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In this episode, Michael Chang and Philip Kennard discuss the evolving landscape of short-term rentals, focusing on the importance of direct bookings versus relying solely on online travel agencies (OTAs) like Airbnb. They explore the benefits and challenges of both strategies, emphasizing the need for rentalpreneurs to build trust with guests, manage payments effectively, and implement marketing strategies to capture direct bookings.

In this conversation, Michael Chang and Philip from FutureStay also discuss the importance of SEO and direct bookings for property managers, the role of Google Vacation Rentals, and the value proposition of FutureStay as a high-converting website solution. They delve into the new Airbnb policies, their implications for hosts, and the supportive nature of the hospitality community. Tune in to get all the details!

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In this episode of STR Like the Best, Michael Chang sits down with Jeff Illoulian, CEO of HostGPO, to explore how short-term rental operators can save money and streamline their furnishing process.

Jeff shares his journey from managing 150 STR units to founding HostGPO, a group purchasing organization offering discounted, hospitality-grade furniture, linens, and amenities.

They dive into the operational mistakes many hosts make, the importance of commercial-grade supplies, and how HostGPO helps elevate the quality and profitability of STR businesses.

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⭐ 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. ⭐ 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. ⭐ 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. ⭐ The episode concludes with reflections on future STR opportunities and the importance of mentorship in entrepreneurship.

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In this episode, I sit down with Sarah and Emily — better known as the Karwells — two best friends turned powerhouse STR investors who’ve 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 game… 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 — this episode will show you what’s possible when you combine heart, hustle, and high standards.  

What You’ll 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 — and what they say “no” to  

Their expansion into e-commerce and retreats, and how it's all connected  

The importance of honest underwriting (and why most deals don’t pencil)  

Chapters: 

00:00 – Introduction and Personal Reflections 

00:13 – Introducing the Guests: the Karwells 

01:38 – the Karwells' Journey into Short-Term Rentals 

03:27 – Building a Business and Partnership 

09:56 – Evolving the Business and New Ventures 

22:26 – The Importance of Community and Networking 

27:11 – Reflecting on Financial Growth 

27:19 – Understanding Wealth and Short-Term Rentals 

28:18 – The Importance of Transparency with Investors 

28:42 – Celebrating Fundraising Milestones 

29:27 – Design and Hospitality in Property Management 

31:32 – The Value of Honest Underwriting 

34:53 – Launching Retreats for Networking and Education 

40:04 – Finding the Right Deals and Investors 

45:51 – The Power of Community and Generosity 

51:39 – Closing Thoughts and Contact Information

Follow The Karwells on Instagram → @thekarwells  

Learn more about their upcoming retreats → thekarwells.space

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! 🚀

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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  

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#Airbnb #hospitality #investing #realestateinvesting #rentalarbitrage #shorttermrentals #airbnbcoach #airbnbsuperhost #howtoairbnb #airbnbarbitrage #airbnbinvesting

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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

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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

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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.

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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 you’re looking for practical insights on scaling your Airbnb business with smart tools and strategies, this episode is for you. 🎧 Tune in now!

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