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 momentum
This 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-Belief
04:00 – Rewiring Identity: From Overwhelm to Intention
08:00 – Leveraging Chaos: Why Adversity Becomes Your Superpower
12:00 – The Four Levels of Competence: From Unconscious to Mastery
16:00 – Winning in Business: Simplifying Systems, Offers, and Time
20:00 – $20K Days in 5 Hours: Prioritizing High-Leverage Work
24:00 – Clarity Is Power: Why Lack of Decision-Making Kills Momentum
28:00 – Excuse Audit: The Hidden Stories That Keep You Small
32:00 – Emotional Regulation: How to Respond Instead of React
36:00 – Final Challenge: Step Into Power and Choose a New Story
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