Why Company Culture Is Your Hidden Profit Driver | Dan Pascone with Jay Doran | Podcast #31

Posted on August 11, 2025 by Dan Pascone

Episode TL;DR

In this episode: Dan and culture strategist Jay unpack why company culture isn’t pizza, beanbags, and perks – it’s a hidden profit driver that shapes customer experience, retention, and long-term enterprise value. They walk through how founders can mature into true CEOs, turn “founder chaos” into clarity, and use culture as a real moat in a remote and hybrid world.

Who this is for: Founders, CEOs, and business leaders who want their company to grow profitably, keep top talent, and build an organization that lasts – not just a job that depends on them personally.

Key Takeaways

Culture is a profit strategy, not a perk program. Jay frames culture as values, story, and rituals that drive how people behave every day – which ultimately drives customer service, retention, and the bottom line.
The behaviors that make you a great founder can hurt you as CEO. Chasing every new idea, relying on instinct, and doing it all yourself may work at zero to one – but they often destabilize the business as headcount and complexity grow.
Distressed cultures become distressed assets. Partnership conflict, failed mergers, and high turnover are usually culture problems first and financial problems second – which is why private equity and strategic buyers increasingly focus on culture.
Remote and hybrid work make culture a “secret weapon.” When great people can work anywhere, clarity, trust, and aligned incentives become the moat that keeps them engaged and reduces the pull of constant outside offers.
Leaders must choose what they’ll be terrible at. Jay’s “hack” for focus: accept tradeoffs, get clear on what you won’t do, and re-define your role so you’re carrying something heavier – not competing with your own team.

Key Moments

00:02 – Dan opens the show and frames the mission: helping business leaders live their version of a rich life.
00:49 – Introducing guest Jay Doran, Founder & CEO of Culture Matters and host of The Culture Matters Podcast.
01:49 – What Culture Matters actually does: advising founders maturing into the CEO role and why consulting is a “healing profession.”
04:28 – The founder journey: why the skills that start a business are very different from the skills that scale one.
10:45 – Do leaders really believe culture matters? Distressed cultures, distressed assets, and culture as a post-merger X-factor.
15:19 – Beyond “pizza and beanbags”: how clear aims, trusted management, and reinvestment actually build culture.
24:01 – How culture shows up on the P&L: customer service, reinvesting in people, and profit.
27:25 – Lightning round: coffee, books, Charlie Munger, Jordan Peterson, and the advice Jay would give his younger self.

Episode Summary

In Episode 31 of the Making Sense of Your Money podcast, Dan sits down with Jay, Founder & CEO of Culture Matters, to explore why company culture is far more than office vibes – it is a core driver of profit, retention, and long-term enterprise value. Jay explains how he works with founders who have “sold themselves out of a job” and now need to grow into CEOs who lead people rather than personally selling and fulfilling everything.

They walk through the founder journey: in the early days, it’s all sales, marketing, and survival. As the organization grows, the same impulses that made the business successful – chasing every opportunity, starting new things, running on gut alone – can create volatility and even threaten the business. Jay compares entrepreneurship to market volatility: short-term swings are inevitable, but if you stay in the game and mature your leadership, you can compound value over time.

The conversation moves from abstract “culture talk” to hard business outcomes. Jay shares how distressed cultures become distressed assets, especially in partnership conflicts and mergers, and why in a remote/hybrid world, culture has become a strategic moat. They dig into what real culture looks like – clear aims, trusted management, aligned incentives, and continuous reinvestment in people – and how leaders can transition from rainmakers to builders of enduring organizations. The episode closes with a lightning round that reveals Jay’s influences, personal hacks, and the advice he’d give his younger self.

Full Episode Transcript

Transcript edited lightly for clarity.

Narrator: Brought to you by Tailored Wealth, helping business leaders live their version of a rich life.

Dan: Welcome to another edition of the Making Sense of Your Money podcast, where we cut through the financial noise and help business leaders to make smart, confident money decisions. Welcome to episode number 31 of the Making Sense of Your Money podcast.

Dan: I’m your host, Dan. I’m the founder and CEO of Tailored Wealth. And each of our episodes features a trusted voice in the financial world, bringing their expertise to help high achievers confidently make sense of their money. Today, I’m excited to introduce a really special guest and someone with some unique expertise that I’m excited to chat with. We’ve got with us Jay.

Dan: So Jay is not only the founder and CEO of Culture Matters and a real expert on leadership and company culture, but he’s also the host of the Culture Matters podcast, which I had the privilege of joining recently and had a lot of fun chatting with Jay. So Jay, thanks for being on my show. Thanks for joining Making Sense of Your Money. We’re pumped to have you, man.

