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What It’s Like to Host a Podcast With Hillary Clinton

A conversation with Longform’s Max Linsky, co-host of ‘With Her’

As one of the co-founders of Longform and the Longform podcast, Max Linsky speaks in depth (and, especially, at length) with writers, journalists and authors. But it wasn’t until this year that he finally interviewed someone who was no doubt on the show’s bucket list: a presidential candidate.

As part of a new venture with both Clinton and Linsky’s podcasting company Pineapple Street Media, With Her talks to people involved in the Clinton campaign — specifically, Hillary Clinton herself. The first episode was a 17-minute conversation between Linsky and Clinton in Miami shortly after her acceptance speech at the Democratic National Convention. Episode Two had Linsky interviewing her vice presidential pick, Tim Kaine. The third episode, again with Clinton, will be going online soon. These casual, off-the-cuff chats, thanks in part to Linsky’s podcasting chops, bring out the warmth and charm in his subjects, trying to show the real people amid the towering apparatus of a presidential election.

In the first episode, Linsky opened with a short — but for him, important — disclaimer: “I’m not a journalist, and I’m not impartial. I’m a small-business owner, and a huge supporter of Secretary Clinton’s. And I’m thrilled that her campaign is having me do this.”

That hasn’t stopped some, like Slate, from calling With Her “gutless propaganda,” adding: “If Clinton really wants Americans to get to know the woman behind the caricature, she’s going to have to start giving interviews to people who don’t work for her.” In an appropriately longform discussion over Skype, Linsky talks about those criticisms, what it’s like to meet Clinton and Kaine in person and whether he can tell if they’re really as genuine as they seem.

So, how did With Her happen?
The woman that I started Pineapple with, Jenna Weiss-Berman, started and ran all the audio stuff for Buzzfeed. Hillary came on Another Round that Jenna started there — that was last summer — and she was in touch with the campaign through that.

Jenna knew that they were interested in doing some kind of podcast. So when we started the company, she sent them a note that said, “I just started this thing. We’re making original shows, but we’re also making shows for other people, and if you guys are ever thinking about doing a podcast, we’re happy to be helpful however we can be helpful.” The initial idea was, “If you guys want advice on what mics to buy, we’ll help with that.”

It turned out that it was something that was actually pretty high on their list. They have a joke that [a podcast] had been on the whiteboard for a year and a half or something. It was something they really wanted to do, but they didn’t really have the people in-house to do it, and they do almost everything in-house. So, we went and talked to them about what our dream scenario would be for a show, and it went from there.

Image via Max Linsky/ Twitter

What did you pitch them?
We don’t know what a presidential campaign looks like, so if we could get to something that felt like stolen moments with her, that would be something we’d want to hear. The first idea was to give her a tape recorder, and she would just record herself on a plane somewhere. That turned out to be logistically difficult, but they wanted it to be her and they wanted it to be about what life on the campaign trail was like.

Her team decided you should co-host the show with her. She’s got to be the most famous person you’ve ever interviewed.
I did an interview earlier this summer with David Remnick, and in my little universe, that felt like some version of the Super Bowl. But yeah, [in terms of] pure fame and power, Hillary Clinton’s at the top.

How much advance notice do you get before a With Her taping?
That’s been one of the things that’s been so interesting. [Clinton’s episode] moved a couple of times. The one that I did with Tim Kaine was supposed to be in two other states before it was in Seattle. But the stolen-moments idea is actually how it works. Their schedules are evolving a lot — they’re like, “All right, I think we’ve got a 20-minute window on Monday afternoon,” and we find out on a Friday. It’s funny: I’ve definitely bought more last-minute plane tickets in the last couple of weeks than I have previously.

You’ve interviewed a ton of people, but what’s the nerves situation like before you talk to Hillary?
The nerves situation is high; the nerves situation is not good. It was also hard because, on Longform, those are long interviews, man. I tell people, “Budget an hour, hour and a half.” For this, we were on the schedule for 20 minutes, so I was really nervous about that.

When you finally sat down with Clinton in Miami, how did she seem?
She was amazing. She walked in and seemed genuinely happy to be there. One of the things that I was super-nervous about was that she was gonna walk in and be like, “Ugh, all right, here we go.” But she was into it. You know, I’d been thinking about those 20 minutes for many days and hadn’t really slept the night before — but those are the easiest 20 minutes of her day. Just a chance to sit down and talk to somebody — that’s a walk in the park for her. How relaxed she was made it a lot easier for me to be relaxed.

