119 - Stop Running Your STR Business From Your Head | Michael Dinwiddie of RentalMind

Michael Dinwiddie is back and a lot has changed in the year since his first appearance on the show. A new baby, a burned software company, and a brand new product that might be the most practical operations tool built specifically for vacation rental managers. Matt and Austin welcome back the founder and CEO of RentalMind for a deep dive into the operating system he built to give STR operators their lives back. Michael manages 27 properties in Washington State through his company Togethere Vacation Rentals, and built RentalMind out of his own pain of trying to run a growing portfolio without a centralized system. The result is an AI-powered operations platform that combines your knowledge base, SOPs, tasks, projects, and property data into one place, and even imports your messy Google Drive and Notion exports and organizes them automatically in under a day. Here is what you will learn: Why getting your operations out of your head and into a system is the single highest leverage move you can make in your STR business, how RentalMind’s AI import feature can take your disorganized Google Drive and get 80% of your system built in less than one day, why Michael set a hard rule to never work after 5 PM or on weekends and how RentalMind made that possible, what Macaw is and how it functions as an AI that your team asks questions to instead of texting you at 11 PM, why pricing per property instead of per user is a game changer for growing property management teams, at what stage Michael recommends operators get started (hint: property three is the tipping point), and how to go from zero to a fully functional operations system in 60 to 90 days. Matt also gives a behind-the-scenes update on how Claude Code is now editing the podcast, creating reels, and writing descriptions automatically, which is kind of meta given the guest. Watch the 15-minute demo and start your free trial at rentalmind.ai/demo. Find Michael on LinkedIn and follow along on Instagram at @rentalmind.ai. 👥 Follow The Show The Co-Host Bros Podcast Instagram: @cohostbros Facebook: @cohostbros YouTube: @cohostbros TikTok: @cohost.bros ⸻ Follow the Hosts Matt Codd Instagram: @creativecodds TikTok: @creativecodds Facebook: @matt.codd.3 LinkedIn: https://www.linkedin.com/in/matthew-codd-9a3761375/ Austin Spitzenberger Instagram: @austin_spitzz TikTok: @austin_spitzz Facebook: @austin.spitzenberger LinkedIn: https://www.linkedin.com/in/austin-spitzenberger-70481111b/