FEATURED GUEST

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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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)

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FEATURED GUEST

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)

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FEATURED GUEST

Glenn Williamson

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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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EPISODE SPONSORS

⁠The Wooster Brush Company⁠

⁠⁠⁠The Commercial Painting Industry Associate⁠⁠⁠ (CPIA)

DC Marketing Group

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FEATURED GUEST

Zach Kenney

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Is social media just a thing the kids do these days? Not for Zach Kenney with ZK Painting. He's sold over $9 million in painting jobs on Instagram alone without spending a dollar on ads. He's known for his high-end residential work, but his methods apply to any painting contractor who wants to grow their business without blowing their budget.

What started out as a punishment turned into a career, and quickly the love of the work grew into a very profitable business. In this show, we go over some of the pivotal things that turned Zach into a CEO and social media savant.

-How to know your audience and when to go after your niche and let go of market space that's not a fit.

-Knowing your paints and your finishes improves your products

-What to focus on with social media and it's not likes

-What actually is "influencer marketing" and is it worth it?
-The metrics to focus on that lead to actual sales

-Content going viral vs content that makes you money and how they're different.

-What equipment do you actually need to make content for social?

Social media can be used for a million things, and it can get overwhelming fast when you think about all the things you COULD do, but Zach breaks it down and goes over just what you SHOULD do. You don't need a team, you don't need a million followers, you don't need a camera crew, you just need to keep your customer in mind and make something. In just a few years, Zach made over $9 million in sales without spending a dime. This podcast goes over all the things he did that you can easily do too!

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⁠ZK Painting

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EPISODE SPONSORS

⁠The Wooster Brush Company⁠

⁠⁠⁠The Commercial Painting Industry Associate⁠⁠⁠ (CPIA)

⁠⁠⁠A David Creation⁠⁠⁠ (ADC)

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FEATURED GUEST

Linnea Blair

ABOUT

Linnea Blair has influenced and improved the health of several business owners, including your hosts David and Aaron. In this episode, Linnea Blair shares her journey of working with painting contractors, starting in 2002 when she created a coaching program for members of the PDCA (Painting and Decorating Contractors of America), where she immediately got 18 sign-ups. She explains how understanding financials, particularly estimating accurately and knowing key numbers, was pivotal in helping contractors like Mike Chism (David’s father) grow and improve profitability. 

She emphasizes the importance of business owners knowing their financials — even if they have help — and consistently reviewing budget-to-actual comparisons. In this episode we cover:

-How to set appropriate benchmarks that are realistic and growth-minded

-What numbers are important, and what numbers are misleading that could be ruining your profit margin

-What are optimal profit margins, and what metrics do you focus on to get there

-How to build a budget that’s accurate and up-to-date

-What your standard operating costs should be if you’re scaling correctly

She outlines crucial financial metrics: revenue, gross profit margin (ideally 45-50% for painting contractors), and net operating profit (targeting 20-25% before owner’s compensation). Linnea defines gross profit clearly, separating direct costs from variable expenses and overhead for better benchmarking. She stresses that solid gross profit and financial literacy are key to both profitability and scalability.

Additionally, she discusses maintaining healthy cash reserves (three months of expenses) and gives a balanced view on business debt, advocating caution and readiness before leveraging it for growth.

The episode can really be summed up with this: owners don’t need to love financials, but they must understand and take ownership of their numbers to ensure their businesses thrive. Tune in to hear all the broken-down ways ⁠Advisors on Target⁠ can help your business grow!

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Advisors on Target

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⁠⁠⁠Podcast website⁠⁠⁠

EPISODE SPONSORS

⁠The Wooster Brush Company⁠

⁠⁠⁠The Commercial Painting Industry Associate⁠⁠⁠ (CPIA)

⁠⁠⁠A David Creation⁠⁠⁠ (ADC)

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FEATURED GUESTS

Brian Jurgens and Tim Kenney

ABOUT

Boston is known for its unique architecture and rich history; today we get to meet the family that’s spent the last half century painting it all! The legendary Tim Kenney and Brian Jurgens.

This fourth-generation company started by selling paint door to door during the Great Depression. When your business has thrived for that long, you’ve had to not only adapt but also tread in waters where no one has gone before. We get into how Tim was convinced to step into the family business and how later on the torch got passed down to Brian.

Being based in New England, W.T. Kenney has had painting jobs like the President’s suites at Gillette Stadium, lawyers offices for the Celtics, revolutionary war buildings, a 100’ flagpole on the Lexington battle green, Harvard, and so many more.

It wasn’t an easy road; Brian would spend the days painting and at night change into his school clothes, going for his MBA. Tim had other aspirations until his dad pulled him aside and asked him to join the family business, a question that would change his life.

In this episode we cover:

- The financial changes when you move into ownership

- The little things Tim does to improve customer relations

- How to transition a family business down without hindering progress

- Will the fourth generation pass the business off to the fifth generation?

- Brian’s plans for the future as the new face of the company

They’ve been featured on NPR and the Boston Globe for their work, all while maintaining family values and staying true to what they stand for. Tune in for the rest of the episode and hear the incredible stories on not only how they managed business but also all of the incredible projects they’ve been a part of.

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⁠W.T. Kenney Co.

