What I Wish I Knew: Lessons from Vacation Rental Leaders

In this compilation episode of The Vacation Rental Show, host Lynell Gordon explores the hard-won wisdom of industry veterans who share their most expensive early mistakes. Jonathan Fonvielle reveals why being selective with homeowners matters more than chasing revenue, Scott Leggat emphasizes that advocacy must be proactive rather than reactive, and Adam Knight discusses the dangers of scaling too quickly without focus. From the wrong homeowner costing more than lost revenue to regulatory battles being won before they start, these leaders share the hindsight lessons that could save new operators years of struggle and significant financial loss. This episode is sponsored by Bluetent.

In this compilation episode of The Vacation Rental Show, host Lynell Gordon examines the critical lessons that industry veterans wish they had learned earlier in their careers, featuring insights from leaders who built successful businesses through both triumphs and costly mistakes.

What you'll learn:

Jonathan Fonvielle's homeowner selection matrix: why the right homeowner with the wrong house beats the wrong homeowner with the right house every time
How to identify green flags versus red flags in potential homeowner partnerships before operational problems emerge
Scott Leggat's advocacy imperative: why regulatory protection must be built into business strategy before threats appear in your market
The timeline reality of regulatory battles and why reactive advocacy almost always fails to prevent damaging restrictions
Adam Knight's scaling wisdom: how rapid growth without focus and systems creates operational chaos that undermines long-term success
The importance of targeted market positioning versus trying to serve everyone and connecting with no one
Why saying no to revenue-generating opportunities often protects profitability and operational sanity better than growth-at-all-costs strategies
How community collaboration beats competition thinking for sustainable business development

The episode features Jonathan Fonvielle, a veteran vacation rental operator who built a powerhouse family business; Scott Leggat, Director of Government Advocacy at Inhabit and industry advocate; and Adam Knight, a seasoned hospitality professional who transitioned from hotels to short-term rentals. Together, they provide a candid examination of the missteps, oversights, and expensive lessons that ultimately shaped their successful approaches to property management, advocacy, and business scaling.

This episode is sponsored by Bluetent .

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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.

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