Short Term Rental Secrets Podcast

AirDNA’s 2026 outlook and what it means for short‑term rental operators. Why demand is softening while supply flattens and average listings risk losing occupancy. Which markets and larger, luxury property types are positioned to outperform. How to sell homeowners on ROI upgrades and use AI and systems to scale without burning out.

Ryan Leake, managing partner and founder who scaled to 60+ luxury short-term rentals, talks leadership shifts when moving from solo operator to team leader. He discusses earning respect by example, swapping ego for delegation, using systems to prevent burnout, aligning company and personal goals, and preserving culture while scaling.

In this insightful discussion, Frank Bosi, Senior Director at Hostfully, brings a wealth of experience from his time in luxury hotels to the short-term rental world. He reveals why tech stack decisions are often driven by emotions rather than logic, emphasizing the balance between automation and maintaining hospitality. Frank highlights the leadership pressures that come with scaling and shares crucial lessons drawn from Ritz-Carlton's standards. His advice on hiring for attitude and creating consistent guest experiences is a must-hear for STR operators.

Explore how your calendar reveals your true priorities and sabotages your goals. Uncover the 'Perfect Week' exercise to pinpoint misalignments between your aspirations and daily actions. Learn why courage sometimes means saying 'no' and the importance of letting go of old identities. Small, consistent habits can lead to significant change, even when you feel busy but stuck. Discover how reframing challenges as enjoyable can enhance productivity and keep you aligned with your vision for the year.

Shane O'Connor, CEO of Alchemy Real Estate and a former Navy officer, discusses the evolving landscape of short-term rentals. He highlights the importance of meeting rising guest expectations with top-tier design and full amenities. Shane reveals how operations and exceptional hospitality ultimately outshine aesthetics. He shares strategies for scaling operations effectively, tapping into military leadership principles, and the need for disciplined systems to ensure longevity. Efficiency, not just design, is the key to thriving in competitive markets.

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 ever felt stuck despite “doing all the right things,” this episode will reframe how you think about growth — personally and professionally.Inside this episode:• Why identity matters more than motivation• How emotionalized goals create automatic discipline• The “never two days in a row” rule that builds momentum• Why most people sabotage themselves without realizing it• How to design accountability that actually works• Turning small daily actions into long-term transformation👉 If this episode resonated, share it with someone who’s setting big goals this year — and subscribe for more real conversations on growth, leadership, and execution.00:00 – Why the Point of a Goal Is Growth, Not the Outcome02:05 – Identity vs Outcomes: The Real Way to Set Goals04:20 – Emotionalizing Goals to Create Immediate Action06:10 – Going Deeper on “Why” Using the Seven Layers Exercise08:35 – Shifting from “I Have To” to “I Get To”10:15 – Building Momentum with Small, Non-Sexy Wins12:40 – Vision First: Thinking Big Enough for the Next Level15:05 – Quarterly Sprints and the Power of the 12-Week Year17:40 – Time Blocking Life, Family, and Business (In That Order)20:30 – Accountability, Never Missing Twice, and Staying in MotionGet FREE Access to our Community and Weekly Trainings:https://group.strsecrets.com/

Stacey St. John is a visionary real estate entrepreneur focused on empowering women in short-term rentals. In this lively discussion, she explores the importance of self-awareness and intuition in decision-making. Stacey highlights how identity shapes actions and shares practical mindset tools to combat overwhelm. She emphasizes hiring based on values rather than resumes and the significance of building aligned teams. Additionally, she candidly discusses her own struggles with limiting beliefs, revealing that continual improvement is her secret to success.

Shahar Goldboim, Co-founder and CEO of Boom, shares insights from his journey in real estate and technology. He explains how AI is revolutionizing short-term rental operations and suggests that fragmented software is hindering growth. Shahar discusses the importance of focusing on operational data, which lets AI handle 80% of guest communications. He emphasizes that businesses must evolve or risk falling behind. Additionally, he highlights that building relationships is key to success in the industry.

Mark Lumpkin, founder of STR Cribs, reveals how to transform underperforming short-term rentals into profitable ventures. He discusses common pitfalls made by high-net-worth investors and emphasizes the importance of strategic amenities over sheer quantity. Mark advocates for a focused hiring approach, likening elite teams to 'SEAL Team 6,' and shares insights on maintaining a high-performance culture through healthy tension. Learn how to identify ideal clients and refine operations for success in the STR landscape.

In this episode, Bernie Cesareo, a dynamic short-term rental investor and operator, shares his transformative journey from struggling to thriving. He emphasizes the importance of shifting identity to unlock true potential, discussing how self-image and mindset influence business success. Bernie reveals his methods for delegating tasks, trusting his team, and manifesting dreams like his new Jeep Rubicon. He encourages listeners to think big, act as CEOs, and embrace gratitude to attract opportunities. Bernie's insights aim to empower fellow hosts to break out of stagnation.