Tracks To Success
Kraig Kann, a veteran golf broadcaster and former C-Suite sports executive turned business entrepreneur, hosts the top podcast that brings you inspiring people and their inspiring success stories. How did they find their way to the top? How can their path help you do the same? As a speaker, consultant, author and leadership workshop facilitator himself, Kraig has a high energy fun chat with other top leaders and top personalities from all walks and all professions and gives his guests the platform to share untold stories about their rise up the ranks. On "Tracks to Success" you'll hear from big time names and names ready to hit the big time in a 5-star podcast you don't want to miss.
Tracks To Success
Mike Flaskey
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🎙️ Tracks To Success | Mike Flaskey: Building Brands, Creating Experiences & Leading What’s Next
What does it take to transform major organizations, lead iconic hospitality brands and create experiences people never forget?
In this episode of Tracks To Success, Kraig Kann sits down with Mike Flaskey, President and Chief Operating Officer of Marriott Vacations Worldwide, for a conversation about leadership, innovation, reinvention and the power of turning big ideas into real experiences. Mike stepped into his current role in February 2026 after more than 25 years of leadership across the hospitality and vacation ownership industries.
His career has included more than a decade at Diamond Resorts International, where he ultimately served as CEO and led the company through significant growth and transformation before its sale to Hilton Grand Vacations. He later founded his own sports and entertainment company and served as CEO of Hornblower Group before returning to the vacation ownership industry with Marriott Vacations Worldwide.
But Mike’s story is about much more than titles.
It’s about seeing what could be better—and doing something about it.
Kraig and Mike talk about building cultures that encourage innovation, creating customer experiences that become true brand differentiators, developing people, navigating major career transitions and having the confidence to keep moving forward when the next opportunity doesn’t look exactly like the last one.
In this episode, you’ll hear about:
• The leadership philosophy behind Mike’s career
• Transforming Diamond Resorts and leading through major growth
• Why memorable experiences create powerful brands
• Turning ideas into action instead of waiting for permission
• What innovation looks like inside a large organization
• Reinvention, setbacks and knowing when it’s time for something new
• Building teams that see opportunity instead of limitation
• Mike’s return to the vacation ownership industry with Marriott Vacations Worldwide
• How his definition of success has evolved along the way
Mike Flaskey has built a career by refusing to simply accept the way things have always been done.
His message for anyone looking to get ahead?
Don’t just identify what could be better. Be willing to help make it better.
It’s a conversation about leadership, experience, innovation and continuing to build what comes next.
🎧 Listen to this episode of Tracks To Success with Kraig Kann—and subscribe On Kraig's YouTube channel for more inspiring stories from leaders, entrepreneurs, visionaries and changemakers.
Watch Tracks To Success on Kraig Kann's YouTube Channel!
Hi everybody, right now on this all-new edition of Tracks to Success. What does it take to transform major organizations, lead iconic hospitality brands, and create experiences people never forget? We'll find out. As CEO of Diamond Resorts, he helped drive growth and lead the company through a major transformation and sale. But his story didn't stop. He launched his own sports and entertainment company, led Hornblower Group, and now has returned to the vacation ownership industry as president and chief operating officer of Marriott Vacations Worldwide. His name is Mike Blaski, a builder, a proven leader, and a believer that great brands don't simply deliver a product, they deliver an experience. His journey of success starts now.
SPEAKER_00Welcome to Tracks to Success, the podcast that introduces you to inspiring people with inspiring stories. It's your chance to hear from top leaders, entrepreneurs, visionaries, and change makers as they share how they found their way to the top and how their journey can help you find your own. And now here's your host, former network broadcaster, C-suite executive, best-selling author, and keynote speaker, Craig Kahn.
SPEAKER_01Mike, thanks so much for joining me. It's great to see you. It's great to hear you. Um, you've built this incredible career across hospitality, vacation ownership. I know we're gonna get into sports and all the other stuff. Maybe how you and I've done a few things together, but it's great to see you. Thanks for doing this.
SPEAKER_02Hey, Craig, it's always a pleasure to be with you, my friend. I am honored to be here today. Thank you for having me.
SPEAKER_01Well, you're gonna make Tracks to Success a whole lot better. Let's start with this new chapter, Marriott Vacation. All right, worldwide. That's a big deal for you. Um, what made it the right move for you to come do this?
SPEAKER_02Look, I mean, at this point in my career, I've had probably 25 plus years in the vacation ownership space. And, you know, we were very, very, very excited when we had the opportunity to sell Diamond Resorts to Hilton. And I got out of the business for a few years. And I was leading a marine transportation company. My buddy Matt Averill called, they brought him off the board, you know, went to the bullpen, as we say, brought him in as the the CEO, and he needed some help. And we have a deep history together. And I thought it was just the perfect opportunity with the perfect set of brands.
SPEAKER_01So the fact that somebody calls you, and and I'm gonna kind of go off script here a little bit because I think it's interesting, and I think it can help people who are listening or watching this. Somebody calls you, you've built this great resume. That is really how it works. It's who you know and what people remember of the impact you've made that helps you continue to have opportunities. Is that fair?
