Sixteen million Americans—about 6% of the U.S. population—carry the title of veteran. They live quietly among us, yet their acts of sacrifice, resilience, and patriotism have shaped our freedoms in ways most of us will never fully grasp. We honor them with parades, ceremonies, and endless “thank yous.” But what happens when the bands stop playing?
In this episode of What Do I Know?, we look beyond the public salutes to explore what life after service really looks like for veterans. Many face challenges that extend far beyond their time in uniform—mental health struggles, housing insecurity, substance abuse, and the physical and emotional toll of combat. Joining me is Navy veteran Phil Delgado, headmaster of Westport’s Veterans of Foreign Wars Post 399. Together, we’ll unpack the VFW’s mission, the evolving needs of veterans across generations, and how organizations like Post 399 are adapting to support those returning from recent conflicts. From the camaraderie of the VFW hall to the quiet battles fought in everyday life, Phil shares a candid look at what it means to serve, transition, and keep moving forward.
💡 Inside the Episode:
💬 Why This Conversation Matters:
Our freedoms—speech, press, bear arms, religion, protest, privacy—aren’t guaranteed everywhere in the world. Veterans have defended them for decades, often at great personal cost. This episode challenges all of us to think about what comes after the parade, and how we can show up for the people who showed up for us.
Stay Connected:
In this episode, we open the door to a deeper understanding of the LGBTQ+ community — one that has existed across every culture and era yet continues to evolve in visibility and vocabulary. As the world celebrates WorldPride 2025 in Washington, D.C., we zoom in on the people and stories shaping change right here in our hometown. My guest, Kayla Ionetta — an educator, self-advocate, and chair of the Westport Public Schools Pride Coalition (a Gay Straight Alliance or GSA) — joins the podcast to explore identity, understanding, and how we support LGBTQ+ youth in a shifting political landscape.
Listen as GenX (me) talks to a Millennial member of the LGBTQ+ community (Kayla) about GenZ LGBTQ youth today. A delightful and enriching conversation.
What You’ll Learn
Why This Episode Matters
Identity is not a debate—it’s a part of being human. This episode cuts through the noise with a candid, compassionate dialogue across generations and identities. Whether you’re a parent, educator, ally, or just curious, this episode challenges assumptions, humanizes complex issues, and reminds us that every young person deserves the freedom to be seen, supported, and safe.
Stay Connected:
Over the past three decades, youth sports in America have undergone a massive transformation. What was once a casual, community-based activity is now increasingly shaped by professional-level infrastructure, technology, and investment. In this episode, we explore how parents, coaches, and communities can navigate this evolution to support kids in the healthiest, most meaningful way possible. Our guest, Jeremy Goldberg, President of LeagueApps, and a parent-coach himself, brings unmatched insight from the intersection of sports, technology, investment and youth development.
🎯 In This Episode, We Cover:
⚾ Why This Conversation Matters:
Youth sports now impact everything from family schedules to college admissions, shaping not only kids’ athletic skills but also their confidence, identity, and social worlds. Understanding this fast-moving shift isn’t just important for parents and coaches—it’s essential for anyone who cares about equity, community, and the future of play.
Stay Connected:
Today we shine a light on a group of people whose lives have spanned nearly a century of extraordinary change—our senior citizens. From the moon landing to smartphones, world wars to civil rights, their lived experiences offer not just history, but wisdom, humor, humility, and heart. Joining us to help celebrate this remarkable generation is Wendy Petty, Director of the Westport Center for Senior Activities (WCSA), a vibrant community hub that’s redefining what it means to grow older with purpose, passion, and connection.
👟 In This Episode, We Cover:
In this enlightening episode, we sit down with James Ross, Chair of the Westport Commission on People with Disabilities, and Elaine Daignault, Director of Westport Human Services, to explore what it truly means to see the person before the disability. Through stories, community insight, and cultural reflections, we uncover how embracing diverse abilities not only enhances individual lives but enriches our community.
💡 Inside the Episode:
🧭 Why This Episode Matters:
This episode challenges listeners to rethink what’s “normal” by focusing on the humanity, talents, and rights of people with disabilities. When we pause to truly see the person — not just the diagnosis — we create a more inclusive, empathetic, and a perspective on who we are as people first. Whether you're a policymaker, employer, parent, or neighbor, this conversation offers meaningful ways to connect, support, and uplift.
Media resources from this episode:
Stay Connected:
What does homelessness look like in an affluent suburb like Westport—and who truly gets to call it home?
In this deeply human episode, we go beyond the stereotypes to explore the hidden faces of housing insecurity in one of America’s wealthiest towns. At the heart of this story is Homes with Hope, a local nonprofit quietly rewriting the narrative on homelessness since 1984. From emergency shelter to affordable housing and wraparound services, they’ve been helping people not just survive—but rebuild their lives with dignity.
