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Who We Are

Holly Bell

Founder, Principal Consultant


Founding owner Holly Bell is a seasoned financial strategist with a reputation for turning complex challenges into sustainable success. With over 30 years of experience in business banking, regulatory leadership, and corporate consulting, Holly brings a unique ability to bridge high-level vision with day-to-day execution.


A former Nashville music industry banker turned entrepreneur and public-sector executive, Holly has built and scaled businesses across multiple sectors. While serving as the Director of Cannabis for the Florida Department of Agriculture and Consumer Services, she launched and regulated Florida’s hemp industry, transforming it into a multi-billion-dollar enterprise employing over 180,000 people.


Today, Holly serves as a fractional CFO and strategic advisor to businesses across the U.S., including the largest private broadcast studio in the Eastern United States. She is especially skilled in forensic accounting, regulatory compliance, operational design, and preparing companies for sale or investment.


Holly is a gifted communicator, coach, and team builder known for her direct, effective leadership and sharp analytical mindset. Driven by her passion to help businesses grow sustainably while maximizing every asset, system, and team member, she helps visionary founders transform ideas into new programs, departments, or companies. 


She holds a Bachelor’s degree in Agricultural Economics from Purdue University.

Brian Gupton

Co-founder, Principal Consultant


Brian is a co-founder of HB Advisory Group and a highly respected finance professional with over 35 years of experience in banking, ERISA compliance, strategic planning, and financial consulting. Known for his analytical sharpness and steady leadership, Brian helps startups and mid-sized companies build the strong financial infrastructure they need to thrive, not just today, but well into the future.


His career spans commercial banking, trust and retirement services, and private financial advising. As one of the nation’s top subject matter experts (SMEs) in ERISA, Brian has helped countless businesses navigate complex regulatory requirements with confidence and clarity. His track record of success, to include founding a successful trust company in North Carolina in 1990, speaks to his vision, expertise, and operational execution.


Through his consulting work, Brian specializes in equipping early-stage businesses with the tools and structures of much larger companies, allowing them to scale seamlessly and sustainably. He also serves as a personal CFO to family offices and individuals, providing trusted financial oversight with discretion and care.


Whether guiding a company’s strategic growth or helping a family manage generational wealth, Brian is known for his integrity, precision, and commitment to long-term success.

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