EP 242 - How AI & Leadership Are Scaling the Best STR Businesses in 2025

This episode unpacks the real playbook behind scaling short-term rental businesses with AI, leadership, and culture.Straight from the STR Boardroom event in Salem, hosts Chris and E break down their biggest takeaways from Dr. Rachel Gainsbrugh’s AI workshop to the emotional breakthroughs in hot seats, to Mark from Minoan’s CEO mindset at 50+ employees.What you’ll learn: • The AI stacking method Rachel used to double her sales team’s close rate • The 5 levels of VA hiring, from cheap help to AI-powered specialists • Why great team members outgrow companies, and how to lead through it • The exact moment a founder must pivot from operator to people leader • How to use the 5 Dysfunctions of a Team framework to build culture that scales • Why emotional safety is the hidden growth lever most CEOs ignore • And how to actually implement event takeaways before you lose momentumThis isn’t another tech tips episode.It’s a tactical and vulnerable deep dive into what it takes to scale, lead, and stay grounded in 2025.00:00 – Building Confidence: Lessons from Struggle, Sales, and Self-Belief04:00 – Rewiring Identity: From Overwhelm to Intention08:00 – Leveraging Chaos: Why Adversity Becomes Your Superpower12:00 – The Four Levels of Competence: From Unconscious to Mastery16:00 – Winning in Business: Simplifying Systems, Offers, and Time20:00 – $20K Days in 5 Hours: Prioritizing High-Leverage Work24:00 – Clarity Is Power: Why Lack of Decision-Making Kills Momentum28:00 – Excuse Audit: The Hidden Stories That Keep You Small32:00 – Emotional Regulation: How to Respond Instead of React36:00 – Final Challenge: Step Into Power and Choose a New StoryGet FREE Access to our Community and Weekly Trainings:https://group.strsecrets.com