Transcript of Why are we so Cautious? with Jack Schlossberg

Is your business or farm having difficulty getting a loan or restructuring bank debt?

The good news is there's something you can do about it.

For over 10 years, CreditReview has helped Irish SMEs by appealing unfavorable credit decisions.

For more information, visit creditreview.

Ie.

Creditreview is an initiative of the Government of Ireland. Subscribe to MSNBC Premium on Apple Podcasts. New episodes of all your favorite MSNBC shows now ad free. Plus, Ad-free listening to all of Rachel Maddow's original series, Ultra, Bagman, and Deja News. And all MSNBC original podcasts are available ad-free and with bonus content, including Why Is This Happening, Velshi Band Book Club, and more. Subscribe to MSNBC Premium on Apple Podcasts.

If you very clear and it'll be very controversial in order to break through, I think. Conservatives are good at playing with that without getting in trouble. 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 in this election. I think a huge part of that is not because we focus on the wrong policies, but because we seem so risk averse and we seem so cautious.

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 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 Jenn Saki, host of MSNBC's Inside with Jenn Saki, and this is the Blueprint with Jenn Saki. 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.

Happy to see you.

Now, for anyone listening, this is the morning after the inauguration. While some people, because this will come out a couple of weeks later, may have had some time to digest, you and I are just digesting what just happened yesterday. Just keep that in mind. Yes, it's fresh. Everybody listening is a little fresh for us. I first met you, I think through my brother-in-law, Adam Frankl.

Adam Frankl, one of the best ever.

The best ever who not only wrote Kamala Harris's speech at the convention, but she helped Ted Sorenson- Of course. Write an amazing book. I met you through him. I was trying to get you on our show. We'll still do that. But since then, we've texted just about the Democratic Party, how to communicate. Since the election, a lot about what's wrong and what we should do. Now, there's 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.

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 were such a skilled communicator, so it's great for me to be here.

Thank you. Just for the record, I didn't ask you to do any of that. No, it's true though. Even plug my book. I'm appreciative. Thank you for that. But I've loved getting to know you a little bit, and I was just excited to talk 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. That's right. 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. I've talked to you a little about this, so I want to help people better understand. I mean, just yesterday, you tweeted. I have to bring this up. You did it yesterday. Please. It's all public. You tweaked, true or false, Usha Vance is way hotter than Jackie O, who everyone should know is your grandmother. That's right. Everyone should know. It's your grandmother. Why would I say something like that? There's a lot packed into that. Creopy.

Is it creepy? Why would he say something like, Why did he do that? Isn't that weird? It's his grandma. Well, that's why I did it.

Because you wanted it to be weird.

I think that the internet is a place where it's difficult to break through. It's difficult to breakthrough, especially if you're not saying something that's controversial or at least somehow unexpected. I think that I see that Democrats play that game not as well as we could. 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. I think that that's the game that the other side has been playing really well, which is flipping people out and getting a reaction is almost half the battle. 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. 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 other people might not get or you know might engender a reaction that some people don't like.

I mean, that one's definitely perplexed people. I was looking at the comments, which is always a dangerous thing to do. People were like, Isn't this your grandmother? Exactly. Then people would actually answer the question. Thank you. Which was also a strange thing to do. Is this what we're doing? There are some things. I mean, you also claimed you were Justin Baldon's lawyer, which you're not. No, yes, I'm not. You do have a law degree. I do. I think that confused Yes. But that also took off a little bit.

Took off. Huge. Yeah, I don't know. It just came to me one night. I see everybody arguing online about Justin Baldon 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 the change of administration and all the serious things that are going on. I thought, Isn't this incredible? Our culture is obsessed with certain things and not others. Some are more important others, you might say. How do you inject yourself and shine a light on that in a way that is totally out of the box? 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? It's just an instinct that I started to build up. People believed it. People printed it and believed it. Well, that's the thing. They didn't check. Tmz reported it. A bunch of other people reported they said I was Justin Baldele's lawyer. Hilarious.

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

People will print and believe anything.

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. Then people who you actually care what they think may think you're Justin Beldoni's lawyer. There's this risk of that, too, right? Do you just not care?

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. I think that at first I was freaked out because everyone was mad. Then once people started to understand it was a joke or that it was satire, I think people started to understand the game I was playing.

Yeah, you'd hope. But the point is- But I don't care if people don't get it because I think it's funny. Is it about funny or is it about you're showing that disinformation and misinformation travels?

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 What matters happens. 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.

