Adam Conover on the myth of good billionaires and why YouTube isn’t going away anytime soon

The A.V. Club: What makes this a good representation, or entry point, for people discovering your show?

Adam Conover: That video was my first attempt at doing a YouTube-style video essay. I just woke up one day with a fire in my belly about this Yvon Chouinard story about how he’s, you know, the most wonderful billionaire in the world because he donated his Patagonia company to charity or whatever. I had heard stories like that before. And I knew what normally happens, which is that the billionaire is using the charity to shield money from taxes while maintaining their control. No one was covering that angle of the story; it was literally just, Oh, this guy’s so good! I did a little bit of looking into it and found the one or two journalists who wrote slightly critical pieces, and I turned it into a video. 

Also, I just so happened to be, at that time, booked to do an emcee gig at the Crystal Bridges [Museum Of American Art] in Bentonville, Arkansas. I flew in and was going, hold on a second. Why is there one of the grandest art museums I’ve ever seen in this spot in Arkansas? How come there’s a direct flight from Los Angeles to Bentonville on American Airlines? Why are they paying me to come out to introduce this one event?

l got there and I started looking around, and I realized it was Walmart town—and that the entire town is essentially a cathedral to Sam Walton. They have a Walmart museum where they have his office preserved as though he were about to suddenly walk in through the door and sit down at the desk.

So I was like, hold on a second. This is a monument to this one billionaire, who was able to write his own story because of his money. And he was able to write it kind of genuinely, because he literally did make the town a better place to live for all those people. Of course they loved him: He brought a world-class art museum, his family has built miles and miles of bike trails, they poured money into this town. 

Why do they make this one town prosperous? Because they destroyed the downtown of every other town in America, via Walmart. So I was like, my God, this is emblematic of the same story as Yvon Chouinard. But liberals love Yvon Chouinard, and they don’t love Sam Walton. It’s purely a cultural thing, because Chouinard flatters them, he’s an environmentalist, etc. So, I just started filming while I was in Bentonville, like, oh, maybe I’ll use this for a video, and then the script very quickly came together.

Currently, I’m trying to grow my YouTube operation. This is part of my business as a comedian; this is my outlet now. But [for] this first one about Yvon Chouinard, I had no schedule. I had no monetization plan. I was just pissed off and wanted to say this thing, so it’s got a purity to it in terms of my expression as a comedian.

My producer Tony Wilson, who filmed and edited it, really nailed the tone and the timing. It was a massive hit, multiple millions of views very quickly. There was almost nothing on my channel before, and it went from that to half a million subscribers in a week just because of that one video.

AVC: Your YouTube monologues and podcast now live together on the same feed. Do you approach them differently?

AC: A YouTube monologue lives or dies by the algorithm. It’s got to “catch algo” or it doesn’t have any traction. So I’m usually trying to think: What is a topic that is going to make people click, that they’re going to be interested in? A lot of people complain about having to tailor stuff to the algorithm, but it’s no different than trying to make something work on cable television. Your job is to figure out how to make it work for the format and for the audience. 

The podcast has much more of a weekly audience—people are tuning in because they like the show and they trust me. That means we’re freer to do in-depth discussions of stuff that really interests us. It’s a balance, because YouTube is now the most popular podcast app, so there has been a little bit of pressure to make the podcast a little bit more YouTube-friendly. The barrier has really broken down. Maybe things are moving towards a synthesis. You could catch me back in a year and see what’s happened.

AC: First of all, this is one that people told me, in real life, that they heard. If you know anyone who works on the internet, you should know that the most important thing you can do, if you engage with their work, is tell them about a specific piece of theirs that you saw on the internet and enjoyed. You publish online, you get your view count, you get your comments, you get your likes and whatever, but you’re always sort of like, did anybody even see this? Until someone in your literal life says, “Oh hey, I really liked this one.” 

I guess I can’t comprehend that there are people opening up Apple Podcasts and listening to the whole thing. That individual experience can be so powerful, but it’s sort of invisible to me as the maker, right? People said they heard this one, some people said it changed their mind about some things. That feels like a demonstrable impact in a way that no view count does. 

What I love about this particular interview, apart from the reaction, is that, you know, the loose theme of the show is that I talk to experts. I love talking to scholars and journalists and authors and people who do research and then report on their research—and what I love even more is talking to someone who has on-the-ground expertise and lived experience. Dr. Kushel has experience with pulling people out of homelessness and working with unhoused people. 

That sort of expertise is incontrovertible in a way that research is not, you know? I love having someone come to the show and say, “This is my experience. This is what I know works. I can tell you this works because I have done it.” A podcast is an intimate thing. I’m bringing this person into intimacy with the audience, into a sort of closeness right to their ears.

She was someone who I was really proud to be able to bring to the audience that way. There are a lot of issues in the country where people have different policy choices, you know, different philosophies. Homelessness is an issue where, if you start engaging with it directly and just go fucking meet some homeless people and talk to them and find out why they are on the street and what the barrier is to housing, it will transform the way you see it, and it will transform what you think the solution should be. 

I had that transformative experience because I did homelessness volunteering for many years; it changed my life and how I see the issue. Not everyone has time to do that. If I can bring the audience a little bit of that, I think that’s really powerful. To bring them into communion: “Hey, here’s somebody who has fucking been there and knows.” That’s what I love about this interview.

