Jack Schlossberg reflects on growing up in a historic political family, the power and peril of social media, the spread of misinformation, and why authenticity and risk-taking are essential to reaching a new generation of voters.
Jack Schlossberg—writer, lawyer, political correspondent, and the only grandson of President John F. Kennedy—joins live at the On Air Fest to discuss political legacy, internet culture, and the future of Democratic leadership. With humor and candor, he reflects on growing up in a historic political family, the power and peril of social media, the spread of misinformation, and why authenticity and risk-taking are essential to reaching a new generation of voters.
Jack Schlossberg:
I’ve never been less happy to be proven right. It wasn’t actually that complicated. It was just as obvious as it seemed, but you just couldn’t believe that the people in charge had missed it.
Curtis Fox:
From the TED Audio Collective, this is Design Matters with Debbie Millman. On Design Matters, Debbie talks with some of the most creative people in the world about what they do, how they got to be who they are, and what they’re thinking about and working on. On this episode, a conversation with Jack Schlossberg, a young candidate for the House of Representatives who says that Democrats are way behind Republicans in new media.
Jack Schlossberg:
You watch one workout video and you’re in this right-wing ecosystem of macho dudes saying insane stuff that’s all Trump coded.
Curtis Fox:
This interview took place on Wednesday, February 25th, 2026, in front of a live audience at the On Air Fest in Brooklyn.
Debbie Millman:
My guest today, I just want to give you a little bit more background, was born into one of the most storied families in American history. But what fascinates me most about him is not his inheritance, but how he’s choosing to reinterpret it. Jack Schlossberg is the only grandson of President John F. Kennedy, but he is also a writer, a lawyer, a political correspondent, a climate advocate, a paddle border, and an occasional provocateur. At a moment when faith in institutions feels fragile and truth feels negotiable, Jack is asking what leadership looks like now and whether optimism has a place in American life. So I’d like to welcome everybody here in joining Jack Schlossberg and I to this very special live episode of Design Matters on the On Air Fest stage. Jack, I understand that mayonnaise is your favorite food.
Jack Schlossberg:
That’s right.
Debbie Millman:
And it’s somewhat terrifying what I’ve heard you do with it. All over a slice of pizza?
Jack Schlossberg:
That’s right.
Debbie Millman:
Oh, right.
Jack Schlossberg:
I love it. I can’t get enough of it. First of all, thank you all so much for being here. It’s so awesome to see all of you guys here. And thank you so much, Debbie, for having me. This is a real privilege. So this is awesome. You guys are kind of different than the political crowds that I’ve been seeing in my events lately, so this is a lot of fun. Thank you.
Debbie Millman:
Absolutely. So I watched you on the Jimmy Kimmel Show where you had an argument with him about whether mayonnaise is a condiment or a food.
Jack Schlossberg:
Condiment or sauce, it’s a game I invented. And the best part is I always win. So for barbecue sauce, what would you say?
Debbie Millman:
Sauce.
Jack Schlossberg:
See, a condiment. Yeah, that works.
Debbie Millman:
Yeah, I do. But what about the name sauce?
Jack Schlossberg:
Right. But see, it’s misleading and I get to decide which one is.
Debbie Millman:
Okay. I like your politics on this one. You were born into one of the most documented families in American history, but you didn’t know that when you were born. So when did you first realize that your family wasn’t just any family?
Jack Schlossberg:
Well, I think I probably absorbed stuff at a young age, but there’s one moment that stands out for me that really lit a fire for me, which was I was in 10th grade and we were studying US history and we were studying the Kennedy administration. So I felt awkward and I was goofing off in the back of class, which was usual for me. And the teacher saw me goofing off, distracting everybody and tried to make a point and called on me and asked me, “Jack, what’s the Kennedy administration’s policy in Laos?”
Debbie Millman:
In 10th grade.
Jack Schlossberg:
In 10th grade, yeah, Laos, which has taken me a long time and I’m still not at the bottom of it. But yeah, so I was so mortified by that that I went home and I wasn’t much of a… I never really read for pleasure at that point in my life, but I went home and I asked my mom what books I should read and she gave me three books and I just started reading them all. And then I started watching all my grandfather’s speeches and got really, really interested in it. And that was kind of coincided with the 2008 election, Barack Obama. And that’s kind of when I just discovered that I was obsessed with politics, whether I liked it or not. It felt like it chose me. And I got super motivated by it and wanted to learn everything I could because I found it so inspiring what President Kennedy stood for and I never, ever wanted that to happen to me again.
