STR Like The Best by Michael Chang
Conversations with the best short term rental investors and business leaders in the world. We explore their ideas, methods, and stories to help you better invest your time and money.
- Update frequency
- every 13 days
- Average duration
- 41 minutes
- Episodes
- 63
- Years Active
- 2023 - 2025
63. From Spreadsheets to Scale: How Topkey Streamlines STR Finances (Without Losing Your Rewards Points)
In this episode of STR Like the Best, I sit down with John from Topkey—a financial operating system built specifically for property managers—to talk about the “unsexy” but absolutely essential side o…
62. Filling the Gap: Last-Minute Bookings, OTA Strategy, and Focusing on What’s Working in Your STR Business
In this episode of STR Like the Best, I sit down with Alex Alioto, Co-Founder and Head of Growth at Whimstay, an OTA built specifically to fill your last-minute and gap-night inventory.
We break down …
61. 0 to 300 Properties: How JJ King Built a STR Property Management Company from Scratch
In this episode, I sit down with JJ King—STR operator, ex-product lead, and serial entrepreneur—who scaled from answering Craigslist ads to running a 300-unit property management company. We dive dee…
60. The Brutal Truth Of Real Estate Market Today, Why It Matters to YOU?
In this week's episode, Michael Chang and Avery Carl, CEO of The Short-Term Shop, break down the brutal reality of today’s short-term rental market and why that’s exactly where the opportunity lies. …
59. The Billboard Effect: Drive 15%+ More Profits to Your Short Term Rental Portfolio with This Strategy
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In this episode, Michael Chang and Philip Kennard discuss the evolving …
58. How Savvy STR Investors Get Designer Furniture for 40% Less
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In this episode of STR Like the Best, Michael Chang sits down with Jeff…
57. How Mint House Founder Raised $100M After Hotels Rejected Him
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⭐ In this conversation, Michael Chang interviews William Lucas, the cha…
56. How the Karwells Raised $5.5M in 2 Years and Built a Top Airbnb Brand from Scratch
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In this episode, I sit down with Sarah and Emily — better known as the Karwells —…
55. Pay $17 to the IRS leveraging this tax code (Learn The #1 RE Investor Tax Hack from an Actual CPA!)
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 …
54. The Fastest Way of Scaling Your Airbnb Management Company (Strategies that actually work) w/ Guest Federico Zimmerman
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In this episode, host Michael Chang interviews Federico Zimmerman, a seasoned prope…
53. Airbnb Hosts: AI Will Replace 90% of Your Guest Communication in 2025 (Hospitable CEO reveals exactly how he is doing it)
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In this episode, Michael Chang interviews Pierre-Camille Hamada, CEO of hospitable.…
52. Short Term Rental Tax Loophole Explained (The #1 Tax Hack for Real Estate Investors)
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02:54 Understanding the Value of Cost Segregation
06:03 The Role of CPAs in Real Es…
51. Achieving the 4-Hour Workweek Through Real Estate Investing with Jonathan Farber
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In this episode, Michael Chang interviews Jonathan Farber, a successful real estate…
50. How AI is Transforming Short-Term Rental Management Forever Ft. Shahar Goldboim
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In this episode of STR Like the Best, Michael Chang sits down with Shahar Goldboim,…
49. From Rental Arbitrage to Experiential Stays: Redefining the STR Playbook Ft. Isaac French
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In this episode of STR Like The Best, Michael Chang sits down with leading hospital…
48. The Secret to Scaling Your Short-Term Rental Empire in 2025 & Beyond w/ Guest Caleb Shore
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In this episode of STR Like The Best, host Michael Chang sits down with industry ex…
47. How Jaime Cabal Built a Global Airbnb Business in a Year
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Today, I'm thrilled to be joined by STR Like The Best coaching member Jaime Cabal!…
46. Stop Leaving Money on the Table: Learn How to Solve Seller Problems with Guest Michael McKay
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In this episode of 'STR Like The Best,' host Michael Chang interviews seasoned inve…
45. Growth, Grit, and Partnerships: Chewy’s 2-Year STR Story
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In this episode, host Michael Chang engages with guest Chewy, a seasoned short-term…
44. Evolution and The Future Outlook of Short Term Rental Industry
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In this episode, Michael Chang and Simon Lehmann, the the leaders in the short-term…