Why are we so Cautious? with Jack Schlossberg

Summary

Podcast Summary: The Blueprint with Jen Psaki – "Why are we so Cautious? with Jack Schlossberg"

Release Date: February 10, 2025

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Introduction

In the latest episode of The Blueprint with Jen Psaki, host Jen Psaki engages in a candid and insightful conversation with Jack Schlossberg, a prominent writer and political correspondent. At 32, Jack brings a unique perspective as the son of Caroline Kennedy and the grandson of President John F. Kennedy. Over the course of their discussion, Jack delves into the challenges Democrats face in the current political climate, especially in engaging young voters and combating the effective strategies employed by conservative voices online.

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Social Media Strategy and Experimentation

Jack Schlossberg opens the conversation by highlighting the critical role of social media in modern political discourse. He emphasizes the necessity for Democrats to adopt more bold and sometimes controversial approaches to break through the saturated online environment.

Jack Schlossberg [01:09]: "I don't know that we've come up with our own style of being funny and taking risks. People talk a lot about how we lost Democrats, lost young men this election. I think a huge part of that is like not because we focus on the wrong policies, but because we seem so risk averse and we seem so cautious."

Jack shares his personal experiments with social media, including provocative tweets and satirical claims, such as asserting he is Justin Baldoni's lawyer. These actions are designed to test the spread of misinformation and observe how disinformation travels online.

Jack Schlossberg [07:00]: "I think it's funny that people believe something so stupid or something so easily corroborated... If we're too scared to say something like that, then what happens when something that really matters happens?"

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Election Losses and Messaging Challenges

A significant portion of the discussion centers around the Democrats' performance in the 2024 elections, particularly their inability to resonate with young voters. Jack attributes these losses not to policy failures but to a lack of dynamic and engaging communication strategies.

Jack Schlossberg [13:18]: "The Internet is like a nuanced destruction machine... There's no room for anything ever. Don't waste your time. If you're going to tweet something out, make it so extreme."

He further critiques the Democratic Party's messaging as too restrained and policy-focused, lacking the relatable and diverse content that appeals to a broader audience.

Jack Schlossberg [16:55]: "Young people are like any other people. They need to be given clear arguments and reasons why they should support a candidate or a party."

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Engagement Strategies and Content Flooding

Jen Psaki and Jack explore the importance of flooding social media platforms with varied and engaging content. Jack advocates for a mix of controversial and softer content to capture and retain audience attention.

Jack Schlossberg [30:31]: "I think that it seems like the candidates who have done well on the Democratic side have been able to kind of pick their own brand of being a Democrat... They need to be just making tons and tons of videos."

Jack underscores the necessity of constant experimentation and content creation to stay relevant and competitive against the well-entrenched conservative online presence.

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Trolling, Authenticity, and Balancing Act

The conversation shifts to Jack's approach to trolling and maintaining authenticity online. He explains that his playful and sometimes provocative online persona is a strategic attempt to engage diverse audiences and challenge prevailing narratives.

Jack Schlossberg [36:12]: "If we don't make fun of them and if we don't have our own ideas and we just say that they're bad, then we deserve to lose."

Jen Psaki probes the delicate balance between adhering to political norms and embracing a more authentic and sometimes irreverent online presence. Jack responds by emphasizing the importance of being genuine and adaptable in the evolving digital landscape.

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Media Landscape and Influence

Jack provides a critical analysis of the current media environment, pointing out the overwhelming influence of conservative-leaning social media platforms and their symbiotic relationship with traditional media outlets.

Jack Schlossberg [27:26]: "Social media companies are all working with the Trump administration... This is like the biggest propaganda machine that's ever been invented."

He calls for a coordinated and continuous online campaign from Democrats to counteract the pervasive right-wing propaganda and regain influence over the cultural narrative.

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Future Steps for Democrats

As the episode draws to a close, Jack shares his optimistic view on the potential for Democrats to revamp their communication strategies. He highlights the importance of leveraging diverse media platforms and fostering authentic connections with voters.

Jack Schlossberg [31:03]: "Literally half the battle is just getting stuff out there, try things."

Jen Psaki encourages Democratic candidates to embrace varied and frequent content creation to enhance their visibility and appeal, especially among younger demographics.

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Concluding Thoughts

The Blueprint with Jen Psaki wraps up with a forward-looking discussion on rebuilding the Democratic Party's online presence. Jack expresses hope in the resilience and creativity of Democrats to adapt and thrive in the digitally dominated political arena.

Jack Schlossberg [42:49]: "It's propaganda being used against people, and I'm not gonna sit by and let that happen unanswered."

Jen Psaki commends Jack for his innovative approaches and underscores the necessity for Democrats to stay engaged, authentic, and proactive in their communication efforts moving forward.

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Notable Quotes

1. Jack Schlossberg [01:09]: "I don't know that we've come up with our own style of being funny and taking risks. People talk a lot about how we lost Democrats, lost young men this election. I think a huge part of that is like not because we focus on the wrong policies, but because we seem so risk averse and we seem so cautious."

2. Jack Schlossberg [07:00]: "I think it's funny that people believe something so stupid or something so easily corroborated... If we're too scared to say something like that, then what happens when something that really matters happens?"

3. Jack Schlossberg [13:18]: "The Internet is like a nuanced destruction machine... There's no room for anything ever. Don't waste your time. If you're going to tweet something out, make it so extreme."

4. Jack Schlossberg [27:26]: "Social media companies are all working with the Trump administration... This is like the biggest propaganda machine that's ever been invented."

5. Jack Schlossberg [31:03]: "Literally half the battle is just getting stuff out there, try things."

6. Jack Schlossberg [42:49]: "It's propaganda being used against people, and I'm not gonna sit by and let that happen unanswered."

