Episode 9: From Little League to Big Business: The Rise of Professionalized Youth Sports

Episode 12: Practicing Gratitude: Finding Purpose Through Connection

Welcome, friends.  Today we’re exploring gratitude — not just an emotion, but a mindset, a skill, and a way of seeing the world that can reconnect you to what truly matters.  As we get older, many of us experience a quiet crisis of purpose. The goals that once fueled us lose their spark. Achievements feel less fulfilling. Comparison creeps in. Gratitude offers a way back — not by reinventing yourself, but by remembering yourself. In this episode, I’m joined by my closest friend, Jesse Shafer (from Episode 1), to reflect on my journey through making the podcast fueled by a recent crisis of purpose that pushed me to rethink my life, my goals, and my relationships. With encouragement from a mentor, I set out on a journey that led to ten powerful conversations — many with people I had never met before — spanning seniors, veterans, LGBTQ youth, people with disabilities, public servants, and families navigating homelessness and affordable housing. Along the way, I confronted my own assumptions, felt the weight of others’ lived experiences, and discovered how deeply human connection can expand your understanding of the world. Balancing genuine sentiment with ‘off the cuff’ humor (we can’t resist), Jesse and I look back on: * The impact privilege on gratitude * My struggles with imposter syndrome * The importance of empathy, curiosity, and listening without judgment * The unexpected joy and wisdom found in our own community And to anyone feeling lost or questioning their purpose: practicing gratitude won’t fix everything, but it can change the way you see everything.  You don’t need to be remembered for what you had — but for how you lived and how you made others feel. One day my kids — maybe even my grandkids — will listen to these conversations. I did this to become a better person. To practice curiosity, empathy, and presence. To prove there’s more wisdom in a stranger’s story than in any book. To remind you that being human is messy… but it’s worth it. This podcast isn’t about being important. It’s about being present. Thank you friends for listening. And thank you for being part of this journey.

Episode 11: The Price of Freedom: Life After Military Service

