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Rick Wilson
Hey, everybody, it's Rick. Welcome back to the Enemies List podcast and we're doing our Q and A's. We have had a lot of questions this in the last few days and the last couple of weeks. A lot of them are about Los Angeles, and I want to get right to them. You're going to see me reading these because I can't memorize them all. Let's go to Kathy in Montana. With rising authoritarian rhetoric in the U.S. do you think the guardrails of our democracy are holding? Are we whistling past the graveyard? Well, I don't know if we're whistling, but I can see the graveyard over the next hill. We better keep fighting back. And I mean that in all sincerity. Last week was a bad, bad, bad, bad week for this republic. It's a terrible week. Deployment of active duty military forces against American citizens, the assault on a United States senator by the thugs who work for Kristi Noem. None of this is good stuff. Trump is now expanding the role of the military in other cities. He did his missile parade. He's threatened people for criticizing him more and more. All of this is accelerating into a very, very dark place. I don't want to scare you, but we're in a bad spot and it's up to all of us to keep fighting and to stay up, stay, stay focused, stay engaged, and not let them scare you into submission and silence from Todd. My wife and I are thinking about having a kid. If you were me, would you wait? No, no, no. Honestly, don't wait. I had two fabulous children. I had two beautiful children. We couldn't do more. It was what it was. If you're young and, and, and you guys wanted, are thinking about kids, have babies, and if you can do it, do it. You won't regret it and you won't get any younger. So after my divorce, I did not choose option A, which is the standard male American option, which is to go and find a woman 25 years younger than you. You know the cliche stuff, right? I know guys my age. I'm 61. I chose an absolutely fabulous woman who is the love of my life. And she's 10 years younger than me and looks 20 years younger than me. Fine. But a lot of guys my age who are on their second and some on their third marriages are having babies and they're tired. You will not be as you will. You, you, you will never have as much energy the next day as you had the day before. And look, I also think having children is a sign of hope and optimism and a commitment to going forward. Too many people are, are, I think, convinced that the darkness of this world is too so impending that they, they don't, they don't want to bring a child into it. And the only way we solve the darkness is to keep going. Don't not have kids because Donald Trump is a dick. This is from Ben in Florida. The protests in Los Angeles and elsewhere shown a generational divide on what activism itself looks like. What does that signal about where the political energy is going? Look, there's a long and old political truism and that about young voters, and it's young voters don't vote. It is still mostly true. Young voting numbers have gone up a little bit, but in part they went up because of Donald Trump getting more young voters to vote for Republicans. Look, you want, you want political energy. The idea that it's just going to be that young voters are, and young activists are going to somehow magically fix everything is ahistorical. I want them involved. But there is also a role in, in our politics and our culture for wisdom and experience and knowledge and judgment. If you combine those things with energy and engagement and activism, I think you have a powerful political movement. But that's not where we are right now. The Democratic Party has been suffering for a long time by the belief that they don't like the working class of America and Steve Bannon and Donald Trump. And a lot of these people have converted that. It all strings back to Roger Ailes, who helped create Fox News, but before that, he helped create Richard Nixon. And Ailes was a brilliant architect of working class rage because a lot of working class people in this country have been fucked over royally again and again and again and again and again. And Roger realized you could build a TV network that talked to those people and made them angrier and you could convert that anger into political power. The Democrats struggle with male voters is real. It's. It's real. A lot of people tried to in the last few weeks say things like, we need $20 million to study how men vote and behave here's how you start with getting those guys. You stop insulting them and stop calling them all monsters and rapists and sexists. Stop diminishing boys and men. We've talked about this before. Make them a part of your coalition. Don't make them an enemy because right now they feel like the enemy. And you know what people, when you tell somebody they're a villain enough times, when you tell somebody they're a bad guy enough times, you know what they do? They look for somebody else. They go and find somebody else. They go. And when they're, when the door opens somewhere else, they run to that door. And it's important to remember that young voters, men and women, Trump appealed to them in a lot of ways because the Democratic Party didn't feel like it communicated with them. Didn't feel like it communicated with what? With their needs. And Democratic Party is famous for. We're going to focus group this and we're going to come out with a poll and it's going to in 2021. My colleague Reed Galen and I were in on this call with a bunch of big Democratic donors and operatives and these big groups. This very well meaning poll. She's like, well, we've pulled it. And the only thing in 2021 people care about is prescription drug coverage. The fuck are you talking about? Capitol is on fire two weeks ago. This election's about democracy. And in 2021 and 22, younger voters got engaged because they felt like somebody was talking to them about this world screwing them over and this world being dangerous for them. And it worked. That was a combination of the high experience side and the youthful energy side. Democrats need to do a lot more of that. It's a very tough question, longer than I can answer on this Q and A and I've been a little discursive on this answer. I admit activism without strategy is just noise. And strategy without activism is this lifeless object. You need to find a way to bring those two together. We'll be right back.