---

Conclusion

This episode of The Blueprint with Jen Psaki offers a deep dive into the strategic communication challenges facing the Democratic Party. Through Jack Schlossberg's bold experimentation and critical insights, listeners gain a nuanced understanding of the urgent need for more dynamic and authentic engagement strategies to connect with younger voters and counteract the dominant conservative narratives online.

For those interested in the future trajectory of Democratic communication and strategy, this episode provides valuable perspectives and actionable ideas to consider.

Transcript

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[Jack Schlossberg]

It'd be very clear and you have to be very controversial in order to break through, I think, and conservatives are good at playing with that without getting in trouble. And I don't know that we've come up with our own style of being funny and taking risks. And people talk a lot about how we lost Democrats, lost young men this election. And I think a huge part of that is like not because we focus on the wrong policies, but because we seem so risk averse and we seem so cautious.

[Jen Psaki]

That's Jack Schlossberg. He's a writer, he's a political correspondent and yeah, he's also a Kennedy. At 32, the son of Caroline Kennedy and the grandson of JFK, has been doing his own sort of social media experiments to see what sticks, how disinformation travels, and how to break through the wall of conservative voices in every corner of the Internet. Hi there, I'm Jen Psaki, host of MSNBC's Inside with Jen Psaki. And this is the Blueprint with Jen Psaki. I'm here to try to make sense of what went wrong in 2024, what Democrats may have missed and what it means importantly for the fight ahead. For this episode, I wanted to talk with Jack about where Democrats have fallen short with young people and what lessons they should take away from the right wing online machine that helped elect Trump. I caught up with Jack right after the inauguration. Jack, first of all, I'm very happy to see you.

[Jack Schlossberg]

Happy to see you now.

[Jen Psaki]

For anyone listening, this is the morning after the inauguration and while some people, because this will come out a couple weeks later may have had some time to digest. You and I are just digesting what just happened yesterday. So just keep that in mind.

[Jack Schlossberg]

Yes, it's fresh.

[Jen Psaki]

Everybody listening? It's a little fresh for us. I first met you, I think, through my brother in law, Adam Frankel.

[Jack Schlossberg]

Adam Frankel, one of the best ever.

[Jen Psaki]

The best ever. Who not only wrote Kamala Harris speech at the convention, but she helped Ted Sorensen, of course, write an amazing book. And so I met you through him. I was trying to get you on her show. We'll still do that, but since then we've kind of texted just about the Democratic Party, how to communicate, and since the election, a lot about what's wrong and what we should do. Neither of us have all the solutions, but that was one of the reasons I really wanted to talk to you about what you think and where we should go from here.

[Jack Schlossberg]

Well, I'm so happy to be here and I'm such a fan of your career. I have to say that not only your book that just came out, which I read and loved and everybody should read it, but also your time in the White House working for President Biden, especially as press secretary. You did an incredible job and you such a skilled communicator. So it's great for me to be here.

[Jen Psaki]

Just for the record, I didn't ask you to do any of that, even plug my book. I'm appreciative. Thank you for that. But I've loved getting to know you a little bit, so. And I was just excited to talk to you about all of this. Okay. So social media is such a big topic. I would say you've been having some fun on social media. You've been messing with people's heads a little bit on social media. But I think a lot of people may not understand what you're up to a little bit. And I've talked to you a little bit about this, so I kind of. I want to help people better understand. I mean, just yesterday you tweeted, I have to bring this up. You did it yesterday. Tweet. True or false? Usha Vance is way hotter than Jackie O. Who? Everyone shot your grandmother.

[Jack Schlossberg]

Why would I say something like that?

[Jen Psaki]

There's a lot packed into that.

[Jack Schlossberg]

Creepy. Is it weird? Why would he say something like that? Why did he do that?

[Jen Psaki]

Isn't that weird?

[Jack Schlossberg]

It's his grandma. Well, that's why I did it.

[Jen Psaki]

Because you wanted it to be weird.

[Jack Schlossberg]

I think that the Internet is a place where it's difficult to break through and it's difficult to Break through, especially if you're not saying something that's controversial or at least somehow unexpected. And I think that I see that Democrats play that game not as well as we could. And I think that I use my judgment to make posts that I think are funny or silly, but have a purpose, either to make you think this guy's crazy. Why is he talking about his own family that way? But to be honest, then you get all these retweets quotes, and everybody flips out about it. And I think that that's kind of the game that the other side's been playing really well, which is flipping people out and getting a reaction is almost half the battle. And not every post is going to be hilarious or risky in some way. Some of them have to be serious and boring, but they can't all be serious and boring. And so I think that it's very important to switch it up and to take risks, because I think that's not only entertaining for me and myself as I laugh and post it on my phone, but also a good way to signal to people that you're willing to either fight for them or speak your own mind if you're willing to say something that's other people might not get or, you know, might engender a reaction that some people don't like.

[Jen Psaki]

I mean, that one's definitely perplexed people. I was looking at the comments, which is always a dangerous thing to do, and people were like, isn't this your grandmother? Question mark.

[Jack Schlossberg]

Exactly.

[Jen Psaki]

And then people would actually answer the question, which was a strange thing to do. Is this what you're doing? Exactly. There are some things. I mean, you also claimed you were Justin Baldoni's lawyer, which you're not.

[Jack Schlossberg]

No. Yes, I'm not.

[Jen Psaki]

You do have a law degree. I do. That confused people.

[Jack Schlossberg]

Yes.

[Jen Psaki]

But that also took off huge.

[Jack Schlossberg]

Yeah. I don't know. It just kind of came to me one night. I see everybody arguing online about Justin Baldoni and Blake Lively, two people that otherwise I don't know anything about or have much invested in. But I saw the entire country, seemingly the entire Internet, flipping out over this while I was focused on kind of the change of administration and all the serious things that are going on. And I thought, isn't this incredible? Our culture is obsessed with certain things and not others. Some are more important than others, you might say. So how do you inject yourself and shine a light on that in a way that is, like, totally out of the box? And for me, it was like, well, why don't I Defend the guy who nobody likes. And everyone is going to get mad at me. And it's just kind of like an instinct that I started to build up and people believed it. People printed it and believed it.

