Ep – 281 Why Midterm Rentals Are the Smarter STR Strategy with Vivian Yip
Vivian Yip went from corporate burnout at Apple to building a thriving midterm rental portfolio and property management company. In this episode, she breaks down how she pivoted during the pandemic, why most investors don’t have enough grit, and how mastering calendar discipline can completely transform your rental income. We dive into: • Why community changes everything in real estate • The biggest mistake STR hosts make when pivoting to [...]
Ep – 280 – How Influencer Marketing Really Works for STRs (And Why Most Hosts Get It Wrong) with Madison Rifkin
Most STR hosts misunderstand influencer marketing — and it’s costing them bookings. In this episode, Madison Rifkin breaks down what actually works when partnering with content creators, why follower count is a useless metric, and how STR operators should think about social media as a long-term control channel — not a quick ROI play. We also go deeper into founder identity, building brands that can be sold, and the mistakes [...]
Ep 279 – Why Conviction Beats Experience in Building a Real STR Business with Hailie Anderson
Success in STR isn’t about age, capital, or the model you choose — it’s about conviction. In this episode, we sit down with Hayley Anderson, a 22-year-old operator already on her second business, to unpack the mindset, discipline, and leadership traits that actually drive growth. From failing early to building confidence through reps, this conversation goes far beyond arbitrage or co-hosting. If you want to scale your business — or [...]
Ep 278 – How Great Leaders Scale Teams Without Losing Control with Ryan Leake
Scaling isn’t a systems problem — it’s a leadership problem. In this episode, we break down what actually changes when you go from being a solo operator to leading a real team. From earning respect instead of demanding it, to building systems that support people (not suffocate them), this conversation unpacks the leadership shifts required to scale without chaos. If you’re growing doors, people, or partnerships — this episode will [...]
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 [...]
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