The Vacation Rental Show
Building a Multi-Country Vacation Rental Empire with Christian Gissing
November 18, 2025
What happens when you build a property management company with the vision to operate in places you love while helping your closest friends achieve financial freedom? Christian Gissing, founder of True North Property Management, shares his 11-year journey from bootstrapping in Traverse City, Michigan, to managing properties across four countries including Jamaica, the UK, Bali, and Mexico. In this episode, Christian reveals his innovative branch manager program that functions like a franchise but with more extensive support, allowing partners to leverage all back-end systems while focusing on local operations and owner relationships. He discusses the hard lessons learned about firing quickly when core values are violated, building a business designed for exit whether you plan to sell or not, and why the first hour of your day determines your energy and leadership impact. Christian's philosophy centers on creating a life he doesn't need a vacation from and making his business bigger than himself by transforming team members' lives. His transparent approach to failure, growth, and multi-country expansion offers actionable insights for property managers ready to scale beyond their comfort zones. This episode is sponsored by RevMax.

Scaling a property management business across international borders while maintaining culture and quality seems impossible—until you meet someone who's done it. In this episode of The Vacation Rental Show, host Lynell Gordon speaks with Christian Gissing, founder of True North Property Management, about building a multi-country vacation rental empire that operates in the US, Jamaica, the UK, Bali, and Mexico while helping friends achieve financial freedom.


What you'll learn:


Christian Gissing founded True North Property Management 11 years ago in Traverse City, Michigan, with the vision to create a life he didn't need a vacation from. Starting from scratch with a bootstrap approach, Christian has expanded operations across four countries and is currently onboarding 800 units in Jamaica alone. His innovative branch manager program allows friends and qualified entrepreneurs to leverage True North's complete back-end infrastructure—technology, systems, human resources—while maintaining local market focus and owner relationships. Christian's leadership philosophy emphasizes self-perpetuating growth, where teams thrive with or without founder input.


In this conversation, Christian shares his "failed my way to success" philosophy and the hard lessons learned about protecting company culture. He explains why founders must fire themselves from operational roles to unlock business potential, how focusing on team transformation creates fulfillment beyond cash flow, and why making your first hour sacred for energy management impacts everyone you touch. Christian also discusses his involvement with Stakeholders, a rollup opportunity for property managers seeking liquidity events, and why thinking like you're building to exit transforms business quality immediately.


This episode is sponsored by RevMax.


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Previous guests include: Jim DeVos of Best Beach Getaways, Stacy Wesson of Cascara Vacation Rentals, Michael Friedman of The Simple Life Hospitality, Steve Caron of Inhabit, John An of TechTape, Jessica Gillingham of Abode Worldwide, Justin Ford of Breezeway, Mahwussh Alam of One Perfect Stay, Lisa Stinnett of Inhabit, and many more.

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