[Jen Psaki]

Well, that's been checked.

[Jack Schlossberg]

TMZ reported it. A bunch of other people reported. They said I was Justin Baldoli's lawyer. Hilarious.

[Jen Psaki]

Well, that, I think, was part of your point. Exactly.

[Jack Schlossberg]

People will print and believe anything.

[Jen Psaki]

But then the other part of it, which is why most people are unwilling to do what you do, is that it can take off. And then people. You actually. Who you actually care what they think, may think you're Justin Baldoni's lawyer. So there's this risk of that too. Right. Do you just care?

[Jack Schlossberg]

Yeah. No, I don't care. I'm like, I know no one's going to remember this in a week. I know everyone's going to forget about it because they've forgotten about a lot of way more serious things. And I think that at first I was freaked out because everyone was mad. And then once people started to understand it was a joke or that I was kind of. It was satire, I think people started to understand the game I was playing.

[Jen Psaki]

Yeah, you'd hope. But you. The point is.

[Jack Schlossberg]

But I don't care if people don't get it, because I think it's funny.

[Jen Psaki]

So is it about funny or is it about you're showing that disinformation and misinformation travels?

[Jack Schlossberg]

Exactly. I think it's funny. That. Not funny, but I think it's. I can't help but laugh that people believe something so stupid or something so easily corroborated. You could so easily look up and find out that that's not true. But at the same time, it's like if we're too scared to say something like that, then what happens when something that really matters happens? You know, you have to be willing to take risks and speak your mind and live with the consequences and be okay with not everybody understanding you.

[Jen Psaki]

Okay. Those ones, I. I knew immediately you were messing with people. Now, you also put out a video, I think it was in the fall, where you basically claimed that you had. Had your heart broken. Yeah, that's right. I was one of. I don't know how many people. Dozens, Hundreds of people who text you. I think I was like, heartbreaks are hard. You're gonna find the right person. I'm so sorry this happened.

[Jack Schlossberg]

I know. I was so.

[Jen Psaki]

But that wasn't real.

[Jack Schlossberg]

I know. I hate that I got you, Jen, but I'm Okay, I got you. Yeah. No, I mean, like, I couldn't stop laughing when I recorded that video. I thought it was one of the funniest things I've ever done, but. Because I would never. I would never. If I was actually going through a breakup, I don't think I would want anyone to know how sad I was. So this was, like, my way of showing just that people will believe anything and that it's just. It's not a game. Because there are serious consequences to information online. We're seeing that now in this election. But it also is a game in terms of, like, you can speak to multiple different people at the same time, and you can speak to different audiences in different ways. Like, I'm speaking to people who I know will get this joke and think it's hilarious. And I'm also speaking to the people who I know won't get it, and we'll take it as bait. And those two people are gonna interact and they're gonna think it's funny that some people don't get it. And I think that we see that all the time. There's, like, everything from dog whistling on policy to jokes like, I'm making. I think you have the ability to play people based on the reaction you know you're gonna get.

[Jen Psaki]

It's so interesting because you seem to be willing to let yourself be made fun of or let disinformation spread about yourself, but you're also, in some ways, and this is just my take, like, manipulating the Internet a little bit.

[Jack Schlossberg]

Yes, I. I love my country. I love politics. I really care what happens. And I've been like, everybody, like you, paying attention to what's happening in our country and in our politics and in our media. And I'm developing instincts, as we all are, as this changes and we get more used to misinformation. And I think it's something that I think deeply about. And so there's also serious points I'm trying to make doing all this. And I think that I've watched the other side, people say that. Like, you're saying crazy stuff. People aren't going to take you seriously. Why would you air out your stuff in broad daylight for? I'm like, are you not looking at what's going on on the other side? Like, apparently nobody cares. And that's kind of the point that I'm trying to make. It's like, yeah, you can make fun of me. I don't think that you're actually going to remember it in a week, because something else is going to take your attention and you're going to forget and then I'm going to do something else and then you'll focus on that. And we're all kind of now evolving to understand that that's how the media works and maybe we need different strategies to break through.

[Jen Psaki]

No, I think this is very true. I mean, I've been listening to a number of podcasts, as we like to say, from the other side, which I probably never would have before the election. I mean, I've listened to some of Joe Rogan, I've listened to Theo Vaughn. I have not gone down the Steve Bannon rabbit hole because I. Yeah, but I may get there. But point is, the conversations are very different. That's just a sliver of this. And one of the things that struck me is that they're more how people talk, even though I completely disagree with most of what a lot of those people have to say. But they're not afraid to talk about everything from music to football to art to whatever they're into, right?

[Jack Schlossberg]

Totally.

[Jen Psaki]

And sometimes I think Democrats, in how they communicate, and you and I have talked about this, are so restrained. It's like they only want to talk about a fact sheet that was developed by a Harvard educated policy expert.

[Jack Schlossberg]

Yep. No, I mean, I think we have a real. Democrats have a real problem messaging online. I spent the first half of the year in 2024 being really frustrated by what I wasn't seeing online. And then I spent the second half making my own content because I decided that the only way to combat misinformation that I can come up with is to put out your own information and to make it more entertaining or at least have it be competitive with what the other side or people you disagree with are putting out. And as you just said, the kind of conservative leaning voices, especially on social media, are so much more compelling to watch for the most part, or at least they're touching on things from sports, music, like you just said, dating, whatever it is, it's all of it, and politics. And they've kind of. I mean, I've seen like our culture has been seeded to kind of the right. And whereas it may be my whole life growing up, culture, institutions were more left leaning. And now I think that's really flipped on its head and I think the Internet is like the battleground for that. And I think conservatives are now in the driver's seat and in the majority of culture. And they've kind of convinced. I have to wake up every day now after the election to convince myself that I'm not a loser. And convince myself that caring doesn't make you not cool and that I wasn't wrong about everything that I thought. And it's because I see online you watch one video about working out and then you're in a rabbit hole of RFK Jr protein powder, Joe Rogan. None of which is like in and of itself objectively bad. But altogether I think it drowns out competing voices and it's very hard to break through. And so that's what I tried to do myself.

