Simmons and Silver, Sittin' in a Tree


The problem with two guys from ESPN getting together to talk to each other about ESPN for an hour is that no one’s there to check them on their ass-kissing when they ass-kiss their way through their own apologies about their ass-kissing.

Photo by Gary Miller

Those two guys we speak of are Bill Simmons and Nate Silver, two sportswriting behemoths who’ve obtained the good fortune over the past three years of building their own websites – Grantland for Simmons, and Five Thirty Eight, which launches next Monday, St. Patrick’s Day, for the recently hired Nate Silver – on ESPN’s mighty dime. The two spoke Saturday of holding nearly full autonomy in shaping both sites’ earliest templates, and all the advantages and pitfalls that come with that power.

Said pitfalls – motivation, personnel management, and roughly 25 percent of site inadequacies that can only be satisfied through simple trial and error – were all interesting, though they were largely spaced out by the bevy of compliments the two paid regularly to ESPN head John Skipper and his voluminous executive team, all of whom green lighted the two and their websites and allowed them to build each any way they saw fit. (Now in its third year, Grantland focuses on sports and entertainment. Five Thirty Eight’s set to center on sports, politics, economics, science, and “lifestyle.”)

Those compliments began going a bit overboard midway through the session, when Simmons admitted he was “not trying to be a kiss-ass” after describing ESPN as “a smart company that makes a lot of money and hires smart people,” the opening of what he jokingly considered an “infomercial.” Tough to blame the two, however. With no one but colleagues around to ask questions, there wasn’t very much standing in the way of a love fest.

Media & the Personal Brand – ESPN, Grantland & 538

Saturday, March 8, Austin Convention Center

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