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  • 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[...]
  • 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[...]
  • 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[...]
  • 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[...]
  • 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[...]
  • 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[...]
  • 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[...]
  • 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[...]
  • 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[...]
  • 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[...]
  • 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[...]
  • 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[...]
  • 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[...]
  • 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,[...]
  • 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[...]
  • 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[...]
  • 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[...]
  • 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[...]
  • 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[...]
  • 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[...]
  • 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[...]
  • 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[...]
  • 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[...]
  • 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[...]
  • In this episode of the Short Term Rental Pros podcast, Jeremy chats with Easy Breezy Bnb, about their journey into private equity and short-term rentals. They share their insights on how to scale a co-hosting business, the challenges they've faced along the way, and their advice for new investors.
  • 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 discuss[...]
  • 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[...]
  • 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[...]
  • 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[...]
  • 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[...]
  • In this episode, Jeremy interviews Blake Holden, 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[...]
  • In this episode, Jeremy interviews Marc Hostovsky, founder of Minoan, who formerly worked at Jet.com (acquired by WMT in 2016 for $3.3B) where he managed a $400M omnichannel P&L and gained experience in both traditional retail (WMT) and eCommerce (Jet.com). With over a decade of retail experience, Marc recognized an opportunity to transform the relationship[...]
  • In this episode Jeremy interviews Devin Solow, a co-founder and partner of Better Properties, Better Construction, and Better Realty. In this captivating episode, Devin provides a fascinating glimpse into the world of real estate and property development, sharing valuable insights and stories from his journey in the industry. Whether you're a seasoned real estate professional[...]
  • In this episode, join Jeremy as he interviews Syed Lateef, the Instagram-famous 8-figure Airbnb Superhost. Discover how Syed achieved a remarkable $10 million+ in Airbnb revenue in 2022, earning a staggering $30K/day through his innovative hosting strategies. Tune in to uncover his journey from humble beginnings to becoming an industry trailblazer, redefining the art of[...]
  • In this episode, Join Jeremy in this insightful podcast episode as he sits down with the multi-talented John Hodge, also known as the "Bank Whisperer." John wears many hats with finesse – from being a dynamic public speaker to a seasoned real estate mentor, lending consultant, and licensed general contractor. With an impressive portfolio spanning[...]
  • In this episode, Jeremy interviews a dynamic Canadian couple who've successfully ventured into the world of short-term rentals and innovative real estate strategies. Live from their South Florida property, Matt and Lori share their inspiring journey from dissatisfying jobs to real estate success. Discover how they transitioned from traditional flips to the world of arbitrage,[...]
  • In this episode, Jeremy will be diving into the world of short-term rentals with a true expert, Brian Bockholdt. Join us as Brian shares his journey from accidental rental property owner to short-term rental powerhouse. Learn how he turned his lake house into a revenue-generating asset, the surprising financial gains he achieved, and how he's[...]
  • In this episode, Jeremy interviews Merritt, an ambitious short-term rental host who went from managing two properties to adding six more in just one year. He shares how he leveraged social media marketing, especially on platforms like Instagram Reels, to build organic reach and attract clients through referrals. Join us as we explore Merritt's journey[...]
  • In this episode, join Jeremy and Matt as they dive into the world of creative finance and real estate investment. Matt has been in the game, flipping properties and exploring unique markets like rural areas with little to no data. Discover how he approaches investment without relying on conventional wisdom and takes a proactive stance[...]
  • In this episode of the Short-Term Rental Pro podcast, join us as we dive into the unknown world of Mark Simpson, the founder and CEO of Boostly. Mark shares his fascinating journey from growing up on a 200-acre farm in the northeast of England to becoming a pioneer in the short-term rental industry. Discover how[...]
  • In this podcast episode, join Jeremy and Mike Chang in an insightful discussion about short-term rentals and their unique tax advantages. Mike, a finance expert, and short-term rental investor, shares his expertise on underwriting, maximizing cash flow, and leveraging tax benefits. Discover how to navigate the world of short-term rentals and optimize your financial growth.
  • Introducing Bailey Kramer, a 23-year-old who has a multi-6-figure Airbnb co-hosting business. Bailey focuses on both medium-term and short-term rentals, managing 11 Airbnb properties across multiple states. In this episode, we talk about strategies for landing co-host clients and tips and tricks to manage Airbnb remotely. Subscribe to my channel to learn more about Airbnb[...]
  • Introducing John Bianchi, 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[...]
  • Introducing Bill Faeth, a dynamic entrepreneur and a Real Estate Investor with a diverse range of accomplishments. As a #1 Best-Selling Author, real estate investor, Airbnb coach, and eight-figure business builder, he has made a significant impact in the entrepreneurial landscape. Bill is also a podcaster and the founder of STR WealthCon, Marketmystr and Build[...]
  • 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.
  • Introducing Patryk Swietek, a young entrepreneur who began his journey in the STR industry as a product manager at AvantStay in 2019. Despite being laid off during the Covid pandemic in 2020, Patryk's passion for STRs persisted. He purchased his first STR property in September 2021 and has been hooked ever since. Patryk's dedication has[...]
  • In this episode, Jeremy interviews Tyler Coon, a renowned realtor who has an exceptional track record in the short-term rental industry. Get ready to meet our special guest, a real estate expert who exclusively focuses on selling short-term rentals and possesses an in-depth understanding of the best markets and properties to invest in. Join us[...]
  • Welcome back the Short-Term Rental Pros Podcast! This week on the podcast, Jeremy Werden dives into the the amazing opportunities that come to you through the power of partnerships and how you can leverage your strengths in properly aligned partnerships in order to grow your short-term rental business. If you are a fan of getting[...]
  • Welcome to the STR Pro Podcast with Jeremy Werden! Our host Jeremy talks to Bryce Garris (Airbnb Superhost and social media influencer) who has built his STR business in order to give himself time freedom. They discuss how Bryce got started, his arbitrage experiences with land-lords and home-owners, and his future plans which include walking[...]
  • Welcome to the STR Pro Podcast with Jeremy Werden! The Short Term Rental Pros Podcast is dedicated to sharing knowledge, experiences, and actionable takeaways from those who have built successful short-term rental and Airbnb businesses. STR Pro aims to inspire the next generation of successful STR investors. Our host, Jeremy Werden is the founder of[...]

How Blake Dailey Expanded Into Boutique Hotels

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.