Steven Levy relates the story of Wesley Chan, a Google product manager, derailing the Skype acquisition:
if Google bought Skype, Chan concluded, it would have to rewrite the entire Skype platform.
Basically, he was convinced that peer-to-peer wouldn’t work within Google’s infrastructure, and that Google could build a better mousetrap on it’s own.
Especially interesting is the description of the meeting when the deal went south:
“Salar [Kamangar, now CEO of YouTube] and I laid the grenades,” Chan told me. According to Chan, the pair went to Sergey Brin and convinced him it was a terrible deal. Then, Chan says, they brainstormed a plan to sabotage the deal in a key meeting of top executives, a gather that presumably would wind up blessing the purchase.
The idea was bait and switch—the executives in favor of the deal would assume that everything was on track, and Chan and his allies would use shock and awe to turn things around. Chan says that he began the meeting by praising the deal. “I even had a deck that was super supportive of it,” he says.
But, according to Chan, halfway through the deck, Sergey Brin seized the floor “and started getting really negative.” He asked a series of questions that he knew would get unsatisfactory answers. Is this purchase data-driven? Who is going to spend all those months commuting to Europe? (No one stepped up.) How long is the government review expected to take? As Chan had figured, the advocates of the deal were unprepared to respond to these last-minute objections.
Chan then described the climatic moment. “[Sergey] looks at me and says, ‘Why would I want this risk? We have a team capable of building the carrier, we have the users, we have hundreds of millions of Gmail users, why do we need to have Skype?’ And at that point, Sergey gets up and says, ‘This is the dumbest shit I’ve ever seen.’ And Eric gets up and walks out of the room, and I’m like, okay, the deal’s off.” And it was.