The Culture Matters Podcast

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.

"The big money is not in the buying or selling, but in the waiting." - Charles T. MungerOne 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's discussion, Aleck and Jay are taking a look at why Aleck prefers quarterly updates over monthly updates, where technology is heading and how it is affecting some investment strategies, the media force that is YouTube, the fact that there this an entire ecology surrounding a founder and how it is used to shape the company as a whole, and how to manage regret when it comes to not investing in something that maybe you should have that has taken off.  Aleck has a great mind for investing and we are always grateful to have him on The Culture Matters Podcast.Disclaimer: The information contained in this episode is not personal financial product advice and has been prepared without taking into account the objectives, financial situation, or needs of any particular person. Culture Matters does not hold an Australian Financial Services License and is not authorised to provide general or personal financial product advice. Before making any investment decision, you should consult a licensed financial adviser. Past performance is not indicative of future performance.

"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 DruckenmillerIn 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 subject with than our co-host of the Investor Series and the founder of Arena Securities, Aleck Arena.  During this discussion, Aleck and Jay are diving a little deeper into some specific companies and uncovering what the past few months have looked like from an investor standpoint.  We're also getting into not every investment is going to be a winner, the growth of potential return that comes with the success of a company, and how training leads to people looking for more lucrative opportunities.  We hope you enjoy this episode of The Culture Matters Podcast.Disclaimer: The information contained in this episode is not personal financial product advice and has been prepared without taking into account the objectives, financial situation, or needs of any particular person. Culture Matters does not hold an Australian Financial Services License and is not authorised to provide general or personal financial product advice. Before making any investment decision, you should consult a licensed financial adviser. Past performance is not indicative of future performance.

"Give me a lever long enough and a fulcrum on which to place it and I will move the world." - ArchimedesAfter a brief hiatus, The Culture Matters Podcast is back with a vengeance and we are starting this thing off right with a wonderful guest making his first appearance on the show.  A long-time leader in the business training space having worked with such companies as General Electric, and the founder of PCK Partners, Hector Sanchez, is joining us on the program today and we are extremely excited to be speaking with someone with Hector's pedigree and experience.  Hector and Jay are digging into what it means to be a servant leader and what makes this an important concept in the field of leadership, why it is up to the leader to understand and elevate the performance of those that are working underneath them, and why having a broader understanding of the business at large will help the leaders of organizations more successful in their endeavors to inspire and motivate.  If there was ever a master class in being a leader and what leadership actually is and boils down to, this is it.  Hector has a great way of describing his techniques and views on leading that make it plausible and easy to follow and we hope you get as much as you possibly can out of this episode of The Culture Matters Podcast.

On a very special episode of The Culture Matters Podcast, we are bringing back The Investor Series with the founder of Arena Securities and co-host of the series, Aleck Arena, flying solo.  Aleck's guest today is a man whose family has over 125 years of experience in the Australian financial market and who has been the chairman of that company, Soul Patts, for the past quarter of a century, Rob Milner.  Aleck and Rob are discussing Rob's family's history and how his great grandfather began this successful organization, some of the current trends in the Australian financial market, how that translates to the American listener, and some of the strategies Rob has employed to take his company into the 21st century and beyond.  It was a real treat to have Rob on the show and we hope you enjoy this episode of The Culture Matters Podcast.Disclaimer: The information contained in this episode is not personal financial product advice and has been prepared without taking into account the objectives, financial situation, or needs of any particular person. Culture Matters does not hold an Australian Financial Services License and is not authorised to provide general or personal financial product advice. Before making any investment decision, you should consult a licensed financial adviser. Past performance is not indicative of future performance.