Debbie Millman:
Do you remember what three books your mom gave you?
Jack Schlossberg:
Yeah, there’s Ted Sorensen’s biography, Kennedy, Robert Dallek’s biography, and A Thousand Days. I forget the author.
Debbie Millman:
Now, I read that growing up, you actually felt like you weren’t particularly good at anything.
Jack Schlossberg:
That’s right.
Debbie Millman:
And that you were actually a bad student. How bad a student were you?
Jack Schlossberg:
Yeah. I still basically can’t read so good. And that’s not true, but it took me a long… I was very dyslexic. I was really bad at math. I was really bad at sports. I wasn’t that cool, but I was always a little bit funny. That’s probably how I got funny. But yeah, I was not naturally great at school. And for some reason I decided to go to school for 30 years and I did grad school and law school and business school. So I kind of overcame that. But yeah, I was not naturally a gifted student, but I had a lot of support at home and that was very lucky.
Debbie Millman:
Despite your academic challenges, I read that in eighth grade you co-founded a nonprofit named ReLight New York, which was an organization that installed energy efficient lights in low income housing developments that seems to fly in the face of not being particularly good at anything.
Jack Schlossberg:
Well, I’ve always really cared about climate and the environment. I remember seeing Inconvenient Truth, like a lot of us probably did, and just being shocked by it and wanting to do something about it and feeling like that was the thing I cared most about. So yeah, I started this program with some of my friends in school. We installed fluorescent light bulbs in public housing around the city, which was energy efficient. It was more than anything, a really cool way to see NYCHA, New York City Public Housing Authority, and see how that system works and get to know the people who live there.
Debbie Millman:
At that point, what were you imagining you might do with your professional life?
Jack Schlossberg:
Oh my God. Probably professional baseball or something like that.
Debbie Millman:
Even though you weren’t good at sports.
Jack Schlossberg:
Yeah, exactly. Yeah.
Debbie Millman:
It’s like me wanting to be into musical theater without knowing how to sing.
Jack Schlossberg:
Yeah.
Debbie Millman:
Yeah. In one of your TikTok stories, you ask your dad, the legendary designer, Edwin Schlossberg, if you should do what you love or what he wanted you to do, and very enigmatically as your father can be, he didn’t answer or you never shared what your dad said. And I’m curious, as you were growing up, did you envision doing something professionally that your family was supportive of or were they pushing you to do something else?
Jack Schlossberg:
I’m so lucky with the parents that I got. They’re the coolest people I know. My dad is one of the funniest people in the entire world, and he barely ever says a word. I have this series on my-
Debbie Millman:
He’s enigmatic.
Jack Schlossberg:
He really is. I have this series on my Instagram where I ask him really obvious questions. So I say, “Hey dad, what’s more important? Money or love?” And then he doesn’t answer. And it’s a very popular-
Debbie Millman:
And he goes on making his tea or making a sandwich.
Jack Schlossberg:
The purpose is just to really, really annoy him. And he’s a great straight man. But no, I mean, I’m very close with my parents and in a lot of ways I’m like them, in a lot of ways I’m nothing like them, but they never really pressured me into anything. If anything, they tried to take the pressure off. But I don’t know, I can’t see myself ever doing something that they wouldn’t like except for posting crazy videos on the internet.
Debbie Millman:
Well, we’ll talk about that in a bit. In the meantime, you went to Yale University where you wrote for the Yale Daily News. You were editor of the Yale Herald and in an article titled in Rally Behind the President, you argued that Democrats do not always play the game of politics correctly. Now that was 12 years ago or so. Do you think that’s still true?
Jack Schlossberg:
Yeah, I think I’m a Democrat. I bleed blue. I believe in the Democratic Party. I believe in it because I know the history. And to me, a Democrat is somebody who has been fighting for decades for civil rights, for working people, for labor, for immigration reform, for sensible economic policy that has a party that has a job record that beats the Republicans 50 to one. So I feel like that story and that history and that association is not something that a lot of people my age or younger really have with the Democratic Party. And I think it’s hard when you are competing against another side that, in my opinion, plays by different rules, doesn’t feel obligated to tell the truth or explain or be correct on policy. Meanwhile, Democrats are busy trying to get the answer right. And I think, obviously, I don’t want us to get the answer wrong.
And the only reason to be in politics is to try to make a smart policy, but I think we’ve forfeited the cool factor. We forfeited the kind of counterculture factor. And I don’t know how Democrats became associated with being stale, being stuck in the past, risk averse. That’s not what I think of when I think of a Democrat. That’s kind of what I think of when I think of a Republican.
