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Liberty Mutual Spokesperson
And Doug, there's nowhere I wouldn't go to help someone customize and save on car insurance with Liberty Mutual. Even if it means sitting front row at a comedy show.
Paul Epstein
Hey, everyone, check out this guy and his bird. What is this, your first date?
Liberty Mutual Spokesperson
Oh, no. We help people customize and save on car insurance with Liberty Mutual together. We're married.
Paul Epstein
Me to a human, him to a bird. Yeah, the bird looks out of your league.
Liberty Mutual Spokesperson
Anyways, get a quote@libertymutual.com or with your local agent.
Paul Epstein
Liberty Liberty Liberty Liberty Discover Top Rated Stays Loved by Guests Rated Highest by Real guests through authentic reviews VRBO Book a vacation Rental Loved by Guests.
Greg Kilstrom
Hi, I'm Greg Kilstrom, host of the Agile Brand, and here's a question for you. What if your brand's success wasn't dependent on a winning product or favorable market conditions, but on your ability to connect with customers on a human level, one story at a time. Agility requires moving beyond a reliance on market trends or product performance as the primary drivers of success. It demands a deeper, more resilient connection with customers built on understanding their individual needs and stories. Today, we're going to talk about building a playbook for customer loyalty that isn't dependent on market wins or a perfect product. We're going to explore the idea that every customer has a unique story and that shifting from broad impersonal campaigns to a strategy of deep individual connection is the key to creating not just customers, but lifelong fans. Welcome to season eight of the Agile Brand Podcast. This season we're going all in on Expert Mode, MarTech, AI and Customer Experience, talking with the people and platforms behind the brands you know and love. Again, I'm your host, Greg Kilstrom, and I help Fortune 1000 companies make sense of martech, AI and marketing ops. Hit, subscribe or follow to make sure you always get the latest episodes and leave us a rating so others can find us as well. This episode is brought to you by crmc. Drive your customers to new horizons at the premier retail event of the year for retail and brand marketers. Learn more at CRMC 2026 06-01-3 www.thecrmc.com. tell me discuss this topic. I'd like to welcome Paul Epstein, CEO and founder at WinMonday and keynote speaker at CRMC, taking place June 1 through 3 in Frisco, Texas. Paul, welcome to the show.
Paul Epstein
Yeah, Fired up to be here, Greg.
Greg Kilstrom
Yeah. Looking forward to talking about this with you. Before we dive in, though, why don't you give a little background on yourself and your role at Win Monday.
Paul Epstein
Absolutely. So Win Monday is really a byproduct of a decade and a half in the pro sports world. Sadly, not the athlete. But I did spend a decade and a half in the NFL and NBA and it was all in the brand building and marketing and customer facing and sales and revenue space. And so when I speak as an example at crmc, which I could not be more fired up about, I've been in the same trenches as everybody that is attending there. And I really like to get down to this ground level of what is it in this high performance world, high achieving world like pro sports, where everybody's obsessed with success and growth and getting 1% better every day and yet you still see a separation of the elite from the rest of the pack. So I started to obsess about how do you create that separation, how do you increase your performance, your metrics, your results over time and do it in a way that's very holistic. This isn't just about work, this isn't just about career. This is about all us as human beings. And so I've studied how to win, why we win. I've studied my wins, I've studied my losses, I've studied pro athletes. I've been in those boardrooms with billion dollar goals, billion dollar pressure and billion dollar expectations. And just like in sports, typically how you start is how you finish. I believe in the game of momentum. I believe momentum drives results and those results, and I'm sure you could attest to this, Greg, the hardest thing to do in business is not just achieve a result, but create a process and system that leads to predictable, consistent and repeatable results. Like, that's the next level. So when I speak about Win Monday on the heels of a decade and a half in pro sports, I realize that we are only as good as our habits. You show me the quality of your habits, I show you the quality of your life. You show me the quality of your habits, I show you the quality of your business, of your marketing campaigns. I could keep going. So I've really isolated this down to one weekly habit that I believe can be the governor for everything else. Every single habit that we either want to build or break can plug into this singular high performance, weekly habit of winning Monday. And I'll leave you with this cool stat and then let's totally hop into this conversation. At the time that we're having this conversation, I am just. If you see some bags under the eyes, it is because any author that just finished a book and has massive bags under their eyes so that's how you know that they are an author. Okay. And so a lot. Thank you, brother. A lot of tireless nights. And I've never poured my heart and soul into any piece of work the way that I did in this Win Monday book. And so we surveyed over 50,000 people, Greg, to really understand. Because to me, Win Monday it sounds like it's about motivation and it's actually not. We'll get into what it really is about. But what we found from these 50,000 plus folks is here's the most powerful stat and this is something that we can totally lock in on when everybody listening and watching to this, You, Greg, myself, Paul, when we achieve something meaningful on a Monday, There is a 98% probability of not just motivation that day, but momentum the entire week. So imagine, Greg, if we had a process and a system and, and a habit and a framework that says you are darn near guaranteed momentum every week for the rest of your life, would you do it right? So that's really what Win Monday is all about. It's just about earning momentum every week of our career, every week of a campaign, every week of our lives.
