In this episode, we sit down with Ben Koons from Keystone Bookkeepers to unpack the unique challenges of managing finances in the short-term rental world. From early days of DIY spreadsheets to implementing professional systems, they explore what it takes to build scalable, stress-free bookkeeping practices for growing portfolios.

Jason and Ben also break down Airbnb’s new fee structure, share practical tips for owner reporting, and highlight fresh service offerings designed to support property managers. Whether you’re just starting out or overseeing dozens of listings, you’ll come away with actionable insights to streamline your financial processes, boost profitability, and protect your business as you grow.

Things we discussed in this episode:

• The critical role of financial systems in short-term rental businesses.
• The evolution and specialization of Keystone Bookkeepers in the STR industry.
• Challenges and solutions for bookkeeping as you grow from a small operator to managing multiple units.
• The importance of developing organized, repeatable systems and processes for scalability.
• Practical habits for keeping accurate, timely records and avoiding costly bookkeeping messes.
• The onboarding process for clients with messy or inconsistent financial records.
• The impact of Airbnb’s new fee structure and strategies to adjust commission and owner communications.
• Owner statements, trust accounting, and the nuances of co-hosting versus property management models.
• The introduction of new services from Keystone Bookkeepers, including vacation and income tax filing.
• Guidance on updating contracts and maintaining transparent communication with owners regarding industry changes.

Get in touch with Ben:

Youtube - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.youtube.com/@KeystoneBookkeepers

Facebook - ⁠⁠⁠https://www.facebook.com/KeystoneBookkeepers

Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://keystonebookkeepers.com/

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #Bookkeeping #PropertyManagement #AirbnbHosts #RentalBusiness #STRIndustry #OwnerReports #TaxStrategy #BusinessGrowth

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