Conversations With Will Cain, Matthew Berry, and ESPN Executive Norby Williamson

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I did an ESPN carwash speaking to talents and executives earlier this week. On Wednesday we posted a podcast with 6PM SportsCenter co-host Kevin Neghandi. Yesterday we ran a Q&A with Burke Magnus, EVP of Scheduling and Programming, who oversees sports broadcasting rights acquisitions. Below are conversations with Will Cain, Matthew Berry, and Norby Williamson (EVP and Executive Editor, Studio Production). Early next week we will publish conversations with Scott Van Pelt, Ryan Spoon, and Marcia Keegan.

There was a segment on Le Batard show a little while back where he said that if you want a job at ESPN now, be a conservative. We don’t need to rehash the whole conversation, but there were a lot of opinionists who are left-leaning. You are not bleeding heart. Do you think in a weird way that created an opportunity for you being different from what their core strategy was over the last couple years?

Cain: Yes. I don’t know what the core strategy was over the last couple of years, but I remember when Fox News was created some 25 years ago or so, and this quote was probably in the last 10-15 years. George Will, a famous columnist, said, “Roger Ailes discovered a wonderful niche in America: half.”

I think that I have a point of view that, although unique in the Northeast and unique in the media, and perhaps even unique within this company at times, is not unique throughout this country. And I’m not going to call that a political point of view. I’m going to call it a general sensibility, because it applies to culture, politics, maybe even parenting, and certainly in sports as well.

What’s your ultimate aspiration in broadcasting?

Cain: To own this network and the entire media industry.

What’s your realistic ultimate aspiration?

Cain: Within the halls of ESPN, whose career I really admire and who I think has done a good job of building a multi-platform business and is an absolute star at what he does is Stephen A. Smith. Stephen A. has a voice that I think is independent. He’s not a follower. He’s not contrarian for contrarian sake. Stephen A. Smith says what he thinks and thinks what he says. In this industry that has been rewarded by having a platform on radio that he has built an audience. He’s obviously a star on television. I would like to be someone who has a presence on TV and radio.

I love this medium. I love radio. There is none better. There is not one in writing. Not one online. Not one in television that is as good as the platform that is radio. Proven, over decades, to establish a relationship with audiences that is deep and meaningful. And that’s the kind of relationship, honestly Ryan, that I want to have with an audience ultimately. It’s not just, ‘Hey here’s my hot take, here’s my big opinion.’

I think there’s more meaningful and fun places to go with an audience, that truly this is the only medium you can get there with.

What outlets and people do you like to read before you prepare for your show, besides The Big Lead obviously?

Cain: I do read The Big Lead — I’m not saying that because you’re sitting with me. There’s preparing for life and being well-rounded and having the ability to draw connections or understandings, to whatever it is your specialty in life — finance, sports, politics. There’s things you need to know, and I read the Wall Street Journal and New York Times on a daily basis.

And then, for my specialist stuff in sports, I do read ESPN, The Big Lead, For the Win, and The Ringer. Those are my daily rotations, and then of course whatever it is I’m talking about that day I’m poring for stats and analysis.

If you were a talent scout for ESPN, who are some people under 40 that you think would be good fits here?

Cain: That’s a difficult one. Who’s a good fit that’s not at ESPN already? Let’s ask that question another way. Who do I listen to? Whose perspective do I listen do that doesn’t work for ESPN?

I read and listen to Clay Travis, I think he has a unique voice.

Do you think he’ll work here soon (laughing)?

Cain: That’s not my call. But don’t think that’s just confirmation bias from me. I read and listen to Nick Wright, who I don’t think probably likes me based on one or two tweet interactions, but I don’t care.

See, I’m not in this to make friends. I’ve got friends. I grew up in Sherman, Texas, and my best buddies still grew up in that town. I’ve got friends in life. I didn’t come here to be well liked. I came here to have fascinating conversations. To share some aspects of my life. To connect with people.

Call me an ass for this but I do that through discomfort and challenge, not through, ‘Wow man, you were right all along.’ So I listen to and seek out people who disagree with me.

There’s this Navy Seal out there right now that I’m so into. His name is David Goggins. He’s this guy who weighed 300 pounds and hated his life and said, ‘How do I get to where I want to be in life?’ He couldn’t swim even. He decided he wanted to be a Navy Seal. They told him he had to lose like 150 pounds in four months to even try out.

