Acquiring and Growing Exceptional Service Businesses
Acquiring and Growing Exceptional Service Businesses
Acquiring and Growing Exceptional Service Businesses
We partner with owners of professional and home service companies to provide respectful exits, operational clarity, and long-term stewardship.
Founded by John Drilling · Charlotte, North Carolina
We partner with owners of professional and home service companies to provide respectful exits, operational clarity, and long-term stewardship.
Founded by John Drilling · Charlotte, North Carolina
We partner with owners of professional and home service companies to provide respectful exits, operational clarity, and long-term stewardship.
Founded by John Drilling · Charlotte, North Carolina
Long-Term Ownership
Built to Hold, Not Flip
Founder-Led Acquisition Firm
Long-Term Ownership
Built to Hold, Not Flip
Founder-Led Acquisition Firm
Long-term ownership. Financial discipline. Respect for what you’ve built.
Long-term ownership. Financial discipline. Respect for what you’ve built.
What we offer
Long-term ownership, operational clarity, and respectful transitions.
Business Acquisitions
We acquire profitable professional and home service businesses from owners who are ready to step back while ensuring continuity and care.
Business Acquisitions
We acquire profitable professional and home service businesses from owners who are ready to step back while ensuring continuity and care.
Long-Term Ownership
We don’t buy to flip. Our focus is building durable businesses that compound value over decades.
Business Solutions
We don’t buy to flip. Our focus is building durable businesses that compound value over decades.
Operational Improvement
We strengthen systems, processes, and leadership to reduce owner dependency and increase stability.
Operational Improvement
We strengthen systems, processes, and leadership to reduce owner dependency and increase stability.
Management Continuity
Wherever possible, we retain existing teams and support leadership through thoughtful transitions.
Management Continuity
Wherever possible, we retain existing teams and support leadership through thoughtful transitions.
Financial Discipline
We prioritize cash flow, healthy margins, and responsible leverage to protect the business long-term.
Financial Discipline
We prioritize cash flow, healthy margins, and responsible leverage to protect the business long-term.
Modern Systems
We implement modern tools and automation—including AI where appropriate—to improve efficiency without replacing people.
Modern Systems
We implement modern tools and automation—including AI where appropriate—to improve efficiency without replacing people.
What we offer
Long-term ownership, operational clarity, and respectful transitions.
Business Acquisitions
We acquire profitable professional and home service businesses from owners who are ready to step back while ensuring continuity and care.
Long-Term Ownership
We don’t buy to flip. Our focus is building durable businesses that compound value over decades.
Operational Improvement
We strengthen systems, processes, and leadership to reduce owner dependency and increase stability.
Management Continuity
Wherever possible, we retain existing teams and support leadership through thoughtful transitions.
Financial Discipline
We prioritize cash flow, healthy margins, and responsible leverage to protect the business long-term.
Modern Systems
We implement modern tools and automation—including AI where appropriate—to improve efficiency without replacing people.
Who we are
Drilling Holdings is a privately held investment firm focused on acquiring and growing high-quality professional and home service businesses.
Founded by John Drilling, the firm was built on real operating experience—not financial engineering. John’s background spans entrepreneurship, consulting, and operational leadership across hundreds of businesses nationwide.
Since relocating to Charlotte, North Carolina in 2019, John has focused on building a portfolio of durable, cash-flow-positive companies that serve real needs and employ great people.
The goal is simple: buy good businesses, improve what matters, and hold them for the long term.
$500K-$10M
Target Revenue Range
$500K-$10M
Target Revenue Range
10-35%
Operating Cash Flow Target
10-35%
Operating Cash Flow Target
Long-Term
Ownership Philosophy
Long-Term
Ownership Philosophy
Who we are
Drilling Holdings is a privately held investment firm focused on acquiring and growing high-quality professional and home service businesses.
Founded by John Drilling, the firm was built on real operating experience—not financial engineering. John’s background spans entrepreneurship, consulting, and operational leadership across hundreds of businesses nationwide.
Since relocating to Charlotte, North Carolina in 2019, John has focused on building a portfolio of durable, cash-flow-positive companies that serve real needs and employ great people.
The goal is simple: buy good businesses, improve what matters, and hold them for the long term.
$500K-$10M
Target Revenue Range
10-35%
Operating Cash Flow Target
Long-Term
Ownership Philosophy
Portfolio & Focus Areas
Portfolio & Focus Areas
A glimpse into our most impactful projects and success stories.
A glimpse into our most impactful projects and success stories.
