Short Term Rental Pros Podcast

Jordan McDonough is a Co-Founder of Somerled Designs (a short term rental design company). Her and Jeremy sit down and have a convo about how she has helped build a design power-house with 60 employees in two years. Learn how she built her company and how her clients are having success launching high-potential Airbnb's.

In this episode of the Short Term Rental Pros Podcast, Jeremy welcomes guest Zach, who shares his unique perspective on short-term rentals and his recent transition into a new role with Journey, a next-generation loyalty program. Zach discusses the acquisition of his previous company, Stay Watched, by Journey, and sheds light on the new platform's vision of combining vacation rentals and boutique hotels into a unified loyalty program. They delve into the importance of crafting unique, luxurious, and high-value experiences for guests, the shifting landscape of consumer expectations towards luxury, and the significant role of social media in direct marketing for short-term rentals. Key takeaways include building a strong hospitality brand, leveraging social proof, and focusing on fewer but highly differentiated units to create exceptional guest experiences.

In this comprehensive episode of the Short Term Rental Pros podcast, Jeremy recounts a period filled with remarkable events and significant challenges. From dealing with the aftermath of two hurricanes affecting properties in Florida and North Carolina, to attending the Chicago Marathon and VRMA conference, Jeremy shares personal stories and key lessons on resilience, the importance of flood insurance, and community support. The episode highlights insights from major conferences discussing networking, AI, and short-term rental software innovations. Additionally, it delves into the creation and growth of BNBCalc, a tool aimed at enhancing short-term rental portfolios, and the ambitions behind it. Jeremy also reflects on his encounters with major companies and a high-profile interview involving Tim Walz, navigating logistics with the Secret Service. Moving between personal anecdotes, industry advancements, and future aspirations, the episode underscores the power of mission-driven investments, consistency, and seizing unique opportunities in the rental industry.

In this episode of the Short Term Rental Pros Podcast, Jeremy sits down with Emir Dukic shares his extensive journey and insights in the short-term rental industry. Emir, who started as a civil engineer, transitioned into the tech startup world before venturing into real estate. He co-founded Rabbu, a platform aiming to be the 'Zillow' of short-term rentals by providing investment data, agent, and lender connections. Emir recounts his personal history from emigrating from Bosnia to settling in the U.S., his early entrepreneurial ventures, and developing Rabbu. Rabbu offers tools for property management and investment, focusing now on data and lead generation for real estate agents and lenders. Despite industry challenges amplified by recent market conditions, Emir emphasizes the sustained growth and demand in the short-term rental space and Rabbu's role in professionalizing the asset class. Throughout the conversation, Emir shares the strategic pivots Rabbu undertakes to adapt to industry changes and market demands.

In this episode of the Short Term Rental Pros Podcast, host Jeremy interviews Jay Ulrich, a successful operator of approximately 37 properties. Jay shares his journey from being a civil engineer to becoming a full-time short-term rental entrepreneur. He discusses the dynamics of scaling a property management company and co-founding HostBuddy AI, a software that aims to streamline communication for rental hosts through powerful AI tools. Jay reveals insights on property management models, current market trends in San Diego, and how HostBuddy enhances guest communication, increasing efficiency and guest satisfaction. The episode emphasizes the importance of strong relationships with property owners and the innovative use of technology in the short-term rental space.

In this episode of the Short Term Rental Pros Podcast, host Jeremy sits down with with Andrew, a key figure behind Wheelhouse, a software designed for pricing and revenue management in the short-term rental market. The discussion covers the impact of COVID-19 on the industry and how Wheelhouse adapted by restructuring their business model to focus on software development. Andrew delves into the nuances of managing urban versus rural short-term rentals, the challenges and strategies for scaling a rental portfolio, and the impact of new technologies like electric cars and social media on the hospitality industry. He highlights Wheelhouse's offerings, including their advanced revenue management tools and how these tools can help property managers increase efficiency and scale their businesses. The conversation also touches on predictions for the future of the industry, emphasizing the importance of local data and the evolving landscape of short-term rentals.

In this episode of the Short Term Rental Pros Podcast, Jeremy interviews Ryan, a young entrepreneur from Montreal, Canada, who has rapidly scaled his co-hosting business to manage properties in Florida and North Carolina. Ryan shares his background in sales, the pivotal shift from purchasing to co-hosting, and his unique approach to client acquisition and property management. He outlines his cold calling strategies, the importance of providing white-glove service, and the benefits of building in public. Despite initial challenges, Ryan's relentless pursuit and innovative marketing tactics have positioned him as a rising star in the short-term rental industry.

