Short Term Rental Pros Podcast

This episode of the Short Term Rental Pros podcast features an in-depth conversation with Jeremy Werden and young entrepreneur Thomas Morey, detailing Thomas's journey in the short term rental business. Starting during his college years, Thomas grew his operation from zero to 14 properties, transitioning from a college student to a full-time entrepreneur. The discussion highlights the challenges and breakthroughs Thomas faced, including his shift from considering arbitrage deals to focusing on co-hosting, leveraging his youthful insight into technology for business optimization, and his personal growth amidst struggles with mental health. Moreover, Thomas shares actionable insights for those looking to enter the short-term rental market, emphasizing the importance of scalability, understanding market demand, and efficient operational strategies. 00:00 Introduction to Thomas Morey's Journey 00:38 Diving Into the Podcast with Thomas Morey 01:10 Thomas's Start in Short Term Rentals 01:49 The Challenges and Triumphs of Starting Out 02:42 The Strategy Shift: From Arbitrage to Co-Hosting 16:20 Scaling Up: Securing More Properties 21:16 Optimizing and Expanding the Business 28:41 Reflections and Future Directions 30:54 Unlocking the Secrets to Successful Property Listings 31:21 Custom Pricing Strategies for Individual Properties 31:38 The Art of Capturing Perfect Property Photos 32:21 Maximizing Revenue with Strategic Guest Targeting 33:20 Balancing College and a Thriving Rental Business 33:43 Setting Ambitious Goals Beyond Graduation 35:25 The Power of Mentorship and Community in Business Growth 37:15 Leveraging University Resources for Business Success 46:40 The Entrepreneurial Journey: Reflections and Advice 51:34 Embracing the Future with Confidence and Purpose

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 rental portfolio, the significance of dynamic pricing, listing optimization, and developing software to meet user needs. He also highlights the importance of setting clear goals, understanding the balance of risks and returns, and leveraging relationships within the industry. Through his narrative, Jeremy illustrates how to achieve financial freedom by mastering the art of short-term rentals and fostering a sustainable business model. 00:02 Welcome to the Short Term Rental Pros Podcast 00:28 The Journey Begins: From New Jersey to Entrepreneurship 02:02 Family Roots: Lessons from a Single Mother and a Hardworking Father 05:47 Sibling Bonds and Competitive Spirit 09:50 The Entrepreneurial Spark: Early Ventures and College Challenges 21:10 Navigating Career Paths: From Corporate Rejections to Startup Success 32:19 Pivoting to Short-Term Rentals: A Lake House Story 38:39 The Journey to Full-Time Real Estate Investing 39:33 Diving Deep into Renovation and Expansion 41:05 Exploring New Markets: The Florida Venture 48:05 The Shift to Software and Coaching 49:27 Empowering Others Through Coaching and Community 01:00:09 The Future: Goals, Software Development, and Personal Growth

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.

Recorded at the STR Wealth conference in Nashville, Jeremy is joined by Mike Chang and Syed Lateef to discuss the challenges and victories of running Airbnb businesses. They highlight the importance of in-person networking, acknowledging that everyone encounters issues in their operations and solutions often come from shared experiences. The group also shares how they've managed to significantly scale their businesses, not without attendant problems - ranging from everyday operations to lawsuits. Syed talks about the experience of running a 300-unit Airbnb arbitrage business, developing his personal branding, and building relationships in the industry. The group emphasizes building personal brand to create a supportive network and solving problems collectively.

In this episode, Jamie Lane, the Chief Economist at AirDNA, joins Jeremy for a detailed discussion about the nuances of property investment in the short term rental market. Jamie explains how the updated version of AirDNA offers a wealth of data on the global market, that helps users pick and analyze potential markets for investment, study past property performance, and even manage the pricing, bookings, and general operations of their properties. An exciting revelation discussed is AirDNA's foray into the property management systems space. Throughout the conversation, both Jeremy and Jamie stress on the fact that nuance and due diligence are key for success in the industry, since the short-term rental market is significantly different from the long-term one and predictive algorithms and metrics must be understood correctly to make informed decisions.

