Over the last six months, I’ve spent a lot of time in the Tailscale community - helping users debug issues, answering questions about how we sell the product and explaining,

Lee Briggs is a software engineer, blogger, and technology enthusiast known for his expertise in web development and software architecture. Readers can learn about coding best practices, software design principles, and emerging technologies. With blog posts, tutorials, and open-source projects, Lee Briggs shares  insights and best practices for building high-quality software solutions.

Lee Briggs

The term 'enshittification' has become overused to the point where any change to a product is viewed with suspicion. Not all venture-backed companies inevitably degrade their products - incentive structures matter. For B2B tools like Tailscale, maintaining a strong free personal tier isn't charity but essential business strategy: happy individual users become advocates who bring the product into their workplaces. The real revenue comes from companies, not individuals, so degrading the personal experience would destroy the primary customer acquisition channel. Trust compounds slowly and breaks quickly, and treating enshittification as inevitable removes accountability from companies that actually make poor choices.

The enshittification of enshittification