STR Like The Best

Michael Chang
  • 5.0 (72)
  • Entrepreneurship
  • Weekly

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 their finances for the long term.

  1. 14h ago

    From Zero to $60K in Tax Savings at 26 (The Year-One STR Q&A With Mei and Ray)

    Most people spend years thinking about buying their first investment property. Mei and Ray did it in 6 weeks, got married in the middle of it, and saved $60K in taxes in their first year. In this episode, I sit down with Mei and Ray, 26-year-old tech workers from New York City, to break down their entire first year as STR investors, from signing the paperwork to cash flowing $60-70K in just 5 months of operation. This is one of the most honest year-one breakdowns we have done on this show. No fluff, no hype. Just two first-time investors sharing exactly what it took, what went wrong, and what the numbers actually look like after 10 months of owning their first short-term rental. We break down: How they went from zero real estate experience to under contract in 2 weeks and why getting married on Black Friday was actually a strategic tax move The $60K in tax savings they captured in year one and how their taxable income dropped to under $100K using the STR cost segregation strategy The STR license getting revoked mid-renovation and the exact steps they took to get it reinstated without losing the property How the property appreciated 13% in 10 months going from $560K to $633K while cash flowing on top of that What 15K in bookings in 3 days after relaunching looks like and why that result comes from doing the setup work right the first time How they manage a property 5 hours away on 1 to 2 hours a week and the local team structure that makes it possible The bottom line: The strategy works when you do it right, and Mei and Ray are proof that age, experience, and proximity to the property are not excuses. 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/

  2. Oct 23

    Why I’m Still Buying STRs at 7.5% (And the Done-For-You Shortcut That Will Get You Audited)

    Interest rates are climbing again. Most investors are frozen. And a wave of done-for-you services is promising to handle everything for you while you collect the tax benefit. Two problems with that picture. In this episode, Michael and Liz break down the real impact of rising interest rates on the STR market, why the asset class is more protected than most people think, and why the shortcut everyone is being sold right now is a direct path to an IRS audit. Michael spent 10 years as an investment banker at Citi and Merrill Lynch. He knows how interest rates move asset values. This is the episode he recorded because too many investors are either paralyzed by rates or rushing into arrangements that will cost them everything. We break down: Why interest rates are rising again and what is actually driving it (government deficits and AI capital demand) Why high rates are crushing hotel investors but not STR owners (the cap rate vs. comps distinction that changes everything) Why Michael is still finding deals that cashflow 8-10% even at 7.5% interest rates and what to look for What sellers know about year-end buyers and how to avoid getting squeezed on price Why done-for-you STR services void your material participation and put you directly in the IRS’s crosshairs What the 100-hour rule actually requires and why someone else logging hours on your behalf means nothing to the IRS The bottom line: Good STR deals still exist at 7.5%. But only if you do the work. The shortcut doesn’t just cost you the tax benefit. It costs you everything that comes with it. 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/

  3. Oct 9

    How She’s Getting Her Third Hamptons STR for Free (The Equity Strategy Nobody Talks About)

    Most STR investors obsess over cash flow. Ann-Marie Folan is playing a completely different game, and it’s working. In this episode, Michael sits down with Ann-Marie Folan, Manhattan real estate broker at Douglas Elliman, to break down how she built a 3-property Hamptons STR portfolio by optimizing for equity instead of cash flow. Ann-Marie bought her first East Hampton property in 2015 for $944K through a 1031 exchange from a 15-unit Queens apartment building she was desperate to offload. Today that property is worth over $2M and generating $8,750 to $11K per week. Her second, a gutted cottage she transformed into a 3-bed, 3.5-bath home on an acre, cost $925K plus $600K in renovations and is now worth close to $2.3M, booking at $14K per week. Her third, a Sag Harbor property under contract for $899K, is being funded entirely from equity pulled from the first two. Essentially free. We break down: -Why Ann-Marie chose equity over cash flow and how that decision compounded into $2M+ in Hamptons wealth -The 1031 exchange that got her out of 15 Queens apartments and into East Hampton in a single weekend -The real Hamptons STR numbers: $17K per week during COVID, $8,750 to $11K today, and what still drives premium bookings -How she spent $600K transforming a derelict cottage into a $2.3M income-producing asset -The HELOC and equity strategy she’s using to fund her third property without putting a dollar of new cash in -How she manages 3 properties alongside a full-time career selling 50+ Manhattan transactions per year The bottom line: You don’t have to choose between a great career and a great STR portfolio. You just have to know which game you’re playing. 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/

  4. Oct 2

    Making More But Keeping Less (The 3-Part Wealth Framework High Earners Miss)

    Most high earners are winning the income game and losing the wealth game. They make great money, hand half to the government, park the rest in a savings account that doesn't beat inflation, and wonder 10 years later why they don't have more to show for it. In this episode, Michael and Liz debrief their first-ever client conference, Architect Your Wealth, held in New York City with almost 100 clients flying in from across the country, and break down the exact wealth framework they've built over 10 years of STR investing. They also share the full origin story of STR Like The Best, the moment in a cold Chicago conference room that changed everything, and the new wealth management platform they just launched to help clients manage their money the right way. We break down: The Make, Keep, Grow framework and why focusing only on your income is the reason most high earners fall behind The 4-bucket wealth system Michael and Liz use personally to organize every dollar that comes in Heirmont Wealth, their new wealth management platform and how it manages their core stock and bond portfolio on a quarterly basis The Architect Your Wealth conference recap with almost 100 clients in one room in New York City and why the energy in that room felt like a milestone Why proactive financial planning at the start of the year beats reactive tax-time panic every single time The origin story of STR Like The Best from a cold February conference in Chicago to almost 30,000 LinkedIn followers and 100 podcast episodes The bottom line: Building real wealth isn't about working harder. It's about making more, keeping more, and growing what you have with a real plan. 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/

  5. Sep 25

    What 10 Years of STR Mistakes Bought Us (And Why We're Now Teaching You to Skip Them)

    If you're earning good money and still handing a massive chunk of it to the IRS every April, there's a better way. We built it the hard way so you don't have to. In this episode, Michael sits down with his partner Liz to pull back the curtain on how they built STR Like The Best from zero followers in May 2023, why they finally launched their education programs, and what 10 years of trial and error actually taught them about building real wealth through short-term rentals. This isn't a highlight reel. It's the real story of posting to 3 views, hiring mentors when they had no idea what they were doing, and building a business that now helps high-income W2 investors stop overpaying taxes and start building generational wealth. We break down: How one conference in Chicago changed everything and led to launching STR Like The Best with zero followers and no roadmap Why hiring a mentor is the single fastest way to compress 10 years of mistakes into months, and what to actually look for when choosing one The STR Concierge program: how Michael and Liz guide high-income investors through market selection, property analysis, tax strategy, and operations from start to finish Why earning $400K a year means paying $125K in taxes, and how buying an Airbnb with 100% bonus depreciation back in 2025 changes that equation completely Why building a personal brand is no longer optional in the age of AI, and why waiting even one more year makes it harder What's next: the Elite group coaching program, future fund plans, and how they're scaling to help more investors build real wealth The bottom line: Ten years of figuring it out the hard way is only worth something if someone else gets to skip the hard part. 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/

  6. Sep 18

    What Your CPA Gets Wrong About the STR Tax Loophole (100% Bonus Depreciation Is Back)

