#3: Yahoo Failed to Close a Google Deal
Yahoo’s relationship with Google produced one of Silicon Valley’s great what-ifs. Yahoo used Google to power search results and explored acquiring the fast-growing company in the early 2000s. Accounts differ on the exact numbers, but one widely reported version says Google sought roughly $3 billion after Yahoo initially discussed a lower valuation, and Yahoo walked away. Google subsequently built advertising around search into one of history’s greatest businesses. Yahoo, once the internet’s front door, eventually sold its core operations to Verizon.

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