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 advantage, and using data analytics for better performance measurement and strategic planning.

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 challenges of the business, especially in uncharted territories of the short term rental market. Sief also dives into Techvestor's approach to using a traditional syndication model for raising funds and acquiring properties, leaning heavily on innovating operational strategies and maintaining strong leadership to ensure investor confidence and company success.

Connect with Sief on LinkedIn: https://www.linkedin.com/in/siefkhafagi/

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 team, and how creating value for investors is key to advancing in the industry. 

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.

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, website builder, and business intelligence. The episode covers a range of topics from the importance of loving what you do, finding your niche, leveraging technology for efficiency, to practical advice on managing short term rentals and scaling your business. Shahar emphasizes the value of creating win-win situations and using data to improve operations and guest experiences.

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 strategies around permitting, budgeting for renovations, and identifying properties with unique features that can stand out in the market.

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 properties in different markets, including Florida and Tahoe, and eventually venturing into a substantial boutique hotel project in Tennessee. Blake shares insights on the complexities of financing and renovating these properties, the impact of regulations on STRs, and future plans for his business, including hosting the Boutique Hotel Con event.

Ruben Kanya, an expert in medium-term rentals, joins Jeremy for this episode. Ruben shares his journey from a student athlete to becoming a key player in the medium-term rental market. Without a traditional entrepreneurial background, Ruben leveraged his curiosity, work ethic, and the power of podcasting to educate himself on various business models, eventually leading to success in real estate. Ruben emphasizes the value of building relationships and listening actively to clients’ needs, which has been crucial in his ventures. He provides actionable advice on how to succeed in medium-term rentals by optimizing listings, being pet-friendly, and choosing the right properties to meet market demands.

In this episode, the founder of Turno, Assaf Karmon, joins Jeremy to discuss his business model which helps hosts of short-term rentals streamline their cleaning process. Turno acts as a connection hub between hosts and cleaning service operators, automating many processes including scheduling, payments, and issue reporting. The platform integrates directly with various property management systems, making it easier for hosts to keep track of cleaning-related issues and for cleaners to report their work. Assaf also shares how the platform has facilitated many cleaners to earn significantly via the platform.

Live from STR Wealth in Nashville, Austin Palacios joins Jeremy to talk about how he scaled his short-term rental business by using strategies like cold outreach and organic funnels. He explains how he developed a system that allowed clients to find him organically as well as through targeted outreach to larger property managers. Austin’s methods included targeting properties managed by large firms like Vacasa and Evolve, teaching real estate agents how to use Airbnb effectively, and offering setup assistance and referral fees. Austin also discussed the importance of sales skills, confidence, and expertise in attracting and retaining clients. He gives his advice on becoming an expert in the field, practicing confidence, and expressing one's skills to be essential in attracting and retaining clients.