SPEAKER_02It's very fair. And, you know, look, it all begins and ends with having great people around you. And I've been blessed throughout my career. I guess if I if I have a gift, it's around people and making sure that I know my strengths, I know my opportunities, and trying to make sure that I have the right people in those spots to backfill me. And with that, we've had a lot of great success. And so, yeah, that's right. You know, you have that success, you put those blinders on and you go do it. And then eventually you wake up one day and you've got that track record, and people look at that.
SPEAKER_01So President and Chief Operating Officer, that's a pretty big title. It's a lot of responsibility. I know you're charged with doing some things that are going to be really special for the entire organization. How do you define success in that role? What will ultimately be a success for Mike Flaske?
SPEAKER_02Well, look, I mean, the the role requires, you know, full accountability with everything, the customer, from the top of the funnel to the brand, to the digital, you know, throughout the traditional marketing, throughout the timeshare marketing, throughout the timeshare sales, to the customer service, all the way to the customer advocacy. So my whole mission here is to elevate the customer journey, to increase the lifetime value proposition so that our owners stay and enjoy their ownership longer. Here at Mariette, they already are in the system significantly longer than most of the other companies because of the power of the affinity of our brands. But what we're focused on is really all about the customer and all about creating experiences.
SPEAKER_01So how do you honor, because Marriott is such a big brand with such a rich history, how do you honor the past and then push the organization forward, respecting that past?
SPEAKER_02It's a great question. I mean, we're really blessed here at um Marriott Vacations Worldwide. Uh the chairman of our board is Bill Shaw as an example. You know, Bill served for you know 30 plus years as CFO, president of Marriott International. Um, he and Bill Marriott are, you know, continue to be very, very close. He's very close with the family. And, you know, having Bill on our board and really being able to shed some of the light uh in the heritage and the history of the company is really cool. And so, you know, I had the opportunity from the early days when they reached out, you know, to have Bill as a resource. And I've really utilized Bill, you know, being, if you will, an outsider coming into a company with you know decades and decades of history. Um, I would say that's been a cool part of it.
SPEAKER_01Let's um let's go back. And and I want to kind of you talk about the customer journey. I want to talk about your journey, um, a little bit of the background before the titles of CEO and all the transactions and different things you've done to help lift, elevate, if you will, companies. What were you pursuing early in your career? What what was it? I mean, if we went back to limestone university, if we went back to high school, when we went back to when you were, you know, a teenager, did you see all this coming?
SPEAKER_02Oh, no, no, no, not even close. Um, you know, look, I I would tell you a couple of things, and we can get into it as little or as deep as you want, but sports had a significant positive impact on me personally and my career. I came out of a small town called Manio, North Carolina. It's a little small island in the northeastern corner of North Carolina that had a rich heritage in sports. And, you know, I was blessed athletically, had the chance to go play in college. And so I would tell you, I it's funny because I I saw my very first resume that I ever created about six weeks ago. We were going through some boxes and it and it turned up. And, you know, I was looking for an opportunity to coach, I was looking for an opportunity to scout, I was looking for an opportunity, you know, to teach. I'm a physical education major. And so, no, I I never saw all this executive level stuff coming, but it all goes back to sports and having the opportunity to play for great leaders and honestly play for leaders that weren't very good, too, because sometimes some of the greatest lessons are what not to do.
SPEAKER_01Yeah, I would agree with that. You just said coach, scout, teach. Um, that's really what any leader does. I mean, you're scouting great talent, you're coaching them up, um, you're a mentor. So, your experience, if we can go into that, spans sales, it spans marketing, it's big on brand, operations, resort management. We go on and on. How important was it for you, Mike? Like as you look back to have an understanding of the business from so many different angles?
SPEAKER_02Well, and that is the key, right? I started as once I knew that my baseball career was done, once I knew I couldn't play at the big league level, I at least had enough sense. I scouted for a few years to try to hang around and rehab, but I had enough sense to get out of there so I didn't wake up at 40 and really have nothing but minor league baseball and scouting on my background. And I went into sales. And I'll never forget I moved from the Outer Banks of North Carolina in 1992, August of 1992. I moved up to Williamsburg, Virginia, and I started as a salesperson. So I learned the product from the tables, interacting with the customers, you know, on a day-to-day basis. And then from there, my my coaching background and my scouting background, the first leadership opportunity I was offered, I moved to Nashville, Tennessee in 1996. And that role was head of recruiting and training. So I would spend a week recruiting and staffing and building the next training class. Then I would spend a week teaching the curriculum. Then I would spend the next week recruiting, the next week training. And so that's how I kind of got started. And then over the years, you know, I had responsibility for operations. Um, I had responsibility as I moved up in the organization for different things, mergers and acquisitions. Um, you know, and you just gain that experience from the inside out.
SPEAKER_01From premium golf headwear to standout apparel and accessories, Ahead has built its reputation on quality, creativity, fast delivery, and taking care of its customers. They've never been content to follow trends. They've built a brand by setting them. If you're looking for gear that helps you look your best on and off the golf course, visit AheadUSAShop.com and don't forget to use the code TTS30. That's TTS30 to receive 30% off your personal order. Ahead, premium headwear, apparel, and accessories, and the official headwear of the Tracks to Success Podcast. We're talking with Mike Flasky, President, COO, Marriott Vacations Worldwide. Um, you just said some some really interesting things a moment ago. Um, what advice would you give people given the fact that you didn't know you were going to end up with roles like you've had at the very top of organizations and you were feeling like sports might be your thing? I mean, there's so many little curves and and pivots and stuff along the way. What would you tell people or what do you tell people?
