STR Like The Best by Michael Chang

By Michael ChangBusiness Entrepreneurship Education Investing Courses

STR Like The Best by Michael Chang episodes

November 08, 2025 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 break down:
How to legally offset $300K+ in W2 income with a single property purchase (and why paying 40% in taxes is optional if you know what you're doing)
The markets actually producing results in 2025 (Tennessee, Colorado, Pennsylvania) and which expensive Northeast markets are complete traps
A real $2M property case study where the owner is leaving $50K+ on the table annually through basic pricing mistakes (this happens more than you think)
Why this only works as a long-term hold strategy, and why trying to flip your way through this will get you destroyed by the IRS
The difference between markets with "good regulation" versus those that will make your investment impossible to operate
The bottom line: If you're making $200K-$650K in W2 income, taxes are your biggest expense, bigger than your mortgage, bigger than anything else. This episode shows you exactly how to turn that expense into your biggest wealth accelerator.
This is what they don't teach you in business school.
LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod

Apply to work with Michael: https://strlikethebest.com/applypod

Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb
27 min
October 24, 2025 67. Raising Entrepreneurial Kids: Reputation, Likability & The “Right Room” Strategy
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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 rules.

2. Teaching likability, empathy, and good manners as early superpowers for building lifelong relationships.

3. Building trust and teamwork between siblings, how shared responsibility, family rituals, and environment compound character.

Apply to work with Michael: https://strlikethebest.com/applyyt

Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb
LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod

Apply to work with Michael: https://strlikethebest.com/applypod

Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb
32 min
October 17, 2025 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—how mentorship and daily consistency fueled growth.

2. Turning STR experience into education, helping high-income earners build wealth and save six figures in taxes.

3. The roadmap ahead, community growth, elite vs. concierge programs, and future events + fund vision.

Apply to work with Michael: https://strlikethebest.com/applyyt

Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb
LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod
Apply to work with Michael: https://strlikethebest.com/applypod
Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb
LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod

Apply to work with Michael: https://strlikethebest.com/applypod

Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb
39 min
October 10, 2025 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 remove emotion and reclaim focus

2. Switching from per-bedroom to whole-unit stays for better ops, guest experience, and profits

3. Respecting strengths (design vs. finance), 80/20 time management, and hiring A-players

They end this episode on how mutual respect and structured delegation strengthen both the business and the marriage, teeing up Part 3 on scaling the media and education side of their brand.

Apply to work with Michael: https://strlikethebest.com/applyyt

Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb
LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod

Apply to work with Michael: https://strlikethebest.com/applypod

Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb
39 min
September 26, 2025 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 close on why sharing their playbook grows an abundance-minded network and tee up the next episode on exactly how they split roles and keep the machine smooth.

Apply to work with Michael: https://strlikethebest.com/applyyt

Follow Michael on Instagram: / michaelchangbnb
LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod

Apply to work with Michael: https://strlikethebest.com/applypod

Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb
24 min
August 29, 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 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 in play while still integrating all your spend into one clean system.
John shares his journey from investment banking to Starwood Hotels, HotelTonight, and Airbnb, and how those experiences shaped Topkey’s mission to simplify the messy financial workflows in STRs. We also swap stories on leaving banking, building businesses with our spouses, and why the why behind your business matters just as much as the tools you use.
Whether you’re managing 5 units or 50, this episode will show you how to run tighter books, free up headspace, and ultimately build a business that supports the life you want.
LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod

Apply to work with Michael: https://strlikethebest.com/applypod

Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb
50 min
August 12, 2025 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 integrating with Whimstay, avoiding the “race to the bottom” on pricing, and meeting the needs of the next-gen traveler (21–35 year olds booking 8–10 trips a year). We also talk about the importance of focusing on what is working in your business, and the role gratitude and key relationships play in the journey.
Whether you’re looking to maximize revenue, diversify your booking channels, or simply reframe your mindset as an operator, this episode delivers both tactical strategies and a reminder to enjoy the people you meet along the way.
LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod

Apply to work with Michael: https://strlikethebest.com/applypod

Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb
42 min
July 12, 2025 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: https://strlikethebest.com/applypod

Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb
45 min
June 19, 2025 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.
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⬇️ Apply to work with Me https://www.strlikethebest.com/getstarted
✅ Follow Michael http://www.instagram.com/michaelchangbnb
✅ Follow Avery http://www.instagram.com/@TheAveryCarl

LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod

Apply to work with Michael: https://strlikethebest.com/applypod

Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb
38 min
May 30, 2025 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 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!
🤑Get my free Airbnb Launch Guide by joining 6,000+ Investors on our STR Investing Newsletter https://www.strlikethebest.com/subscribe?utm_source=yt
⬇️ 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

LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod

Apply to work with Michael: https://strlikethebest.com/applypod

Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb
1 hr 11 min

About STR Like The Best by Michael Chang

From the publisher's feed

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.