Featuring three thoughtful and inspiring guests, one of which lives in affordable housing in Westport.
💡 Inside the Episode:
🌱 Communities vs. Castles:
We close with a heartfelt reflection on what makes a town feel like a true community. Why should the people who care for our children, serve our meals, and heal our wounds be able to live where they work? And how can we build towns that don’t just welcome—but truly include?
💬 Why This Episode Matters:
This episode is a powerful reminder: a stronger, kinder community is one that makes room for everyone. Westport is setting a high bar leading by example.
Stay Connected:
This episode is raw, fearless, and deeply moving. Host Bill Shakos sits down with Connecticut State Senator Ceci Maher for an unflinching conversation about mental health, addiction, and the heavy burden of stigma. Through powerful personal stories—especially those that hit painfully close to home—Ceci shares how her life was forever shaped by love, loss, and the quiet battles many face in silence.
In this episode, Ceci opens up about her late husband’s 15-year struggle with alcoholism, stemming from PTSD after being on-site during the September 11th attacks. She reveals the heartbreaking toll it took on their marriage, how addiction almost tore them apart—and how she ultimately lost the man she still calls her best friend. But this is also a story of resilience. Of replacing shame with compassion. Of turning pain into purpose.
Together, we shed light on the often-hidden realities of mental health and addiction, challenge the narratives shaped by judgment, and explore what it truly means to show up for those we love.
💡 What You’ll Hear:
💬 Why This Episode Matters:
Mental health affects 1 in 5 American adults—yet stigma still keeps millions from seeking help. This episode is a call to listen without judgment, speak with compassion, and recognize that behind every struggle is a human being worthy of dignity, support, and love.
Stay Connected:
What difference can one person make?
In the case of Westport, Connecticut, one person’s vision and dedication have shaped the town's culture and identity for over five decades. That person is Dan Woog, a man whose life's work has been a legacy of advocacy, storytelling, and community-building—transforming Westport into what it is today.
In this compelling episode of What Do I Know?, host Bill Shakos sits down with Dan, who has spent over 55 years as a student, journalist, soccer coach, author, and community advocate. Together, they explore Dan’s journey from a young writer to a pioneering force in Westport’s social fabric.
In This Episode:
A Lifelong Calling to Write: From his first column in high school to his bylines at the Westport News and the publication of 17 books, Dan shares how writing became a channel for documenting and influencing Westport’s evolution.
Building a Digital Legacy: For 15 years, Dan has run 06880 Where Westport Meets the World, a nonprofit blog that’s become a central hub for community stories, featuring over 18,000 articles and 100+ video podcasts.
Championing LGBTQ+ Advocacy: As a trailblazer for Gay-Straight Alliances (GSAs) in Connecticut, Dan reflects on his groundbreaking work in 1993, when he founded the first GSA in the state while also coming out as gay. His advocacy continues in his books and research on the intersection of sexuality, school life, and sports.
Time Machines & Messages in Bottles: With a focus on paying it forward, Dan shares insights into what advice he’d give his younger self—and what guidance he would offer the Westport of 2050.
Stay Connected:
Why Local Government Matters & How to Get Involved
In this inspiring episode of What Do I Know?, host Bill Shakos interviews David Rosenwaks, a recent Westport resident who ran and was elected to local government position after noticing minimal representation of parents. They explore the power of local government and why getting involved can make a real difference.
In This Episode:
Why Listen?
This episode is a reminder that local government directly impacts your daily life — and anyone can get involved to make a difference.
Stay Connected:
A Candid Conversation About Racism in Suburbia
In this powerful episode of What Do I Know? host Bill Shakos speaks with Richard Anderson, a Black resident of Westport, about his family’s experiences with racism in the community. The Andersons repeatedly encounter racially motivated roadblocks. Together, Bill and Richard explore the complexities of race, privilege, and friendship in suburban neighborhoods.
In This Episode:
Why Listen?
This episode is an honest look at the reality of racism in suburban America, balanced with moments of levity and genuine friendship. It challenges listeners to reflect on the idea that having bias, whether by nature or nurture, it is what you make of it.
Stay Connected
Host Bill Shakos reflects on turning 50 and navigating life after the pandemic in the pilot episode of What Do I Know?. Joined by his friend of 30 years, Jesse Shafer, they explore what the “new normal after COVID” means for them. One made good choices, the other went down a rabbit hole of escapism.
In This Episode:
Why Listen? A candid conversation on escapism vs. balance and breaking bad habits. This episode dives deep into reflection, change, and the pursuit of balance in a post-pandemic world. If you’ve ever felt the need to reset or reconnect, this conversation is for you.
Stay Connected:
