Episodes

  • Ready to get started in Airbnb investing? Book a free strategy session with my team here. https://calendly.com/martyna-boss-str/strltb?utm_source=youtube&utm_medium=podcast&utm_campaign=podcast 

    In this episode, Michael Chang and Simon Lehmann, the the leaders in the short-term rental industry, share insights on the evolution of the industry, the impact of COVID-19, the role of technology, and the challenges faced by major OTAs.

    The conversation delves into the challenges and the future outlook of the industry. It also explores the importance of unit density, market localization, and the balance between centralized and decentralized operations.

    00:00 Evolution of the Short-Term Rental Industry

    08:04 Impact of COVID-19 on Market Penetration

    12:06 Challenges and Opportunities for Major OTAs

    24:13 Navigating the Short-Term Rental Industry: Challenges and Opportunities

    31:42 The Role of Technology and Economies of Scale in Property Management

    35:30 Unit Density and Market Localization: Driving Sales Tax Returns

    40:53 Balancing Centralized and Decentralized Operations in Property Management

    43:27 The Future Outlook for the Short-Term Rental Industry

    Connect with Simon on LinkedIn: https://www.linkedin.com/in/simon-lehmann-8375753b/

    📖 Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter: https://www.strlikethebest.com/subscribe?utm_source=yt

     

    #vacationrental #airbnb #rentalarbitrage #shorttermrentals #airbnbcoach #airbnbsuperhost #howtoairbnb #airbnbarbitrage #airbnbbusiness #airbnbinvesting

  • Ready to get started in Airbnb investing? Book a free strategy session with my team here. https://calendly.com/martyna-boss-str/strltb?utm_source=youtube&utm_medium=podcast&utm_campaign=podcast

     

    In this episode, host Michael Chang welcomes Ann Marie Folan, a real estate broker at Douglas Elliman, to discuss her journey from being a real estate attorney to a successful real estate broker and investor in Manhattan and the Hamptons. They explore Ann Marie's strategies for real estate investments, including the short-term rental market, and delve into her personal story of how she leverages property investment to build substantial equity. Ann Marie also shares insights into her operational approach, managing multiple properties, and instilling entrepreneurial skills and resilience in her daughter. The episode highlights the significance of equity building, property management, and the multifaceted aspects of successful real estate investment.

     

    00:00 Introduction and Podcast Growth

    00:26 Guest Introduction: Ann Marie Folan

    01:24 Anne Marie's Real Estate Journey

    02:10 Manhattan Real Estate Insights

    04:23 Success in the Hamptons

    08:23 First Hamptons Property Purchase

    16:00 Diverse Perspectives in Real Estate

    16:33 Optimizing for Equity Over Cash Flow

    16:47 House Number Two: A Case Study

    19:02 Managing Multiple Properties

    23:36 The Third House: A New Venture

    26:59 Teaching the Next Generation

    32:34 Concluding Thoughts and Contact Information

     

    📖 Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt

     

    🏡 Start and make money with STR Arbitrage

    💰 Build long-term wealth with STR Investing

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  • Ready to get started in Airbnb investing? Book a free strategy session with my team here. https://calendly.com/martyna-boss-str/strltb?utm_source=youtube&utm_medium=podcast&utm_campaign=podcast

     

    In this episode, host Michael Chang welcomes Sam Dundas, co-founder of Besty Ai, to discuss the transformative role of AI in the short-term rental industry. They explore how Besty Ai enhances guest communication, automates tasks, optimizes operations, and drives revenue growth for property managers. The conversation covers Sam's journey from property management to AI, the economic implications of AI adoption, potential risks, and how AI can democratize efficiency gains for both large and small operators. The episode also delves into the future of AI in rental management, emphasizing the importance of adopting AI tools to stay competitive.

