Live! Billy Dees, Sara Alessandrini, and Sam Wooldrik – Iran, Immigration, Epstein & More

This live episode (Mar 19, 2026, 8:00pm EST) of The Billy Dees Podcast brings together host Billy Dees, filmmaker and commentator Sara Alessandrini, and podcaster Sam Wooldrik for a wide-ranging, unscripted discussion that reflects the fast-moving and often chaotic nature of today’s media and political landscape. 

The conversation moves fluidly across major global and domestic issues—including tensions with Iran, immigration policy, and the ongoing intrigue surrounding the Epstein case—while also examining how these topics are shaped, distorted, and amplified by modern media and the podcasting space itself. At its core, the episode explores how public discourse has become increasingly polarized, emotional, and, at times, disconnected from nuance or reality. 

Clip from the Episode

Throughout the discussion, each guest brings a distinct perspective shaped by their background and experience. Alessandrini offers an international lens, emphasizing the complexity of global events and the importance of understanding cultural context, while Wooldrik provides insight into the evolving podcast ecosystem and the challenges of navigating misinformation, sensationalism, and audience expectations.

Billy Dees anchors the conversation with a focus on media responsibility and the need for balanced, thoughtful dialogue. Together, they highlight a central tension of the modern era: the struggle to maintain credibility, reason, and meaningful conversation in an environment increasingly driven by outrage, virality, and competing narratives.

Sara Alessandrini – Problem with Zohran Momdani is Not What He Says, But What He Doesn’t

In this episode of The Billy Dees Podcast, host Billy Dees welcomes returning guest Sara Alessandrini for a wide-ranging discussion that blends media analysis, politics, and cultural perspective. Alessandrini—an accomplished commentator and filmmaker—joins the program to discuss her work and recent writing, including a Substack essay examining the political messaging and policy contradictions surrounding New York City politics. The conversation offers listeners both analysis and context, particularly for those trying to understand the intersection of media narratives and political branding.

Sara Alessandrini

A key focus of the discussion is Alessandrini’s documentary, This Is What New Yorkers Say, a multi-part project that explores the intense media cycle surrounding former New York governor Andrew Cuomo. The series examines how the media helped elevate Cuomo during the early days of the pandemic before later turning sharply critical. Dees and Alessandrini reflect on how this rise-and-fall dynamic mirrors broader trends in modern media, where public figures are often rapidly built up and then dismantled in the public arena.

The conversation then shifts to Alessandrini’s recent Substack article examining the political image and policy messaging of Zohran Mamdani, the current mayor of New York City. Alessandrini argues that the real issue is not necessarily what Mamdani says publicly, but what his messaging leaves unsaid. Together, she and Dees analyze how political branding, campaign promises, and governing realities can diverge—particularly when leaders campaign on ambitious economic proposals while facing complex fiscal realities once in office.

Beyond policy debates, the episode also explores broader themes about ideology, populism, and political movements. Alessandrini explains the role of the Democratic Socialists of America and how grassroots political organizations influence local elections and policy conversations. The discussion highlights how political narratives often evolve through media framing, activist movements, and public perception, shaping how voters understand complex economic and social issues.

Throughout the episode, Alessandrini offers a unique perspective as an immigrant and international observer of American politics. Her reflections on cultural identity, media framing, and political rhetoric provide an additional layer to the conversation, reminding listeners that debates in the United States are often viewed very differently from abroad. The result is a thoughtful and lively exchange that reflects the signature format of The Billy Dees Podcast: informed commentary paired with engaging interviews that challenge audiences to think more critically about politics, media, and the stories that shape public perception.

Billy Dees on X

Sara Alessandrini on X

Sara Alessandrini’s Documentary This is What New Yorkers Say

The Rise of the “Patriot Economy” – Billy Dees Talks Marketing, Politics, and the Psychology of Giving with Jeff Kruszyna

Jeff Kruszyna

On this episode of The Billy Dees Podcast, Billy Dees sits down with Jeff Kruszyna, founder and CEO of JMK Victory, a direct response marketing agency that has helped raise more than $100 million for political campaigns, PACs, veterans’ organizations, and advocacy groups.

The conversation explores the intersection of politics, marketing, and cultural identity in modern America. From the long-term impact of September 11th to the rise of what Kruszyna calls the “patriot economy,” the discussion examines how values-driven consumerism is reshaping business, fundraising, and political campaigns

From 9/11 to a Career in Political Marketing

Jeff Kruszyna’s path into political marketing began with a defining moment in American history.

As an 18-year-old freshman studying computer science at Stony Brook University, Kruszyna was walking across campus when he first heard reports that a plane had struck the World Trade Center. Like many Americans, he rushed to a television and watched events unfold in real time.

That moment changed the trajectory of his life.

Feeling a renewed sense of purpose and patriotism, Kruszyna switched his major from computer science to political science, graduating summa cum laude and Phi Beta Kappa. He soon became involved in the conservative movement and direct response fundraising, eventually building a career helping organizations connect with supporters and donors.