Jay: Thank you. And if you want to check that out—amazing episode 966, season 81. Dan, you’re an amazing guy and great at what you do, and so it’s a pleasure to be on your show and I’m honored for the opportunity. I’ve got a quote that I’ll share.

Dan: Let’s do it.

Jay: I like to share a quote when I start shows: “Invisible threads are the strongest ties.” Friedrich Nietzsche. It’s about the connection that we can have to someone that we’ve barely met, but I think we had that. So, thank you for your setting the table.

Dan: I think maybe we’ll talk a little bit about invisible threads as we go on, but let’s start, Jay, because I know our audience has a lot they want to hear from you. Tell us at a high level what you do, how you got into it. I really love how passionate you are about your work. So I know that that’s going to come out when you chat about this, but tell us a little bit about Culture Matters, what you do for your customers, and how you got into that field.

Jay: Culture Matters: we are an advisory firm. We’re in consulting. We are trusted advisers. I got into it—it’s all I’ve ever done, even before I knew what I was doing. It’s a blessing. It’s a gift. I found out that a couple years ago, my last name is Doran—like Duran Duran. In Hebrew, it means “gift.” So, I’ve been a gift.

Jay: And I’ve been gifted with certain abilities: abilities to lean in, abilities to research, abilities to be curious and have a sense of urgency to help people—like you do, like the advisers that work with you, like the successful people that I’ve had the opportunity to interview on the Culture Matters podcast. So, what Culture Matters is: we are an advisory firm. We do consulting.

Jay: I specifically—my core subject matter expertise—has been working with founders maturing into the role of chief executive officer, because not all CEOs are founders but all founders are CEOs. That’s been my core expertise for over 10 years—meaning I’ve actually been doing this for over 10 years and somehow been very successful at it.

Jay: So what does that look like, the how piece? It’s a lot of research. It’s a lot of listening, like you do a great job on your show. It’s inquiry, questions, a tremendous amount of reading and preparation. For those that aren’t familiar with the consulting world, this is the healing profession. This is the helping profession. These are the helpers that are behind the scenes in the organizational charts.

Jay: You may have crossed paths with some throughout your tenure of varying degrees of complexity or character development, but at the end of the day, it’s a helping, healing profession. And Culture Matters… I’ll digress. I could answer that more, but I thought it was so important: values, story, rituals—like to like where you work and want to be a part of something. I thought that was super important early in my career.

Jay: So, I would say I’m a consultant, trusted adviser. “Culture matters” is a mantra. It’s like: it matters. Let’s pay attention to it. Yeah, I’m practicing that part.

Dan: I love it. Being behind the scenes and doing all the interviews and being the adviser—like I’m practicing this. Yeah. I mean, listen, you speak very strongly toward some of my core values and core beliefs because I’ve been a part of various different stage companies—big companies, small but growing companies—and now growing and building out my own firm.

Dan: Okay, talk to us a little bit about what are the biggest challenges that that customer of yours that you mentioned—the founder that’s trying to evolve into a CEO, right? They’re trying to go from, “I started the business, I maybe proved the concept, I learned a little bit how to make money,” but we know that running a successful long-term, tried-and-true business that lasts is about a lot more than making money. So let’s unpack what you help those leaders do in your work.

Jay: Well, first I want to preface and say the context—the context is going to come from observation and discovery of each unique circumstance, but I’ll do the best I can to speak in general. So I’ll give you an example: someone that started their business that’s listening, that started yesterday—the behaviors that they’re going to have to model are likely different than someone that’s been in it for 5 years or someone that’s been in it for 15, right?

Jay: They’re different because the organization—the actual org—like the organization size, how many people work for it, how many customers it serves—that all influences the responsibilities that that person in that seat is facing and those headwinds or tailwinds depending on the season, the seasonality of business.

Jay: So the trusted adviser is an accountability mechanism to ask necessary questions and give honest feedback, as an example. The consultant is retained to do a foray of different projects to help create market advantages for a company. But I just want to preface and say that one thing would be: let’s say we’ve succeeded. We’ve actually hit our goal. What’s next? And who’s on the team and do they know what they’re doing? Because it might have changed—what they need to be doing, right?

Jay: Or, “I don’t even like that person anymore.” Abraham Lincoln once said, “I don’t like that person very much; let me get to know them.” So, is it because there’s not affinity, or because I’ve changed, you’ve changed, it’s all changed, and we need to come back together and have some curious empathy for one another? Reimagine the role and reimagine the… For the business owner that might have had the best year that they ever had, that could actually create, like, the—that founding consciousness—that could actually create the most surprising thing ever: like a downness, a sloth, an apathy, a boredom.

Jay: And what can easily manifest is now trying to chase that high and starting something else. That is so important as an impulse for the founding consciousness. However, without the human, the people, and the clarity, it may be exactly what the organization doesn’t need at that season to get momentum and get to the next level.

Jay: So there are all these fighting and competing impulses of entrepreneurs that start businesses that are necessary and simultaneously—depending on the season, depending where the business is—can actually, the same thing that made it great, be the impulses that can actually destroy the whole thing. That’s why—alright, let’s use a financial context.

Dan: Okay.

Jay: You look at one of those charts—

Dan: Yep.

Jay: It’s not a straight line up. If you like the compounding returns, you have to look farther and farther out at the S&P 500—you have to go farther and farther out to see the average go up.

Dan: Yeah. Yeah.

Jay: So in the short term there could be insane volatility, right? Of course. A bit like the entrepreneurial journey—what all of us are going through listening to this, experiencing this—is the volatility. Like all those little volatilities are your life and my life and the listeners’.

Dan: 100%. 100%.

Jay: And so I always say: it ain’t for everybody. It ain’t for everybody.

Jay: There’s real—yeah, there’s real. And I think even just thinking about that, like someone listening to this podcast—what is that, efficient market theory? It’s like, hopefully you’re a little bit more efficient by listening to this. This information—it’s helping you: “Oh man, maybe I could, you know, give myself a break today. It’s not the end of the world. My life is that blip on the chart. That’s volatility. I’m the business person. I’m the entrepreneur. This is how it’s supposed to be.”

Jay: So, like, this is core values. If we’re going to have a core value conversation—like what we stand for as an organization—the value of those values is how the team uses them to figure out: where are we going, why are we going there, where have we come from, who’s on first, who’s on third, right? Abraham Lincoln: “Oh, I don’t really like that man. Let me get to know him.” A lot of my job is to hold a mirror and to help figure out what’s next and where have we come from.

Jay: So founder journey is: it’s sales first, right? Marketing. You have to market, now you’ve got customers, and now you need help with fulfillment. Like, okay, so now I need people that care about this as much as me, right?

Jay: But why should they? I mean, they don’t get the big win. So wait—they must have to like me at some level and believe that they’ll get paid. So how do I disincentivize them from that? Don’t pay them. Don’t communicate clearly. Be unclear of what’s next. Well, guess what? That’s kind of part of the process of being an entrepreneur—to be unclear of what’s next. It’s a lot of intuition to not be super clear. It’s a lot of fear.

Jay: So just so everyone… I’m not painting a negative at all. We need—we actually need—negativity for positivity to mean anything. Think about it. Use common sense. You need negativity for positive to have any meaning. So I’m not painting intentional negative. It’s like: no, this is the good news. Don’t quit. Stay in the game.

Jay: Stay in the game. Keep going. Keep listening to the podcast. You know what? Subscribe to my podcast. Listen to me every day. Listen to you every day. Keep feeding the beast. Keep consuming books—my books, your books.

Jay: So I get excited when we talk about these topics. I’ll float around. I think it’s hard and we need people. We need peers. We need mentees. We need mentors. We need podcasts. And that’s my short answer to begin the… to begin the…

Dan: Alright. So I got a question for you. This is going to be an interesting one. I’m interested to hear your thoughts. So I love the name of your brand, right? “Culture Matters.” When you’re engaging with a CEO or a senior leadership team or, you know, HR—whoever brings you in to do the great work that you do—generally speaking, do they understand and grasp that culture really does matter?

Jay: I built my reputation with partnership conflicts.

Dan: Okay, talk to us about that.

Jay: Yeah. The two biggest disruptors to a small business are personal divorce and business divorce, right? I built my reputation, my skill set, on that conflict. When there’s, like, a merger, for example, of two cultures—like a company’s buying a company—right? Inherent in that, it’s all about the culture, right? Because if that doesn’t…

Jay: If that doesn’t—it’s like you have a cut, you have a wound and you’re healing it—you have an infection. Even a giant company gets a little company; the small company can actually infect the big company.

Dan: Yep. Yep. Sure.

Jay: So where I built my career was distress. Distress. Keep in mind, being a very young person with these concepts and these ideas—this was not, I didn’t invent anything in that sense. I have my own interpretation of old ideas. But, you know, 10 years ago, 9 years ago, 8… 11 years in my swamp: “culture matters” wasn’t as… like, when the pandemic happened it became more prevalent: “the culture, the culture,” because now virtual work and things.

Jay: It wasn’t prevalent. So I cut my teeth and got my experience in distressed assets—because distressed cultures become distressed assets, right?

