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If there was ever a company that would be defined by fumbling the bag… it would be Yahoo…
As far as the folk lore goes, in 1998 the company turned down an offer to buy a website for a million dollars from two guys called Larry Page and Sergey Brin…
Four years later they got another chance to buy google, this time for 5 billion dollars… they declined, and just two years later it listed for 23 billion dollars.
They failed to close a chance to buy both YouTube and Facebook, and they also lost an opportunity to sell themselves.
In early 2008, then Microsoft CEO Steve Balmer offered to acquire the company for $35 a share, Yahoo leadership countered with $37 and Balmer walked away… six months later in the midst of the GFC… they were worth $11 a share… Bain capital then offered to buy them for 25 billion dollars, they rejected, and ended up selling later for less than 5 billion dollars.
Even when they got it right… they got it wrong.
They purchased a 40% stake in Alibaba in 2005… and then sold off half of their stake before an IPO which would have made them an additional 35 billion dollars.
Now Yahoo is (clearly) not an investment firm… but it's not like its core business is that great either…
In the 2010s analysts estimated that the company itself was actually financially less than worthless…
According to its own balance sheet, the actual business (which was still one of the most popular sites in the world) was technically worth… negative 10 billion dollars… which does raise the obvious question of… how is that even possible?
Yahoo is a bit of a sad story but it is a good historic business study, that just being in the right place, at the right time, doing the right thing, does not guarantee any level of success…

How Is Yahoo Still A Thing?
Why Does Yahoo Refuse To Die?