This comprehensive podcast features Jeremy Werden, who shares an insightful and inspiring journey in the short-term rental industry, marked by his entrepreneurial spirit inherited from his family. Starting with a profitable investment in a lake house and expanding to boat rentals and more properties, Jeremy emphasizes the importance of hard work, strategic planning, and community support. Additionally, the podcast delves into the mindset necessary for success, the value of learning from experiences, and giving back to the community. Jeremy discusses the challenges and strategies of scaling a r ..read more

Tune in to hear Jeremy's insightful discussion with Taylor Jones, a successful entrepreneur who has acquired 160 short-term rental properties. Taylor shares his expertise on expanding services for everyday investors, emphasizing the importance of finding, acquiring, underwriting, and scaling short-term rentals efficiently. Jeremy asks Taylor questions about how to improve his existing properties, exploring potential upgrades for higher revenue and operational advice. Some of Taylor's advice includes practical tips on photo optimization for listings, leveraging amenities for competitive ad ..read more

Tune in to hear Jeremy's insightful discussion with Taylor Jones, a successful entrepreneur who has acquired 160 short-term rental properties. Taylor shares his expertise on expanding services for everyday investors, emphasizing the importance of finding, acquiring, underwriting, and scaling short-term rentals efficiently. Jeremy asks Taylor questions about how to improve his existing properties, exploring potential upgrades for higher revenue and operational advice. Some of Taylor's advice includes practical tips on photo optimization for listings, leveraging amenities for competitive ad ..read more

In this episode, Jeremy is talking with Sief Khafagi, the founder of Techvestor. Techvestor is a company specializing in short term rental properties. Techvestor impressively manages between 130-140 properties, generating close to $20 million in yearly revenue. Sief shares his journey from tech, including a stint at Facebook, to entering the short term rental market propelled by a personal need for family-friendly accommodations and spotting an investment opportunity in Airbnb properties before they became mainstream. He covers the importance of assembling the right team to tackle the dynamic ..read more

Ben Wolff, a trailblazer in the short-term rental industry, joins Jeremy for this episode. Ben is co-founder and developer of Onera, a luxury treehouse resort in Texas Hill Country. His experiential hospitality firm Oasi develops and manages a portfolio of landscape resorts, boutique hotels, and luxury retreats.  Ben discusses the challenges and lessons from his first project, Onera Fredericksburg, and how it led to the creation of other ventures like Onera Wimberly and the upcoming Oasi Hill Country resort. This conversation covers financing strategies, the importance of building a solid ..read more

Hanan Kim, a successful property entrepreneur, joins Jeremy this week to dive into the intricacies of scaling in the short-term rental market and transitioning into boutique hotels. She talks about the significance of understanding financials, studying successful properties, and the necessity of continuous education for thriving in this industry. Despite facing challenges, Hanan shares her strategic approaches to various U.S. markets and highlights the importance of operational management, including guest communication and staffing ..read more

In this epiosde, Jeremy is joined by Shahar Goldboim, a real estate expert who transitioned into short term rentals almost by accident and later innovated in the space by co-founding a tech company, Boom. Located in Miami, Shahar shares his journey from purchasing a high-value property for Airbnb to creating software solutions for property management challenges. His company, DesignBR, managed a portfolio worth $150 million before he shifted focus to Boom, a tech wing designed to optimize property management systems (PMS) with AI, offering features like task management, owner and guest portals ..read more

In this episode, Jeremy interviews Blake Johnson, a short-term rental investor who has scaled his business to over 16 listings in just a few years. Blake shares his insights on how to use partnerships and innovation to grow your short-term rental business. He also talks about his unique strategy for investing with little to no upfront investment. Whether you're a beginner or a seasoned investor, this episode is packed with valuable information that can help you take your short-term rental business to the next level ..read more

In this episode, Jeremy is joined by Mark Lumpkin from STR Cribs, a company that specializes in designing and renovating short-term rental properties. Mark discusses the concept of the 'amenities arms race,' highlighting the necessity for hosts to continuously innovate and invest in their properties to provide unique, high-quality guest experiences. He shares insights on the significance of thoughtful design, the impact of specific amenities like pickleball courts and full-length mirrors, and the importance of preemptive maintenance and renovations. The duo also explores the challenges and str ..read more

In this episode, Blake Dailey is chatting with Jeremy about how he went from the Air Force to becoming a successful real estate entrepreneur specializing in short term rentals and boutique hotels. Starting with a VA loan for his first property, Blake quickly learned the benefits of house hacking and leveraged this strategy to acquire multiple properties. His journey led him to the niche of buying houses with guest houses, utilizing short term rentals as a staple of his business model. Blake talks about how he expanded into the boutique hotel industry, buying and renovating hospitality properti ..read more