The Culture Matters Podcast

Jay Doran
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Jan 17, 2026 • 51min

Season 89, Episode 1064: 2025 NYE Lollapalooza NYE Lollapalooza Episode 17: The Opportunity Is Still Here

Episode 17 closes out the NYE Lollapalooza with a conversation that feels like a final reset before the calendar turns — not just on goals, but on identity, leadership, and what actually drives people to change.Jay Doran is joined by Jenna Silverman, Bill Reiman, Glenn Llopis, and Mark Perkins for a New Year’s Eve roundtable on the words that shaped 2025 and the words they’re carrying into 2026.Jay shares his evolution from last year’s theme — “life can only be understood backwards, but must be lived forwards”— into a deeper truth: life isn’t a problem to solve, it’s a reality to experience. His word shifts from intensity to love, setting the tone for a conversation that’s both grounded and honest.From there, the room opens up:Jenna reflects on her shift from faith into surrender — and why surrender isn’t weakness, it’s alignment.Bill shares that his word for 2026 is faith, and talks through what it looks like to shut out noise, stop letting fear lead, and build life and business from a deeper foundation.Glenn brings the edge with a powerful framework: reinvention (2025) → conviction (2026). He challenges the idea that success is the same as health, and unpacks why so many leaders are exhausted — not from hard work, but from performing instead of truly executing as themselves.Mark anchors the conversation with a simple but relentless word: go — the compounding power of doing business the right way for years, staying decisive without perfect certainty, and continuing to move even when plans break.The group digs into the tension leaders feel every day: how to see potential clearly, how to lead people without carrying them, and how to commit to growth without sacrificing the things that actually matter.This one is a strong finish to the Lollapalooza: deep, real, and full of practical truth you can carry into 2026.If this episode hit home, share it with someone who needs it — and leave a review so we can keep reinvesting back into you.
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Jan 16, 2026 • 56min

Season 89, Episode 1063: 2025 NYE Lollapalooza Episode 16: Perspective, Strength, and Faith

Episode 16 of the NYE Lollapalooza is one of the most grounded, emotional, and necessary conversations of the entire day.Jay Doran is joined by Jenna Silverman, Bill Reiman, Jonathon Haddad, and Joe Silva for a raw discussion on the words that shaped 2025—and the ones guiding 2026.What begins as a simple reflection on annual themes quickly evolves into something deeper: fatherhood, responsibility, faith, emotional regulation, and perspective. The group wrestles with what it truly means to lead—not just businesses, but families, communities, and themselves.You’ll hear:Why consistency without faith lacks purposeHow strength becomes a blessing when responsibility is embracedWhy balance is not 50/50—but situational awarenessHow perspective is forged through sacrifice, time, and choiceWhat it means to raise children in a world that often avoids discipline, honor, and accountabilityThe conversation moves through personal stories of parenting, marriage, mental health, addiction, recovery, leadership pressure, and cultural erosion—without posturing or performance. It’s honest. It’s emotional. And at times, it’s heavy in the best way.A standout moment includes a reading of Rudyard Kipling’s If, used as a lens to discuss masculinity, discipline, and the responsibility to protect—not dominate—the village.This episode isn’t about resolutions.It’s about choices.It’s about keeping the main thing the main thing.And it’s about understanding that life doesn’t give perspective gently—it teaches it through experience.If you’re stepping into 2026 as a leader, a parent, or someone trying to become steadier in a chaotic world—this conversation will stay with you.🎧 Listen closely. Share what resonates. And if it moved you, leave a review—because that’s how this work continues.
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Jan 15, 2026 • 54min

Season 89, Episode 1062: 2025 NYE Lollapalooza Episode 15: High Stakes, Clear Objectives