Jay: Pop-culture-wise, culture is thought of as like… and that’s made me a better adviser, better consultant—like, just better. It’s like: that’s awesome, right? Okay. Pop-culture-wise, you think culture—it’s one of those things that’s everywhere and nowhere. It’s very amorphous. It’s philosophical. It’s heady. I love stuff like that. That’s not…

Jay: So it’s either relegated to just theory or a very specific niche like I just said—the acquisition, the merger—or bean bags and pizza parties and kind of like, “Oh, that’s culture,” right? And you know what? It is not bean bags and pizza parties. Culture is at the root of what business is. It’s people going to work and serving customers and that’s fulfilling their life.

Jay: Culture is the values of the organization, the story that drives it, how the leadership actually works. So I would say to answer your question, because we’ve had such long tenures with our clients and grown with them over the years, it was easier to resell a relationship with value than to start a new one.

Dan: Right. Of course. Always.

Jay: We were kind of blessed with being able to grow with our client partners over the years and watch the fruit of the labor take place. I’m at the tenure in my career now where I’m really promoting and prioritizing the Culture Matters in this way, and I’m now having those meetings that you’re saying where people are like in the boardroom, you know, “culture”—it’s like “duh.” It’s like, well, of course. But the world has changed, so it’s actually a secret weapon. How do you actually get people bought in, right?

Jay: It’s a secret weapon when all the incentives are changing, when technology is leading us to be able to work at home fully or be hybrid or not be in the office. That fact changes how a company invests its capital, right? In its people, right? It changes everything.

Jay: So I am very much excited about that core focus and culture—being in that consulting and advisory world that influences big business, small business, medium business. That conversation is changing where people—very, very successful, like super high up—

Jay: They’re actually thinking, “Oh, we know it’s not pizza and bean bags and all that stuff. It’s something we really need to pay attention to,” right? Because if it’s not right, all the math that we did with our private equity investment isn’t going to work. Or that merger we just did isn’t going to work. Or, you know, we have people that are super talented that we want to keep, but they’re getting offers every five minutes from the next guy, right?

Jay: How do we compete with that? Culture is becoming a hedge. It’s a moat. The understanding of it, the understanding of how to actually make it productive and how to take action on it.

Dan: So I got a question from that. You mentioned—I love the analogy or the concept of pizza and beanbags, right? So I think years ago a lot of people, that’s what they saw culture as—pizza and beanbags—and the tech world sort of gave that a lot of gravitas, right? Now in a remote/hybrid world, how do you replace pizza and beanbags with something that’s a lot more meaningful and a lot more lasting? Because pizza and beanbags can go away tomorrow or maybe doesn’t even exist anymore in some cases.

Jay: Look, I want to speak to that. Pizza and beanbags… everyone listening to this, employees or whoever—they will naturally want to get together if they have relationships from work. The question becomes: what builds relationships at work?

Jay: The relationships naturally for you at work, right, are a symptom of clear-aim management that’s trusted. They’re living the core values and people actually think that. They’ve set up the accountability measures with coaching, their own self-development platforms, right? It’s like the financial adviser that has a financial adviser—they’re self-aware.

Jay: They’ve put an accountability mechanism to have a feedback loop. I interview a lot of advisers on the show and, yeah, of course. So the vision, the aim, the commitment—the company’s actually investing capital back in the business. That’s going to be known and understood by the team—it doesn’t even need to be talked about.

Jay: It’s almost like we go to work and we forget that the people working for us are either as smart as us or much smarter.

Dan: Hopefully smarter. That’s what I look for.

Jay: Hopefully. And they have perspective. They get to see how I’m the dumbest guy in the room. I get to talk about these high-falutin ideas and try to put them into action with other smart people supporting and acting that out.

Jay: So the bean—this is what the bean bag and all of that extra stuff… when the team stops doing that, it’s just telling us we’re missing something.

Dan: Right. Because—

Jay: We’re not here to create a guilt.

Dan: We want to do that if they’ve got the culture right.

Jay: Yeah. And the culture is going to, just like any relationship, have ups and downs. The culture will be revealed in the bad times. It’ll be invested into in the good times. The better it’s invested into, the bad times will be more success. Like, we’ll be failing, but at least we’re excited. We’re in a boat together. We’re storming Normandy. You know, leadership is what creates this—a big piece of that.

Dan: I’m glad you said that because that was where I was gonna go next with you. So I know how astute you are and how much of a real lifelong learner about leadership you are. I want to talk about that for a second because you mentioned earlier—and I thought you laid it out beautifully—when you’re starting a business, the first thing you naturally do is figure out, how do I sell whatever I’m trying to sell, right? Market it, sell it, build a brand, all that stuff.

Dan: Now, if you figure that out and you’re able to get past that phase, the next phase is like, “How do I grow this? How do I scale this?” And that requires a completely different skill set than, “How do I sell something?” I’ve spent a lot of my career focused on sales, but I’ve also spent a lot of my career focused on leadership.

