The First Oak Team

Ryan is the firm’s managing member. His primary focus is providing in-depth financial planning and investment management strategies for his clients.

Ryan wants his life’s work to focus on helping people, and his desire to work specifically in wealth management started at a young age watching the journey of his entrepreneurial parents. He saw firsthand the success of a family business along with the pitfalls of not having a focused and comprehensive financial plan.

After earning his bachelor’s degree from Cal Poly, San Luis Obispo, he packed everything he owned in his truck and moved to Raleigh, where he began his career at Fidelity Investments. After helping hundreds of Fidelity customers, he realized he could help people even more if they were his clients. He then joined Edward Jones and later moved to Oak City Consulting before co-founding First Oak Wealth Management. With practical investment and financial planning experience, his goal was to create the type of firm he would choose to work with if he were a client. A firm where the clients’ interest comes ahead of the advisor’s. A natural-born planner, Ryan enjoys getting to know the stories behind what clients want to accomplish and uses his financial acumen to chart the right course for each person or family.

Ryan holds the Certified Private Wealth Advisor^® designation, which he earned through the University of Chicago Booth School of Business, in coordination with the Investment & Wealth Institute^™. The CPWA^® certification program is an advanced credential created specifically for wealth managers serving the unique needs of business owners, executives and high-net-worth clients with a particular focus on strategies to minimize taxes, monetize and protect assets, maximize growth, and transfer wealth.

Ryan is an active member of Providence Baptist Church. He and his family live on a small gentlemen’s farm in Raleigh. Outside of the office, he enjoys fishing with his sons, manning the grill and hosting family and friends for dinner.

Austen Hawkey joined the team in 2024 with a proven track record of developing and executing personalized, goal-based wealth plans. 

His career in financial services began with First Citizens Bank in 2007. From there, he further honed his wealth management experience as a fiduciary officer with PNC Wealth Management. He went on to serve in advisory positions of progressive responsibility with Bank of America Private Bank. Most recently, he was a senior wealth advisor and head of financial planning with Armor Investment Advisors.

 An alumnus of the Kenan-Flagler School of Business at the University of North Carolina at Chapel Hill, he earned a Master of Accounting degree specializing in taxation. He holds a Bachelor of Business Administration in trust and wealth management, with a minor in financial planning from Campbell University. A CERTIFIED FINANCIAL PLANNER™, Austen is also a licensed Certified Public Accountant.

 Austen is a member of the Wake County Estate Planning Council and the American Institute of Certified Public Accountants. He lives in Raleigh, North Carolina, with his wife and children and is an active member of Summit Church. Away from the office, he enjoys spending time with his family, keeping up with his favorite sports, as well as fishing, hunting, and an occasional round of golf.

Grace joined the First Oak team in 2018. With a passion for service, her expertise is in helping clients develop and implement strategies to create, grow and preserve wealth.

An alumna of Colorado State University, her career in financial services began at Charles Schwab in Denver, Colorado. She served as a client service registered representative, advanced trade specialist and senior specialist for client development. While with Charles Schwab, she relocated to Little Rock, Arkansas, serving as an associate financial consultant. She obtained a CERTIFIED FINANCIAL PLANNER^™ designation during that time, which she retains. Before joining the First Oak team, she served as a financial advisor with Morgan Stanley at their North Raleigh office.

To be closer to family, Grace returned to Colorado. She works from her home office against the backdrop of the Front Range mountains, often with her snoozing Australian Shepherd at her feet.

Anna joined First Oak in 2022 with over 25 years of wealth management industry experience. If you call or stop by our office, Anna will often be the person that welcomes you while also overseeing many behind-the-scenes functions to support our team. She has a keen eye for detail and a passion for serving others.

Her wealth management career began at Wells Fargo Advisors, where she served clients as a financial advisor and registered client associate for 15 years. In 2015, she joined Ameriprise Financial as a registered client service associate. At both firms, she worked closely to onboard and serve clients.

An alumna of the University of South Carolina, she holds a Bachelor of Science in Business. She continued her education at Webster University’s George Herbert Walker School of Business and Technology, earning a Master of Business Administration.

A native of South Carolina, Anna has called Raleigh home since 2012. An endurance athlete and avid hiker, she enjoys exploring National and State Parks. When not on the hiking trails, she enjoys recharging at home with her yellow Labrador retriever.

Catherine joined First Oak in 2017. Earlier in her career, she worked at ITT Sheraton Hospitality Corporation, where she held management positions at the Sheraton Washington Hotel in Washington, D.C., and the Sheraton Inner Harbor Hotel in Baltimore, Maryland. She was instrumental in opening luxury hotels in Chicago and New York City. An alumnus of Roanoke College in Salem, Virginia, she studied foreign languages.

A native of Washington, Catherine moved with her family to the Triangle over 20 years ago. Outside of the office, she enjoys spending time with her family, including her two beloved, four-legged “kids.” She enjoys travel, a passion that took root as a child when she lived in Europe, and spending time exploring the outdoors both in the Triangle and beyond. Catherine volunteers her time with women’s and children’s ministries.