What Sank Yahoo? Blame Its Nice Guy Founders - Bloomberg

Somewhere along the way, the exclamation point was lost

"During the 2000s, Yahoo’s biggest mistakes were failures of will. Semel, billed as a “deals guy” from Hollywood, could have bought Google in 2002, as Fred Vogelstein reported in Wired. Yahoo also came close to buying Facebook in 2006, until Semel lowered his offer from $1 billion to $850 million after a disappointing earnings report, alienating an already reluctant Mark Zuckerberg in the process, according to David Kirkpatrick’s book, The Facebook Effect.
These acquisitions probably looked like risky, uneconomical moves that Yahoo investors might hate. That’s the whole point. Web companies need the unique power of founders to do unpopular things. Page advocated for Google to buy the money-losing video sharing site YouTube in 2006; Zuckerberg made what seemed like an outrageously overpriced bet on the photo app Instagram in 2012. This is how tech companies survive—the ability to take risks."

What Sank Yahoo? Blame Its Nice Guy Founders - Bloomberg