In this episode, I’m joined by Stephanie Pipkin — a longtime ZenMaid customer, cleaning industry expert, and now an important part of the ZenMaid team — for a deep and wide-ranging conversation about business growth, decision-making, and the evolution of ZenMaid.

We dive into:

• How Stephanie and I first connected — from customer to collaborator to advisor
• The psychology of spending — how perceptions of value shift as you grow personally and professionally
• ZenMaid’s unique position in the market — why we focus on value over just affordability
• The pain of switching software — and why so many maid services stay stuck with tools they don’t love
• How ZenMaid locks in customers by targeting 4–7 cleaner businesses — and helps them scale to 8–12 and beyond
• The importance of content and education — how ZenMaid became a media company that monetizes through software
• What happens if the ZenMaid software disappeared — and how we’ve built resilience beyond our tech
• The massive upside of treating ZenMaid as a platform — not just a tool
• How pricing strategy decisions were made — and why bringing in outside experts (like Jules from Roast My Pricing Page) was crucial
• Understanding risk and expected value — and how poker taught me to think like a CEO
• Why most big moves today are about reducing downside risk, not chasing upside
• How ZenMaid invests resources across marketing, sales, and product teams
• The “80/20 Rule” obsession — why it’s referenced in every ZenMaid meeting and how it powers faster decision-making
• Balancing customer feedback and internal vision — why not every feature request gets built, and how we stay focused on our Ideal Customer Profile (ICP)
• The evolution of the cleaning industry — how younger entrepreneurs are changing the market and what that means for software like ZenMaid
• Thoughts on AI and automation in the cleaning industry — and why newer companies may underestimate the complexity of real-world operations
• The “cruise ship vs. speedboat” metaphor — why ZenMaid’s stability is a strategic advantage
• How Stephanie created a trusted audience by providing value first — and how that mirrors ZenMaid’s success with content marketing

Throughout the conversation, we also touch on personal philosophies around business building, resilience, team building, and how tiny consistent actions (“brick by brick”) have compounded over more than a decade at ZenMaid.

Mentioned Links:

🧹 ZenMaid: ZenMaid.com

🇺🇸 Follow my entrepreneurial journey: TheAmaricanDream.com

🧼 Stephanie’s consulting and content: SereneClean.com + the Filthy Rich Cleaners Podcast

Thanks for listening!

If you have questions you want answered in the next episode, drop a comment or message us.