Greg Kilstrom
Nice. Nice. Love it. Well, yeah, that's a, that's a great way to set things up here. So let's dive in here and if we're going to talk about a few, few aspects of this, but I want to start with, you know, one of the themes of your work is that every seat has a story which translates to every customer having one. In a large enterprise with millions of customers, you know, this can sound inspiring, but maybe feel impossible, you know, to achieve. How do leaders begin to instill this mindset shift at scale? You know, moving teams from a focus on mass audiences, mass segments, to a culture that values those individual customer narratives?
Paul Epstein
The short answer is there are no shortcuts. It's going to take time. It's going to take discipline, it's going to take commitment. It's going to take, how about this? We want our customers to be loyal. It's going to take internal loyalty. Internal loyalty from leaders and campaign drivers and campaign creators. This is an all in mentality from the front lines of an organization all the way to the C suite. It's not marketing's job. Yes, marketing can lead, of course, our analytics team can support, our strategy team can support, but it is an all in. Like when I, I'm cut from a sales cloth. The greatest sales results that my teams and I ever generated was not all inside of our departmental walls. It was an organizational effort. To say, you know what? When our gc, when our general counsel or our CMO is out there at a backyard cookout with their friends and family on a weekend and they strike up a conversation and somebody that they organically talk to might be a fan of the sports team, and they're like, why don't you come out to a game? They're generating leads at a backyard cookout. That's what I mean about an all in approach versus saying, ah, that's not my job. I'm in marketing, I'm a lawyer. I'm not in sales. Okay? That's company A, company B says we're all in, and they're the ones that are going to deliver better results. Okay? So coming back to every seed has a story. This was a big transformation. It actually created initially an external transformation out in the marketplace with our customers. This is how we took them into raving fans. And then after, we had a culture transformation for our team members because of the insight that I'm about to share. So the way that it works, you work at The San Francisco 49ers, where I was chief revenue officer, and we have, yes, 70,000 people in a building, 70,000 butts in seats at that particular game. But we have tens of millions of fans worldwide, some teams hundreds of millions. So you want to talk about macro? There are no bigger brands in the world than pro sports teams. I mean, it is like religion. In some places. There is a cult like following with certain brands. And because of the passion and because it really is a love hate, I throw out two words, like speaking of crmc, we're going to be in Frisco right there by Dallas. There's kind of a football team named the Cowboys there. Maybe we've heard of them.
Greg Kilstrom
I think I heard.
Paul Epstein
Speaking of a brand, when you say Dallas Cowboys, there's only two reactions, love or hate. There's no middle ground. It's a love hate, which shows you the power of a brand. So I'm at the Niners and we were getting good results. Not great good. We were ahead of goal slightly, but we felt like in the spirit of opening up Levi's Stadium in the heart of Silicon Valley, moving down from San Francisco, we wanted to be more tech forward, more progressive, more innovative. And we instituted that mindset into every single one of our behaviors and our campaigns. And so the way that this came about, we used to have blanket marketing campaigns, blanket sales campaigns, blanket customer experiences. Everything was a blanket. If you're a 49ers fan, plug into this macro Umbrella and Halo that we build, and that's it. But then we started to do what we called listening sessions. And just like you would think of a survey, a focus group, I should say, and you bring in some of your customers. We did that at a very intimate level to say when I look out at 70,000 people, because our strategy and analytics team says, what if every single one of our 70,000 fans had a unique experience? And we said, that's impossible. We very much had a fixed mindset, not a growth mindset. But then they said, well, but what if we knew more about them? What if we knew why they actually come to the game? Is it just to see the 49ers win? Would they stop coming if we lose? Have we studied that data? The truth is we didn't. We knew in general, more people want to come to games when we win, less people want to come when we lose. But yet some people have been loyal through thick and thin. Why? Is it a generational thing? Is it because their mom or dad was a fan, or is there something deeper? We didn't have the answer, so we decided to do the work. These listening sessions, we essentially asked people, what do we need to do more of? What do we need to do better? What. What do we need to do different so we don't do, start, stop, continue in my work? We do more, better, different. Then we ask them, origin story, how'd you become a Niners fan? What keeps you coming back? And we sliced and diced from our most loyal fans to the people that have dropped off, and we started to dissect that data. And Greg, I will tell you, the most heartwarming parts of my 15 year journey were being a fly on the wall in these rooms as we're listening to the stories. Hey, you know what? I was deployed for the last five years and I was serving over in Afghanistan. And the first thing that I wanted to do when I was back on US soil, I wanted to watch my team play. Hey, you know what? My wife, she just battled through breast cancer. We thought we were going to lose her. And she was almost in a terminal state, but somehow the docs worked a miracle. And the first thing she said was, I want to go watch my team. Yeah, you're thinking of education groups that are coming out that have really been given up on underprivileged communities and just salt of the earth type stories. And Greg, I'm telling you, man, this had nothing to do with football. I thought we were just going to hear people geek out about Joe Montana. And Steve Young and five super bowl rings said almost nobody. They all talked about the deeper meaning, the deeper purpose, the spirit of what it means to be. We call our fans the faithful. Why did you become faithful? What does it, what keeps you faithful? And as we unpack those stories, we said, oh my goodness, we are sitting on a gold mine of learnings here. What if we customize the experience for the person that was just serving overseas? We dedicated, we do November salute to service. We should create a VIP red carpet experience for them in the month of November because of who they are. They're not a Niners fan. They're somebody that served our country proudly overseas. They deserve a unique experience from the person that just battled through, from the person that was raised in and so that kind of every seed having a story through a lot of qualitative data, a lot of listening, a lot of learning, a lot of work to organize the data, learn from the data, deploy the data, spend money on the investments to create experiences and unique touch points. To the point, Greg, that we had a mobile app that when you walked into our building, we would know exactly who you are and what you consume and why you come. And so you would have a unique experience that would be populated through your app and we would really kind of geo fence everything. We would know who's in our building and what lights them up and. And then we would custom the experience based on that. So every seat had a story. It took about a year and a half to get there. So I'm not going to sugarcoat this. It took an organizational year and a half of just listening, no activation, just listening. So it is a long game approach which if we could have that long game discipline, it's a winning strategy. It just takes a lot of time.
Greg Kilstrom
I'm sure there's, there are some sports team marketers out there listening to the show, but there's a lot of people from other types of brands that you know at, to your point, at first blush you think, oh well, yeah, sports fans, that's just a whole different thing. And there are certainly differences. But I think when you break it down like you did, you know, by listening to your customers, regardless of what the product or service that you sell.
Paul Epstein
Absolutely.
Greg Kilstrom
You may have less passionate fans of some types of products than others. But I think to what you're saying, and please correct me if I'm wrong, but like if you listen and you find those stories and those, those origin stories, to use your, your words, there is probably something that connects people with just about any brand that they, they feel strongly about 100%.
Paul Epstein
And for those that are watching this right now, you'll see above my head, you'll see across my chest the words Win Monday. You introduced me as the CEO and founder of Win Monday. Let's, let's talk about that because I'm building a brand. I'm building a global brand and building a global mission and movement in Win Monday. That is not. On the surface, I'm very biased. I think it's the coolest thing in the world. But on the surface, it is not as sexy as a pro sports team. And I get that. So let me share a minute or two on how I'm building the Win Monday brand through a lot of the same principles and practices and processes that I learned in the very sexy world of brands and marketing campaigns like a pro sports team. So in Win Monday we have this five part cycle. It's Commitment Weekly plays, Momentum, habit growth. I'm going to break this down and apply it to as marketers, how we are leveraging the brand and our marketing ideas and our brand building ideas to drive the same level of commitment and loyalty that the San Francisco 49ers can. Starting with a place of commitment. What we have realized, Greg, is I don't care what the product or service is. I don't care what the brand is. If you don't get down to the core of your consumer meaning their identity, they have to say, I am a person that Wins Monday. I am a San Francisco 49ers fan. I am a Coke or Pepsi drinker. I whatever it is, right? What? Whatever it is, they need to talk with a sense of identity. This is who I am. This is what I stand for. This is how I show up. You, if you don't have that level of passion and commitment, then it's not an identity and they're just going to blow away with the wind. Whenever money is tight or the market conditions shift or their geography changes and they move cities, they're not going to go out of their way to consume whatever it is that we're selling or marketing because they're not committed, because it's not a part of their identity. It was convenient or it was cheap or it was affordable, not sustainable. So Commitment Weekly plays. We are very big believers that without action, nothing in the world matters. Even when I talk, if it doesn't lead to behavior change, it was not a good investment. I inspire behavior change after events because the opposite is a sugar high, you know. Greg, have you ever been to those events? Of course. Not crmc, other, others, others over the course of your career. And you go and you're so fired up like the future is so bright. And then Monday hits and then back to the inbox and back to customers and back to team and back to boss and back to spouse and kids. And then a couple weeks go by and we reflect back on an experience like an event and poof, it's a sugar high. And I had so many sugar highs when I used to attend all these events before becoming a speaker and I got sick and tired of having sugar highs. And the opposite is winning Monday. So the way that this applies for all of us is show me your customers behaviors which could be their purchasing decisions. It could be what they are doing as a result of using your product or service in their day to day business, in their day to day lives. Are we capturing that? Do we know that? Do we know what behaviors are impacted and influenced because of using our product or service? And if we don't we're missing the mark because now we can see people out in the wild. That is a massive thing. Don't see them in their polished environments. Don't look at the top 1% of their Instagram feed. Look at them on a normal day to day organic basis. What are they doing more better or different because of your product or service? So that's our weekly plays. It's a consistent execution of action and what we see is the more that people do the thing we want them to do which is benefit from our product or service, they build momentum of the benefits that our product or service delivers. So we start with commitment. We run weekly plays which is code for consistent behavior change. 98 chance of momentum. If we do these things, especially on a Monday, we don't just say do it, we tell them when we were very prescriptive. We want you to do the most important thing in your week on Monday. No guessing game. Do it on Monday because I want you to have 98 momentum or probability of momentum that week and then you'll build a habit and then you'll achieve a growth. Greg, I think one of the biggest things I learned, and I'll kick it back to you after this is, you know the reason that I used to be a leader that had high turnover. It was tough to recruit. I had culture challenges and engagement challenges inside of the teams that I was leading and then eventually I solved those problems. One of the biggest differentiators was growth. The way I defined it is when I spoke to my team I said when you go home at night versus when you drove in this morning. Did you get better today? Like, do you genuinely feel you're better when you leave than when you got here every day? And that was my internal survey and metric of success. And the people that felt that they did, they were more loyal. All of a sudden we didn't have retention issues. All of a sudden we had a better culture and engagement because they're like, Paul cares about us as a whole human being, not just as a producer. And then the market heard about it. So voila. I solved my recruiting problems too. What do you know?
Greg Kilstrom
Right?
Paul Epstein
And I think the same is true for our customers. Are we helping them get better? And if we do, do they know how they're getting better? Sometimes we need to educate the market. It's not about features and benefits in a brochure, your competitions, brochure, I joke about this all the time with colleges. Have you ever seen a crappy looking college in a brochure? They all look so amazing, like the
Greg Kilstrom
best school in the world.
Paul Epstein
There's no ugly brochures. There's none. So your brochure is pretty. Your competition's brochure is pretty. I can't tell the difference.
Greg Kilstrom
Yeah.
Paul Epstein
So unless. But what if you versus your competition is not making it about features and benefits, they're making it about transformation. I took you from here to there. You, you are going up and to the right. If you are a stock, I am helping you go up and to the right. Your life is better, your health is better, your career is better, your productivity, your efficiencies. And that's the part that I think a lot of marketers, sometimes we miss the mark. We don't highlight the transformation. We just talk about features and benefits.
Greg Kilstrom
Yeah, well, and I think along those lines, I mean, just to talk about measurement a little bit more. So I think most, most leaders, I would say most at least know where they want to get to. And you know, I think it's when you're there, you know, maybe it's easy to see that you've gotten there. You've talked about a lot of incremental measures of success from, you know, from whether it's individuals and stuff like that. But you know, these leaders, they're under so much pressure to get results tomorrow and next week and next quarter or whatever. How do you as an organization know that you're on the right path? You know, even if, even if day to day, maybe things are getting a little better. Like how do you know that you're on the right trajectory? Towards, towards those, those more ambitious goals.
