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Steve Case, Chairman and Majority Owner of Exclusive Resorts, is not one to look in the rearview mirror. Yet as The Club commemorates its 20th anniversary, he credits travel with Exclusive Resorts as playing a pivotal role in his desire to continually impact our future.

Steve Case may be the ultimate multitasker. He impacts our collective day-to-day life, considering his role as co-founder of America Online (AOL) in 1985. Fast-forward to today and his entrepreneurial spirit continues to impact society via a variety of roles, including Co-Chairman and Majority Owner of Exclusive Resorts.

How does he do it all? Travel, he credits, is key to his creativity and expanding perspective. He acquired Exclusive Resorts in 2004, and when he first learned of The Club, his intention was simply to join as a Member, yet akin to most all his successful ventures, he quickly identified both need and opportunity: a missing link in the travel industry for those who wanted to forgo the commitment of second or third home ownership and instead continually travel to new places, and with like-minded individuals.

He also found personal growth through The Club. What began nearly 20 years ago as an alternative to the hassles and headaches of managing a portfolio of second homes has evolved into a way of life. As his family grows (he recently welcomed his fourth grandchild), he cherishes The Club all the more, today employing his membership for multi-generational family vacations and unique experiences — he and his wife, Jean, are looking forward to a second Around the World expedition with Club partner National Geographic. He also uses The Club as a remote office; he finished edits on his latest book, The Rise of the Rest: How Entrepreneurs in Surprising Places are Building the New American Dream, while traveling.

As The Club celebrates a major milestone year, Case reveals his travel industry predictions, where he most likes to escape to, and the makings of a pioneering spirit.

After your success co-founding AOL, Exclusive Resorts was your next big investment. Why are you so passionate about travel?

There’s something about traveling and the experience of meeting different people and exploring different cultures, be it with family or friends. The level of interaction is different than everyday life. When I learned about Exclusive Resorts, I thought, ‘That’s the way’ — the alternative to owning a home. And when I initially contacted The Club, it was to be a Member, but the more I engaged, I realized there was something special happening and that’s when I also became an investor.

What do you see most impacting the travel industry two decades from now?

How do you give very busy people time to be with their families and unique and even magical experiences? That’s going to be driving innovation in the travel industry. One of the big mega-trends is working while traveling. Exclusive Resorts has always been well positioned for this — the benefit of homes with multiple rooms, plus the confidence in our technology makes it easier to work while traveling than most other options.

Which Club destinations do you find yourself returning to most often?

The variety of options at Exclusive Resorts is terrific, so you’re not always going to the same place. I remember visiting our flagship in Peninsula Papagayo, Costa Rica, almost 20 years ago and found it magical. Back then, Costa Rica felt like Hawaii. And Hawaii is another favorite because that’s where I’m from. The Club has many residences on several islands. Miraval Arizona is a favorite, too — Jean and I return frequently, but we also like the variety of trying new places.

Do you find your creativity sparked in a different way when traveling?

Traveling allows time — to take a step back and look at what you have been working on in a different context. It’s certainly helpful to be disconnected from everyday life and really focus on ideas.

Speaking of ideas, The Club has been celebrating the concept of "life's too short for should haves." What is key to your continued success and your drive to always be pushing the needle forward?

I’m sure a lot of Exclusive Resorts Members don’t spend a lot of time thinking about the past, instead spending more time leaning into the future. Which doesn’t mean you don’t want to remember great experiences or learn from mistakes. I’ve always had the mindset — maybe even to a fault — of focusing on what’s next. I try to imagine what the future might be like, and then think about how I can play a role in helping to make that possible, whether it be four decades ago with the early days of the Internet, 20 years ago when I got involved with Exclusive Resorts, or 10 years ago when I started working on The Rise of the Rest — to have more companies and cities creating more jobs, hope, and opportunity. It’s about saying, ‘What might it look like in the future?’ And then based on that, you put concrete steps in place: ‘Here’s where I am, and here’s where I want to go.’ It may take a long time, it may be frustrating, and you know they’ll be setbacks. But you know it’s a mountain worth climbing.”

How do you feel about this milestone 20th anniversary year?

It’s amazing. What was an idea 20 years ago is now a significant company with a wonderful group of Members and properties all around the world. It has shifted from being about vacation but now to a broader context, in terms of not only spending time with family and friends but even in how we work. Jean and I spend more time at Exclusive Resorts homes than we did five years ago because you can work on the run, with more flexibility of where from. Plus, in less than three years our family has grown with additional grandchildren, which will make Exclusive Resorts and the way we can travel with The Club even more enticing.

In celebration of the 20th, if you were to give yourself advice 20 years ago, what would you have said?

I try to do a lot of things that have a positive impact. Sometimes I just need to slow down — I tell myself that now and I would tell myself then. I want to keep having a significant impact, trying to make the world a better place, yet I also want to maintain balance and other priorities like family and travel.

What's next for you?

I’ve been in various cities to talk about the book, The Rise of the Rest, but it’s also a way of bringing communities together. I also chair the Smithsonian Institution, which has 21 museums and a lot of research operations, all of which are playing a pivotal role in America’s 250th birthday in four years. At Revolution, we’re making a lot of investments across many different sectors. Scaling that takes time, so even though I said I should slow down, I may have the best of intentions but not be so good on the execution — someday!

What tops your travel wish list?

I’d like to spend more time in Asia and Latin America. My wife, Jean, chairs the National Geographic Society, a partner with Exclusive Resorts, and we’re doing several different things right now, including an Around the World trip. We did that once years ago, and it will be fun to experience something like that again.

What is your vision of Exclusive Resorts' relationship with its Members?

Continuing to build on the legacy of the last 20 years and have Members feel this really is a Club and a community. Building on the existing platform, we want to continue to give Members additional residences and additional experiences. You can count on Exclusive Resorts to ensure that whether traveling with loved ones or working while traveling, you’re always going to be delighted by the experience.