Building a Vacation Rental Business From Zero to 57 Properties with Nomadic Vacays
Update: 2025-12-23
Description
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.
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👉 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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