In this episode of the Short Term Rental Pros Podcast, host Jeremy welcomes back Kyle, a rapidly growing star in the rental property scene. Kyle has expanded his portfolio from one to six mega properties since last November, focusing on barn-style accommodations across the Midwest. The duo discusses his journey from working a W2 job to managing a flourishing rental business, the unique amenities of each property, the challenges and strategies behind scaling, and the importance of leveraging local community banks and social media for growth. They also outline future plans to optimize operations and further expand the business. Tune in for insights into investing, scaling, and managing short term rentals for large groups.

In this episode of the Short Term Rental Pros Podcast, Jeremy welcomes guest Jeff Iloulian, founder of HostGPO. They delve into Jeff's extensive experience in short-term rentals since 2014, exploring industry changes and trends, including the impact of regulatory shifts, the rise of co-hosting, and the strategic importance of choosing markets. Jeff discusses HostGPO's value in providing discounts for short-term rental supplies and their recent fundraising success. They also cover the significance of industry events, such as VRMA, and Jeff shares insights for succeeding with short-term rentals in 2024. This episode is packed with tips and trends for both new and experienced short-term rental operators.

In this episode of the Short Term Rental Pros Podcast, Jeremy welcomes Brian Meyer to discuss his unique business model that combines short term rentals with houseboats. Brian shares his journey from growing up on the Eastern Shore of Maryland to founding Flow Home, a company offering luxurious floating homes as short-term rental properties. They touch on Brian's background in paddleboarding and the skills that translated to his current venture. The discussion covers the operational logistics, regulatory challenges, and the scalability of Flow Home, as well as the significant benefits and novel experiences these floating homes provide guests. Brian emphasizes the importance of creating a superior guest experience and shares insights on how Flow Home has maintained high occupancy rates and rapid growth. Stay tuned to learn more about this innovative take on short-term rentals and the future of water-centric living.

In this episode of the Short Term Rental Pros podcast, host Jeremy and Patryk dive into high-level conversations about the short-term rental industry. They discuss the importance of being in the right rooms, share experiences from recent conferences, and explore the dynamics of their successful property management ventures. The episode also highlights Patryk's acquisition of a well-known co-host company, networking strategies, and the impact of their business on clients and staff. Listeners can gain actionable takeaways on scaling responsibly, building strong relationships with clients, and fostering community connections.

In this episode of the Short Term Rental Pros Podcast, host Jeremy is joined by Matt and Lori to discuss their progress over the past year in the short term rental market. The episode covers various expert discussions featuring speakers like Patrick Swiatek and John Bianchi. Matt and Lori share their experiences transitioning from property arbitrage to co-hosting, the benefits of investing in Florida versus Canada, and the importance of hands-on management. They also delve into their flipping background, real estate strategies, and the challenges of managing properties remotely. The episode concludes with their future plans to expand their boutique co-hosting business and diversify their property portfolio.

In this episode of the Short Term Rental Pros Podcast, host Jeremy is joined by John Bianchi to discuss a range of topics vital for success in the Airbnb market. Despite a challenging trip to the studio due to a nationwide computer virus, Bianchi shares his expertise on leveraging a data-driven approach to identify profitable properties and stresses the importance of having a reliable team to execute one's vision. The conversation delves into the rising demand for large group travel accommodations, highlighting the transition from traditional hotels to more unique, amenitized properties. They explore future trends in the market and provide actionable advice for Airbnb investors on ensuring long-term profitability and navigating potential downturns.

Jeremy sits down with Seb, a successful short-term rental investor. Seb shares his journey from dealing with flight debacles to investing in short-term rentals. He discusses his background as a professional athlete from Uruguay, his transition to finance, and how he and his wife started their real estate business in Maine. Seb details various investment strategies, including flips, long-term, and short-term rentals, emphasizing the challenges and successes of each. The conversation also covers the importance of financing, handling construction, and working with investors. Seb outlines a new project involving 17 acres of lakefront property, which he plans to develop into a profitable short-term rental while navigating the complexities of local regulations and financing.

In this episode Jeremy is joined by Mark and Xander, two highly successful real estate agents from the Poconos. They delve deep into their personal journeys into the short-term rental (STR) market, share insights on regulations and market idiosyncrasies in the Poconos, and discuss tips for succeeding in the ever-evolving STR landscape. From winter tourism trends to the impact of amenities like pet-friendly yards and game rooms, the conversation highlights essential strategies for potential investors and existing property owners. They also touch upon their own successful investments and the importance of attentively managing properties, as well as insights into other areas like long-term rentals and commercial opportunities. 00:00 Introduction to the Podcast 00:22 Meet the Poconos Power Brokers 00:44 Getting Started in Real Estate 01:23 Navigating Poconos Regulations 03:36 Impact of COVID-19 on Real Estate 03:52 Poconos as a Prime Destination 07:39 Client Demographics and Investment Strategies 11:33 Creating Standout Rental Properties 18:08 The Importance of Amenities 24:47 Challenges and Opportunities in Property Management 26:00 High School Hustle 26:21 Generational Differences 26:43 Family Business Dynamics 27:24 Short Term Rental Market Insights 28:48 Investment Strategies and Opportunities 30:35 Personal Experiences and Unique Selling Points 32:06 Challenges and Success Stories 34:02 Real Estate Market Trends 39:34 Pro Tips for Short Term Rentals 49:30 Conclusion and Contact Information