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Rick Wilson
And now back to the show Russ in Arizona in the In a world where facts are increasingly optional, what role should political media like yours play? Are we explaining the fire or trying to put it out? The kind of political media that that we engage in here at Lincoln Square is post big media. Major media institutions are dying. CNN is about to be completely gutted by the new CFO who's now the CEO who has promised to cut this the debt there. They cut it from 52 billion to 34 billion. They're going to cut that debt to zero, which means they have to destroy the network. CNN is dying or dead. Network news is sort of a vestigial idea. Major newspapers are, you know, the Washington Post is now Jeff Bezos and that is largely, I won't say pro Trump, but it is Trump adjacent. You have a few outliers in the mainstream media today. The New York Times is still a phenomenal enterprise even though it both sides the shit out of itself every day and wraps itself in knots. The Atlantic is probably the best single publication in the country right now for news. It's more analytical, it's more in depth, it's more long range stuff. But it's astounding. I, I, I'm jealous of them every day But a lot of where the news energy is going is on substack and podcasts. You know, we started the podcast at the Lincoln project in 2020, not because we were like, oh, let's do a podcast like every other guy does. We did it because our polling showed us that people were getting their news from podcasts. We saw those polling numbers and we were like, well, if people are getting 65% of people told us they were getting their political news from podcasts, why not talk in that space? Donald Trump proved that case out in 2024 by going on Joe Rogan and Theo Vaughn and the Nelks and all these other big, big podcasts where they were able to bypass the media filters, talk exactly about what they wanted to talk about. People like a more direct, engaged feel. They like to talk and think about things that they've heard directly, not inuated by a lot of media positioning. You'll see a lot of stories in the New York Times that are very well reported, but you can see that the editorial thing is to try to make it. Donald Trump ate a live baby on the White House lawn. Democrats leapt to criticize him. And they equivocate. They make both of those two things equally bad in their sort of tonality. There is a creation of a new media emerging right now in this country. And the media, the political media in America has gone through seven or eight phases since our founding. We'll be right back.
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Rick Wilson
And now back to the show. In our founding, political media were with two things, speeches and hand bills, like one page flyers, basically. That lasted largely up until of widespread mechanical printing presses. So we went through newspapers being very political that were like party newspapers that were a big part of elections. Fast forward about a hundred years to radio, which influenced political life in America and around the world very strongly. Adolf Hitler came to power in part because of radio. Stalin used radio. Roosevelt used radio. Radio was a transformative media technology that could reach many, many more people at a de minimis cost. After World War II, television emerged, although in a weird little rabbit hole. Adolf Hitler in Berlin. There was a small, mostly for the elite Berlin Nazi cable television channel during the war.
