Ever wondered if one spontaneous decision could completely change your career? That’s exactly what happened to Jayla Siciliano. While on vacation, she crunched the numbers on a short-term rental, saw its potential, and the next day, put in an offer on her first property.
In this episode of SmartStay Show, Jayla takes us through her journey from that impulsive purchase to building a thriving short-term rental business across multiple states. We dive into the challenges of managing properties remotely, the importance of building a strong local team, and how she scaled her co-hosting operation while maintaining high-quality guest experiences.
Jayla also shares how she overcame imposter syndrome, lessons from past entrepreneurial ventures, and why she’s now expanding into real estate development. Whether you’re a new investor or an experienced host, this episode is packed with insights and inspiration you won’t want to miss!
Things we discussed in this episode:
- Jayla’s Unexpected Start in STRs – How a vacation rental stay led to her first property purchase.
- Scaling a Short-Term Rental Business – Growing from a single property to managing multiple across states.
- Challenges of Remote Property Management – How she successfully operates rentals from across the country.
- Building a Strong Local Team – The importance of having reliable "boots on the ground."
- Overcoming Imposter Syndrome – Transitioning from a different industry and establishing credibility in STRs.
- The Role of Systems and Technology – Using tools like Breezeway and OwnerRez to streamline operations.
- Expense & Maintenance Management – The hidden complexities of managing costs and upkeep, especially in snowy climates.
- Co-Hosting and Owner Relations – How she convinces owners to trust a remote management model.
- Real Estate Investment & Market Strategy – Why she chose Vermont and California for her properties.
- Future Plans & Expansion – Her podcast Seed Money and plans to develop properties on her Vermont land.
Get in touch with Jayla:
- Facebook -
/ jayla.siciliano.akers - Instagram -
/ atlasvacations - Website - https://www.atlas-vacations.com/
➢ Subscribe: 
/ @smartstayshow
- 00:00 - Welcome & Guest Intro
- 01:14 - Jayla’s Start in STRs
- 03:33 - Why Now Is the Best Time to Buy
- 04:12 - Managing Luxury STRs
- 06:21 - Secrets to Remote Management
- 07:35 - Gaining Owners’ Trust
- 09:38 - Key Lessons in STR Growth
- 11:57 - Balancing Quality & Costs
- 15:01 - Overcoming Imposter Syndrome
- 19:18 - STR Challenges & Surprises
- 22:57 - Setting Boundaries & Scaling
- 26:48 - Jayla’s Future Plans
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