The popular impression of her is that she’s this robotic, on-message politician who’s not particularly spontaneous or warm. Did you go in thinking you would need to draw her out?
My assumptions were similar to what your assumptions would be. I was thinking going into it, “Man, I’m really gonna have to find a way to make her feel comfortable.” The reality is that she was so beyond that — she kinda drew me out. I didn’t catch any of the clichés about her. It just wasn’t my experience.

I interview filmmakers and actors, and they’re one kind of famous. My assumption is that politicians like Hillary Clinton project a different kind of celebrity. Is that true?
Kaine is, like, a legit mensch — he was super-unaffected. It did not feel that different than the conversation you and I are having right now — except that he had been in a thousand states in the last three days. It was a Friday night: He’d started the day in Wyoming, he stopped in Oregon, and was now in Seattle. He sat down and seemed like a guy who wanted a beer. He didn’t feel different than most people I’d talk to.

She’s a famous person. I found her disarmingly comfortable and warm. I haven’t thought about this very much, but now that I’m thinking about it, I can’t tell whether that’s her affect or whether that’s a byproduct of [me] suddenly sitting across from someone you’ve seen that many times. You and I have been seeing her on screens for 20 years, and there’s this element where it almost doesn’t feel real.

This is a stretch of an analogy, but when I was 17, my dad was doing some work in Egypt, and he brought me along. We took a day and went to the pyramids. I’ve seen one million pictures of these things, but the picture’s almost more real than the actual structure. So, it was closer to that: This is a real person.

Ultimately, is the mission of With Her to get her, Clinton, elected?
I don’t have a really good answer for you. I think [the Clinton campaign] finds the medium appealing in the same way that a lot of people find the medium appealing. It’s a cliché, but there’s this intimacy of sharing people’s voices. And I think they were interested in how that would fit as part of their larger messaging.

People have been asking me how I think about [With Her]. To me, it feels similar to Shonda Rhimes making that video before her speech at the DNC. I hadn’t met [Clinton] yet, and I found the video really good and moving. I think in its best version, this is something like that. But I certainly haven’t gotten a note that’s like, “This is about undecideds in Pennsylvania, Ohio, and Florida.” That’s not the way to think about it. I want her to win, and that was the original reason we reached out: If we could be helpful, then we wanted to be helpful. If it turns out that me talking to her [helps], then that’s a crazy thing, but I’m happy to do it.

So far, the podcast hasn’t delved into policy questions — it’s more about giving us a sense of who these people are.
I would be terrible at asking her policy questions. I do not understand that stuff very well, and there’s a million people who are way more prepared, knowledgeable and intelligent who would be way, way, way better at that than me. No one would wanna hear me ask her policy questions.

It reminds me of the podcast you did with the Cleveland Browns last season, which you’ve said was about understanding what football was like as a job. It seems like you start with a curiosity about how something works.
[Running for president] sounds crazy. That’s the thing that I’m genuinely interested in. What does she do? Does she ever get downtime? What does she do when that happens? Like, does she ever watch BoJack Horseman? I just have no sense of what that’s like. So, yeah. there’s a genuine curiosity about that. But there’s also a truly selfish part of this, which is, “You know what seems really fun? Cracking jokes with Hillary Clinton.” It’s a weird, exciting way to spend an afternoon.

Did the Clinton campaign put any restrictions on what you can’t ask?
It hasn’t gone like that. The caveat at the beginning of the first one [about not being a journalist and not being impartial] was really important to me — I don’t think the show can be successful if listeners aren’t clear about what it is. It wasn’t a hard fight, but it was something that I made very clear that I needed to say at the top. I’m not a journalist, and I don’t want anyone to think that this is journalism, you know? It’s not. These podcasts are going out on — this is for the campaign. But I do believe pretty strongly that that doesn’t mean it doesn’t have to be interesting or honest or real.

There’s been criticism of With Her, the complaint being that she’s using it as an end run around talking to journalists and doing press conferences. I’m guessing your response is that the podcast isn’t meant to be a press conference.
That actually is not even quite my response. My response is, I am running a business. We’ve got a couple employees — we started two months ago — and I just figured out how to get everyone health care last week. I’m really not paying super-close attention to the day-in and day-out of the presidential campaign — nor have I been doing that for years. I feel like that [criticism] is [from] people who have been doing that job. If you are on the Hillary Clinton beat, your job is to try and get an interview, and you should do whatever you need to do to make that happen.

I wouldn’t even go as far as to say, “Well, this is a different thing, and what you’re doing is this, and what I’m doing is that.” That’s not how it feels to me. I don’t feel very comfortable being, like, “Let me tell you about what life is like for a political reporter trying to cover Hillary Clinton.” I have no idea, no clue. I can tell you what it’s like to try and make a podcast for her. I know a lot about that now. That [negative] response certainly wasn’t surprising, but it also felt to me like a conversation that I’m not really a part of.