SPEAKER_02Well, I think that at the top of the list would be persistence. Um, you know, look, I was a uh all the way back to sports, you know, I was a little bit undersized in football. Um, you know, I was a I was a tick slow to play center field at the professional level, had to move to the corner. So I couldn't really hit 25 home runs with a wooden bat, but I was persistent. I wanted to play, I had a desire to compete. And so as I got into my career, you know, and and and opportunities came up, a lot of times I was not the first choice, which meant I had to take opportunities that the first choice didn't want. And so I was willing to take some risk. I was willing to take opportunities to take on things that other people thought may have been too big of a challenge, which to put it back into sports terms, I was like, put me in, coach. I'm ready, right? And so I got those opportunities. Maybe I was the second choice, maybe I was the third choice, but I made the most of them. And over time, I kind of earned this kind of label, you know, as the fix it guy. And now the smart people have rebranded it transformation. So I guess I'm a transformation guy.
SPEAKER_01I like that. Um, tell me more about the childhood, real quick. Um, who were the influencers? Was it your parents? Um, did they they give you a nudge to say, hey, Mike, um, you gotta go a different direction, or or you did you do that all on your own? What about that career growth spurt from a parental side?
SPEAKER_02So look, I I grew up with a single mom, and my mom was the ran the midnight shift at the local 7-Eleven in Manio, North Carolina. So I had to figure it out and I had to make money. I didn't have the jog boat to go duck hunting, I didn't have the waiters that everybody else had to go do the things we love to do, the hunting and fishing. I had to go make money. So I started charter fishing in the summer of my fifth grade. Um, and I did that all the way through high school. And I ran into was employed by a gentleman by the name of Captain Alan Foreman. And he was a huge influence on my life from about the fifth or sixth grade until really after college. And Alan owned a boat called the Crystal Dawn, and I eventually he taught me into getting my captain's license. I came back, I ran that boat, you know, after I've got out of baseball. And so I learned a lot from him. But I would say the most influential person in my career was the Hall of Fame great right-handed pitcher, Gaylord Perry. Gaylord recruited me. He saw me in summer school at a junior college. I helped work his baseball camp as a thank you. He would always throw BP after the camp, you know, to the people, the kids that were working the camp. I was a freshman in college. I, you know, I could hit a little bit. He saw that. We hit it off. And so he ended up taking the head coaching job at Limestone University a year or so later. And he called me and offered me an opportunity to come down, play center field for him. I did that for three years. And uh, you know, playing for a Hall of Famer, man, there's so many great lessons. And, you know, Gaylord was uh what I would say in the business world, what we would teach. He's uncont he was unconsciously competent. He was great. He wasn't a technical guy, but what he was was he could read every person on the roster, and he knew whether to put his arm around one person and take them down the tunnel and have a conversation with them. And he knew whether the guy over there needed to be kicked in the ass in front of the whole club and everything in between. And those were some of the greatest leadership lessons one could ever get.
SPEAKER_01Love that. Love that. Let's let's stay on the leadership side of this. Um, you've had a pretty real cool climb in my book, and I I do know about the sports background for you. What did the climb teach you about, let's say, earning the right to be a leader? Absolutely. Maybe Gaylord Perry helped you with that, but but what have you learned along the way about earning that right?
SPEAKER_02Well, it's not given, right? I mean, you know, first off, just to get an opportunity in leadership, you have to go do what, you know, you're supposed to be doing in the current role. And I think what a lot of people do is a lot of people get distracted. You know, I jokingly talk to, you know, young executives and I say, you know, when you go to a cocktail party and you're having a conversation with somebody, don't be that person whose eyes go over their shoulder to see if there's a bigger fish in the room to talk to. Stay locked in on what you're supposed to be doing. Keep your blinders on. And I think if you take care of your business, right, whatever level you're at, whatever your role and responsibility is, if you take care of the business and be the best you can be at that, somebody's gonna notice you, right? And when they notice you, it's exactly what you just said. You have now earned the right for that next opportunity. So when you get in that role, people will respect you, even though it may be a stretch and it may be a step up, you know, in leadership. You will have come from a place where you had a lot of success. People know that. And at the end of the day, they may say, he or she doesn't have a ton of experience in what they just got promoted into, but you can't deny what they did and where they came from.
SPEAKER_01Yeah. Yeah, that's interesting. I um I in my workshops talk a lot about um people at leadership levels um and how they are viewed. Most people don't pay attention to a leader when everything's going great. But when things are challenging or when something goes wrong, all eyes are on them to see how they react, to see how they handle it, to see how they they make others feel calm under that type of pressure. You talked earlier about um Diamond Resorts and the sale to Hilton Grand Vacations, and you've been moving along the way. When that happened, when that big sale was going on, um talk about your leadership there and the level of transformation. I'm going back to that word you used, without losing people along the way, because there's uncertainty there. And people are looking at you to make sure that everything's cool. How did that work?
