Podcast
STR Like The Best
Hosted by Michael Chang · EN
Proven strategies and insights from successful STR investors and wealth-building experts. We share methods that help high-income earners protect their income, build lasting wealth, and compound their finances for the long term.
38episodes
Episodes
Newest firstAll episodes
56. How the Karwells Raised $5.5M in 2 Years and Built a Top Airbnb Brand from Scratch
Mar 28, 202500:52:58Tap to summarizeJOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider 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
Transcribe →55. Pay $17 to the IRS leveraging this tax code (Learn The #1 RE Investor Tax Hack from an Actual CPA!)
Mar 15, 202500:42:17Tap to summarizeIn 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! 🚀JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider ⬇️ Apply to work with Me https://www.strlikethebest.com/getstarted ✅ Follow Michael http://www.instagram.com/michaelchangbnb 🎙️ Subscribe to STR Like The Best on Apple or Spotify: https://podcasts.apple.com/us/podcast/str-like-the-best/id1675408369 https://open.spotify.com/show/141mIvb8qq26JgRYpyoAOa?si=f68a3fa0d8a8458d 📖 Join 6,000+ Investors on our STR Investing Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt 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.
Transcribe →54. The Fastest Way of Scaling Your Airbnb Management Company (Strategies that actually work) w/ Guest Federico Zimmerman
Feb 28, 202500:59:39Tap to summarizeJOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider 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 ⬇️ Apply to work with Me https://www.strlikethebest.com/getstarted ✅ Follow Michael http://www.instagram.com/michaelchangbnb 🎙️ Subscribe to STR Like The Best on Apple or Spotify: https://podcasts.apple.com/us/podcast/str-like-the-best/id1675408369 https://open.spotify.com/show/141mIvb8qq26JgRYpyoAOa?si=f68a3fa0d8a8458d 📖 Join 6,000+ Investors on our STR Investing Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt #Airbnb #hospitality #investing #realestateinvesting #rentalarbitrage #shorttermrentals #airbnbcoach #airbnbsuperhost #howtoairbnb #airbnbarbitrage #airbnbinvesting
Transcribe →53. Airbnb Hosts: AI Will Replace 90% of Your Guest Communication in 2025 (Hospitable CEO reveals exactly how he is doing it)
Feb 15, 202500:56:42Tap to summarizeJOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider 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 ⬇️ Apply to work with Me https://www.strlikethebest.com/getstarted ✅ Follow Michael http://www.instagram.com/michaelchangbnb 🎙️ Subscribe to STR Like The Best on Apple or Spotify: https://podcasts.apple.com/us/podcast/str-like-the-best/id1675408369 https://open.spotify.com/show/141mIvb8qq26JgRYpyoAOa?si=f68a3fa0d8a8458d 📖 Join 6,000+ Investors on our STR Investing Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt
Transcribe →52. Short Term Rental Tax Loophole Explained (The #1 Tax Hack for Real Estate Investors)
Jan 31, 202500:40:20Tap to summarizeJOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider 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⬇️ Apply to work with Me https://www.strlikethebest.com/getstarted ✅ Follow Michael http://www.instagram.com/michaelchangbnb ✅ Get Your RE Cost Seg https://get.recostseg.com/strlikethebest 🎙️ Subscribe to STR Like The Best on Apple or Spotify: https://podcasts.apple.com/us/podcast/str-like-the-best/id1675408369 https://open.spotify.com/show/141mIvb8qq26JgRYpyoAOa?si=f68a3fa0d8a8458d 📖 Join 6,000+ Investors on our STR Investing Newsletter: https://www.strlikethebest.com/subscribe?utm_source=yt
Transcribe →51. Achieving the 4-Hour Workweek Through Real Estate Investing with Jonathan Farber
Jan 18, 202500:43:59Tap to summarizeJOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider 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 Jonathan’s journey 03:09 Portfolio overview 05:54 Creative financing 09:03 Short-term rental shift 14:56 Navigating regulations 17:55 Differentiating in the market 21:10 Future business focus 27:55 Virtual assistants 31:32 Building routines and goals ⬇️ Apply to work with Me https://www.strlikethebest.com/getstarted ✅ Follow Michael http://www.instagram.com/michaelchangbnb ✅ Follow Jonathan https://www.instagram.com/jonjfarb/ ✅ Join 6,000+ Investors on our STR Investing Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt
Transcribe →50. How AI is Transforming Short-Term Rental Management Forever Ft. Shahar Goldboim
Jan 3, 202500:45:56Tap to summarizeJOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider 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! ⬇️ Apply to work with Me https://www.strlikethebest.com/getstarted ✅ Follow Michael http://www.instagram.com/michaelchangbnb 🎙️ Subscribe to STR Like The Best on Apple or Spotify: https://podcasts.apple.com/us/podcast/str-like-the-best/id1675408369 https://open.spotify.com/show/141mIvb8qq26JgRYpyoAOa?si=f68a3fa0d8a8458d 📖 Join 6,000+ Investors on our STR Investing Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt
Transcribe →49. From Rental Arbitrage to Experiential Stays: Redefining the STR Playbook Ft. Isaac French
Dec 6, 202400:57:30Tap to summarizeJOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider 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. ⬇️ Apply to work with Me https://www.strlikethebest.com/getstarted ✅ Follow Michael / http://www.instagram.com/michaelchangbnb ✅ Follow Isaac / http://www.instagram.com//isaacfrench_ 📖 Join 6,000+ Investors on our STR Investing Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt #Airbnb #hospitality #investing #realestateinvesting #rentalarbitrage #shorttermrentals #airbnbcoach #airbnbsuperhost #howtoairbnb #airbnbarbitrage #airbnbinvesting
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