Short Term Rental Secrets Podcast

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.

The arbitrage era is cracking — fast. With Sonder filing bankruptcy and operators across the country getting crushed by fixed leases, the truth is clear: the STR model you choose determines whether you scale… or sink.In this episode, we break down why arbitrage is failing, what Sonder’s collapse teaches every host, and why co-hosting remains the most profitable, low-risk, scalable model in 2025 and beyond.Inside this episode: • Why arbitrage collapses under pressure • The hidden costs operators never calculate • Why co-hosting produces higher margins with lower risk • How boutique operators beat centralized “big brand” models • What the fastest-growing hosts are doing differently • The shift every STR operator must make in 2025Message me to get a free resource and see how the program could fit your goals.Click the link below:https://go.strsecrets.com/podcast?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T034&utm_content=RESOURCE00:01:00 – The Real Cost of Arbitrage: Leases, Debt & Cash Burn00:02:30 – Why Arbitrage Margins Collapse in Today’s Market00:03:45 – Co-Hosting vs. Arbitrage: The Risk Difference00:05:10 – Arbitrage at Scale Becomes a Cash-Flow Death Trap00:06:15 – Real Examples of Small Operators Losing Money00:07:10 – The Tiny Margin of Error That Kills Arbitrage Deals00:08:30 – Why Co-Hosting Wins: Low CAC, High Lifetime Value00:10:20 – How Operators Are Scaling Co-Hosting With $0 Spend00:12:20 – Centralized vs. Local: Why Guest Experience Matters00:15:00 – Why Arbitrage Can’t Keep Up With Industry Changes00:17:00 – The Bankruptcy Wave: Small Operators Getting Hit00:18:30 – How to Pivot Out of Arbitrage Before It’s Too Late00:20:10 – What a Healthy Co-Hosting/PM Business Looks Like00:22:00 – No Get-Rich-Quick: The Reality of STR SuccessGet FREE Access to our Community and Weekly Trainings:https://group.strsecrets.com/

Brooke Pfautz, founder of Vintory and creator of Comparant, shares insights from scaling a vacation rental business to 500 properties. He reveals why many property managers struggle to break past 100 doors and the secrets of top operators. Learn how to design high-performance properties and why marketing is now essential. Brooke also discusses the importance of building a solid sales pipeline, attracting marquee properties, and empowering your team to make decisions. Tune in for practical advice on owner acquisition and operational excellence!

Discover the hidden value in your short-term rental business and how to build it for success. Learn from the mishaps of companies like Sonder and Vacasa, and avoid their pitfalls. Uncover what private equity firms look for when investing in STRs, as well as tips for scaling your business effectively. Find out why local operators can stand out with the right systems in place. Lastly, explore key strategies to position your business for a lucrative exit.

Chris Patsy, an accomplished short-term rental operator and a key figure in property management, shares his journey from financial struggles to owning 120+ properties. He discusses the shifting landscape of the STR industry and the importance of mentorship and community support. The conversation dives into the power of property management as an exit strategy, the benefits of consolidation in the industry, and the new era of education with upcoming shows to help operators scale while enhancing guest experiences.