--- title: Betting on Yourself + Leaving a Lucrative Career for STRs (WAS IT WORTH IT?) - with Payton Cummings description: Payton Cummings shares her journey from corporate consulting to full-time entrepreneurship and the mindset shifts that made it possible. image: https://str.legal/hubfs/paytonbrandphotos-138.jpg --- [Skip to main content](https://str.legal/smartstay-show/payton-cummings#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) # Betting on Yourself + Leaving a Lucrative Career for STRs (WAS IT WORTH IT?) - with Payton Cummings ![Rory Gill](https://app.hubspot.com/settings/avatar/52a7403c0c5152799543ceb531cdb16d) Mar 25, 2025 7:00:00 AM Would You Quit Your 9-to-5 to Build a Short-Term Rental Empire? Payton Cummings did exactly that—leaving behind a steady paycheck to scale a thriving 17-property short-term rental business! In this episode, she shares her journey from corporate consulting to full-time entrepreneurship, the mindset shifts that made it possible, and how community and strategy helped her think bigger. If you're dreaming of turning your side hustle into a sustainable business, this episode is packed with real insights and actionable advice you won’t want to miss! Things we discussed in this episode: - Peyton's transition from a W2 management consulting job to full-time short-term rental entrepreneurship - The importance of joining entrepreneurial communities like STR Secrets for networking and mindset growth - Financial planning and considerations before leaving a steady job, including healthcare and income sustainability - Building and scaling a short-term rental business from 3 personal properties to 17 co-hosted properties - The challenges of delegating guest communication and learning to trust a virtual assistant team - Strategies for local networking, including joining BNI groups and connecting with local developers and investors - The value of investing time in personal mindset development and strategic business planning - Real estate professional tax status and potential tax benefits for full-time real estate entrepreneurs - Maintaining personal relationships and friendships while growing a business, especially as an entrepreneur - The process of automating guest communications while still maintaining quality customer service and oversight Get in touch with Payton: - Facebook - [ ![](https://www.gstatic.com/youtube/img/watch/social_media/facebook_1x.png) / payton.young.7  ](https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbjhHeng1cS1OUXlFbXo2RG9nR1QtUWlaZGpud3xBQ3Jtc0ttOW56UUk0N2JKWmJiT05iSTJGSmk0RG5KLVFCekZNS210Tk5ZOW5ON2Vtdk9oMlh6QnR2MnhsbTUtSTJpd2huYjRsRWVOSHNkQnZJOFI5bGNNVi00YzF4dDBub2NJamNQeFY5RFlkU2JFVXo5WmQxRQ&q=https%3A%2F%2Fwww.facebook.com%2Fpayton.young.7&v=IkkAy3xe7r8) - Instagram - [ ![](https://www.gstatic.com/youtube/img/watch/social_media/instagram_1x.png) / staymodernproperties  ](https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbXdaUmM4UDFzLVBpUEVIT3hybk1STWhvWDVPUXxBQ3Jtc0tuYzlYV29mNWlsUVVHQmZ0czVqcHFpTzFxR1dOU2lYdk9aQUw4QUI2WTVqU3MxRFdFN3dQX0pPVUVkd2hOaTZiN2VtSWMxU2UtRm1SOUM1amNkT01HRmthbHA5dnI1WFVnU1VzV2c1TE9ZaXF3NUtaZw&q=https%3A%2F%2Fwww.instagram.com%2Fstaymodernproperties%2F&v=IkkAy3xe7r8) - Website - [https://staymodernproperties.com/](https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqa3lfeWpzdkJpVE54azdwVmpoczdqd01jUXFfd3xBQ3Jtc0tsX1htQ0l5bW1jdUtBY2IyazU1eVYtdTRVMlNSRXZPdGtlYVo0Z3lEazVBaHVEeUQ4bHpSVGVWbUExOHA1dWxJZmdRZVlJdkNyU2JxME0zbmd6SXY3RDRFaTFIVnIyNF9sejItcDEyc1JUTHFfMVl6cw&q=https%3A%2F%2Fstaymodernproperties.com%2F&v=IkkAy3xe7r8) ➢ Subscribe: [  ![](https://www.gstatic.com/youtube/img/watch/yt_favicon_ringo2.png) / @smartstayshow  ](https://www.youtube.com/channel/UC9hSZeHoPAwF2bcEib0RCvg) **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" : "2025-03-27T01:06:21.793Z", "datePublished" : "2025-03-25T11:00:00.000Z", "headline" : "Betting on Yourself + Leaving a Lucrative Career for STRs (WAS IT WORTH IT?) - with Payton Cummings", "image" : [ "https://str.legal/hubfs/paytonbrandphotos-138.jpg" ], "mainEntityOfPage" : { "@id" : "https://str.legal/smartstay-show/payton-cummings", "@type" : "WebPage" }, "publisher" : { "@type" : "Organization", "logo" : { "@type" : "ImageObject", "url" : "https://str.legal/hubfs/FullLogo_Transparent_NoBuffer.png" }, "name" : "STR Legal" } } ```