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In this episode of STR Like The Best, host Michael Chang sits down with industry expert Caleb Shore to reveal strategies for scaling your short-term rental business in the evolving landscape of 2025 and beyond.

Tune in to learn how to:

- Leverage advanced revenue management to maximize profits.

- Master effective hiring techniques for building a strong team, even in tough markets.

- Utilize virtual assistants to streamline and expand your operations.

- Tap into emerging markets like Charlotte, North Carolina, for growth opportunities. Turn local insights into a competitive edge in a global industry.

- Whether you're starting out or aiming to scale up, this episode offers valuable insights to help you stay ahead in the short-term rental game.

 

Key Moments:

00:00 The Hiring Mistake That Changed Everything

00:19 – Introduction: Scaling in 2025 & Beyond

01:22 – Caleb's Vision for the Future of STR Business

04:55 – Revenue Management: Your Secret Weapon

11:45 – Innovative Business Models for Scalability

17:59 – Leveraging Local Knowledge Globally

22:43 – Effective Hiring Strategies for Modern Challenges

34:25 – Conclusion: Your Roadmap to Success

 

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Today, I'm thrilled to be joined by STR Like The Best coaching member Jaime Cabal! In less than a year after joining the program, Jaime has scaled his Airbnb business into a thriving global operation and investment portfolio.

He’ll be sharing the strategies, pivotal decisions, and insights that fueled his rapid success in the short-term rental industry

00:00 Introduction to Jaime Cabal's Journey
02:16 Launching the Airbnb Business in Miami
06:43 Managing Airbnb Units Remotely

10:40 Transitioning to Property Management in Madrid
19:39 Investing in Real Estate and Building a Portfolio

25:34 The Importance of Relationships in Business

Watch more on Youtube: https://www.youtube.com/@michaelchangbnb?sub_confirmation=1

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JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider 

In this episode of 'STR Like The Best,' host Michael Chang interviews seasoned investor Michael McKay about advanced real estate negotiation strategies and the evolution from Airbnb to property flipping.

They discuss McKay's focus on solving sellers' problems, his business model in Jacksonville, Florida, and the significance of knowing oneself in business.

The conversation covers marketing strategies, short-term rental insights, unique renovations, and adapting to market changes. Key takeaways include understanding seller motivations, building a competent sales team, and leveraging local regulations for competitive advantage.

The episode concludes with advice on networking and securing sales jobs in real estate, emphasizing mentorship and the impact of strategic connections.

00:00 Introduction to Real Estate Negotiation

00:24 Meet Michael McKay: From Airbnb to Real Estate Flipping

01:12 Michael McKay's Journey in Real Estate

02:21 Transition to Jacksonville and Real Estate Strategy

06:13 Building a Real Estate Business in Jacksonville

08:58 Direct to Seller Acquisitions and Flipping Strategy

19:29 Success Stories and Unique Deals

23:48 Sales Staff and Hiring Plans

24:26 Impact of Market Changes on Real Estate

26:56 Shift from Institutional to Retail Buyers

28:16 Adapting to Market Conditions

32:01 Lessons from Short-Term Rental Investments

35:54 Unique Property Features for Success

45:03 Networking and Mentorship in Real Estate

48:35 Conclusion and Contact Information

Follow Michael Mckay On Socials..
Instagram: https://www.instagram.com/mike_mckay
YouTube: https://www.youtube.com/channel/UC3Aqb0ex_lWuJ-3wdsBPUtg

LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod

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JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider 

In this episode, host Michael Chang engages with guest Chewy, a seasoned short-term rental entrepreneur, discussing pathways to success in the Airbnb market.

They cover Chewy's journey from commercial real estate to short-term rentals, leveraging word of mouth for podcast growth, and the power of social media in forming valuable connections.

Chewy shares his experiences of starting out in Shanghai, applying lessons from arbitrage, and managing 25 rental units several years later.

They also tackle challenges such as copyright issues and the benefits of partnership in entrepreneurship.

The episode concludes with insights into the importance of taking calculated risks and maintaining an abundance mindset for continued success.

00:00 Introduction and Podcast Growth

00:21 Welcoming Chewy and Initial Conversation

01:49 Chewy's Background and Journey to Real Estate

02:55 First Experience with Arbitrage

06:51 Learning from Courses and Finding a Business Partner

14:34 Challenges and Growth in Arbitrage

18:31 Balancing Vacation and Business Rentals

20:48 Navigating Business Partnerships

22:11 The Importance of Trust in Business

25:36 Dealing with Legal Challenges

29:37 The Value of Solving Problems with Money

34:30 Building a Supportive Community

37:26 The Power of Generosity in Business

Follow Chewy On Socials.. 
Instagram: https://www.instagram.com/chewyyyl
Facebook. Group: https://www.facebook.com/groups/airbnbhostshelpinghosts

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LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod

Apply to work with Michael: https://strlikethebest.com/applypod

Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider 

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/

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

LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod

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JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider 

 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

 

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🏡 Start and make money with STR Arbitrage

💰 Build long-term wealth with STR Investing

⚙️ Earn back your precious time with STR automations

LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod

Apply to work with Michael: https://strlikethebest.com/applypod

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JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider 

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/

 

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JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider 

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

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JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider 

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]

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💰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

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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

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🏡 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

LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod

Apply to work with Michael: https://strlikethebest.com/applypod

Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb