STR Like The Best

Michael Chang
  • 5.0 (72)
  • Entrepreneurship
  • Updated 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. 6d ago

    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/

  2. Aug 28

    Stop Using AI as a Better Google (3 Ways It Actually Makes You Money in STR)

    Most people using AI like a search engine are leaving serious money on the table. If you're typing one-off questions on a free plan and calling it a day, you're running one of the most powerful tools available at about 5% of its actual capacity. In this episode, I sit down with Liz to break down exactly how we use AI across our 30+ property portfolio, from analyzing inspection reports before we close to solving guest issues without sending a repair person out at 11pm. These are not theories. These are the exact systems we use every week, and why we spend $500 a month on AI subscriptions without hesitating. We break down: Why the free plan is actively working against you and why $25 a month is the best investment you can make this year How to upload a 60-page inspection report and have AI act as your personal property inspector, pulling the 5 biggest issues, projected repair costs, and best and worst case scenarios The adversarial AI method: how I pit Claude against ChatGPT on high-stakes decisions to stress test answers and catch hallucinations before they cost me money Why AI makes you a better client, and how I used it to push back on an attorney who kept giving me hand-wavy answers on our corporate structure How we build a separate AI project for every property we own, loaded with appliance manuals, vendor contacts, and inspection reports, so our VA team solves guest issues in minutes instead of days The project context file technique that keeps your AI sharper with every session instead of starting from scratch each time The bottom line: AI does not replace your expertise. It multiplies it. The operators who figure this out are building a permanent edge over everyone still treating it like a better Google. 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. Aug 21

    We Wasted Time on a Real Estate License (The 100-Hour Strategy for W-2 Couples)

    Most high-income couples assume getting a real estate license is the shortcut to real estate tax benefits. We made that exact mistake in 2018, and it cost us years of going down the wrong path. In this episode, I sit down with Liz to break down the real difference between Real Estate Professional Status and the STR tax loophole, and why one works for almost every W-2 couple and the other almost never does. We recorded this one just the two of us because this question comes up constantly with our clients and we wanted to put the whole framework in one place. No fluff, just the mechanics, the mistakes, and the exact questions you need to ask your CPA before you do anything. We break down: Why 99.99% of W-2 couples don't qualify for REPS, and why a real estate license changes absolutely nothing The 100-hour material participation rule and why it's achievable even when both spouses are working full time What hours actually count toward material participation, and the investor hours the IRS will never give you credit for Why your CPA is not your tax strategist, and why that responsibility falls entirely on you The Schedule C vs. Schedule E test: one question that tells you immediately whether your CPA actually understands this strategy Why it's still possible to execute the STR loophole this tax year, even if you're starting in August The bottom line: Taxes are your single largest expense. The STR loophole is the most accessible tool a dual-income couple has to keep more of what they earn, but only if you understand how it actually works. 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. Aug 14

    The Empty Nester Problem Nobody Talks About (Identity, Marriage, and $1.5M in Tax Savings)

    Most couples don't realize the empty nester transition is three separate problems, not one. And most of them hit all three at the same time, completely unprepared. In this episode, Liz and I sit down to break down what actually happens when the kids leave, why stay-at-home parents lose more than just a routine, and how short-term rental investing solves all three problems at once. This isn't just a real estate episode. It's a life design episode. We share what we've learned from building an STR portfolio together, the hard conversations we had along the way, and why we believe this is the single best vehicle for any couple heading into the empty nester phase. We break down: The three-part identity crisis stay-at-home parents face when the kids leave and why going back to work isn't the answer for most people How building an STR business together gives both spouses a separate identity and a shared project at the same time The 100-hour material participation rule and why married couples filing jointly have an advantage most people completely miss How Liz and I divide lanes in our business, why the first year is hard, and what we figured out that made it work Why our kids already have a bigger Roth IRA than I had in my 20s and how we fund it through the STR business Why waiting until you're 60 to build this life is the one mistake we're glad we didn't make The bottom line: The empty nester transition doesn't have to mean losing your identity, drifting from your spouse, and hoping your 401k holds. STR gives you all three things back at once. 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. Aug 7

    How One STR Property Can Save $370K in Taxes (And Why We're Never Selling It)

