Afleveringen
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β In this conversation, Michael Chang interviews William Lucas, the chairman of Mint House, a leading company in corporate housing and short-term rentals. William shares his entrepreneurial journey, the inception of Mint House, and the challenges & strategies involved in raising capital and building a scalable team. β They highlight the importance of technology in hospitality, the need for a strong brand in the short-term rental market, and the significance of hiring the right people to drive business success. β The discussion also covers the decision-making process between buying properties versus managing them, and Will shares insights from his transition to a chairman role. β The episode concludes with reflections on future STR opportunities and the importance of mentorship in entrepreneurship.
π€Get my free Airbnb Launch Guide by joining 6,000+ Investors on our STR Investing Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt
β¬οΈ Apply to work with Me https://www.strlikethebest.com/getstarted
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In this episode, I sit down with Sarah and Emily β better known as the Karwells β two best friends turned powerhouse STR investors whoβve raised over $5.5 million from everyday investors, built a thriving portfolio of uniquely designed Airbnbs, and launched a brand that spans education, e-commerce, retreats, and more.
We talk about how they evolved from scrappy designers working for free to learn the gameβ¦ to running a full-fledged STR operation that prioritizes community, creativity, and transparency. Whether you're an aspiring host, capital raiser, or someone building a brand in this space β this episode will show you whatβs possible when you combine heart, hustle, and high standards.
What Youβll Learn:
How the Karwells raised $5.5M+ in equity capital for STR deals
Why design, hospitality, and investor trust are their edge
How they balance friendship and business (and why it actually makes them stronger)
The power of community and building in public
What makes a deal worth doing β and what they say βnoβ to
Their expansion into e-commerce and retreats, and how it's all connected
The importance of honest underwriting (and why most deals donβt pencil)
Chapters:
00:00 β Introduction and Personal Reflections
00:13 β Introducing the Guests: the Karwells
01:38 β the Karwells' Journey into Short-Term Rentals
03:27 β Building a Business and Partnership
09:56 β Evolving the Business and New Ventures
22:26 β The Importance of Community and Networking
27:11 β Reflecting on Financial Growth
27:19 β Understanding Wealth and Short-Term Rentals
28:18 β The Importance of Transparency with Investors
28:42 β Celebrating Fundraising Milestones
29:27 β Design and Hospitality in Property Management
31:32 β The Value of Honest Underwriting
34:53 β Launching Retreats for Networking and Education
40:04 β Finding the Right Deals and Investors
45:51 β The Power of Community and Generosity
51:39 β Closing Thoughts and Contact Information
Follow The Karwells on Instagram β @thekarwells
Learn more about their upcoming retreats β thekarwells.space
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In this episode, Michael Chang and Thomas Castelli, CPA, break down essential tax strategies for short-term rental investors. Learn how to leverage the "short-term rental tax loophole" to offset W-2 income, maximize depreciation benefits, and avoid common tax pitfalls. They also discuss material participation rules, bookkeeping best practices, and key deductions to optimize your financial outcomes. Don't miss these expert insights to grow your wealth through smart tax planning! π
JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES π₯ -https://www.strlikethebest.com/insiderβ¬οΈ Apply to work with Me https://www.strlikethebest.com/getstarted
β Follow Michael http://www.instagram.com/michaelchangbnb
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In this episode, the host discusses the principle of not letting tax benefits dictate investment decisions with Thomas Castelli. The conversation focuses on ensuring that property investments make sense financially on their own rather than being driven by potential tax depreciation. The discussion also touches on the complexities and time commitments involved in managing properties, especially when one does not live in proximity to them.
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In this episode, host Michael Chang interviews Federico Zimmerman, a seasoned property manager operating a short-term rental management company with 65 properties across 12 states in the U.S. Federico shares his inspirational journey of transitioning from a corporate career in Argentina to starting and scaling a successful short-term rental business in the United States. He highlights the challenges and key decisions involved in building his business, the importance of networking, and the complexities of managing multiple properties remotely. This episode provides valuable insights for aspiring property managers and anyone looking to optimize their short-term rental operations.
CHAPTERS:
00:00 Introduction and Career Reflections
00:21 Welcoming Federico Zimmerman
01:38 Federico's Journey in Short-Term Rentals
05:17 Challenges and Growth in Property Management
11:34 The Leap to the United States
20:53 Starting Over and Building Success
24:59 Strategic Growth and Partnerships
30:14 Building Your Business Through Relationships
30:51 Strategic Property Management
31:54 Managing Properties Across States
33:46 Operational Challenges and Solutions
35:12 The Importance of a Strong Team
37:21 Client and Guest Expectations
40:47 The Value of Property Management
45:56 Learning from Mistakes and Moving Forward
51:13 The People Behind the Business
52:59 Final Thoughts and Reflections
β¬οΈ Apply to work with Me
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π Join 6,000+ Investors on our STR Investing Newsletter
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In this episode, Michael Chang interviews Pierre-Camille Hamada, CEO of hospitable.com, discussing the transformative impact of AI technology on short-term rental management. Pierre shares his unique journey from a law career to founding a leading property management software, emphasizing the importance of automation and technology in enhancing guest experiences and streamlining operations for hosts. The conversation explores the current landscape of property management systems, the underserved market of small hosts, and the critical balance between distribution and automation in maximizing rental business efficiency
β¬οΈ Apply to work with Me
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β Follow Michael
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02:54 Understanding the Value of Cost Segregation
06:03 The Role of CPAs in Real Estate Investing
08:55 Short-Term Rentals and Tax Benefits
14:45 The Future of Cost Segregation and Legislative Changes
17:57 Real-Life Examples and Case Studies
20:47 When Cost Segregation May Not Be Beneficial
24:06 The Importance of Control in Real Estate Investing
β¬οΈ Apply to work with Me https://www.strlikethebest.com/getstarted
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In this episode, Michael Chang interviews Jonathan Farber, a successful real estate investor and entrepreneur. Jonathan shares his journey from a sales software company to building a diverse real estate portfolio, including short-term rentals. He discusses creative financing strategies, the shift to short-term rentals during COVID, and the importance of market dynamics in real estate investing.