    00:00 Introduction and Podcast Growth

    00:26 Welcoming the Guest: Sam Dundas

    01:21 Sam Dundas' Journey into Property Management

    02:22 Transition to Software and Founding Besty Ai

    03:27 Strategies for Short-Term Rental Investing

    08:30 The Role of Virtual Assistants in Property Management

    12:53 Introduction to Besty Ai

    19:19 AI in Property Management: Benefits and Challenges

    20:53 Future of AI in Short-Term Rentals

    29:17 Understanding AI Reasoning Engines

    29:41 The Importance of Prompting in AI

    29:47 How AI Handles Guest Questions

    30:31 Processing Layers in AI Responses

    31:29 Economics of AI in Business

    32:04 Sustainability and Cost of AI

    32:34 AI Models and Efficiency

    34:51 Future of AI and Cost Reduction

    37:30 Risks and Challenges in AI Implementation

    39:30 Impact of AI on Management Fees

    40:41 AI in Property Management

    46:49 Investor Considerations in AI

    49:52 Conclusion and Future Outlook

    Check out Besty Ai today https://www.instagram.com/getbestyai/

     

    📖 Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt

  • Ready to get started in Airbnb investing? Book a free strategy session with my team here. https://calendly.com/martyna-boss-str/strltb?utm_source=youtube&utm_medium=podcast&utm_campaign=podcast

    In this episode, Michael Chang and Sean Rakidzich share their insights on scaling an Airbnb arbitrage business. They discuss the benefits of arbitrage over buying properties, emphasizing immediate cash flow and rapid expansion.

    Sean also talks about the challenges of scaling, the significance of core values, and future growth opportunities in distressed multifamily properties.

    00:00 Introduction and Background

    06:15 Current Portfolio and Business Strategy

    09:12 Choosing Arbitrage over Buying Properties

    12:30 Benefits of Arbitrage and Cash Flow

    19:17 Scaling the Business and Lessons Learned

    41:12 Hiring the Right People

    46:20 Future Growth Opportunities Follow Sean Rakidzich on Youtube https://www.youtube.com/@AirbnbAutomated

    📖 Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt

     

  • Ready to start your short term rental investing journey? Book a FREE 1:1 strategy call with my team. https://calendly.com/martyna-boss-str/strltb?utm_source=youtube&utm_medium=podcast&utm_campaign=book%20a%20call

    In this episode of STR Like The Best, host Michael Chang interviews Zach Edelman, a Senior Account Executive at Easy Street Capital.

    Zach shares his expertise in STR lending, specifically on DSCR loans, which are ideal for short-term rental investors. He discusses the nuances of DSCR loans, their advantages over conventional loans, and his journey from underwriting to a front-facing sales role.

    This episode is essential for anyone interested in the financial aspects of short-term rental investments and looking to understand the intricacies of DSCR loans.

    00:03 Introduction to Zach Edelman and Easy Street Capital

    04:12 What are DSCR Loans?

    06:06 DSCR Loans vs. Conventional Loans

    07:50 Loan Pricing and Costs Explained

    09:45 Current Market Rates and Trends

    12:27 Zach's Professional Journey and Underwriting Experience

    15:02 Underwriting and Loan Structuring

    18:45 Key Advice for Borrowers

    32:15 Market Insights: Hot and Cooling Markets

    35:26 Loan-to-Value Ratios and Unlocking Equity

    Connect with Zach Edelman:

    Instagram: @ZachEdelmanESC

    Email: [email protected]

    📖 Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt

    💰What Type Of Short-Term Rental Host Are You? QUIZ: https://www.strlikethebest.com/ytquiz

    💰 Spotify Podcast: https://open.spotify.com/show/141mIvb8qq26JgRYpyoAOa?si=ea3dec9707d74da4

    💰Apple Podcast: https://podcasts.apple.com/us/podcast/str-like-the-best/id1675408369

  • In this episode of STR Like The Best, host Michael Chang interviews Gil Chan, the CEO and founder of Crafted Stays, who shares his journey from a tech background to becoming a successful short-term rental investor & entrepreneur.

    Gil's company helps hosts build polished websites and strategic marketing plans to drive more direct bookings. They also delve into practical tools and tactics for collecting emails, effective marketing campaigns, and leveraging social media for better ROI.

    This episode is a comprehensive guide for STR hosts looking to optimize their business and reduce OTA dependency.

     

    00:54 Gil's Background and Journey into Short-Term Rentals

    01:43 First Property and Learning Curve

    03:35 Tax Benefits of Short-Term Rentals

    08:27 Leveraging Technology and Tools

    19:32 Optimizing and Expanding the Portfolio

    24:31 Designing and Marketing for Your Target Audience

    28:19 Building a Direct Booking Strategy

    29:31 Balancing Direct Bookings and OTA Platforms

    35:35 Crafting a Professional Direct Booking Website 39:12 Effective Marketing Tactics for Direct Bookings

    48:13 Conclusion and Final Thoughts

    📖 Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter https://www.strlikethebest.com/subscr...

