Episode
How AI Accelerates Digital Enshittification
- Published
- Jul 7, 2026
- Duration seconds
- 1513
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Summary
How AI Accelerates Digital Enshittification Artificial Intelligence is changing the world at an incredible pace. It can help us learn faster. Build businesses. Write software. Create content. Solve problems that once took hours in just a few minutes. But every powerful tool comes with an important question: Who benefits the most? In this episode of Trail Boss Radio, we explore how Artificial Intelligence can accelerate the life cycle of digital platforms—and why understanding incentives may become just as important as understanding the technology itself. Using the Trail Boss approach, we explain how AI has the potential to dramatically improve customer experiences while also making it easier for companies to optimize advertising, automate decisions, personalize pricing, and maximize profits. The technology itself isn't good or bad. The outcome depends on how it's used. We'll discuss why some companies use AI to create more value for customers, while others may be tempted to use it primarily to extract more value from them. This conversation isn't about fear. It's about awareness. Because the more we understand how these systems work, the better equipped we are to make thoughtful decisions about the tools, platforms, and businesses we choose to use—and the ones we choose to build ourselves. In this episode, you'll learn: How Artificial Intelligence can accelerate the evolution of digital platforms. Why incentives often shape technology more than technology shapes incentives. How AI can improve customer experiences while also increasing platform control. Why understanding business models matters just as much as understanding AI. How ownership can provide greater resilience in an AI-driven economy. Why independent websites, digital assets, and long-term investments become…