STR Like The Best

Michael Chang
  • 5.0 (71)
  • 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. 4d ago

    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/

  2. 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/

  3. 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/

  4. 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/

  5. 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/

  6. Jul 10

    $220K in Taxes Saved From One Purchase (The STR Formula Even Real Estate Attorneys Miss)

    Most people think owning Hamptons real estate means success. Ann Marie Folan had two properties there and was still throwing cash at them every month just to keep the lights on. In this episode, I sit down with Ann Marie Folan, former Wall Street real estate attorney and one of Manhattan's most prominent brokers, to break down how she went from bleeding cash on two Hamptons properties to running a 5-property portfolio on track for over $800K this year. Ann Marie came in with more real estate knowledge than most. Wall Street attorney. Top Manhattan broker. Years of experience. And she still didn't know the STR formula. What changed in two and a half years is the kind of thing that makes you mad you didn't start sooner. We break down: How a garage converted to a game room unlocked $50K in annual revenue she didn't know she was leaving on the table Why her Hamptons properties 2.5X'd in revenue in under two years, going from $100K to $266K on property one alone The $220K tax savings she generated from a single December purchase using cost segregation and bonus depreciation Why high land value markets like the Hamptons are actually less efficient for tax savings, and where to buy instead How bonus depreciation being made permanent changes the entire strategy for W2 earners with growing incomes The 100-hour rule, why mandatory property manager communities kill your tax benefits, and what to look for before you buy The bottom line: if a former Wall Street real estate attorney needed this formula to make her properties actually work, you probably do too. 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 3

    100% Bonus Depreciation Is Back Permanently (And Most High-Income Professionals Still Don't Know It)

    For years, high-income professionals watched the STR tax loophole phase out and assumed it was gone for good. It's not. And the window to act is open right now. In this episode, I sit down with Ryan Bakke, CPA and founder of Tax Strategy 365, to break down everything you need to know about the return of 100% bonus depreciation, how to use it correctly, and how to make sure you never have to sweat an IRS audit. Ryan left Deloitte to build one of the most successful CPA firms in the country, now approaching eight figures in revenue with 60 employees. He has helped hundreds of high-income professionals use the STR tax loophole to legally offset their W2 income and build real, lasting wealth outside of their careers. If you are a doctor, surgeon, or high-income professional wondering whether this strategy is still valid and whether it is right for you, this episode is required listening. We break down: Why 100% bonus depreciation is now permanent under the One Big Beautiful Bill, and what that means for short-term rental investors going forward The exact tax code carve-out (Section 469) that makes the STR loophole legal, and why less than 300 characters in the tax code changed everything Why holding your STR long-term is not optional, and what depreciation recapture will cost you if you sell too soon The biggest documentation mistakes investors make that get them destroyed in an audit, and the log strategy that protects you What the IRS actually asks in an audit interview and why your story matters as much as your numbers Why the 30-year fixed mortgage is the single greatest wealth-building tool available to Americans, and why most high-income professionals are ignoring it The bottom line: The strategy is legal, it is permanent, and the investors who understand it are building generational wealth while their peers are handing half their income to the government. 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 3

    REPS vs. the STR Tax Loophole: The $25,000 Mistake We Made (And How to Avoid It)

    Most W2 earners think REPS and the STR tax loophole are the same thing. They are not, and confusing the two could be costing you tens of thousands of dollars a year. In this episode, Michael and Liz break down the real difference between real estate professional status and the STR tax loophole, why one is nearly impossible for full-time employees, and how the 100-hour rule opens the door for W2 couples who want to build wealth without quitting their jobs. We break down: The core difference between REPS and the STR tax loophole, and why one does not lead to the other Why getting your real estate license does not qualify you for REPS (and the misconception that trips up almost everyone) The 750-hour requirement for REPS and why it is virtually impossible if you hold a full-time job The three requirements to qualify for the STR tax loophole, including the 7-day rule and material participation The $25,000 tax mistake we made with the wrong CPA, and how to find a thought partner instead of just a tax filer Why stay-at-home parents are uniquely positioned to satisfy the 100-hour rule and help their family build generational wealth The bottom line: you do not need 750 hours, a real estate license, or a $1,000-an-hour tax lawyer. You need the right strategy, 100 hours, and personal ownership of your 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/

See All (100)

5
out of 5
71 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
    100
  • Rating
    Explicit
  • Copyright
    © 2026 STR Like The Best
  • Show Website
    STR Like The Best

You Might Also Like