[Jen Psaki]

The experimentation of it, I think is important because no one exactly has the answer, which is why I want to do this podcast, why I want to talk to you. What have you found either from your own experimentation with playing around with social media platforms or even just from listening to and consuming the products of some of the people you may totally disagree with works.

[Jack Schlossberg]

Yeah, I mean, I, I have like a, a few thoughts. I think one is the Internet is like a nuanced destruction machine and so there's no room for anything ever. Don't waste your time. If you're going to tweet something out, make it so extreme. Like that's what Trump does. It's like a completely clear statement, take it all the way. And that's the only thing that really resonates online because everything else, it's too confusing otherwise. And the other thing is you have to be controversial or unexpected, so you have to be very clear and you have to be very controversial in order to break through, I think. And conservatives are good at playing with that without getting in trouble. And I don't know that we've come up with our own style of being funny and taking risks. And people talk a lot about how we lost Democrats, lost young men in this election. And I think a huge part of that is like, not because we focus on the wrong policies, but because we seem so risk averse and we seem so cautious. And I don't think that in general young men find that as attractive as a more risk on kind of say whatever you want attitude.

[Jen Psaki]

You said this thing and I wrote this down because it just stuck with me as I think it's important for people to hear on the Vogue podcast. I think it was the morning after, soon after the election. Everything was quite raw as we've been talking about. You said, I think that a lot of people my age maybe aren't really proud to be a Democrat. And I think that this election is very interestingly showing that Democrats have some work to do there, which is, I'm a Believer you just lost. So let's everybody talk about what just happened and where you go from here. Do you think it's about how people communicate? Is it about policy issues? Is it about both? Is it about not connecting? Like, what is it when you talk to your friends, what do they say?

[Jack Schlossberg]

Well, for my own life, I grew up with stories of people that I was related to who were Democrats, who gave their lives to public service. And I had these real examples of, no, no, no, like the Democratic Party cares. They care about working people. They championed health care, they championed immigration, civil rights, kind of all the issues that I consider the defining issues. But I only know that because there's pictures of these people in my house and because my mom talks about them and because I would happen to be interested in it on my own. But I think when you talk to somebody my age or younger, they don't have all the context and like they grew up in a world with like only a few examples, like Bill Clinton. We were still really young. So you've got George Bush, Obama and Trump and Biden more recently. And it's like that doesn't give you a whole lot to go with in terms of what Democrats actually stand for. It's like, it's really confusing now. It's very confusing. You're being fed a whole narrative about how Democrats hate everything and all we care about is like gender and things that which we do and is important. But wasn't always the defining issue of the Democratic Party was not reproductive rights. And I mean, that was this campaign. Before that it was like working people, working families, labor unions, and that's now all on the other side. And so I think young people are like any other people. They need to be given clear arguments and reasons why they should support a candidate or a party. And I haven't heard a super compelling clear argument from any Democrat about something that really resonates with young people beyond kind of democracy and civil rights.

[Jen Psaki]

Broadly, does that stuff feel? I mean, I've wondered this, but like I, you know, after the election I kind of felt like obviously the threat of fascism is an issue. Right? Obviously the threat of rising autocracy is an issue. To me, it always felt very academic and that a lot of people, including me and others, were talking about things in a way that was how you talk about things in a college classroom and not how people are taught talking about things. And I'm not even necessarily speaking of how people at their kitchen tables talk about things in Missouri. I mean, you are in a Harvard educated guy who is a Kennedy. It's not exactly like you grew up with nothing. But you also, I think, share this concern about language.

[Jack Schlossberg]

Totally. Yeah. I mean, I think that I would be very, very disappointed if the Democratic Party took the lesson from this election that we went too far left and that our policies were too extreme. I would say that they were just way too vague and not far enough. And that we kind of got scared of our own shadow in a lot of ways. And we were. Or at least, like, I find it hard to not kind of believe the narrative that's being fed to me about my party from the other side. It's like, it's convincing when you hear it every day.

[Jen Psaki]

And what do you think the narrative is from the other side?

[Jack Schlossberg]

That we, like, are losers, we do not care about the economy, and that we, like, actually want to make things more difficult in order to help a perceived group that nobody knows who they are. Like, we're so incompetent because we care so much about the wrong thing. Like, I just think that we're incompetent is, like, the message and that we, like, just don't get it. We don't get anything. We don't get how it really works.

[Jen Psaki]

Do you think that I'm just gonna restate. Like, you and I both believe that Democratic Party and Democratic values are hugely important, and this is trying to get to the root of why nobody's hearing that. Do you think that part of it is. And you worked for the campaign, but that Joe Biden is older and people didn't feel he connected? But then Kamala Harris was the candidate. Was it more than the candidate? It was a bigger issue than that.

[Jack Schlossberg]

Well, I mean, I was definitely. I don't have an answer. And I was frustrated by this in real time. I mean, I consider Joe Biden to be the most successful president of my lifetime, whose legislative. I mean, you were there, and you. You know how much he got done from climate, infrastructure. The list goes on. I don't think people got that, because I still just think that we're too scared. We're too scared to say what we really want. And we saw it toward the end. Like, toward the end, we started saying, like, ban assault weapons. Toward the end, we started, like, the last day, the Equal Rights Amendment. Like, we got a little bit scared, I think, of doing those things for fear of not playing to the middle. And we didn't win the middle anyway, so it didn't work.

