The Wealthy Contractor

The Contractor Systems Behind a 1-Day Workweek | Chris Carey (Ep. 257)


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Our guest today built two home improvement businesses doing $18M combined. And for two years, he ran them on JUST 1 DAY per week.

Not because he checked out.

But because he stopped being the safety net.

In this episode of The Wealthy Contractor podcast, I sit down with Chris Carey, owner of Windows Direct and Baths Direct. We break down the systems, leadership structure, and sales disciplines that replaced owner dependency and allowed his home improvement business to run without him.

Chris didn’t work himself to exhaustion, hoping to earn the right to work less.

He didn’t wait for “one more hire,” “after this busy season,” or “once things calm down.”

Instead, he used fewer workdays to expose what was broken inside his contractor business.

When he wasn’t there to jump in:

👉 Systems had to WORK

👉 Leaders had to LEAD

👉 Prices had to SUPPORT the business (not just close deals)

👉 Accountability became non-negotiable

Inside this conversation, Chris and I reveal:

🔥 Why being “always available” is the fastest way to keep broken systems alive

🔥 The sales system shift that made a 30% price increase possible overnight

🔥 Why chasing growth without structure creates chaos at $10M+

🔥 What actually happens when you keep feeding leads to low performers

🔥 How leadership accountability replaces owner micromanagement

🔥 The counterintuitive move that made a 1-day workweek possible

🔥 Why the business should serve your life (not trap you in it)

In just 37 minutes, you’ll see exactly how to reduce your workload as a contractor (without jobs stalling, margins slipping, or the wheels falling off).

And if you’re honest…

You already know exactly where your business would crack if you stepped away for a week 😬


Key Highlights: 

(00:00) Why working 60–70 hours a week is usually a systems problem, not a work ethic issue

(01:44) How Chris built an $18M home improvement business from the ground up

(03:47) The classic first-year mistake that leaves contractors “busy” but broke

(06:00) Why satellite locations can be wildly profitable when you centralize the right systems

(07:14) How an introvert became a top producer… and why sales systems beat personality every time

(07:57) “What’s a sales system?” The moment low prices stopped working

(08:44) The 30% price increase that scared the sales team… and why it worked immediately

(11:10) Why owners must sell first before expecting their team to follow

(12:19) How structured sales systems pushed gross margins past 60%

(13:18) The hidden cost of “keeping them busy” (and why low performers stall growth)

(16:05) Why Chris intentionally paused growth to fix systems (and how that decision paid off)

(18:27) What actually breaks when you hit $10M+ without leadership in place

(20:26) The modern contractor advantage that didn’t exist 15 years ago (Hint: staying stuck is optional!)

(28:42) How a 1-day workweek exposed broken systems and weak leadership

(33:12) Why hiring “industry unicorns” failed (and how promoting the right people built a business that runs without the owner)


👉 Subscribe to hear more stories, strategies, and secrets that top contractors use to grow their home improvement businesses and enjoy more success, wealth, and freedom.


Additional Resources:

⚡ Get your tickets for Accelerate LIVE! 2026 before we’re sold out! And use code PODCAST26 for $100 off. Go here: https://thewealthycontractor.com/events/accelerate-live 

⚡ Learn more about The Wealthy Contractor Success Society: https://thewealthycontractor.com/coaching/success-society 

⚡ Get Brian’s book, The 7 Secrets To Becoming A Wealthy Contractor, for FREE (just pay shipping). Visit https://www.TheWealthyContractor.com/

⚡ Follow us on social media:

Facebook: https://www.facebook.com/TheWealthyContractor

Instagram: https://www.instagram.com/TheWealthyContractor/

LinkedIn: https://www.linkedin.com/company/TheWealthyContractor/

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The Wealthy ContractorBy Brian Kaskavalciyan

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