STR Like The Best

Michael Chang
  • 5.0 (67)
  • 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

    Why Being a Stay-at-Home Parent Is the Most Underrated Tax Strategy for High-Income Couples

    Why Being a Stay-at-Home Parent Is the Most Underrated Tax Strategy for High-Income Couples Most high-income couples think staying home means giving up financial contribution. They're wrong. In this episode, Michael sits down with co-host Liz to break down why being a stay-at-home parent is one of the most powerful tax strategies available to high-income couples, and how they have used it to save six figures in taxes while building a 30-property portfolio generating $2.3M per year. This is not a conversation about babysitting and diapers. It is about identity, wealth building, and a tax strategy most CPAs never explain correctly. We break down: The 100-hour rule vs. the 750-hour REP requirement and why most people confuse the two, and why that confusion costs them a fortune How one spouse staying home creates the perfect material participation setup for the short-term rental tax loophole, even if the other spouse earns seven figures The identity guilt that stops smart, driven people from walking away from their careers and how STRs let you keep both Why a tax refund is not free money and what to actually look at on your return to understand your real tax burden How to hire your kids into the business to compound family wealth and reduce taxes even further Estate planning as the next frontier for STR investors who are building a legacy, not just a portfolio The bottom line: the stay-at-home parent is not the one sacrificing for the family. With the right strategy, they are the one saving it the most money. 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 www.thestrtaxloophole.com 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

    22 min

  2. APR 3

    The Real Reason We Know Which STR Markets Work (It's Not What You Think)

    Most investors open AirDNA, look at the numbers, and think they've done their research. They haven't. In this episode, I sit down with my co-host and wife Elizabeth to pull back the curtain on the exact process we use to evaluate STR markets for our clients and ourselves. We've been doing this for 10 years. We've survived the pre-COVID boom, the COVID collapse, and the post-COVID correction. And in that time, we've built a network, a process, and a level of market depth that most investors don't even know exists. We break down: Why AirDNA is a great starting point but will mislead you if you stop there, and how we layer in agent intel, property manager data, and on-the-ground conversations to get the full picture The exact questions Liz asks every broker and property manager before recommending a single market to a client, including regulation landscape, price range fit, and occupancy opportunity Why market selection is the one thing you can't get wrong, and how we've seen first-time investors struggle not because they operated poorly, but because they started in the wrong market How Liz has analyzed close to 200 properties in just the first two months of 2025, and why that repetition is what separates real market knowledge from guesswork The matching process we use to pair high-income clients with the right market for their budget, timeline, and risk tolerance, from $750K inland properties to $1.5M+ beach markets Why the work doesn't stop once you find a property, and what it actually takes to go from closing to a fully optimized, revenue-generating STR The bottom line: anyone can look at data. Very few people know how to read it, layer it, and act on it. That's the difference between guessing and knowing. 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 www.thestrtaxloophole.com 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

    26 min

  3. MAR 20

    The STR Financing Blueprint: When to Use DSCR Loans, Second Home Loans, and Everything in Between

    Most STR investors hit a wall around property 3 or 4. Not because they run out of deals, but because conventional lenders start stacking paperwork, haircuts, and restrictions that make it nearly impossible to keep moving. In this episode, I sit down with Robin Simon, author of The Book on DSCR Loans, to break down every financing option available to short-term rental investors and exactly when to use each one. Robin spent years inside the DSCR lending industry, took a year off to write a 715-page book on the subject, and used that same time to buy three STRs himself using the strategies he teaches. This is the conversation I wish I had before I started scaling. We break down: What DSCR loans actually are and how they're different from conventional financing, including why they look at the property instead of your W-2 The second home loan trap most new investors fall into, and why the 180-day occupancy rule makes it nearly impossible to cash flow Why the 5 to 50 property range is the sweet spot for DSCR loans, and when conventional financing still makes more sense How DSCR loans work with LLCs, partnerships, and trusts, and why serious investors structure it this way from the start The connection between DSCR loans and the STR tax loophole, and how using both together lets you keep scaling without your tax returns slowing you down What Robin learned buying three STRs himself, including the paperwork reality that conventional lenders put high earners through The bottom line: the financing tool you choose determines how fast you can scale, and most high earners are using the wrong one. 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

    21 min

  4. MAR 13

    I Used to Think STR Design Was an Expense. Now Every Property We Own Is Professionally Designed

    You just spent $1M on a property. Now someone is telling you to spend another $200K on design. That fear is real, and it stopped me too. In this episode, I sit down with Jordan McDonough and Bri West, co-founders of Somerled Designs, the largest short-term rental focused design firm in the country, to break down why professional design is the highest-ROI decision you can make for your STR investment. Jordan and Bri have worked with hundreds of STR investors and manage over 35 properties of their own. What they've built at Somerled isn't just a design firm. It's a data-first strategy that tells you exactly what to build, who to build it for, and how to make sure it pays for itself. We break down: Why design is a revenue driver, not an expense, and how to calculate the ROI before you spend a dollar The data and comp analysis Somerled uses to forecast revenue and build the right design budget for any market Why generic design is a losing strategy in 2026 and what "niching down" actually looks like in practice The amenity stacking strategy that creates hero shots, drives bookings, and separates top 10% properties from everyone else Why relying on Airbnb alone to sell your property is no longer enough and what a real marketing strategy looks like The "astrology cabin" case study: how Bri branded a 3-bedroom cabin around a theme guests didn't know they wanted until they saw it The bottom line: the investors winning in this market aren't spending more. They're spending smarter, and design is where the smartest money goes first. 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

