Investment is often thought of in financial terms—stocks, real estate, and business ventures. But true investment extends far beyond balance sheets and profit margins. It’s about where we place our time, energy, and resources to create meaningful impact—whether in our businesses, our personal growth, or the communities we call home.
In this special feature, we sit down with nine Naples entrepreneurs and leaders who understand the power of investing on multiple levels. From fostering local business connections and giving back to charitable causes to prioritizing health and personal development, each of these individuals shares their unique perspective on what it truly means to invest wisely. Their stories offer insight into how strategic decisions—both financial and personal—can shape not only their own success but also the future of Naples.
Alexander Deron
Tell us about your business. How do you decide where to invest within your own business—whether in new technology, hiring talent, or expansion?
I decided to invest in the people around me. Being able to recognize not only experience, but morale and culture led to a huge spike in the business we did, the recognition we gained, and the overall quality of our business.
How does your business connect with or contribute to the Naples community?
Our business is multi-faceted; We connect to the Naples community by partnering with local brands, such as Cloud9Exotics, Elite Jets & others, in order to showcase our full range of services, while highlighting other brands we love and trust.
Naples has a strong local business community. How do you engage with and give back to this community?
I am the President of the Society for Orphaned Armenian Relief, Naples Chapter. We raise tens of thousands of dollars for Orphaned Armenian children, through our Charity Galas hosted here at Naples's very own Hole In The Wall Country Club.
If you had unlimited resources, what would be your dream investment project?
I love this question! I think I would have to "stay in my lane" and invest in the rebuild of my neighborhood of Royal Harbor. I would bring in structural engineers, marine biologists, architecture firms, among other pivotal parties, and elevate the area, increase flooding protection, drainage, etc to protect our beautiful neighborhood from future Hurricanes!
Lauren Maxwell
Tell us about your business. How do you decide where to invest within your own business—whether in new technology, hiring talent, or expansion?
We are the Maxwell Team at CrossCountry Mortgage. I run my team like a business, leveraging the tools and technology CrossCountry provides. My focus is recruiting top talent and offering loan programs that other companies don't. Newly recruited Loan Officers are often amazed by the opportunities here, and I take pride in helping them expand their business.
How does your business connect with or contribute to the Naples community?
We are very active in the Naples community. We support many charities including: Make a Wish, Youth Haven, Ann's Children's Fund, Fostering Success, and the Golisano Children's Museum of Naples. We are the headline sponsor of the Legends Concert Series that honors our first responders, veterans and active military. I am also excited to announce that we are an Official Community Partner of FC Naples. My team logo will be featured on the scoreboard.
Many people consider health to be one of the best investments. How do you invest in your physical and mental well-being?
A few years ago I looked at my husband and realized that we were not active enough. We consulted a nutritionist who has helped us live a healthier lifestyle. I still work long hours, but I make more time for my family. Now that I have three Grandsons, I spend as much time with them as I can.
Looking ahead 10 years, how do you hope your investments—whether financial, personal, or community-based—will have shaped your legacy?
I am 57 years old. I have worked in the mortgage industry for 38 years. I have been building my legacy since day one. If I were to die tomorrow, I would be happy knowing that I have given my all to my family, my customers, my employees and my community. Until that day comes, I will continue my mission of helping people achieve the American Dream of Homeownership!
Daniel Kowal — Collier County Commissioner District 4
Tell us about your business. How do you decide where to invest within your own business—whether in new technology, hiring talent, or expansion?
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Being an elected official representing Collier County. My business is the people‘s business. My primary responsibility to the citizens that live within Collier County is to make sure that they have the best public safety service that we can provide. Second priority is to ensure that we keep up with the great demand of having our infrastructure built out and replacing aged infrastructure. Technology is an evolving portion of both our public safety system, and our infrastructure. When it comes to your local county government staff, we do nationwide recruiting to find the best in the industry.
How does your business connect with or contribute to the Naples community?
As a county commissioner, it is crucial that we examine projects development, infrastructure, and ensuring that the decisions we make to provide these changes to our community are constitutionally sound. Taking in consideration of developing smart with common sense goals in mind.
Many people consider health to be one of the best investments. How do you invest in your physical and mental well-being?
