In this episode, Matt welcomes his best friend, Josh Gua, to discuss a significant decision in Josh’s real estate investment journey. Josh owns a property in Seaside, Florida, and is debating whether to continue with a property manager or to manage it himself. Having bought the property in July and with a property manager in place for an easy transition, Josh has noticed several inefficiencies and underperformance issues with the property manager. They discuss the possibility of taking control to ensure dedicated attention and maximize the wealth from his condo. Matt and Josh share similar experiences in managing properties, including fears, challenges, and the transition process. Matt provides a step-by-step plan for Josh to take over management. They discuss setting up Airbnb and VRBO listings, utilizing property management systems like Hospitable, and using automated pricing tools like Price Labs. Further, they emphasize building a strong relationship with cleaners and handymen and the importance of automating guest communication and other processes. Josh talks about his motivations, including diversifying his investments and creating a family-friendly space for personal use. They highlight the challenges and the financial benefits of managing the property themselves, including higher revenue potential without paying property management fees. The episode wraps up with Josh feeling more confident about self-managing his property, supported by practical tips and systems shared by the host. Both express optimism about revisiting the outcome after the peak season to evaluate the success of the transition.

00:00 Welcome to the Podcast

00:05 Introducing Josh Gua and His Property Dilemma

00:33 Debating Property Management vs. Self-Management

03:02 Josh's Real Estate Journey

08:07 The Decision to Self-Manage

16:45 Setting Up for Success

24:22 Automated Guest Messaging

27:00 Setting Up Automated Pricing

32:37 Building Relationships with Cleaners

35:48 Managing Handyman and Maintenance

41:38 Stocking and Supplying Your Property

45:34 Final Thoughts and Gratitude