Today we’d like to introduce you to Davon Calloway.
Hi Davon, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
My journey into the financial industry began in the Marine Corps in 2014 while I was on recruiting duty. During that time, an advisor from Edward Jones came in to speak with us, which planted an early seed of interest in finance. As I prepared to transition out of the Marine Corps in 2015, I wasn’t entirely sure what path I wanted to pursue, but I was enrolled in school and earned my bachelor’s degree in accounting.
After graduating, I quickly realized that many accounting roles required experience that was difficult to obtain right out of school. Since I already had a background in recruiting, I decided to expand on that skill set and returned to school to earn my master’s degree in human resources management. I viewed recruiting as an extension of HR and a practical way to build a career.
In 2017, while completing my master’s program, I was presented with an opportunity at JPMorgan Chase to enter a three-month program designed to obtain securities licenses and become a financial advisor. I successfully passed the Series 7 but narrowly missed the Series 66 by one point. With the intensity of the training and my commitment to finishing my master’s degree, I made the decision to complete my education and step away from the securities path at that time. I finished my master’s degree later that year.
From 2018 through 2020, I worked in the recruiting field. When the pandemic hit in 2020 and the market experienced significant volatility, a friend introduced me to options trading, specifically buying puts in a declining market. I quickly realized this wasn’t new to me—I had learned these concepts during my time studying and training at JPMorgan Chase. That experience reignited my interest in finance.
After being laid off by another company a few years later, I made a pivotal decision in 2023 to fully commit to the financial industry. This decision was driven by two things: witnessing firsthand how financially illiterate many individuals and families were and recognizing that I was successfully applying financial strategies in my own life.
Beginning in 2023, I immersed myself in learning and development across several firms, including First Financial and Primerica. In 2025, I obtained all the necessary licenses to officially become a financial advisor with my current company. Since then, I’ve been moving forward with a clear purpose—helping families build financial literacy, create long-term strategies, and work toward their own version of financial freedom.
Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
Along the way, there were several obstacles and challenges—both in obtaining the required licenses and in developing a true understanding of how to apply financial strategies effectively. One of the biggest lessons I learned is that there is no one-size-fits-all approach to financial planning. Every individual and family has different goals, risk tolerances, and circumstances.
Early on, there was also the fear of making the wrong recommendation or feeling like I didn’t know everything. Over time, I came to understand that financial advising isn’t about having every answer immediately—it’s about continuously learning, asking the right questions, and building strategies that align with each client’s unique situation. That mindset has shaped how I serve families today, with a strong focus on education, transparency, and thoughtful decision-making.
As you know, we’re big fans of Guiding Generations LLC . For our readers who might not be as familiar what can you tell them about the brand?
I am an independent contractor operating under the First Command umbrella and serve as a fiduciary, which means I am legally and ethically required to act in the best interest of my clients at all times. Before making any recommendations, I take the time to truly get to know you, your finances, goals, risk tolerance, and what matters most to you.
My practice is centered on helping you achieve your version of financial freedom, whatever that may look like. I’m also very realistic and transparent in explaining that financial planning is a marathon, not a sprint. Real, lasting results take time, discipline, and consistency.
Think of me as the captain of your ship, you choose the destination, and I help guide you there with a clear plan, steady direction, and adjustments along the way when needed.
What do you like and dislike about the city?
The area is forever growing. I dislike all this construction that feels like its never done
Pricing:
- free consultation
Contact Info:
- LinkedIn: www.linkedin.com/in/davon-calloway
