Building a Multi-Country Vacation Rental Empire with Christian Gissing - Vacation Rental Show
Update: 2025-11-18
Description
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:
- How to harness personal energy in your first hour each day to impact your entire team's performance and culture
- The branch manager program model that allows partners to leverage your systems while managing local operations independently
- Why building a business designed for exit creates better operations, margins, and sellability regardless of your actual plans
- The critical importance of firing quickly when employees violate core values instead of nurturing people who won't change
- How to identify the specific type of entrepreneur who will flourish with your business model in any market
- Practical steps for navigating international expansion including taxation, labor laws, and local partnerships
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.
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👉 Fame Host - https://bit.ly/hwg-podcast
👉 iheartradio - https://ihr.fm/3Z8qqlg
👉 RSS - https://feeds.fame.so/the-vacation-rental-show
The Vacation Rental Show is handcrafted by our friends over at: fame.so
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.
Check out the three most downloaded episodes:
- Vacation Rental Stories: Episode 63 - Driving Innovation and Partnership
- Homeowners Become Family with Michael Godfrey, Owner of Michael’s Vacation Rentals
- Life in Maui as a Property Manager with Scott Jordan, Owner of Maui Life Realty
Are you a vacation rental industry leader looking to share your expertise? We're seeking innovative voices to join our conversation about growing and scaling vacation rental businesses.
The Vacation Rental Show reaches thousands of property managers worldwide. We're particularly interested in perspectives on:
- Scaling your vacation rental portfolio
- Optimizing guest experiences
- Revenue management strategies
- Industry trends and market insights
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