--- title: Want to Scale Your Airbnb Portfolio? Stop Doing Everything Yourself! - with Jayla Siciliano description: In this episode of SmartStay Show, Jayla Siciliano takes us through her journey to building a thriving short-term rental business across multiple states. image: https://str.legal/hubfs/luciakielportrait-jayla-edit-4%20(2)_edite.png.avif --- [Skip to main content](https://str.legal/smartstay-show/jayla-siciliano#main) [![FullLogo_Transparent_NoBuffer-2](https://str.legal/hs-fs/hubfs/FullLogo_Transparent_NoBuffer-2.png?width=300&height=82&name=FullLogo_Transparent_NoBuffer-2.png) ![FullLogo_Transparent_NoBuffer-2](https://str.legal/hs-fs/hubfs/FullLogo_Transparent_NoBuffer-2.png?width=300&height=82&name=FullLogo_Transparent_NoBuffer-2.png) ![FullLogo_Transparent_NoBuffer-2](https://str.legal/hs-fs/hubfs/FullLogo_Transparent_NoBuffer-2.png?width=300&height=82&name=FullLogo_Transparent_NoBuffer-2.png) ![FullLogo_Transparent_NoBuffer-2](https://str.legal/hs-fs/hubfs/FullLogo_Transparent_NoBuffer-2.png?width=300&height=82&name=FullLogo_Transparent_NoBuffer-2.png)](https://str.legal) - [Podcast](https://str.legal/smartstay-show) - [Contact Us](https://str.legal/contact) Open main navigation Close main navigation - [Podcast](https://str.legal/smartstay-show) - [Contact Us](https://str.legal/contact) - Search - [Get Started](https://str.legal/get-started) [Get Started](https://str.legal/get-started) Search [SmartStay Show](https://str.legal/smartstay-show) # Want to Scale Your Airbnb Portfolio? Stop Doing Everything Yourself! - with Jayla Siciliano ![Rory Gill](https://app.hubspot.com/settings/avatar/52a7403c0c5152799543ceb531cdb16d) Mar 18, 2025 12:25:17 PM 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 - [ ![](https://www.gstatic.com/youtube/img/watch/social_media/facebook_1x.png) / jayla.siciliano.akers  ](https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbWhJOV9Pc1RhN2dzM2gxaEN3THlTNWljZG9GQXxBQ3Jtc0trQXBsLWEwVFZQUExTMXR0aEdHX3NXb1VNY3Jkb0xNNmNraDRaLUlmakJocmg5T0ZxZ05INXdWc195TjNCdExlWV8tblFJLVE5ZTZFYVp3MTBJUFpvOXFsMEhPZVduMFlQWHVQSGgyOXlBX1ZyTDJOWQ&q=https%3A%2F%2Fwww.facebook.com%2Fjayla.siciliano.akers&v=QG7NtdTSZzs) - Instagram - [ ![](https://www.gstatic.com/youtube/img/watch/social_media/instagram_1x.png) / atlasvacations  ](https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbDVIZ1Uwbk5qWnh1eG43VlNhbFNGelJHZDZtUXxBQ3Jtc0tsNmwwQ1dYNGtWazBnQWx2bnlxdlFxc2h0Y1lncmdWcUlNcklKbkZMZS1WdlEzd3JUVG5FS01sZDY3MGlwYTU3YnpFTjNSU0pGLVBBN1Q0cXZ4QnhyT1VMclVicHNJbVlOamc1YzE5M0xNTExOa3NXTQ&q=https%3A%2F%2Fwww.instagram.com%2Fatlasvacations%2F&v=QG7NtdTSZzs) - Website - [https://www.atlas-vacations.com/](https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbEdfRVlBTUtaUGc4NXMxbVg4UTZhTnhqQUFyQXxBQ3Jtc0tsSExWWkpBTnhzMDdlQWxLNG9wSXlSenVWcVN0NHFMODBwMWdmSEFseGRDLW41dnM0WGgzR0lKNkFGNmZRSEowSi1Yc3BoQWNJRWM5MVRGbEdaSTVvbG9FcEJZQjFCbVI2bFlJRS16QTMwRFU4RHF0OA&q=https%3A%2F%2Fwww.atlas-vacations.com%2F&v=QG7NtdTSZzs) ➢ Subscribe: [  ![](https://www.gstatic.com/youtube/img/watch/yt_favicon_ringo2.png) / @smartstayshow  ](https://www.youtube.com/channel/UC9hSZeHoPAwF2bcEib0RCvg) - [00:00](https://www.youtube.com/watch?v=QG7NtdTSZzs) - Welcome & Guest Intro - [01:14](https://www.youtube.com/watch?v=QG7NtdTSZzs&t=74s) - Jayla’s Start in STRs - [03:33](https://www.youtube.com/watch?v=QG7NtdTSZzs&t=213s) - Why Now Is the Best Time to Buy - [04:12](https://www.youtube.com/watch?v=QG7NtdTSZzs&t=252s) - Managing Luxury STRs - [06:21](https://www.youtube.com/watch?v=QG7NtdTSZzs&t=381s) - Secrets to Remote Management - [07:35](https://www.youtube.com/watch?v=QG7NtdTSZzs&t=455s) - Gaining Owners’ Trust - [09:38](https://www.youtube.com/watch?v=QG7NtdTSZzs&t=578s) - Key Lessons in STR Growth - [11:57](https://www.youtube.com/watch?v=QG7NtdTSZzs&t=717s) - Balancing Quality & Costs - [15:01](https://www.youtube.com/watch?v=QG7NtdTSZzs&t=901s) - Overcoming Imposter Syndrome - [19:18](https://www.youtube.com/watch?v=QG7NtdTSZzs&t=1158s) - STR Challenges & Surprises - [22:57](https://www.youtube.com/watch?v=QG7NtdTSZzs&t=1377s) - Setting Boundaries & Scaling - [26:48](https://www.youtube.com/watch?v=QG7NtdTSZzs&t=1608s) - Jayla’s Future Plans **Tags:** ### Related Articles ### Comments ![SmartStay Coaching (transparent background).png-3](https://str.legal/hubfs/SmartStay%20Coaching%20(transparent%20background).png-3.avif) ### Short-Term Rental Counsel + Coaching Welcome to the SmartStay Show, where profit meets strategy for short-term rental hosts. Hosted by STR.Legal Attorney Rory Gill and 30-time Airbnb Superhost Jason Muth, this podcast is your go-to resource for mastering the world of vacation rentals on platforms like Airbnb and Vrbo. Each episode is packed with actionable tips and real-life strategies designed to help you maximize your income while safeguarding your property. Whether you're just starting out or looking to enhance your existing listings, the SmartStay Show covers everything from pricing optimization and guest communication to legal compliance and automation tools. With expert advice from seasoned hosts and industry insiders, we provide the playbook for turning your rental into a top-performing asset. What sets us apart is our focus on owners of small but mighty portfolios. You don’t need to own dozens of properties to succeed — we specifically cater to hosts who self-manage and want to get the most out of their vacation rentals.   ###### Categories ###### Recent Posts [![FullLogo_Transparent_NoBuffer](https://str.legal/hs-fs/hubfs/FullLogo_Transparent_NoBuffer.png?width=250&height=142&name=FullLogo_Transparent_NoBuffer.png)](https://str.legal) 40R Merrimac Street, Suite 201 East Newburyport, MA 01950   [978-351-9050](tel:9783519050)   ©2026 STR Legal PC. All rights reserved. Licensed in Massachusetts and New Hampshire.  [Privacy Policy](https://str.legal/privacy). - - - ```json { "@context" : "https://schema.org", "@type" : "BlogPosting", "author" : { "@type" : "Person", "name" : "Rory Gill", "url" : "https://str.legal/smartstay-show/author/rory-gill" }, "dateModified" : "2025-03-18T16:25:17.331Z", "datePublished" : "2025-03-18T16:25:17.000Z", "headline" : "Want to Scale Your Airbnb Portfolio? Stop Doing Everything Yourself! - with Jayla Siciliano", "image" : [ "https://str.legal/hubfs/luciakielportrait-jayla-edit-4%20(2)_edite.png.avif" ], "mainEntityOfPage" : { "@id" : "https://str.legal/smartstay-show/jayla-siciliano", "@type" : "WebPage" }, "publisher" : { "@type" : "Organization", "logo" : { "@type" : "ImageObject", "url" : "https://str.legal/hubfs/FullLogo_Transparent_NoBuffer.png" }, "name" : "STR Legal" } } ```