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: * What the VFW is, its 125-year history, and how Post 399 is serving veterans today * The differences between the VFW and the American Legion—and who each organization supports * How veterans’ needs have evolved from World War II to Post-9/11 service members * Mental health, PTSD, and the alarming suicide rate. Why do many veterans stay silent about their service.  * How civilians can move beyond “thank you for your service” to become true allies 💬 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: * LinkTree [https://urldefense.proofpoint.com/v2/url?u=https-3A__linktr.ee_whatdoiknowwithbill&d=DwMFaQ&c=euGZstcaTDllvimEN8b7jXrwqOf-v5A_CdpgnVfiiMM&r=v8DBUQWexqBB6S0MxLAXrxaogeUMNuEVRh3JjFXHTwI&m=J-EeEIejO-YiqH49IgOVm1C8LpIo45LqnPyagEUWO5wvffZeATLLy82Hcp5-5EPJ&s=RqM61sgxbm7M5iOG6scb-yVRUza43O0qbl47d1X51sQ&e=] page with all ways to listen, follow, and subscribe * Follow What Do I Know? on Instagram [https://urldefense.proofpoint.com/v2/url?u=https-3A__www.instagram.com_whatdoiknowwithbill_&d=DwMFaQ&c=euGZstcaTDllvimEN8b7jXrwqOf-v5A_CdpgnVfiiMM&r=v8DBUQWexqBB6S0MxLAXrxaogeUMNuEVRh3JjFXHTwI&m=J-EeEIejO-YiqH49IgOVm1C8LpIo45LqnPyagEUWO5wvffZeATLLy82Hcp5-5EPJ&s=L5d4zlmDC0ok-pHeInq82e8WSR-sg_D2hmjalHLK9jA&e=], Facebook [https://urldefense.proofpoint.com/v2/url?u=https-3A__www.facebook.com_whatdoiknowwithbill2&d=DwMFaQ&c=euGZstcaTDllvimEN8b7jXrwqOf-v5A_CdpgnVfiiMM&r=v8DBUQWexqBB6S0MxLAXrxaogeUMNuEVRh3JjFXHTwI&m=J-EeEIejO-YiqH49IgOVm1C8LpIo45LqnPyagEUWO5wvffZeATLLy82Hcp5-5EPJ&s=Xfa-mUjdOBdYrq576fAflFek1lTy28AHKNjlaYnx6Yk&e=], and TikTok [https://urldefense.proofpoint.com/v2/url?u=https-3A__www.tiktok.com_-40whatdoiknowwithbill&d=DwMFaQ&c=euGZstcaTDllvimEN8b7jXrwqOf-v5A_CdpgnVfiiMM&r=v8DBUQWexqBB6S0MxLAXrxaogeUMNuEVRh3JjFXHTwI&m=J-EeEIejO-YiqH49IgOVm1C8LpIo45LqnPyagEUWO5wvffZeATLLy82Hcp5-5EPJ&s=4J4ns8ArOJjqIlk7pLUxEQn-90m6PiKndeIyhlGDvT8&e=] * Not on social media? Sign up for the bi-weekly newsletter [https://urldefense.proofpoint.com/v2/url?u=https-3A__whatdoiknowwithbill.com_contact_&d=DwMFaQ&c=euGZstcaTDllvimEN8b7jXrwqOf-v5A_CdpgnVfiiMM&r=v8DBUQWexqBB6S0MxLAXrxaogeUMNuEVRh3JjFXHTwI&m=J-EeEIejO-YiqH49IgOVm1C8LpIo45LqnPyagEUWO5wvffZeATLLy82Hcp5-5EPJ&s=REf-W3APDZgMt-ngBjC6mbfmSLPTOCo_UX4ILyYMfvI&e=] for new episodes and recaps * Podcast Website [https://urldefense.proofpoint.com/v2/url?u=http-3A__www.whatdoiknowwithbill.com_&d=DwMFaQ&c=euGZstcaTDllvimEN8b7jXrwqOf-v5A_CdpgnVfiiMM&r=v8DBUQWexqBB6S0MxLAXrxaogeUMNuEVRh3JjFXHTwI&m=J-EeEIejO-YiqH49IgOVm1C8LpIo45LqnPyagEUWO5wvffZeATLLy82Hcp5-5EPJ&s=pJSHluA2EUySIDWr6R7NU5vH0BhLGKe6M6mlOglso0U&e=] to listen, follow, subscribe, and learn about Bill’s story and podcast purpose * YouTube Channel [https://urldefense.proofpoint.com/v2/url?u=https-3A__www.youtube.com_-40whatdoiknowwithbill&d=DwMFaQ&c=euGZstcaTDllvimEN8b7jXrwqOf-v5A_CdpgnVfiiMM&r=v8DBUQWexqBB6S0MxLAXrxaogeUMNuEVRh3JjFXHTwI&m=J-EeEIejO-YiqH49IgOVm1C8LpIo45LqnPyagEUWO5wvffZeATLLy82Hcp5-5EPJ&s=JMUQNeb9nuKxgMrQNMjCEieewbwg3NjHRFVaqrB18oY&e=] with supplemental content

