Things to consider over the US holiday weekend.
I’ve used the phrase enshittification on the show, as it’s become an economic term. The Guardian notes how Amazon, once celebrated for its customer-centric approach, is now facing criticism for what has been termed “enshittification,” a phenomenon where online platforms degrade in quality as they prioritize profits over user experience. This deterioration is characterized by tactics such as predatory pricing, hidden fees, and search manipulation, which ultimately lead to higher costs for consumers and diminished value for sellers. In the early days, Amazon invested heavily in customer satisfaction, but as it gained dominance, it shifted focus to extracting value from both users and merchants. Research indicates that businesses on Amazon face fees that can consume up to 51 percent of their profits, pushing them to raise prices across all sales channels, thereby impacting consumers directly. The article highlights this troubling trend as a significant concern for the future of online commerce, where the quality and trustworthiness of services are increasingly at risk.
A Columbia Law study pushes back on the success of IPOs. A recent analysis of millions of employee reviews reveals that satisfaction among workers significantly declines after companies go public. Specifically, data from Glassdoor indicates that employee ratings drop by an average of 10 percent regarding perceptions of senior management and 6.6 percent regarding work-life balance following an initial public offering. The research, which examined 3.7 million reviews from 2008 to 2022, found that employees who were with the company before the IPO felt the impact most acutely, with management and compliance roles experiencing declines up to 2.5 times greater than average employees. Regulatory burdens, such as compliance with the Sarbanes-Oxley Act and the need for quarterly earnings reports, were identified as key factors contributing to this decline. Interestingly, companies with strong environmental, social, and governance practices did not see as severe a drop in employee satisfaction, suggesting that a supportive corporate culture may mitigate some of the negative effects associated with going public.
What does it take to build AI Agents? Venture Beat writes how Notion has completely overhauled its technology stack to support agentic artificial intelligence at an enterprise scale, marking a significant shift in its productivity software. The company’s latest version, released in September, emphasizes transitioning from traditional task-based workflows to goal-oriented reasoning systems that enable AI agents to autonomously select and execute tasks across connected environments. Notion is currently used by 94% of the Forbes AI 50 companies and has a total user base of 100 million, with noteworthy clients including OpenAI and Figma. According to Sarah Sachs, Notion’s head of AI modeling, this new architecture allows for greater independence in AI operations, enhancing the ability to make multiple decisions within a single workflow. The shift aims to optimize user experience while ensuring that AI outputs are grounded in reliable enterprise data.
And Ed Zitron says “OpenAI is Just Another Boring, Desperate AI Startup.” He argues OpenAI is a company lacking a coherent strategy, as it diversifies into multiple sectors without clear focus, including social media, workplace productivity, and consumer hardware. Despite having 20 million paid subscribers for its ChatGPT service, OpenAI reported significant financial losses, spending $6.7 billion in the first half of 2025, which was 150% of its revenue for that period, highlighting a troubling trend in its operations. According to a report from The Information, OpenAI’s recent product, the GPT-5, has not met expectations and has raised concerns about its future revenue projections, suggesting that the company may struggle to maintain relevance in a competitive market.
Why do we care?
Some weekend brain fuel:
- Is Amazon showing us what happens when platforms go too far down the enshittification path? If your vendors are extracting more than they’re enabling, are you caught in the same trap?
- If going public kills employee morale, what does that do to innovation? What does that mean for vendors you trust who are heading to IPO—or already there?
- Notion rebuilt their entire AI stack to support agentic systems. Are your clients ready for AI that doesn’t wait for a prompt, but instead makes decisions? Are you?
- And OpenAI. It’s got millions of users and billions in losses. Is it the next utility… or the next WeWork?
These are strategy questions for IT service pros. They’re not about product features—they’re about risk, trust, and long-term alignment. So this weekend, ask yourself:
- Which platforms are helping you build—and which are bleeding you dry?
- What vendor relationships need a reset based on how they’ve changed?
- And are you building AI systems on shifting sand?
Food for thought—because your clients will still expect answers.