Lee Briggs reflects on his experience within the Tailscale community, where concerns about the potential decline of user experience loom large. He highlights Corey Doctorow's concept of enshittification, which suggests that services that initially solve user problems often evolve into platforms that exploit those users. This fear is common among users, stemming from a broader belief that if a service is free, the user is the product. However, Briggs argues that these ideas oversimplify the dynamics at play and fail to account for the specific motives driving companies like Tailscale. As Tailscale's Director of Solutions Engineering, Briggs understands the balance between user satisfaction and business growth. Many companies rely on venture capital to expand, which creates pressure to generate revenue. He emphasizes that Tailscale's growth strategy hinges on product-led expansion, where satisfied individual users transition into advocates for the product within their organizations. Unlike large consumer platforms that monetize users through ads or fees, Tailscale's revenue primarily comes from businesses. If Tailscale were to compromise its personal tier to chase short-term gains, it would undermine the trust that fuels its user base and ultimately hurt the company's growth. Briggs critiques the prevailing narrative of inevitability surrounding enshittification, arguing that companies don't decline simply due to time; they do so when their incentives shift or leadership prioritizes short-term profits over user trust. He stresses that trust is vital for Tailscale, as users depend on its services for secure network access. If that trust erodes, even well-intentioned changes will be met with skepticism. He concludes that instead of hastily labeling changes as enshittification and scaring users away, there's a need for transparency about the trade-offs involved in maintaining the service.