Today we’d like to introduce you to Courtney S. Jenkins.
Hi Courtney S. , 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?
I still remember my first mentor. He was a personal development coach, and at the end of our sessions he would tell me he could see me becoming a coach too. I used to brush it off and say maybe one day, probably later in life after I retire. Looking back, that was really the start of everything.
About a year later, I got my coaching certification. Around the same time, I started writing every day with the goal of publishing my first book. I wanted to build credibility and share lessons from my own life, so I wrote a self help book based on what I had learned about creating real change. What started as personal development coaching evolved into financial coaching and now I operate as a wealth strategist through my company Legacy Under Oak. In this role, I help individuals and organizations strategically deploy their capital through investing, business growth, career positioning, and legacy building.
In many ways, my first mentor didn’t just encourage me, he helped set the direction for the work I’m doing today. That’s why I really believe mentorship and coaching are so important, because the right one can truly be life changing.
I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
Entrepreneurship is never a smooth road. One of the biggest challenges I faced was learning how to be a business owner while learning who I am as an individual. Entrepreneurship is like looking at yourself in the mirror. Things that you do, things that you tolerate, things that you negotiate in your personal life or have a lack of, will reflect who you are as a business owner. In the beginning, I struggled with confidence. I had the education and certifications, but I was still learning how to fully own my voice and my value as a coach. Imposter syndrome plays a big part in entrepreneurship and I can admit I have experienced it before. There were times I questioned if I was qualified enough, especially when I was stepping into new spaces like financial coaching.
My finances were another challenge. I took a huge risk on myself moving from New Jersey to Texas with no car and no guaranteed income, just my vision and my work. I’ve had moments where clients paid late or were inconsistent, and I had to learn how to stay mentally steady through that. Honestly, that’s what shaped me the most. It taught me resilience and how to trust myself through the uncertainty. I’ve come to realize that entrepreneurship is spiritual. How you show up in your life is exactly how you show up in your business, so it forces you to grow in every area.
Becoming an entrepreneur taught me to be very intentional about my business, but most importantly about my life. I started surrounding myself with people who had already built success for themselves. Being around seven and eight figure earners changed how I think about wealth, economics, business, decision-making, and time. I started creating routines for myself to establish better habits. I didn’t just observe it, I applied it to my life.
Thanks – so what else should our readers know about Legacy Under Oak?
My business, Legacy Under Oak, is a financial education company built to help individuals and organizations change their relationship with money from how they think about it, manage it, and grow it. I don’t just teach financial concepts. I focus on behavior and execution. Sometimes people know what they should be doing with their money, but struggle with consistency, structure, and follow-through. My work bridges that gap by changing mindsets and then turning knowledge into a clear framework that aligns with their life.
I specialize in helping clients build strong financial foundations, improve money habits, and position themselves for long-term wealth through investing, business growth, and career positioning. What sets my work apart is that I focus on how people operate, not just what they know or want to know. Financial outcomes are a direct reflection of behavior, discipline, and decision-making.
I also have personal investing experience, primarily in the stock market across multiple asset classes, including equities, options, futures, and forex trading. I don’t just teach personal development and financial principles. I apply them in my own decisions. Legacy Under Oak is about helping people move from financial uncertainty to financial control so they can build financially grounded lives, businesses, and long-term legacy.
Before we go, is there anything else you can share with us?
Yes, I would just add that everything I teach and build through Legacy Under Oak is rooted in real experience, not theory. I’ve had to take risks on myself, rebuild, and learn discipline while navigating uncertainty. I still continue to take risks and establish better habits because in entrepreneurship that’s a never ending journey. Which is why I push self improvement when educating others. I understand what it feels like to question yourself, the journey, the goals, the dreams, starting over all while navigating life. That’s why my work focuses so heavily on behavior, structure, and execution, not just information. When people change how they think, decide, and operate, their financial reality follows. My goal is to help people make that shift in a way that lasts so they ultimately become their own coach.
Contact Info:
- Website: https://courtneysjenkins.com
- Instagram: https://www.instagram.com/courtneysjenkins
- LinkedIn: https://www.linkedin.com/in/courtney-s-jenkins-cfei%C2%AE-cbc%E2%84%A2-ccn%C2%AE-09880887
- Other: https://open.spotify.com/show/1rGAZyubEiNLvi04fD1qna