He did it and he became a Navy Seal and now he’s an ultramarathoner– after not even liking to run two miles a week he runs 100-mile races. His whole thing in life, if you follow him on Instragram, if you listen to him on the Joe Rogan podcast, his whole point is discomfort. It’s pain. That’s where growth happened.

I think that’s physical, I think that’s spiritual, I think that’s intellectual. So sometimes everyone is like, ‘Will are you just trying to be a contrarian? Are you just trying to get attention?’ No. I can honestly say I’ve never said one thing to get attention. I do like to challenge. I do like to be in that discomfort zone.

Do you see yourself delving into line analysis or are you mainly only going to reference gambling within the parameters of fantasy?

Berry: I think I will reference gambling within the parameters of fantasy. Look, I will do whatever the company wants me to do, and if it’s an area that they think could be beneficial and a fit for my analysis then obviously I will do it.

But, I love fantasy football. That’s sort of what I do. And, I think there’s a lot of analysis done around lines and spreads that can be helpful and insightful to fantasy players. So I think I’ll incorporate that more blatantly. I’ve done it for awhile, but maybe it hasn’t been overt and now I can be about that. But no, I’m a fantasy football guy.

I am pro sports gambling. I’m excited about it the Supreme Court decision. I think it’s great for everyone involved in sports. The leagues, the players, the media partners, the fans.

Why hasn’t fantasy basketball taken off in the way that football and I guess to a lesser extent baseball has? 

Berry: My impression is that we actually have more fantasy basketball players on ESPN than fantasy baseball players. Fantasy baseball is a legacy game. It was the very first fantasy game I ever played, and I think that’s true for a lot of people.

I think one of the things that fantasy basketball suffers from is the timing — what fantasy baseball has going for it is it starts up in April and you draft in March. There’s nothing else going on. With basketball you have to draft in October and you’re in the middle of fantasy football season. It’s a big commitment.

I will tell you that daily fantasy sports has been a big boon to both fantasy baseball and fantasy basketball, because the complaints I hear about those two sports is it’s too long and too much of a commitment.

But, I would call fantasy basketball an ascendant game. It’s actually growing for us here. Candidly, all of our fantasy games are going. I can take no credit for this whatsoever, but our fantasy app has been tremendous for the growth of all of our games.

Has anyone sent you a check for helping them win in fantasy or an invoice for making them lose?

Berry: No. People say both on Twitter, that I cost them their league or people who said thank you for helping me. I have had people donate portions of their winnings in my name to charity, which is cool, including to the V Foundation. I think that’s awesome.

There was a thing I wrote about last year, that was started by a guy named Michael Gehlken, who covers the Raiders for the Las Vegas Review-Journal. He had an idea, and I sort of amplified it, about donating money to the charities supported by fantasy players who helped people win their leagues.

We did it two years ago, we amplified it this year, and it seemed to take off in a big way. Todd Gurley represents Shriners Hospital for Children and they raised over $20,000 just in his name from fantasy players. If you go through my Twitter likes, you’ll see I retweeted or liked a bunch of people who thanked me or Michael Gehlken for the idea and donated in players’ names.

It was super cool and it seemed to take on a life of its own. Michael was trying to do a story to figure out how much each player raised. He talked to a spokeswoman for the Shriners Hospital and asked about Todd Gurley. The woman there answered and was like, ‘We’ve gotten a ton of donations for him …… did he die? What happened?’

Norby Williamson

Williamson: My ultimate goal is to increase the audience.

As in to increase from where it is, or to increase from previous year’s SportsCenter?

Williamson: Yes on everything. When you launch a new show — we’ve done this over time a lot of different times — you’re changing habits and viewers’ expectations. For years, SportsCenter was in that window. The available customers and fans had an expectation. Anytime you launch anything new in a window, there’s an adjustment period. Sometimes it’s immediate and it’s up, sometimes it’s flat, sometimes it’s not. You gotta see growth.

Since we launched Get Up to where we are, we’ve seen growth. Is it to the point where I want it to be at the moment? No, but I’m optimistic that as we continue to push that show forward and tweak and innovate with that show that we’re ultimately going to grow audience and write more ad sales on it. And that sports fans will become as passionate about Get Up as they are about SportsCenter.

Other than grow the audience, what is your goal for High Noon?

