Discover the captivating tales of Naples, Florida's extraordinary women who shape the heartbeat of our community. From trailblazing entrepreneurs to powerhouse mothers and compassionate leaders, City Lifestyle Naples celebrates their resilience, innovation, and profound impact. Join us as we unveil the inspiring narratives of Naples' dynamic women, each sharing a unique story of strength, success, and community engagement in our coastal paradise.
RAEGAN GILLETTE
Tell us about yourself.
I was born and raised in Clearwater, Florida as the oldest child of five. Growing up in a big family, I quickly developed patience, strong communication and social skills, and a competitive nature. After graduating from Stetson University in 2010, I moved to NYC where I began my career at Live Nation Entertainment within Media & Sponsorship. After spending 8 years in the city, the pandemic hit, and I knew it was time to get back to my Florida roots. I moved to Naples and was blessed with transitioning my role at Live Nation as Senior Brand Director, Custom Events & Hospitality Vertical Lead to full-time remote. In addition to my role at Live Nation, I also sit as a Board Member on United Arts Collier.
Who are some other women you admire?
My sister, Vanessa Gillette, is someone who inspires me (whether she knows it or not). A few years back she took a big risk, leaving her full-time job and starting her own health and nutrition company with her (now) husband. Fast forward, they are KILLING it, and I couldn’t be prouder to call her my sister.
I have been blessed with meeting countless influential women in music – both talent and leaders – that have inspired me to keep going and be 100% authentic to myself along the way.
What motivates you?
My biggest motivator comes from my job, in that I get to curate once-in-a-lifetime experiences for fans. Being a part of that is beyond fulfilling. And furthermore, getting to share what I do with those most important to me – family and friends – is truly magical.
MARY BRANDT
Mary Brandt proprietor of Hotel Escalante and restaurant Veranda E located in downtown Naples and also The MED restaurant in Bayshore Arts District. Mary is the proud mother of two wonderful daughters, Emry (20) and Allie (14).
Mary was President of CIGNA Healthcare in Indiana before entering the hospitality industry. She has an undergraduate in Nursing and a degree in Health Sciences. She grew up in Van Wert, Ohio and had lived or extensively worked in Kansas, California, Georgia, Puerto Rico, Louisiana, and Indiana prior to making her home in Naples.
Mary is the sole owner of The Escalante, referenced by many as “Naples’ hidden gem.”
Her biggest challenges include moving from a corporate healthcare position into hotel ownership — a hotel that was previously in bankruptcy — in a new town, with a 10 month old baby in arms! Mary says, “You must learn fast on how to manage all the balls in the air and bring on the best team of people to be successful.”
Mary believes that the most important things in life are a strong family, gratitude, health, and learning from your mistakes. Mary’s passions have always been children, healthcare, and to make a difference in other people's lives.
When it comes to a work-life balance, she shares “Balancing personal and professional is easy because it seems like they are one. It never feels like work!”
Mary hopes that her daughters and all young women believe in themselves, that they can achieve their dreams, and most importantly, have inner joy and peace in their lives.
RANDY FIFIELD
Randy April Fifield is the founder and Chairwoman of Randy Fifield Modern Living. For over 30 years, she has been a senior executive in multi-family housing, creating lifestyle brands that live, work, and play in over 10 cities. Her expertise has enhanced multiple portfolios totaling over $7 billion in market value.
How do you define success?
Success is wanting and appreciating what you already have! It’s the precious present; you cannot change your past and the future is not guaranteed.
What do you enjoy doing in your leisure time?
I am really lucky because I love my business and it fills my bucket in leisure time too! Since moving to Florida, I have completed 6 real estate projects in 4 different sub-markets. When I am not working, I love to travel with my kids and friends and collect art. I have a cavalier King Charles named Luke and we walk everywhere. Like everyone in Naples, I am crazy for pickleball and bike rides. I also like to visit Urban Meditation on 5th Avenue to stay grounded and balanced.
What advice would you give to other women?
Your life will be bigger than you can imagine! Life is not made of grand slams or get rich quick schemes. Simple steps like continuing to get to first base and around the bases slowly bring success. Have a plan and set goals. Be a diligent worker and a diligent saver. Know where the puck is going and plan accordingly. Do things right the first time!
