Gabe Fleisher on Values-Driven Journalism | B:Sides: The Deeper Side of Leadership

Why It Matters

Fleisher’s values‑driven, independent newsletter demonstrates a scalable path for young creators to rebuild public trust in news, reshaping how the next generation engages with politics.

Key Takeaways

• Gabe founded Wake Up to Politics at nine, now 50k subscribers.
• Independent Substack model lets him monetize while keeping free content.
• Values from his rabbi father—tikkun olam, truth‑seeking—guide journalism.
• Direct email format builds personal trust absent in large media institutions.
• Gen Z’s political engagement is nuanced; distrust coexists with activism.

Summary

In this Aspen Institute interview, Gabe Fleisher recounts how a morning email to his mother at age nine evolved into Wake Up to Politics, a daily newsletter now read by 50,000 subscribers, including policymakers in Washington. The conversation highlights Fleisher’s transition from a hobbyist to a paid Substack creator, emphasizing the independent model that offers free weekday content and a premium weekly edition, allowing him to sustain journalism without corporate constraints. Fleisher attributes his journalistic ethos to his upbringing as a rabbi’s son, invoking the Jewish concept of tikkun olam and a habit of “wrestling with authority” to pursue truth. He stresses the intimacy of email—direct replies, transparent sourcing, and public corrections—as the cornerstone of the trust his audience places in him, contrasting it with the impersonal nature of legacy newsrooms. The discussion underscores a broader lesson for media: independent platforms can cultivate credibility and civic engagement, especially among a skeptical Gen Z cohort that simultaneously distrusts institutions yet seeks authentic political participation.

Original Description

B:Sides: The Deeper Side of Leadership, hosted by Lorelle Atkinson, explores the human stories behind impactful leadership—going beyond titles, résumés, and highlight reels.

In this episode, Gabe Fleisher, journalist and author, talks about growing up in the public eye, why trust in media is fraying, and how independent journalists can help repair it. He shares lessons from his father’s rabbinical teachings, insights into Gen Z’s unique approach to politics, and the simple reason he still writes like he’s talking to his mom over breakfast. If you care about honest, accessible, values-driven journalism, you won’t want to miss this episode.

Through candid conversation, this series brings forward the experiences, values, and decisions that shape how leaders navigate complexity and create change.

About the series:

B:Sides features conversations with changemakers across sectors—from tech innovators and independent journalists to farmers, bankers, and artists—who are reshaping their fields while staying grounded in purpose.

Release schedule:

New episodes released weekly from April 15 through May 13.

Subscribe to follow the series and explore more conversations from the Aspen Institute.