SPEAKER_02Look, that that's a great example, Craig. Um, and and I'll digress just a second so that the viewers really have a you know an understanding of what I inherited when I was asked to become the CEO of Diamond Resorts. Diamond Resorts was a publicly traded company. In fact, it was Marriott Vacations and Diamond Resorts. And for 13 consecutive quarters, we hit it out of the ballpark. And there was an article that was written in the New York Times that talked about overly aggressive sales practices, um, maybe overselling to older customers. And that created a scenario where the stock dropped from about $45 down to about $17 or $18 a share. And the board decided that they wanted to run a process and sell the company. And so I at that time was the chief sales and marketing officer, myself, our CFO, and our president and CEO, we ran that process. We sold the business to Apollo, one of the two largest private equity companies in the world. Apollo came in and they decided to make leadership changes. They came to me and asked me to take over as CEO. And my job was transforming this company that had this now stigma attached to it because of this article that was written. Now, history proved out that the article was hogwashed. We had 38% of our free float that, you know, had been invaded by short sellers, and they had gotten to the New York Times, and you know, it was a hatchet job. And looking back, everybody now understands that that wasn't true. But I had the responsibility of taking a company that was once flying high that had been knocked down here, had been sold, had been taken private, and transforming that company. And so you're absolutely right. I mean, everybody was looking at us, the media was looking at us, you know, the markets were looking at us. I mean, we had over a billion dollars in publicly traded bond debt. Our bondholders were looking at us. You know, we had at that time 12,000 team members. They're looking at it. And so over time, what we had to do was we had to re-establish the credibility. We had to be innovative. We had to be different. We had to be better because we didn't have a Merrick brand. We didn't have a Hilton brand. We didn't have a Disney brand. But yet we were competing with them. And so we figured out a way to position ourselves as an independently branded company and go do some innovative things that ultimately revolutionize the industry. And so that really was both a great example of your question about how all eyes are on leaders and how you transform a company, but is also an example, you know, about how you have to go sometimes when the going gets tough as the leader, and you have to lead from the front. And that's what we did there.
SPEAKER_00In addition to hosting this podcast, Craig leads the Cannes Advisory Group, empowering companies and individuals to elevate communication and build brand awareness with bold ideas, lasting impact, and his signature green shoe style. From company consulting and team workshops to one-on-one coaching and transformational virtual programs, Can Advisory guides people to communicate with greater clarity, confidence, and input. So whether you're a leader looking to give your team a game-changing one-day experience or an individual who wants to become a speaker and presenter, people remember, visit CanAdvisory.com. And when you connect, mention the Tracks to Success podcast to receive a special discount on Can Advisory Services. That's CanAdvisory.com. Now, back to the interview.
SPEAKER_01Talking with Mike Flaske, he leads Mariette Vacations worldwide. And I want to focus on exactly what you were just talking about a moment ago. Um, there are a lot of brands out there, and I've had the opportunity, uh, full disclosure for our listeners and our viewers to work with you and to help your teams. And in my workshops that you've seen, you know, we talk a lot about, and I learned a lot from you that day as well, and many of those days, but talking about differentiation, okay? And so you just you just went through a lot of different things about these different brands. And I remember a lot of your people when we were working on messaging and they were working on their messaging, I'm saying, okay, we got to be more specific more specific. And because everybody can say they got great culture. Everybody can say that they find great properties that great value. All right. But But there has to be something different. And you're a big experiences guy. So when you talk about transformation and what you were able to do, take us through that. What was your big thing that you tried to pass on to all your people that was so valuable?
SPEAKER_02Well, earlier in the show, we talked about, or I talked about the value proposition, you know, kind of the customer journey and lifetime value, right? And our product is a subscription product. Okay. And what I mean by that is the vacation ownership industry, people buy their vacation. Here at Marriott Vacations, we have over 700,000 families that trust us with their vacation. And they pay an annual taxes, uh, you know, insurance. It's called an annual maintenance fee to own their product. And so we want them to have a great experience, and we want the value proposition to exceed what the perception of what they pay for the product is. So back in the days of the independent brand world, we created what we called events of a lifetime. And it was an experiential platform that had live music, it had culinary, uh, it had sports and entertainment, it had television entertainment, and we curated and created these headline shows for the owners. And you say, well, what do you mean? Well, the owner comes on vacation, they own their vacation product, their focus the entire time they've owned the product, 10, 12 years, has been on that corner unit overlooking the ocean in Maui. And that's what their view of their vacation was. Well, what we did was we curated this headline show with a Cole Swindell or a Lee Bryce or a Travis Tritt or a headline, you know, celebrity chef. And all of a sudden they show up on their week of vacation and they have an opportunity to see and attend one of these great shows that they didn't bargain for, they didn't pay for, and they didn't know they were gonna get. So now all of a sudden they go see Cole Swindell and they go back and they tell their kids, man, you wouldn't believe this. It was the most unbelievable thing. And the kids are like, wait, Cole Swindell performed on property in Maui? And they're like, Yeah, it was the most unbelievable show. We didn't even know about it. Well, is there a website? Oh, yeah, there's a website we can go to. The company's curated several hundred of these, and we're now planning our vacations around these shows. When the next thing you know, they tell their grandkids, and the grandkids are like, wait, what? Colts Wendell? So now the kids want to come on vacation, the grandkids want to come on vacation. And so grandma and grandpa are looking at each other, going, This is the greatest thing we've ever done. Look at this, the whole family wants to come. And why? Because now we create an experience that money can't buy while they're on vacation.
