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ESPN's Bill Simmons Talks Podcasts, Grantland and His Next Contract

"I think they take it for granted. Not just how hard I work, but how hard everybody works."

Grantland

Bill Simmons, ESPN’s popular and controversial multimedia star, is in Austin this weekend at the annual South by Southwest interactive festival, taping a series of podcasts — a longtime focus for him — for his Grantland site. Simmons’ contract with ESPN is up for renewal soon, and there’s lots of speculation that he might leave his longtime home — especially after the sports giant gave him a three-week suspension for comments he made about NFL head Roger Goodell last fall.

I talked to him for a few minutes, after he chatted with former “Saturday Night Live” star Horatio Sanz. This is an edited transcript of our conversation:

Peter Kafka: Why come to SXSW and spend it in a studio, doing podcasts?

Bill Simmons: This is great for us, because there’s a million celebrities here. I always want to have people I can have a conversation with. So when I saw Horatio Sanz, who you just saw, was here, I’m like “I’m fascinated with this guy. I know how this will go, potentially.” So you want a mix of that with a couple [Charles] Barkley, Jimmy Kimmel guys.

You had an iPad in front of you during that interview, but it didn’t look you were looking at it. Do you do much prep for all of these?

I try not to prep, because I think it can ruin how it can go. Which is the opposite of a late-night show. I don’t want to have notes. If people think you’re looking at notes, and following some sort of script that you’ve laid out ahead of time, they check out a little bit. Especially if your eye contact is like [looks down] — I just think it’s bad. So what we’ve tried to create is a conversation. I’m right here.

You’ve been podcasting for many years now. But a lot of people just discovered podcasts last year, through “Serial.”

The “Serial” thing is great. You hear conflicting reports about how much people should be able to monetize podcasts. I think ESPN has had trouble monetizing it.

You said that more than a year ago. That’s still a problem?

Yes. Is that my fault? I don’t know. I think other people have had a lot of success monetizing it. I think for what ESPN does as a company — it’s a company that’s built toward selling bigger things. They have deals with a lot of sponsors, and their money is going to gravitate toward bigger properties that ESPN has.

The challenge for ESPN and a lot of other companies is trying to figure out how to keep those relationships, and also figuring out how to extend relationships, or create relationships with stuff that’s not Monday Night Football.

You’ve been podcasting for a while, and the money part seems like it has frustrated you the whole time. At some point do you think about bailing on the idea?

No, because they pay me a salary. It’s not like I have a percentage of what my podcast gets.

I do think, as a competitive person, the fact that we don’t have a sponsored studio yet is just perplexing to me. We shoot like 15 hours of TV in there. But I also don’t know anything about ad sales, and it’s probably a much more complicated landscape than I’m giving it credit for. But to me, that’s a no-brainer.

The format really lends itself to advertisers. When you watch TV, you check out during the commercials. In a podcast, you’re there. When I’m interviewing Horatio Sanz, I can stop midway through and say “I want to mention quickly blah blah blah” and then I’m back to the interview. It’s not like people are going to say “Ah, I gotta speed up [and skip the ad].”

Grantland looks like it’s getting more and more ambitious — you guys are doing a lot more video, you’re producing movies, and you have a TV show on ESPN now.

It’s weird that nobody gives us credit for this. I think we have the best multimedia site right now. I don’t even know who we’re competing with. I don’t mean to be conceited — we just do the most things.

I think the thing that gets us the most excited is just pushing, and seeing how many things we can do, and how the site can keep growing.

It’s a pivotal time for the site. At some point we’ve got to either start growing, or we have to figure out what’s going to happen.

So, about that. You have a contract that expires near the end of the year.

I do.

We just talked about all the things you’re doing. Do you think you could go off by yourself, or some place other than ESPN, and recreate all of this?

I don’t like the word “recreate.” That doesn’t make a lot of sense to me. Grantland has been the most important thing I’ve done now for five years. Everything I’ve done for the last five years has been geared toward the site. I think it’s a business. The frustrating thing is you have to keep growing to have a business. You can’t just say “Okay — we’re good, after three years — we don’t need more people.”

I just think Grantland’s at a crucial point now where we’re doing the site that we have now really, really well. And that’s been the case now for about 14 months. So now the question is, what does that mean to ESPN? I don’t know. I don’t know that it’s a me decision — it’s what does ESPN want from this site? Because if they just want it to say the same, it’s going to stagnate a little bit.

It sounds like you’re asking ESPN to give you more resources.

I’m not doing anything. I haven’t asked for anything.

But when you do — it sounds like what you’re going ask them to do is to invest more in your property, and you.

I wouldn’t say that. That’s a decision that has to come from them. They just have to think about what the goals of the company are. The reality is they make billions of dollars with TV rights. It’s always good to dabble in different things. But sometimes when you dabble in different things, they turn into something. I think you have a responsibility at that point to decide “Alright — something happened here. This is a really good thing. Now what do we do?” That’s not my decision.

But you’ve made some suggestions, presumably, to [ESPN head] John Skipper and those folks.

No, I haven’t, actually. I haven’t had a lot of contact with those people since last September.

That was the Goodell thing. Does that experience influence your decision?

I don’t know. What I care about is the people I work with. Those are the people who know how much time we’ve put into everything. And we’ve never had … we’ve always been understaffed, always. We’ve had to pick certain people who are just overachieving, people that care about the product that we have. And, you know — at some point you want to have the right number of people, you want to start adding verticals and certain things. And if you’re not prepared to do that, I don’t know what’s left.

So that conversation has to happen first. And then you have to have a conversation afterward about me, and what I want to do. I still feel like I have five years left, where I can work at this pace. In five years I’m going to be 50, and I don’t know how hard I’m going to be able to work. I know how hard I work now. I don’t know if it’s going to be sustainable.

I think they take it for granted. Not just how hard I work, but how hard everybody works.

This article originally appeared on Recode.net.

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