In this episode Jeremy interviews Natalie Palmer, a prominent figure in the short-term rental space and host of the No Vacancy Podcast. Natalie shares her journey of managing ten condos within a single complex, operating them like a boutique motel and the efficiencies gained through centralized operations. They discuss the benefits of scaling in one location, the operational challenges in rural markets, and the significance of building strong vendor relationships. The conversation also touches on Natalie's experience hosting large conferences, the thin margins involved, and the networking advantages these events provide. The episode concludes with a fascinating discussion about Natalie's new passion project: a podcast exploring various conspiracy theories. 00:00 Introduction to the Podcast 00:37 Meet Natalie Palmer 01:47 Centralized Operations in Short Term Rentals 05:05 Challenges and Benefits of Rural Markets 12:37 Hosting Conferences and Events 20:55 The Value of Networking 27:27 Exploring New Interests 29:27 Conspiracy Theories and Trump's Assassination Attempt 30:16 Security Lapses and Theories 33:30 Speculations on the Shooter's Motives 36:40 Potential Consequences of a Successful Attempt 38:16 The Role of Media and Public Perception 44:45 Conspiracy Theories and Public Trust 45:35 Introducing a New Podcast on Conspiracies 52:48 Real Estate and Tangible Investments 54:04 Conclusion and Contact Information

In this episode of the Short Term Rental Pros Podcast, host Jeremy Werden reconnects with Merritt, who shares his journey transitioning from long-term to short-term rentals due to tenant rights challenges in New York. Merritt narrates his initial skepticism, the hurdles, and eventual success through systematic and automated processes. He elaborates on his foray into property management, the complexities of property arbitrage deals, and offers insights on local market knowledge and revenue management. Personal aspects, such as balancing family life and entrepreneurial growth, are also touched upon. Merritt highlights his strategic expansion into Fort Lauderdale, emphasizing the value of partnerships. Additionally, Merritt discusses his evolution from basic tools to advanced property management strategies, focusing on revenue over occupancy, and his ambitious goal to triple his business by 2025. He advises newcomers against analysis paralysis, favors action, and shares his recent experiences, including a productive visit to Dumbo and an upcoming mastermind seminar. 00:02 Introduction to the Podcast 00:39 Merritt's Journey into Short-Term Rentals 03:19 Personal Life and Entrepreneurial Spirit 05:29 The Importance of Time Freedom 07:12 The Role of Virtual Assistants 16:19 Networking and Growth 25:03 Challenges with Arbitrage Deals 33:34 The Risks of Arbitrage in Real Estate 36:39 Challenges with Landlords and Property Management 41:21 Lessons Learned and Strategic Shifts 45:46 Focusing on Revenue Management and Market Knowledge 50:15 Expanding to New Markets and High-End Properties 01:02:13 Pro Tips for Newcomers and Future Goals 01:04:34 Conclusion and Final Thoughts

In this episode of the Short Term Rental Pros Podcast, host Jeremy Worden interviews Wil Slickers, a prominent figure in the hospitality and podcast industry. Having recently attended the SCIF Short Term Rental Summit, Wil brings valuable and current content including discussions about the evolving landscape of short term rentals and industry regulations. Wil also delves into his personal journey from a disillusioned hotel manager to quitting his job, starting his own podcast 'Slick Talk: The Hospitality Podcast', and eventually creating the Hospitality FM podcast network. Highlighting his property management experiences, Wil emphasizes the importance of providing hospitality and consistent quality. Throughout the episode, he offers practical advice on podcasting and stresses the value of audience feedback for improvement. Tune in to learn more about the short term rental industry, entrepreneurial insights, and the influence of hospitality in today's market. 00:02 Introduction to the Podcast 00:33 Guest Introduction: Wil's Background 01:32 Starting the Podcast Journey 04:14 Building a Podcast Network 08:09 Military Experience and Personal Growth 10:20 Property Management Business 14:39 Industry Insights and Current Trends 21:23 Marriott's Strategic Moves in Loyalty and AI 22:30 Corporate Travelers and Loyalty Programs 24:24 Regulations and Their Impact on Short-Term Rentals 27:40 New York's Short-Term Rental Ban and Its Consequences 32:23 Innovative Approaches in the Short-Term Rental Market 34:37 Airbnb's Future as a Social Media Platform 38:19 Podcasting Tips and Future Plans 41:52 Conclusion and Farewell

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 Worden, 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, Worden 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. Worden 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, Worden 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!

