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The Future Of Travel: “A focus on experiences and more meaningful memories” With Mike Flaskey, CEO of Diamond Resorts & Candice Georgiadice

We’ve recognized that travelers’ desires are changing and we’re developing these innovative products to meet their needs. People want experiences and more meaningful memories. As part of my series about “exciting developments in the travel industry over the next five years”, I had the pleasure of interviewing Mike Flaskey, CEO of Diamond Resorts. Mike has […]


We’ve recognized that travelers’ desires are changing and we’re developing these innovative products to meet their needs. People want experiences and more meaningful memories.


As part of my series about “exciting developments in the travel industry over the next five years”, I had the pleasure of interviewing Mike Flaskey, CEO of Diamond Resorts. Mike has more than 20 years of senior leadership experience in public and privately held companies, with a key focus on growth-oriented companies within the vacation ownership industry. He previously held the position of executive vice president and chief sales and marketing officer for Diamond Resorts from 2014 to 2016, and executive vice president of sales and marketing, North America for Diamond Resorts from 2010 to 2014. Throughout Flaskey’s tenure at Diamond Resorts, the company has achieved unprecedented growth both organically and through strategic acquisition integration.


Thank you so much for joining us Mike. Can you tell us a story about what brought you to this specific career path?

I honestly thought I would end up playing baseball my whole life. That was my goal, anyway. After graduating from Limestone College in Gaffney, South Carolina with a physical education degree, I went back to my hometown in North Carolina to coach my high school baseball team. I then worked as a professional scout for the Montreal Expos and still thought about maybe one day signing to play in the big league. While that didn’t happen, my father-in-law, who worked in vacation ownership for years, recognized that many of the skills I learned through coaching and baseball would apply to this industry. I look back now and think about how blessed I was to have the opportunities I did. There are many things that I learned on the athletic field that I apply every day in my current role.

What do you think makes your company stand out? Can you share a story?

We have the best team members and continue to attract top talent because of our thriving company culture that not only inspires, but rewards innovation. With products like our Events of a Lifetime experiential vacation platform, our team is continuously moving the needle and solidifying Diamond as a leader in the vacation ownership industry. When we launched Events of a Lifetime in 2013, we held just a handful of special events in select markets. Last year, we held more than 3,000, including nearly 100 private concerts with our Diamond Celebrity ambassadors such as Dan + Shay, Cole Swindell, Lee Brice and Lee Ann Womack. We have nearly two dozen Diamond Celebrity ambassadors ranging from country music stars to baseball legends and golf professionals, and what they do is hold exclusive events for our members to create once-in-a-lifetime vacation experiences. For example, last fall country singer-songwriter Lauren Alaina performed a sold out show at Madison Square Garden in New York one night and the next evening she was in Orlando meeting and performing for about 150 of our members. That’s an intimate experience our members can only get with Diamond.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”? Can you share a story about that?

At Diamond Resorts, we always remind our members to break from their routines and take time out for the people and things that matter most in life. As a vacation company, it’s so important that we don’t forget that ourselves. I make it a point to remind our team members to schedule their vacations and enjoy their time away. We say vacations aren’t a luxury — they’re a necessity. Use vacations as your time to relax, recharge and reconnect.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

I had the privilege of playing for baseball Hall of Famer Gaylord Perry during my time at Limestone College, and one thing he did was take the time to get to know of all his players as individuals. He would understand them on a personal level to see beyond their baseball abilities and recognize what made them so great as individuals. That really stuck with me and is something I apply every day in my role. It is crucial for leaders to take the time to recognize their team members and understand them, so you can help them succeed. I am so grateful Gaylord showed me that so early on in my career.

Let’s jump to the core of our discussion. Can you share with our readers about the innovations that you are bringing to the travel and hospitality industries?

As millennial travel behavior has redefined the traditional vacation experience, we’ve revised how we market and cater to this generation. Over the past several years, we’ve observed an increase in our millennial membership, leading us to subsequently test a new 10-year product, “Introductions”, that affords members greater flexibility.

Our Events of a Lifetime platform remains incredibly popular, and we continue to enhance it every year, adding new concerts, private events and celebrity ambassadors. It’s unmatched in the industry. This year, we also created a new golf tournament, the Diamond Resorts Tournament of Champions, as our premiere event with opportunities for members to meet LPGA champions and celebrities. We recognize the importance of innovation and are quick to adapt to meet the changing desires of our members and guests. In addition, we also understand that how we deliver these experiences matters. This past year, we looked at different venues, including House of Blues in Orlando and The Foundry at SLS Las Vegas, to provide our members with an even better, unique concert experience.

This year, we also launched a new monthly payment plan program to allow some of our members to pay their annual maintenance fees in monthly installments instead of one lump sum, which is the industry standard. The maintenance fee bills come out in December, around the holidays, and we realized it can be tough for members to pay the fees all at once. We piloted the program with a group in 2018 and received positive feedback, so we are excited to see how many members take advantage of it this year.

Which “pain point” are you trying to address by introducing this innovation?

We’ve recognized that travelers’ desires are changing and we’re developing these innovative products to meet their needs. People want experiences and more meaningful memories. Our Events of a Lifetime platform offers both of those, and our teams are constantly searching for ways to enhance the platform and ensure we’re keeping up with what consumers want.

How do you envision that this might disrupt the status quo?

Our goal with testing these new membership products and experiential programs is to appeal to the next generation of buyers. We’re disrupting the outdated idea that a timeshare is a week in the same unit at the same time each year. We are making vacation ownership fun and doing that by showcasing benefits beyond just resort stays.

Can you share 5 examples of how travel and hospitality companies will be adjusting over the next five years to the new ways that consumers like to travel?

  1. Adding more exclusive, once-in-a-lifetime vacation experiences. Our concerts are a perfect example of this, as they’re experiences you can’t get anywhere else.
  2. Increasing exceptional customer service. Customer service is a top priority for our team members, and we are careful to add personal touches whenever possible, such as sending a bottle of champagne to a couple on an anniversary trip or leaving a handwritten note for guests celebrating a birthday.
  3. Incorporating technology throughout the travel process. We’re testing online concierge services that let members book excursions through our Diamond app and mobile check out, so guests don’t have to talk with someone if they don’t want to.
  4. Offering a variety of ways to travel. Our members can use their vacation ownership points for an adventure to Mount Everest or to climb Mount Kilimanjaro. They can also book traditional resort stays, cruises or flights on select airlines. We’re expanding how members can see and experience more on vacation.
  5. Expanding destination options. We’re always looking for new partnerships to expand our network of vacation destinations, so our members can see more of the world.

You are a “travel insider”. How would you describe your “perfect vacation experience”?

People sometimes think that a “perfect vacation” has to be a once-in-a-lifetime trip, but that’s not always true. What makes a vacation perfect are the lifelong memories you make. Whether you’re at a favorite resort that you visit every year or exploring somewhere new, if you’re relaxing and reconnecting with what matters most to you, that will always be the best experience.

Can you share with our readers how have you used your success to bring goodness to the world?

Giving back is one of the key tenets of our brand. It is what makes our company so special and what helps strengthen our Diamond family culture of helping one another and the communities we call home. We regularly offer volunteer opportunities for team members and support local organizations. Charity is also a main pillar of our annual golf tournament, which was an official LPGA Tour event in 2019. Since we launched the tournament in 2013, we’ve raised more than $3.1 million. I’m so proud that our teams continue to make charity a priority — not just during the golf tournament — but all year long.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

Spreading the word that vacations aren’t a luxury — they’re a necessity, and making sure everyone has an opportunity to take time away for what really matters in life.

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