Beyond Renewal: Smart Insurance Strategies for Contractors

FEATURED GUEST

Yale Rosen

ABOUT

Insurance is one of those topics every contractor needs but few want to dig into. In this episode, Aaron sits down with Yale Rosen, Risk Advisor at Risk Strategies, to break down the insurance essentials that commercial painting contractors should understand. Yale explains what matters, what to watch for, and how to work with a broker who actually adds value (instead of showing up once a year at renewal).

You’ll also hear:

• The difference between insurance and risk management.

• When smaller contractors can get by with direct-to-carrier vs. when it’s time to bring in a broker.

• How safety culture, claims handling, and deductible choices can impact premiums.

• Why shopping insurance the wrong way can hurt your pricing.

• The growing importance of cyber coverage and when it’s worth it.

And as a bonus, Yale shares his unique path from minor league baseball in the Padres organization to helping contractors nationwide protect their businesses.

Whether you’re new to commercial work or running a multimillion-dollar operation, this episode gives you practical takeaways to strengthen your insurance strategy.

Connect with our Guest
Risk Strategies

This Episode is Brought to You by:
Wooster Brush
DC Marketing Group
Commercial Painting Industry Association

Connect with Us
thecpia.com
commercialpaintingpodcast@gmail.com

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