Paul Epstein
Short game, long game. We'd probably all agree that the healthiest companies, the healthiest teams, the healthiest cultures, generally speaking, they're playing the long game. You know, I think, Greg, there's things business can learn from sports and sports can learn from business. My two quick hits on where I think business can improve is in the spirit of planning and in the spirit of reflection. So as an example, an NFL team scripts the first 15 plays of a game. They're prepared. When's the last time that we showed up with a script for our day, for our week, for our month? And so scripting takes time, it takes preparation, but now we show up with a more consistent level of execution. The other part is reflection. The sports analogy would be you don't just go from one game to the next blindly. No. In between games, what do you do? You watch the film, you watch the tape.
Greg Kilstrom
Right.
Paul Epstein
In business as marketers, when's the last time we watched our film? When's the last time we watched our tape? And I will say this, this is a massive gap for a lot of companies. This is a massive gap in my career too. Historically, when I was a practitioner, before I got into speaking and writing and all the stuff I'm into now, when I was in the trenches, I was not very good at the things that I just said. And I now realize that and recognize that. And lo and behold, when I got really good results or we got really good results versus bad results, those were kind of the gaps. How well did we plan? How, how well did we reflect? You know, you, we call this the Agile brand podcast, right? Like, right. I was not very agile. I was not learning and evolving and iterating. I wasn't keeping up with the world like today. It's so fast, complex, AI all the stuff. All right, well, if we're not agile, we go away, right? We go away. So, you know, coming back to short game, long game, I think there have to be measuring sticks of understanding where we are at certain milestones. I think that the long term plan, everything has to be in dark pencil, not pen. The long term plan can evolve and shift. Even at win Monday, I have the big audacious goal. It's going to sound crazy. There's going to be a day where a billion with a B, a billion people in the world win Monday. Now, I, I, that's a vision. I need a plan. I need a 30, 60, 90. I need quarterly priorities. I need annual goals. Otherwise, we're going to go out of business. And we're not going to have any direction but everything is in dark pencil. And in the last 30 days, Greg, from the time we're having this conversation, I'm sitting down with investors right now. We're in the middle of a capital raise and I will tell you right now I have learned things from potential investors which have now become actual investors. And, and I have evolved the vision and the plan and so everything is in dark pencil. What I think is important is, is the organization aligned? Because I have been in environments as a departmental leader where I felt isolated, like we were on an island. I wanted to play the long game but then I got barked at from above about short term, short term results and crack the whip and all of that and it just wasn't healthy. And yes, I know it's a bottom line business and that's where I think implementing the win Monday habit. If every short term result, if you can guarantee me weekly momentum, that's how we tackle the weekly results. But we still need to have a North Star, we still need to have a vision. So that would be my succinct answer here would be have the vision in North Star for the aspiration and so that you're always aligned to it. But let's create weekly sprints, not daily, but weekly. And if we do the most critical things that matter to our results on a Monday and we have a 98% probability of momentum the following Monday, we execute another key priority, another needle mover and we just keep treating this like weekly sprints. And that is a framework that I believe tackles both the short and the long game.
Greg Kilstrom
To your point about we want repeatable wins but you know, to the just reality that we all live in. Getting the same results often requires different approaches based on, I mean that's part of being agile, right? The world changes so quickly that do it even, even getting the same result, I mean obviously it would be great to continuously improve and iterate upwards but you know, moving forward, you know, thinking about the future, you know, you've talked a bit about this model of co creation with customers and you know, certainly you've talked a lot about listening to customers and learning from them. You know, for those brands that are, let's say they're not quite there yet, they're not quite started yet. You know what, what's a starting point to, you know, to get to this, this idea of not only continuous improvement but just being better at listening to their customers 100%.