AVC: The topic of this episode doesn’t initially sound all that essential, until you find out about the sheer amount of research that ContraPoints has done.

AC: The main reason I love the episode is I admire Natalie more than almost anyone else on the internet. I am such a genuine fan of her work. She is an absolute original—her process to make the videos is insane and beautiful. She does all of it herself, it’s entirely a one-woman operation. She is making incredibly astute points.

She had this long video about Twilight. You think, oh, it’s a pop culture analysis, like other people do on YouTube. But by the end of the video, I was like, this woman is doing honest-to-god original philosophical writing. She even has a little joke: “This is what I did instead of doing a PhD thesis dissertation.” That really is the level of philosophical work being done in the video. It should be watched by academic philosophers and they should discuss it at conferences.

This is incredible original work, and she’s doing it on YouTube in a format that is somehow getting millions of views, from average people—she essentially advances a new theory of the gender binary at the end of the [Twilight] video. You see how she gets there, and how it’s integrated with gender dichotomies of dominance and submission, pursuer and pursued. I was like, I want to have Natalie on the show and talk to her about anything. So we ended up talking about this Twilight video, and she expanded on a lot of those points, which was really an honor for me. 

That’s why I chose this episode. I can’t tell you I’m brilliant in it; I can just tell you this is an interview with one of my favorite people working in any medium today. 

AVC: How did this episode come to be? Did you wake up the morning after the election and think, “I have to talk to Jamelle about this?”

AC: Jamelle is one of my favorite writers and thinkers about American politics. I had wanted to have him on the show for a long time. But I woke up Wednesday and knew I wanted to do a post-election episode. I opened up Bluesky and looked at his feed, and he had just posted, “I’m in LA tomorrow and I have a free afternoon, what should I do?” I emailed him and I texted a mutual friend to ask him to do the podcast. Lo and behold, he was down. 

It was complete happenstance, and so we got his very raw reaction to the election. He hadn’t even written a [New York Times] column yet. It was incredibly insightful and cathartic to talk to him about it and get his perspective. Especially because it wasn’t just, “Here’s how Trump won.” It’s his historical perspective: Here’s how things are likely to go, here’s how this fits in with the rest of American history, and why it really feels like we’re entering a new era with the second Trump administration. 

AVC: How did you feel recording in that raw, immediate post-election space? Jamelle even says at one point, “Most of human history is a catalog of misery.” Yet you’re still responsible for packaging that into a digestible episode for a broad audience. 

AC: I just sort of let my instincts take over. I play the interviewer pretty well and keep it moving, but what people want is the unfiltered, unedited front-to-back conversation. I’m mostly trying to be honest about my own reactions, and be a mirror to the audience and their reaction. We released the episode outside our normal schedule, part of which was to have that immediacy: “Where do we go from here?” It’s about matching the audience’s emotional state. I don’t really need to “package” it, as a comedian, to make it entertaining, because it’s like, no, the audience wants this right now. They want this catharsis. 

I’ll go on record as saying that Jon Stewart is the most talented person to ever sit in the late-night chair. And the reason for that, in my view, is that his emotions are so front and center. He’s having an honest emotional reaction: Every time you watch him speak, you can tell he gives a shit about what he’s saying. You do not get that from most people doing late-night, even very talented performers. Stewart is present, he is in the room with his audience, and that means he is in your living room, too. It’s an emotional connection. 

That’s what I aspire to do, and I’m continually trying to get better at it, to make my work less stiff and more genuine. It’s this process of trying to strip the artifice away and just fucking be yourself and be present, and that’s hard to do, for the same reason it’s hard to meditate and not think about other things. In that episode with Jamelle, I was able to simply be myself and be in the moment, and know that that’s going to work for the audience. 

I really feel like I had a breakthrough giving you this answer. 

AVC: What else do you want people to know about Factually!, and where is it headed from here? 

AC: What is very clear is that YouTube is replacing vast swaths of television. That was already happening, but I think the election made it incontrovertible for people. News, talk, politics, so-called comedy-variety—it’s all happening on YouTube. So people are watching the type of content I do more than ever. The last couple years, for me, have really gone from, “Hey, the podcast is something that I do because I enjoy doing it, a nice way to make some money and stay in touch with my audience” to becoming, “Oh, wait, no, this is actually the audience’s main connection with me.” This is something I can do at a high level week in, week out. It can never be canceled. 

I still want to work in TV again, but I could pitch the best late-night show ever and take it to the four or five remaining buyers in television, and they would say, “I don’t know how to make money on that.” Then I can go to YouTube, where people are watching this kind of content by the tens of millions, and I can get as many views as all of these other legacy late-night products, and make as much money as I was making on television.

Now, I don’t have the budget that you would have on television, and that’s the main problem: I can’t employ the same number of people, which means it’s harder to make as high-quality of a product, and I’m resentful about that. But I can make the thing I want to make. A lot of comedians have realized that about podcasts.

The last year, ending with the election, has been my moment where I’m like, oh, this is mass media now. It’s also impressive how much the boundary between YouTube and podcasts has broken down specifically over the last year. A couple years ago, I couldn’t get one of my previous podcast networks to even consider helping us make video content for social—and now, if you’re not on YouTube, it’s as if your podcast doesn’t exist. There’s been a lot of growth for me, and it’s only solidified that this is where it’s going to happen.