SPEAKER_01It's really cool. By the way, Cole Swindell's been on this podcast. Has he? He was really good. Okay. Um, I want to I want to focus on that for a second. How do you teach an organization then that the customer experience, which you just talked about, it's not a department, right? You don't have this experience department. It's really a responsibility that's shared by everybody. Like, how do you get all of your people on board with that to walk day by day by day? Experience, experience, experience.
SPEAKER_02Well, it's a culture. Let's start there, right? And it it starts at the top with me because I eat, sleep, and drink it because I'm so passionate about it. And so our executive team at Marriott Vacations is now immersed in it. They now understand it. We actually just launched our experience platform here at Marriott Vacations on June 22nd. Um, and we call it Inner Circle, presented by AFLAC. And we had our very first show in Orlando, and it was country music superstar Lee Bryce. It was incredible. Uh, we've now had our second show, and what we're doing, to your point, is we're doing a soft launch in 2026, and we're going to do about 50 of them between now and the end of the year. And we're not looking for a proof of concept to see if the experiential headline shows work. We know they work. What we're looking to do is we're looking to get our Marriott associates basically ingrained and immersed in the culture of what it takes to execute one of these shows flawlessly. And it starts with the marketing team. It starts with the owner services team promoting it, it starts with the timeshare marketing team, getting the owners accustomed to understanding what these shows are and wanting to attend them while they're on vacation. It goes to the resort general managers and the staff underneath he or she so that they make sure they partner with our production team to set everything up on site. And then it ends with our sales and our marketing teams that go out and they execute it. So what we're doing between now and the end of 26 is we're getting our staff and our associates here at Marriott Vacations acclimated, and then in 27, we're going to roll hundreds of these things out across the enterprise.
SPEAKER_01Would you say that the brand is a logo or is it the people?
SPEAKER_02Well, it's a great question. It's both, but more than a logo, what it is, is it's a promise. It's a promise to the consumer that for nearly a hundred years the Marriott brand has been there, has done what it said it was gonna do, has stood the test of every possible market downturn, every possible scenario that can happen over those decades. And the customer has an affinity to these brands because they know there's a promise that the brand is gonna do what the brand says it's gonna do. And so there's that element, but it's the associates and the people behind it that bring it all to life.
SPEAKER_01I know you've got a great team. So how do you make sure that all the people that you just talked about, you know, back channel, understand the true importance, the real value that they bring, the importance of their role in executing all this and bringing it to life? I mean, it's one thing to say we do experiences, it's one thing to put it on paper, it's one thing to put it on marketing sheets and all that, but you got to bring it to life. How do you make sure as a leader that your people understand they might not think they're that big, but man, they're really big. They play a big role.
SPEAKER_02Well, I'll go back to the concept of something we talked about very early in the show, and that's team. And fortunately, I have been able to hire an amazing team. And fortunately, that team was the same team that revolutionized this entire industry at Diamond Resorts, where, you know, they were the first team to create these experiences. And of course, now Hilton Grand Vacations has taken it and they have, you know, cross-pollinated it into their enterprise. And so this team works tirelessly to educate and train and develop the Marriott Associates on what you really have to do to be successful. And then, in addition to that, the team that was here, the Merriott Associates, educate that team on what it means to have the power of the Marriott, the Weston, the Sheraton, the Rich Carleton, the St. Regis brands, the Hyatt brands to power these experiences. See, that's nothing that, or rather, that's something that we never had in our past life. We never had that brand bar of those powerful brands. And boy, when you know how to do it like our team knows how to do it, and then you bolt the power of those brands that I just mentioned on there, it's like a rocket ship.
SPEAKER_00Looking for a guest speaker for your next event or annual conference, Craig brings an inspiring and empowering message your audience won't soon forget. Visit Craigcanspeak.com to learn more and hear what audiences are saying about the green shoe experience making an impact at events across the country. That's Craigcanspeak.com. And when you connect, mention the Tracks to Success podcast to receive a special discount on your event with Craig. Now, back to the show.
SPEAKER_01Mike Flasky is my guest. Uh, he has zero passion for his job and zero energy, as you can tell, um, talking about his job. Um, I I I admire that, man. It is so great to hear that type of energy, and that's what people are always looking for from a leader. I want to I want to take you back after Diamond Resorts, okay? You stepped into this world of maritime hospitality, CEO of Hornblower Group. I don't think many people necessarily know what that is, um, but you brought your experiences to the water, if you will. What did that chapter, or maybe the chapter of transition, do for you? I want to I want to focus on you. Um, and what did it teach you that you've brought into this new role that you've got now?