Paul Epstein
I think there's a prequel to even listening to your customers. And it's. Have you listened to yourself? What I mean by that is, Greg, there's two types of organizations, there's two types of leaders, there's two types of performers. And the gap is. And I actually think this is the first step in leadership. And let me just disclose this. Regardless of who's listening in or watching, all leadership starts with self. Before you lead others, you must first lead yourself. That is a fact. The people that you would follow to the end of the earth and back, yes, they were probably effective at leading others, but you wouldn't follow them to the end of the earth and back if they were poor at leading themselves. Their character, their values, their consistency. You knew who you were going to get and you aspired. It was like a magnetic attraction to want to be more either with them, around them or like them and role model that behavior. I say that because my life changed after a retreat where I did a lot of that inner work. Before that I was very random, very inconsistent. There was a work Paul, a personal Paul, like depending what day you caught me in. Yeah, we were winning and growing and succeeding. But now that I look back at it, it was very inconsistent and actually it wasn't that purposeful. It wasn't. But when I did some inner work, C suite of the 49ers, we go off site, master your inner game was the name of the experience. Discover your why, your core values and know what inspires you. And then this is the beauty. We made it behavioral. I'm always going to come back to behaviors in action. We tied the, this inner stuff that we figured out about ourselves to, to our daily decisions and actions. So after going through that transformative process, I started to realize what's possible when you lift the hood of the car, what's possible when you study the engine and understand what type of, what type of fuel, what type of oil, what type of, what's the stuff that optimizes us, what's the stuff that lights us up and what's the stuff that triggers us, you know, like all this. And I really started to take a very customer focused approach in a very similar way. Yes, I largely wore a sales hat. I had a dotted line into marketing where I know a lot of our audience lives. And again, it was a very collaborative effort. And I said, how well do we know our customers from the inside out? Not just every seat as a story, but I'm talking like, have we really studied this avatar that we say that we're after? Like I know we have this high level demographic and psychographic and. But like, can we double click on that? And can we actually capture the spirit of that? So we created a big media effort. And so we collaborated with our media team and broadcast team and we started to capture film about not just their demographics or psychographics, even the infographics, it was about, let's create these life interviews and let us really capture their why. And that's where we started to uncover the transformation of our product and service. And so all that to say, not everybody has a San Francisco 49ers budget, not everybody has a media department, not everybody works in pro sports. And I want to tell you that you can do everything I just said without the flash, without it. All that it takes is put people in three buckets. Your most loyal customers. Bucket one. People that have stuck with you through thick and thin. That's bucket one. Bucket to your newer customer, somebody that's earlier in the journey with you. Bucket three, a prospective customer, but that you feel has the potential to join the tribe. Great. And you go through the same types of questions with each of them, and you look for the connective tissue. And so as an example, if a prospective customer says, I would love if somebody could help me with my abc. And. And your mature customer says, you know, your product or services, help me with A and B. Okay, that tells you a couple of things. It might tell you, maybe you. Maybe you don't go as hard on C. And maybe you, like, you find the overlap between the loyal, the new, and the perspective. And you start to communicate in a way where now you're meeting people where they are. Because everyone loves a blueprint that their fingerprints are on. Everybody wants to drive the car. They want to drive the car. In early training that I was taken through in the sales and marketing space, they said, do you know what everybody's favorite radio station is? And I was like, nope, I have no idea. And there was a metaphor. They said, it's wiifm. I said, what the heck is that? They said, what's in it for me? And they said, paul, the more that you can master the art of delivering for people, what's in it for them, you're going to succeed. I don't care what hat in the organization you wear. And it turned out to be one of the greatest and simplest truths that I ever knew. So for somebody just starting off without a lot of a budget, without a robust customer base, without a lot of influencer resources, you can always find three people to talk to and start there. The mature, the early, and the perspective. And you Just find the connective tissue, find out what's in it for them and then you quadruple down on that point versus being all things to all people.
Greg Kilstrom
Yeah. Love it. Well, Paul, thanks so much for joining today. I got a couple questions for you as we wrap up here. As I mentioned, you're giving a keynote at CRCRMC coming up June 1 through 3. What are you most looking forward to about that event?
Paul Epstein
It's the offstage conversations. It's beautiful because here's the thing, Greg, I get on pre calls, I never show up cold. I'm understanding exactly who's in the room and we want to make sure everything is delivered. Speaking of, every seat has a story. That's how I approach every keynote. Every single person, the hundreds of folks, the thousands of folks that are in a room, everybody has a story every and I want to get to know it. So yes, there's a part of a speech and it's really a conversation. It's not a speech, it's a conversation. And what it leads to right after is a lot of bear hugs, a lot of emotion, a lot of heart to heart connection, a lot of whatever I said resonating with somebody that was sitting in row 20, seat 8. And now we have this connection after that is my favorite part. Yes, let's level up in business together. But more importantly, let's just connect and, and let's stay connected for the Mondays to follow because that's really what I promised everybody at CRMC. You're walking away with a 52 week actionable playbook so that the winds keep going in your business and in your life well beyond our time together in Frisco. And that's not just my promise, but it's actually my favorite part because speaking of my core values, which I brought up earlier, my strongest value is impact and making a difference and, and leaving people in places better than I found them. And the way that I measure that is how are folks showing up for the Mondays to follow our time together in Frisco? That's what really jacks me up.
