Betting on Yourself + Leaving a Lucrative Career for STRs (WAS IT WORTH IT?) | Payton Cummings

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.facebook.com/payton.young.7 Instagram - https://www.instagram.com/staymodernproperties/ Website - https://staymodernproperties.com/ #SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #AirbnbHost #EntrepreneurLife #STRBusiness #SideHustleSuccess #PropertyManagement #BusinessGrowth #WomenInBusiness #DigitalNomadLife Follow Us! Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first episode of SmartStay Show! Following and subscribing to SmartStay Show not only ensures that you'll get instant updates whenever we release a new episode, but it also helps us reach more people who could benefit from the valuable content that we provide. SmartStay Show Website and on Instagram and YouTube Prideaway Stays Website and on Facebook and LinkedIn Straightforward Short-Term Rentals Website and on Instagram Attorney Rory Gill on LinkedIn Jason Muth on LinkedIn Hospitality.FM SmartStay Show is part of Hospitality.FM, a podcast network dedicated to bringing the best hospitality-focused podcasts to those in and around the industry, from Food + Beverage, Guest Experience, Diversity & Inclusion, Tech, Operations, Hotels, Vacation Rentals, Real Estate Law, and so much more!