STR Like The Best

STR Like The Best

By Michael ChangBusinessEntrepreneurshipEducationInvestingCourses
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STR Like The Best episodes

  • 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 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

    Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

    32 min
  • 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

    Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

    39 min
  • 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

    Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

    39 min
  • 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

    Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

    24 min
  • 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

    Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

    50 min
  • 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

    Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

    42 min
  • 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

    Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

    45 min
  • 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

    ⬇️ 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

    Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

    38 min
  • 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, 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

    Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

    1 hr 11 min
  • 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 furniture, linens, and amenities.

    They dive into the operational mistakes many hosts make, the importance of commercial-grade supplies, and how HostGPO helps elevate the quality and profitability of STR businesses.

    🤑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

    Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

    49 min

About STR Like The Best

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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…