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Balancing Craftmenship with Chaos: The Double Life of Chris Cooney

Chris Cooney, of CWC HANDYMAN and UNCLE GRUMPY STUMPS, in Milford, Pennsylvania, isn’t your typical small business owner—he’s living a double life in the trades. By day, he runs CWC Handyman Services, where precision, craftsmanship, and care define every project. But when the sawdust settles, he switches gears to run Uncle Grumpy Stumps, a business built on raw power and destruction. In this episode of SWIVL SESSIONS, Chris shares how he built two wildly different, equally successful businesses—and why integrity, hustle, and guts are the common thread between them, because, as he states “sometimes you have to go into the hole to grow.”  Whether you’re building something up or tearing it down, this episode will hit home.

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About the Guest

Chris Cooney

Owner

Chris Cooney is a fearless entrepreneur who has built two successful field service businesses over 23 years. Based in Milford, Pennsylvania, Chris operates at the intersection of New York, New Jersey, and Pennsylvania, serving customers across all three states. A self-described "born builder," Chris combines the precision of high-end carpentry with the raw power of stump grinding, proving that diverse skill sets can create multiple revenue streams in the Home Services industry. Starting as a young apprentice carpenter, Chris built his reputation through decades of quality craftsmanship and unwavering integrity. His journey from struggling with basic business fundamentals to running two profitable enterprises demonstrates how practical experience, customer relationships, and strategic risk-taking can overcome the lack of formal business education. His transition from purely physical carpentry work to equipment-based stump grinding shows his ability to adapt and identify market opportunities while maintaining his commitment to excellence.

Connect

Location: Complete home remodeling, high-end carpentry, stump grinding and removal

Company Overview

CWC Handyman Service LLC

Services

  • Services: Complete home remodeling including siding, doors, windows, kitchens, bathrooms, flooring, sheetrock, basement finishing
  • Specialty: High-end oak and iron staircases, mahogany wine cellars
  • Current Status: Booked 3-4 months out, operates primarily through word-of-mouth referrals
  • Business Model: Owner-operator with one employee (his son) plus licensed subcontractors
  • Services: Professional stump grinding and removal
  • Equipment: 96 horsepower turbo diesel stump grinder
  • Target Revenue: $125k gross, $75k net annually
  • Growth Strategy: Partnering with tree service companies who lack stump grinding equipment

Core Mission

Delivering exceptional craftsmanship and reliable service across complementary Home Services industries while building long-term client relationships based on trust and quality work.

Business Model

Multi-business approach combining high-skill handyman services with equipment-based stump grinding, leveraging different revenue streams and seasonal opportunities to maintain year-round income stability.

Episode Summary

Chris Cooney, of CWC HANDYMAN and UNCLE GRUMPY STUMPS, in Milford, Pennsylvania, isn’t your typical small business owner—he’s living a double life in the trades. By day, he runs CWC Handyman Services, where precision, craftsmanship, and care define every project. But when the sawdust settles, he switches gears to run Uncle Grumpy Stumps, a business built on raw power and destruction. In this episode of SWIVL SESSIONS, Chris shares how he built two wildly different, equally successful businesses—and why integrity, hustle, and guts are the common thread between them, because, as he states “sometimes you have to go into the hole to grow.”  Whether you’re building something up or tearing it down, this episode will hit home.

0:00Handyman Business Owner: From Apprentice to Entrepreneur
3:00Starting Business Without Training: Early Mistakes & Lessons
6:00Pricing Jobs Right: Material Waste & Estimating Tips
9:00Building Client Base: Word of Mouth Marketing Strategy
12:00Small Business Structure: LLC Tax Benefits Explained
15:00Tree Service Gap: Finding Stump Grinding Opportunity
18:00Equipment Investment: $65K Stump Grinder Purchase Decision
21:00Running Two Businesses: Handyman vs Stump Grinding
24:00Physical Work Challenges: Transitioning to Equipment Based
27:00Field Service Technology: Adopting CRM for Contractors
30:00Business Growth Strategy: Investment & Future Planning
33:00Entrepreneur Advice: Overcoming Fear & Naysayers

On Natural Ability

"I was just born a builder. When I was little, I could take sets of different things and I could build things that adults couldn't build."

On Calculated Risks

"Sometimes you have to go into the hole to grow a little bit."

On Building Client Relationships

"There's a customer's one time and a client is many. Every time they have a need, a client will call you. A customer will call you once, you're done."

On Word-of-Mouth Marketing

"This is the only advertising I don't really pay for advertising. I'm so well known at this point. I'm booked for three months solid."

On Overcoming Fear

"Fear not. No fear. There are going to be naysayers... This is America. You will make it."

On Daily Progress

"If every day you're thinking about what you have to do and you're accomplishing something every single day, you will make it."

Essential Business Foundation

  • Get proper business education in accounting, estimating, and business management
  • Choose LLC over DBA for tax advantages and business structure benefits
  • Plan for material waste by always ordering 15% extra materials to avoid delays
  • Learn from early mistakes and use them as education for future success

Growth Strategy

  • Build clients, not just customers - focus on long-term relationships over one-time transactions
  • Understand seasonal patterns and plan cash flow around predictable slow periods
  • Invest in quality equipment that allows competitive pricing and faster job completion
  • Look for complementary business opportunities that leverage existing relationships

Mindset & Approach

  • Ignore the naysayers and don't let others' fears limit your potential
  • Embrace calculated risks - sometimes you need to "go into the hole" to grow
  • Maintain integrity as small businesses must deliver on promises to build reputation
  • Adapt to technology and embrace new systems and tools to stay competitive

Market Opportunity Recognition

  • Look for service gaps in established industries
  • Consider complementary businesses that work together or fill market voids
  • Understand your competition and position yourself between low-quality and overpriced options
  • Partner with businesses that need services you can provide

Operational Excellence

  • Develop accurate estimating skills through experience and tracking past jobs
  • Account for all costs including materials, labor, waste, and overhead
  • Build relationships with subcontractors for specialized work beyond your expertise
  • Transition to systems and technology as the business grows

Entrepreneurial Resilience

Chris demonstrates how persistence through early mistakes and financial challenges builds stronger business foundations and creates lasting success in competitive markets.

Market Gap Analysis

The stump grinding business perfectly illustrates how observing industry dynamics and identifying what established businesses aren't offering can reveal profitable opportunities.

Physical vs Strategic Work

The contrast between hands-on craftsmanship and equipment-based services shows different paths to business success and how entrepreneurs can evolve from labor-intensive to more scalable models.

Technology Adoption

A traditional contractor's journey toward digital systems reflects broader industry evolution and the importance of staying current with business tools and platforms.

American Dream Realization

Chris embodies the self-made entrepreneur who creates opportunities through hard work and smart decisions, proving that formal education isn't always necessary for business success.

Integrity-Based Growth

Building a reputation through quality work and honest dealings serves as the foundation for sustainable business success and organic marketing through referrals.

Multi-Business Strategy

How complementary businesses can provide diversification, multiple income streams, and protection against seasonal fluctuations or market changes.

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