Built on Ownership, Discipline, and Long-Term Thinking
Drilling Holdings is a privately held acquisition firm focused on buying and growing exceptional professional and home service businesses.
A Different Kind of Buyer
A Different Kind of Buyer
Drilling Holdings was created for business owners who care deeply about what they’ve built—and want to see it continue under responsible ownership.
Founded by John Drilling, the firm is rooted in real operating experience. John has spent his career building, scaling, and advising businesses from the inside, with a focus on operations, systems, financial discipline, and sustainable growth.
We don’t approach acquisitions as transactions. We approach them as long-term commitments—to employees, customers, and the legacy of the business itself.
Long-term ownership
Long-term ownership
Not quick flips
Not quick flips
Cash-flow-first decision making
Cash-flow-first decision making
Respect for people, culture, and customers
Respect for people, culture, and customers
Systems and processes that reduce owner dependency
Systems and processes that reduce owner dependency
A Different Kind of Buyer
Drilling Holdings was created for business owners who care deeply about what they’ve built—and want to see it continue under responsible ownership.
Founded by John Drilling, the firm is rooted in real operating experience. John has spent his career building, scaling, and advising businesses from the inside, with a focus on operations, systems, financial discipline, and sustainable growth.
We don’t approach acquisitions as transactions. We approach them as long-term commitments—to employees, customers, and the legacy of the business itself.
Long-term ownership
Not quick flips
Cash-flow-first decision making
Respect for people, culture, and customers
Systems and processes that reduce owner dependency
About the Founder
John Drilling is the Founder & CEO of Drilling Holdings.
His background spans entrepreneurship, consulting, and operational leadership across hundreds of businesses nationwide. Rather than approaching business from a purely financial lens, John focuses on building durable systems, strong teams, and predictable cash flow.
After relocating to Charlotte, North Carolina in 2019, John formed Drilling Holdings to acquire and grow service-based businesses with a long-term mindset—creating value not just financially, but for employees, customers, and future generations.
At its core, Drilling Holdings exists to build something lasting—for John’s family, the people inside the businesses, and the communities they serve.
About the Founder
John Drilling is the Founder & CEO of Drilling Holdings.
His background spans entrepreneurship, consulting, and operational leadership across hundreds of businesses nationwide. Rather than approaching business from a purely financial lens, John focuses on building durable systems, strong teams, and predictable cash flow.
After relocating to Charlotte, North Carolina in 2019, John formed Drilling Holdings to acquire and grow service-based businesses with a long-term mindset—creating value not just financially, but for employees, customers, and future generations.
At its core, Drilling Holdings exists to build something lasting—for John’s family, the people inside the businesses, and the communities they serve.
Experience That Informs Our Approach
• Built and scaled service-based businesses
• Worked directly inside hundreds of real operating companies
• Deep experience in operations, systems, and cash-flow management
Experience That Informs Our Approach
• Built and scaled service-based businesses
• Worked directly inside hundreds of real operating companies
• Deep experience in operations, systems, and cash-flow management
Our Philosophy
We Buy to Hold
Our goal is to own great businesses for decades, not quarters.
We Buy to Hold
Our goal is to own great businesses for decades, not quarters.
We Invest in What Works
Strong fundamentals matter more than flashy growth.
We Invest in What Works
Strong fundamentals matter more than flashy growth.
We Respect the Legacy
The business you built deserves thoughtful stewardship.
We Respect the Legacy
The business you built deserves thoughtful stewardship.
We Operate with Discipline
Healthy margins, predictable cash flow, and responsible leverage.
We Operate with Discipline
Healthy margins, predictable cash flow, and responsible leverage.
We Buy to Hold
Awarded by Digital Excellence
We Invest in What Works
Awarded by Global Search Awards
We Respect the Legacy
The business you built deserves thoughtful stewardship.
We Operate with Discipline
Healthy margins, predictable cash flow, and responsible leverage.
Considering a Transition?
If you’re thinking about stepping back from your business—or simply want to explore options—I’m always open to a conversation.
No pressure. No pitch. Just a discussion to see if there’s a fit.
Considering a Transition?
If you’re thinking about stepping back from your business—or simply want to explore options—I’m always open to a conversation.
No pressure. No pitch. Just a discussion to see if there’s a fit.
Considering a Transition?
If you’re thinking about stepping back from your business—or simply want to explore options—I’m always open to a conversation.
No pressure. No pitch. Just a discussion to see if there’s a fit.