I used to be an avid Cracked reader. Yes, the quality has gone dramatically downhill and they are definitively in Buzzfeed territory. I occasionally will click into one of their lists, only to have the photos not load. How the hell is a company this bad at web design? It's a motherfucking slide show with 5 pics and they can't load? Focus: What are some companies that are hopelessly inept at the Internet? Where have you seen well-established brands break down?
Hopelessly inept at the Internet? Probably Sears. The reason is because they have been hilariously mismanaged for past 20-30 years and they had all the resources to become an Amazon-level powerhouse during the dot com boom and they completely missed the boat. Sears today is an afterthought, but back then it was one of the biggest games in town, pre-Walmart. Their catalog was a gold-mine for them. The logical step would have been to focus on converting that into an online store. They had the procurement, inventory and resources to get a huge head start on every one of their competitors. They even had their own god damn ISP that they never used for its intended purpose. They also had their own credit card (Discover), that could have been spun into an online payment system. The reason that occurred was because their CEO was famously inept. To make a long story short, his approach was to raise a ton of capital by closing stores or running them with a bare-minimum amount of resources and plugging that money into stock buybacks to raise the overall stock price and please his investors. This started in the mid-90s and although buybacks are not uncommon, it depleted the liquid cash the company had and essentially destroyed Sears' ability to compete with other retailers like Amazon, Walmart.com, etc. This then created an inescapable feedback loop where combined with the overall decline of malls in general, Sears' retail location started failing, which worried investors, which caused the CEO to sell off more assets to pump up the stock to keep investors happy, which further caused stores to fail, and so on. Meanwhile, the online powerhouses we know today were gaining steam and Sears was going in the opposite direction. Everyone thinks of Blockbuster as the famous example of a company missing the Internet boat, and they surely did (just not for the reasons most people think), but Sears should be a case study in every business school class on how to destroy a successful company.