So I think in a lot of ways, Democrats hamstring themselves by trying to get the answer right, trying to explain the problem and don’t remember to be funny, take risks, tell stories. And I think that that’s why I’m running for Congress. One of the reasons is I think it doesn’t have to be that way. I don’t think that we need to just forfeit that to the other side. I don’t think we need to forfeit social media following to the other side. And I think that there’s absolutely no reason that we can’t be cool, fun, edgy, and breakthrough because at the end of the day, I think our policies are way more popular with the American people than the other side.
Debbie Millman:
It seems that that cool factor left us after Obama left office. I mean, he is still one of the coolest dudes in the universe. So how that happened is something that I think people are trying to understand. And in many ways it’s a branding and positioning exercise because how did we lose that so quickly? I mean, we’re talking about a decade. What do you see as the future-
PART 1 OF 4 ENDS [00:11:04]
Debbie Millman:
What do you see as the future of hope?
Jack Schlossberg:
I’m really optimistic and it’s hard to say that with a straight face-
Debbie Millman:
It is.
Jack Schlossberg:
… given what’s going on right now, but I really am. I really am because I have met so many young people all across the country campaigning in 2024 and now campaigning in Manhattan and New York 12 who are so excited, who have never been more want to get involved, want to volunteer, want to sign up, want to make videos on their Instagram and tell people what they think. And that’s the power that always wins in the long run. So, I’m very optimistic that we can become cool again, but I think it’s going to take a long time because we are behind right now and we’re going to be behind for a long time.
Because what you’re saying kind of since Obama, he galvanized people in a way that was completely new at the time. He was the first person to have social media in 2008 in Twitter and he was on the cutting edge of that. And we fell back and we rested on our laurels and we seeded the whole internet and the new age media to the right, which invested in talent and lifted up fringe voices that then became kind of mainstream where we didn’t. No Democratic politician really had an Instagram until a year ago. And so, Instagram, social media is not everything, but you have to compete there if you want to win.
And that’s one thing that I’m trying to do with this campaign because I think social media is ruining the entire world, but I also think it’s our only hope to try to get out of the situation because at the end of the day, it can be very democratic and it does favor people or the party that is on the side of the people. And yeah, that’s what I’m trying to do.
Debbie Millman:
After Yale, you went to Japan, you did some work in the private sector and then you went to Harvard and you described going into Harvard as a super liberal thinker and leaving with the realization that you hadn’t known what you were talking about before. What fueled that evolution and how do you think differently now?
Jack Schlossberg:
So, I’ve always been very progressive, very liberal, and I went to school to be an environmental lawyer and I worked at the environmental law clinic. I also got my business degree when I was there. And yeah, I think especially in the context of environmental law, so much of the story I was told was demonizing development and industry and energy companies. And while I think there’s a lot of truth to that in merit, I think that the left often forgets that we have the obligation to actually try to make things… We’re actually trying to make things better. So, I think the environmental movement of the past is defined by stopping development.
The environmental movement of the future is going to be defined by building massive infrastructure projects. And to do that, you need to have capital available, you need to have low interest rates, and that means you need to have cheap energy, which means you don’t actually want to cut off all the fossil fuel production in the US. You want to make energy cheap and available so people can invest in long-term infrastructure projects. That wasn’t a calculation that I ever thought about before. And environmental law and environmental issues really are often about industry versus the public interest, public safety.
And so, it’s a lot more complicated when you look at it and you learn what the dynamics are that not all development is bad, not all industry is bad. You have to give and take a little bit in order to move things forward, otherwise you just risk creating an economic situation that the first investments to go when the economy slows down are investments in renewables. So, you can’t really afford to have recession. You can’t afford to have expensive energy prices if you want to build huge infrastructure projects. So, that’s just maybe one example.
Debbie Millman:
How are you feeling about the stock market?
Jack Schlossberg:
I follow it very closely. I think it’s not real right now. I think it’s kind of inflated. And I think that we’re in for a huge correction is my prediction, but I also think it could last for a long time. And…
Debbie Millman:
The correction or the bubble?
Jack Schlossberg:
The bubble. And I think that it’s really crazy to go around New York 12, the district I’m running in Manhattan. Everyone talks about affordability. Everyone’s talking about how they can’t pay their rent. Everyone’s talking about how food prices are so high and it’s so hard to live in the city. And then meanwhile, you have stock prices at record highs and Wall Street’s saying how great everything is. And that to me seems like a fundamental disconnect that is not going to last forever. In fact, I recently learned the top 1% of income earners in America own 88% of the stock market. The next 10% own the remaining 12 and then the bottom 50% are in debt. So, how does that seem like it’s going to work long-term?
