The Culture Matters Podcast

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.

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.

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.

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.

Episode 7 of the New Year’s Eve Lollapalooza is part coaching session, part brotherhood, and part wake-up call—because this crew doesn’t just talk about growth… they talk about the cost of growth.Jay Doran and co-host Mike “Mike Drop” Calhoun are joined by Alex Rawdin, Jeff Silva, Ken Jordan, and Demetri Stakias for a fast-moving roundtable that turns into something deeper: identity, resilience, and what it takes to rebuild when the punches don’t stop.You’ll hear each guest anchor 2026 with a single word:Jeff Silva lands on Consistency—rebuilding in a new market, owning the fall-apart seasons, and remembering that you don’t “find” momentum… you earn it.Alex Rawdin sharpens his initial instinct of “action” into what really matters: Execution—being effective, not just busy, while raising three young kids and helping lead a multi-decade family advisory firm.Demetri Stakias brings the most vulnerable turn: moving from last year’s word Unstoppable to this year’s word Love—after being forged by adversity that most people only hear about in headlines.Ken Jordan declares Transformation, and then opens up about the hardest part of leadership: rebuilding confidence after the difficult decisions of 2022–2023, learning the difference between empathy and compassion, and getting ready to recruit and lead again without fear writing the script.Then the episode pivots—hard—into one of the most practical moments of the entire Lollapalooza: go live.Mike lays out a conviction that feels like a challenge: if you do nothing different in 2026 except schedule consistent live conversations (YouTube, LinkedIn, anywhere), you’ll spend the year building trust, proximity, and pipeline—for free. Not performative. Not perfect. Just real, consistent, and present.This episode is for the leader who’s been carrying it alone… and is ready to get back into rooms that make them better.If you’re stepping into 2026 with a word, a mission, or a rebuild—this one will hit.

Episode 6 of the New Year’s Eve Lollapalooza is a collision of high standards and real humanity—where big goals meet even bigger intention.Jay Doran and co-host Mike “Mike Drop” Calhoun welcome a powerhouse lineup: Chris Vester, Maria Quattrone, Alan Whitman, Mike Modica, Matt McHale, with Jim Sabellico jumping in briefly to give flowers where they’re due.This episode moves fast—but it lands deep.You’ll hear Maria Quattrone share her 2026 word—Fearless—and the launch of her coaching and course work, including the Listing Boss 90-Day Listing Accelerator. She reflects on how consistency and community carried leaders through the unexpected, and later drops a rapid-fire “top lessons of 2025” that hits like a leadership manifesto: clarity, boundaries, momentum on boring days, and why rest is a strategy—not a reward.Chris Vester brings his signature grounding presence: 2025 was Pruning—not loss, but intentional elimination for growth. 2026 becomes Alignment, tied directly to his mission and advisory work, Align Your Nine. He reminds the room that “no is a complete sentence,” and that fewer, better things often unlock the next chapter.Then Alan Whitman, author of Break the Mold, unpacks the journey of transforming and scaling a traditional CPA firm—and why his 2026 must be Intentional, as he prepares to step into a new CEO role for a private equity-backed platform built to manage, protect, and grow prosperity for SMBs. He shares a practical speaking lesson that sticks: if you’re trying to stop saying “um,” don’t replace it with more words—replace it with a pause.Mike Modica adds the operator’s perspective: Discipline and becoming Replaceable—not to disappear, but to scale through systems, trust, and leadership development in a high-stakes world where mistakes cost real money.And Matt McHale stitches it together—stewardship, leverage, and discipline—showing how relationships, consistent learning, and leadership development create compounding returns.If you’re stepping into 2026 with a word, a vision, or a calling—this episode will sharpen it.

Episode 5 of the New Year’s Eve Lollapalooza is a masterclass in what happens when high-performing people slow down long enough to tell the truth.Jay Doran and co-host Mike “Mike Drop” Calhoun bring together a loaded room: Matt McHale, Chase Gallagher, Rob Wishnick, Bill Reiman, Bill Mervin, Jim Sabellico, and Stephen Ronald—a group with real history, real scars, and real momentum heading into 2026.The conversation starts the way the best ones do: quick intros, long relationships, and a reminder that nobody’s here by accident. Then it turns into something deeper—words for the year, what those words cost, and what they unlock.You’ll hear:Jim Sabellico break down the shift from Bold (2025) to Alignment (2026), and why owning your story is the fastest path to freedomRob Wishnick on evolving in a changing mortgage market—and returning to obsession as a competitive edgeBill Reiman on the tension between vitality and faith, and the line that lands: “Without faith, fear decides. With faith, purpose leads.”Stephen Ronald on moving from Relentless to Unbound—and why the way you get to 90 isn’t how you get to 150Bill Mervin on consolidation, guardrails, and building the next chapter without burning the house downChase Gallagher on simplify to scale, and why removing complexity can actually enhance performanceMatt McHale on stewardship and leverage, and how the real advantage is learning faster by borrowing wisdom from people who’ve already lived itThen Jay shifts the whole room with a question:What’s the biggest lesson you learned in 2025—one sentence only?What follows is a rapid-fire set of truths about discipline, presence, leadership, and letting the past stop weighing you down. The episode closes with a call to connection—because proximity, tribe, and authenticity aren’t just “nice ideas”… they’re the framework.If you’re walking into 2026 trying to become more aligned, more grounded, and more intentional—this one will hit.

