The Day I Decided to Hang Up the Tool Belt
It was a brutally cold January morning in 2024. I was standing on a roof in Maple Grove at 7 AM, wind cutting through my jacket, watching my crew struggle with frozen shingles. I realized I was more tired of the business side than the physical work. The endless paperwork, insurance headaches, chasing payments, and worrying about keeping good guys employed year-round had worn me down.
That night I told Anna I was done running the crew. I wanted to write instead — to pass on what I’d learned the hard way so other homeowners wouldn’t have to.
I've been on that roof. Let me save you the trip.
The Reality of Running a Small Exterior Crew
Owning Fletcher Exteriors LLC for eight years was one of the hardest and most rewarding things I’ve ever done. I started with one truck and grew to a solid four-man crew. We did good work. I was proud of that.
But the business side was relentless:
Cash flow nightmares when big jobs had slow payments.
Finding reliable workers in a tough labor market.
Insurance premiums that kept climbing.
The constant stress of weather delays in Minnesota.
Liability worries every single day.
I loved the actual work — hanging siding, building decks, solving problems on site. I hated the rest.
What I Missed and What I Didn’t
I miss the camaraderie of a good crew. There’s nothing like finishing a tough job on a Friday afternoon, covered in dust and sweat, and sharing a cold drink while looking at quality work.
I don’t miss:
5 AM alarm calls in January.
Customers who ghost you after you’ve done 90% of the job.
The constant battle to find good help who show up and care.
Doing estimates at 7 PM after already working a full day.
The Moment That Sealed It
There was one particular job — a big re-side in Edina. The homeowner kept changing their mind, payments were late, and the weather turned ugly. I realized I was spending more time managing stress than doing the craft I loved. That night I sat in my garage looking at my “mistake bucket” and decided I wanted to teach instead of just fix other people’s problems.
My wife Anna, an elementary teacher, supported the shift completely. She’d seen how the business was eating me up.
What Writing Allows Me to Do
Now I get to focus on the part I loved most: sharing real knowledge. No more chasing invoices. No more worrying if the next big snowstorm will shut us down for two weeks.
I can:
Write deep, useful articles without rushing.
Help thousands of homeowners instead of dozens per year.
Spend more evenings with Aaron and Lucy.
Keep my hands busy with woodworking and smoking brisket on weekends.
The knowledge I gained over 400+ homes doesn’t disappear. It just gets shared differently.
Lessons I Learned Running a Crew
Details matter more than most people realize. The difference between a good job and a callback is usually in the flashing and sealing.
Good people are everything. A reliable crew is worth more than any tool or truck.
Communication prevents 90% of problems. With customers and with your team.
You can’t control the weather. Plan for it and build buffers.
Price honestly. Cheap work usually ends up expensive for everyone.
Life After the Crew
I still climb ladders. I still help neighbors with projects when I can. But now my main job is writing these articles — trying to give you the straight talk I wish more homeowners had before they hired contractors.
My garage still smells like sawdust and stain. The offset smoker is still my weekend therapy. And that “mistake bucket” continues to grow with new teaching examples.
Why I’m Sharing All This
I want Dean’s Ladder to be different. Not another marketing site pushing products. Not another fluffy blog. Just a reliable voice from someone who’s actually done the work.
If you’re a homeowner trying to make smart exterior decisions, I’ve been where you are — looking at an estimate, wondering if you’re about to get taken for a ride. I’m here to help you avoid the expensive lessons I watched too many people learn.
To my fellow contractors still in the trenches: I see you. The work you do matters. Keep doing it right.
And to everyone reading: Thanks for letting me share what I’ve learned. There are a lot more stories and practical guides coming.
Stay warm. Stay dry.
— Dean
No notes on this sheet yet.