    🏡 Start and make money with STR Arbitrage

    💰 Build long-term wealth with STR Investing

    ⚙️ Earn back your precious time with STR automations ---------------------------------------------------------------------------------------------------------

    - What Type Of Short-Term Rental Host Are You? QUIZ: https://www.strlikethebest.com/ytquiz

    - Spotify Podcast: https://open.spotify.com/show/141mIvb...

    - Apple Podcast: https://podcasts.apple.com/us/podcast...

    #airbnbinvesting #realestateinvestor #airbnb #rentalarbitrage #shorttermrentals #airbnbcoach #airbnbsuperhost #howtoairbnb #airbnbarbitrage

  • In this episode of 'STR Like the Best,' host Michael Chang welcomes Kenny Bedwell, CEO and founder of STR Insights. They discuss the importance of data analysis for growing a short-term rental business.

    Kenny shares his personal journey from a corporate professional to owning multiple short-term rental properties. He offers insights on the best high-ROI amenities, the significance of understanding guest avatar, and practical tips for using data to make informed investment decisions.

    00:26 Guest Introduction: Kenny Bedwell

    03:18 First Short-Term Rental Experience & Challenges

    08:19 How to Underwrite Short Term Rental Investment Property

    10:38 Portfolio Management and Strategy

    27:40 STR Insights: Market Planning Tool

    31:28 Understanding Gross ROI and Market Selection

    35:33 Cash on Cash Return vs. Cash Flow

    39:34 Operational Efficiency and Automation

    46:26 Evaluating Property Upgrades and Amenities

    52:12 Data Integrity and Decision Making

    Follow Kenny Bedwell on Instagram: https://www.instagram.com/kenny_bedwell/

    📖 Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt

    🏡 Start and make money with STR Arbitrage 💰 Build long-term wealth with STR Investing

    ⚙️ Earn back your precious time with STR automations

    --------------------------------------------------------------------------------------------------------- - -- What Type Of Short-Term Rental Host Are You? QUIZ: https://www.strlikethebest.com/ytquiz

    - Spotify Podcast: https://open.spotify.com/show/141mIvb8qq26JgRYpyoAOa?si=ea3dec9707d74da4

    - Apple Podcast: https://podcasts.apple.com/us/podcast/str-like-the-best/id1675408369

     

  • In this podcast episode, I had a great chat with Mark Simpson, the founder of Boostly. We discussed strategies to enhance direct bookings for short-term rental properties.

    The discussion covers the difficulties of over-relying on Online Travel Agents (OTAs) like Airbnb and the importance of building a direct booking channel. Mark shares practical marketing and branding tips to drive traffic.

    We delve into the significance of email marketing, social proof, and leveraging influencer partnerships to create trust and retain guests. This episode is packed with actionable advice for rental hosts looking to optimize their business models and create lasting value.

    00:29 Meet Mark Simpson: Who is Boostly

    03:44 The Power and Pitfalls of Relying on OTAs

    09:34 A Deep Dive into Direct Bookings vs. OTAs

    19:48 Leveraging Technology for Direct Bookings

    22:48 Airbnb’s Branding and Trust

    24:14 Maximizing Direct Bookings and Trust Verification

    25:38 Leveraging Airbnb for Direct Traffic

    27:19 Creative Strategies for Direct Booking Success

    33:53 Building a Strong Email Marketing Strategy

    39:49 Engaging Potential Guests Through Email

    42:36 Conclusion: The Importance of Building Your Own Booking Channel

    Follow Mark Simpson on Instagram https://www.instagram.com/boostlyuk/?hl=en

    📖 Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt

    🏡 Start and make money with STR Arbitrage

    💰 Build long-term wealth with STR Investing ⚙️ Earn back your precious time with STR automations ------------------------------------------------------------------------------

    🌟 What Type Of Short-Term Rental Host Are You?

    🌟QUIZ: https://www.strlikethebest.com/ytquiz

    🌟Spotify Podcast: https://open.spotify.com/show/141mIvb8qq26JgRYpyoAOa?si=ea3dec9707d74da4

    🌟Apple Podcast: https://podcasts.apple.com/us/podcast/str-like-the-best/id1675408369

     

  • In this episode, I welcome Parker Borofsky, one of the top short-term rental lenders and an investor with an impressive portfolio, including a peacock farm. 

     

    Parker shares her journey into short-term rental investment and lending, discussing the nuances of mortgage lending, the impact of COVID-19 on the real estate market, and insights into current mortgage rates. 