Have your own lawyer. Keep your money in your name. Invest in real estate when you're young and don’t be afraid to make mistakes … they are some of the only ways you will learn and you can truly call them your own.
PAT DODGE
What is most important to you in life?
My wonderful family and friends are what have always been most important to me in my life. Having loving parents, fabulous brothers and of course, the loves of my life...my two sons, David and Greg, I have been blessed with the warmth of a wonderful caring family. Having the love of my husband Jack in my later years has been a very special gift. I am so grateful for each of them. In addition to my family, my friends have always been a very special and an important part of my life. Each of them, my lifelong friends as well as my new friends have made my life richer. They have enriched my life and made life more enjoyable.
What initiatives or projects are you currently involved in, and why are they important?
I am currently serving on the board of the Sarasota Opera Guild. Once I retired and moved to Florida, I knew that I wanted to contribute to my new community in some way. Since the arts are very much a part of Sarasota, and I have always loved the arts....this was what I chose to do. The Opera Guild's mission is to raise funds for the Sarasota Opera, assist young singers, to help increase opera attendance and promote the Opera. I find this involvement rewarding, interesting and a wonderful way to meet great people and to feel a part of our new community.
How do you balance your professional responsibilities with your personal life?
I was under the impression that once retired there would be nothing but leisure time....that is not what has happened! Our calendar is full with friends, SILLS, Opera Guild, book club, tennis, travel etc. Life is good and we are so grateful for our good health and the ability to enjoy every day. Well almost every day!
JESSICA ZAZO
Tell us about yourself.
My husband Chris Zazo and I own Hailstone Vineyards, a boutique winery located in Napa Valley, California. We share our time between there and Naples with our two fur babies, Dutton and Ainsley!
What are some of the biggest challenges you’ve faced in your career?
Marrying into the wine business and having to learn all that goes into it. Taxes, compliance, bottling, labeling, shipping etc. I don't think many people quite understand all that goes into making wine. I sure didn't!
What is most important to you in life?
I’m so lucky to have my family near me here in Naples. I value spending quality time with them and our wonderful group of friends. While I love having a career that keeps me occupied and engaged, the moments between work commitments are very important to me as well.
What initiatives or projects are you currently involved with, and why are they important?
Chris and I are passionate about supporting local charities, especially those that have to do with animals. We often collaborate with The Humane Society of Naples, which is a cause that is near to our hearts.
How do you balance your professional responsibilities with your personal life?
Between being a realtor and a business owner, I wear a lot of hats throughout the course of the day! I (attempt) to maintain a work/life balance by having a great team and support system around me and enjoying trips with friends and family throughout the year.
Who are some other women you admire or have been inspired by, and why?
Linda Oberhaus. She has served as CEO of The Shelter for Abused Women and Children since 2007. Her passion and devotion to helping others is truly mesmerizing. If every one of us had just a mere fraction of her love for others the world would be a better place.
HEATHER SCHWARZ
Tell us about yourself.
My family and I just moved to Naples a year and a half ago and we are all loving it here! My husband is Tim Chew, we have three girls: Samantha, Nicole, & Kiki. We have a Great Dane, Gracie, a Beagle/Lab mix, Buddy and a cat, Petunia.
What are some of the biggest challenges you've faced in your career and how did you overcome them?
One of the biggest challenges I’ve faced in the past has been because of my age relative to the work environment I was in, I was always underestimated. I was able to push through those obstacles by standing up for myself and becoming really good at what I was doing. I took a deep dive in becoming an expert at my job.
What initiatives or projects are you currently involved in, and why are they important?
I’m a commercial real estate developer at the core, and my husband and I have the privilege of helping non-profit organizations in their fundraising endeavors through our platform, TixForGood.org. I’m the creator of SwingScribe- a notebook that helps people learn how to play golf. I’m also the co-host of the Ladies Leadership Luncheon in Naples helping to uplift, inspire and empower women in SWFL.
Who are some other women you admire or have been inspired by, and why? Martha Stewart- she got a late start in life and completely rebranded herself. Anything she does is done at a level of perfection. Despite her stock trading setback, she is an absolute shining example of what it is to live up to one’s full potential in life.
What advice would you give to other women aspiring to make a difference in their communities or pursue leadership roles?
My mantra is to Uplift, Inspire and Empower myself and as a result, other people in my life. I feel that is a great recipe for personal success and also making a positive impact in the world.