[Jen Psaki]

We're going to take a very quick break here, but when we come back, More with Jack Slosberg and the backstory to another one of his viral moments.

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[Jen Psaki]

So you kind of have this very interesting vantage point for a range of reasons. One is you did some campaigning with people candidates, including Josh Shapiro. I'm just gonna go on the record that I find mayonnaise to be the most disgusting thing that exists on the planet. Like, I literally feel faint saying the word out loud and I can't have it in my fridge. You are a mayonnaise lover.

[Jack Schlossberg]

Or was that just a prank?

[Jen Psaki]

Well, I don't know.

[Jack Schlossberg]

I was just like, do you actually like mayonnaise?

[Jen Psaki]

If you actually hate mayonnaise, you would never talk about putting it on pizza. Let me just say that I love it. How did you. But this is kind of funny. I mean, I refreshed my memory about it before we talked, but I remembered the video.

[Jack Schlossberg]

A lot of people think this is weird, but it is true. Mayonnaise is my favorite food. I absolutely love it. I'll put it on anything. I wish I had some right now. You would not put that on your 100. The whole thing will be covered.

[Jen Psaki]

Dude, that's gross.

[Jack Schlossberg]

I know.

[Jen Psaki]

Well, how did you come up with that? Did you talk to the Shapiro team? There was a reception.

[Jack Schlossberg]

Very like, my whole experience over the campaign was like, very much kind of how that came together. It was like everything was happening all at once. There was no plan. And like, that came out of my mouth. And then they did a really good job editing it. His team and put it up front and picked it up. That was a really good moment. And then everyone knew that I loved mayonnaise. But I would say that it just.

[Jen Psaki]

Shows you that all the ladies listening, right? Just decide if that's on your.

[Jack Schlossberg]

But it just shows you that the things that you plan oftentimes with communicating the things you plan the least, the things that you're not really thinking about, the things that aren't about, like, policy. It's just like, I love mayonnaise. Like, that's what people connect to. And for some reason that's like, familiar. People say, oh, I hate it or I love it or whatever. And then that's how the Internet works. It's like, oh, like. But meanwhile, I've injected into their minds that Democrats aren't lame because, like, they're watching my video and we're eating pizza and we're having fun. But it's not about that. It's about, like, mayonnaise. Is it good or bad? And everyone has a take.

[Jen Psaki]

That video and some of the stuff you did made me think about when I was working for Obama and I worked for him for 10 years. He was a person who could kind of pull off things online. Everybody can't, which is true. You don't have to name names, although you can. I know some people can't. But it works for some people and doesn't work for others. So you have to kind of find the authentic thing, which can be hard. And we always thought about it as we want people to look at this video or this photo or this event or whatever it is who aren't clicking refresh on whitehouse.gov the audience beyond that. Right. How do you think about that question and how when talked to these campaigns or were working with them, how did they think about it?

[Jack Schlossberg]

This was like the most interesting part of this campaign cycle. And something that makes me very optimistic and hopeful was. Was how recept. Like I remember when, like going on Meet the Press, like you were saying before the interview, like having an op ed, that was all you needed. Now, I know we were saying just.

[Jen Psaki]

To repeat because I think it's where. And you and I agree on this. There's still. And I'VE lived in Washington on and off for over 20 years. Still a stunning percentage of people. And you know this because you've talked to a lot of these elected officials, too, who think that if they have a written op ed in the Washington Post, and I'm not just trying to pick on the Washington Post because Jeff Bezos is a tech bro who's part of the oligarchy, that's a part of it, but that if they do that and they do a press conference on the steps of the Capitol or the Cannon House Office Building, that the world will hear them and they will not.

[Jack Schlossberg]

Not quite. Yeah. No, I mean, I think this was the first time. I mean, I would. I can imagine if you asked a politician five years ago, will you sit down with an influencer and make a video, let them interview you for five minutes, whatever they want. They'd be like, are you kidding? And then I show up at the DNC and it's like, every candidate wants to have videos made with influencers, no matter if they have a million followers or 10,000. And I thought that. I was like, that really opened my mind and I thought that was a really good thing for us to try to get our message out there. But, yeah, as you said, it's like, you can't be fake. It's all about, like, being comfortable and not being scared to be. Like, I was so encouraged by that people liked my videos because I think that I'm like, a goofy, silly person and not everybody gets it.

[Jen Psaki]

Oh, you're quirky in the best way.

[Jack Schlossberg]

Yeah. But, like, people get it. And it's like, so surprising and encouraging that people are receptive to that. Whereas you would think, like, at first, everyone said it was a terrible idea what I was doing. Everyone said I was an idiot and crazy. And I was like, I think people will get it. So I think it's like, it shows trust in other people when you're willing to expose different types of your personality and you let people see that and you trust them to interpret you for who you are and not be like, oh, he said that I'll never listen to him again. And like, no, that's not really how people work.

[Jen Psaki]

In a weird way, I've thought about how the Trump era has kind of destroyed many things, but I'll just focus on what is presidential and what is presidential aspiring or not. And there kind of aren't rules anymore. And that's a scary thing. And I'm not even gonna go down the rabbit hole of his control over many platforms, but I do think it has made it so that people expect an accessibility and a realness and an authenticity about people they may vote for or support or get excited about in the media, but also elected officials and people running for office in a way that wasn't the case 10 years ago. Like, it's totally shifted.

[Jack Schlossberg]

Totally. I feel like, I mean, we seeded the whole Internet to the right and we didn't make anything good on there. And of course we lost is how I see it. And like, what did you think was gonna happen if no one was making any videos that anybody was watching and we were just getting worked on TikTok and Instagram every single day? And I don't know where it's going to progress, but I think that it's a good thing that it's like, if Cancel culture is dead and woke means you lose, then we should embrace that and say, okay, great, let's use those tactics to our own advantage and be entertaining and not worry so much about people misunderstanding us. And I think that's kind of what I try to do online is like, I'm not going to worry so much about someone thinking that I'm not acting the way I should. Like, I'm going to trust that people will get it and. And that's okay. And also, by the way, just one thing. You said you didn't want to get into the tech, bro.