Debbie Millman:
Right. I asked your dad for one question that I should ask you and not surprisingly, it was enigmatically funny. You graduated from Harvard in 2023 with a joint law and MBA degree. He wants to know why.
Jack Schlossberg:
I was hedging my bets. I knew I wasn’t sure I wanted to be a lawyer. I thought I couldn’t read a graph or a spreadsheet before I got there and I thought business school sounded like a good idea. And I thought there would be no better way to understand environmental issues or prepare yourself for public life than to study it from both sides. And I think that that was true. I think that there’s a lot of siloing in the law school that leads people to have a certain mentality about business. And the business school is so unbelievably… They call it the West Point of capitalism, which is absurd to me. And it’s an aggressive… Nobody cares about politics at all over there. They don’t ever talk about it.
So, it was really interesting for me to go back and forth between those worlds and have on the one hand, the law school during the Kavanaugh hearings, everyone walking out of class, go to the business school and everyone is just super happy about to go on a trip.
Debbie Millman:
What do you make of that in terms of the potential leadership of the future?
Jack Schlossberg:
I think that I hope more of the law students are in charge.
Debbie Millman:
Interesting.
Jack Schlossberg:
Yeah.
Debbie Millman:
I’ve been doing some work with the Harvard Business School and I’ve been in some of the Harvard Business School classes and it is astounding to me how much diversity there is in the student body, but also how much diversity there is in thinking and how I could see very clearly how you might go in as a super liberal and then have a lot of your ideas challenged by the other super smart students that are in the classroom. What is one big thing that you really felt was changed by your experience in the classroom with less than liberal thinkers?
Jack Schlossberg:
Oh my God, I remember it so well. So, there was this guy…
Debbie Millman:
He didn’t have any of these questions, by the way. Not a one. I did not give him anything in advance.
Jack Schlossberg:
There was this professor who was like a hotshot professor and I didn’t like him. And they were having a debate about climate change in an after class kind of seminar. And this guy was basically arguing for why we shouldn’t do anything about climate change and it was driving me insane. And I was like, “How can this person be telling a room full of young people that this doesn’t matter?” And I remember it so well because some student raised their hand and said, “Well, it’s going to cost us this, this, this, this much money if we don’t do anything about it.” And he said, “What discount rate are you using?” And shut the person up completely.
Debbie Millman:
Wait, which what?
Jack Schlossberg:
What discount rate are you using?
Debbie Millman:
Oh.
Jack Schlossberg:
Meaning, how are you getting that number and are you really factoring in all the lost productivity that comes with all the regulations that you’re talking about? And then my light bulb in my head went off because it was just like, I hate this guy so much and he is wrong, but he’s also right about what he’s saying that you can’t just kind of make these sweeping arguments about how we need to shut down all industry if you don’t consider the effect that that’ll have, like I was just saying. And I remember just being like, “That is so hard to argue against.” And then I learned, then I had to figure out what a discount rate was.
Debbie Millman:
What is a discount rate?
Jack Schlossberg:
Well, have you ever heard time is money?
Debbie Millman:
Mm-hmm.
Jack Schlossberg:
A dollar today is worth more than a dollar tomorrow. So, a discount rate is the rate that you use to value future earnings. So, a higher discount rate means like interest rates. It’s basically an interest rate. So, how much are you valuing money today versus money tomorrow?
Debbie Millman:
I don’t think there’s anyone in the room that woke up this morning thinking today is the day I learn about a discount rate. You graduated in Harvard in 2023. You passed the bar the next year on your first try, Bravo, one of the first in your family to do that. In fact, you scored in the top 1% with a 332. Now armed with a law degree and an MBA, you then went to work for Vogue Magazine.
Jack Schlossberg:
Yes. Well, something actually happened in between that.
Debbie Millman:
Hence, I think your father’s curiosity about the degree.
Jack Schlossberg:
So, I finished law school and business school, took the bar, thought I was going to be a lawyer, but I saw on the horizon something coming and it was a 2024 election. And so, this was the end of 2023. And I unapologetically absolutely loved Joe Biden. I love Joe Biden. I think his first two years in office are the best kept secret in politics. It was a progressive person’s dream. He got more legislation passed than any president since FDR. Historic investments in infrastructure, green energy, he protected civil rights. He did so much good for our country and nobody knew, especially people my age and nobody knew.