Okay. Those ones 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 your heart broken. Yeah, that's right. I was one of, I don't know how many people, dozens, hundreds of people who texted you. I think I was like, Heartbreak are hard. You're going to find I'm not the right person. I'm so sorry this happened. I know.

But that wasn't real. I know. I hate that I got you, Jen, but I got you. Well, no, I'm okay. I learned from it. I got you. Yeah, no. I couldn't stop laughing when I recorded that video. I thought it was one of the funniest things I've ever done because 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. This was my way of showing just that people believe anything and that... It's not a game because there are serious consequences to information We're seeing that now in this election, but it also is a game in terms of you can speak to multiple different people at the same time, and you can speak to different audiences in different ways. I'm speaking to people who I know will get this joke and think it's hilarious. I'm also speaking to the people who I know won't get it and will take it as bait. Those two people are going to interact, and they're going to think it's funny that some people don't get it. I think that we see that all the time. There's everything from dog whistling on policy to jokes like I'm making.

I think you have the ability to to play people based on the reaction you know you're going to get.

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

Yes. I love my country. I love politics. I really care what happens. I've been, like everybody, like you, paying attention to what's happening in our country and in our politics and in our media. I'm developing instincts as we all are as this changes and we get more used to misinformation. I think it's something that I think deeply about. There's also serious points I'm trying to make doing all this. I think that I've watched the other side. People say that you're saying crazy stuff people aren't going to take you seriously. Why would you air out your stuff in broad daylight? I'm like, Are you not looking at what's going on on the other side? Apparently, nobody cares. That's 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. Then I'm going to do something else, and then you'll focus on that. We're all now evolving to understand that that's how the media works, and maybe we need different strategies to break through.

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 Bannen rabbit hole because But I may get there. But point is, the conversations are very different. That's just a sliver of this. 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? Totally. 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.

No, 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. 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 be competitive with what the other side or people you disagree with are putting out. As you just said, the 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. I've seen our culture has been ceded to the right, whereas maybe my whole life, growing up, culture institutions were more left leaning. Now I think that's really flipped on its head. I think the internet is the battleground for that. I think Conservatives are now in the driver's seat and in the majority of culture. They've 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.

It's because I see online, you watch one video about working out, and then you're in a rabbit hole of RFK Junior, Protein Powder, Joe Rogan, none of which It is in and of itself objectively bad, but altogether, I think it drowns out competing voices, and it's very hard to break through. That's what I tried to do myself.

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?

Yeah, I I have 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. That's what Trump does. It's like a completely clear statement, take it all the way. That's the only thing that really resonates online because everything else, it's too confusing otherwise. The other thing is you have to be controversial or unexpected. It's to be very clear and it'll be very controversial in order to break through, I think. Conservatives are good playing with that without getting in trouble. 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 Democrats lost young men in this election. I think a huge part of that is not because we focus on the wrong policies, but because we seem so risk averse and we seem so cautious. I don't think that, in general, young men find that as attractive as a more risk on, say whatever you want, 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 or 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. 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. 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? What is it? When you talk to your friends, what do they say?

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. I had these real examples of, no, no, no, the Democratic Party cares. They care about working people. They champion health care. They champion immigration, civil rights, all the issues that I considered 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. They grew up in a world with only a few examples. Bill Clinton, we were still really young. You've got George Bush, Obama, and Trump, and Biden more recently. It's like, that doesn't give you a whole lot to go with in terms of what Democrats actually stand for. 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 gender and things which we do and is important, but wasn't always the defining issue of the Democratic Party.

It was not reproductive rights. I mean, that was this campaign. Before that, it was working people, working families, labor, unions, and that's now all on the other side. 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. I haven't heard a super compelling, clear argument from any Democrat about something that really resonates with young people beyond democracy and civil rights broadly.

Does that stuff feel... I mean, I've wondered this, but after the election, I felt like, obviously, the threat of fascism is an issue. Obviously, the threat of rising autocracy is an issue. To 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 talking about things. I'm not even necessarily speaking of how people at their kitchen tables talk about things in Missouri. I mean, you are 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.

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 big and not far enough, and that we got scared of our own shadow in a lot of ways. We were, or at least I find it hard to not believe the narrative that's being fed to me about my party from the other side. It's convincing when you hear it every day.

What do you think the narrative is from the other side?

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

Do you think that... I'm just going to restate. 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 Kamal Harris was the candidate. Was it more than the candidate? It was a bigger issue than that?

