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 — 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...

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 Ma...

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 o...

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 Givi...

"Every act of creation is first of all an act of destruction." - Pablo Picasso

Host 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 you...

"Lollapalooza effects can make you rich or they can kill you." - Charles T. Munger

Real 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 talki...

"The big money is not in the buying or selling, but in the waiting." - Charles T. Munger

One episode simply wasn't enough to go over everything we wanted to when it comes discussing market updates, so we had no choice but to make it a two-parter.  We are happy to welcome back our co-host for the Investor Series and the founder of Arena Securities, Aleck Arena, to put a bow on our last episode.  In today&apos...

"Soros has taught me that when you have tremendous conviction on a trade, you have to go for the jugular. It takes courage to be a pig. It takes courage to ride a profit with huge leverage." - Stanley Druckenmiller

In store on today's episode of The Culture Matters Podcast, we are returning to one of our favorite areas of discussion: investing!  And we couldn't think of anyone  better to broach the subj...