And I was looking at my phone on the internet and it was just like, you watch one workout video and you’re in this right-wing ecosystem of macho dudes saying insane stuff that’s all Trump coded. And I was seeing this and all my friends, we all saw it and I was like, “This is a huge problem.” So, I was like, “I’m going to go work for the Biden campaign.” So, I got hired by the Biden campaign. I signed a contract. I went down to Wilmington. They hired me to make social media videos and do young voter contact. So, I said, “Okay, well, I have some ideas for videos. How about this video?” No. “How about this video?” “No.”
“How about this video?” “No, Jack, why don’t you just go down to the basement and just work on some memo?” And at the same time, my cousin RFK Jr., He was still running as a Democrat then, and he was using President Kennedy’s name and image and likeness to kind of promote his campaign. And I could see from a mile away that he was working with Trump and it was all a scam. And I thought, if I don’t…
PART 2 OF 4 ENDS [00:22:04]
Jack Schlossberg:
… That he was working with Trump and it was all a scam. And I thought, if I don’t do something about this, if I don’t say something about this, I’m not going to be able to live with myself. So I quit and it was very scary. These people who are super high up in Democratic politics, who I really respected, who had hired me were, “You entitled brat. You think it’s special for you? No, you’re on a campaign. You have to learn what it’s like.” And I freaked out, but I was like, “You know what? I have to do this my way.” So I started making videos and everyone said, “These videos are crazy.” And they did so well and broke through in such a crazy way that a month later the campaign called me and they said, “Hey, can you come speak at the DNC? Can you go to every single swing state and campaign for us? Will you be a delegate for New York?” And that was kind of when I got hired by Vogue after making those videos.
But that was a huge lesson for me, which I’ve never been less happy to be proven right, which was we had missed our chance way behind the eight-ball. And it wasn’t actually that complicated. It was just as obvious as it seemed, but you just couldn’t believe that the people in charge had missed it. And that gave me a lot of confidence. And I don’t think I’d be running right now if I didn’t have that confidence because a lot of people when I announced for Congress said it was a terrible idea, “You can’t win. The local political machine is too strong here. Why don’t you go do something else and maybe in 20 years?” And if I hadn’t had that experience of being like, “I don’t know. I think we kind of got to shake things up a little bit,” then there’s no way that I would’ve had the confidence to do it. But that was a huge wake-up call.
Debbie Millman:
What was the biggest thing we got wrong in 2024?
Jack Schlossberg:
I mean, the whole entire thing. I mean, it’s unbelievable what happened. I mean, President Biden’s decision to run again wasn’t a great one. Not having a primary wasn’t great. But I really think it’s tough in the media environment we live in, if you don’t have someone … And I love President Biden, but if the person can’t talk, it’s really hard to compete on social media. It’s just really, really hard. And we didn’t have anybody out there. The other side built a whole infrastructure over 10 years. Now we have Charlie Kirk, all these right-wing people who had huge audiences. And what do we have? We have trotting out people who had been elected 10 years ago.
Debbie Millman:
Or more.
Jack Schlossberg:
Right. But yeah, I think the biggest thing we got wrong was talking high level, abstract, constitution, democracy, rule of law. People want specific things that they can understand. Those things are really important, but you have to have policies that you can name. And that is something that I’m trying to put forward in our campaign by releasing specific policy plans that people can understand that relate to their specific concerns, because that’s what the Democratic Party has to do.
Debbie Millman:
You have described your approach to social media as a silly goose trying to get the truth out there. Given the gravity of your family history, where did that instinct, that humor instinct come from?
Jack Schlossberg:
Well, there’s so many lessons to be learned from President Kennedy and from other members of my family, but I think one of them is just being really savvy with the media transition of their moment. And President Kennedy was the first television president. My uncle John was way ahead of the curve with his George Magazine. I think they all used humor. My grandfather was famously quick-witted and funny. And I think it’s kind of a attitude of not taking it all too seriously because you know how serious it is and you want people to enjoy it and not be put off and be so preachy to them that you’re willing to make fun of yourself. I also think humor is a great way to show people that you’re willing to fight for them. If you’re willing to make fun of yourself or somebody else on behalf of a group that is being attacked, then I think that that shows people that you can be counted on to step up when it’s hard.
Debbie Millman:
Yeah. You don’t seem to be afraid of being criticized.
Jack Schlossberg:
No, not at all.
Debbie Millman:
Which is refreshing. The Melania …
Jack Schlossberg:
Yeah. I don’t know why that flipped everybody out. All I did was put on a wig. What’s the big deal? Why is that so bad?