00:00 Intro to Jonathanβs journey03:09 Portfolio overview05:54 Creative financing09:03 Short-term rental shift14:56 Navigating regulations17:55 Differentiating in the market21:10 Future business focus27:55 Virtual assistants31:32 Building routines and goalsβ¬οΈ Apply to work with Me https://www.strlikethebest.com/getstarted
β Follow Michael http://www.instagram.com/michaelchangbnb
β Follow Jonathan https://www.instagram.com/jonjfarb/
β Join 6,000+ Investors on our STR Investing Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt -
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In this episode of STR Like the Best, Michael Chang sits down with Shahar Goldboim, CEO of Boom AI, to explore how artificial intelligence is reshaping the way short term rental hosts and property managers operate.
From centralizing tasks to boosting efficiency and increasing revenue, Shahar shares the innovative strategies behind Boom AI.
Shahar also opens up about his journey of scaling a property management business, the importance of building a great team, and how technology can address some of the toughest challenges in the short-term rental industry.
Episode Highlights:
00:00 Building a Winning Team
00:21 Introduction to Property Management Systems
01:06 Guest Introduction: Shahar Goldblum
02:51 The Importance of a Centralized PMS
05:21 Scaling with a PMS: A Personal Story
12:02 AI Integration in Property Management
22:24 Revolutionizing Customer Support with AI
24:03 Challenges in the Property Management Industry
31:05 The Power of Networking and Mentorship
If youβre looking for practical insights on scaling your Airbnb business with smart tools and strategies, this episode is for you. π§ Tune in now!
β¬οΈ Apply to work with Me
https://www.strlikethebest.com/getstarted
β Follow Michael
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ποΈ Subscribe to STR Like The Best on Apple or Spotify:
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π Join 6,000+ Investors on our STR Investing Newsletter
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In this episode of STR Like The Best, Michael Chang sits down with leading hospitality entrepreneur Isaac French to discuss thriving in the ever-evolving short-term rental market.
Michael and Isaac dive into the dynamics of scaling a traditional rental business versus crafting unique accommodations, and what investors should know in order to strike the right balance between these two strategies.
β¬οΈ Apply to work with Me https://www.strlikethebest.com/getstarted
β Follow Michael / http://www.instagram.com/michaelchangbnb
β Follow Isaac / http://www.instagram.com//isaacfrench_
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#Airbnb #hospitality #investing #realestateinvesting #rentalarbitrage #shorttermrentals #airbnbcoach #airbnbsuperhost #howtoairbnb #airbnbarbitrage #airbnbinvesting
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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 β Introduction: Scaling in 2025 & Beyond
01:22 β Caleb's Vision for the Future of STR Business
04:55 β Revenue Management: Your Secret Weapon
11:45 β Innovative Business Models for Scalability
17:59 β Leveraging Local Knowledge Globally
22:43 β Effective Hiring Strategies for Modern Challenges
34:25 β Conclusion: Your Roadmap to Success
π Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter https://www.strlikethebest.com/subscribe
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π° Build long-term wealth with STR Investing
βοΈ Earn back your precious time with STR automations
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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.
Heβll 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 Remotely10:40 Transitioning to Property Management in Madrid
19:39 Investing in Real Estate and Building a Portfolio25:34 The Importance of Relationships in Business
Watch more on Youtube: https://www.youtube.com/@michaelchangbnb?sub_confirmation=1 -
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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 -
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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/airbnbhostshelpinghostsπ Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt
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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
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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
π Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt
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π° Build long-term wealth with STR Investing
βοΈ Earn back your precious time with STR automations
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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/
π Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt
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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
π Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt
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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]
π Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt
π°What Type Of Short-Term Rental Host Are You? QUIZ: https://www.strlikethebest.com/ytquiz
π° Spotify Podcast: https://open.spotify.com/show/141mIvb8qq26JgRYpyoAOa?si=ea3dec9707d74da4
π°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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π‘ Start and make money with STR Arbitrage
π° Build long-term wealth with STR Investing
βοΈ 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
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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/
π Join 5,000+ Investors Who Subscribe to the STR Like The Best Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt
π‘ Start and make money with STR Arbitrage π° Build long-term wealth with STR Investing
βοΈ Earn back your precious time with STR automations
--------------------------------------------------------------------------------------------------------- - -- What Type Of Short-Term Rental Host Are You? QUIZ: https://www.strlikethebest.com/ytquiz
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