Thomas L Woolbright, CPA, MT
TITLE
Associate Principal
HOMETOWN
Franklin, NC
YEARS OF EXPERIENCE
14
EDUCATION
"There is one rule, above all others, for being a man. Whatever comes, face it on your feet." - al'Lan Mandragoran (The Wheel of Time)
Thomas Woolbright is a CPA with deep expertise in tax services for small businesses and individuals. His specialty spans estate and trust planning, tax research, and strategic planning designed for efficiency. Thomas believes true value goes beyond simply filing “correct” returns; he strives to equip clients with clarity and confidence in their finances.
Before his career in accounting, Thomas served as an Intelligence Analyst in the NC Army National Guard and worked as a service writer at a local dealership, roles that taught him discipline, multitasking, and the work ethic he brings to every client engagement.
His journey to Dark Horse began at a small firm, where he developed hands-on experience and a client-focused approach. After advancing to shareholder level, he sought more complex challenges and moved to a regional firm. There, he found the work impersonal and unsustainable until he discovered Dark Horse. Here, Thomas found the best of both worlds: the structure to support meaningful, personalized client work and the flexibility to maintain balance and authenticity in his relationships and approach.
Originally from South Florida, Thomas now lives in the mountains of North Carolina with his wife, JuliaMarie, and their three sons: Thomas, Anthony, and Benedict. Born within two years of each other, they ensure that life at home is never quiet.
When not advising clients, Thomas is a competitive bowler who has thrown perfect games and even converted the legendary 7–10 split. He also enjoys tennis (despite claiming no skill), golf, board games, and PC gaming. A Denver Broncos fan, he follows tennis closely and counts Wimbledon as the highlight of the sports calendar. An avid reader, The Wheel of Time tops his list of favorite series, with the timeless works of Jane Austen not far behind.
Specialties
Estate Trusts Tax Services
Tax Planning
1031 Exchanges
Business Tax
Rental Properties
Industries
About
Thomas Woolbright is a CPA with deep expertise in tax services for small businesses and individuals. His specialty spans estate and trust planning, tax research, and strategic planning designed for efficiency. Thomas believes true value goes beyond simply filing “correct” returns; he strives to equip clients with clarity and confidence in their finances.
Before his career in accounting, Thomas served as an Intelligence Analyst in the NC Army National Guard and worked as a service writer at a local dealership, roles that taught him discipline, multitasking, and the work ethic he brings to every client engagement.
His journey to Dark Horse began at a small firm, where he developed hands-on experience and a client-focused approach. After advancing to shareholder level, he sought more complex challenges and moved to a regional firm. There, he found the work impersonal and unsustainable until he discovered Dark Horse. Here, Thomas found the best of both worlds: the structure to support meaningful, personalized client work and the flexibility to maintain balance and authenticity in his relationships and approach.
Originally from South Florida, Thomas now lives in the mountains of North Carolina with his wife, JuliaMarie, and their three sons: Thomas, Anthony, and Benedict. Born within two years of each other, they ensure that life at home is never quiet.
When not advising clients, Thomas is a competitive bowler who has thrown perfect games and even converted the legendary 7–10 split. He also enjoys tennis (despite claiming no skill), golf, board games, and PC gaming. A Denver Broncos fan, he follows tennis closely and counts Wimbledon as the highlight of the sports calendar. An avid reader, The Wheel of Time tops his list of favorite series, with the timeless works of Jane Austen not far behind.
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