SPEAKER_02Well, it taught me a lot. You know, anytime you can expand your horizons and you can go into a different industry in a place that you um, you know, have really never been before, certainly at the CEO level, um, there are a ton of learnings. And, you know, the hornblower uh phase uh opportunity was a great opportunity. You know, the when you when you sell a company, you have this thing called a non-compete. And in my case, uh, you know, Hilton kept adding the non-compete. They paid handsomely for it, they didn't want me to compete with them. Great. So I stayed on the sideline. And there were very few things I could do in the world of hospitality. So, you know, we had a small little company uh called MF Entertainment, Mike Flasky Entertainment, and you know, we were doing some really great experiences. And the folks at Cornferry saw that, they knew what they wanted to create at Hornblower. There was a new private equity company that had purchased uh Hornblower, and they had a business unit called City Cruises, which is a really cool little business. It's a dinner cruise business where they take people in all the major metropolitan areas that have water, um, and they do these dinner cruises, these two or three hour dinner cruises. And so we added an element, we created what was called City Cruises Live, which has just been an amazing hit for them. And it was something that we injected into that brand that took off like wildfire. And so I was challenged, as you asked the question on a personal basis. I was challenged to make sure that I had the opportunity to go in and learn a business that I had never learned before and I had never done before. And, you know, that that business required me to learn the maritime hospitality. It required me to learn the safety element, it required me, you know, to work with a new private equity group. It required me, frankly, to take a business that had been very challenged and create an LRP, a three-year plan that could get them on the right uh right track to ultimately grow and and then be able to sell that business. And that was the, you know, that was the marching order. So I learned a ton. Uh, it was a very fast-paced environment. And look, um, you know, Matt Averill called uh when the phone rang and they asked him to go on the board at you know, Marath Vacations. And when he called, uh, I raised my hand and I said, you know what, this is an opportunity to go back into a business that I've been in for over 25 years. Uh, I came back in this business um with a newfound appreciation and energy, having worked for my second private equity company, uh, which is, you know, frankly, some of the smartest people in the world. I grew as a leader and came back, you know, with really what I call a soup to nuts value creation plan of a company that had been a wildly successful company that had started struggling and it needed a transformation. So these private equity companies taught me how to create these plans to basically go out and transform these companies, create these value creation plans. So I'd say that was the biggest takeaway in what we've brought back here to Marriott Vacations.
SPEAKER_01I would say, Mike, presence is a gift. Not everybody has that. Um, you're a front and center guy. I I follow social media for your company, I follow it for you. And you're out there, not just with your team, you're out there with your customers, um, your partners, you're out there with the people that provide those experiences, you're in the media, um, you're on podiums, you're on panels. Do you enjoy that part of the job?
SPEAKER_02I do enjoy that part of the job. Uh, and I and I think I have a responsibility, um, A, because I have a gift in that area, but B, um, I think it puts you in a position where you can't hide behind trees. And what do you mean by that? What I mean by that is I'm pretty easy to find. Okay. If a customer has an issue, you can find me. You can send me a direct message, uh, you can email me. Uh, and you know what? I personally respond to those customers within 24 hours. And, you know, we get on it. And our team and our organization sees that. So they engage at a higher level with the customers because of that. The customers see that. They appreciate having access, you know, to the people at the top of an organization. But at the heart of it, Craig, uh, I will tell you it's all about building a team. And what I mean by that is this I was probably the first CEO, I was the first CEO in the vacation ownership space that embraced social media. And people told me I was crazy, but they also told me I was crazy when I put my business card at all 120 hotels and resorts that we had across the world in 34 countries at Diamond Resorts. But I didn't care because I wanted the owner to call me. Because if the owner calls me and the owner reaches out to me, then I know I got a general manager that ultimately didn't want that to happen. And they're going to go above and beyond to make sure next time that owner reaches out to them and not me. Okay. So by putting myself out there and by creating this platform, the recruiting world, we own it. We own it. I mean, the whole world, they don't answer me publicly because they may be employed at a competitor. They don't go out and put themselves out there. But let me tell you, the direct messages I get from executives that work for our competitors, it's mind-blowing. And that is where they have that platform to reach out to me confidentially and say, you know, it's just not quite going the way we thought. You got an amazing track record. You know, it usually ends really well for all the team members. I'd like to have a conversation with you. And because of that, we become the employer of choice, all because of the things you talk about.
SPEAKER_01Employer of choice. Interesting, uh, interesting thought process there. And and um I I understand this. I'm very fortunate to work with some really great leaders and some CEOs. And um one of the things that gets discussed quite often is statistics and data and numbers and shares and stockholders and all that stuff is just information. What we talk about a lot, and it's a buzzword now, is storytelling. And stories travel, those stats just sit there, okay? But stories around those things where we can make people feel something, that's different. Is there something in your career, a story perhaps, a defining moment? Because I think those are really big, that changed everything for you in your career?