Greg Kilstrom
Love it.
Paul Epstein
Love it.
Greg Kilstrom
Well, and last question for you. What do you do to stay agile in your role and how do you find a way to do it consistently?
Paul Epstein
I need a daily process and I. So for me, if agility and being agile was the most important, I would be very intentional about it. I wouldn't leave it to chance. I wouldn't leave it up to my personality. I would leave it up to my process and my system and my habit, meaning I would journal every night. How can I show up more agile tomorrow? And I would make it behavioral and actionable. Then that populates my calendar for the next day or the way that I'm entering conversations or meetings with peers, with clients, whomever. So I have an evening and a morning routine the evening before. Journal what is most important to you and filter it through the things that are most important, such as being agile. And then I ensure that my behaviors and my actions and the way that I'm entering connections the following day I literally will put next to a calendar. I will put things on my calendar. If I have a 10am board meeting, I will put a simultaneous 10am calendar reminder that says Reminder Be agile Reminder. Like literally. I know this sounds like it's detailed work and it is because I'm not going to rely on my memory. I'm going to rely on process, system and habit. So if you want to be agile, create processes that dink. They notify you as a reminder to always be agile.
Greg Kilstrom
Yeah. Love it. Well again I'd like to thank Paul Epstein, CEO and Founder at Win Monday for joining the show. You can learn more about Paul and WinMonday and CRMC by following the links in the show notes. This episode is brought to you by crmc. Drive your customers to new horizons at the premier retail event of the year for retail and brand marketers. Learn more at CRMC 2026 G 06.01.3 www.thecrmc.com and thanks again for listening to the Agile Brand podcast. If you like the episode, hit subscribe and drop a rating so others can find the show too. And if you're interested in consulting, advisory work, or if you need a speaker for your next event, feel free to reach out. Just visit GregKilstrom.com that's G R E E G K-I H L S T R O M.com the Agile brand is produced by Missing Link, a Latina owned, strategy driven, creatively fueled production co op. From ideation to creation, they craft human connections through intelligent, engaging and informative content. Until next time, stay curious and stay agile.
Jack Welch Management Institute Announcer
The Agile Brand.
Liberty Mutual Spokesperson
And Doug there's nowhere I wouldn't go to help someone customize and save on car insurance with Liberty Mutual. Even if it means sitting front row at a comedy show.
Paul Epstein
Hey everyone, check out this guy and his bird. What is this your first date?
Liberty Mutual Spokesperson
Oh no, we help people customize and save on car insurance with Liberty Mutual together. We're married.
Paul Epstein
Me to a human, him to a bird. Yeah, the bird looks out of your league.
Liberty Mutual Spokesperson
Anyways, get a quote@libertymutual.com or with your local agent.
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Date: April 23, 2026
In this episode, host Greg Kihlström welcomes Paul Epstein, CEO and Founder of Win Monday and keynote speaker at the upcoming CRMC event. Together, they unpack the foundational strategies for building deep customer connections that transcend product performance and market conditions—focusing on human-centric loyalty, the power of individual customer stories, organizational alignment, and the actionable playbooks that drive momentum and consistency for brands.
Greg introduces the central theme: that brand success hinges less on products and more on forging human connections—understanding and honoring each customer’s unique story.
“What if your brand’s success wasn’t dependent on a winning product or favorable market conditions, but on your ability to connect with customers on a human level, one story at a time?” — Greg Kihlström (00:48)
Paul brings 15 years of experience in the NFL and NBA, where he observed that elite teams separated themselves not just with talent, but with process and momentum.
Founding Win Monday was about translating high-performance habits from sports to business, building momentum every week with repeatable, structured habits.
A key insight from Paul’s research: achieving something meaningful on a Monday leads to 98% probability of maintaining momentum the entire week.
