The Culture Matters Podcast

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.

The NYE Lollapalooza is not about predictions or resolutions. It’s about reflection, responsibility, and deciding—consciously—who you are becoming as the calendar turns.In Episode 1, Jay Doran opens the day alongside longtime collaborator and co-host Mike Calhoun for a wide-ranging, deeply philosophical conversation on growth, transformation, and personal ownership.They explore the idea that life can only be understood backward, but must be lived forward—and why a new year isn’t a clean slate, but another shot to do it better. Through metaphors of fire, light, proximity, and chemical reactions, Jay and Mike unpack why some people ignite when placed in the right environments, while others remain “duds,” even when all the ingredients for growth are present.This episode dives into:Why real growth requires intensity, friction, and self-confrontationHow proximity to the right people creates transformation—if your mindset allows itThe danger of carrying old habits into a new year unchangedWhy repetition, practice, and responsibility are required to “grow your knife”The difference between collecting wisdom and actually activating itJay reflects on his word for the year shifting from Intensity to Love, framing love as “intensity externalized”—the act of caring deeply about the existence of another. Mike shares his own evolution from Recalibration to a defining word for the coming year: Different, underscoring the truth that better outcomes require different actions—and the strength to break old patterns.This episode sets the tone for the entire NYE Lollapalooza series:Think clearly. Take ownership. Be strong. Be different.And don’t just sit in the room—leave it changed.

Technology doesn’t fail, systems do.In this episode, Jay sits down with David Levine to explore the core of systems through the lens of technology and how the tools we build, adopt, and rely on quietly shape behavior, culture, and outcomes inside organizations. This is not a conversation about software features or trends—it’s about how technological systems influence the way people think, communicate, and make decisions.David breaks down why most tech frustrations aren’t caused by bad tools, but by poorly designed systems around them: fragmented workflows, unclear ownership, misaligned incentives, and a lack of intentional architecture. Together, they discuss how technology should support human behavior, not complicate it and why leaders must take responsibility for the systems they allow to exist.The conversation challenges the assumption that more technology equals better results. Instead, it reframes progress as clarity, integration, and purpose. When systems are intentional, technology becomes an amplifier of culture. When they’re not, it becomes noise.This episode is for leaders, operators, and builders who want technology to create leverage not friction and who understand that culture, efficiency, and execution all live downstream from the systems we design.A practical, thoughtful discussion on building technological systems that actually work for people—not against them.

Danijel Velicki is a Croatian-born entrepreneur and financial educator known as the Founder and CEO of Sqwire, an online financial wellness and literacy platform.Mark Richards is the founder and a principal consultant at Cool Hollow, a business consulting and financial services firm based in Pennsylvania.Mark and Danijel have been friends for 10+ years and have been working together and best friends ever since. When Jay attended Mark's company's event a few months ago Jay met Danijel and all three of them have formed a great and magical combination of minds. Today they spend the next hour with you discussing what it means to really show up for yourself, your people, and what you believe in. This conversation is just a small piece of how powerful these three can be together. Listen to the whole thing and learn from some of the best in business. 

In this episode, Jay and Jenna sit down for an honest conversation about what culture really is — and why it matters more than ever.They unpack the heart of Culture Matters: not as a buzzword or a corporate initiative, but as the way people think, communicate, and show up in their work, relationships, and leadership. Culture isn’t something you hang on a wall, it’s something you live every day, whether you’re intentional about it or not.Jenna, Jay Doran's wife joins the show and together, they talk about who they are as a team, why alignment matters, and how shared values create clarity in environments that often feel noisy and disconnected. They also discuss why culture must be built from the inside out, how values guide decisions when things get hard, and why leadership begins with self-awareness.This conversation also explores the power of thinking before reacting, creating space for honest dialogue, and building environments where people feel seen, challenged, and supported. At its core, Culture Matters exists to help people think clearly because when people think clearly, they change.If you’re a leader, entrepreneur, or someone who cares deeply about building something meaningful in business or in life this episode will challenge you to rethink how culture shows up in everything you do

It has been a couple of months, but we are finally back with Thirty Days of Thought featuring our very own Jay Doran as he discusses excerpts from his book, Thirty Days of Thought.  On today's episode, Jay is focusing on the chapter entitled "Happy Birthday".  We are kicking off the episode (recorded on November 16, 2025) with a very big happy birthday shout out to our friend, returning guest, and "Tales of Giving" series collaborator, Mr. Demetri Stakias!  From there, Jay goes on to discuss the blessing of having people around that don't give you a choice on whether or not you are celebrating your birthday, using the birthday as a caveat for action and for growth, and not using age as a measuring stick for your success or for where you think you ought to be in life if you aren't where you think you should be.  To anyone who listens to this on their actual birthday, we wish you the happiest of happy birthdays and we hope that you enjoy this episode of The Culture Matters Podcast.

"Every act of creation is first of all an act of destruction." - Pablo PicassoHost of "The Relief Podcast", author of How to Get Your Life Back, and founder of Real Estate Relief Demetri Stakias is here once again and this time it is at the start of a brand new series.  The "Tales of Giving" is going to be an uplifting journey we take with Demetri as we explore positivity and believing in yourself and not being afraid to be yourself.  In today's discussion, which just so happened to be recorded on the day separating Gary Vee's birthday and Demetri's birthday, we're starting off with Demetri telling a great story about dressing up like an elf to deliver Gary a birthday gift.  Whether or not the gift arrived will become clear once you dive into the episode, but the main point of the story is to find fun and whimsy and happiness in your day-to-day life and stop equating your happiness to your success.  The discussion also covers problem-solving starting up with the Gordian knot, being kind while also doing a bit of self-promotion, and having the courage to get up, leave, and do your own thing even on day 1 of an event.  We hope you are as excited for this series as we are to bring it to you on The Culture Matters Podcast.

"Lollapalooza effects can make you rich or they can kill you." - Charles T. MungerReal estate professional, businessman, co-owner of R.K. Reiman, and host of "The Real Build" podcast Bill Reiman is joining us on the show once again and we've got a good one in store for you today because we are jamming to some lollapalooza.  No, we don't mean the Chicago-based music festival.  We're talking about the Charlie Munger coined term "lollapalooza effect" which means a situation where multiple psychological biases, tendencies, or forces act together in the same direction, creating an extreme, amplified outcome that is far greater than the sum of its parts.  Bill and Jay are talking about the ability to make good connections between, how equally important it is to know when not to connect certain people, the benefits of a group of like-minded individuals coming together for the common good, and what it is that makes Naples, Florida such a wonderful, unique, and opportunity-filled place.  This episode is dedicated to bringing people together and we hope you're inspired to participate and appreciate those who are together with you after this episode of The Culture Matters Podcast.