    Most investors think the endgame is to buy, hold, and eventually sell. But selling might be the most expensive decision you ever make. In this episode, Michael and Liz share a real-time breakdown of their newest short-term rental, a $2.4M Tennessee property launched July 1st, covering the actual cash flow numbers, the tax strategy behind it, and why they plan to hold it for generations. This is one of the most transparent, numbers-first episodes we've done. No hypotheticals. Just the real performance data, the cost segregation results, and the Section 1014 strategy that changes how you think about real estate as a long-term wealth tool, all recorded while managing the property from 12 time zones away in Taiwan. We break down: How the property hit $30K in revenue and 82% occupancy in its very first month, before professional photos were even live Why the cost segregation study is projecting $800K to $1M+ in protected taxable income from this single property, and how an on-site engineering study could push that number even higher The Section 1014 strategy that lets you pass real estate to your kids completely free of capital gains tax and depreciation recapture How Michael and Liz manage 12 properties remotely in about an hour a day each, whether they're in New York or 12 time zones away Why they only use 30-year fixed-rate debt, never underwrite a refinance, and model a conservative 3% annual appreciation when analyzing a deal How $370K in projected tax savings effectively returns more than half their original cash investment in year one The bottom line: The real power of STR investing isn't just the cash flow. It's what happens when you stack cost segregation, bonus depreciation, and Section 1014, and hold the asset long enough to change your family's financial future. 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. Aug 7

    How Our 8 STRs Let Us Live in Taiwan for 7 Weeks (And Why the Money Was Never the Point)

    Most people building passive income are chasing a number. We were chasing something else entirely. In this episode, Michael and Liz sit down together from Taipei, Taiwan, where they're spending their third consecutive summer with their kids, to share the real reason they built their STR portfolio and what time freedom actually looks like in practice. This isn't a theory episode. It's a behind-the-scenes look at how two former investment banking and fashion professionals designed a life where the portfolio works while they're sleeping, the kids are in $45 swim lessons four days a week, and the whole family is under one roof for seven weeks straight. We break down: How 8 short-term rentals generate $200K+ in July revenue while Michael and Liz are 12 time zones away The real cost breakdown of 7 weeks in Taiwan, including flights, summer camp, and personal training, and why it costs a fraction of what it would in New York The daily schedule that lets them work 8 to 12, spend afternoons with their kids, and still meet their 500-hour material participation requirement for the STR tax benefit How a team of nearly 10 specialists provides 24-hour client support across Slack so their mentorship program never misses a beat while they sleep Liz's golden handcuff story and why 10 vacation days a year was never going to be enough The immigrant parent story that became the North Star for everything Michael has built The bottom line: The STR portfolio isn't the point. The time it buys you is. 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. Jul 24

    The Skill Corporate America Punishes That Real Estate Rewards

    Corporate America trained you to be guarded, competitive, and quiet. That mindset will keep you stuck in real estate. In this episode, I sit down with my co-founder and wife, Liz, to talk about the single biggest unlock in our investing journey and why we built everything we have around it. This is not a guest episode. It is one of the most honest conversations we have had on the podcast. We break down exactly how community has shaped every deal, every breakthrough, and every key hire in our business, from our first property to a 30-plus property portfolio generating $2.3M a year. We break down: How one conversation at a conference in Chicago sparked our entire education business and the 1,100-person community we have today Why the zero-sum mindset that corporate America drills into high earners is the exact thing holding them back from building real wealth The full breakdown of our mentorship program: 150-plus investors, 20 people on client success, and the 7 specialists we deploy at every stage of your journey How we built our entire Catskills team from scratch on a $1M property without knowing a single person in the market The give-and-take framework that turned Liz from a self-described introvert into someone who asks for help and gets it Why the investors who move fastest in our program are the ones who plug into the community on day one The bottom line: You cannot build a real estate portfolio worth having in an information vacuum. The right community is not a nice to have. It is your single biggest competitive advantage. 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. Jul 17

    Productivity Isn't About Doing More (It's About What You Stop Doing)

    Most people think being productive means doing more, working faster, or squeezing in one more task. That's not how we do it. In this episode, I sit down with Liz to break down the exact system behind running two businesses, growing to 113,000 social media followers, and raising two kids under 5 at the same time. This isn't theory. These are the exact hires we made, the things we stopped doing, and the mindset shifts that made all of it possible. We break down: Why productivity is a subtraction game, not an addition game, and the sculptor analogy that reframed how we think about our time How we built a team of 17 people across 5 continents we have never met face to face, and why the distance stopped mattering The domestic hires that eliminated most of our relationship friction: cleaners, grocery delivery, and the postpartum nanny that changed Liz's recovery after our first kid Why letting go of control is not about lowering your standards, and how KPIs tell you everything you actually need to know The one rule we never break as business partners and spouses, and why violating it makes you both look bad How buying back our time at home made us more present parents to Athena and Jackson The bottom line: If you're still doing everything yourself, you're not being productive. You're just busy. 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
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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
    103
  • Rating
    Explicit
  • Copyright
    © 2026 STR Like The Best
  • Show Website
    STR Like The Best