    Most high-income W-2 professionals are leaving six figures on the table every year because their accountant doesn't fully understand the short-term rental tax loophole. And with 100% bonus depreciation now back permanently, the stakes have never been higher. In this episode, I sit down with Amanda Han and Matt from Keystone CPA to give the most comprehensive breakdown of the STR tax loophole we've done on this show, covering material participation tests, audit defense, and what the new tax law means for high-income investors right now. Amanda and Matt are CPAs by day and real estate investors by night. They've helped investors across the country legally offset W-2 income using this part of the tax code, and they've seen firsthand how often good investors lose serious money simply because their accountant doesn't understand the rules. This episode fixes that. We break down: The 3 material participation tests that unlock the STR loophole (the 500-hour rule, the 100-hour rule, and the majority test most people don't know exists) and how married couples can combine hours to qualify faster The grouping election that most CPAs miss and why not having this one paragraph on your tax return is an audit risk waiting to happen once you scale beyond one property What activities count toward your hours and what don't including whether flying to your property, driving to the airport, and doing bookkeeping actually qualify How to audit-proof your STR strategy with RepsTracker, a separate phone number, a dedicated email address, and the documentation habits that make the IRS move on without a fight Why 100% bonus depreciation being permanent makes the STR loophole 2.5x more powerful than it was before the Big Beautiful Bill passed in July 2025 3 phrases that signal your CPA doesn't understand this strategy and what to do if you hear "you make too much," "you work too much at your job," or "you're not a real estate professional" The bottom line: The STR tax loophole is one of the most legitimate and powerful tools available to high-income W-2 earners, and the new tax law just made it more powerful than ever. The only thing standing between you and six figures in annual tax savings is having the right team and the right strategy. 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/

  7. Sep 11

    Why We Launched the Mentorship Program (And Why We're Sharing the Whole Playbook)

    Most high earners are stuck paying 40% in taxes year after year, trading time for money, and wondering if there's actually another way. There is. We know because we lived the exact same story. In this episode, I sit down with my co-founder Liz to share the real origin story behind STR Like The Best, why we left investment banking and a fashion career to build a 30+ property portfolio, and what finally convinced us to start teaching everything we know. This isn't a pitch. It's the behind-the-scenes conversation we've been meaning to have, covering 9 years of building, the early mistakes we made, and the four core values that drive every decision we make today. We break down: How a single Queens apartment generating $5,000 a month in cash flow changed everything in 2016 Why Liz and I left high-paying corporate careers to go all-in on short-term rentals The real reason we launched the mentorship program and why we don't just keep the playbook to ourselves The 4 core values behind every decision at STR Like The Best: family first, long-term thinking, numbers not feelings, and responsibility to our community Student success stories: from a stay-at-home mom launching her first STR to Julie and Andy scaling to 18 Airbnbs in Dallas The bigger vision for what STR Like The Best is becoming: a holistic wealth community covering tax planning, estate planning, and investing mindset The bottom line: Real estate is the tool, but the goal has always been the same. Build a life where family comes first and the money works for you, not the other way around. 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/

  8. Sep 4

    Finding the Right Property Is Just the First 10% (The Full Blueprint for a 90th Percentile STR)

    Most STR investors spend months finding the perfect market and the perfect property. Then they buy something "turnkey," take their own photos, skip the specialist designer, and wonder why their numbers fall flat. In this episode, Michael and Liz break down the complete framework for turning a good property into a 90th percentile short-term rental, from design and staging to photography and dynamic pricing. This is not about buying better. It is about executing better once you own it. Michael and Liz share the exact mistakes they made early in their own portfolio, what they changed, and why doing it right the first time creates a flywheel that compounds for years. We break down: Why "turnkey" is a trap and what a properly designed STR actually looks like The difference between an STR-specific designer and a residential designer, and why it directly impacts your returns Why we spent $5,000 on a photographer and flew him to Tennessee for 3 full days The storefront framework: how to think about design, staging, and photography as one complete package The guest experience details that drive 5-star reviews, from labeled light switches to welcome baskets at check-in Dynamic pricing and revenue management: the final piece that determines what your property actually earns The bottom line: Picking the right market and property is only the first 10%. The investors who consistently outperform are the ones who execute the design, the photography, and the operations at a level most people skip. 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/

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5
out of 5
72 Ratings

About

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 their finances for the long term.

Information

  • Creator
    Michael Chang
  • Years Active
    2023 - 2026
  • Episodes
    110
  • Rating
    Explicit
  • Copyright
    © 2026 STR Like The Best
  • Show Website
    STR Like The Best

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