Williamson: Uh, grow the audience? Showcase two talents [Bomani Jones and Pablo Torre] that I really believe in and I think have a good relationship. Again, I try not to make analogies to other successful things, but we’ve had other shows based out of [Erik] Rydholm productions for a lot of years on the air. The two guys at 5:30 [Kornheiser and Wilbon] had a relationship and PTI has been a very successful show.

Bomani and Pablo have had that relationship. They’ve conversed and worked together and done different things — whether it’s SportsCenter, Bomani’s radio show, Around the Horn, whatever it may be — and I like the content treatment that Rydholm has created and I believe in those two talents and the goal is to really take and grow that First Take audience, which we’ve had a tremendous run on ESPN.

It’s tricky to figure out how to word this question, but there’s been a lot of research that shows that second generation Hispanics in America respond well to Hispanics on television who speak English. You’ve had success with Dan Le Batard with his radio show and Highly Questionable, but I’m wondering if you have any plans to showcase that demographic to grow with younger Latin American viewers?

Williamson: We have to do a better job. Whether it’s in life or television or whatever, people want to see people that they can relate to. It doesn’t have to mean that men have to look at men or certain demographics, but we need more Hispanic talent on our air.

We’ve made some good strides. You look at John Sutcliffe or Dan Le Batard or Jorge Sedano — we’ve had some success, but we need to fast-track that. That’s been a focus for awhile, and to be honest with you we’ve done okay but not great. I don’t think it’s just not finding talent, and you were smart to bring that up, we have Deportes and because we have Deportes that gives us a break finding resources in the company both in front of and behind the camera who are bilingual.

I think there’s a thought process, if you go back a few years ago, how do you get that second generation, that fanbase, that happens to be Hispanic but wants to consume the sports in English, and not to segment that population? You look at Monday Night Football or the NBA, we over-index of Hispanic sports fans on those big properties, but we should. You had 16-18 million people watching Game 7 — our Hispanic composition watching that window was off the charts, but it should be.

I think our goal is when we get that big influx into our studio shows or on our network, how do we convince that fanbase that we are the destination for you? That you’ll come back and try SportsCenter or First Take or PTI. It’s a tough execution sometimes when you’re trying to court a certain demographic.

It goes into your marketing. What marketing message do you put out? What are the faces? What are the voices? What’s the content? What’s the subject matter? It’s not an easy fix. But to your point, we all know the population of the country, where it’s going and where it’s headed, if we don’t do a better job of being more welcoming destination for that fanbase, we’re not going to have an opportunity to increase that audience.

Do you dispute the idea that the line in the press release that said 6PM SportsCenter ratings were up 9% year-over-year was a shot at Michael Smith and Jemele Hill?

Williamson: Yeah. Why would it be a shot at Michael and Jemele? Was it a shot at the coordinating producer who was working on the show? Was it a shot at the executive whose decision it was to oversee the show?

It’s a critique of all of us. I don’t look at it as shots. I’m proud we tried that at 6 o’clock. Look, I’ve been here a long time. I’m proud we tried the phone. That was an unbelievable failure but what we learned from doing that ended up pushing our digital business in a place we wouldn’t have pushed it.

Look, I’ve made more mistakes myself in decisions I’ve made just because I’ve been here a long time than collectively most of the other people you’ve talked to today. But if we’re not taking big swings, what are we doing?

We should take big swings. By the way, if it’s not resonating with our customers … We’re in the business of getting as many people to watch as we can. Within the brand and the vision of what we’re doing. So clearly we had to make some strategic changes on that show and I think that was the right thing to do given the time and where the show was.

It doesn’t mean that it was a failure. It doesn’t mean it was a shot at anybody. The facts are the facts. I’m very unemotional about some of this stuff. You win games, you stay in charge. You grow your audience, you get rewarded.

[This was the day Keith Olbermann returned to Bristol for the first time since 1997; this was taped before Roseanne was fired from ABC.] How do you feel about Olbermann’s anti-Trump tweets from a few months ago?

Williamson: A few months ago? It was more than a few months ago, I thought.

I don’t know. Six months ago? 

Williamson: I think it was a little bit more than that, actually. To me, there was a demarcation point. I think you get an opportunity to sort of move forward. That’s how I’m judging it. Am I wild about everything? No, I’m not wild about everything.