Summary / Intro

Most roofing contractors work hard for years assuming they’ll eventually sell their business or pass it on.

The reality?

Most businesses don’t sell — they simply shut down.

In this episode, I sit down with construction attorney Scott Calhoun to break down the four biggest business killers that quietly destroy roofing companies: divorce, disability, dissolution, and death.

These aren’t dramatic what-ifs. They’re predictable risks that can wipe out everything you’ve built if you don’t plan ahead.

We talk through real-world examples of contractors who didn’t have the right structure, agreements, or protections in place — and what you can do now to protect your company, your family, and your future. This episode is about building a business that survives real life, not just good years.

Show Notes

If your roofing business depends entirely on you, it’s more fragile than you think.

In this episode of The Roofer Show, Dave Sullivan is joined by construction attorney Scott Calhoun to discuss the Four Business Killers that end most contractor-owned companies long before retirement: divorce, disability, dissolution, and death.

They break down why most roofing businesses never sell and why failing to plan for these risks leads to forced closures, legal battles, and financial loss. Scott explains how proper entity structure, partnership agreements, buy-sell planning, and insurance can protect both the business and the people behind it.

This conversation isn’t about fear — it’s about foresight. With the right planning and systems in place, contractors can build businesses that withstand unexpected life events and continue operating without chaos. If you care about long-term stability, profitability, and protecting what you’ve built, this is a must-listen.

Takeaways

• Most roofing businesses don’t fail from lack of work — they fail from lack of planning
• Divorce, disability, dissolution, and death are predictable risks, not rare events
• Proper entity structure protects both the business and personal assets
• Partnership and buy-sell agreements prevent chaos during major life events
• Disability can be more financially damaging than death if not planned for
• A business that can’t survive without you isn’t a sellable or stable business

Chapters

00:04 – Understanding the Four Business Killers

09:41 – How the 4 Ds Impact Roofing Companies

25:12 – Real-World Contractor Scenarios

36:10 – Succession Planning and Business Continuity

42:42 – Disability Insurance and Risk Protection

Links Referenced in This Episode

https://theroofercoach.com

https://theroofercoach.com/resources

Companies Mentioned

SMA Support

Proline

👉 Download the free Roofing Business Success Audit at

theroofercoach.com/resources