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The Lovely Life of Leah



Leah Winstead is the founder of JetSet Mindset and the visionary behind Girl Gang Getaways. With over two decades of experience in corporate luxury travel and event planning, Leah has turned her passion for creating transformative experiences into a business that empowers women to reconnect with themselves and forge meaningful connections with others. Known for her vibrant enthusiasm, meticulous attention to detail and her knack for creating balance between relaxation and adventure, Leah curates unforgettable trips that inspire self-discovery and joy.



Have you met Leah yet!? She is one of the most positive and vibrant ladies that I know! Her presence brightens any room and we LOVE when she joins our Social Events! Keep an eye out for her the next time you join us! And, stay tuned for some exciting partnership news to come soon! In the meantime, let's get to know a bit more about her professional journey...



1) Did you always want to be, or see yourself getting into event planning?


Event planning wasn’t something I initially envisioned, but looking back, my journey seems to have naturally led me here. My dad and stepmom are retired elementary teachers, and growing up, we spent summers road-tripping across the USA, mostly camping. While I loved the outdoors and connecting with nature, spending so much time in tents made me realize I craved something different. I was fascinated by hotels—their amenities, like swimming pools and continental breakfasts, felt so special to me. When I saw Pretty Woman, I was struck by the kindness of the hotel manager teaching Julia Roberts’ character the proper fork to use—it showed me how impactful hospitality could be.

Although I didn’t grow up experiencing luxury, it always intrigued me. I majored in tourism in college, initially aiming for the hotel industry, which led to a thriving event planning career. JetSet Mindset allows me to blend my love of travel, my appreciation for hospitality, and my passion for creating meaningful experiences for others.



2) What specifically about JetSet Mindset/Girl Gang Getaways sets your business apart in the industry?


Girl Gang Getaways aren’t just trips—they’re journeys of self-discovery. We focus on creating an environment where women can relax, recharge, and build authentic friendships while enjoying luxury amenities like private chefs, yoga sessions, and massages. We go offsite from luxury accommodations on special tours and have once in a lifetime experiences for the attendees. It’s about fostering a supportive, judgment-free community. One of my favorite comments from our repeat travelers/clients/girl gang getaway alumni is how much they appreciate the personal touches that make every trip unique and truly transformational.



3) How do you balance family/work-life as being an entrepreneur, partner, and a mom?


I try to practice what I preach with JetSet Mindset in my own life, making self-care a priority, which fuels me to show up as my best self in all aspects of life. It’s all about setting priorities and boundaries. My family always comes first, but I’m intentional about my time—whether it’s focusing on my business, supporting my son, a freshman  at UNC Wilmington, or spending quality time with my partner, Chad. I also believe in focusing on self-care, which fuels me to show up as my best self in all aspects of life.



4) What is the part about your business that lights you up the most?


Seeing the transformation in women during and after a trip is the most rewarding part. Watching someone arrive stressed or unsure of themselves, only to leave glowing, confident, and connected with new friends, is incredibly fulfilling. I also love the creative process of planning each getaway—it’s like designing a masterpiece every time.



5) Do you have any advice/tips for women wanting to start their own business?


Start small but dream big. Take time to really understand your “why” and build a community that supports you. Don’t let fear, comparison, or perfectionism hold you back—progress beats perfection every time. Surround yourself with people who inspire and challenge you, and don’t be afraid to ask for help. I love meeting with other women and brainstorming.



6) What made you take the leap into entrepreneurship and starting Girl Gang Getaways?


The idea for Girl Gang Getaways came from a conversation with my friend Lauren on New Year’s Day 2023. She told me about a friend who attended a women’s retreat where participants didn’t know each other beforehand. It immediately clicked. I’ve always wanted to go on girls’ trips, but to be honest, I never had a group of women who could travel with me. So, I decided to create my own girl gang—a community of women in the same situation, who might not have a group able to travel with them but still want that experience.


Through my background in planning luxury corporate events and my Rolodex of global contacts, I can make these trips affordable and attainable for anyone interested. That passion, combined with the opportunity to empower women to step away from their routines, recharge, and form meaningful connections, gave me the confidence to take the leap into entrepreneurship.







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