Episode 10: What’s in a Letter? Supporting LGBTQ+ Youth Today

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 * LGBTQ+ 101: Clear distinctions between sexual orientation, gender identity, and how we feel, identify, and express ourselves.  * Personal Stories: Kayla (she/they) shares their journey as a gay, gender-fluid individual and the power of self-definition. * Old Truths, New Terms: Are LGBTQ+ identities truly new—or have they always been part of the human story, only now being recognized and named? * Youth Support: How local programs—from middle school mentorships to high school Pride events—create safe spaces, and the questions around parental notification and group support. * DEI Backlash: Amid rising opposition to diversity and inclusion, how does the LGBTQ+ community remain visible and vocal? 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: * LinkTree page [https://urldefense.proofpoint.com/v2/url?u=https-3A__linktr.ee_whatdoiknowwithbill&d=DwMFaQ&c=euGZstcaTDllvimEN8b7jXrwqOf-v5A_CdpgnVfiiMM&r=v8DBUQWexqBB6S0MxLAXrxaogeUMNuEVRh3JjFXHTwI&m=fBILjbZdHA8AAuqf-bBZHQsB3k5B-liyfNyV-kjfxxTMK4FI2CdSmzbat-ti5gGe&s=hS3gNs_dcTTMEJyA8buB_Jk9mzDnP3Cjv7aR3cIXUkU&e=] with all ways to listen, follow, and subscribe * Follow What Do I Know? on ⁠Instagram⁠ [https://urldefense.proofpoint.com/v2/url?u=https-3A__www.instagram.com_whatdoiknowwithbill_&d=DwMFaQ&c=euGZstcaTDllvimEN8b7jXrwqOf-v5A_CdpgnVfiiMM&r=v8DBUQWexqBB6S0MxLAXrxaogeUMNuEVRh3JjFXHTwI&m=fBILjbZdHA8AAuqf-bBZHQsB3k5B-liyfNyV-kjfxxTMK4FI2CdSmzbat-ti5gGe&s=6fWcrOgHflYZ6t3oVLGAkjU-wNU7dmUh96k7caBtlD4&e=], ⁠Facebook⁠ [https://urldefense.proofpoint.com/v2/url?u=https-3A__www.facebook.com_whatdoiknowwithbill2&d=DwMFaQ&c=euGZstcaTDllvimEN8b7jXrwqOf-v5A_CdpgnVfiiMM&r=v8DBUQWexqBB6S0MxLAXrxaogeUMNuEVRh3JjFXHTwI&m=fBILjbZdHA8AAuqf-bBZHQsB3k5B-liyfNyV-kjfxxTMK4FI2CdSmzbat-ti5gGe&s=nph_BDNmOx4LodoFgrcLvQhzNQRqYD0vHYi14fTD36c&e=], and ⁠TikTok⁠ [https://urldefense.proofpoint.com/v2/url?u=https-3A__www.tiktok.com_-40whatdoiknowwithbill&d=DwMFaQ&c=euGZstcaTDllvimEN8b7jXrwqOf-v5A_CdpgnVfiiMM&r=v8DBUQWexqBB6S0MxLAXrxaogeUMNuEVRh3JjFXHTwI&m=fBILjbZdHA8AAuqf-bBZHQsB3k5B-liyfNyV-kjfxxTMK4FI2CdSmzbat-ti5gGe&s=O6jf6vRzIvyg5vnD7Ri9kshkMuMi5so1vNDhAmmPOk0&e=] * Not on social media? ⁠Sign-up for the bi-weekly newsletter⁠ [https://urldefense.proofpoint.com/v2/url?u=https-3A__whatdoiknowwithbill.com_contact_&d=DwMFaQ&c=euGZstcaTDllvimEN8b7jXrwqOf-v5A_CdpgnVfiiMM&r=v8DBUQWexqBB6S0MxLAXrxaogeUMNuEVRh3JjFXHTwI&m=fBILjbZdHA8AAuqf-bBZHQsB3k5B-liyfNyV-kjfxxTMK4FI2CdSmzbat-ti5gGe&s=CmkM8FJES19wREL5RdF0T2HLjd3U2zsxzrfb1efhAnM&e=] for new episodes and recaps * ⁠Podcast Website⁠ [https://urldefense.proofpoint.com/v2/url?u=http-3A__www.whatdoiknowwithbill.com_&d=DwMFaQ&c=euGZstcaTDllvimEN8b7jXrwqOf-v5A_CdpgnVfiiMM&r=v8DBUQWexqBB6S0MxLAXrxaogeUMNuEVRh3JjFXHTwI&m=fBILjbZdHA8AAuqf-bBZHQsB3k5B-liyfNyV-kjfxxTMK4FI2CdSmzbat-ti5gGe&s=jq78lfFKWy3Ln5axjm2t_MHWJXs9xY2XiEoqJ5_jsXo&e=] listen, follow, subscribe, and learn about Bill’s story and podcast purpose  * YouTube Channel⁠ [https://urldefense.proofpoint.com/v2/url?u=https-3A__www.youtube.com_-40whatdoiknowwithbill&d=DwMFaQ&c=euGZstcaTDllvimEN8b7jXrwqOf-v5A_CdpgnVfiiMM&r=v8DBUQWexqBB6S0MxLAXrxaogeUMNuEVRh3JjFXHTwI&m=fBILjbZdHA8AAuqf-bBZHQsB3k5B-liyfNyV-kjfxxTMK4FI2CdSmzbat-ti5gGe&s=0vp2RbrNv0Zoi7DEOMchNphyVZuTJzRcI3t9Kd_0uvA&e=] with supplemental content

Episode 9: From Little League to Big Business: The Rise of Professionalized Youth Sports