Well, 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, who's legislative. I mean, you were there, and you know how much it 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. We saw it toward the end. Toward the end, we started saying ban assault weapons. Toward the end, we started the last day, the Equal Rights Amendment. 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.

We're going to take a very quick break here, but when we come back, more with Jack Schlossberg and the backstory to another one of his viral moments. Stay connected with the MSNBC app, bringing you breaking news and analysis anytime, anywhere.

Watch your favorite shows live, read live blogs and in-depth essays and listen to coverage as it unfolds. Go beyond the what to understand the why. Download the app now at msnbc. Com/app.

Get the all-new CNBC Sport Newsletter.

Alex Sherman brings you exclusive interviews and the biggest news impacting the world of sports business and media. All straight to your inbox. Sign up for free at cnbc. Com/sportnewsletter. Donald Trump is heading back to the White House. Together we can truly make Great America, great again. We are in for an unpredictable but fascinating four years. We're going to be following every twist and turn for the first 100 days. We'll be bringing you the latest updates and analysis first thing every morning.

So join me, James Macu. Me, Martha Kalnett. And me, Mark Stone for Trump 100, every weekday at 6: 00 AM, wherever you get your podcast. You 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 going to go on the record that I find mayonnaise to be the most disgusting thing that exists on the planet. I literally feel faint saying the word out loud, and I can't have it in my fridge. You are a mayonnaise lover.

Or was that just a prank?

Well, I don't know. No, I'm just kidding. I love mayonnaise. Do you actually like mayonnaise? Yeah, I love it. 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... It's just funny. I mean, I refreshed my memory about it before we talked, but I remembered the video.

A lot of people think this is weird, but it is true. Mayonnaise is my favorite food. Mayonnaise? I absolutely love it. I'll put it on anything. I wish I had some right now so I could put it on this. You would not put that on your pizza. 100%, the whole thing will be covered. Dude, that's gross. I know.

How did you come up with that? Did you talk to the Shapiro team? What was the reception?

My whole experience over the campaign was very much how that came together. It was like everything was happening all at once. There was no plan, and that came out of my mouth. Then they did a really good job editing it, his team, and put it up and picked it up. That was a really good moment. Then everyone knew that I love mayonnaise. But I would say that it just shows you that- All the ladies listening.

To decide if that's on your- 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 policy, it's just like, I love mayonnaise.

That's what people to. For some reason, that's familiar. People say, Oh, I hate it, or I love it, or whatever. Then that's how the internet works. It's like, Oh, but meanwhile, I've injected into their minds that Democrats aren't lame because 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? Everyone has a take.

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 pull off things online. Everybody can't, which is a challenge. 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. You have to find the authentic thing, which can be hard. 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. How do you think about that question? When you talk to these campaigns or we're working with them, how did they think about it?

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

Now- I know. We were saying Just 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 I've written an 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 house office building that the world will hear them, and they will not.

Not quite. Yeah. No, I think this was the first time. I can imagine if you asked a politician five years ago, Will you sit down with an influencer and make a video and let them interview for five minutes, whatever they want? They'd Are you kidding me? 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. 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 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 a goofy, silly person and not everybody gets it.

Oh, you're quirky in the best way.

Yeah, but people get it. It's so surprising and encouraging that people are receptive to that. Whereas you would think, 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. I think it shows trust in other people when you're willing to expose different types of your personality. 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. No, it's not really how people work.

In a weird I've thought about how the Trump era has destroyed many things. But I'll just focus on what is presidential and what is presidential aspiring or not. There aren't rules anymore. That's a scary thing, and I'm not even going to 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. It's totally shifted.

Totally. I feel like we ceded the whole internet to the right, and we didn't make anything good on there. Of course, we lost. It's how I see it. What did you think was going to 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? 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. I think that's what I try to do online, is I'm not going to worry so much about someone thinking that I'm not acting the way I should. I'm going to trust that people will get it, and that's okay. Also, by the way, just one thing. You said you didn't want to get into the tech Oh, go ahead.

We can.

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 basically all of the media in our country, and they're all in bed with the current administration. We can't rely now 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. We can no longer expect people to understand what's going on and react to the outcomes of policy when it's completely divorced. This is the biggest propaganda machine that's ever been invented. If we don't get our stuff together and have a coordinated, we need a full-time campaign online like we had during Kam campaign 24/7. It's like, that can't end after the election. They're going. 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.

