How Diamond Resorts’ Mike Flaskey Intends to Make ‘Vacations for Life’ a Reality

Mike Flaskey

Maybe being Chief Executive Officer of Diamond Resorts International® isn’t Mike Flaskey’s first rodeo, but it promises to be one of his most exciting. After more than 20 years of senior leadership experience in vacation ownership, including holding senior executive roles with Starwood Vacation Ownership and Fairfield Resorts (now Wyndham Vacation Ownership) before taking over as Executive VP of Sales and Marketing, North America, for Diamond Resorts in 2010 and later moving up to Executive VP and Chief Sales and Marketing Officer in 2014, Flaskey is now in charge of the whole enchilada. Diamond Resorts International® manages vacation ownership resorts and sells vacation ownership points that provide members and owners with access to approximately 420 managed and affiliated properties and cruise itineraries.

In order to compete with the brands, he explains that Diamond Resorts’ vision is to offer consumers an original and compelling slate of attractions and benefits. In rapid-fire staccato, Flaskey explains a number of initiatives that Diamond Resorts has launched, including (among others) forging ambassadorial alliances with world-famous musicians, Hall of Famers from Major League Baseball, Super Bowl MVPs, NASCAR legends and PGA, LPGA and PGA Tour Champions stars.

He has lent his visionary leadership to enhancing Diamond Resorts’ philanthropic endeavors. For instance, he is the Founder and Executive Director of the Diamond Resorts Invitational™, a nationally-televised, PGA Tour Champions-sanctioned professional-celebrity golf tournament. The tournament has a strong philanthropic arm and has raised nearly 2.3 million in charitable dollars for Florida Hospital for Children.

The Trades sat down to ask him a few questions. His answers were not entirely what we were expecting; they spurred a lot more enthusiasm and excitement than you typically get from a timeshare industry CEO. Let’s see what you think:

TRADES: What are the top three priorities you are addressing as CEO for the remainder of 2017?

FLASKEY: My first mandate is to continue to lead innovation and growth. This is extremely important to our bond holders, owners and our team members. Secondly, we’ll be continuing to work on improving customer service. We just introduced Diamond Clarity™, a national program that formalizes a series of new and existing customer enhancements that define how the company engages with current and future members during the sales and closing process, setting a new standard in our industry.

Another top priority is recruiting the brightest talent available to Diamond Resorts. We have incredible mentorship programs. We take college grads and put them into an apprenticeship program to develop the next generation of senior leaders. We are focused wholeheartedly on seeking the best-in-class, most talented candidates.

TRADES: What about the long-term? What can you tell us about your plans for, say, the coming five-to-ten years?

FLASKEY: We will be taking a look at the product to see how it fits with the needs and preferences of millennials. We’re also seeking to grow by expanding our brand globally.

TRADES: How about innovative ideas? What does Diamond Resorts bring to the table that’s unique, would you say? And what else might be on the drawing board?

FLASKEY: We pride ourselves on innovation. To be successful, we have to be on the cutting edge since we don’t have the benefit of a hotel brand. Because we need to continually look for ways to compete, we create intriguing products that will be inspirational to customers. Just to give an example, we created a program called Events of a Lifetime®. These are more than 3,000 experiential special events that are presented around the globe. They cover every imaginable interest including concerts, culinary demonstrations, helicopter rides, VIP treatment at extraordinary receptions, premiere seats at high-profile sporting events and wine tastings, to name a few. Members have been able to enjoy personally meeting with such sports figures as baseball legend Reggie Jackson, Super Bowl XXVI MVP quarterback Mark Rypien and eleven-time PGA Tour winner John Cook.

We are always looking to create new benefits for Diamond Resorts members, such as our point of sale merchandising program, ‘Diamond Luxury Shopping.’ Or, there’s our Concert Series. These are nearly 50 private concerts presented exclusively for our members and are held at resorts throughout the States. Coming up this summer are concerts with Cole Swindell, Jana Kramer (whom you may have seen on Dancing with The Stars) and Colt Ford. The concerts are presented at various venues including poolside locations so that members can have a meet-and-greet and then watch the show.
We are working on presenting a Culinary Event series with celebrity chefs that travel to resorts throughout the network. Another members-only program we’ve launched is our Member Adventures where members can experience a once-in-a-lifetime trip such as hiking the Kilimanjaro, visiting the Great Wall of China and so forth, just by being part of THE Club®.

TRADES: What are your plans for growth in the near and long-term future?

FLASKEY: Even if there were more definite acquisitions to come, I’m really not at liberty to address the topic. I can say, ‘Look at our history where nine companies were acquired very quickly.’ I believe we have become quite adept at integrating new resorts into the parent company. Of course, we’re always looking for opportunities. We are also managing to grow organically, too, as we work diligently daily on new marketing channels to draw new members. Our team has done a great job of expanding our network.

TRADES: Does Diamond Resorts anticipate adding any new products or services in the near future?

FLASKEY: We are always in the laboratory. We have a team that considers new options, daily. We add to current programs and look for additional opportunities. We have the most creative and brightest people working on development every day.

TRADES: At the end of each day, what brings you the greatest sense of satisfaction as CEO of Diamond Resorts?

FLASKEY: Without hesitation, I can say it’s the letters and emails we receive from the half-million-plus families who own at Diamond Resorts. For example, earlier this week a family sent six pictures of their vacation to Ka’anapali Beach Club in Maui. They’d been going there every year for the past 20 years. One of the photos of their daughter was taken at the resort when she was three years old. Now, she is twenty-three. So, she recreated the exact same pose and we had a shot of her twenty years later. Knowing your work has contributed to their lifetime of memories is very satisfying. You know you’re doing a great thing; you’re running a good business.

I’m also proud of the many philanthropic things we do across the system. For example, the Diamond Resorts Invitational™ golf tournament held in Kissimmee over the past five years has provided Florida Hospital for Children with $2.3 million; from these proceeds, they purchased equipment that has enabled them to become a top epilepsy center in the world.


Currently, the Company delivers memorable vacation experiences to members, owners, and guests worldwide. Flaskey’s objective is pretty clear: continued growth and expansion so that even more families can enjoy ‘Vacations for Life®.’ Running the Diamond Resorts operation from top to bottom to make this happen may be a tall order. But, Flaskey brings plenty of charisma, intellect and enough energy to light the Las Vegas Strip. Our guess is, he’s the right guy for the job.