“We are only as good as our habits. You show me the quality of your habits, I show you the quality of your life... Every single habit that we either want to build or break can plug into this singular high performance, weekly habit of winning Monday.” — Paul Epstein (03:49)
“When we achieve something meaningful on a Monday, there is a 98% probability of... momentum the entire week.” — Paul Epstein (05:56)
Paul shares the San Francisco 49ers’ cultural transformation: shifting from blanket marketing to individualized connections.
“Every seat has a story” means treating each fan/customer as unique, achieved through “listening sessions” (akin to focus groups), collecting origin stories, understanding motivations beyond the product, and using data to customize experiences.
Emphasizes organizational buy-in—it’s not just marketing’s job, but an “all in” effort from every department.
“There are no shortcuts. It’s going to take time, discipline, commitment… Internal loyalty from leaders and campaign creators. This is an all-in mentality from the front lines...to the C suite.” — Paul Epstein (06:57)
“What if we knew more about them? What if we knew why they actually come to the game? ...We are sitting on a gold mine.” — Paul Epstein (10:36)
“It took about a year and a half to get there...just listening, no activation. So, it is a long game approach.” — Paul Epstein (13:52)
Paul describes how Win Monday’s framework—commitment, weekly plays, momentum, habit, growth—applies beyond sports.
The root of loyalty is identity: “I am a Win Monday person” is what brands should strive for in their customers (e.g., "I am a 49ers fan").
The shift from product benefits to transformation—helping customers get better and demonstrating that impact.
“If you don’t get down to the core of your consumer—meaning, their identity...they’re just going to blow away with the wind.” — Paul Epstein (15:24)
“Show me your customers behaviors...Are we capturing that? ...Do we know what behaviors are impacted because of using our product or service?” — Paul Epstein (16:40)
“But what if you versus your competition is not making it about features and benefits, they’re making it about transformation.” — Paul Epstein (21:05)
Greg and Paul discuss how to measure progress toward ambitious goals, highlighting the tension between short-term demands and long-term vision.
Paul underscores the importance of planning (scripting like an NFL team) and reflection (watching the “game tape” or reviewing campaigns).
Advocates for agile weekly sprints centered on “winning Monday,” aligning both immediate action and big-picture goals.
“If we do the most critical things...on a Monday and have a 98% probability of momentum, the following Monday we execute another key priority...treating this like weekly sprints.” — Paul Epstein (25:31)
Before asking how well you listen to customers, ask how well you listen to yourself—leadership starts with inner clarity and values.
Practical blueprint: segment customers into most loyal, newer, and prospective; interview each group about their “why” and connect the dots.
Focus on “what’s in it for me?” for customers, delivering messaging and value centered on their core needs and aspirations.
“All leadership starts with self. Before you lead others, you must first lead yourself. …The people that you would follow to the end of the earth...you wouldn’t follow if they were poor at leading themselves.” — Paul Epstein (27:50)
“Everyone loves a blueprint that their fingerprints are on.” — Paul Epstein (32:21)
“The more that you can master the art of delivering for people what’s in it for them, you’re going to succeed.” — Paul Epstein (32:39)
For CRMC, Paul is most excited about “offstage conversations” and connecting personally after the talk; giving each attendee a playbook to maintain momentum well beyond the event.
“My strongest value is impact…leaving people and places better than I found them. The way I measure that is how are folks showing up for the Mondays to follow our time together in Frisco?” — Paul Epstein (34:31)
Paul reveals that agility comes from intentional process, not leaving adaptation to chance—daily journaling, setting actionable reminders, and turning intentions into behavior.
“I wouldn’t leave it to chance. I wouldn’t leave it up to my personality. I would leave it up to my process and my system and my habit.” — Paul Epstein (35:08)
“If you want to be agile, create processes that notify you as a reminder to always be agile.” — Paul Epstein (36:19)
This episode challenges marketers and business leaders to move beyond superficial campaigns and product-driven messaging. It calls for sustained, organization-wide commitment to understanding each customer as a person, building loyalty through continual listening, intentional process, and actionable systems. Through Paul Epstein’s sports-to-business playbook, listeners receive a practical, momentum-driven approach to drive both short- and long-term customer value.
Guest: [Paul Epstein, CEO & Founder, Win Monday | Keynote Speaker, CRMC]
Host: [Greg Kihlström]
Event Plug: CRMC, June 1-3, Frisco, TX – thecrmc.com