5. Business Models like Marketplaces Are Structurally Vulnerable
   Alongside knowledge-based businesses, marketplaces are particularly exposed. I’ve spent a lot of time in that world—they’re often margin-thin, heavily reliant on paid traffic and large SEO content libraries, and frequently lack strong product or brand differentiation. When traffic shifts and customer acquisition costs (CAC) spike, they have little buffer to adapt. Even more challenging, many struggle to build loyal, repeat customers who return without paid acquisition. Some exceptions exist—like Uber and Airbnb—but many continue to overspend on performance marketing while still grappling with media mix modeling and how to use upper-funnel investment to generate demand.

6. Segment, Specialize, and Differentiate—Deeper Than Ever Before
   The AI era rewards precision. Businesses must refocus on deeper customer segmentation, vertical-specific solutions, and product enhancements that meaningfully integrate hardware and software. In a world where generative tools commoditize the generic, differentiation lives in the details—features that solve real, contextual problems for narrowly defined users. This shift is also fueling a new wave of AI-enabling technologies built for specific industries. One of my investments, Instalily, exemplifies this trend by developing autonomous agents tailored exclusively to vertical use cases.

7. Global Doesn’t Mean Homogenous—Localize Your AI Strategy
   AI adoption varies widely across regions due to differences in culture, infrastructure, regulation, geopolitics and model access. What works in one market may fail in another. Companies need a multi-market playbook—tailoring products, go-to-market plans, and ethical standards to local realities. For example, Chinese researchers have already repurposed Meta’s open-source LLaMA model for military applications—something that may not be legally or ethically permissible in the future as national AI governance tightens. As governance evolves, more aggressively localizing both strategy and tech stack won’t be optional—it will be essential

What Comes Next?

We’re still living in a human-dominated Internet—for now. But consider this: what happens when most of your traffic, or even most of your e-commerce, is mediated by AI agents making decisions on behalf of users? What happens when your homepage is no longer your front door, and your brand must prove itself to an an AI agent?

We’re not there yet—but we’re close enough to start planning for it.

Now is the time to identify which parts of your business are ripe for AI reinvention. Which teams can lead the charge. Which leaders have the courage, intensity, and strategic clarity to build new moats while the ground is still shifting.

Because if you wait, you may find yourself Chegged before you even saw it coming.

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Where I will be

In the coming weeks, I will be speaking at the 2025 ANA AI and Technology Conference, the Hispanic Marketing Council Annual Summit, conducting a Corporate Workshop in New Orleans and will be doing a Corporate Speaking Engagement in Purchase, New York. In all probability, I will also be traveling to London mid April as well for a consulting engagment (let me know if you’d like to connect while there).

Where I’ve been

I recently joined Greg Stuart and Rex Briggs on the Decoding AI podcast for a thought-provoking conversation about AI predictions for 2025, what marketers need to focus on today, and how to publish a book on marketing with AI.

What I’m reading

• We have 5 years before AI will outsmart us (Fortune)

• The Rise of the AI Manager (Fast Company)

• AI Scientists Are Told to Remove ‘Ideological Bias’ (Wired)

• Lines blur between performance & brand marketing (WSJ)

• Sam Altman & Building a Consumer Tech Company (Stratechery)

What I’ve written lately

• The AI Dilemma: Smarter or Weaker? (February 2025)

• Can the Super Bowl change Search? (February 2025)

• AI Tsunami: Are You Falling Behind? (January 2025)

• 2025 AI Predictions You Can’t Afford to Miss (January 2025)

• Fires & Falsehoods: A Tale of Two Crises (January 2025)