In this episode, Jeremy interviews Arthur Colker, Founder and CEO of Stayfi. We talked about how he started his Short Term Rental journey and the features and benefits of using StayFi to increase your direct bookings

In this episode, join Jeremy and Kyle Miklasz for an insightful and engaging conversation that goes beyond the numbers. He will share the fascinating story of how he was able to acquire a barn in Wisconsin for only $775,000 in an off-market deal without any realtors and how he transformed a barn into an amazing Airbnb destination that makes $300,000+ a year! Whether you're a seasoned investor or just starting, this episode is your ticket to learning from the experiences. Tune in for an episode packed with inspiration, practical insights, and the secrets to Kyle Miklasz's success in real estate and short-term rentals.

In this episode, Jeremy interviews his first mentee, Andy Gillespie, who is now an AirBnB Superhost, Investor, Realtor. Andy shares how he started in the short-term rental space and how he has been able to achieve such great success. If you are interested in learning more about the short-term rental business, then this is the episode for you! So be sure to tune in and listen to this episode! Follow Andy: ig: agsurrealestate

In this episode, Jeremy interviews Emmanuel Lavoie, a pioneer in the short-term rental industry and CEO of Jetstream Hospitality Solutions. Emmanuel shares his remarkable journey from selling his successful company to buying it back during the pandemic, co-hosting, managing vacation rentals and demonstrating his resilience and entrepreneurial spirit. He delves into his expertise in maximizing revenues and streamlining operations for multi-unit, short-term rental properties, highlighting the power of data-driven decision-making and customer-centric strategies. Whether you're a seasoned short-term rental investor or just starting out, this episode is packed with valuable insights and inspiration from one of the industry's most respected leaders. Don't miss out on this opportunity to learn from Emmanuel's incredible journey and gain actionable strategies for success in the dynamic world of short-term rentals.

In this episode of the Short Term Rental Pros podcast, we chat with Sean, Vanessa, and Tim of Easybreezy BnB, who have successfully scaled their short term rental business into a thriving company. We discuss how they got started, the challenges they've faced along the way, and their tips for success.

Introducing Ryan Bakke, a distinguished CPA, founder of LearnLikeaCPA, and a highly sought-after STR SUPERTEAM Coach. With a deep passion for real estate and finance, Ryan has established himself as a prominent figure in the industry, dedicated to saving real estate investors millions of dollars each year. In this episode, Jeremy and Ryan Bakke continues to discuss creative financing, how it works, its importance, and why it might be right for you.  If you want to know more about creative financing, this episode is for you! 

Mike Reilly was a Google employee in 2019 when he decided to quit his job and start his own business. He wanted to escape the 9-to-5 rat race and have more time for his family. He discovered short-term rentals and quickly realized that this was the perfect opportunity for him. He bought his first property in North Carolina and within 18 months, he had scaled his business to 19 properties. Mike Reilly is now the Co-founder and CEO of Your BNB Property, a company that helps short-term rental hosts automate their businesses and increase their profits. If you're dreaming of breaking free from the corporate world and starting your own business, Mike's story is the inspiration you need. Tune in to our podcast to learn more.

Jeff Iloulian has 8+ years of experience in the vacation rental industry, managing over 250 properties, from apartments to luxury mansions. He has worked directly with Airbnb on pilot programs and has a background in Economics, Philosophy, and a JD from UCLA School of Law. Before his entrepreneurial ventures, he practiced Business and Intellectual Property litigation as a lawyer for three years.

Jeremy welcomes John Back to the show to continue their conversation and to go through some of their ups and downs as investors and how that has led to their personal and business growth. John Bianchi is known as 'The Airbnb Data Guy,' John's passion is finding the most lucrative short-term rental properties possible. He creates reports for global short-term rental investors seeking the most lucrative Airbnb locations and properties. His "day-job" is the Head of Data at Techvestor, a short-term rental investment fund and he is the Founder of Point Analytics a consulting firm focused exclusively on helping clients make high-potential data-driven investments. In this episode, Jeremy and John have an interesting and insightful conversation on their learnings.

In this episode, Jeremy interviews Dylan, who started his short-term rental journey at the beginning of the year and has already grown a six-figure portfolio. Dylan shares his insights on how to find the right properties, set up your listings, and manage your guests. He also discusses his strategy for reinvesting his profits to grow his portfolio quickly.

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.