In this episode of the Window Cleaning Millionaire Podcast, Ryan breaks down one of the most common and confusing questions for service business owners: when to hire managers and in what order.

Fresh off the Christmas lights season, Ryan shares real numbers, real scripts, and real outcomes from implementing outbound calls to past customers. He explains how a simple call center strategy added nearly two thousand dollars in booked work in just a few days and why this system will scale significantly as more salespeople are added.

From there, the episode dives deep into hiring strategy. Ryan walks through the exact order he recommends hiring key management roles, including office manager, operations manager, and sales manager. He explains what revenue levels make sense for each hire, how to structure compensation, and the biggest mistakes owners make when hiring too early or too late.

This episode is packed with tactical advice for owners who feel overwhelmed, stretched thin, and unsure how to buy back their time without creating financial stress.

Most window cleaning businesses do not fail because the owner is bad at business.

They fail because the owner quits too early.

In this episode, Ryan breaks down the real reason businesses win or lose, and it has nothing to do with being smarter, starting with more money, or having perfect systems.

Ryan shares what the early years of Reach Window Cleaning actually looked like. Counting cash to pay bills, slow seasons, bad months, bad hires, failed marketing, and doing everything himself. What looks like fast success from the outside was built on years of grind that most people are not willing to endure.

If you are in year one, two, or three and questioning whether this is worth it, this episode is for you.

In this solo episode, Ryan records the Monday before Thanksgiving and reflects on gratitude—not in a fluffy way, but as a practical leadership tool for service business owners.

He talks about a brutally rainy week in Arizona that tanked what should’ve been a huge revenue week, how his team handled it, and why gratitude kept him from panicking or making desperate decisions.

Ryan also shares how a $60K mentor (Keaton “The Muscle” Hoskins) drilled gratitude and time management into him, why he’s recommitting to those habits, and how you can use gratitude to zoom out and remember how far you’ve really come.

Instagram: @ryanthewindowcleaner

DM the word “podcast” if you want help growing your window cleaning, pressure washing, or Christmas light business, or if you just have questions and want to connect.

In this episode, Ryan sits down with longtime friend and marketing expert Weston Willbank, founder of WBNK Marketing. Weston runs ads for window cleaning, pressure washing, Christmas lights and dozens of other home service companies. Together, Ryan and Weston break down exactly what is working right now in Facebook and Instagram ads, why old strategies no longer work, and how simple tweaks can dramatically lower your cost per lead.

The conversation takes a deeper turn into entrepreneurship, mindset, mentorship, and the importance of upgrading your environment. Weston shares the full story of how he left a small town making 10K months and now runs an 80K per month agency. He also opens up about taking big risks, moving into a much better neighborhood, doubling revenue in a year, and the role his wife played in believing bigger.

This episode is packed with tactical strategies for ads, lead follow up, funnel structure, offer creation, and upselling. It also includes practical mindset shifts that help owners grow faster without burning out.

Website: WBNKMarketing.com

Email: weston@wbnkmedia.com

Tell him you came from Ryan’s podcast for a special rate.

Go High Level (for funnels and follow up)

$100M Offers and $100M Leads by Alex Hormozi

Ryan’s coaching program for window cleaning and home service owners

DM “PODCAST” to @RyanTheWindowCleaner on Instagram to learn about one-on-one coaching and the group program helping over 40 owners scale their businesses.

In today’s episode, Ryan sits down with Josh Schiffman, a seasoned entrepreneur who helped build an eight-figure pest control company, led top-performing sales teams, and developed thousands of reps in the door-to-door world. Josh dives deep into the failures, formative moments, and surprising experiences that shaped him, starting all the way back to selling chocolate bunnies as a kid.

Josh shares the turning points that pushed him toward leadership, the strategies behind creating route density, and the importance of serving customers beyond the basic transaction. He also breaks down what he would do today if he had to start a small service business from scratch. This conversation is full of tactical insights, psychology, storytelling, and real numbers that any home service founder can benefit from.

If you want to learn how to grow a service business, train a sales team, build culture, or create customer experiences that multiply revenue, this episode is packed with practical value.

Email: josh@mytrebos.com

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In this episode, I break down why I have decided to transition our window cleaning company from one man crews to two man crews. For years, the one man model made perfect financial sense. It maximized output, required fewer people, and helped us grow quickly. But with rapid scaling, increased ladder injuries in the industry, and the complexity of managing more trucks, the risk equation has changed.

I walk through the three main reasons behind the shift: safety, scalability, and culture. I also explain how the new pay structure will work, what our capacity goals will be, and how this change positions us for a major 2026 growth year. Whether you run one man crews now or have been thinking about switching, this episode will give you a full look at the pros and cons of each model and the real numbers behind our decision.

In this powerful and unfiltered conversation, Luke Abbott joins the show to break down how he grew All Clean Power Wash from a one man side hustle to nearly three million dollars in annual revenue. Luke’s journey is one many entrepreneurs will recognize. He went from working long days as a garbage man to grinding nights and weekends, missing dinners, sacrificing sleep, and pushing himself beyond burnout to pursue something bigger for his family.

Luke shares the honest truth about what it takes to scale, including marketing strategies that actually work, the importance of leveling up your leadership, why your team culture matters more than you think, how to handle debt and financial pressure, and what most small business owners get wrong when hiring.

This episode dives deep into mindset, discipline, systems, risk taking, personal growth, and the realities of building a multi million dollar service company. Luke’s vulnerability and transparency make this an episode every entrepreneur should hear.

In this episode of The Window Cleaning Millionaire Podcast, Ryan pulls back the curtain on a wild week that combined inspiration, stress, and some major wake-up calls.

Fresh off a trip to Los Angeles to visit a $5 million window cleaning company, Ryan shares the game-changing outbound calling strategy that’s driving their massive growth — and how he plans to implement it immediately in his own business.

But that’s not all. When tragedy struck back home with a serious employee ladder accident, it reminded him (and all of us) why cutting corners on things like workers’ comp and safety is never worth the risk.

This one’s raw, honest, and packed with lessons on leadership, scaling, and protecting what matters most.

If this episode hit home, take two minutes to leave a review on Apple Podcasts — it means the world and helps the show reach more service business owners like you.

Tag @ryanthewindowcleaner with your biggest takeaway.

Ready to scale your business faster (and safer)? DM “Podcast” to learn more about Ryan’s coaching program.