March 25, 2025

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

34 minutes

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

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By Airbnb Superhost Jason Muth + Rory Gill

4.9

3939 ratings