STR Like The Best by Michael Chang

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STR Like The Best by Michael Chang

Michael Chang

68 episodes

1 week ago

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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Entrepreneurship

All content for STR Like The Best by Michael Chang is the property of Michael Chang and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.

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...

Show more...

Entrepreneurship

Episodes (20/68)

STR Like The Best by Michael Chang

Why Meta & Goldman Employees Are Buying $1M+ Airbnbs (It's Not What You Think)

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...

1 week ago

26 minutes

STR Like The Best by Michael Chang

67. Raising Entrepreneurial Kids: Reputation, Likability & The “Right Room” Strategy

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 rule...

3 weeks ago

31 minutes

STR Like The Best by Michael Chang

66. Leading Airbnb Operators: Cut Your Tax Bill LEGALLY, Use Savings To Buy More Airbnbs, Grow Cash Flow

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 brand—...

1 month ago

38 minutes

STR Like The Best by Michael Chang

65. Building Together: How We Run a Business as a Couple (Without Burning Out) - STR Like The Best

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 r...

1 month ago

38 minutes

STR Like The Best by Michael Chang

64. Husband & Wife Power Duo: How We Run 40+ Airbnbs Remotely With a Global Team - STR Like The Best

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...

1 month ago

23 minutes

STR Like The Best by Michael Chang

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 of running a short-term rental business: cash flow, expense tracking, and financial controls. We cover why cash (not revenue) is the single source of truth in your business, how to capture every reimbursable dollar without adding admin headaches, and how to keep your favorite rewards credit cards i...

2 months ago

49 minutes

STR Like The Best by Michael Chang

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 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...

3 months ago

41 minutes

STR Like The Best by Michael Chang

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 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...

4 months ago

44 minutes

STR Like The Best by Michael Chang

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. 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 ⬇️ ...

5 months ago

37 minutes

STR Like The Best by Michael Chang

59. The Billboard Effect: Drive 15%+ More Profits to Your Short Term Rental Portfolio with This Strategy

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

5 months ago

1 hour 10 minutes

STR Like The Best by Michael Chang

58. How Savvy STR Investors Get Designer Furniture for 40% Less

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

6 months ago

48 minutes

STR Like The Best by Michael Chang

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

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...

7 months ago

54 minutes

STR Like The Best by Michael Chang

56. How the Karwells Raised $5.5M in 2 Years and Built a Top Airbnb Brand from Scratch

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 e...

7 months ago

52 minutes

STR Like The Best by Michael Chang

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 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! 🚀 JOI...

8 months ago

42 minutes

STR Like The Best by Michael Chang

54. The Fastest Way of Scaling Your Airbnb Management Company (Strategies that actually work) w/ Guest Federico Zimmerman

JOIN 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 Unit...

8 months ago

59 minutes

STR Like The Best by Michael Chang

53. Airbnb Hosts: AI Will Replace 90% of Your Guest Communication in 2025 (Hospitable CEO reveals exactly how he is doing it)

JOIN 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 experience...

9 months ago

56 minutes

STR Like The Best by Michael Chang

52. Short Term Rental Tax Loophole Explained (The #1 Tax Hack for Real Estate Investors)

JOIN 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 ⬇️ Ap...

9 months ago

40 minutes

STR Like The Best by Michael Chang

51. Achieving the 4-Hour Workweek Through Real Estate Investing with Jonathan Farber

JOIN 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...

10 months ago

43 minutes

STR Like The Best by Michael Chang

50. How AI is Transforming Short-Term Rental Management Forever Ft. Shahar Goldboim

JOIN 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...

10 months ago

45 minutes

STR Like The Best by Michael Chang

49. From Rental Arbitrage to Experiential Stays: Redefining the STR Playbook Ft. Isaac French

JOIN 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 th...

11 months ago

57 minutes