Yahoo — Turning Down Google and Facebook

Yahoo's refusal to buy Google for $1 million in 1998 and Facebook for $1 billion in 2006 represents the two most disastrous missed opportunities in tech—those acquisitions would be worth over $2.5 trillion combined today. Instead, Yahoo pivoted through at least seven different strategies, including search advertising, content portals, and social media, but never executed one well. By 2017, Verizon bought Yahoo's core internet business for $4.48 billion, a fraction of its 2000 peak valuation of $125 billion. This pivot-by-turmoil outperforms Quibi in longevity but underperforms every other item here in strategic cohesion; at least Kodak had a clear, if wrong, rationale. Yahoo's 22% annual revenue decline from 2009 to 2016 shows how aimless pivoting costs more than a single bold failure.