[Jen Psaki]

Oh, go ahead. We can.

[Jack Schlossberg]

I think that this is the most important thing in the entire world. I think that social media companies are all working with the Trump administration. Elon Musk owns X. They own all of the data and all of basically all of the media in our country. And they're all in bed with the current administration. And we can't rely now on, on the pendulum swinging back and forth. It's like they're going to produce a TV show every single day online that says that they're winning and says a different version of reality. And we can no longer expect people to understand what's going on and, and react to the outcomes of policy when it's completely divorced. And this is like the biggest propaganda machine that's ever been invented. And if we don't get our stuff together and have a coordinated. We need a full time campaign online like we had during Kamala's campaign 24 7. It's like, that can't end after the election. They're going. And so, I mean, I'm like, there's no way we win. There's no way we claw back power unless we do something about that or get competitive on there.

[Jen Psaki]

I think this is also the most important issue. And I more was like, let me ask you this question first because, because I think for anyone who doesn't understand this, I mean, Elon Musk has completely taken over Twitter, or X, whatever we're calling it these days. It is an absolute dumpster fire of right wing propaganda insanity. You're still on there. I'm still on in part because I have 1.3 million followers and I'm like, I don't wanna give that up. But then I'm like, what's the point anymore? But then you also have Mark Zuckerberg, who apparently went through some sort of strange image consulting that resulted in what we're seeing these days, but he controls other major platforms. Then you have TikTok, which now if Trump tries to save it, maybe one of his buddies is gonna buy it. Those platforms together. How the majority of people in this country are consuming news.

[Jack Schlossberg]

Yep. And it's like they're driving, you know this, they're driving traditional media as well. Like, traditional media is now like running off of what social media is trending. So it's like, this is like out of control, in my opinion. And it's, it's not going to. People are not going to like, see Trump again and realize that they don't like him like they did before. If they did, it's like, no, no, this is completely different now. Everyone is convinced that Democrats are actually completely incompetent and only care about, like purposefully ending the world. And we don't have an answer and we're not funny and we're not entertaining. I mean, don't get me wrong, there are amazing politicians out there who are doing a great job. And I'm inspired by a lot of them. Inspired by Chris Murphy, I'm inspired by Gretchen Whitmer, Governor Shapiro, Governor Newsom. The list goes on, but it's not coordinated and it's not centralized like the other side has.

[Jen Psaki]

I've thought a lot about. I root for all of the people who may run for president one day. May it be many. There are lots of good people, as I'm sure you do too. But because I worked in communications for 20 years, I'm like, I have so many thoughts for each of them and their advice. You've probably thought about what you wish a lot of these people would be doing as we look to the next two years. I mean, if Democrats can win back the House, Trump will never get another piece of legislation passed. House candidates, people who are running for how they don't have as much money as people are in the sunny. They don't have as much money for people running for president. They can use these platforms. What should they be doing?

[Jack Schlossberg]

Well, I don't know. First of all, I don't know.

[Jen Psaki]

Everyone's different.

[Jack Schlossberg]

But I think that it seems like the candidates who have done well on the Democratic side have been able to kind of like pick their own brand of being a Democrat based on where they're at and not having to sign up to every or they're allowed to distance themselves. In some ways, I think that's going to be critical for people to be able to actually tailor what they're doing to where they're at and to hear from constituents. But basically, I really think that they need to be just making tons and tons of videos. If they don't do that, they're not going to win.

[Jen Psaki]

Lots of content just, you need to flood the zone.

[Jack Schlossberg]

It's like literally half the battle is just getting stuff out there, try things.

[Jen Psaki]

It's so interesting. One of the things we've learned, and I'm sure you've had someone ask you this too, I was like, I want to engage on all these platforms. I'm a believer and this comes from my background. You just have to try all of the things you shouldn't be so locked up about, what things you'll try and what platforms you'll try. And so when I started engaging on TikTok and Instagram Reels, I started just doing videos where I would just put my phone up on my desk.

[Jack Schlossberg]

Yeah, no, you do a really good job.

[Jen Psaki]

Well, thank you for that. But like, where I would just say, like, this, this crazy thing happening in D.C. people do all sorts of things behind the scenes, makeup, chart, whatever, that's all fine. Different things work for different people those are more engaged with than any video we do from the show. And it's so interesting because it's just kind of a stream of consciousness thought. But what have you found? Are there things that you thought were gonna be people would find interesting and engaging that didn't work? And things you've done that have worked?

[Jack Schlossberg]

Yes, I would say I had a. A hypothesis that attacking would be the best way to get.

[Jen Psaki]

Attacking, attack, trolling and attacking other people.

[Jack Schlossberg]

Which I still think is like, you have to. I think we need to be attacking way harder all day long. But that has to also be paired with a softer side. Hence my breakup video, for example. Oh, he's softer, romantic, you know, you have to.

[Jen Psaki]

Did you get asked out on the people like ask. I don't read your platforms.

[Jack Schlossberg]

I don't read that stuff. But I'm. I'm sure.

[Jen Psaki]

Maybe.

[Jack Schlossberg]

Maybe. Okay.

[Jen Psaki]

That's not the way to get to you if you're interested.

[Jack Schlossberg]

It's the short answer.

[Jen Psaki]

You don't read it. Okay.

[Jack Schlossberg]

But, I mean, there's some things I know that are gonna be controversial. If I talk about one of my family members, if I say something about being Justin Baldoni's lawyer, maybe. But there are things like pictures of me doing ballet. That's like, I think my most liked post.

[Jen Psaki]

So you've done a lot of those and which you. How long have you been doing ballet?

[Jack Schlossberg]

Like, for about, like a year and a half.

