What if the smartest way to start in a crowded market isn't to start from scratch?
In this episode of Building It, I sit down with Dennis Goedheid, the founder of Casiola, who took an unconventional path. He bypassed the initial grind by acquiring a 20-property business to get his start.
We break down his playbook for buying a business, the brutal honesty of his first-year failure (with negative growth), and the standardization strategy he used to scale to over 550 properties. This is a masterclass in creative and resilient entrepreneurship.
Connect with Dennis:
LinkedIn: https://www.linkedin.com/in/dennisgoedheid/
Casiola: https://www.casiola.com/
Chapters:
00:00:00 - Intro: The Founder's Shortcut to Starting an STR Business
00:01:15 - Scaling Global: Taking a US Vacation Rental Brand to Europe
00:02:22 - The Onboarding Filter: Setting Property Standards for Your STR Brand
00:05:20 - The Scaling Mandate: Why You Must Standardise Your Operations
00:08:13 - Startup Strategy: Buying a Vacation Rental Business vs. Building From Scratch
00:09:45 - The Vacation Rental Myth: The Brutal Reality of "Passive Income"
00:11:36 - The Buy vs. Build Playbook: A Shortcut for STR Entrepreneurs
00:12:17 - Acquisition 101: How to Value & Buy a Property Management Company
00:20:31 - Due Diligence Tip: The Power of Property Location Density
00:23:27 - The First-Year Failure: Overcoming Negative Growth as a Founder
00:31:55 - Accidental Branding: How a Simple Colour Built Their Brand Identity
00:37:25 - Founder's Final Playbook: Creative Financing & Strategic Partnerships
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Disclaimer: The content shared on this YouTube channel, Podcast, or associated posts reflects personal opinions and insights. This content is not intended as legal, financial, or investment advice. Always consult with licensed professionals before making decisions. The hosts and guests disclaim liability for any consequences of using this content. Actions taken should be based on your personal due diligence.
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