Years spent carrying shingles and serving homeowners taught me a few principles I still see today in business and wealth planning. Three have stayed with me.
1. Lift With Your Legs: Leverage What Makes You Strong
Great businesses often grow by playing to their strengths
In roofing, our strength wasn’t simply installing roofs well. It was building trust in an industry where trust was often thin. We introduced ourselves, explained how we’d protect landscaping before a tear-off, and made homeowners feel heard and valued. What looked like “good service” was actually a form of leverage—because relationships became a competitive advantage.
That lesson has stayed with me: businesses thrive when they stop fighting their design and start leveraging what makes them strong.
2. The Checklist Is King
Excellence begins to scale when what works repeatedly is made transferable.
My brother Allyn was a member of Strategic Coach long before I was. Returning home from one of his sessions, he handed me Atul Gawande’s book Checklist Manifesto. “Read this,” he said, “and let me know if you think we can use it.”
I devoured it.
Immediately, I started building checklists for every part of my work. Then I translated them into Spanish for my crew. Something changed almost immediately: errors dropped, consistency improved, and the team started offering ideas to improve the process itself. What began as an effort to avoid forgetting basics ended up creating space for innovation.
Checklists don’t replace creativity. They free us up from the mundane so that we can be more creative.
3. “The Customer Is Always Right Important”
John Wanamaker wasn’t far off.
Growing up, my brothers and I listened to a biography of John Wanamaker, the Father of American Retail. Wanamaker’s phrase that “the customer is always right” may be overstated, but it’s not far off. As I think about our many business owner clients, each of you knows your industry way better than I do. And because you do, you often know better than I and the rest of your customers do what we need from you. But I always admired the way business owners, including my brothers, wouldn’t let this knowledge go to their heads. Instead, they communicated respect, created confidence, and made people feel like they matter. I learned a lot from them, and I learn a lot from you.
Customers may forget details, but they rarely forget when you listen to them and show them you care.
Other Roofing Lessons I Still Carry
A few more lessons I learned on rooftops:
- Measure twice, cut once.
- Deferred maintenance gets expensive.
- Safety rules are often written in blood.
- The job isn’t done until the cleanup is done.
- Storms reveal weaknesses that sunny days conceal.
I have stories that go with each one of these, some hilarious, some painful, all timelessly wise. Business has a way of proving all these and more.
Your turn: A Question for Small Business Week
If you own a business, three questions may be worth asking:
- Where are you fighting your design instead of leveraging your strengths?
- What lives only in your head that belongs in a checklist?
- Are your customers merely served—or made to feel important?
Sometimes the oldest lessons still carry the most weight.
Even if they come wrapped in 60-pound bundles.
This material is provided for informational purposes only and is not intended as investment advice or a recommendation to take any particular action. Advisory services are offered through Keating Financial Advisory Services (KFAS) pursuant to a written agreement. Any examples discussed are for illustrative purposes only and do not guarantee future results.