Most operators think better tech will fix their problems. It won’t.
In this episode, Frank Bosi (Hostfully) joins the show to unpack the real challenges STR leaders face as they scale—pressure, decision fatigue, emotional weight, and the constant tension between automation and hospitality.
Drawing from years inside luxury hotels like Ritz-Carlton and Four Seasons, Frank breaks down what most operators get wrong about tech stacks, leadership, hiring, and guest experience—and how to build systems that create confidence instead of doubt.
Inside this episode:
- Why tech stack decisions are emotional, not logical
- How disconnected tools quietly create leadership stress
- The difference between automating tasks vs removing hospitality
- What luxury hotels get right about training and consistency
- Why leaders must absorb pressure instead of passing it down
- How to hire people who protect your brand when you’re not watching
This is a must-listen for any STR operator building a team, scaling systems, or feeling the weight of leadership.
00:01 – Why Tech Stack Decisions Are Emotional, Not Logical
03:45 – Automation vs Hospitality: Where Operators Go Too Far
07:10 – The Weight of Leadership Most People Aren’t Ready For
11:00 – Why Disconnected Tools Create Doubt and Stress
15:20 – Lessons STR Operators Can Steal From Luxury Hotels
19:10 – Why Leaders Can’t Have “Bad Days” Publicly
23:30 – Hiring People Who Protect Your Brand When You’re Not There
27:40 – Training, Standards, and Why Consistency Beats Luxury
31:50 – Using Tech to Create Confidence, Not Complexity
36:40 – The Real Role of a Leader in Scaling STR Operations
Guest Bio:
Frank Bosi is the Senior Director of Partnerships at Hostfully, a leading platform supporting short-term rental operators around the world. He drives strategic relationships across the STR ecosystem; working with technology partners, influencers, coaches & thought leaders to help property managers scale and deliver great guest experiences.
Frank also actively contributes to industry conversations through webinars, events and podcasts (such as this) designed to help operators grow smarter, faster, and more profitably.
Outside of work, Frank prioritizes faith, fitness, and family; spending his free time with his wife and kids, training CrossFit, and staying focused on overall wellbeing.
Guest Link:
https://www.instagram.com/frank_bosi/
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