In March 2008, after raising $600 million, acquiring 18% of the outstanding stock, and threatening a proxy contest, I was elected to the board of The New York Times Company. The company was struggling to make the transition from print to digital. The stock was at $17 (down from $53 in 2002). Investors were fleeing the Gray Lady for hotter, younger online media properties.

The Times is likely the most important media firm of the last century. At one point I had dinner with Bill Keller, executive editor at the time, who had to excuse himself to help negotiate the release of a Times journalist taken hostage by the Taliban. Our best and brightest were doing hostage negotiations while Google’s best were busy programming ways to steal and monetize the content of the hostage. In my first meeting, I urged the board to consider shutting off Google’s crawlers and got nowhere.

I failed to establish a productive working relationship with Chairman Arthur Sulzberger. Striking a balance between being right and being effective is something I’ve struggled with my entire life.

My thesis was that the Times had the best brand in news globally, but that it needed to become a digital platform, monetizing traffic across an array of products. I lobbied the firm to sell its non-core assets (the seventh tallest building in America, the Boston Globe, 17% of the Red Sox, 16 regional newspapers, and I also lobbied to cancel the dividend (hush money for family members without overpaid jobs at the Times), double down on digital, move to subscription, and cease the idolatry of innovators (Google crawling our content for free, Apple distributing our content on poor terms).

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