In the late 1990s, amid the chaotic early days of the internet, a company called RealNames launched an audacious plan to revolutionize web navigation. Its idea was simple yet bold: allow users to type single keywords like 'Amazon' or 'Money' directly into browsers instead of full URLs like 'Amazon.com'. This would bypass the Domain Name System (DNS), the foundational technology that translates domain names into IP addresses. RealNames raised over $100 million in venture capital and struck a pivotal deal with Microsoft to integrate its keyword system into Internet Explorer, giving it access to billions of page views. For a time, it seemed poised to reshape how people accessed websites. But cracks soon appeared. Users adapted faster than expected, learning to append '.com' without needing a new system. Microsoft, meanwhile, began competing directly by introducing features like autocomplete, undercutting RealNames’ value proposition. The final blow came in 2002 when Microsoft terminated their exclusive agreement, redirecting traffic to its own search engine. RealNames collapsed shortly after, leaving behind angry investors, laid-off employees, and unresolved issues for non-English-speaking users who had benefited from its multilingual capabilities. Years later, the brand resurfaced under Tucows as a personalized email service offering addresses like [email protected]—marking a quiet but ironic second act for a name once tied to a grand, failed vision of internet transformation. The story of RealNames stands as a cautionary tale about overestimating user friction, underestimating corporate partners, and attempting to disrupt deeply entrenched systems without universal buy-in. It also highlights the resilience of open, decentralized technologies like DNS, which continue to power the internet’s infrastructure far beyond the lifespan of proprietary challengers.