Dan: So the natural thing that you need to do in order to go from selling something to building a lasting business is have the ability to lead people. And that to me will create the greatest benefits in your work and the greatest joy—at least for me—but also create (this is a show about money) the best financial results, if you know and you have the ability to lead people and get people to follow you. So talk to us a little bit about: how do you make that transition from an early-stage “I figured out how to sell something” to “Now I gotta figure out how to lead people and be someone that people want to follow—to follow my vision and my mission and why I set up the company—and make it sort of a team sport as opposed to an individual or a very, very small team sport, but growing it into a larger team sport”?

Jay: Let’s say we hire the right person. They’re going to need to see our values in our behavior. Now, the values that they’re watching—it’s within a context. It’s like: so I hire the right person, they have the talent, they have the skill, I’ve got to get out of their way. That doesn’t mean that I don’t pick something up even heavier.

Jay: And it makes sense to them. It has to make sense for the future of the company and them for that respect and that trust to be—“invisible threads are the strongest ties.” It has to be aligned, and that’s where it’s not just communicating with the mouth, right? If I’m used to selling, I’m a founder, I’m communicating with the mouth to my potential customers and I’m communicating with the actions with fulfillment.

Jay: It’s a pattern interrupt now to go from communicating with the mouth and the actions with the people. It’s a different context. So the question is, if I’m in that position listening to this where I’ve sold my way out of a job, I gotta figure out what my job is again, right? That’s where people like me in the helping professions—from Main Street to the Fortune 5—have jobs. Just like, yes, you could manage your own money, but hire Tailored Wealth to tailor that for you because you focus on what you’re serving.

Jay: So now let’s go to the other side. Let’s say that’s the good hire. They need to see; it needs to make sense for them. So there’s that respect, and that’s the behavioral piece. Then there’s, of course, the economic piece. It’s: how are people being incentivized to actually feel they’re proud about what they do, they believe in the company, and it’s competitive, right?

Jay: I had a very astute and successful executive search founder on the Culture Matters podcast, episode 979, yesterday, who said compensation—and he was talking within the context of senior leaders, like they’re really beyond the money—but on the human element, compensation is not the motivator. It could be a demotivator. It’s opportunity and whitespace: opportunity to grow and then whitespace to be creative.

Jay: There are these deep human emotions—motivators—that the good, the best people, right, that literally could take your job. Well, they’re not going to want to take yours if they don’t see that you’re carrying something heavier, right? And you’re all going the right direction.

Jay: And that nuance is really tough. Period. Tough. It’s tough. It’s hard. It’s hard. Now, let’s just say the other extreme: the not-best hire. The reason the worst people is tough is because an institution that’s being run that’s not run at its fullest efficiency kind of kills great people—like all the people in the middle, too.

Jay: So, you know, it’s like… what happens to Abraham Lincoln in… well, shoot, what did happen to Abraham… let me just digress. I’m saying, like, clearly the structure of the country influences whether someone lives or dies based on what they say and the decisions they make. There’s their context.

Jay: So what I’m saying is there’s a lot of people that weren’t bad. They were good, but they became disenfranchised. They’ve checked out.

Dan: Right. Right.

Dan: Go ahead.

Jay: So, well—I just… yeah. The incompetency conundrum ultimately falls on… because it is real. It does exist. But it’s like, well, who hired them and why, and why were the mistakes made? Now, mistakes are going to be made. It’s a ratio. But is it like 80% of the time I’m wrong or is it 20% of the time I’m wrong? And that ratio is important to understand how management makes choices.

Jay: But keep in mind, management’s ability to make choices is also tied to the vision, the strategy, the responsibility. Focus creates value and lack of it implodes it, right? And we live in this crazy society where we’re being told every day we should be and/or be someone else or be somewhere else.

Jay: So I’ll digress. I would say that is a conversation that could change a company’s trajectory: the difference between no profit and profit, the difference between having a legacy and not.

Dan: Staying around and not staying around. For sure. All right. On that note, that’s a perfect segue into what I was going to cover next. So, this is a show about money. I want you to start to help our audience understand how culture helps the company make money. Because I think sometimes the misperception is it’s just a feel-good thing—“I want people to like me, I’ve got feelings, so I want to come to work and like the people I work with.” But I know you and I know and feel that culture is a real investment with serious return on that investment. I want you to help our audience understand that.

Jay: Culture is a consequence of customer service, and it’s how the company reinvests into its people that drives that customer service, which drives profit. It’s a strategy. It’s human capital. It’s a hiring conversation, right?

Jay: It’s a reinvestment conversation. I like to look at it as—and this is why I like a culture map. Everyone, you know, you want the treasure, you need a map. So my role is to provide that map. Like I said, it’s nuanced. Each individual that’s listening to this has a different context that they’re operating in.

