Design Matters with Debbie Millman

Guest: Jack Schlossberg

Episode Date: March 9, 2026

Live from On Air Fest, Brooklyn

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.

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)

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)

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

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)