Short Term Rental Secrets Podcast Ep 266 - The Harsh Truth: If You Don’t Have Systems, You Don’t Have Freedom with Michael Dinwiddie
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Nov 3, 2025 Michael Dinwiddie, a real estate investor and hospitality operator, shares insights on creating effective systems for short-term rentals. He emphasizes that hustle can hinder growth and outlines how to automate operations to gain freedom. Dinwiddie discusses using Notion as a centralized system to manage multiple properties and the importance of delegating tasks without loss of control. He also highlights why trust in your team is crucial and the need to reframe guest complaints as opportunities for improvement in business. This conversation is a must-listen for anyone looking to scale their operations!
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Build A Second Brain For Operations
- Your brain can't hold growing operational detail; you need a 'second brain' for business knowledge.
- Michael built a Notion knowledge base to store unit info, FAQs, and recurring projects so the team can access it.
Leaving Expedia To Run A 15‑Unit Hotel
- Michael left Expedia after negotiating a monthly-fee management deal to run a 15-unit boutique hotel.
- He spent weeks living onsite to lead a renovation and learn hotel operations full-time.
Trust + Systems Enable Delegation
- Trust and systems are what let you delegate as you scale from operator to CEO.
- Michael learned at Expedia that trusting teammates and building processes enables stepping back from daily tasks.
