The Culture Matters Podcast

In Episode 18, Jay Doran and Jenna Silverman step back and reflect on the full scope of the NYE Lollapalooza — a day-long series of conversations designed to help people close one year with intention and step into the next with clarity.

Jenna, who joined as co-host for the final stretch of the day, brings a fresh lens to the recap as they unpack the patterns, themes, and through-lines that emerged across the episodes. Together, they...

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 ye...

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 p...

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 mara...

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 ch...

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...

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 a...

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 — no...

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: Leadership
• Ruth: Amity (agreement without avoidance — th...

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 e...

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...

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 th...

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 h...

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 t...

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...

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, durabi...

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 d...

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, bu...

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 break...