I think this is also the most important issue I more was like, let me ask you this question first, 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 and insanity. It's insane. You're still on there. I'm still on there, in part because I have 1. 3 million followers, and I'm like, I don't want to 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 strange immense 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 going to buy it. Those platforms together are how the majority of people in this country are consuming news. Yep.

It's like they're driving, you know this, they're driving traditional media as well. Traditional media is now running off of what social media is trending. It's like this is out of control, in my opinion. People are not going to see Trump again and realize that they don't like him like they did before, if they did. It's like, no, this is completely different now. Everyone is convinced that Democrats are actually completely incompetent and only care about purposefully ending the world, and we don't have an answer. We're not funny and we're not entertained. 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. I'm inspired by Chris Murphy. I'm inspired by Gretchen Whitmer, Governor Shapiro, Governor Newsom. Their list goes on. But it's not coordinated and it's not centralized like the other side has.

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 House, they don't have as much money People are on the Sunday. They don't have as much money for people running for President. They can use these platforms. What should they be doing?

Well, I don't know, first of all. I don't know. Everyone's different. But I think that it seems like the candidates who have done well on the Democratic side have been able to pick their own brand of being a Democrat based on where they're at and not having to sign up to every... 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.

Lots of content.

You need to flood the zone. It's like literally half the battle is just getting stuff out there.

Try things. 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. 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. 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. Yeah, no, you do a really good job. Well, thank you for that. But where I would just say, this is this crazy thing happening in DC. People do all sorts of things behind the scenes, makeup, whatever. That's all fine. Different things work for different people. Those are more engaged with than any video we do from the show. It's so interesting because it's just a stream of consciousness thought. But what have you found? Are there things that you thought were going to be people would find interesting and engaging that didn't work and things you've done that have worked?

Yes, I would say I had a hypothesis that attacking would be the best way to get-Attacking?

Attacking. Kind of trolling and attacking other people.

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 have to- Did you get asked out on... Did people ask you on your platforms?

I don't read that stuff, but I'm sure. Maybe. Yeah, maybe.

That's not the way to get to you. I'm not interested in this. You don't read it.

There's some things I know they're going to be controversial. If I talk about one of my family members, if I say something about being Justin Baldon as a lawyer, maybe But there are things like pictures of me doing ballet. That's, I think, my most liked post.

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

For about a year and a half.

Only a year and a half?

Yeah.

My impression was it was something you did as a kid and you just reengaged in it. I wish. I love it. 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 making a point. Are you making a point with doing ballet on your videos?

Of course. Everyone thinks ballet is for girls or something, and it's not. Dancers are the most athletic people in the world. There are 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. I think there's something very manly about it that people don't recognize as manly, maybe. But I also think that it just plays against the trope that you're seeing of manly meaning like, Jack dude who's like this, where it's not necessarily also like, I bet you can't even dance well if you're that jacked. You can't move around that good. That's what I'm saying.

It struck me because, and as I said earlier, I've listened to a lot of us, 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.

I think we got to get over masculinity in general. I think the one way to attract men The worst way to appeal to a young man is to try. If there's one thing that young men don't respect, it's people who try. I feel like if we just- Don't be too thirsty.

Yeah. Just stop.

I'm not going to go 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. 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. If we have to play that game, I'm going to lose and I'm going to look fake.

Next up, I'll talk with Jack about why he's become J. D. Vance's top troll. Stay connected with the MSNBC app, bringing you breaking news and analysis anytime, anywhere.

Watch your favorite shows live, read live blogs and in-depth essays, and listen to coverage as it unfolds. Go beyond the what to understand the why. Download the app now at msnbc. Com/app. The first 100 days, bills are passed, executive orders are signed, and presidencies are defined. And for Donald Trump's first 100 days, Rachel Maddow is on MSNBC five nights a week. Now is the time, so we're going to do it. Providing her unique insight and analysis during this critical time.

How do we strategically align ourselves to this moment of information, this moment of transition in our country?

The Rachel Maddow Show, weeknights at 9: 00 PM Eastern on MSNBC. Stay up to date on the biggest issues of the day with the MSNBC Daily newsletter. Each morning, you'll get analysis by experts you trust, video highlights from your favorite shows.

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

Previews of our podcasts and documentaries, plus written perspectives from the newsmakers themselves, all sent directly to your inbox each morning. Get the best of MSNBC all in one place. Sign up for msnbc. Com Daily at msnbc. Com.

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. Joe Biden and Jill Biden hosted the Trumps for a tea. What in the hell tea 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?