Debbie Millman:
I think it was the impersonation attempt.
Jack Schlossberg:
Well, yeah. I feel like they can take it.
Debbie Millman:
Yeah. Good point. You’ve said it’s harder for a positive message to spread online than a take down.
Jack Schlossberg:
For sure.
Debbie Millman:
And that you’ve experimented with combining strong opinion and serious facts so that they travel. Are you studying virality the way previous generations studied rhetoric?
Jack Schlossberg:
I’ve built up an instinct, I would say, based on my own instincts. And also you get so much information based on likes and sharing and all that stuff. And it changes over time. The internet changes really rapidly. What did well a year ago doesn’t do well, and what did well six months ago, you have to change it up.
Debbie Millman:
How do you know how to do that? How do you know when to do that?
Jack Schlossberg:
I think part of it’s being online all the time or understanding what’s going on. But yeah, it’s math. It’s like the algorithm, if your face is not really close up in the first 0.2 seconds, the algorithm will kill it.
Debbie Millman:
Really? Why?
Jack Schlossberg:
Oh yeah. That’s just how it works. And if you aren’t talking about something that everybody’s talking about that day, nobody cares. So it’s a balance between … I like to quote Mary Poppins, “A spoonful of sugar helps the medicine go down.” So if you’re going to talk about facts, which people actually respond to really well, the videos that do the best are the ones with the most information. You got to somehow get them in there, get them watching where there’s something unexpected. Whereas if you just sit there and say, “I’m going to talk to you about the facts and this is what’s going on,” it’s like next.
Debbie Millman:
When media outlets falsely reported that you were Justin Baldoni’s lawyer, what did that confirm for you about how misinformation or information travels?
Jack Schlossberg:
I think that’s honestly one of the funniest things I’ve ever done in my life.
Debbie Millman:
Maybe share it with the audience so that they [inaudible 00:28:03] backstory here.
Jack Schlossberg:
I don’t know, a year and a half ago, Justin Baldoni was everywhere in the news and everyone just universally hated him. And so I was-
Debbie Millman:
Fighting with Blake Lively on the Colleen Hoover movie.
Jack Schlossberg:
I very tongue in cheek said that I would be representing him just like John Adams represented the British in the Boston Massacre. Everyone deserves a trial and yeah, they reported it as true. It was just unbelievable.
Debbie Millman:
So what did that tell you? What did that give you the sense of the media and the reach?
Jack Schlossberg:
It’s all fake. Everything on the internet is fake. And so I am fake on the internet. Who I am on-
Debbie Millman:
In what way? How are you fake?
Jack Schlossberg:
I would never say the things that I say on the … Not even risque, just more like in the way that I say them, I would never speak in that cadence. I would never do it like that if it wasn’t Instagram. Instagram is not real life. Instagram is Instagram. You can’t take it too seriously. I mean, think about what Trump does every single day. He just trolls us. He trolls us in some way. He tries to get us outraged so that we focus on something and he does something behind the closed doors. So it’s like, okay, what would they love? If I was representing Justin Baldoni. Give it to them.
Debbie Millman:
You’ve said that people will print and believe anything. And that’s a somewhat terrifying thing for someone who loves democracy to say. Do you feel like we’re in a post-credibility era? And if so, how do we work with that? Because if we are, it doesn’t seem like we’re ever going to go back.
Jack Schlossberg:
Yeah, I don’t think we are going to go back. I think that’s true, but I think that you have the opportunity to build real trust with an audience one-on-one. So I’ve been able to do that. And people who I meet every day on the street who are, they thank me for my videos, which I can’t believe. It’s the funniest thing in the world because it’s like it’s just a stupid video, but people appreciate that because for a while, nobody was willing to say anything about certain things that were going on.
Debbie Millman:
Yeah. I mean, my favorite videos are yours and when you take people down and tell the truth.
Jack Schlossberg:
Exactly. So it’s like-
Debbie Millman:
Justin Baldoni.
Jack Schlossberg:
That was more just for me.
Debbie Millman:
I know.
Jack Schlossberg:
I think you can build a real trust with your audience so that they trust you in a way that’s not necessarily they don’t have to fact check you. They understand where you’re coming from. And I think that is a huge advantage and something that the Democratic Party really needs right now is to have people in Washington serving in government who have that preexisting relationship with people that they can build on. Because if you’re trying to start an Instagram up as a politician, no one’s going to believe you.
Debbie Millman:
Right. You’ve argued that Democrats struggle online because they seem risk-adverse, especially with young men. Do you think what young voters are responding to is ideology or energy?
