Rebuilding Through Adversity: Angie Leone's Journey from 60 Properties to One After the Maui Fire
October 14, 2025
In this episode of The Vacation Rental Show, host Lynell Gordon sits down with Angie Leone, CEO and founder of Coconut Condos in Maui, to explore one of the most heart-wrenching yet inspiring stories in vacation rental history. From managing 60 properties with a staff of 13 and being named SBA Women-Owned Business of the Year in May 2023, to losing 45 properties, her office, and warehouse in the Lahaina fire just three months later—two days before her planned business sale closed—Angie's journey embodies resilience, faith, and the power of non-negotiables. This conversation provides a roadmap for property managers on setting boundaries from day one, navigating catastrophic loss, knowing when to rebuild versus reinvent, and finding hope through unimaginable adversity.
This episode is sponsored by Streamline.
In this episode of The Vacation Rental Show, host Lynell Gordon speaks with Angie Leone, CEO and founder of Coconut Condos, about navigating the most challenging circumstances a property manager can face while maintaining faith, family priorities, and forward momentum.
What You'll Learn:
- How to set non-negotiables from day one that protect work-life balance as you scale Why preparing your business for your absence is essential before crisis hits
- The difference between rebuilding and reinventing after catastrophic loss
- How COVID prepared Angie for an even more devastating challenge with the Lahaina fire
- The critical importance of having a "board of directors" network before you need them The 5 F's framework (Faith, Family, Fitness, Freeze, Focus) for maintaining stability through crisis
- Why advocacy work requires recognizing seasons and knowing when to pass the baton
- How to model resilience and choice for your children while navigating business loss
- The role of community support during devastating circumstances
- When it's wise to pivot away from growth and embrace simplicity
- Why being under contract to sell doesn't guarantee the deal will close
- How to maintain morning and evening routines that keep you grounded during trials
- The value of removing yourself from day-to-day operations even during peak season
- Why some battles are worth fighting and others require strategic retreat Career pivots from property management to speaking, writing, and sharing hope
Angie Leone brings over 13 years of vacation rental industry experience, having founded Coconut Condos in 2011 with a single property and grown it to 60 properties with 13 staff members. Named 2019 SBA Maui Small Businessperson of the Year and 2023 SBA Women-Owned Business of the Year, she also founded PRMA (Professional Rental Managers Association) to fight discriminatory legislation in Hawaii during COVID. After losing 45 of 50 properties, her office, and warehouse in the August 8, 2023 Lahaina fire—two days before completing a business sale—Angie chose reinvention over rebuilding. She now manages their flagship bed and breakfast property with her husband while pursuing keynote speaking, writing her first book, and sharing messages of hope with property managers navigating their own seasons of adversity.
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👉 RSS - https://feeds.fame.so/the-vacation-rental-show
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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.
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
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