Episode 15 is a different kind of New Year’s Eve conversation—less “resolution energy,” more real life, real leadership, real presence.Jay Doran and Jenna Silverman sit down with Michael Allosso and Joseph Iredell during the 2025 Lollapalooza to unpack the theme:“Life is not a problem to be solved, but a reality to be experienced.”From the jump, it’s personal—Mike Calhoun has officially tapped out after an all-day hosting marathon, and Jenna steps in to co-lead the room. What follows is a layered discussion about the words that shaped 2025 and the words driving 2026:Michael Allosso (2025): Seen & Heard — the ache of invisibility, and the power of making people feel visible.Michael (2026): Intensity — no more passive interactions; every moment becomes an event, with real stakes.Joseph Iredell: moves from Understanding into Dominance for 2026—less introspection, more execution, and refusing to “play defense” after momentum is built.Jenna: reflects on Faith in 2025 and anchors 2026 in Surrender—letting go of forced outcomes while staying disciplined about clarity, communication, and aligned action.The episode also hits a few Culture Matters gold veins: casting vs. hiring, why leaders misplace people into roles that drain them, and why “stakes” change everything—your tone, your preparation, your presence, and the way people remember you.They close by wrestling with a big question: How do you teach values in a way that’s engaging—lived, not lectured?The answer keeps circling back to the same truth: values become real when they show up inside conversations, decisions, and the way we treat people when no one’s watching.If you’re heading into 2026 craving more presence, more purpose, and fewer forced outcomes—this one will land.
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Jan 14, 2026 • 59min

Season 89, Episode: 1061: 2025 NYE Lollapalooza Episode 14: Choices Create Outcomes

Episode 14 of the New Year’s Eve Lollapalooza gets loud—in the best way.Jay Doran and co-host Mike Calhoun are joined by Brad Lea, Jenna Silverman, Anthony Mirarchi, Benny Fisher, and Fobby Naghmi for a rapid-fire, high-trust conversation about the words that will define 2026—and the decisions that will shape everything that follows.The theme that keeps surfacing: you don’t change your life by wanting it… you change your life by choosing it.Here’s what each guest is carrying into 2026:Jay: Love (after Intensity) — bringing people together, leading with courage, and reclaiming parts of himself he shelved along the way.Jenna: Surrender (after Faith) — releasing forced outcomes, tightening clarity and communication, and building Culture Matters with alignment and trust.Benny: Stewardship — honoring what he’s already been entrusted with, shifting from builder to caretaker, and going deeper with fewer relationships.Fobby: Certainty — and the story behind it: how one question from Brad unlocked a decade of weight and redirected his trajectory.Anthony: Enriched / Enriching — getting uncomfortable again, creating new products in commercial insurance, and thinking roll-ups, M&A, and bigger plays.Brad: starts with Unrecognizable… then evolves it into Choice — because free will is the overlooked superpower and better decisions compound into better lives.There are also practical gems throughout: create and publish daily, don’t “make the content content,” stop negotiating with fear, and build real momentum through consistent revenue-generating action.If you’re stepping into 2026 hungry for a reset—this episode is a jolt of clarity. Share it with someone who needs to hear it, and leave a review for The Culture Matters Podcast so we can keep building this the easy way.
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Jan 13, 2026 • 47min

Season 89, Episode 1060: 2025 NYE Lollapalooza Episode 13: Faith Over Control

Episode 13 of the New Year’s Eve Lollapalooza is one of the most personal—and most powerful—conversations of the day.Jay Doran and co-host Mike Calhoun are joined by Jenna Silverman, Tom Bove, Hector Sanchez, Glenn Campbell, and David Yerkes for a roundtable on the words shaping their year, the lessons they’re carrying forward, and what it really looks like to grow without gripping life so tightly.The words set the tone immediately:Jenna: Surrender (after last year’s Faith) — letting go of forced outcomes and building Culture Matters with trust, clarity, and alignment.David Yerkes: Breakthrough (after Perseverance) — after a remarkable final quarter of 2025, stepping into a new season with momentum already in motion.Hector: Momentum (after Foundation) — building something real and now pressing forward through leadership and operational consulting.Tom: Investing — investing in himself, his relationships, and presence after a year that tested him deeply.Glenn: Listening — learning to listen to understand, not to fix; becoming the kind of man people feel safe with.From there, Jay shares the heart behind why believes “love” requires risk—bringing the right people together, even when the instinct is to protect by keeping distance. Mike closes with his word, Different, and challenges everyone heading into 2026 to stop repeating what worked before and start evolving on purpose.You’ll also hear quick snapshots of what each guest is building—leadership consulting, a growing e-commerce headwear company, technology consulting, and longevity/performance medicine—and how faith, discipline, and daily action are the throughline.If you’re stepping into 2026 needing a reset in mindset, relationships, or leadership—this episode is for you. Share it with someone you care about, and leave a review on The Culture Matters Podcast to help us keep growing these conversations.
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Jan 12, 2026 • 55min

Season 89, Episode 1059: 2025 NYE Lollapalooza Episode 12: Do It Different This Time