Jay: So I gotta figure out what the map is if I’m the third party observing the people that are looking for their treasure, that are building. They need the map. They need advisers. They need a great team. They need to be sold on themselves. So this whole thing that culture and profit… or “culture doesn’t lead to profit” or “culture isn’t profit” or “culture is just this or that.” No, no, no.

Jay: Culture is the business. It’s people. People are showing up. People are working at every level. They’re working as intelligently with the highest or least amount of integrity. So no, no, no. This is a business conversation. It’s just the study of culture and cultures and organizational culture has made us extremely successful at helping businesses with what you just said.

Jay: Right. What is profit? Profit comes after the service creates more value than there was. Profit is how it’s managed, right? How people show up, the purpose that they have. Our society is changing. People have more options. They’re staying shorter times with companies. They’re just doing that.

Jay: So how do you get the most out of someone that’s going to be there for the least amount of time? Or how do you develop a culture where someone wants to stay longer? The longer someone that’s really good stays, the more that they’re worth to the company.

Dan: 100%.

Jay: So this is a dire conversation. Companies that don’t understand culture, they’re not going to be companies. They’re not going to exist. They’re just not. They’re going to fail.

Jay: Or… you know, we could do a whole show on how I’m just incentivized to say that because I like culture.

Dan: Yeah.

Jay: So you choose, you know, good or evil, right? Whoever’s listening to this: you decide. Do you care? Or if you don’t, hey, that’s going to be your culture. I’m not here to impose what your culture should be on whoever is listening to this. But I do believe it matters. I do believe it, and I do believe—based on what I’ve seen and what I’ve studied.

Dan: I love it, man. And your passion comes through, as always. Alright, that was great, Jay. So we’re going to shift gears a little bit now and we’re going to learn a little bit more about Jay.

Dan: Alright, so you are now officially entering into the Making Sense of Your Money lightning round. Alright, so the deal with this is I’m going to ask you a question. It could be a one-word answer, it could be a long, drawn-out thought. Whatever comes first to your mind, I want you to share. And I think we’re going to have some fun with this one. We always do, but I think Jay’s going to crush this one.

Dan: Alright, so, you ready?

Jay: Sure.

Dan: Coffee or tea?

Jay: Coffee.

Dan: One meal for the rest of your life. What is it?

Jay: Can I say coffee again?

Jay: Not a big foodie. I would have to defer to my wife.

Dan: Okay. Whatever she wants.

Jay: Yeah, she’ll know what’s best.

Dan: There you go. Okay, that’s a good answer. That’s a good answer. I hope she tunes in.

Jay: I’ll probably be stuck eating nothing. Drinking coffee, like Immanuel Kant.

Dan: What’s one tool or piece of technology—could be hardware or software—other than your computer or your phone that you can’t live without?

Jay: I would say a book. The printing press was invented in the 1440s, and that technology led the everyday person to be able to have information—the stores of knowledge of the world. And I love my books.

Dan: Yeah, for sure.

Dan: Are you a hard copy, paperback, hardback? Are you a Kindle? Are you an audiobook—a little bit of all? What do you do there?

Jay: I have the physical… they’re different experiences and there’s value, in my view, on all of them. Especially the physical reading—it’s a different experience than listening. Physical reading, I like a soft-cover book, and that’s a meditation that I intentionally do consistently. There were years where that was a lot less and all I believed I had was listening to books, because of trying to work 18 hours a day every… like, okay, the entrepreneurs oftentimes—“When do I read?” So I listened, and I have listened to over 12,000 hours of Audible since 2015.

Jay: It’s a lot of audio listening that I’ve done to educate myself in dozens of disciplines to be qualified to teach company culture to insanely successful people.

Dan: Love it. I do a little bit of both.

Jay: But I like both.

Dan: Yeah, I do both, too. I’m with you on both. We can chat about that more sometime. Alright, this is a good one. I’m excited to hear your answer on this. Favorite quote or phrase about leadership or success?

Jay: “Life can only be understood backwards but must be lived forwards.”

Dan: Ooh, that’s a good one. Who’s that from?

Jay: Søren Kierkegaard. He was a Danish philosopher, like the Socrates of Christendom. I love his work. He wrote like two dozen-plus books in 42 years. You know, he wrote hard. He died young. He drank a lot of coffee.

Dan: Okay.

Jay: You could say dramatic.

Dan: I understand why you like him.

Jay: No, Søren was pretty amazing. Brilliant, brilliant guy.

Dan: Love it. Love it. Alright, so on that note, favorite book on leadership, business, success—however you want to frame it.