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EPISODE SPONSORS

⁠The Wooster Brush Company⁠

⁠⁠⁠The Commercial Painting Industry Associate⁠⁠⁠ (CPIA)

⁠⁠⁠A David Creation⁠⁠⁠ (ADC)

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FEATURED GUEST

Alec Kinard

ABOUT

Hundreds of employees, over a hundred million in revenue, and the need for a new CEO at Graydaze Contracting and the person to fill the role is none other than 29 year old, Alec Kinard.

So many people associate CEO’s with grey hair but as Alec proves, age is just a number when you lead with trust and integrity.

In this episode Alec goes into his short but vast history in contracting. Some of the things he covers are:

-How to lead people older and more experienced

-The roles of a CEO and the three key things to pay attention to

-Habits and groups to be a part of to stay on top of your life

-The future of Graydaze Contracting and the contracting industry

-Top advice for the next generation of leaders

More about Graydaze:

Graydaze Contracting specializes in the installation of architectural paints, specialty coatings, high-performance sealants, resinous flooring, and industrial slab repair—all under one roof. Their single-source approach simplifies what is often a complex process, eliminating the need to coordinate multiple finish trades. The result? A streamlined, efficient solution that saves both time and money.

Their rapid success stems from our ability to professionally manage a wide range of projects, meet tight deadlines, and deliver durable, high-quality finishes that stand the test of time, all under the leadership of Alec Kinard!

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Graydaze Contracting

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⁠⁠⁠Podcast website⁠⁠⁠

EPISODE SPONSORS

⁠The Wooster Brush Company⁠

⁠⁠⁠The Commercial Painting Industry Associate⁠⁠⁠ (CPIA)

⁠⁠⁠A David Creation⁠⁠⁠ (ADC)

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FEATURED GUEST

Matt Adams

ABOUT

Tired of hearing about the magic of Google? Or maybe the “magical” 5 steps to grow your business through SEO? That’s probably because we learn at a young age that magic is a bad business word that really means smoke and mirrors or give me money and I’ll tell you a weak secret.

Believe it or not, you don’t have to learn a foreign language to use Google to help grow your business. Simple things like, what words you use in your business profile to be better recognized in search engines and how tools you can use to check areas you’re missing that are hurting your Google ranking. 

Now meet SEO expert from Linda.co, Matt.

Matt started in marketing about 12 years ago. In those years he’s been involved in full-stack marketing and growing companies using local search words, Google profiles, websites, and anything and everything to help turn leads into customers.

This is where we learn about the company, Linda.

Linda is a company that exists to master local SEO for all businesses like plumbers, HVAC, painters, and more. Matt breaks down how to grow your search authority against your competitors so that when Googled, your company shows up first. It's not rocket science that ranking higher will get more clicks, more clicks turn into more leads, more leads turn into more customers, and...well you get it.

This show covers:

-Google business profiles and how to use them to be seen

-Maximizing some basic areas like using the correct language to exponentially grow your search position

-Having the proper data and the links that the internet looks for to be validated

-Optimizing your Google URL to improve your rank

-Internet tools that you can use to see if you’re compliant or not to improve your keyword success

-Your company address matters to Google more than you know

-Having smarter content, not just more

Matt goes on to explain how you can make sure your company can comply with Google’s terms of service and so many basic, low-hanging fruits that so many businesses are missing. Everyone knows that if you’re not visible, you’re not getting customers but what people don’t know is how easy and important some of these basic things are. 

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⁠Linda.co

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EPISODE SPONSORS

⁠The Wooster Brush Company⁠

⁠⁠⁠The Commercial Painting Industry Associate⁠⁠⁠ (CPIA)

⁠⁠⁠A David Creation⁠⁠⁠ (ADC)

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FEATURED GUEST

David Franco

ABOUT

Ready to take your team to the next level? In this episode, David Franco of Protiv drops some serious knowledge on how to build a powerhouse team that delivers every time. 

From scaling a $10M business to tackling labor management, David reveals how Protiv’s performance-based solutions turn ordinary workers into top performers. Think creative contests, tech-driven performance tracking, and recognizing your team’s wins in ways that fuel motivation. 

Tune in to the episode for dynamic tips that will transform your crew into a high-performing, unstoppable force that keeps your business thriving. 

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Protiv

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⁠⁠⁠Podcast website⁠⁠⁠

EPISODE SPONSORS

⁠The Wooster Brush Company⁠

⁠⁠⁠The Commercial Painting Industry Associate⁠⁠⁠ (CPIA)

⁠⁠⁠A David Creation⁠⁠⁠ (ADC)

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FEATURED GUEST

Aaron Cooper

ABOUT

Imagine a sales team that never sleeps, a receptionist with infinite patience, and a marketing department fueled by data-driven insights—all rolled into one incredibly efficient AI.  That's the power of Sameday AI.

This episode features Aaron Cooper, the visionary behind Sameday AI. Find out how this innovative technology is helping businesses achieve seamless operations and exponential growth. Learn how Sameday seamlessly integrates with existing software, adapts to your unique needs, and continuously improves, driving booking rates up to an impressive 90%+ for many clients. Discover the secrets to maximizing efficiency and exceeding customer expectations.

Tune in to the full episode to hear Aaron's insights and discover how Sameday AI can revolutionize your operations!

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Sameday AI

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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!