More than two decades later, he has worked extensively with political campaigns and nonprofits focused on issues ranging from veterans’ advocacy to constitutional liberties.

The Emergence of the “Patriot Economy”

One of the central themes of the discussion is Kruszyna’s concept of the “patriot economy.”

According to him, a growing number of Americans are making purchasing decisions based not only on price or convenience—but on shared values and ideological alignment.

Consumers increasingly want to know:

  • What a company stands for
  • Whether its leadership reflects their beliefs
  • Where their money ultimately goes

In recent years, major brands have taken public stances on social and political issues, particularly during the COVID-19 era. In response, many entrepreneurs have launched alternative businesses aimed specifically at consumers who want to support pro-America, pro-freedom, or constitutional values.

The result is a parallel marketplace where products—from coffee to cell phone services—are marketed directly to consumers who want their spending to reflect their political or cultural identity.

A Changing Political Landscape

Billy Dees also raises a broader concern about the current political climate.

In decades past, he notes, political rivals such as Ronald Reagan and Tip O’Neill or Bill Clinton and Newt Gingrich could fiercely disagree while still operating within a shared political framework.

Today, the landscape feels different.

Many Americans now identify strongly with political or cultural “teams,” often consuming information primarily through algorithms that reinforce their existing beliefs. According to Kruszyna, this is both a benefit and a challenge of the digital age.

Social media has made communication easier than ever—but it has also intensified ideological echo chambers.

Despite this polarization, Kruszyna argues that most Americans still share a core sense of national pride and common ground. The challenge for campaigns and organizations is communicating messages that resonate beyond partisan noise.

The Psychology Behind Fundraising

Another major focus of the episode is the psychology of giving.

Kruszyna explains that successful fundraising—whether for political campaigns or nonprofits—comes down to three core elements:

  1. Emotion – People respond to stories that move them.
  2. Identity – Donors want to support causes that align with who they are.
  3. Mission – Clear, compelling goals motivate action.

Direct response marketing, particularly direct mail fundraising, relies heavily on storytelling. A well-crafted fundraising letter often highlights a real person or situation to illustrate the organization’s mission.

The goal is to create a personal connection that encourages the reader to act—whether by signing a petition, joining a campaign, or making a donation.

Why Direct Mail Still Works in the Digital Age

One of the more surprising insights from the conversation is that direct mail remains a powerful fundraising tool, even in the age of social media and digital marketing.

While email and text messaging are inexpensive and immediate, physical mail offers something digital channels often cannot: attention and memorability.

Kruszyna points out that:

  • Email inboxes are crowded and easy to scroll past.
  • A physical letter often stays visible in a home for days.
  • The mailbox today is less competitive than it once was.

Direct mail also blends art and science. Every detail—from envelope color to font choice to postage style—is carefully designed to capture attention within the few seconds someone spends sorting their mail.

The ultimate objective is simple: persuade the recipient to open the letter and engage with the message.

Lessons for Modern Political Campaigns

As the conversation turns toward upcoming election cycles, Kruszyna emphasizes one critical lesson for campaigns:

Start early.

Building a donor base and grassroots support network takes time. Campaigns that delay fundraising efforts often struggle to build the momentum needed for long-term success.

He recommends an omni-channel strategy that includes:

  • Direct mail
  • Email marketing
  • Digital advertising
  • Text messaging
  • Grassroots outreach

Each channel reinforces the others, helping campaigns maintain consistent engagement with supporters.

A Conversation About Politics, Media, and Identity

The interview ultimately becomes more than a discussion about fundraising or marketing tactics.

It is a broader conversation about how identity, politics, and consumer behavior intersect in modern America. As cultural divisions deepen and technology continues to reshape communication, organizations and campaigns must find new ways to connect with audiences who increasingly view the world through ideological lenses.

For Billy Dees, the discussion highlights both the challenges and the opportunities of the current era.

Whether through politics, nonprofit work, or entrepreneurship, the growing emphasis on values-driven engagement is transforming how Americans vote, donate, and spend their money.

Listen to the full episode of The Billy Dees Podcast to hear the complete conversation with Jeff Kruszyna and explore how marketing strategy, political identity, and storytelling are shaping today’s fundraising landscape.

At the Crossroads – Lessons from 2025 and the Uncertain Path to 2026

This episode of The Billy D’s Podcast brings back fan-favorite co-host Cynthia Elliott for a wide-ranging, thought-provoking conversation about where we’ve been—and where we’re headed.

Recorded at the end of a turbulent year, Billy and Cynthia reflect on the unpredictability of 2025 and look ahead to what 2026 may hold. With a mix of realism and cautious optimism, they explore the growing sense of unease many people feel, shaped by nonstop news cycles, cultural shifts, and rapid technological change.

