VRS636 - Scaling Smart: How to Spot the Owners Who’ll Sabotage Your Growth

Dennis Goedheid is back on the show, and we dive deep into one of the most overlooked yet mission-critical aspects of running a property management company - identifying and saying no to the wrong owners.
We also chat about his journey with Casiola’s international expansion, his team’s DEI award win at VRMA, and why scaling means getting crystal clear on your homeowner criteria.
Whether you're just starting out or managing hundreds of properties, this conversation is packed with real-world insights from someone who’s learned the hard lessons - and is still smiling!
🧭 What We Cover:
- Why Casiola won VRMA’s DEI Impact Award (and what it really means in daily operations)
- Casiola’s growth from Orlando to Aruba, Spain, Dubai, and beyond
- What makes an “emotionally attached” homeowner a red flag
- The crucial difference between hospitality and servitude
- Setting expectations early - and why your owner contract must be non-negotiable
- Why the feeling of dread when an owner emails, should never be ignored
- How to empower your team with red flag guidelines
- Real stories from Heather and Dennis on their “Margot moments”
🔥 Quotable Moments:
“If nobody on the team wants to answer the phone when a certain owner calls… that’s your red flag.” – Dennis Goedheid
“The best thing we ever did was create a list of red flags and empower the team to use it.” – Dennis Goedheid
“We learned early on: you don’t fire properties - you fire owners.” – Heather Bayer
📌 Links & Resources:
🙌 Connect with Dennis:
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