Jack Schlossberg

Summary

Design Matters with Debbie Millman

Guest: Jack Schlossberg

Episode Date: March 9, 2026

Live from On Air Fest, Brooklyn

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Episode Overview

This engaging episode features Jack Schlossberg, grandson of President John F. Kennedy, who is running for the U.S. House of Representatives. Debbie Millman dives deep into Jack's personal journey, family legacy, struggles with self-confidence, his candid views on politics and media, and his fresh, often humorous approach to activism and digital communication. The conversation touches on generational shifts in media, the Democratic Party’s challenges with new media, and the urgent stakes of upcoming elections.

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Key Discussion Points and Insights

1. Self-Discovery and Family Legacy

• Jack grew up aware but not burdened by his famous heritage. His political consciousness was triggered in 10th grade during a U.S. history lesson on the Kennedy administration (05:08).
• He was a self-proclaimed “bad student,” mentioning struggles with dyslexia and sports, but credits family support for perseverance (06:47).
  • Quote: “I was not naturally a gifted student, but I had a lot of support at home and that that was very lucky.” (07:19, Jack Schlossberg)
• Early activism: In 8th grade, he co-founded Relight New York, promoting energy efficiency in public housing, indicating an early interest in climate issues (07:25).

2. Education and Evolving Worldviews

• At Yale, Jack observed the Democratic Party's ineffective political play and lack of "cool factor," arguing they focus too much on policy correctness over storytelling and risk-taking (10:21).
  • Quote: “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… We forfeited the cool factor.” (11:40, Jack Schlossberg)
• After law and business school at Harvard, Jack’s perspective on environmental advocacy shifted, recognizing the role of infrastructure, economic incentives, and sometimes even compromise with industry (14:59).
  • Quote: “The environmental movement of the future is going to be defined by building massive infrastructure projects… you have to give and take a little bit in order to move things forward.” (15:25, Jack Schlossberg)

3. Views on Politics, Media, and Social Influence

• Jack is candidly critical of the Democratic Party’s loss of narrative control and engagement with younger audiences since Obama (12:21).
  • Emphasizes the right’s dominance in new media and the dangers of ceding these platforms (12:50).
• Advocates for a modern, risk-taking, story-driven approach to digital political engagement.
  • Quote: “Social media is ruining the entire world. But I also think it's our only hope to try to get out of the situation.” (13:42, Jack Schlossberg)

4. The Importance of Humor and Authenticity

• Jack’s digital strategy employs humor and self-deprecation, drawing on lessons from President Kennedy's media savvy (26:48).
  • Reflects on media virality, authenticity, and the fine line between entertainment and meaningful communication (30:40).
    • Quote: “I like to quote Mary Poppins, a spoonful of sugar helps the medicine go down... You gotta get them in there with something unexpected.” (31:15, Jack Schlossberg)
• Responds to criticism fearlessly, for example after his Melania Trump impersonation went viral (27:40).

5. Social Media Realities and Misinformation

• Notes how easily misinformation spreads (“Everything on the Internet is fake, and so I am fake on the Internet.” (32:41, Jack Schlossberg))
• Considers the digital persona a performance distinct from real-life behavior, and recognizes its impact and necessity in politics.
• Stresses the irreversibility of the “post-credibility era” but underscores the possibility of building genuine trust with audiences through consistency and directness (33:44, 34:18).

6. Challenges and Opportunities for the Democratic Party

• Democrats are “risk averse”—especially failing to engage young men who respond more to energy and authenticity than ideology (35:04).
• Maintaining that to change this, politicians must show they're trying, be visible, and “speak their [the audience’s] language” (36:36).
• Cites grave urgency for Democratic digital engagement—arguing the movement is in “code red” (35:04, 37:27).

7. On Running for Congress, Policy, and Civic Duty

• Jack is running to help the Democratic Party reclaim relevance and adapt to the new media environment.
• On platform: Advocates for specific, comprehensible policies—believes voters care about concrete solutions more than abstract principles (25:20).
  • Quote: “People want specific things that they can understand. Those things are really important. But you have to have policies that you can name.” (25:20, Jack Schlossberg)
• Discusses campaigning independently from established power structures and facing resistance from the Democratic establishment (38:52).