At the heart of the discussion is artificial intelligence—its promise, its risks, and its unavoidable impact on jobs, mental health, and society at large. Cynthia draws on her work as an intuitive and founder of the SoulTech Foundation to unpack how AI could drive medical breakthroughs, reshape the workforce, and accelerate the Fourth Industrial Revolution, while also raising serious concerns about unemployment, regulation, and human purpose. The conversation goes beyond technology, touching on universal income, the mental health crisis, and why emotional intelligence and consciousness must evolve alongside machines if society is going to remain stable.

The episode also dives into broader cultural and geopolitical themes, including energy breakthroughs, the new space race, social media burnout, Hollywood’s declining influence, and the growing divide between toxic online narratives and real-world human connection.

Billy and Cynthia don’t shy away from uncomfortable topics—whether it’s political polarization, gender dynamics, or the erosion of community—but they approach them with candor and depth.

The result is a compelling end-of-year conversation that challenges listeners to think critically about the future, their own awareness, and what it will take to navigate the years ahead.

Andrea LeDew – “Polemics – Political Poems and Prose”

Andrea LeDew

In this episode of The Billy Dees Podcast, Billy welcomes author and poet Andrea LeDew, whose new book Polemics: Political Poems & Prose spans nearly a decade of American political history—from 2016 through early 2025. The conversation explores her creative process, her background in law and literature, and the personal experiences that shape her work.

Andrea explains that Polemics began as a way to process political events that felt unsettling or out of step with the American ideals she grew up with. Each poem in the collection is paired with a short explanation of the real-world event that inspired it, turning the book into both a creative and historical meditation. Her work ranges from sharp satire to somber reflection, and she discusses how humor sometimes helps her strip powerful figures of their mystique, while other moments call for a more serious, even foreboding tone.

Billy and Andrea dive into the long tradition of poets responding to political and historical moments, and Andrea shares examples—such as the James Comey “loyalty” episode and Trump’s “lunatic” tweet—that sparked specific poems. They also explore how her opinions on issues like Confederate statues have changed over time, influenced in part by her travels in Europe and a deeper understanding of how symbols are interpreted by different communities.

Beyond politics, the conversation takes a personal turn as Andrea describes raising a son with autism, navigating special education, homeschooling, and the social challenges families often face. She pushes back against misconceptions—especially the false link between vaccines and autism—and emphasizes how little support exists once children age out of school. Her legal background, she says, has played a role in advocating for her son and understanding the broader structural obstacles families encounter.

Andrea also talks about her lifelong love of rhyme and traditional poetic structure, describing it as both a creative discipline and a way to preserve the musicality of language in an age when memorization is rare. She recently completed the painstaking work of recording her audiobook, an experience Billy relates to from his own broadcasting career.

Throughout the episode, listeners are treated to an insightful, thoughtful exchange about writing, politics, history, disability, and the evolving story of America itself. Andrea’s reflections offer not only context for her book but a reminder of how personal and political narratives intertwine.

Dan Schaefer – Democrat Running in State of Missouri

Dan Schaefer

We often hear that we never have a solid Democrat on the show. Well, we fixed that.

Our guest this episode is Dan Schaefer—a progressive political leader, engineer, and former candidate for the Missouri House of Representatives (District 97). His grassroots campaign focused on restoring reproductive rights, defending public education, and protecting the voice of working people.

Looking ahead to 2026, Dan plans to run again—either for State House District 97 or State Senate District 22. Known as a bold advocate for democratic principles, he has consistently spoken out against authoritarian overreach in state politics and efforts to undermine voter-driven initiatives.

Dan brings a rare blend of practical wisdom, policy expertise, and unwavering commitment to people over power. Whether he’s discussing union rights, economic justice, or civil liberties, he speaks with clarity, conviction, and compassion.

He is also the creator of Frontline Progressive, a newsletter spotlighting threats to democracy and uplifting grassroots action. With over 200 interviews from his past podcasting work, Dan continues to bring substance, energy, and insight to every conversation.

This interview was recorded on August 27, 2025. You can find out more about Dan on his website and Facebook.

You can find the Billy Dees Podcast anywhere podcasts are found. For your convenience a Spotify player is below.

Branding Candidates for 2024 – Do You Like Coke or Pepsi?

In this episode, we dive into the Biden-Trump debate and the RFK Jr. campaign, focusing on the branding and marketing aspects rather than the debate content itself. We contrast Biden’s weaker brand with Trump’s stronger one, underscoring the critical role branding plays in politics.

We also explore the candidacy of RFK Jr. as a new and revitalized contender, highlighting the necessity of a robust brand to captivate voters. RFK Jr. has the opportunity to leverage dissatisfaction with both Biden and Trump to enhance his brand and attract support.

Our discussion emphasizes the importance of branding in politics and the need for candidates to market themselves effectively to voters. Produced in the aftermath of the Biden-Trump debate, this episode examines the implications of branding on political campaigns.

Here is a 2 minute sizzler video. The full episode is available on your favorite podcasting platform and below for your convenience. The video version is also available on Rumble.