Jack Schlossberg:
I think it’s a little bit of both. I think young people are really, really smart and they can tell kind of this authenticity thing so quick. But yeah, I think that not taking risks is … Young men like taking risks and one way to signal that is humor, that’s what gets respect online. And I think that we’re in a code red situation. This is our last chance to stop Trump. We don’t know what comes on the other side if we don’t take back the House. The House of Representatives is what certifies an election. And if the House of Representatives isn’t controlled by Democrats, we can’t investigate any of the stuff that we’re seeing going on right now that is clearly against the law, any of the corruption that we’re seeing that is clearly against the law. Studies show that if someone votes for a party twice in a row, they’re very likely not to ever change for the rest of their life. And I think we have lost a lot of young men.
And I’m the last person to talk about the plight of young men, but it’s just true. I went campaigning all across the country in 2024 and I met thousands of young people, thousands of young women. I would show up on a college campus. There was like two guys and I was like, “This is not good. This is not good for the Democratic Party.” But I do think that it’s not that hard to change it. You just have to try. People don’t want a superhero, some genius. You just have to be out there trying, putting something out there, meeting people where they are. They don’t want a superhero. They just want you to be trying, speaking their language.
Debbie Millman:
Help me understand what young men find so appealing about the current political environment.
Jack Schlossberg:
Well, I mean, all of us, maybe we can’t take our eyes off of it. I can’t take my eyes off of it. I feel like I have to pay close attention. And I think that having license to do whatever you want, say whatever you want all in it for yourself, don’t worry about, you don’t have to believe in anything. All the rules are broken. Just it’s all about what you can get out of the system …
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Jack Schlossberg:
… broken just, it’s all about what you can get out of the system. I think that appeals to people who don’t feel like they have much control over their own lives. But I also think the internet is just ruining people’s minds. I think that no wonder we have Trump, everyone got an iPhone in one year. We all now have phones and we’re all connected to them all the time. Of course, there’s a propaganda machine that can take over that.
Debbie Millman:
You’ve said that social media companies are effectively aligned with the administration. We saw that in the inauguration with the folks sitting up there watching the festivities. They are now producing a daily alternate version of reality. What does opposition to that even look like now?
Jack Schlossberg:
You have to counter them in real time. It’s really hard. You have to put out stuff all the time. It’s a full-time job. It’s relentless. It’s not fun. You have to be on the internet all the time and then talking to the internet and trying to… It’s not just being a creator like fun. It’s like being a journalist trying to do difficult reporting. It’s not the same as what it used to look like. I don’t know. Elon Musk controls X. We all know this. Zuckerberg controls Instagram. Trump owns Truth Social. Look at where these people put their money. They put it all in digital media. We’re living in a propaganda universe now that’s most powerful ever that has ever existed. And if you don’t have people who can break through on their own with their own trusted voices, we’re so screwed and time is running out.
And I just don’t understand how the Democratic Party doesn’t get it. They’re trying now, which is great. But I mean, I get so much pushback running for this seat and people are so hostile and they hate that I’m doing it.
Debbie Millman:
Why?
Jack Schlossberg:
Because I don’t owe them anything. And that’s ultimately politics is a lot of its trading favors. And I don’t owe the local Democratic clubs or whatever anything because we don’t know each other. And I’ve now met them all and done my best, but they don’t want to change. And I think that that’s a classic story throughout human history. People don’t want to change, but you have to, and I’m going to try to just make it happen. And I think I can.
Debbie Millman:
You said that you’re doing this because there needs to be someone in office who could stand up to President Trump and his allies. What would be the first thing you would do when you’re elected?
Jack Schlossberg:
Well, I think the most important thing Democrats have to do… I mean, if I won the primary, I would then go campaign around the country because we need to win back the house. If we don’t win back the house, this whole thing is over. I think the most important thing that we need to do once we get it is to… If you control the house, you control the judiciary committee. If you control the judiciary committee, you can subpoena people. You have to investigate all of the stuff that we’re seeing, otherwise it’s all going to go unanswered and become the new normal. So I would be very excited to call certain cabinet officials before Congress and find out why they’re saying what they’re saying, who’s paying them, and let the American people know that this is all a scam. So I think investigating and prosecuting has to be the number one priority.
Debbie Millman:
What are the odds of our getting the house back?
Jack Schlossberg:
I don’t think there’s going to be a free and fair election.
Debbie Millman:
You don’t?