     

    With Parker’s expertise in the STR lending industry, she provides a deep dive into the mortgage process, offering listeners a glimpse into the short term rental financing. Additionally, Parker and Michael explore the current market trends and how to structure investment strategies.

     

    00:00 Introduction to Parker Borofsky

    07:13 Short Term Rental Mortgage Lending Process

    04:04 Impact of COVID-19 on Real Estate

    14:32 Understanding Mortgage Rates

    28:15 Short-term Rental Market Trends

    31:50 Advice for STR Investors

     

    Follow Parker Borofsky on Instagram https://www.instagram.com/parkerborofsky

     

    📖 Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter

    https://www.strlikethebest.com/subscribe?utm_source=yt

     

    🏡 Start and make money with STR Arbitrage

    💰 Build long-term wealth with STR Investing

    ⚙️ Earn back your precious time with STR automations

     

    ---------------------------------------------------------------------------------------------------------

     

    - What Type Of Short-Term Rental Host Are You? QUIZ: https://www.strlikethebest.com/ytquiz

     

    - Spotify Podcast: https://open.spotify.com/show/141mIvb8qq26JgRYpyoAOa?si=ea3dec9707d74da4

     

    - Apple Podcast: https://podcasts.apple.com/us/podcast/str-like-the-best/id1675408369

     

    #airbnbautomated #airbnb #rentalarbitrage #shorttermrentals #airbnbcoach #airbnbsuperhost #howtoairbnb #airbnbarbitrage

     

  • In this episode, we interviewed Kevin Leong who remarkably scaled his Airbnb Arbitrage business from 0 to 81 units in just one year using business credit. Kevin shares insightful details on the catalytic role of mentorship and the undeniable power of community in supercharging progression in the business world.

     

    Key Highlights:

    ➡️The Foundation of Success: Kevin emphasizes the paramount importance of having a mentor and a support system of like-minded individuals. The community is a crucial aspect for navigating through the early stages of a business venture, providing guidance, encouragement, and a platform to learn from collective experiences.

    ➡️Confidence to Launch: What gave Kevin the confidence to plunge into the Airbnb Arbitrage business? He shares his thought process, his evaluation of risks and opportunities, and how he equipped himself to take the leap.

    ➡️Leveraging Business Credit: A significant takeaway from Kevin’s story is his strategic use of business credit as a powerful tool for leverage and how it can serve as a strong foundation for scaling a business.

    ➡️Rapid Scaling Explained: Going from 0 to 81 Airbnb units in a year seems impossible. Kevin breaks down his approach to scaling, including the strategies he employed, the challenges he faced, and how he overcame them by making calculated decisions.

    Whether you are considering Airbnb Arbitrage or any business venture, this episode offer a blueprint for leveraging community support and financial tools to scale rapidly and efficiently.

    📖 Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt 🏡 Start and make money with STR Arbitrage 💰 Build long-term wealth with STR Investing ⚙️ Earn back your precious time with STR automations ---------------------------------------------------------------------------------------------------------

    - What Type Of Short-Term Rental Host Are You? QUIZ: https://www.strlikethebest.com/ytquiz - Spotify Podcast:

    https://open.spotify.com/show/141mIvb8qq26JgRYpyoAOa?si=ea3dec9707d74da4 - Apple Podcast:

     

  • In this episode of 'STR Like the Best,' host Michael Chang invites Patrick Swietek to share his entrepreneurial journey and insights into scaling the largest short-term rental property management company in Joshua Tree market.

    00:00 Guest Introduction

    04:09 Entrepreneurial Beginnings

    10:16 Transition to Real Estate

    14:40 Scaling and Property Management in STR

    16:20 The Competitive Landscape of Joshua Tree

    20:12 Strategic Partnerships for Growth

    28:54 Building Community and STR Nation📖

    Connect with Patryk Swietek:

    https://www.instagram.com/patryk_swietek/?img_index=1

    Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt

    🏡 Start and make money with STR Arbitrage 💰 Build long-term wealth with STR Investing ⚙️ Earn back your precious time with STR automations ---------------------------------------------------------------------------------------------------------

    - What Type Of Short-Term Rental Host Are You? QUIZ: https://www.strlikethebest.com/ytquiz

    - Spotify Podcast: https://open.spotify.com/show/141mIvb8qq26JgRYpyoAOa?si=ea3dec9707d74da4