Sabrina Guler of Techvestor, a short-term rental fund, joins Jeremy for this episode. Sabrina shares everything from how she met her business partner via TikTok, to raising money and purchasing properties. She explains their impeccable process, from managing renovations and designs, dealing with property issues, optimizing bookings and revenues, maintaining five-star reviews, to finally selling properties with profits. She emphasizes the importance of details, creativity, and high standards in providing an excellent guest experience and outdoing the competition within the short-term rental industry. Sabrina also forecasted a positive future growth for the industry and urged investors to strategically study the market and invest in the little details that make a big impact.

In this episode, the Jeremy talks with Taylor Jones. Taylor shares his journey from posting about his personal experiences with short-term rentals to gaining tens of thousands of followers. He explains how he runs the acquisitions team at Techvestor, a short-term rental investment fund that acquires properties, renovates and furnishes them, and then splits the profits with investors. Taylor details the importance of amenities in setting your property apart, from game rooms and fire pits.

In this episode, Isaac French, a pioneer in the short-term rental industry, shares the story behind Live Oak Lake, his unique short-term rental resort. Isaac delves into his upbringing in a farmer's family, finding his passion for design and construction, breaking into the short-term rental industry with creative projects, and the importance of creating an unforgettable guest experience. He also talks about his experience selling Live Oak Lake for $7 million, which amounted to a 6.5x revenue multiple, highlighting the importance of creating multifaceted, commercial entities to maximize investment returns. Moreover, Isaac discusses the significance of social media in marketing rental properties, automation of operational processes to achieve efficiency, and his upcoming projects and initiatives.

In this episode, Jeremy is joined by Alex Shapiro, creator of CanMonkey - a service revolutionizing the short-term rental property business by automating trash removal. Alex shares the journey of starting and scaling CanMonkey from dealing with improperly handled trash complaints to growing his service across 18 states in the U.S, motivated by a commitment to uninterrupted service, customer satisfaction, and keen attention to detail. We delve into the potential evolution of CanMonkey as a one-stop-shop for rental property services, leveraging its consistent presence at properties, and its vast data collected from properties which could benefit other business ventures, such as insurance firms. Alex's journey is an inspirational message about seizing opportunities emerging from challenges. 01:32 Understanding the CanMonkey Service 04:44 The Importance of Trash Management in Short Term Rentals 06:44 The Benefits of Using CanMonkey Service 07:17 The Expansion and Future of CanMonkey 07:39 The Challenges and Solutions in Trash Management 09:26 The Importance of Compliance with Trash Regulations 10:08 The Role of CanMonkey in the Gig Economy 16:42 The Growth and Expansion of CanMonkey 29:02 The Challenges and Successes in Starting CanMonkey 32:36 The Future Prospects of CanMonkey 41:51 Exploring the Potential Market for Trash Collection Services 42:33 The Challenges and Opportunities of Bootstrapping a Business 42:44 The Shift Towards a Renter's Nation and Its Implications 43:40 Exploring New Business Opportunities in the Rental Market 45:06 The Journey of Bootstrapping and Scaling a Business 45:58 Understanding Customer Churn and Retention in the Rental Market 55:53 The Potential of Expanding Services Beyond Trash Collection 01:08:14 The Importance of Staying Focused and Adapting in Business 01:12:29 The Future of Can Monkey: Scaling and Diversifying Services 01:17:09 The Power of Persistence and Staying True to Your Business Vision

In this episode of the Short Term Rental Pros Podcast, host Jeremy Werden reflects on the past year, discussing his achievements and challenges in the short term rental business, as well as his personal milestones like his recent engagement. He highlights his revenue growth in 2023, his impactful experiences in providing mentorship, and future goals for his businesses in 2024. Jeremy also shares his outlook on market trends and industry predictions for the upcoming year. Lastly, he emphasizes the importance of setting and sharing clear, specific goals for personal and business growth

In this episode, Jeremy welcomes back STR Pro Patryck Swietek. Hear how he went from just 14 listings to managing a whopping 33 listings and with 9 more on the way (Total of 42 listings) in the Joshua Tree area. Learn the strategies that propelled him to $250k/month in Airbnb. This episode is packed with actionable tips for scaling your hosting business like a pro. Don't miss this must-listen episode! Unlock the secrets to explosive Airbnb growth with Jeremy and Patryck!