In this episode of the STR Data Lab, Jamie Lane interviews Hailie Anderson, founder of Airbnb Takeoff, about her journey in the short-term rental (STR) industry. Hailie, joining live from the Philippines, shares how she began her entrepreneurial journey at 19 during the COVID-19 pandemic. She graduated early from school and initially ran a content creation agency. Influenced by TikTok videos about rental arbitrage, she started her venture at 19, acquiring her first three units. 

Fast forward to now at 22, she has expanded to 58 units. Hailie explains the rental arbitrage model, noting it as a legitimate business strategy that allows property management sans ownership. She discusses her approach, which includes cold calling and emailing landlords to gain leasing agreements. Hailie also elaborates on the challenges and misconceptions of rental arbitrage, emphasizing the importance of legal and ethical operations. She highlights the critical role of building reliable local teams and leveraging technology, including PMS, dynamic pricing, and guest verification software. Hailie’s tech stack includes various tools like Price Labs, Hostaway, and True V to streamline operations. 

Moreover, she emphasizes the importance of understanding market differences and stresses on the entrepreneurial spirit of Gen Z, which she believes is characterized by boldness, a desire for fast ROI, and a passion for digital nomadism. Jamie and Hailie also debate the value of education from social media and the differences between Gen Z and older generations’ approaches to investment and risk. 

Hailie concludes by sharing her future plans, which include possibly expanding her portfolio further, staying in hospitality, and investing in properties for long-term stability. She encourages listeners to start pursuing their passions, emphasizing that success often comes from learning, failing, and trying repeatedly.

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Episode 145

In this episode of the STR Data Lab, Jamie Lane sits down with Joe and Max, founders and operators of Bach Brothers in Fredericksburg, Texas. The Bachmeiers discuss winning the AirDNA 2025 Top Property Manager Award. They share their journey into short-term rentals, starting from their first property purchase in Fredericksburg and growing to manage over a hundred listings with an impressive average rating of 4.957. 

Initially working full-time jobs in different fields, their operation diversified from being property owners to full-fledged property managers by responding to the growing market demands. They chose Fredericksburg because of its rising popularity and central location near major Texas cities, enhanced by numerous wineries and amenities. The brothers emphasize their customer-centric approach, ensuring high guest satisfaction through proactive communication and problem-solving, which has contributed to their success. 

They also discuss strategies for maintaining high ratings and scaling operations through quality checks and team empowerment. They highlight the importance of hiring the right people, acting on guest feedback, and keeping lines of communication open with property owners, ensuring transparency and trust. Discussing the challenges posed by increased competition and market fluctuations, they reveal their data-driven approach and adaptability in pricing and property enhancements. They advise new property managers to focus on reviews, hire a quality team, and concentrate on local, manageable growth. The discussion concludes with the Bachmeiers attributing their success to their dedicated team and expressing their commitment to maintaining high standards and potentially winning future accolades.

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Episode 144

In this episode of the STR Data Lab, Jamie Lane and Bram Gallagher discuss the midyear outlook for the economy and short-term rentals. They explore the updated forecast through 2026, addressing uncertainties surrounding recent economic events, inflation trends, and stock market fluctuations. Despite mixed signals, including recent inflation data and policy disagreements, the economy remains robust with low unemployment and solid job growth. The data shows a strong start for short-term rentals in 2024, with a 5.7% demand growth and 4.6% increase in listings, leading to slightly higher occupancy rates compared to last year. Supply growth, although slower since high interest rates and house prices have cooled the market, is experiencing a rebound. 

The episode highlights the variance in performance across different markets, such as urban vs. resort areas, and discusses the impacts of international and domestic demand shifts. They also delve into the impact of changing booking lead times on pacing data and future demand predictions. Gallagher forecasts continued demand and occupancy growth into 2026, while closely monitoring economic indicators, particularly inflation, for any potential disruptions. The discussion culminates in an analysis of economic prospects and the potential impact of policy changes, tariffs, and consumer confidence on the short-term rental market.

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Episode 143

In this episode of the STR Data Lab, Jamie Lane interviews Henry Corell, the founder of RevUp Rental, a revenue management consultancy company. Henry shares his journey from real estate interest in college to starting his own business focused on revenue management. He discusses his early experiences with short-term rental vacation businesses and the niche opportunities in revenue management within the industry. 