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: * How youth sports have evolved since the 1990s—from local leagues to national travel teams and tech-enhanced performance training * The role of AI, social media, and structured investment in shaping young athletes' experiences and outcomes * How the business of youth sports is creating both opportunity and pressure for families across the country * Where youth sports may be headed by 2030, including equity, access, and new models of leadership * LeagueApps’ work with underserved communities and the launch of NextUp—a professional platform for the youth sports industry ⚾ 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: * LinkTree page [https://urldefense.proofpoint.com/v2/url?u=https-3A__linktr.ee_whatdoiknowwithbill&d=DwMFaQ&c=euGZstcaTDllvimEN8b7jXrwqOf-v5A_CdpgnVfiiMM&r=v8DBUQWexqBB6S0MxLAXrxaogeUMNuEVRh3JjFXHTwI&m=TJrdCoSJDZEpGmQ1Bj_IYwbinXFw4bm87bwX5tvg2euMxj6Q_woCB_kXOsfm1Sb4&s=GS7cMAC-nAwbBlEDMhi9fjEXtSBoOablU58kX_eYfJg&e=] with all ways to listen, follow, and subscribe * Follow What Do I Know? on ⁠Instagram⁠ [https://urldefense.proofpoint.com/v2/url?u=https-3A__www.instagram.com_whatdoiknowwithbill_&d=DwMFaQ&c=euGZstcaTDllvimEN8b7jXrwqOf-v5A_CdpgnVfiiMM&r=v8DBUQWexqBB6S0MxLAXrxaogeUMNuEVRh3JjFXHTwI&m=TJrdCoSJDZEpGmQ1Bj_IYwbinXFw4bm87bwX5tvg2euMxj6Q_woCB_kXOsfm1Sb4&s=MPFLrNR9XD-3Edh3adcfRVSBiFeQcc2hcV1PY5VeVEg&e=], ⁠Facebook⁠ [https://urldefense.proofpoint.com/v2/url?u=https-3A__www.facebook.com_whatdoiknowwithbill2&d=DwMFaQ&c=euGZstcaTDllvimEN8b7jXrwqOf-v5A_CdpgnVfiiMM&r=v8DBUQWexqBB6S0MxLAXrxaogeUMNuEVRh3JjFXHTwI&m=TJrdCoSJDZEpGmQ1Bj_IYwbinXFw4bm87bwX5tvg2euMxj6Q_woCB_kXOsfm1Sb4&s=3nnRcHU0_iBfHUbz2gTc29Py8nU39snOHDOMpg5URzw&e=], and ⁠TikTok⁠ [https://urldefense.proofpoint.com/v2/url?u=https-3A__www.tiktok.com_-40whatdoiknowwithbill&d=DwMFaQ&c=euGZstcaTDllvimEN8b7jXrwqOf-v5A_CdpgnVfiiMM&r=v8DBUQWexqBB6S0MxLAXrxaogeUMNuEVRh3JjFXHTwI&m=TJrdCoSJDZEpGmQ1Bj_IYwbinXFw4bm87bwX5tvg2euMxj6Q_woCB_kXOsfm1Sb4&s=f-rYNPDW5X8BYBWthd9H1DYPicOwfQ1XK-Lm4WFCVYU&e=] * Not on social media? ⁠Sign-up for the bi-weekly newsletter⁠ [https://urldefense.proofpoint.com/v2/url?u=https-3A__whatdoiknowwithbill.com_contact_&d=DwMFaQ&c=euGZstcaTDllvimEN8b7jXrwqOf-v5A_CdpgnVfiiMM&r=v8DBUQWexqBB6S0MxLAXrxaogeUMNuEVRh3JjFXHTwI&m=TJrdCoSJDZEpGmQ1Bj_IYwbinXFw4bm87bwX5tvg2euMxj6Q_woCB_kXOsfm1Sb4&s=zkieYLnAZO4oeMZ7bRaBsg5wZrASye1mRAVGqPAI9II&e=] for new episodes and recaps * ⁠Podcast Website⁠ [https://urldefense.proofpoint.com/v2/url?u=http-3A__www.whatdoiknowwithbill.com_&d=DwMFaQ&c=euGZstcaTDllvimEN8b7jXrwqOf-v5A_CdpgnVfiiMM&r=v8DBUQWexqBB6S0MxLAXrxaogeUMNuEVRh3JjFXHTwI&m=TJrdCoSJDZEpGmQ1Bj_IYwbinXFw4bm87bwX5tvg2euMxj6Q_woCB_kXOsfm1Sb4&s=Z0WdORHDtW1LtQIDPdDZrWeiMPqzCb5t7k8pB5NcNDw&e=] listen, follow, subscribe, and learn about Bill’s story and podcast purpose  * ⁠YouTube Channel⁠ [https://urldefense.proofpoint.com/v2/url?u=https-3A__www.youtube.com_-40whatdoiknowwithbill&d=DwMFaQ&c=euGZstcaTDllvimEN8b7jXrwqOf-v5A_CdpgnVfiiMM&r=v8DBUQWexqBB6S0MxLAXrxaogeUMNuEVRh3JjFXHTwI&m=TJrdCoSJDZEpGmQ1Bj_IYwbinXFw4bm87bwX5tvg2euMxj6Q_woCB_kXOsfm1Sb4&s=abYU4VNgzc6fkAWrf0gs-S0TLVjXVmiDSeSMT_p39hs&e=] with supplemental content

Episode 8: The Wisdom in the Room — Honoring Our Senior Citizens

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: * What the Westport Senior Center is and how it serves as a dynamic, welcoming space for older adults * Personal reflections on volunteering, and the unexpected energy and joy found at the WCSA * Insightful and moving testimonials from members, including veterans, artists, former nurses.  * Stories that span Broadway stages, Wall Street battles, and life-changing relocations late in life * A heartfelt conversation with Wendy about generational empathy and the profound impact seniors have on families and communities