How much control does her team have over the final product?
We give them a draft — they definitely listen to it [before it goes out]. The cuts have been super-minimal, and they’re all pretty smart. Turns out that the people who work for her on that campaign are really good at their jobs. To be totally honest with you, it’s mostly editing me out — most notes are, “Less Max.” [laughs]

But I don’t want there to be any ambiguity about it: We do not have full editorial control. If they desperately want something out, then it’s probably gonna come out. But it hasn’t been an issue.

You’ve interviewed Clinton twice now. Was she different the second time?
I know that she likes to say that she’s not a natural politician — and there’s certainly a chance she’s playing me — but I think she enjoys it.

That’s what interesting to me about interviewing famous people. They’re so magnetic and charming and engaged that I think, “This might all be an act — but if it is an act, it’s done so authentically that it almost doesn’t matter.”
Not to get too meta or anything, but I’m a fan of your work. I was psyched to talk to you — but also, it would be great if I didn’t come off like an asshole [in this interview]. So, I think it’s all those things.

But she does have that thing. We ascribe it to politicians, but my best friend from college is like her in that he never forgets anybody. It’s a gift — and it’s a gift that he’s not afraid to use. But you’re right to point out, like, where is [that genuineness] on a spectrum? I’m sure, on some level, she knows that the podcast will be better if she doesn’t sound like she hates being there. But, also, I think she doesn’t hate being there.

Yeah, she might know that it’s smart for her to sound interested in talking to you. But she might also be genuinely interested in talking to you.
Which is also true of running for president. You don’t run for president if you don’t wanna be president, which is a pretty awesome job. There’s strategic ego stuff built up, but you also better like talking to people. Otherwise, that’s a pretty long act.

We’ve talked a lot about Clinton. But what was Kaine like? I’m guessing he’s less intimidating a proposition than she was.
It was a different thing. If some magazine had come to me — “We wanna assign you a Tim Kaine interview” — I would’ve been probably a lot more nervous about it. But coming off the heels of interviewing her, I was more like, “Well, it’s not like that.”

But, also, he rolls light. He had a couple of people with him — they were super nonchalant. He had an advance person in Seattle, and she was bored ‘cause he didn’t ask for anything. Literally, all he asked for was lemonade. Also, he was really game — he sat down and cracked some jokes before we started recording. He made it a lot easier. That’s been true with both of them.

The culture has decided he’s essentially the slightly dorky, adorable stepdad.
That plays. That was totally my impression [after interviewing him]. Maybe Tim Kaine is a huge [jerk], but I don’t think so. He certainly wasn’t with me. It’s the same thing we were talking about, man: It’s a hard act, and he didn’t seem like he was acting at all. He walked in, his shirt was open, he was taking off his tie, he was done working.

People have a suspicion about sponsored podcasts. They think they’re somehow inauthentic — or that the listeners are being sold something rather than it being a genuine experience. What do you say to that?
I think there’s three pieces to that. One is, a means of balancing [that impression] is transparency. So, again, I think the worst-case scenario is that someone listens to [With Her] and thinks it’s not for the campaign and then realizes later that it is and feels duped. That’s a terrible outcome.

The second is to not ask stuff that I’m not genuinely curious about. That doesn’t mean that they are the hardest questions. “What time did you wake up this morning?” is not gonna make anyone quake in their boots, but I’m interested in it.

And the third thing — the most important thing and, honestly, the thing that I care about the most and is the only measurement of success — is, “Do people wanna listen to it?” If you could be transparent and people wanna listen to it, then that’s the goal. If it’s boring, people aren’t gonna listen.

Because podcast audiences skew younger, is the Clinton campaign hoping With Her will cater to a demographic that isn’t entirely onboard with her?
I can tell you, honestly, I have not had that conversation with her. But I think they think of podcast listeners as a community that they weren’t reaching as much as they wanted to. And I think the Another Round appearance, which made every “Top 10 podcast episodes of the year” list, was probably a very significant benchmark for them. That probably opened their eyes quite a bit. They haven’t said this to me, but I’m assuming that sharing her in that format — and watching people respond to that episode — changed the way they were thinking.

One thing that is very clear is that the most finite, valuable resource they have is her time. For all the money they bring in, the most valuable thing they have is her 24 hours. And so I do think it’s really remarkable that they can view [With Her] as a valuable use of their time. You know, 20 minutes is a lot with her. I had this moment before the first one where I sort of said something offhand to someone from her campaign. I was like, “20 minutes is pretty short for what I do.” She said, “Make it work.”