    - Apple Podcast: https://podcasts.apple.com/us/podcast/str-like-the-best/id1675408369

     

  • In this in-depth podcast episode, host Michael Chang invites real estate expert Ruben to share his journey and insights into the world of midterm rentals (MTRs). The discussion begins with Ruben's shift from considering vacation rental markets to exploring ways to optimize existing assets, emphasizing problem-solving as a key skill in business. They cover important aspects of MTRs, including the types of properties that are most suitable, how to market to corporate clients rather than traditional tenants, and how to utilize insurance niches for higher profitability. Ruben shares practical advice on asset types, the significance of proximity to the source of knowledge, and the importance of asking the right questions. The episode also touches upon the strategies for building a stable and lucrative real estate portfolio with fewer operational headaches than short-term rentals. Listener engagement is encouraged through subscribing to podcasts and utilizing available resources like the MTR insurance blueprint offered by Ruben. The podcast concludes by highlighting the power of the abundance mindset and the value of surrounding oneself with knowledgeable and generous individuals in the real estate field.

    Connect with Ruben 👇
    https://www.instagram.com/therealestateexperiment

    ----

    📖 Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter https://www.strlikethebest.com/subscribe?utm_source=podcast

    🏡 Start and make money with STR Arbitrage
    💰 Build long-term wealth with STR Investing
    ⚙️ Earn back your precious time with STR automations

    --------------------------------------------------------------------------------------------------------- -

    What Type Of Short-Term Rental Host Are You? QUIZ: https://www.strlikethebest.com/ytquiz

    Spotify Podcast: https://open.spotify.com/show/141mIvb8qq26JgRYpyoAOa?si=ea3dec9707d74da4 

    Apple Podcast: https://podcasts.apple.com/us/podcast/str-like-the-best/id1675408369 

  • Join 5,000+ Investors Who Subscribe to STR Like The Best Newsletter! Weekly tips on how to best invest your time and money in short-term rentals!

    https://www.strlikethebest.com/subscribe?utm_source=podcast

    -----------------------------------

    Youtube Link to This Podcast: https://youtu.be/lpeFea-mB38

     

  • Join 5,000+ Investors Who Subscribe to STR Like The Best Newsletter! Weekly tips on how to best invest your time and money in short-term rentals!

    https://www.strlikethebest.com/subscribe?utm_source=podcast

    -----------------------------------

    Youtube Link to This Podcast: https://youtu.be/2JaseEhGk1s

    Connect with Guest

    Monica Moscoso- https://www.instagram.com/estarcity_/

  • Join 5,000+ Investors Who Subscribe to STR Like The Best Newsletter! Weekly tips on how to best invest your time and money in short-term rentals!

    https://www.strlikethebest.com/subscribe?utm_source=podcast

    -----------------------------------

    Connect with Guest

    Jamie Lane- https://www.instagram.com/michaelchangbnb/

  • Join 5,000+ Investors Who Subscribe to STR Like The Best Newsletter! Weekly tips on how to best invest your time and money in short-term rentals!

    https://www.strlikethebest.com/subscribe?utm_source=podcast

    -----------------------------------

    Connect with Guest

    Elizabeth And Michael Chang- https://www.instagram.com/michaelchangbnb/

  • Join 5,000+ Investors Who Subscribe to STR Like The Best Newsletter! Weekly tips on how to best invest your time and money in short term rentals!

    https://www.strlikethebest.com/subscribe?utm_source=podcast

    -----------------------------------

    Connect with Guest

    Matt Gardner- https://www.instagram.com/roargardner/

  • Join 5,000+ Investors Who Subscribe to STR Like The Best Newsletter! Weekly tips on how to best invest your time and money in short term rentals!

    https://www.strlikethebest.com/subscribe?utm_source=podcast

    -----------------------------------

    Connect with Guest

    Chase Charifa- https://www.instagram.com/janchasecharifa

  • Join 5,000+ Investors Who Subscribe to STR Like The Best Newsletter! Weekly tips on how to best invest your time and money in short term rentals!

    https://www.strlikethebest.com/subscribe?utm_source=podcast

    -----------------------------------

    Connect with Guest

    Assaf Karman- https://www.instagram.com/assafkar/

  • Join 5,000+ Investors Who Subscribe to STR Like The Best Newsletter! Weekly tips on how to best invest your time and money in short term rentals!

    https://www.strlikethebest.com/subscribe?utm_source=podcast

    -----------------------------------