Henry explains the importance of being proactive rather than reactive in revenue management, emphasizing forecasting and reading data to make calculated decisions. He highlights key metrics for analyzing market health, such as consumer sentiment, economic trends, airline trends, and occupancy rates. Henry underlines the importance of understanding client demographics and adapting strategies accordingly. 

The conversation touches on the challenges of maintaining high booking rates, managing cancellation policies, and optimizing property listings by updating photos and allowing pets. Henry also discusses the role of communication in revenue management, balancing broader market trends with specific property analyses. He concludes by sharing insights on managing properties with fluctuating review scores and the impact of economic factors like job growth on the short-term rental market. Henry advises listeners to stay updated on economic indicators and maintain flexibility in their revenue management strategies.

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~~~~

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Episode 141

In this episode of the STR Data Lab, Jamie Lane hosts a discussion with Ryan Bakke about recent changes in tax law from the Big Beautiful Bill and their implications for short-term rental investors. Ryan, who has extensive experience helping investors save on taxes, explains his journey into the short-term rental and real estate tax niche. 

The conversation highlights recent tax law changes and their potential impact on investment strategies. Key changes discussed include bonus depreciation, its implementation, and how it can impact short-term rental investors. Ryan explains the concept of bonus depreciation, providing examples of potential tax savings and how these can be reinvested to grow initial investments. He also talks about the significance of qualifying for different depreciation schedules and cost segregation for leveraging tax benefits. Another major topic is the Qualified Business Income (QBI) deduction, its permanency, and who qualifies for it, especially in the context of short-term rental investments vs. long-term rentals. Ryan elaborates on the qualifying rules for offsetting W-2 income with short-term rental investments, including the 7-day use test and additional hour requirements. 

He also discusses potential economic benefits, such as saving on personal car interest and employer-paid student loans. The introduction of new financial accounts for children's savings and the broader economic effects of these tax changes are touched upon. Throughout, Ryan shares practical advice for investors on how to navigate these changes and maximize their tax savings. The session concludes with Ryan's recommendations for additional resources and ways to stay informed about tax strategies for real estate.

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~~~~

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Episode 142

In this episode of the STR Data Lab, Jamie Lane hosts a discussion with Ryan Bakke about recent changes in tax law from the Big Beautiful Bill and their implications for short-term rental investors. Ryan, who has extensive experience helping investors save on taxes, explains his journey into the short-term rental and real estate tax niche. 

The conversation highlights recent tax law changes and their potential impact on investment strategies. Key changes discussed include bonus depreciation, its implementation, and how it can impact short-term rental investors. Ryan explains the concept of bonus depreciation, providing examples of potential tax savings and how these can be reinvested to grow initial investments. He also talks about the significance of qualifying for different depreciation schedules and cost segregation for leveraging tax benefits. Another major topic is the Qualified Business Income (QBI) deduction, its permanency, and who qualifies for it, especially in the context of short-term rental investments vs. long-term rentals. Ryan elaborates on the qualifying rules for offsetting W-2 income with short-term rental investments, including the 7-day use test and additional hour requirements. 

He also discusses potential economic benefits, such as saving on personal car interest and employer-paid student loans. The introduction of new financial accounts for children's savings and the broader economic effects of these tax changes are touched upon. Throughout, Ryan shares practical advice for investors on how to navigate these changes and maximize their tax savings. The session concludes with Ryan's recommendations for additional resources and ways to stay informed about tax strategies for real estate.

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In this episode of the STR Data Lab, Jamie Lane interviews Patryk Swietek, owner of The Cohost Company. Patryk shares his journey into the short-term rental industry, starting as a tech employee at Aon Stay, where he observed operations scaling from 200 to over 1000 units. Post-COVID layoffs led him to start his own business, initially as a host and eventually acquiring three property management companies. His company now manages 100 listings in Joshua Tree, California. 

Patryk emphasizes the benefits of real estate for wealth creation but notes the thin margins and significant time commitment. He transitioned to managing properties for others to scale more effectively. Patryk details the advantages and challenges of acquiring property management contracts, highlighting the stability and long-term value these contracts provide. He also discusses the importance of integrating new acquisitions into a single Property Management System (PMS) and improving operational efficiency. 

