Ashley Rainey
Ashley Rainey is an entrepreneur, program coordinator, and consultant who has built her career on blending creativity with strategy. She is the founder of Enchanted Tales Tours, a VIP concierge service that helps families experience Disney and Universal theme parks with ease, magic, and unforgettable memories. What began as a passion for hospitality and storytelling has grown into a thriving business known for its personalized itineraries, seamless operations, and dedication to client experience.
Alongside running her business, Ashley serves as Project & Operations Coordinator for the Society for Collegiate Leadership & Achievement, where she leads national programs that support student leadership and career readiness. With a Master of Education in Educational Studies from the University at Buffalo, she brings expertise in project management, operations, and client engagement to every role she takes on.
Fluent in English and Spanish, Ashley is passionate about building connections across cultures and communities. Her volunteer work in literacy advocacy further reflects her commitment to empowering others through education. Whether helping families plan seamless vacations or leading large-scale initiatives in higher education, Ashley combines heart, vision, and organization to create meaningful impact.
• LinkedIn Advertising Fundamentals Certification
• LinkedIn Marketing Strategy Certification
• SCLA Career Readiness Certification
• Teaching English as a Second Language
• Masters in Education from University at Buffalo
• Bachelor in Health & Human Services University at Buffalo
• - Alpha Sigma Tau
What do you attribute your success to?
I attribute my success to persistence and the people who have supported me along the way. I have always been willing to put in the work, to learn as I go, and to keep moving forward even when the path was not clear. At the same time, I know I would not be where I am without the encouragement of my family. That combination of determination and support has allowed me to grow, take risks, and build opportunities that align with my passions.
What’s the best career advice you’ve ever received?
The best career advice I have ever received is that the worst they can say is no. It is a simple reminder that asking for opportunities, putting yourself forward, or taking a chance rarely carries as much risk as we imagine. A “no” does not close every door, it just means you are one step closer to finding the right “yes.”
What advice would you give to young women entering your industry?
The advice I would give to young women entering this industry is to know your worth and add tax. It is easy to undervalue yourself when you are just starting out, but your skills, perspective, and effort have real value from day one. Do not be afraid to speak up, set boundaries, and advocate for yourself, even if it feels uncomfortable at first. Opportunities come and go, but the confidence you build by standing firm in your worth will carry you forward no matter where your career takes you.
What are the biggest challenges or opportunities in your field right now?
One of the biggest challenges in my field is getting your foot in the door. In both education and entrepreneurship, opportunities often go to people who already have connections or a long track record. For those who are new or building something of their own, it takes persistence and resilience just to be noticed. The hardest part is not usually the lack of passion or skill, but the lack of access. Finding the right people who will listen, trust you, and give you that first chance can be the biggest hurdle. At the same time, that challenge creates space for opportunity. Once you break through, there is room to innovate and to meet real needs, whether that is helping students succeed or creating seamless and personalized travel experiences for families.
What values are most important to you in your work and personal life?
What matters most to me, both at work and at home, is leading with honesty, building meaningful connections, and making a positive impact. I want the people I work with and the families I serve to feel cared for and supported. At the end of the day, whether it’s through my business, my career, or with my loved ones, I try to bring joy, growth, and purpose into everything I do.