[Jen Psaki]

Only a year and a half?

[Jack Schlossberg]

Yeah.

[Jen Psaki]

My impression was it was something you did as a kid and you just, like, engaged in it.

[Jack Schlossberg]

I wish.

[Jen Psaki]

You clearly love it. But it also feels to me. But tell me if I'm wrong, because you've also talked about toxic masculinity, that you're kind of making a point. Are you making a point with doing ballet?

[Jack Schlossberg]

Of course. Everyone thinks ballet is, like, for girls or something, and it's not. Dancers are the most athletic people in the world.

[Jen Psaki]

Yeah.

[Jack Schlossberg]

They're like many heroes. Cultural heroes, cultural icons are ballet dancers. There's so many amazing male ballet dancers. There's so many amazing female ballet dancers. I think it's an ancient tradition. It's the most beautiful thing. Hardest sport. I think that there is. And I think there's something very manly about it that people don't recognize as manly.

[Jen Psaki]

Maybe.

[Jack Schlossberg]

But I also think that, like, it just plays against the trope that you're seeing of, like, manly meaning, like, Jack, dude, who's like this when it's like, not necessarily. Also, like, I bet you can't even dance well if you're that jacked. Like, you can't move around that good. So that's what I'm saying.

[Jen Psaki]

It struck me because. And as I said earlier, I mean, I've listened to a lot of his. And we've just acknowledged basically that some outlets, like Joe Rogan and others on the right, do things better than Democrats, but they are part of the pushing of toxic masculinity as well.

[Jack Schlossberg]

I mean, like, I think we gotta get over masculinity in general. And I think, like, the one way to attract men, like, the worst way to appeal to a young man is to try. Like, if there's one thing that young men don't respect is people who try. And I feel like if we just.

[Jen Psaki]

Like, don't be too thirsty. Yeah candidates out there.

[Jack Schlossberg]

I'm not going to go, like work out with you just to make you think I'm a guy. I think you're going to have to take my word for it. And I'm going to have to show you my personality and show you that we can relate on another level because I don't know anything about UFC or college football. That's just not my thing. So if we have to play that game, I'm going to lose and I'm going to look fake.

[Jen Psaki]

Next up, I'll talk with Jack about why he's become J.D. vance's top troll. Foreign.

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[MSNBC]

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[Jen Psaki]

I do think it's worth being very clear eyed, very realistic about what's going on here.

[MSNBC]

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[Jen Psaki]

Let me ask you about the trolling because there's this interesting balance that I think is tricky. I think a lot of people are struggling with, including myself, of the balance between seeming reasonable and returning to norms. Right. You know Joe Biden and Jill Biden hosted the Trumps for a tea. What in the hell kind of t that was? I have no idea. One day we'll learn. They rode in the car as presidents have for generations. I support that in general, but there is this weird feeling of how do we support norms and not be dishonest about what we're seeing? How have you thought about that.

[Jack Schlossberg]

I mean, I just kind of can't believe that we keep falling for the same. I mean, I thought when Jill Biden, first lady, went. Former first lady, went to the Notre Dame Cathedral, and then Trump had released all those pictures of like, Trump cologne with her staring at him. And I was like, are we really gonna, like, keep on playing this game and acting like, like he acts very polite in private and then they go and they use it in the most brutal possible way that they can. So, like, why can't we also prepare for that too and be like, sure we'll show up and be nice and also try to manipulate this to get what we need? Because that's what they're gonna do to us every single time. And if we don't do it back, we deserve to lose. If we don't make fun of them and if we don't have our own ideas and we just say that they're bad, then we deserve to lose. Because that's not convincing in the trolling category.

[Jen Psaki]

I mean, you've done hegseth. You've done some things about all sorts of my favorite people. Hegseth, JD Vance. JD, your uncle, RFK Jr. Cousin.

[Jack Schlossberg]

My cousin.

[Jen Psaki]

Your cousin. Sorry, your cousin. I don't have the family tree in front of me. Your cousin. Who's your favorite to troll?

[Jack Schlossberg]

The hey, JD Videos did pretty good. Jd. Jd, I'm at the Senate. I'm at the steps of the Capitol. JD.

[MSNBC]

JD.

[Jack Schlossberg]

But you don't think that Trump lost the 2020 election? JD, I miss you. Hi, JD, it's me, Jack. I'm @ Kamala HQ and I miss you. And I was just thinking about you and wondering why you refused to accept the results of the 2020 election. What do I do, JD? JD, will you be my dad? Those did pretty good online. I think that my cousin, RFK Jr. Is a menace and is a. Is a threat to our public health system. I really hope that the Senate doesn't confirm him as the head of hhs. I think that he's shown utter contempt for doctors in the medical community and for all the problems of American healthcare system. I think we're still the envy of the world and doctors work incredibly hard. I have a doctor who's my brother in law, the guy who works harder than anybody I know. I don't see doctors going around trying to hurt people, and I don't see the medical community going around and trying to make people's lives worse. And that's what he preaches. And I think that that's incredibly dangerous. And that his anti vax policies will. Will have bad results for human health.

[Jen Psaki]

I see it a day. Bear carcasses, head in his car. And that's the weirdest story I've ever heard in my life.

[Jack Schlossberg]

You know, my sister broke that story.

[Jen Psaki]

I know.

[Jack Schlossberg]

Amazing.

[Jen Psaki]

It's like, how is that. What does she think of the whole thing?

[Jack Schlossberg]

She was just like, so. Yeah, I don't know. You'd have to ask her.

[Jen Psaki]

But that is just a completely crazy thing. You also spend some time. So you did some campaigning. You also spent some time as a Vogue correspondent.

[Jack Schlossberg]

Yes, I did.