8. Current Political and Social Landscape

• Expresses skepticism about prospects for free and fair elections, citing risks of increased authoritarianism and misuse of agencies like ICE (40:22).
• Emphasizes the importance of public engagement, pressure, and direct support for reform-minded candidates as the ultimate political weapon (41:59).
  • Quote: “Politicians are business people. They know they're in the business of being popular, and they respond to public pressure.” (42:35, Jack Schlossberg)

9. Family, Legacy, and Optimism

• Sees his family legacy as a privilege and responsibility to “keep the faith alive” and inspire public service, even if it seems old-fashioned (43:33).
  • Quote: “It sounds quaint now to think of believing in your country, but we don't really have another choice.” (44:24, Jack Schlossberg)

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Notable Quotes and Memorable Moments

• On his TikTok persona:
  “I describe my approach as a silly goose trying to get the truth out there… Humor is a great way to show people that you're willing to fight for them.” (26:33, Jack Schlossberg)
• On being fake online:
  “Everything on the Internet is fake. And so I am fake on the Internet. Like, who I am way… I would never speak in that cadence if it wasn't Instagram.” (32:41, Jack Schlossberg)
• On the stakes of the 2026 election and beyond:
  “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.” (35:04, Jack Schlossberg)
• Family wisdom:
  “My dad is one of the funniest people in the entire world, and he barely ever says a word.” (09:02, Jack Schlossberg)

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Important Timestamps

• Intro & family/media focus: 02:38 – 05:08
• Academic struggles and climate work: 06:47 – 07:45
• On Yale and Democratic messaging: 09:56 – 12:21
• Obama’s “cool factor” and shift: 12:21 – 14:35
• Harvard, environmental law, new perspectives: 14:59 – 16:36
• Stock market views and economic inequality: 16:36 – 17:41
• Campaign, digital strategy, leaving the Biden campaign: 22:05 – 25:16
• Media, virality, truth on social media: 30:40 – 34:47
• Democratic challenges with young voters: 35:04 – 36:36
• Election skepticism and ICE concerns: 40:22 – 41:05
• Civic engagement and hope: 41:34 – 43:33
• Reflections on family legacy & closing: 43:33 – 46:02

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Conclusion

Jack Schlossberg brings a refreshingly humorous, self-reflective, and urgent voice to contemporary American politics. He acknowledges both the gravity and the absurdity of the moment, pushing Democrats to reclaim digital storytelling, take more risks, and engage new generations directly and honestly. Through revealing anecdotes and sharp analysis, he challenges both his party and his audience: “Our best moments have come from people believing we were all in this together.”

For more about his campaign: www.jackfornewyork.com (45:06)

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Transcript

[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. From the Chat 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 episod a conversation with Jack Schlossberg, a young candidate for the House of Representatives who says that Democrats are way behind Republicans in new media. You watch one workout video and you're in this right wing ecosystem of macho dudes saying insane stuff that's all Trump coded.

[Debbie Millman]

Knock knock.

[Jack Schlossberg]

Ooh, who's there?

[Debbie Millman]

A Boost Mobile expert here to deliver and set up Your all new iPhone 17 Pro. Designed to be the most powerful iPhone ever.

[Jack Schlossberg]

You called that a knock knock joke? This isn't a joke.

[Debbie Millman]

Boost Mobile really sends experts to deliver and set up your phone at home or work.

[Jack Schlossberg]

Okay. It's just that when people say knock knock, there's usually a joke to go with it. Like I said, this isn't a joke. So the knock knock was just you knocking?

[Debbie Millman]

Yeah, that's how doors work.

[Jack Schlossberg]

Get the new iPhone 17 Pro delivered and set up by an expert wherever you are. Delivery available for select devices [e-mail], terms apply. Hey, it's Adam Grant from Ted's podcast Work Life, and this episode is brought to you by. ServiceNow AI is only as powerful as the platform it's built into. That's why it's no surprise that more than 85% of the Fortune 500 companies use the ServiceNow AI platform, while other platforms duct tape tools together, ServiceNow seamlessly unifies people, data, workflows and AI connecting every corner of your business. And with AI agents working together autonomously, anyone in any department can focus on the work that matters Most. Learn how ServiceNow puts AI to work for [e-mail] okay, Peloton, let's go.

[Debbie Millman]

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[Jack Schlossberg]

Head to 1peloton.com to learn more about

[Debbie Millman]

the cross training TREAD plus, terms apply.

[Jack Schlossberg]

This interview took place on Wednesday, Feb. 25, 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 paddleboarder, 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. 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 condiment or sauce.

[Jack Schlossberg]

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? Condiment. Ah, 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 so.

[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. We're 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 in 10th grade? 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 Sorenson's biography, Kennedy, Robert Dallek's biography, and A Thousand Days. I Forgot 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. Like, how bad a student were you?

[Jack Schlossberg]

Yeah, like I basically could. I still basically can't read so good. I mean, that's not true. But it took me along. 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 like 30 years and I did grad school and law school and business. 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 that was very lucky.

[Debbie Millman]

Despite your academic challenges, I read that in 8th 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 like professional baseball or something, even

[Debbie Millman]

though you weren't good at sports.

[Jack Schlossberg]

Yeah, exactly. Yeah, I held.