SPEAKER_02That's a great question. Yes. I and I'm gonna tell you the story. It's a it's it's a it's a humbling one to tell, but I'll tell it. Uh 1986. I am playing baseball. I'm a freshman at Chihuan Junior College in Murfreesboro, North Carolina. I told you earlier that Gaylord Perry had a uh summer baseball camp. I was there that summer. I worked at baseball camp. I met Gaylord Perry. I chose at the end of that year, I had a great year, made made all conference, uh, started as a freshman, but I didn't take care of business in the classroom. Uh I had other interests. I had one foot, one foot back at home thinking about making money, charter fishing. Uh, I loved the baseball part of it, wasn't really committed at that time to the classroom part of it. And I made the decision after a great freshman year to go back to my hometown, buy a boat. And that fall, I started working on that boat to get ready to go charter fish that summer. I was a captain, I'd made a lot of money, and that was my path. And I'll never forget on Christmas Eve, I had gone out to dinner. There were no cell phones at that time, or at least we didn't have enough money to have one. And I got home in about midnight, and uh, there was a note laying next to the phone. It was an old rotor dialer phone. And the note from my mom said, Gaylord Perry called and wants you to call him tomorrow. He understands it's Christmas Day, but he'd appreciate the call. So the next day I picked up the phone. I called Gaylord. I said, Hey Gaylord, Mike Flaske, how are you doing? He said, Hey, Mike, buddy, good to hear from you. He said, I want to give you some great news. I took the head coaching job at a small school in South Carolina called Limestone University. And he said, I'd love to fly you, your mom, your grandmom out as soon as we get through the holidays. I'd love you to come in. I'm building my team. We're going to start in the fall of next fall. We got this spring. We're going to work on building the team. I would see you as my center fielder, as a captain to help me not only on the field, but help me build this program. And he said, I'd really like you to fly out here. And I said, uh, well, Mr. Perry, I said, what an honor to have somebody like you call. I said, you know, I'd love to love to come play center field for you. I made a decision to kind of leave baseball and go back to my hometown. Um I bought a charter boat. I'm going to start charter fishing this summer, got my own business. And I said, so, you know, as much as I'd love to play baseball, and as much as I miss baseball, and I know I could come be a great player for you. Honestly, I don't know that I could get into school. I said, because I didn't take care of business in the classroom. And he said, son, he said, did I ask you if you could get in school or did I ask you if you want to come play center field for me? I said, you asked me if I want to play center field. He said, I'll handle the rest. The tickets are in the mail. And so we ended up going out, my mom, my grandmom, and I, we flew out to Gaffney, South Carolina after New Year's. Uh, met with Gaylord again. I met him earlier that summer or summer before at the camp. Gaylord showed me around, painted division. I got a full scholarship. I was, I was really, I think, one of only a couple, if not the only, person on the team. Usually baseball has partial scholarships. I had a full scholarship, and uh, it was an opportunity that changed my life because I knew then that I couldn't let Gaylord down. I always knew I had the ability to play. There was no question on the field. Um, it was really just about applying myself, and it was about really being serious about the academic side of it. And I knew I couldn't let Gaylord down, I knew I couldn't let my grandmom down, knew I couldn't let my mom down. So, you know, in 1990, you know, I became the first person in my family to ever graduate from college. So I would say that was the story, you know.
SPEAKER_01That's a great story. A great story. And and by the way, if I can I can uh you know go off of the captain of the boat, the experienced captain doesn't become experienced in calm waters, right? Do it with some choppy seas and and you've had some of that. Um winding this thing down here with a couple final questions. You know, I would say experiences is attached to you, right? That if we're marketing Mike Flasky, that's what you bring to the table. I talk a lot in my workshops um and keynotes about being sticky and being memorable. You know, we have a job, we gotta we gotta make people remember what they're supposed to remember. That's the message. But we also gotta make sure that we make people remember that we were the one that told them what they were supposed to remember. We got to become memorable. What makes you sticky?
SPEAKER_02Well, that's a great question. Um well, at the core in leadership, we're only as good as the people we have around us, right? And for 30 years, I believe I have done everything I said I was gonna do. And I believe that I have always taken care of my people, and my people have been rewarded both in career growth, uh They have been warded economically. And I think that they, you know, have have been rewarded, you know, mentally from a sense of team, a sense of culture, a sense of growth. So I think being sticky begins and ends with doing what you say you're going to do. And, you know, it comes down to people ask me all the time, you know, even back when, you know, I was in my little company at MF Entertainment, they say, man, how in the world do you get all these celebrities and all these artists and all these sports people to come play in your events? And I said, Well, because I've always done what I said I was going to do, I never ask them for anything extra. I don't want anything. I just want to really show them a great time. And I think when you do that, it becomes sticky.
SPEAKER_01I'm going to give you an opportunity for two messages. Um, one is for people out there who want to be you, who want to be a leader of an organization. That's their dream. Um what should they be focused on as they build before they become focused on the title? What advice would you give them?
SPEAKER_02Look, I always go back to my sports background when people ask me this question, Craig. And I think, you know, your preparation, right? If you're a pitcher, if you're a hitter, if you're a quarterback, you know, game day's game day, right? And nothing happens in game day that you didn't prepare for before game day, because you have to go into the game and you have to have had enough repetition to become unconsciously competent. You can't be thinking when you're at the plate and somebody's throwing 94 miles an hour. You have to react. So the work that you did in the cage, the work that you did throwing bullpins, the work that you did, you know, throughout the week to get ready for game day on Saturday or Sunday if you're playing football, that's the most important thing. Because if you're prepared and if you're ready, when the lights come on, you just go out and you react. And it's the same thing in business, same thing in business. You have to be ready, you have to put that work in. So that would be, you know, kind of the advice I would give somebody that was, you know, kind of looking to, you know, hopefully one day aspire to be a great leader.