Professional Services
Accounting, legal, advisory, and other recurring-revenue service firms.
Home Services
HVAC, plumbing, electrical, and essential trade businesses.
Future Expansion
Selective entry into SaaS and real estate as the portfolio matures.
Professional Services
Accounting, legal, advisory, and other recurring-revenue service firms.
Home Services
HVAC, plumbing, electrical, and essential trade businesses.
Future Expansion
Selective entry into SaaS and real estate as the portfolio matures.
Professional Services
Accounting, legal, advisory, and other recurring-revenue service firms.
Home Services
HVAC, plumbing, electrical, and essential trade businesses.
Future Expansion
Selective entry into SaaS and real estate as the portfolio matures.
ChronoLux
Implemented a data-driven SEO and PPC strategy, boosting online visibility.
Professional Services
Accounting, legal, advisory, and other recurring-revenue service firms.
Home Services
HVAC, plumbing, electrical, and essential trade businesses.
Future Expansion
Selective entry into SaaS and real estate as the portfolio matures.
ChronoLux
Implemented a data-driven SEO and PPC strategy, boosting online visibility.
Professional Services
Accounting, legal, advisory, and other recurring-revenue service firms.
Home Services
HVAC, plumbing, electrical, and essential trade businesses.
Future Expansion
Selective entry into SaaS and real estate as the portfolio matures.
ChronoLux
Implemented a data-driven SEO and PPC strategy, boosting online visibility.
Professional Services
Accounting, legal, advisory, and other recurring-revenue service firms.
Home Services
HVAC, plumbing, electrical, and essential trade businesses.
Future Expansion
Selective entry into SaaS and real estate as the portfolio matures.
ChronoLux
Implemented a data-driven SEO and PPC strategy, boosting online visibility.
How we work with sellers
Selling your business is personal. We treat it that way.
What we don't do:
Strip costs to inflate EBITDA
Over-leverage businesses
Disrupt teams unnecessarily
Turning your life’s work into a spreadsheet exercise
Waste time with tire-kickers
Strip costs to inflate EBITDA
Over-leverage businesses
Disrupt teams unnecessarily
Turning your life’s work into a spreadsheet exercise
Waste time with tire-kickers
You can expect:
Direct, honest conversations
Transparent valuation discussions
Quick decisions
Respect for your legacy
No games, no wasted time
Direct, honest conversations
Transparent valuation discussions
Quick decisions
Respect for your legacy
No games, no wasted time
How we work with sellers
Selling your business is personal. We treat it that way.
What we don't do:
Strip costs to inflate EBITDA
Over-leverage businesses
Disrupt teams unnecessarily
Turning your life’s work into a spreadsheet exercise
Waste time with tire-kickers
You can expect:
Direct, honest conversations
Transparent valuation discussions
Quick decisions
Respect for your legacy
No games, no wasted time
What Our Clients Say
Our clients’ words reflect our commitment to excellence.
Their platform transformed how we approach campaigns. The intuitive tools and seamless integrations saved us a lot of time.
Jacob Williams
Tech CEO
Their platform transformed how we approach campaigns. The intuitive tools and seamless integrations saved us a lot of time.
Jacob Williams
Tech CEO
Their marketing approach brought in more foot traffic and online orders. The data-driven insights made all the difference.
Ethan Reynolds
Café Owner,
Their marketing approach brought in more foot traffic and online orders. The data-driven insights made all the difference.
Ethan Reynolds
Café Owner,
Their system improved our client engagement and lead conversions. The easy-to-use tools streamlined our entire sales process.
Nathan Carter
Fitness Founder,
Their system improved our client engagement and lead conversions. The easy-to-use tools streamlined our entire sales process.
Nathan Carter
Fitness Founder,
Their system improved our client engagement and lead conversions. The easy-to-use tools streamlined our entire sales process
Daniel Foster
Real Estate CEO
Their system improved our client engagement and lead conversions. The easy-to-use tools streamlined our entire sales process
Daniel Foster
Real Estate CEO
They refined our brand’s digital presence and increased customer retention. The personalized strategies made a huge impact.
Mitchell Apparel
Fashion CEO
They refined our brand’s digital presence and increased customer retention. The personalized strategies made a huge impact.
Mitchell Apparel
Fashion CEO
Their platform enhanced project coordination and design workflow. The advanced tools helped us meet deadlines stress-free.
Lucas Bennett
Architect
Their platform enhanced project coordination and design workflow. The advanced tools helped us meet deadlines stress-free.
Lucas Bennett
Architect
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.