I'm trying to recall from memory here since the book isn't in front of me.
He's talking about selling his first company, its all about making hard choices and such. The company is dying so he had two options either sell the company now (for a smaller amount) or fire most of the staff and sell later. He mentions how he had to let go of the staff but later sold it for a larger amount of money. He then says something to the degree of considering it a "win".
I don't know that I consider laying off a ton of people for a greater exit a win. I consider it a move to get more money, but I doubt anyone chasing money is going to "fix the internet".