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Rick Wilson
It's so crazy. You can go down that rabbit hole. I'll put a link to it somewhere. Jump ahead to television. The widespread adoption of television in the 1950s in America, which brought us political television advertising. Cable comes along in the late stage, 70s, mid-70s to late 70s, depending on where you are in the country. Cable makes it even more targetable. It becomes the political game space. Both hate advertising and the emergent cable news world. That cable news world goes to Digital in the 2000s. Talking to voters on digital communication now, whether you're serving them an ad on their YouTube page, their Facebook page, into their phone, on their LinkedIn, wherever it is, that's the wave of the moment. And the news structures that you were used to for 30, 40 years are still sort of in the cable era. They're trying to transition to the podcast and digital advertising and digital advocacy era. But there are, you know, the Republican party and the porn industry always adopt new tech first, and they've been very fast about building a vast, enormous, super powered ecosystem in the digital space of outlets and podcasts and streaming and things on Discord and Telegram. Every, every sort of way. We're trying to touch people where they are, which is on their phones, on their screens, in their homes, podcasts, in their cars. And it's starting to work. The growth of substack, the growth of, of the. The guys at Midas have killed it. The guys at the Bulwark have killed it. Lincoln Square's coming up strong. We're loving where things are going with this, but we have to build a new media. The insufficiency of the old media structures is apparent every minute of the day. And I think there's something more honest and direct and real for a lot of voters and a lot of Americans about what we're doing on substack, what we're doing in podcasting, what we're doing in streaming, than just a 30 second hit on a cable TV channel. Man, I used to do so much cable. I used to do so much. There was a period of time, I think it was 2017, where I did 600 television hits in a year. That's two a day, folks. It was insane. You know, used to do a million MSNBC heads. The way you reach people now is here. And the way that political media is now functioning is here. You're hearing and watching people you've built a relationship with. They're not a billion miles away. You know, it was funny. I said, hey, I was in the hardware store and a guy walks up to me. He goes, man, I watched your stream last night on the breakdown. It was so good. I'm like, thank you. I'm in an Ace Hardware in Tallahassee, Florida, and there's a guy talking to me in a red state. And there's a guy talking to me because, you know, he saw something and he's like, yeah, I really. I showed my wife and it, you know, it made me feel better about. I'm like, holy shit. You know that when it comes home to you, like, that it really is meaningful. And is it work? Sure, it's work. But. But, you know, traditional media and journalism, I. I tell you, I love journalism and journalists. Sometimes I. Sometimes I'm journalist adjacent. Sometimes I do journalism, sometimes I do opinion. Mostly I do opinion. It's the only, Only job protected in the Constitution. Mentioned in the Constitution. Free press. And this is the new free press. We don't have a corporate master. We don't have a boss. We don't have a super pac. We don't have debt to some hedge fund. It's just us doing what we do. I love these Q and A's and that. And I'm not kidding you when I tell you the question pool is amazing. We will come to more. I've got another 125 questions from the last couple of days. We're trying to keep up with it. Hey, by the way, you can absolutely do us a big lift, a big favor. Subscribe to Lincoln Square. It is a vastly growing and important outlet. We really believe in it. Follow me on my substack if you'd like. I do a lot of free content. A couple things behind the paywall every week, but mostly free content. Also, check me out on the LinkedIn Project podcast. And every Friday, I do a podcast called the Elephant in the Room, where I try to pull back the curtain on something that's happening in American politics. That's generally during the week where I let it rip. Anyway, thanks, everybody. We'll talk to you again soon.
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Podcast: Rick Wilson's The Enemies List
Host: Rick Wilson (Black Pearl Studios)
Date: June 25, 2025
In this Q&A episode, Rick Wilson tackles urgent listener questions about the state of American democracy, the generational divide in activism, the current challenges faced by the Democratic Party, and the evolution of political media. Running throughout is Wilson’s mission to call out those undermining democracy and to encourage his audience to remain engaged, hopeful, and ready for the fight ahead.
Wilson is candid, direct, and passionate—equal parts alarmed and hopeful. He mixes personal anecdotes with political analysis, using humor and blunt language to connect with the audience and underscore urgency. He is clear-eyed about the threats to democracy but insists on proactive engagement, optimism, and adaptation to cultural and technological shifts.
This episode offers Wilson’s signature real-talk for listeners concerned about democracy, parenting in turbulent times, the health of activism, and the battle for how Americans get their information. His answer to each crisis: stay engaged, support independent media, organize with both energy and wisdom, and—importantly—never cede hope to fear.