Episode 12 of the New Year’s Eve Lollapalooza is a masterclass in what actually scales: preparation, consistency, and focus — with zero fluff.Jay Doran and co-host Mike Calhoun are joined by Armand Pinoci, Aaron Scott Young, Michele Schina, Nick Lampone, Yuri Mitchell, and Nathan Knottingham for a fast-moving roundtable on their words for 2026, the lessons they’re taking from 2025, and the real priorities that will shape the year ahead.The words set the tone:Nathan: Preparedness (after last year’s Flexibility) — staying ready for the known and unknown without losing peace.Nick: Reputation — because “it’s not what people shout, it’s what they whisper,” and in finance, trust is everything.Michele: Mastery — sharpening the fundamentals, becoming a better leader, coach, and teacher through the numbers.Aaron: Momentum — shedding the distractions, doubling down on what’s boring, profitable, and scalable.Yuri: Consistency — building structure at home and at work, especially with a new baby and new responsibilities.Armand: Stability — year seven in business, a new house, and the commitment to keep the foundation strong.Mike: Different — because growth requires a new approach, not just more effort.From there, the conversation turns into pure value: how to scale by staying in your lane, why “rejection is protection,” what consistency looks like over six years of showing up, and why patience is often the hidden ingredient behind real stability.If you’re heading into 2026 wanting a clearer focus and a stronger foundation — this is your episode. Share it with someone building something real, and leave a review on The Culture Matters Podcast to help us keep elevating these conversations.
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Jan 11, 2026 • 51min

Season 89, Episode 1058: 2025 NYE Lollapalooza Episode 11: Second Half Adjustments

Episode 11 of the New Year’s Eve Lollapalooza is a brotherhood conversation — the kind that doesn’t posture, doesn’t perform, and doesn’t pretend.Jay Doran and co-host Mike Calhoun are joined by Eddy Perez Jr., Brett Grossman, John New, and Darwin Roman to talk words for 2026, the cost of leadership, and what it really looks like to keep showing up when life gets heavy.The words on the table set the tone fast:Darwin: Value — not just what you bring to others, but what you require for yourself (boundaries included).Eddy: Atonement — owning the moments you knew better and didn’t listen to yourself.Brett: Self-Actualization — becoming the man you’re capable of being, day by day.Mike: Different (and last year: Jubilee) — reset, rethink, and stop doing what no longer serves the mission.Jay: last year Intensity, this year Love — life isn’t a problem to solve, it’s a reality to experience.From there, the conversation turns real: building your “team” in relationships (assets vs. liabilities), why men often don’t make the call when they’re struggling, the pressure of being the one who always “handles it,” and the second-half adjustments that actually win championships — in business, fatherhood, and life.John New shares a powerful win: getting through years of divorce dynamics and choosing to “win with love” for his kids. Eddy opens up about identity, leadership, and why atonement starts with accountability. Brett talks honestly about weathering a financial storm and the quiet danger of carrying everything alone. Darwin brings it home with the hard lesson: if you don’t respect your own value, you’ll pay for it.If you’re a man carrying pressure in silence — or you love someone who is — share this episode with a brother.
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Jan 10, 2026 • 49min

Season 89, Episode 1057: 2025 NYE Lollapalooza Episode 10: Lead with Amity, Move Expeditiously

Episode 10 of the New Year’s Eve Lollapalooza feels like a collective “second wind” — the kind you get when a conversation becomes less about performance and more about presence.Jay Doran and co-host Mike Calhoun are joined by Morgan DeNicola, Ruth Lee, David Levine, and John Duffin for a deeply human dialogue centered on the words each person is carrying into 2026:Morgan: LeadershipRuth: Amity (agreement without avoidance — the ability to stay clear without becoming hard)David: Coherent (alignment, resonance, and living in a way that matches what you say you value)John: Expeditious (speed + urgency — refusing to squander the moment)John opens with urgency and intentional thinking — including the decision to step away from social media when it’s engineered for outrage instead of clarity. Ruth expands the room with Amity, reframing “agreement” as a skill: holding strong views without needing to fight, and moving from reaction to choice in high-stakes environments.Morgan shares how a year of pivoting turned into a clearer call to step fully into leadership — not from ego, but from responsibility. And David brings the future into the present: after decades as a technology entrepreneur, he’s preparing to launch an AI-driven platform designed to make wisdom more accessible — capturing the “blueprints” of mentors, coaches, and leaders so more people can benefit between live sessions and high-ticket containers. (Launch shared in the conversation: February 20, at Conscious Life Expo in LA.)This episode is a reminder that the next year doesn’t need a thousand goals. Sometimes it needs one word that tells the truth.If someone in your life feels scattered, reactive, or stuck — share this episode. And if this conversation sparked something in you, leave a review so it reaches the people who need it most.
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Jan 9, 2026 • 50min

