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Yale Rosen

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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.

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Risk Strategies

Yale on LinkedIn

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⁠⁠⁠Podcast website⁠⁠⁠

Request a FREE 1-Hour Consultation with David Chism

EPISODE SPONSORS

⁠The Wooster Brush Company⁠

⁠⁠⁠The Commercial Painting Industry Associate⁠⁠⁠ (CPIA)

⁠⁠⁠A David Creation⁠⁠⁠ (ADC)

If you enjoyed this episode, remember to like, share, and subscribe!

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Annie Newton

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In this episode of the Commercial Painting Podcast, Annie Newton shares her journey from running a successful painting company in Washington to leading ProfitWorks, a firm that helps painting and service-based businesses grow through fractional CFO services and remote staffing solutions. With over two decades of experience in the trades, Annie offers profound insights on scaling smart, building effective financial back offices, and leveraging remote talent the right way.

She breaks down the differences between controllers and CFOs and when a business needs each. Annie also discusses the common “Death Valley” businesses that hit between $3–5 million in revenue—and how having the right systems, mindset, and talent can help push through to the next level.

Listeners will learn:

• The right time to bring in fractional CFO or controller support
• How to restructure your back office for growth
• The pros and cons of hiring remote (especially offshore) talent
• Why leadership buy-in is essential for remote hiring success
• How to avoid common pitfalls with offshore workers—like poor accountability or lack of ROI
• Why culture, clarity, and communication are essential for leveraging global teams

Whether you’re trying to offload tactical tasks, improve financial visibility, or reimagine your org chart, Annie’s insights are invaluable for leaders looking to scale their painting or trade business with confidence.

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ProfitWorks

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⁠⁠⁠Podcast website⁠⁠⁠

EPISODE SPONSORS

⁠The Wooster Brush Company⁠

⁠⁠⁠The Commercial Painting Industry Associate⁠⁠⁠ (CPIA)

⁠⁠⁠A David Creation⁠⁠⁠ (ADC)

If you enjoyed this episode, remember to like, share, and subscribe!

FEATURED GUEST

Glenn Williamson

ABOUT

In this episode, Glenn Williamson, founder of New Haven Painting, shares his journey from humble beginnings to running a respected painting business known for its integrity, precision, and customer care. Glenn opens up about how he built New Haven Painting from the ground up, the importance of relationships in the trades, and how word-of-mouth marketing continues to be a pillar of his growth strategy. What makes him unique is the technology he uses to grow his business and the data points he pays attention to.

In this episode he covers:

-How to filter through leads to find your optimal customer

-Strategies on how to find potential customers to grow your business

-Must have technology to manage and organize deals

-How to use a CRM to move a bid into a customer

-The tech stack he uses to find, convert, and keep customers

-When data can be bad and lead to costly decisions

Whether you’re a fellow tradesperson or just love a good small business story, this episode delivers actionable wisdom and inspiration. Adding software to your process can be scary, but Glenn shares how you can not only do it but also use these programs to streamline your business.

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New Haven Painters

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⁠⁠⁠Podcast website⁠⁠⁠

EPISODE SPONSORS

⁠The Wooster Brush Company⁠

⁠⁠⁠The Commercial Painting Industry Associate⁠⁠⁠ (CPIA)

DC Marketing Group

If you enjoyed this episode, remember to like, share, and subscribe!