ESPN's Bill Simmons on ESPN's Nate Silver, Being a Boss and Building His Site

At South By Southwest this weekend, ESPN’s Bill Simmons, who runs his own Grantland site, appeared onstage with ESPN’s Nate Silver, who is launching his own FiveThirtyEight.

You’ll be hearing a lot more about Silver’s site in the next few days, because it’s launching on March 17. But I wanted to take a few minutes to check in with Simmons, whose sports-plus-pop culture site is the template Silver is using for his politics-plus-lots-of-stuff site. Here’s an edited version of our chat:

Peter Kafka: You’re coming up on Grantland’s three-year anniversary this spring. What have you learned since you launched?

Bill Simmons: Just how hard it is to do it, week after week. And that when you have a whole bunch of people working together, how the mood of the office can ebb and flow, depending on how things are going. Right now we’re in a really good groove. But two months ago, when the Dr. V thing happened, it was really tough.

You spent a lot of time writing a column on your own, and now you’re running a 20-person company. Do you like that?

Figuring out how to be the guy who’s in charge of stuff has probably been my biggest lesson. There’s a lot that goes into that.

This is a really dangerous time for us. Because you can hit a point — we’re not massively successful or anything, but I think we’re doing okay — where you just kind of become who you are. I don’t want that to happen. We’ve been having a lot of meetings the last three months, trying to come up with big-picture ideas, that will change our site, push it to another level.

What sort of stuff do you think will do that?

The Steve Nash thing (a series of video stories about what will likely be the NBA star’s last season). That’s cutting edge, and unlike anything that’s been on the Internet. And we need to come up with seven of those kind of things a year. And I think we have a couple things coming that are on that level. Last year, I look back at it, and we had a really good year. But from a standpoint of looking at where we were in January 2013 and December 2013, we were basically the same site. We just have to do better than that.

Grantland created a path for Nate Silver to follow. What advice have you given him?

I was able to help as he was trying to figure out what the site was, by helping him carve out parameters about what he was going to do. Like telling him — get as much figured out before you start the site as you can, because once you’re in a big company, they have a way of trying to grab you here, and grab you here, and all of these people are coming at you. All he wants to do is do is this site, and do some ABC news stuff.

Also, I think it’s not the site that some people think it is. It’s not going to be a politics site. It’s going to be a really smart site that hits politics and weather and sports and pop culture. Which I think is smart, because he needs to grow. You don’t just want to be the guy who shows up every four years and goes 50 for 50.

So now ESPN has two big sites, branded by the stars who run them, not ESPN itself. Why do you think they think that’s a good idea?

One of the benefits of 30 for 30, and Grantland, and PTI, and some of those other things, is if you don’t have things like that, you’re just a network that shows games and highlights. And you can get games and highlights on 12 different channels.

We do it the best, we make the most money from it. But you’ve got to resonate with people in other ways. I think Nate’s site is another way to do that.

But trying different things doesn’t necessarily mean giving you and Nate have your own fiefdoms.

With me, it was like — “I want to do this, I want to do it out of LA, I don’t want to have ESPN in the name, and I need a lot of leeway to do this. I have an idea, and I think I know how to do it, and I want to do it with you guys.” From the get-go, we were on a little island, which was great.

But now it’s time for us to start using the company better. I’m totally realistic. Grantland’s doing really well, but at the same time most people don’t know it even exists. So we have to figure out how to use the company better, to get on TV more and do more multimedia stuff.

This article originally appeared on Recode.net.

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