Season 88, Episode 1056: 2025 NYE Lollapalooza Episode 9: Fathers, Founders, and Focus

Episode 9 of the New Year’s Eve Lollapalooza is one of those conversations that doesn’t stay in “business talk.” It goes straight into what leadership actually costs—and what it gives back—when you’re building companies while trying to build a life you’re proud of.Jay Doran and co-host Mike Calhoun are joined by Steve Wilmer, Carl Eppolito, Pete Fournier, and Chris Tighe for a roundtable that blends family, faith, discipline, and execution—without the highlight reel.Carl Eppolito opens with a story that hits hard: the moment you realize you’ve already spent two-thirds of your lifetime time with your child before they even turn 13. As a single dad, he shares why stepping away from a high-travel corporate path wasn’t a sacrifice—it was a decision to stop missing his life. His word for 2026: Accountability, and it’s as much about health and habits as it is about being present for his daughters.Pete Fournier, founder of All Things Insurance Group, brings the operator perspective: growth is great, but growth without systems creates a business that owns you. Coming off a year of expansion and trimming dead weight, his focus is simple: Efficiency—stop stepping over dollars to pick up dimes, and start building leverage like a real CEO.Steve Wilmer delivers a lesson most founders learn the hard way: putting your head down and “accelerating” doesn’t matter if you’re not paying attention to where you’re actually going. After a year that looked busy but paid less, his word for 2026 is Focus—moving from the red ocean to the blue ocean with higher-value accountability and fewer, better clients.And Chris Tighe ties it all together with a builder’s mindset—military background, hard-earned business growth, and the humility to admit the real battlefield is internal. After a year of persistence through adversity, his word for 2026 is Growth—in fatherhood, relationships, leadership, generosity, and the systems that will carry his company forward.This episode is a reminder: your next level isn’t only about revenue. It’s about the standards you keep, the people you choose, and the discipline to build what matters—on purpose.Share this episode with someone who’s trying to grow without burning out—and leave a review so these conversations reach more leaders who need them.
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Jan 8, 2026 • 55min

Season 88, Episode 1055: 2025 NYE Lollapalooza Episode 8: Awake, Persevere, Improve

Episode 8 of the New Year’s Eve Lollapalooza is a fast-moving mix of real talk, hard lessons, and the kind of “in-the-trenches” clarity you only get when builders stop pretending everything is polished.Jay Doran and co-host Mike Calhoun are joined by Vinnie Candelore Jr., Jeff Winnick, Jake Penny, Kayvon Kay, and returning guest Demetri Stakias for a conversation centered on two themes: what 2025 demanded from you, and what 2026 is requiring of you.Here’s what makes this episode hit:Jake Penny breaks down a mission-driven approach to “Main Street investing” through Wealth Without Wall Street—teaching people how to move retirement dollars into cash-flowing real estate with real social impact. He shares the reality of scaling a portfolio (134 properties in four years), the pressure of a changing capital market, and the word that carried him: Persevere.Vinnie Candelore Jr. speaks like someone who finally woke up to what entrepreneurship actually is. Art may get you in the room—but relationships, systems, and execution keep you there. His word for the year: Awake. And his story is a live look at what it means to build something for your family while still learning the game in real time.Kayvon Kay brings the edge and the honesty. He talks about the founder being the bottleneck, the necessity of surrender for real growth, and what it looks like to come out of a year where the goal was simply to exist—and still end up with massive momentum. His takeaway lands hard: you don’t get growth without surrender.Jeff Winnick shares “mortgage miracles” from a small team producing big results—and then gets pushed (in the best way) to define what “better” really means in 2026. The answer becomes clear: more leverage, stronger delegation, and improving as a human first.And through it all, Jay and Mike keep coming back to the point of the Lollapalooza itself: connection. The people in your world matter. The way you show up matters. And leadership isn’t just output—it’s care.If you’re building through a pivot, a reset, or a reinvention… this episode will feel like a mirror and a push.Share this episode with someone who needs a wake-up call—and leave a review so we can keep bringing conversations like this to more people.

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