Episode 4 of the NYE Lollapalooza is what happens when the conversation stops being theoretical—and turns into action in real time.Jay Doran and co-host Mike “Mike Drop” Calhoun are joined by a stacked room: Robert Frehafer, Bill Mervin, Brian McNally, Chase Gallagher, and Matt McHale—a group built on years of trust, shared history, and a common obsession with growth, leadership, and doing life with intention.The episode opens with introductions that feel more like tributes: stories of discipline, vision, resilience, and friendship. From mortgage leadership and development (Bill), to high-performance home services and coaching (Chase), to entrepreneurship, community building, and brand growth (Brian), to deep relationship-first leadership and long-term thinking (Matt and Robert), the room quickly locks into the theme that defines the entire Lollapalooza series: proximity changes people—if you show up ready.You’ll hear:Why simplifying systems is the fastest path to sustainable scaleHow leaders evolve from “doing everything” to building processes that lastBrian McNally’s 2026 word (Alignment) and the philosophy behind F** Average*Matt’s emphasis on service and mission, and Robert’s commitment to faith, family, and impactA powerful pivot from reflection to execution: the “Referral Party.”In the final stretch, Mike introduces the Board of Advisors-style “referral party,” where each guest calls out what they need next—connections, partnerships, speaking opportunities, brand support—and the room immediately starts building bridges. From getting Brian a Dana White foreword, to creating referral pipelines between landscaping, roofing, and pavement, to linking business growth with mission-driven service, this episode becomes a live demonstration of what real networks actually do.If you’ve ever wondered what it looks like when relationships stop being small talk and start becoming strategy—this is it.If you’re listening, share this with someone building in 2026—and leave a review so this community keeps finding the people it’s meant to find.

Episode 3 brings the NYE Lollapalooza deeper into the world of real assets, real operators, and real responsibility. Jay Doran is joined again by co-host Mike “Mike Drop” Calhoun, alongside Judd Burdon, Gray Wilson (Revolution Capital Group), and Robert Frehafer (Guardian Roofing) for a conversation that moves fast—but lands heavy.Gray shares how Revolution Capital thinks differently about real estate: long-duration holding, durability, and intentional value investing in core Philadelphia—avoiding the short-term flips that look smart until the market turns.Robert offers a powerful perspective from the trades—roofing and siding as both opportunity and responsibility—along with a personal story of faith, family, and transformation. The group zooms out to talk about how leaders in service industries can change lives when they stop treating workers like “labor” and start building people through culture, development, and long-term vision.Then the conversation turns sharply into the future: AI in the trades, asset assessments at scale, and the idea of building a “performance partner” network—not just subcontractors, but teams trained, supported, scored, and elevated through systems, standards, and shared outcomes. Judd lays out pieces of a broader ecosystem: tech platforms, equipment, training, dealer networks, and integration across pavement and roofing through property data and AI-driven assessments.A key moment: when asked to pick one word under pressure, Robert lands on it—Innovate. And that becomes the north star of the episode: innovation not as buzzword, but as stewardship—creating better outcomes for customers, better opportunities for workers, and better businesses built to last.This is Episode 3 for the builder, the operator, the investor, and the leader who believes the trades can be more than a job. They can be a movement.If you’re listening, share this episode and leave a review—because this series is built on one simple idea: the right people in proximity can change everything.

In Episode 2 of the NYE Lollapalooza, Jay Doran is joined again by co-host Mike “Mike Drop” Calhoun, with guests Judd Burdon (Asphalt Kingdom), Reagan Weiss, and Andrew Berman each bringing real-time reflections on growth, relationships, leadership, and the words that will define their next year.The conversation opens with a guiding quote: “Life is not a problem to be solved, but a reality to be experienced.”From there, the group digs into the “word” tradition—what last year required, what this year demands, and how transformation actually happens when the calendar turns.Judd shares a year marked by Change—a move across countries, leadership shifts, and a powerful “day with Jay” that reframed what’s possible. His word for 2026 becomes Integration, as he maps a bigger ecosystem across e-commerce, manufacturing, brick-and-mortar expansion, and technology.Reagan reflects on a year of Relationships—and why his 2026 word is Obedience: obedience to God, family, and the relationships he’s been given stewardship over. Andrew Berman joins the conversation to unpack his word, Accountability, and the structure required to actually live it—especially as a leader scaling a team and organization.Along the way, they debate founder vs CEO mindsets, discuss what makes real advisors different from coaches and consultants, and return to the core theme of the day: proximity can spark transformation—but only if your mindset is ready to receive it.If you’re entering a new year looking for clarity, better questions, and a deeper standard—this episode is your reset.