What if one tool could organize your entire short-term rental business—and actually give you your time back?
In this episode, we sit down with hospitality veteran turned systems expert Michael Dinwiddie to talk about the real-world challenges of managing short-term rentals and how the right systems can transform your operation from chaos to calm. Michael shares how he uses Notion as a “second brain” to streamline everything from SOPs to onboarding, and why even single-property hosts can benefit from getting organized early.
The conversation dives into practical strategies for empowering virtual assistants, leveraging AI, and building a business that runs smoothly—even when you’re not around. Whether you’re just starting out or scaling up, this episode is packed with insights and inspiration to help you get out of the weeds and take control of your business.
Things we discussed in this episode:
- The importance of systematizing short-term rental operations to reduce chaos and anxiety.
- Using Notion as a “second brain” to organize property information, SOPs, and tasks.
- The benefits of documenting processes for scalability and team empowerment.
- Leveraging Notion’s AI features to summarize SOPs and answer operational questions.
- Onboarding and training new team members, including local operations managers and virtual assistants.
- The transition from handling everything personally to delegating guest communications and tasks.
- Building recurring task systems for proactive property maintenance.
- The value of empowering and trusting your team to deliver excellent service.
- Personal stories about business growth, work-life balance, and learning from experience.
- Michael Dinwiddie’s journey in hospitality, business expansion, and creating training resources for others.
Get in touch with Michael:
Instagram - https://www.instagram.com/cometogethere/
Facebook - https://www.facebook.com/togetherevacationrentals
Website - https://togetherevacationrentals.com/
#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals AirbnbHost #PropertyManagement #Notion #BusinessSystems #VacationRental #Automation #TeamBuilding #HospitalityIndustry #ProductivityHacks
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