Jack Schlossberg:
No. This is code red. I think Trump is going to do something insane. I think it’s going to probably get more violent before it gets more peaceful. And they’re already sowing the seeds with ICE. ICE is unbelievable. ICE did not exist in its current form before the Big Beautiful Bill was passed. ICE is the most well-funded and largest criminal law enforcement agency in the history of the United States. We spend more on ICE than we do on all other federal law enforcement combined, and it’s all under the direct control of the president. And so he can send ICE in when we have elections, no problem. And I think that that’s a very real threat.
Debbie Millman:
How do we combat that? How do we create any kind of coalition to protest?
Jack Schlossberg:
I think we’re having a good start. I mean, Minneapolis is unbelievable what the people there have been doing and people here get it. So I think people’s willingness to be so engaged in politics right now is evidence of the fact that this is not going to last, but we just have to stay at it and be organized and be willing to take risks on a new playbook.
Debbie Millman:
In 2017, you said, “When it seems like things couldn’t be any worse, there are opportunities.” I think things have gotten way worse since 2017. What are the opportunities? What do you see as the ways in which people in this room, us, can rise to the occasion right now and make a difference?
Jack Schlossberg:
It’s going to sound cliche or maybe unsatisfying, but if you can support candidates who you think are doing a good job and not playing by the rules that have been used so far and are… There are a lot of them. There are a lot of people running across the country in Maine, in New York, all over. And if you can support them in any way, either by vocalizing that online, sending them a small amount of money, going to their event, anything, just being involved in politics and showing up, it makes a huge, huge difference. And think about the two things Democrats have been able to do since Trump got elected the second time, is Epstein files and shutting down DHS and getting body cams for ICE.
I wish it was more than that, but those are the only two things where public pressure has really been applied. And that still is the ultimate political weapon, is public pressure. Politicians, they’re business people. They’re in the business of being popular and they respond to public pressure. So everyone who makes a video, everyone who shares it, it seems meaningless, but it’s actually not. So I think that honestly, as crazy as it sounds, be on your phone more.
Debbie Millman:
I’ve had the privilege of interviewing both you and your father and your sister. What struck me in all of the conversations that I’ve had was the deep seriousness about ideas and about responsibility. How do you think about your own role inside your family’s legacy?
Jack Schlossberg:
I grew up and I took it all really seriously. I took all the words of President Kennedy really seriously. I took seriously the fact that a generation fought fascism and then came home to the United States and passed the most strongest protections for individual rights, civil rights, anywhere on earth, that we’re all in this together, that it all really actually mattered at the end of the day. Our campaign slogan is, “Believe in something again.” This is our nation’s 250th birthday. I think our past, we haven’t always lived up to the ideals of our founding documents, but our best moments we have tried to advance the ball. And I think that’s because people believed that we were all in this together, that it was worth participating in politics, that it wasn’t all rigged against you and that your vote counted.
And I still believe. I still believe in politics because I hear stories of people who tell me about my family members and that they genuinely inspired them to enter public service. And I know that that’s all true. And it sounds quaint now to think of believing in your country, but we don’t really have another choice. So I feel like my real privilege in life, I have many, but it’s really to be connected to a past where politics was an inspiring, noble profession, that that actually happened and that there were real results that came out of it. That’s my responsibility is to keep the faith alive and to not stop believing and quit.
Debbie Millman:
For anyone that wants to support your campaign, where can they go to get more information?
Jack Schlossberg:
Oh, please.
Debbie Millman:
And help you win.
Jack Schlossberg:
Please go to www.jackfornewyork.com. We have all of our policies, our plans out there. We have merch, which is pretty cool. And you can donate, you can sign up to volunteer. We really need volunteers. We’re going to win because of our huge volunteer base and we need people to come show up and knock on doors. And it’s really fun. I’m the campaign manager and it’s all young people who were just really scrappy and all working as hard as we can.
Debbie Millman:
You mentioned before that your grandfather was the first television president. If he were alive and watching you on TikTok, what do you think he’d say?
Jack Schlossberg:
I don’t know what he would say, but I know that he was himself pretty mischievous. And so I think he would be on his Instagram all the time.
Debbie Millman:
Jack Schlossberg, thank you for giving me some hope about the future of our country.
Jack Schlossberg:
Thank you.
Debbie Millman:
And thank you for joining me today at the On Air stage. Thank you. Thank you.
Curtis Fox:
Design Matters is produced for the TED Audio Collective by Curtis Fox Productions. The interviews are usually recorded at the Masters in Branding Program at the School of Visual Arts in New York City, the first and longest running branding program in the world. The editor-in-chief of Design Matters Media is Emily Weiland.