I just can't believe that we keep falling for the same. I mean, I thought when Jill Biden, former First Lady, went to the Notre Dame Cathedral, and then Trump had released all those pictures of Trump cologne with her staring at him. I was like, Are we really going to keep on playing this game and acting like... He acts very polite and private, and then they go and they use it in the most brutal possible way that they can. 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 going to do to us every single time. 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 I'm in the trolling category, you've done Hegset. You've done some things about all sorts of my favorite people. Hegset, JD Vance. Love them. J. D. Your uncle, RFP Jr.

Yes.

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

The Hey JD videos did pretty good. Jd? Jd, I'm at the Senate. I'm at the steps of the Capitol, JD, but you don't think that Trump lost the 2020 election? J. D. I miss you. Hi, J. D. It's me, Jack. I'm at Kamala HQ, and I miss you. I was just thinking about you and wondering why you refuse to accept the results of the in the election. What do I do, J. D? J. D, will you be my dad? Those did pretty good online. I think that my cousin RFK Jr. Is a menace and 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 contemper doctors in the medical community and for all the problems of American health care 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. That's what he preaches, and I think that that's incredibly dangerous and that his anti-vax policies will have bad results for human health across the board.

Plus, he had a dead bear carcass his head in his car. That's the weirdest story I've ever heard in my life.

My sister broke that story. I know. Yeah, amazing.

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

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

That is just a completely crazy thing. You also spend some time. She did some campaigning. You also spend some time as a Vogue correspondent. Yes, I did. The state of the media right now is a part of the problem as well. I think it's fair to state. There's 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. People knew what you believed. What do you think about the state of the media right now?

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. It really matters. 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. I have a lot of appreciation for people who do that because it's not easy. Your second half was about defamation. I think this is one of the scariest things that's happening right now. The Baldony prank was also I have a commentary on that as well. He's suing the New York Times for $250 million for defamation. We're now seeing that this is a much defamation loss changing in real-time. Abc settled their suit with Trump. A lot of people are caving, and it's going to send a chill to publishers, I can only imagine. I don't know what to say about that, but I think that you got to just not play scared. It's like, what are we going to do? 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 a massive mandate to make policy and do whatever he wants. I mean, that's what the American people voted for. What are we holding back for?

It's a good question. You have, 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 have said, I'm not going to family tree. Your uncle started this amazing magazine. Should you do that? Do you ignore all that? Or 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?

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. I think that that's where people are needed right now is actually also... It's hilarious to say that 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 propaganda being used against people, and I'm not going to 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 beg me to just stop For better or worse, I love it, and that's never going to change. I think I plan to stay very engaged and adapt with the times in terms of what that looks like.

It seems like it could be a million things. Are you going to be out there campaigning with people running in tough races over the next two years?

Do you think you're with that again? 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.

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

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

No, it's all good. That's interesting. 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. Let me just end on a more uplifting note. We were talking before we were being recorded, recording what about Senator Chris Murphy and how he gets it on the thread 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.

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 that is what we need to be hitting every single day. He's doing that in no uncertain terms, and he's not his message. But yeah, 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 mentioned. I don't know about their presidential prospects. 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 I just think that it could not be more important. Everyone is on their phone all day long, and every day people are being brainwashed.

That is true. It's important to remember. Jack, I love your quirkiness and weirdness and authenticity. Thank you. I love hearing what you have to think. So thank you for taking the time. Thank you for having me.

This is awesome. Thank you, Jen.

Thank you. Thanks for listening to The Blueprint with Jen Saki. We'll be back next Monday with a new episode. Be sure to subscribe to MSNBC Premium on Apple podcast to get this and other MSNBC podcast ad free. As a subscriber, you'll also get exclusive bonus content. The senior producer for The Blueprint is Margaret Meneffy, and our producer is Vicky 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 Maccarone. Our audio engineers are Bob Mallory and Katie Lau, and Bracen Barnes is the head of audio production. Alex Lupica is the executive producer of Inside with Jen Saki, and Ayesha Turner is the executive producer of MSNBC Audio. I'm your host, Jen Saki. Search for the blueprint wherever you get your podcast and follow the series.

Subscribe to MSNBC Premium on Apple Podcasts. New episodes of all your favorite MSNBC shows now ad-free. Plus ad-free listening to all of Rachel Maddow's original series, Ultra, Bagman, and Deja News. And all MSNBC original podcasts are available ad-free and with bonus content, including Why is this Happening, Velshi Band Book Club, and more. Subscribe to MSNBC Premium on Apple Podcasts.