[Debbie Millman]

It's like me wanting to be into musical theater without knowing how to sing. Yeah, 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]

My. I'm so lucky with the parents that I got. They are the coolest people I know. My dad is the one of the funniest people in the entire world, and he barely ever says a word. I have this series.

[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]

Like, 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. 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 1. 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 have. We 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 break through. 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 in 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 of, of hope?

[Jack Schlossberg]

I'm really optimistic and it's hard to, to say that with a straight face it is in 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, in New York. 12 who are so excited, who have never been more wanted to 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 and 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. You know, 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 it, 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 and 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, 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 was never, 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, you know, 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'm very, 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.

[Debbie Millman]

And 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 saying how great everything is. And that to me seems like a fundamental disconnect that is not going to last forever. You know, a 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, an 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, you know, 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 just, 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 like go back and forth between those worlds and have on the one hand, law school during the Kavanaugh hearings, everyone walking out of class go to the business school and everyone is just like 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, he doesn't,

[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, he was like a hotshot professor and I didn't like him. And they were having a debate about climate change in like 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 it shut the person up completely. What, what discount rate are you using? 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? 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, so hence I think your father's

[Debbie Millman]

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 the 2024 election. And so this is the end of 2023. And I unapologetically, absolutely love Joe Biden. I love Joe Biden. I think his first two years in office were 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. 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 do something about this, if I don't say something about this, I'm not gonna be able to live with myself. So I quit. And they. 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, Brad? You think you can. You think it's special for you? No. You're on a campaign. You have to learn what it's like. And I was. 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 have 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, it's tough in the media environment we live in if you don't have someone, and I love President Biden, but if, 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. We just, they, the other side built a whole infrastructure over 10 years. All these like now we have Charlie Kirk, all these, all these right wing people who had huge audiences. And what do we have? We have like trotting out people who had been elected 10 years ago or more. 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, 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, I, you know, 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 curb with, you know, his George magazine. I think they all used humor. My, 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. I think it was the impersonation attempt.

[Jack Schlossberg]

Well, yeah, but I feel like they can take it.

[Debbie Millman]

Yeah, good point.

[Jack Schlossberg]

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[Debbie Millman]

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[Jack Schlossberg]

I've built up, like, 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. 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, like, understanding what's going on. But, yeah, it's math. It's like the algorithm. You know, 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. 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, when media

[Debbie Millman]

outlets falsely reported that you were Justin Baldoni's lawyer, what did. What did that confirm for you about how misinformation or information travel?

[Jack Schlossberg]

I think that's honestly one of the funniest things I've ever done in my life.

[Debbie Millman]

Maybe. Maybe share it with the audience so that they.

[Jack Schlossberg]

Yeah, I don't know, like, backstory. I don't know. A year and a half ago, Justin Baldoni was, like, everywhere in the news and, like, everyone just universally hated him. And so I was fighting with Blake

[Debbie Millman]

Lively about the Elaine Hoover movie.

[Jack Schlossberg]

Like, very tongue in cheek, said that I would be representing him, just like John Adams represented the British in the Boston Massacre. Everyone deserved a trial. And, yeah, they reported it as true. It's 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. Like, who I am way.

[Debbie Millman]

How are you fake?

[Jack Schlossberg]

I would never say the things that I say on the. Not even, like, you know, 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, is not real life. Instagram is Instagram. It's all kind of. 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 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 how, 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 are going on.

[Debbie Millman]

Yeah, I mean, my favorite videos are. Yours are when you take people down and tell the truth.

[Jack Schlossberg]

Exactly. So it's like Justin Baldoni. 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, you know, young men like taking risks. And one way to signal that is humor. That's what gets respect online. And I think that it's. 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. You know, 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. You just have to know there 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 the 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. 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, like in one year. Like, 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 watch. You have to be on the Internet all the time. And then like talking to the Internet and trying to like, it's like 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 were living in a propaganda universe. Now that's never 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. We don't get like 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 they can't. They don't know that 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 the 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 like a classic story throughout human history. People don't want to change, but you kind of 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 like a free and fair election.

[Debbie Millman]

You don't know.

[Jack Schlossberg]

I think this is like, we have, this is like code red. I think, you know, he's going to, 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. You know, ice. ICE is unbelievable. ICE did not exist in its current form before the big beautiful bill was passed. ICE is the large, 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, 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 doing, we're, 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, on a new playbook in 2017.

[Debbie Millman]

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, here 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. People, politicians are. They're business people. They know 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 like 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. And I think I see a young generation, that our campaign slogan is believe in something again. I think that our past. 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, 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? Oh, please.

[Jack Schlossberg]

And help you win, 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. We're like a. We don't. 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. I know that he was himself pretty mischievous. And so I think that 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.

[Jack Schlossberg]

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.

[Debbie Millman]

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[Jack Schlossberg]

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[Jack Schlossberg]

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[Debbie Millman]

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