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PODCAST

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.

business entrepreneurship

All Episodes

26:39

Why Meta & Goldman Employees Are Buying $1M+ Airbnbs...

STR Like The Best by Michael Chang ·

2025/11/08

USE MY 5-STEP LITMUS TEST TO SEE THE PROFITABILITY OF A POTENTIAL PROPERTY: https://strlikethebest.com/litmuspod Q4 2025 Market Update: What's Actually Working Right Now Most people think high-income professionals are buying Airbnbs for cash flow. They're wrong. In this episode, Michael and Liz reveal the real reason why employees at Meta, Amazon, Blackstone, and Goldman Sachs are aggressively buying $750K-$1.5M short-term rental properties and it has everything to do with the tax code. We br...

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31:12

67. Raising Entrepreneurial Kids: Reputation,...

STR Like The Best by Michael Chang ·

2025/10/24

LEARN MY STR INVESTING & STRATEGIES 🔥 https://coaching.strlikethebest.com/7figureexit?utm_source=yt Part 4 — Taipei Series Part 3 explored how mentorship, consistency, and STR tax strategy turned business growth into leverage and legacy. Part 4 dives into how those same principles shape parenting, raising kids with judgment, integrity, and emotional intelligence in an AI-driven world. 1. From business lessons to family values, why reputation, patience, and presence matter more than

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38:39

66. How to Work Together as Husband & Wife Power Duo...

STR Like The Best by Michael Chang ·

2025/10/17

LEARN MY STR INVESTING & STRATEGIES 🔥https://strlikethebest.com/wealthyt Part 3 — Taipei Series Episode 2 showed how humility, metrics, and defined roles turned conflict into scale, systems + a global team protecting marriage and ROI; Episode 3: dives into building our media/education engine (mentors, consistency) and how STR tax strategy (incl. 100% bonus depreciation) lets high-earners buy cash-flowing assets and cut taxes. Episode Highlights: 1. From zero followers to a global

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38:16

65. How to Work Together as Husband & Wife Power Duo...

STR Like The Best by Michael Chang ·

2025/10/10

LEARN MY STR INVESTING & STRATEGIES 🔥https://strlikethebest.com/wealthyt Part 2 — Taipei Series In the previous episode, Michael and Liz shared how systems, tech, and a global team let them run ~40 STRs remotely. In this part of the series, they continue the conversation, diving into how they work together as a married team, balance decision-making with data, and turn early conflicts into a scalable structure. Episode Highlights: 1. Offloading guest comms to a global team + PMS/AI to

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23:06

64. How to Work Together as Husband & Wife Power Duo...

STR Like The Best by Michael Chang ·

2025/09/26

LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthyt From Taipei, Michael and Liz show how systems, tech, and a global team let them run ~40 STRs remotely, reclaim family time, and help clients save taxes while scaling. Episode Highlights: 1. Hands-off weekly hours, kids immersed with family and mandarin 2. Staff across 5 continents and working collectively to run 95% of business operation 3. The renewed 100% bonus depreciation spiking client deals. They...

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41:56

62. Filling the Gap: Last-Minute Bookings, OTA...

STR Like The Best by Michael Chang ·

2025/08/12

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 why relying solely on Airbnb is like owning a stock portfolio with just one stock, how to think strategically about OTA distribution, and why last-minute travelers aren’t just bargain hunters—they’re a fast-growing segment that can boost your weekday occupancy. Alex shares practical tips on integ...

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44:29

61. 0 to 300 Properties: How JJ King Built a STR...

STR Like The Best by Michael Chang ·

2025/07/12

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 deep into the early rental arbitrage days in NYC, how a cold outreach strategy turned into a SaaS acquisition, and what it takes to scale a property business sustainably in today’s market. LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod Apply to work with Michael...

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37:48

60. The Brutal Truth Of Real Estate Market Today, Why...

STR Like The Best by Michael Chang ·

2025/06/19

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. If you want to thrive in today's market and position yourself for outsized returns, this episode is a must-listen.Subscribe for more STR investor strategies every week. JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider 📖

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70:58

59. The Billboard Effect: Drive 15%+ More Profits to...

STR Like The Best by Michael Chang ·

2025/05/30

JOIN MY FREE INVESTOR COMMUNITY FOR MONTHLY COACHING & DAILY WEALTH-BUILDING STRATEGIES 🔥https://www.strlikethebest.com/insiderIn 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

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48:09

How Savvy STR Investors Get Designer Furniture for...

STR Like The Best by Michael Chang ·

2025/05/16

JOIN MY FREE INVESTOR COMMUNITY FOR MONTHLY COACHING & DAILY WEALTH-BUILDING STRATEGIES 🔥https://www.strlikethebest.com/insiderIn 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,

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54:59

57. How Mint House Founder Raised $100M After Hotels...

STR Like The Best by Michael Chang ·

2025/04/22

JOIN MY FREE INVESTOR COMMUNITY FOR MONTHLY COACHING & DAILY WEALTH-BUILDING STRATEGIES 🔥 https://www.strlikethebest.com/insider⭐ 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

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52:58

56. How the Karwells Raised $5.5M in 2 Years and...

STR Like The Best by Michael Chang ·

2025/03/28

JOIN 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

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42:17

55. Pay $17 to the IRS leveraging this tax code...

STR Like The Best by Michael Chang ·

2025/03/15

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! 🚀JOIN MY

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59:39

54. The Fastest Way of Scaling Your Airbnb Management...

STR Like The Best by Michael Chang ·

2025/02/28

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

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56:42

Airbnb Hosts: AI Will Replace 90% of Your Guest...

STR Like The Best by Michael Chang ·

2025/02/15

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

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40:20

52. Short Term Rental Tax Loophole Explained (The #1...

STR Like The Best by Michael Chang ·

2025/01/31

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 💰 Download my Free Guide: Top 10 Proven STR Amenities with Highest ROI https://www.strlikethebest.com/highestROIamenities⬇️ Apply to work with

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43:59

51. Achieving the 4-Hour Workweek Through Real Estate...

STR Like The Best by Michael Chang ·

2025/01/18

⬇️ Download my Free Guide: Top 10 Proven STR Amenities with Highest ROI https://www.strlikethebest.com/highestROIamenities⬇️ Apply to work with Mehttps://www.strlikethebest.com/getstartedIn 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

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45:56

51. How AI is Transforming Short-Term Rental...

STR Like The Best by Michael Chang ·

2025/01/03

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 wayshort 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

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57:30

Ep.49 From Rental Arbitrage to Experiential Stays:...

STR Like The Best by Michael Chang ·

2024/12/06

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. 💸 Download my Free Guide: Top 10 Proven STR Amenities with Highest

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36:09

48. The Secret to Scaling Your Short-Term Rental...

STR Like The Best by Michael Chang ·

2024/11/24

Ready to get started? You can book a strategy session to apply for my Elite Circle Mastermind.You will get exclusive access to a $5K Mastermind with me in December completely FREE if you join this month. https://www.strlikethebest.com/getstarted 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

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