Building a Vacation Rental Business From Zero to 57 Properties with Nomadic Vacays

Taylor Moore and Danielle Giancola built Nomadic Vacays from zero to 57 properties in Naples, Florida in just over four years, starting during the COVID-19 pandemic after relocating their entire family from New Jersey. Their unconventional approach prioritized infrastructure over gradual scaling, building systems designed for 100 properties from day one. In this episode of The Vacation Rental Show, Taylor and Danielle share why they insisted on implementing Streamline, how their 22-step onboarding process with video tutorials makes operations plug-and-play for any team member, and the immersive 18-month strategy where they worked 16-hour days learning every aspect of the business from the ground up. They discuss the brother-sister partnership dynamics that make their collaboration work, how they help family members create service businesses within their business ecosystem, and the hard lesson they learned about partnership alignment when their initial third partner's vision didn't match theirs. This episode is sponsored by Rental Guardian.

In this episode of The Vacation Rental Show, host Lynell Gordon speaks with brother-sister duo Taylor Moore and Danielle Giancola, founders of Nomadic Vacays, about building a vacation rental business from scratch during COVID-19, prioritizing infrastructure before growth, and creating systems that make operations plug-and-play.

What You'll Learn:

Why building infrastructure for 100 properties from day one accelerates growth even when you start small
The 18-month immersion strategy where founders work 16-hour days learning every business aspect firsthand
How a 22-step onboarding process with video tutorials eliminates dependence on key personnel
Brother-sister partnership dynamics and the good cop bad cop approach to managing family employees
Creating service businesses within your business ecosystem for family members with different passions
The partnership alignment mistakes that led to their third partner departing and how to avoid them
Balancing automation and templates with personalized guest communication touches
Why vendor selection and relationship management took years to refine properly
Proactive communication strategies that reach out to guests and owners before they contact you
Growing into technology features over time rather than activating everything immediately
The corporate careers they left behind to build a vacation rental legacy
Why they showed up at 4 AM when guests got locked out instead of sending a service provider

Taylor Moore and Danielle Giancola are the brother-sister founders of Nomadic Vacays, managing 57 vacation rentals in Naples, Florida. They left high-level corporate careers in sales and consulting in New Jersey during COVID-19 to relocate their entire family and build a vacation rental business from scratch. Despite being told by Streamline initially that they were too small for the platform, they insisted on implementing enterprise-level systems from day one, understanding that having everything in one central location would become their competitive advantage. They partnered with Thorough Accounting, Rental Guardian, and RingCentral to create integrated back-end functions designed for 100+ properties even when they were just starting. Their first 18 months involved working side-by-side 16 hours daily, learning every operational aspect personally so they could train teams effectively. They've built comprehensive video tutorial systems covering all 22 steps of property onboarding, making operations plug-and-play for team members with zero experience. While they've experienced turnover and learned hard lessons about partnership alignment, their infrastructure-first approach has enabled sustainable growth while maintaining genuine hospitality and personal connections.

This episode is sponsored by Rental Guardian.

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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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