SPEAKER_01I'm gonna ask you this as well. And uh, there are probably a lot of people, if we're being honest, they're like, oh, timeshare. Now you've always called it vacation ownership. Um, I remember that. That was sticky to me. Um share. Oh, I don't want to get into that. But at the same time, you got all these customers, a lot of people having great experiences being a part of Marriott Vacations worldwide. And then there's some other people that they may be thinking, maybe this is for me. What's your message? What's on the horizon for the industry? And what's on the horizon for those people who are already loyal to Marriott Vacations worldwide under your leadership? What are they going to see? What do you want to tell them?
SPEAKER_02Well, I'll tell you this. I'll start with the industry. Uh, the industry is at an all-time high when it comes to growth. Uh, they did nearly $11 billion in sales in 2025. And what even makes that more powerful is only 6% of the eligible households in North America own the product. So the runway and the history of this great industry is tremendous. I'll tell you very quickly, you know, uh I grew up with a single mom. I already said she worked at the 7-Eleven. Um, we would have never been able to take vacations but for a great product like this. Because my mom was able to afford this product, she could do it on a monthly payment basis. The product allowed her to lock in the cost of vacations at today's dollars and buy a product that she could take us on vacation every summer and show us a great time that she would never ever have been able to afford. And it was at places that we would never ever have been able to step foot into these great resorts. So the product is a tremendous product. When people buy this product, the the you know, customer survey scores are in the 90-plus percentile. I mean, they're always in the low to mid-90s. People love this product. What we're gonna do, and what my promise to the 700,000 families who have purchased their ownership at Marriott Vacations worldwide, is we're gonna continue to enhance that customer journey. We're going to make sure that we're responsive to the customer and owner needs. We're gonna make sure that that on-site experience continues to be elevated. We're gonna elevate the experience. Craig, does that sound familiar? And we're gonna make sure that by introducing experiences that we're gonna give them things they didn't bargain for. And with that, you know, we hope that they'll tell their friends and that others will come, you know, make sure that they check out the great brands we have here at Mary on Vacations.
SPEAKER_01Well, maybe I'll get you coming in to uh to one of my elevate workshops. Um, I I really appreciate um your time. I appreciate the storytelling. I appreciate the candidness that that you share. And um I I think it seems like there's a lot of great things on the horizon. I know what uh experiential ownership is all about because I've seen it through your eyes. Let's make a deal. You you can come hand out a few green shoes with me somewhere. Uh, that'd be a lot of fun.
SPEAKER_02Well, listen, I'd be honored to do that because I have worked with you in the past and many times. And uh, you know, look, it's one thing to, you know, to hire a professional like you, you know, to come in and do an amazing seminar, you know, for your executives. And, you know, you leave and people say, oh man, that was great. And, you know, they forget about it or they don't forget about it, they implement things. But the true test of greatness, and I can honestly say with you, it happened, are the people that raised their hand confidentially one-on-one and hired you as their personal coach, and that depended on you to help them with their personal growth. And those executives that saw you in that seminar environment, but took it upon themselves to follow up, to hire you to be their coach. I have seen them grow. I have seen them, I have seen them be rewarded for making that decision. And I have to tell you, the LV experience is real, and you're the power behind it, Craig. So thank you.
SPEAKER_01No, it means a lot. I appreciate that a lot. Appreciate you and um experiences is a word I hope everybody takes from this today, and also innovation because you're that guy as well. Mike Flaske, thanks so much, and and congratulations on your success, your track, your journey. A lot of people will benefit from it. Thank you all.
SPEAKER_02I enjoyed it.
SPEAKER_01One last segment I call Getting Ahead, which is focused on you and your own tracks to success. It's brought to you by Ahead, the finest in headwear and the official headwear of the Tracks to Success podcast. Available at aheadusap.com. For listeners of this show, Ahead is giving one of its biggest discounts ever. Visit aheadusap.com now and use the code TTS30. That's TTS30 and receive not 20% off your purchase, but 30%. Ahead. They don't follow the trends. For more than 30 years, they've been setting them. Well, I hope you enjoyed the interview with Mike, and it is time for getting ahead. Let's talk about innovation and the opportunity to create it from wherever you are. Now, Mike Flasky's career is a reminder that innovation isn't reserved for the person with the biggest title, the largest budget, or the corner office. It starts with actually seeing something differently. It's noticing what could be better, what could move faster, and what could bring more value, then having the courage to bring that idea forward. Too often, people wait for permission to innovate. They wait for a promotion, a new role, or somebody else to invite them into a big conversation. But the people who actually get ahead don't simply wait for the opportunity, they create it. So being innovative in your role doesn't always mean developing the next big product or completely reinventing the business. Sometimes it means improving a process, solving a customer problem, strengthening your team, or maybe finding a better way to communicate an idea. Innovation is actually a mindset before it ever becomes a result. So here's my challenge. Are you simply completing the responsibilities in your job description? Or are you expanding the value of the role? So guess what? I'm actually going to give you permission to turn those ideas into action. Become an innovator. Look for the gap. Bring the idea. If you do that consistently in your career, the tracks to success become a whole lot easier. Hope you enjoyed the interview. Until next time, I'm Craig Cann. Thanks for joining me.
SPEAKER_00Don't forget to subscribe for more great interviews and Craig's insights on reaching your highest personal and professional summit. Listen to Tracks to Success on all the top podcast platforms. Watch it on the Craig Cannes YouTube channel, and visit CraigCanspeak.com to learn more about Craig as your next speaker.