The conversation touches on the competitive landscape of Joshua Tree, the importance of proactive hospitality, and leveraging tech solutions for better management. Patryk also discusses his public presence and its impact on his business. He concludes by stressing the importance of high-quality service, owner retention, and responsible scaling.

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Episode 140

In this episode of the STR Data Lab, Jamie Lane and co-host Scott Sage discuss short-term rental trends and market performance for the month of May. Jamie shares insights from his personal experiences managing his short-term rental property in the North Georgia Mountains. 

The discussion highlights a 6% year-over-year increase in STR listings, a 1% dip in occupancy, a 6% rise in ADR, and a 4.8% growth in RevPAR. They note that while nights booked are slightly down by 0.3%, shorter lead times for bookings are contributing to this trend. The conversation covers the implications of global events on travel and the STR market, including potential impacts on bookings from increased oil prices due to Middle Eastern conflicts. Jamie addresses how the economic landscape, job growth, and consumer confidence are influencing the industry. A key takeaway is that although demand and occupancy are fluctuating, shorter booking windows are becoming the norm. 

Scott and Jamie also analyze review scores based on operator size, revealing that smaller operators tend to have higher review scores but larger operators are improving the most year-over-year. They attribute this to both Airbnb's efforts to remove underperforming listings and operators becoming more attentive to review management. The episode concludes with advice for hosts and managers to adapt their pricing and booking strategies based on these trends, encouraging vigilance and real-time market analysis to remain competitive.

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Episode 139

In this episode of the STR Data Lab, Jamie Lane welcomes Michael O’Connell, founder of Happy Guest. Michael shares insights into the purpose and functionality of Happy Guest, a guest management system designed to streamline the check-in process for short-term rental properties while enhancing the overall guest experience. 

Happy Guest provides an all-in-one, web-based check-in solution that integrates with property management systems, allowing hosts to manage post-booking interactions seamlessly. The platform facilitates rental agreements, HOA forms, and upsells like early check-in and late checkout to generate ancillary revenue. Michael discusses the importance of user-friendly technology that doesn't require guests to download apps, making the check-in process smoother and more enjoyable. He explains how his team, consisting of experienced industry professionals, tested and refined the platform to ensure it provides maximum value and ease of use. Michael emphasizes the significance of personalization and flexible cancellations to improve guest loyalty and satisfaction. He also highlights the need for hosts to adopt new technologies that are more aligned with modern hosting demands, and offers insights into how automation can free up time for hosts to focus on delivering exceptional hospitality. 

The episode also touches on the development and features of Happy Guest, as well as the importance of great customer service in the short-term rental industry. Finally, Michael announces an upcoming virtual conference, Revenue Rehab, focused on revenue management strategies for hosts, which features notable industry CEOs and experts.

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Episode 138

In this episode of the STR Data Lab, Jamie Lane welcomes Alex Alioto, Head of Growth at Whimstay. They discuss the inception and growth of Whimstay, an OTA specializing in last-minute bookings for short-term rentals. Alex shares insights on how they fill unsold gap nights and create a win-win situation for both hosts and spontaneous travelers.

 The conversation delves into the challenges and strategies around booking windows, particularly the trend of shortening lead times due to economic uncertainties. Both emphasize the importance of having a diverse distribution strategy and dynamic pricing to capture various traveler segments. Alex highlights Whimstay's unique value proposition and discusses the impact of Gen Z and millennial travelers on the market. They also explore the rise in last-minute group travel and the significance of capturing next-gen travelers for long-term industry growth. Alex emphasizes the need for property managers to focus on direct bookings and maintaining high hospitality standards. Jamie and Alex agree on the importance of spreading demand across shoulder seasons to optimize occupancy and revenue. 

They conclude by discussing the marketing efforts Whimstay has undertaken to build its demand, including social media and targeted advertising. Alex urges hosts to think strategically about their listing platforms and dynamic pricing to maximize bookings. The episode wraps up with a call to action for property managers to list their properties on Whimstay and leverage its last-minute booking capabilities.

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~~~~

Learn more about Whimstay: https://www.whimstay.com/

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Episode 137