Yahoo!

Let's be strategic about this: Yahoo represents the single greatest case study in corporate fumbling in the history of technology. This was the company that had it all—first-mover advantage in web directories, a dominant portal position, massive traffic, cultural relevance, and not one but two opportunities to acquire Google (in 2002 for $5 billion, which they rejected, and again when Google came back willing to sell for $3 billion). They also had a chance to buy Facebook for $1 billion in 2006. Instead, they zigged when they should have zagged, pivoted when they should have focused, and acquired when they should have innovated, ultimately selling their core internet business to Verizon for $4.5 billion in 2017—less than they paid for Broadcast.com alone in 1999.

But here's what the business school analysis misses: in its prime, Yahoo genuinely worked. Before Google made search algorithmic, Yahoo's hand-curated directory was actually useful. Real humans organized the internet into categories. You could click through Arts > Music > Genres > Rock > Alternative and find curated lists of websites about bands. It was the internet as library, with librarians. The Yahoo homepage in 1998 was a portal in the genuine sense—a door to everywhere, with news, email, sports, stocks, weather, all arranged in that cluttered grid that now looks impossibly retro but which represented, at the time, the abundance of the digital frontier.

Yahoo Mail was email for normal people before Gmail. Yahoo Messenger was how an entire generation learned to type "brb" and "lol." Yahoo Groups hosted communities that would be impossible to replicate today, forums where people connected over obscure hobbies and shared expertise without engagement algorithms. Yahoo Finance, somehow, remains excellent even now—one of the few products that survived the company's long decline. Yahoo Answers, despite becoming a meme for its spectacularly stupid questions, was actually an early experiment in crowdsourced knowledge that influenced everything from Quora to Stack Overflow.

The decline was death by a thousand cuts, but mostly by executive malpractice. The parade of CEOs—Terry Semel from Hollywood who didn't understand tech, Carol Bartz who famously got fired over the phone, Marissa Mayer who burned billions on acquisitions that went nowhere while Yahoo's core products rotted—reads like a management case study in how to destroy value. They killed GeoCities, ruined Flickr, botched Tumblr, and failed to invest in the things that might have kept them relevant. Every strategic review recommended a different direction. They became, in the end, a holding company for a stake in Alibaba, with a media business that Verizon eventually renamed "Oath" and then pretended never existed.

I give Yahoo a 6.2 because the bones are still there, somehow. The homepage still gets traffic from people who set it as their browser default in 2003 and never changed it. Yahoo Finance still delivers. Yahoo Sports limps along. There's something poignant about visiting yahoo.com today—it's like walking through a mall that used to be the center of town, where a few stores remain open amid the vacant storefronts, serving customers who remember when this was where you went for everything.