Jay: I like Charlie Munger’s Almanac. I used to mail that—well, not used to, I still do, it’s just less. I haven’t mailed it to anybody in a while. It’s a book that was compiled—it’s 520 pages, beautiful pages that are anecdotes from Warren Buffett’s business partner, older-brother-esque mentor—

Dan: Yep.

Jay: —who was really the architect. In the last shareholder letter after Munger’s passing—Charlie Munger passed away in 2024—he was 99 and 11 months. Pretty amazing. Right before his 100th birthday, he passed away. We lost him.

Jay: This book is about his “Mungerisms,” the books that he talked about and prioritized in the shareholder meetings. You can read it on any page. It’s like different commencement addresses. It’s a treasure trove of other wisdom that one could go into. And the relationship that he built with Warren Buffett and how they built Berkshire Hathaway—the business of businesses—is a very motivating, inspiring book that I love for business from a wisdom standpoint.

Jay: Definitely a leadership book, because these are leaders that led at such a degree that it doesn’t even look like what you might think leadership is. It’s so subtle and they’ve impacted so many people. So yeah, that’s a leadership book I like.

Dan: Love it. Great stuff. Do you have a personal hack you can share with our audience?

Jay: A personal hack? Everything has a consequence. Choose what you’re going to be terrible at. Be very clear what you’re going to give up to get something. Everything will come with something that you’re going to likely regret. Everything.

Jay: I think that is true. I think people have to figure out… I mean, if you want to—you study these Napoleons and these entrepreneurs, you read about Gandhi and Martin Luther King and these figures… Oh, here’s a personal hack: don’t worship false idols. Listen, ask questions, like you’re honoring me with. That’s a hack. I’m giving a lot of them, but pick what you’re going to—if we’re talking to the entrepreneurs—pick what you’re going to suck at or have pain around and use that.

Jay: If you’re talking about the employees listening, choose who to follow wisely, because with that comes… and I could go both, actually, because everyone’s following somebody. But yeah, I like that question. That’s a fun question.

Dan: I love it. I like how it went dark with it.

Jay: Yeah.

Dan: Alright, hopefully this one won’t be as dark. No, dark is good. What’s one bucket list item that you’ve already accomplished?

Jay: Definitely interviewing Dr. Jordan B. Peterson, who I’ve been a student of. His textbook Maps of Meaning is a great book—470 pages. His other book, We Who Wrestle with God, just fell on the table—I think I’m getting a message from God.

Jay: Dr. Peterson is an accomplished clinical psychologist with a great practice. He did his dissertation on alcoholism, I think, at McGill. He taught at University of Toronto for almost 20 years. He became popularized for some macro-political controversies, but he turned that into, in my estimation, helping millions of people with their personal responsibility.

Jay: Having the opportunity to prepare to interview him at the American Gift Conference in 2025 in front of people that I care about and have worked with for years and almost a thousand people in the audience—and doing the best job I possibly could to integrate his keynote into that interview so it’ll be valuable for the audience of mortgage brokers and account executives and vendors and so on—was something I’m proud of.

Jay: As I worked towards it for months—there’s even a 14-episode series on his third book, Beyond Order: 12 More Rules for Life, as part of that preparation. And I am very much a student of the textbook and his work. So there’s been an emotional tie with a stranger that could very well easily have ruined the interview because it might make it all about me—which it is a big part—but I believe I did the best job I could as the host. So I’m proud of that. That was kind of the crescendo of a long stretch of pain and suffering and work and failure and success. You can find it on YouTube—just type “Jay Doran Dr. Peterson.”

Dan: Love it. Love it. I’m going to check that out for sure. Alright, last one for you. What’s one piece of advice you’d give your younger self?

Jay: It’s not your fault.

Dan: I love it. It’s very simple. Very simple. Lot to it, but very simple. I love it.

Jay: Part two.

Dan: Part two. Yeah, we’ll get the rest on part two.

Jay: Kierkegaard said, “What if everything in life was a misunderstanding and laughter really tears?”

Dan: There you go. Laughter is really tears. By the way, that’s a good… anytime you’re having a tough day, think about that one. Alright, good stuff, Jay. Thanks—

Jay: I thought this was about business.

Dan: Yeah. Yeah. Yeah. Well, we get into a lot here. We get into a lot. Thanks for coming on. If our listeners want to know more about Culture Matters, want to know about you, connect with you—I know you’ve got a very well-subscribed and followed podcast—tell our listeners where they can find you.

Jay: Thank you for that. The Culture Matters podcast—black and gold. Please listen to an episode before you subscribe. Wouldn’t want to waste your time. But share it to a friend, or if you don’t like it, share it to an enemy. Maybe they’ll like it. The Culture Matters podcast. I mean that seriously. That’s good advice, I think. Right? Don’t just worship me. Check it out.

