Pops and Son Conversations
Join US Air Force Veteran, Presidential Achievement Award Recipient, author, philanthropist, and social media influencer, Rob Malloy, and his son, author and model, Javan Anderson, as they navigate the generation gap with humor and heart. On this podcast, Rob and Javan tackle a wide range of topics – from life lessons and fatherhood to current events and pop culture – offering a unique blend of old-school wisdom and new-school perspectives. Expect lively debates, unexpected insights, and plenty of laughs along the way. Tune in to Pops and Son Conversations and discover: Candid conversations: Rob and Javan share their honest thoughts and experiences, providing a refreshing take on intergenerational relationships. Diverse perspectives: Hear how Rob's traditional values intersect with Javan's modern outlook, creating dynamic and engaging discussions. Humor and heart: Enjoy a show that's both entertaining and thought-provoking, leaving you with a smile and something to ponder. Subscribe now and join the conversation!
Episodes
December can turn a light vibe into a high‑stakes situation fast. We dive into the real dynamics of dating during the holidays—why the season pushes labels, how gift pressure skews judgment, and where family and office invites send signals you might not intend. From Pops’ mission-first “Santa season” schedule to Javen’s parent-first priorities, we map out sane boundaries you can borrow to keep your joy, your budget, a...
The holidays can feel like a high-wire act: keep the magic alive for the kids, honor family traditions, and somehow protect January from December’s receipts. We open our hearts about the pressure fathers carry this time of year and share the practical ways we stay grounded—so joy wins and debt doesn’t.
We talk about the early hit of Black Friday, the second budget that sneaks in for Christmas, and how easy it...
The best memories don’t come from perfect pies; they come from people who feel seen. We take a fresh run at Thanksgiving by reframing it as Family Day—an open door for those who love the gathering but not the old narrative. That small shift brings big wins: earlier meals so no one is hangry by 4 pm, gratitude circles that ground the room, and traditions that respect elders while giving kids a clear rite of passage fro...
Please follow Pops and Son Conversations on the website, popsandsonconversations.com, and social media @popsandsonconversations
Ever thank a living veteran on Memorial Day? We start by drawing a bright line between honoring the fallen and celebrating those still with us, then dive into what service really looks like beyond the holiday hashtags. From PTSD that ripples through families to the slow grind of the VA system, we keep it frank, respectful, and practical—because respect without access isn’t enough.
We swap stories across gener...
Politics can feel like noise until you realize the decisions shaping your block are made in rooms most of us never enter. We pull that door open and walk through what really moves change: local elections, the roles nobody explains, and the everyday actions that turn your vote into visible results on your street.
We start by naming the discomfort around politics in Black communities and where it comes from—his...
Dating shouldn’t feel like guesswork, and reinvention doesn’t have to feel like failure. We unpack what it means to date with purpose beyond the usual destination of marriage—healing, confidence, and clarity count too—and why friendship first is the underrated foundation for honest love. You’ll hear how skipping the friendship stage fuels situationships, how to run progress checks in a relationship without turning it ...
What does balance really look like when life gets loud? We open October with birthdays, family energy, and a grounded nod to awareness month causes, then get honest about what 31 and 50 have taught us about growth, legacy, and being present. Jay frames his early 30s as a rediscovery—testing old beliefs, owning creativity as a public craft, and building a father’s toolkit that goes beyond money into mindset and resilie...
The world doesn't pause at the halfway mark of your journey. Goals don't care that we're only in July. But perhaps we should—because that mid-year checkpoint might be exactly what we need to realign, refocus, and rediscover our purpose.
In this reflective solo episode, I take you through the importance of mid-year check-ins and why pausing to acknowledge both your progress and your process matt...
What happens when we disconnect from our family roots and lose the multi-generational wisdom that once flowed naturally through our households? In this heartfelt exploration of family dynamics, Rob "Sylvan Fox" Malloy and Javan "Check Three Times" dive deep into what it truly means to build a home that nurtures both individuals and communities.
The conversation begins with a provocative co...
The struggle for voting rights in America forms the backbone of our democracy, yet many of us fail to exercise this hard-won privilege. In this eye-opening conversation, Rob and Jay examine why voting matters far beyond simply checking a box every four years.
Have you ever noticed how affluent neighborhoods proudly display political yard signs while other communities keep their political leanings hidden? This...
Freedom delayed is not freedom denied. This powerful truth lies at the heart of Juneteenth, a holiday that only recently gained federal recognition but carries centuries of profound significance for Black Americans and our shared national story.
On this special solo episode, I dive deep into the complex history of Juneteenth, tracing its origins to that momentous day in 1865 when Union General Gordon Granger ...
Ever felt like you're supposed to have it all figured out but secretly you're drowning in doubt and uncertainty? You're not alone.
In this raw, unfiltered solo episode, Rob "Pops" Malloy steps up to deliver a message straight from the heart to men everywhere who are silently struggling. With his son taking the day off, Rob seizes this moment during Men's Health Awareness Month t...
What happens when you put health on the backburner? As Rob "Silver Fox" Malloy eloquently puts it: "If you don't make time for your body, your body will make time." This powerful statement anchors our Men's Health Awareness Month conversation, where we dive into the critical yet often overlooked aspects of male wellness.
Remember when you could eat a whole pizza, wake up the next...
Brotherhood forms the cornerstone of men's health, extending far beyond biological relationships. During this Men's Health Month special episode, we explore what true brotherhood means - those relationships where accountability, vulnerability, and unwavering support create bonds sometimes stronger than blood.
We share personal stories of our earliest brotherhood connections, from elementary school f...
We explore mental health within family dynamics, examining how emotional processing, boundary setting, and generational patterns affect our wellbeing.
• Growing up without guidance on processing emotions leaves many of us ill-equipped to handle feelings
• Many families, especially in communities of color, prioritized survival over emotional health
• The "strong one" in every family often bea...
What happens when mental health challenges intersect with romantic relationships? In this candid conversation, Rob and Javan explore the delicate balance between vulnerability and self-protection when dating while managing mental health concerns.
The father-son duo tackles one of the most challenging relationship questions: how much of your mental health history should you share with a new partner, and when s...
Rob and Javan Malloy dedicate this special episode to celebrating mothers and exploring the intricate dynamics of mother-son relationships, examining how these foundational bonds shape men's identities and emotional development.
• Discussion about reclaiming the term "mama's boy" from its negative connotation
• Exploring how mothers teach sons to receive and give love
• Examining h...
Breaking the silence around mental health starts with honesty. How often do we respond with "I'm blessed" when someone asks how we're doing, even while struggling inside? This automatic deflection prevents authentic connection and leaves many suffering alone behind carefully constructed facades.
During Mental Health Awareness Month, we're tackling the persistent stigma surrounding men...
Ready to break free from living paycheck to paycheck? Financial literacy isn't just about understanding money—it's about taking action to improve your financial situation through multiple income streams.
During Financial Literacy Month, we're diving deep into three powerful strategies that can transform your financial future: investing, creating merchandise, and developing digital products. The...
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