It began life as a web directory, manually curated and categorized by humans, who were known simply as “the surfers.” Yahoo was the first site to add news, sports, and finance feeds to its web directory

By early 1998, Yahoo had added email, shopping, classifieds, personals, games, travel, weather, maps, people search, celebrity chats, a kid-oriented version called Yahooligans, and an online magazine.

Before there was a YouTube, there was Broadcast.com, which turned into Yahoo TV. Before Instagram, there was Flickr. Before Evernote, there was Yahoo Notebook. Before Spotify, Yahoo Music. And on and on.

More important from a business standpoint, Yahoo pioneered the pay-per-click advertising model that soon became ubiquitous across the internet

“One of the things people don’t realize is that it’s those early TV spots that really made Yahoo an overnight global brand sensation,” says Parker. “It was that Do You Yahoo? tagline and that yodel. When I started in ’98, I’d go to parties, and people would see me and start yodeling.”

“When we launched Yahoo with a TV campaign on both coasts, there were at least 130 other search engines,” says John Yost, president of Black Rocket at the time. “But none of them had that cheeky name, and they were the first to get out there and advertise in a big and memorable way.”

For many, Yahoo and the yodel became synonymous.

People wanted to know who this wacky company was.

Yahoo lost many of its advertisers, and nearly all of its value, in the dotcom crash that began in April 2000. It never truly recovered.

In 1998, Yahoo had a chance to license an innovative new search technology created by a pair of Stanford grad students for $1 million. Instead, David Filo convinced Sergey Brin and Larry Page to strike out on their own

In 2002, Yahoo had a second chance to buy Google. This time, CEO Terry Semel offered $3 billion for the company; Page and Brin turned him down, reportedly holding out for $5 billion.

in July 2006, when Yahoo tried to buy Facebook, then a college-oriented network with roughly 7 million members, for $1.1 billion. Internet lore has Mark Zuckerberg walking away from the deal when Semel cut the offer to $800 million after a drop in Yahoo’s share price.

Ring says Yahoo’s biggest mistake was not allowing paid search ads to coexist with organic search results. For the first years of its existence, search results were considered editorial content, not to be sullied or diluted by advertising. By the time Yahoo realized its mistake–and acquired Overture, the company that invented paid search advertising, for $1.6 billion in 2003–Google was already steaming ahead.

Yahoo decided to build its own advertising platform mostly from scratch, says Flake, who came to Yahoo as part of the Overture acquisition. Code-named Project Panama, the new platform took nearly three years to complete. By then, the search wars were over; Google had won.

more than that, Yahoo never really decided what it wanted to be when it grew up. Was it a technology company? A search advertising platform?

Trying to be everything to everyone was Yahoo’s downfall, says Parker.

“We were like Eratosthenes, whose nickname was Beta because he was second best at everything he tried,” he says. “That was Yahoo.

“They owned the world, but they weren’t looking to the sky.”