Jay: Listen to it. If you like it, give it to an enemy. Win–win–win for everyone. Follow me on Instagram. I’m thinking, like, if my wife listened to this, she’s like, “God, who let him out of the house today?” I’m in the house still. Instagram is jaydoran_thecultureman. Send me a message on there. Anybody listening to this, I’d be more than happy to talk with you, to thank you for the support. And listen—Dan has been on the show, episode 966.

Dan: Wow.

Jay: I don’t want them looking at the wrong one.

Dan: Glad I could get you while you’re still in three digits, man.

Jay: Hey, we’re about to cross. I’m about to keep talking—I know the show is over. We are going to hit a thousand soon. We’ll have to have you back, Dan.

Dan: I look forward to it. I’ll come in on a four-digit. That sounds great. That sounds great.

Jay: I just want to make sure—I think it was… I want to make sure I say it right. Yeah, it’s 966. See, I’m good. I looked it up.

Dan: Cool. Love it.

Jay: I don’t want them looking at the wrong one.

Dan: Love it. Appreciate you, brother. Appreciate you. Thanks so much for coming on. This was great.

Dan: That’s it for the episode. As always, you can find our podcast along with our newsletter and YouTube channel, all free, at makingsenseofyourmoney.com. And as always, remember to prioritize your version of a rich life. Cheers.

Resources & Citations

FAQs

Does company culture really affect profitability, or is it just an HR topic?

Culture shows up directly in how your team serves customers, how long great people stay, and how well they execute the strategy. Research from Gallup and others has consistently linked higher engagement and healthier cultures with better productivity, lower turnover, and meaningfully higher profitability. For founders and CEOs, treating culture as a “nice to have” can quietly erode enterprise value; treating it as a core business strategy can support both profit and valuation over time.

How do I know if my culture is becoming a risk to my business?

Warning signs include rising conflict among partners or leaders, stalled or failed integrations after acquisitions, increasing turnover in key roles, and a growing gap between the values you talk about and the behavior people actually experience. If every growth push creates internal chaos, or the best people seem emotionally checked out or are constantly taking recruiter calls, culture may already be a hidden liability. The earlier you address it, the less expensive it tends to be – financially and emotionally.

As a founder, how do I move from “rainmaker” to CEO without losing momentum?

The transition starts with redefining your job. Instead of being the person who sells and fulfills everything, your role becomes setting direction, modeling the values, hiring great people, and picking up “heavier” work that only you can do. That often means letting go of some sales or delivery tasks, building clear roles and incentives, and installing an accountability and feedback rhythm. A trusted advisor or culture consultant can help you see the patterns you’re too close to and design a leadership role that matches the next stage of the business.

How can we build a strong culture in a remote or hybrid company without pizza and beanbags?

In a remote/hybrid world, culture is built less through perks and more through clarity, trust, and rhythm. That looks like a clear, shared aim for the business, leaders whose behavior matches the stated values, regular communication and coaching, and visible reinvestment in people’s growth. You can still have rituals and fun – in-person offsites, virtual coffees, recognition moments – but they sit on top of a foundation of alignment and accountability, not in place of it.

When does it make sense to bring in an outside culture or leadership advisor?

Common trigger points include rapid growth, a major change in strategy, a merger or acquisition, partnership conflict, or the feeling that you’ve “hit a wall” as a founder. An experienced advisor can help you map where you are, surface hard truths, and design culture, leadership, and incentive changes that support your goals. For many leaders, this can be a high-ROI investment that helps protect the value they’ve already built and unlock the next stage of growth, subject to your company’s needs and budget.

How does my company’s culture fit into my personal wealth and life plan?

For many founders and leaders, their business is their largest asset and primary source of income. A stronger culture can support more stable cash flow, higher enterprise value, and options like succession, sale, or stepping back into a more “work-optional” role. Integrating culture work with your personal financial planning may help you design clearer exit paths, reduce stress, and align the business you’re building with the life you actually want, subject to your goals, risk tolerance, and overall financial picture.

Disclaimer

The information in this episode and on this page is for educational and informational purposes only and is not intended as tax, legal, or individualized investment advice. Any strategies discussed may not be appropriate for your specific situation and are subject to eligibility, current laws, and regulatory requirements, which can change over time. Before making financial, tax, or investment decisions, consult with a qualified professional who understands your personal circumstances.

Next Steps

1. See if a Wealth Clarity Chat is right for you. If most of your net worth is tied up in your business and you want a plan that connects culture, cash flow, and personal wealth, consider a Wealth Clarity Chat. You’ll talk through your goals, income, equity, and business realities with an advisor who works specifically with business leaders.
2. Explore Tailored Wealth’s approach. Visit YourTailoredWealth.com to learn how Life-Driven Planning and evidence-based investing can support the business – and life – you’re building.