[Jen Psaki]

And the state of the media right now is a part of the problem as well. I think it's fair to state there's like, fear of lawsuits, there's fear of Trump getting mad. There is sometimes an obedience in advance that we're seeing a little bit out there. What did you learn from being a Vogue correspondent? You were authentically who you are. I mean, people knew what you believed. And what do you think about the state of the media right now?

[Jack Schlossberg]

Well, I learned a lot from working with Vogue. I think that I was so lucky to be able to do that. I had great partners there. I think that I learned that there's so much strategy behind making a video good and like, it. It really matters. Like, there's a lot of work goes into making a video do well, especially if there's some real information that you're trying to get through. So I, I have a lot of appreciation for people who do that because it's not easy. And your second half was, like, about defamation. I think this is one of the scariest things that's happening right now. The Baldoni prank was also kind of a commentary on that as well. He's suing the New York Times for $250 million for defamation. And we're now seeing that this is like a much defamation laws changing in real time. ABC settled their suit with Trump. A lot of people are caving, and it's gonna send a chill to publishers, I can only imagine. So I don't know what to say about that, but I think that you gotta just not play scared. It's like, what are we gonna. How could this go worse? I don't think it could get worse than this. We just got totally booted out of power, and Trump has, like, a massive mandate to make policy and do whatever he wants. I mean, that's what the American people voted for. And, like, so what are we holding back for?

[Jen Psaki]

It's a good question. You have kind Of. I don't know if it's a pressure. Maybe you don't feel a pressure. I mean, because of who you are, because you're JFK's grandson, because you have this big social media platform. I mean, I think there are people who have said, I'm now going to, like, family tree. Like, your uncle, like, started this amazing magazine. Like, can you. Should you do that? Do you ignore all that or kind of, where do you want, as you look to the next two years or four years or whatever it is, to have your voice heard? Is it on these social media platforms or something else?

[Jack Schlossberg]

Well, I think that I have an instinct for social media that I'm growing more and more confident in, and I really enjoy playing that game. And I think that that's where people are needed right now is actually on. So it's, like, hilarious to say that, like, serving my country would mean posting online, but I really do now think that I really see a massive hole and I do not see anything getting better until that's filled. I mean, it's like, this is very basic, but it's like it's propaganda being used against people, and I'm not gonna sit by and let that happen unanswered. That said, there's a lot of ways to serve. I went to law school. I love politics. I wish I didn't love politics, but I do. It's like, I can't help it. It's to me, the most interesting, fascinating thing. I can't ever stop talking about it. I can't sleep a lot of nights just because I'm thinking about it. Whenever I go home, my parents and my sisters just, like, beg me to stop, to just stop talking. So for better or worse, I love it. And I don't. That's never gonna change. And so I think I plan to stay very engaged and adapt with the times. In terms of what that looks like.

[Jen Psaki]

It seems like it could be a million things.

[Jack Schlossberg]

Yeah.

[Jen Psaki]

Are you going to be out there campaigning with people, running in tough races over the next two years? Do you think you'll be that?

[Jack Schlossberg]

I'm going to be making content and I'm going to be doing that both on my Instagram and stuff, and then hopefully in another outlet.

[Jen Psaki]

Oh, intriguing. When are we going to learn more about that?

[Jack Schlossberg]

Not today. But not because I'm hiding anything, just because I'm still getting it together.

[Jen Psaki]

No, it's all. It's all good. That's interesting. So in another outlet. That's great. I feel like this period of time is really Dark. And we've talked about a lot of dark freaking things. So let me just end on kind of a more uplifting note. We were talking before we were being recorded. Recording. What about Senator Chris Murphy and how he kind of gets it on the threat of the social media platforms? I know. He's interesting, too. He's interesting to me, too. Who excites you out there? Are there people who could run, who maybe no one's heard of or who are already prominent figures who you think that's an interesting, exciting person? I hope they do something more.

[Jack Schlossberg]

Yeah, there are a lot of people. Senator Murphy is one, and I've been very impressed and motivated by the rhetoric that he's been using since the election. He's been very, very clear and he's focusing on what I think is the issue that we should be focusing on, which is corruption and the growing influence of billionaires on the administration. I think that, like, that is what we need to be hitting every single day. And he's doing that in no uncertain terms. And he's not qualifying his message. But yeah, I mean, the Democratic. The irony is our bench is so deep and there's so many great people with great media presences. Josh Shapiro, Gavin Newsom, Governor Whitmer, I mentioned I don't know about their presidential prospects. Like, I don't. That's like, I can't let myself do that because I have to stay focused. But I just hope that they keep making videos. I just want more people to make more videos online that aren't from the voices that are already out there who are supporting this president who I don't support. I just think that, like, it could not be more important. Everyone is on their phone all day long and every day people are being brainwashed.

[Jen Psaki]

That is true. It's important to remember. Jack, I love your quirkiness and weirdness and authenticity.

[Jack Schlossberg]

Thank you.

[Jen Psaki]

And I love hearing what you have to thank. So thank you for taking this.

[Jack Schlossberg]

Thanks for having me. This is awesome. Thank you, Jen.

[Jen Psaki]

Thank you. Thanks for listening to the Blueprint with Jen Psaki. We'll be back next Monday with a new episode. Be sure to subscribe to MSNBC Premium on Apple Podcasts to get this and other MSNBC podcasts ad free as a subscriber. You'll also get exclusive bonus content. The senior producer for the Blueprint is Margaret Menefee, and our producer is Vicki Virgolina. John Ball is our associate producer. Our booking producer is Michelle Hoffner, and we had additional support from McKenna Roberts. Our crew this week was Ben Parsons and Charlie Macaron. Our Our audio engineers are Bob Mallory and Katie Lau and Brayson Barnes is the head of Audio production, Alex Lupica is the Executive producer of Inside With Jen Psaki and Aisha Turner is the Executive Producer of MSNBC Audio. I'm your host Jen Psaki. Search for the Blueprint wherever you get your podcasts and follow the series.

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