Coming from a military law-enforcement background, it was always important to maintain a level of physical fitness and well-being. It was a pretty basic mindset that others depended on you in their worst times. If you're physically and mentally unfit you're no help to them or your fellow first responders.
Skylar Porter
Tell us about your business. How do you decide where to invest within your own business—whether in new technology, hiring talent, or expansion?
SkyStruk Shoes is a fashion-forward footwear brand that creates bold, statement pieces designed to amplify women's confidence. The digital landscape is constantly evolving, so I always look to invest in areas that improve the customer’s online shopping experience, making it more seamless and engaging. I also focus on getting the brand out there through online advertising, influencer partnerships, and supporting local, women-driven community events. Every decision is about ensuring the brand remains vibrant, inspired by the bold spirit of my grandmother.
If you could give your younger self one piece of investing advice, what would it be?
If I could give my younger self investment advice, it would be to join an organization with stock options and a bonus plan, invest in the stock market early, and buy a house as soon as possible. These steps will help build financial stability and allow you to pursue your true passions earlier in life, without limitations.
If you had to choose one area of personal growth to invest in for the next five years, what would it be?
If I had to choose one area of personal growth to invest in for the next five years, it would be taking uninterrupted time for myself and my family, free from work distractions and social media. I want to truly enjoy the small moments of life, especially with my son Preston, and watch him grow.
If you had unlimited resources, what would be your dream investment project?
My dream investment project would be to create a foundation that empowers women entrepreneurs by providing them with the tools, mentorship, and financial backing to bring their business ideas to life. I’d also love to support a charity that helps little kids follow their dreams, giving them the opportunities and resources to pursue their passions from an early age.
Kelly Johnson
Tell us about your business. How do you decide where to invest within your own business—whether in new technology, hiring talent, or expansion?
I am in Real Estate, part of the White Horse Group powered by Alfred Robbins Realty Group which also offers decorating. We invest in our own business by holding events geared to get the word out about real estate within neighborhoods as often as we can.
How does your business connect with or contribute to the Naples community?
We like to do fun events or dancing for coffee at local coffee shops to get the word out and have fun!
How do you evaluate an investment opportunity—whether it’s in the stock market, real estate, or a local business?
If the price is in favor of the buyer and there is money to be made you have to go for it if you have the availability.
Many people consider health to be one of the best investments. How do you invest in your physical and mental well-being?
I work out 5 days a week every week to keep healthy. You have to keep moving!
If you had unlimited resources, what would be your dream investment project?
Spec homes or renovation projects to decorate how I want and show my capability.
Looking ahead 10 years, how do you hope your investments—whether financial, personal, or community-based—will have shaped your legacy?
Funds for me and my kids to thrive in retirement.
Lauren Wilmering
How does your business connect with or contribute to the Naples community?
White Horse Group is deeply rooted in the Naples community, blending luxury real estate and interior design with a passion for local connections. We support Naples businesses, engage in community events, and even bring the energy with our Dancing for Coffee pop-ups—because real estate should be as vibrant as the lifestyle we love!
If you could give your younger self one piece of investing advice, what would it be?
Just do it—no matter how you’re feeling that day or if you think the timing isn’t perfect. The best investment is the one you actually make. Waiting for the “right moment” will cost you more than taking action and learning along the way.
Many people consider health to be one of the best investments. How do you invest in your physical and mental well-being?
I invest in my health by prioritizing the things that keep me grounded and energized. Morning starts slow with a cup of coffee, setting the tone for the day. Nature walks with my dog keep me connected to the outdoors, while riding and being around horses brings a deep sense of calm and balance. I follow a carnivore diet that fuels my body, read often to keep my mind sharp, and surround myself with strong, healthy relationships with family and friends—because true wellness is a lifestyle, not just a habit.
If you had to choose one area of personal growth to invest in for the next five years, what would it be?
I’d invest in travel to expand my mind and deepen my connection to nature. Experiencing new places, cultures, and landscapes broadens my perspective and strengthens my appreciation for the world around me.
Yani Cardentey
Tell us about your business. How do you decide where to invest within your own business—whether in new technology, hiring talent, or expansion?
