Ep 277 – Tech, Teams, and the Emotional Cost of Scaling STR Businesses with Frank Bosi
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 [...]
Ep 276 – Your Calendar Is Exposing Why You’re Not Hitting Your Goals
Your goals aren’t failing — your calendar is. In this episode, E and Chris break down why most people start the year motivated… then quietly drift back into old patterns. The problem isn’t strategy, tools, or ambition — it’s misalignment between who you say you want to become and how you actually spend your time. This conversation dives deep into identity, courage, time audits, consistency, and the hidden habits that [...]
Ep 275 – The New Standard for STRs: Design, Ops, and Discipline with Shane O’Connor
The STR game has changed—and most operators haven’t caught up. In this episode, we break down what actually separates top-performing short-term rentals from the ones stuck in the middle. From design and amenities to operations, leadership, and systems—this is a real look at how elite STR businesses are built and sustained in hyper-competitive markets. This isn’t theory. It’s what’s working right now. Inside this episode: Why “good enough” STRs are [...]
Ep 274 – Stop Setting Goals. Start Becoming This Person
Most people don’t fail because they lack discipline — they fail because they’re trying to grow without changing who they are. In this episode, Chris and E break down why goals alone don’t create change, how identity drives momentum, and the real reason most people stall out by February. This is a deep, practical conversation on discipline, accountability, emotionalized goals, and how to build habits that actually stick. If you’ve [...]
Ep 273 – The Inner Game of Building a High-Performance STR Business with Stacey St. John
Most entrepreneurs focus on tactics — but the real breakthroughs happen internally first. In this episode, Stacey St. John breaks down how self-awareness, intuition, mindset, and values-driven leadership shape long-term success in business and life. From recognizing limiting beliefs to building aligned teams and managing energy, this conversation goes far beyond surface-level motivation. If you’ve ever felt stuck, overwhelmed, or pulled in too many directions — this episode explains why [...]
Ep 272 – How AI Will Replace Most STR Ops Work (And What Operators Should Do) with Shahar Goldboim
AI isn’t a tool anymore — it’s infrastructure. In this episode, Chris and E sit down with Shahar Goldboim, founder of BOOM, to break down how AI is fundamentally changing short-term rental operations, exits, and scale. From selling a property management company to building tech that replaces broken workflows, this conversation dives deep into why fragmented tools are failing and why operators who don’t adapt will fall behind. Inside this [...]
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