# The Life cycle of Enshittification

Page: https://stenobird.com/podcast/trail-boss-radio-ai-tech-digital-independence-7780171/the-life-cycle-of-enshittification
Text version: https://stenobird.com/podcast/trail-boss-radio-ai-tech-digital-independence-7780171/the-life-cycle-of-enshittification.md
Podcast: [Trail-Boss Radio: AI, Tech & Digital Independence](https://stenobird.com/podcast/trail-boss-radio-ai-tech-digital-independence-7780171)
Published: 2026-07-03T16:44:01+00:00
Episode link: https://johnsondanny866.podbean.com/e/the-life-cycle-of-enshittification/
Audio file: https://mcdn.podbean.com/mf/web/tszvc67erpyhwfwt/The_life_cycle_of_enshittification.mp3
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JSON: https://stenobird.com/v1/public/podcasts/trail-boss-radio-ai-tech-digital-independence-7780171/episodes/the-life-cycle-of-enshittification
Duration seconds: 1233

## Resource

The Life Cycle of Enshittification Why do so many great products seem to get worse over time? Why do platforms that once put customers first gradually become filled with more advertising, higher fees, more restrictions, and fewer choices? In this episode of Trail Boss Radio, we explore the fascinating concept known as "enshittification"—the predictable life cycle that many digital platforms experience as they grow. Using the Trail Boss approach, we break this complex idea down into simple, everyday language. We'll discuss how many platforms begin by delighting customers, then shift their attention toward advertisers, investors, or corporate growth, often leaving users with a very different experience than the one that attracted them in the first place. But this episode isn't about complaining. It's about learning. More importantly, it's about asking a bigger question: What happens when you build things you own instead of depending entirely on platforms you rent? We'll explore how websites, email lists, digital products, AI tools, and even long-term investments like ETFs can help create greater independence by giving individuals more control over their future. Technology has created incredible opportunities. But every tool has strengths and weaknesses. Understanding those trade-offs helps us make wiser decisions. In this episode, you'll learn: What "enshittification" means in simple, practical terms. Why many digital platforms follow similar life cycles. How incentives influence business decisions. Why building assets you own can reduce dependence on changing platforms. How entrepreneurship, investing, and technology all connect through ownership. Why diversification applies to your business strategy just as much as your investment portfolio. How the Trail Boss Guide to…

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