MY WHAT IF?
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MY WHAT IF? 〰️
Thirty years in the world of finance have shaped the way I see things—numbers, risk, reward—and have guided many of the choices I’ve made. But I’ve always believed that even the basics, learned young, can be incredibly impactful.
The earlier we understand how money works, the more confident and empowered we become. Yet financial literacy often arrives too late, if at all, or in ways that feel confusing, intimidating, or disconnected from real life. I wrote this book to change that—to give children the knowledge many adults wish they’d learned sooner (or still want to learn themselves).
At the heart of this book is the belief that even the most complex ideas can become simple and clear when they’re explained with the right words and the right approach. I’ve poured humor, warmth, and intention into these pages to capture a child’s imagination and build an early financial foundation that goes far beyond simple saving and spending—principles that can guide them throughout their lives.
This book is about money—yes. How to earn it, grow it, value it, and use it wisely.
However, it’s also about something deeper—courage, choice, resilience, creativity, and the belief that every child can find their own path and shape their own future. Entrepreneurship is not just a business path—it’s a mindset. It’s problem-solving. It’s dreaming. It’s trying, failing, learning, and trying again.
My hope is that your young reader is drawn in by a fun and lively story all on its own, and that it also gives them meaningful knowledge while sparking an inner curiosity. And I hope you enjoy the journey right along with them—maybe even learning something new yourself.
Inspiration for this book:
For several years, I had the honor of organizing a children’s entrepreneurial fair in our neighborhood. The event taught kids how to earn money and introduced them to the world of business. When I first became involved, I hoped to inspire young minds, including my son, to embrace early financial education and entrepreneurship. I didn’t anticipate how deeply inspired I would be in return. Seeing the young participants’ enthusiasm, creativity, and intelligence was truly remarkable. It reconfirmed in my mind that children will rise to the occasion if given the chance.
Fueled by their energy and effort (and a few inquiries from parents), I began to wonder: What if? What if I wrote a book that made finance approachable and fun for kids? What if I combined my thirty years in the industry with a decade of parenting to create something that sparks curiosity, builds confidence, and offers lessons that last well beyond childhood? That’s how this book—and the whole idea behind it—came to life.
Ashley Ragsdale Stockton, originally from Southern Virginia, has over 30 years of experience in finance, marketing and investments. She began her journey at the University of Virginia, where she earned a degree from the McIntire School of Commerce, with a concentration in Finance and Marketing. Her career took flight in New York City with roles in Equity Research at J.P. Morgan and Investment Banking at Merrill Lynch. In 2004, she relocated to Atlanta and led the Southeast Institutional Equity Sales desk for J.P. Morgan for close to two decades. Currently, she is Head of Investor Relations for Guardian Pharmacy Services.
An advocate for financial literacy and youth education, Ashley serves on the board of the Georgia Securities Association, raising funds to support statewide financial education programs for children. She also chairs her neighborhood’s annual Children’s Entrepreneurial Fair, helping young minds turn ideas into action.
In 2025, Ashley launched Ride Rabbit Ride to fill the gap in children's financial literacy and inspire young minds to explore entrepreneurship and business. Through storytelling, she aims to make financial concepts fun, accessible, and empowering for the next generation.
Ashley lives in Atlanta with her husband, their 11-year-old son, and their English Retriever. She enjoys tennis, mahjong, culinary adventures, traveling, and—most of all—spending time with family and friends.