At Encore Title Group, we invest first and foremost in people—our clients, partners, and team. Hiring top talent ensures a seamless closing experience, while strategic technology investments enhance efficiency. Expansion is always considered, but only when it aligns with our mission of providing exceptional, relationship-driven service.
How does your business connect with or contribute to the Naples community?
We’re deeply rooted in Naples and believe in supporting the community beyond business. Whether it’s helping families secure their dream homes, partnering with local professionals, or sponsoring community initiatives, we strive to make a meaningful impact. Our goal is to be a trusted resource for all things real estate.
If you could give your younger self one piece of investing advice, what would it be?
Invest in relationships. The most valuable returns come from the people you surround yourself with, both personally and professionally. Strong connections open doors, create opportunities, and bring lasting fulfillment.
Many people consider health to be one of the best investments. How do you invest in your physical and mental well-being?
I prioritize staying active, maintaining balance, and making time for what brings me joy. Whether it's exercising, spending time with loved ones, or taking moments to reset, well-being is essential for success. A strong mindset and a healthy body fuel everything else in life.
Looking ahead 10 years, how do you hope your investments—whether financial, personal, or community-based—will have shaped your legacy?
I hope to be known for investing in people first. Whether through business, mentorship, or community involvement, I want to leave a legacy of trust, integrity, and meaningful relationships that continue to grow and inspire others.
Doug Chey
Tell us about your business. How do you decide where to invest within your own business—whether in new technology, hiring talent, or expansion?
Fast Lane Drive is a members-only networking group and car club in Naples. Roaming the roads and coastal lines of Southwest Florida, we believe networking, philanthropy, and a love for luxury automobiles can unite people for a meaningful cause. Our exclusive social club comprises entrepreneurs, executives, dedicated philanthropists, and aficionados of fine automobiles who unite with a shared objective: to converge and revel in the marvels of automotive engineering in an exhilarating and enjoyable manner. The Naples chapter of Fast Lane Drive is only eight months old, but we have grown very quickly from a membership and partnership perspective. We are part of the worldwide Fast Lane Drive community (with chapters in San Diego, Chicago, Monaco, etc.), and we leverage technology and support from headquarters. Right now, we are entirely focused on membership and sponsorship growth.
How do you evaluate an investment opportunity—whether it’s in the stock market, real estate, or a local business?
The answer to that question has changed through the years. As I get older, I am getting more conservative in my investment philosophy. I look for good core fundamentals and leading indicators that show positive growth.
If you had to choose one area of personal growth to invest in for the next five years, what would it be?
Getting out of my comfort zone and entering my growth zone. As Eleanor Roosevelt once said “The purpose of life, after all, is to live it, to taste experience to the utmost, to reach out eagerly and without fear for newer and richer experience.” I need to get out there more. Life is short!
Bill Beynon
If you could give your younger self one piece of investing advice, what would it be?
Start early and develop a disciplined plan for saving and investing. I would focus my investments on the long term.
How do you evaluate an investment opportunity—whether it’s in the stock market, real estate, or a local business?
We take a risk-based approach when evaluating any investment. Risk, return, and liquidity are important to understand when making any investment.
Many people consider health to be one of the best investments. How do you invest in your physical and mental well-being?
After my father passed away suddenly when I was a teenager, I began prioritizing my health—exercising daily, staying proactive with preventive care, and keeping up with regular checkups and screenings.
Naples has a strong local business community. How do you engage with and give back to this community?
One of the things we love about Naples is the collaboration within our peer group and the broader community. Giving back is a core value for us, and we feel a strong responsibility to support the communities where we work.
Our philanthropic efforts focus on education, homeless, hunger relief, veterans, and medical advancements. Our two primary initiatives are the Naples Children’s Education Foundation (NCEF), where my wife, Nena, and I serve as Trustees, helping fund children’s initiatives in Collier County, and the CWA Annual Turkey Drop (cwaturkeydrop.com), our largest corporate philanthropic endeavor, which we started 20 years ago and now feeds 6,000 families in Southwest Florida every Thanksgiving.
In addition to these efforts, our advisors and employees actively support various charities, including veterans’ organizations like Home Base and Warrior Health Foundation, as well as local schools and other community initiatives.