    36 min

  5. MAR 6

    How a 22-Year-Old Built 70 Units From Scratch (And Why Arbitrage Is Just the Beginning)

    Most people wait until they feel "ready" to build something real. Hailee Marie started at 19, during a pandemic, when everyone else was running the other way. In this episode, I sit down with Hailie Marie, short-term rental operator and angel investor, to talk about how she scaled a 70-unit remote arbitrage portfolio from scratch and why she's now using that cash flow to build long-term wealth. Hailie built something most operators never do: a business that runs without her. Nine VAs, a full tech stack, 24/7 coverage, and AI handling guest communications around the clock. She did it starting with three units in Austin at 19 years old. We break down: How Hailie scaled from 3 units to 70 using arbitrage as a tool, not a destination, and what she's building toward next The exact tech stack running her remote portfolio, including HostAway, PriceLabs, TrueV, Bestie AI, Kendo AI, and Phantom AI Why she uses 9 VAs to run 70 units remotely and how she structured 24/7 coverage without burning out her team How AI is training her customer service and cold calling teams in real time, and why she says it improves humans rather than replacing them The one habit every operator should start now: recording everything, because your future AI tools will need that data Why her tax bill was the wake-up call that's pushing her from arbitrage into ownership, and what bonus depreciation changes everything The bottom line: Arbitrage can make you cash flow. But the operators who win long-term are the ones using that cash flow to buy assets, build systems, and invest in things that compound. 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

    37 min

  6. FEB 27

    What 19 STR Properties Taught Me About Finding Deals Nobody Else Can See

    What 19 STR Properties Taught Me About Finding Deals Nobody Else Can See Most STR investors buy based on what their realtor tells them, what a random listing looks like, or what their gut says. And then they wonder why the numbers never hit the projection. In this episode, I sit down with Jeremy Werden, co-founder of BNBCalc, to break down how data-driven underwriting separates the investors who build real wealth from the ones who just get lucky once. Jeremy started with a $5,600 pontoon boat at 23 years old with no credit and no cash. Today he operates 19 STR listings across multiple states and built one of the most widely used underwriting tools in the industry. This conversation is packed with the kind of hard-won insight you only get from someone who has actually done it at scale. We break down: Why your realtor's projections are almost always wrong and what to use instead to underwrite a property in 25 seconds The 50-comp framework BNBCalc uses to show you exactly where your property stacks up against the competition Why defensibility is the most overlooked factor when buying an STR and the costly Florida mistake that proved it How to reverse engineer what top operators are doing to find markets and properties with a real edge Why the STR tax loophole is only powerful if you buy the right property and hold it for the long term What the new BNBCalc markets tool does and why it changes how investors identify opportunities before anyone else The bottom line: the investors winning right now are not smarter than you. They just have better data and they know how to use 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

    23 min

  7. FEB 20

    Your $600K Investment Deserves Better Than a Spreadsheet and a Gut Feeling

    You bought a great property. You amenitized it. You listed it. And then you priced it with your emotions and left thousands of dollars on the table. In this episode, I sit down with Julie Brinkman, CEO of Beyond Pricing, to break down why revenue management is the most overlooked lever in your STR portfolio and what the top operators are doing differently. Julie has been leading Beyond for almost six years, and the data her team sits on is unlike anything else in the industry. This conversation will change how you think about pricing forever. We break down: Why 55% of STR hosts are using Airbnb smart pricing or nothing at all, and why that's quietly destroying their returns The 15 factors Beyond analyzes for every single night of your calendar, and why a spreadsheet can never compete How Beyond uses guest intent data to see demand shifts before they show up in the market Why the booking window collapsed in 2025 and what that means for how you price your calendar right now Why last minute discounting is training your guests to wait you out, and what to do instead What private equity consolidation in the STR space means for independent operators in 2026 The bottom line: your property is a six-figure asset. It deserves a revenue management system that treats it like one. 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

  8. FEB 13

    You're Smart Enough to Figure This Out Alone. That's Exactly Why You're Stuck.

    You've built a successful career by outworking and outthinking everyone around you. So why does building wealth outside your W2 feel so hard? In this episode, Michael and Liz sit down to talk about the one thing that actually accelerated their journey from a few properties to a 30+ unit portfolio: community. They share how a corporate "zero-sum" mindset kept them isolated early on, and what changed when they started asking for help, showing up at conferences, and surrounding themselves with people a few steps ahead. This isn't a fluffy conversation about networking. It's a real look at how one introduction, one conversation, or one piece of advice from the right person can unlock years of progress. We break down: How meeting one person at a conference in 2016 led to virtual assistants, better systems, and eventually the entire STR Like The Best education business The mindset shift from "figure it out alone" to building a network that compounds over time Why high earners often struggle to ask for help and how cultural and personality factors play into it What their mentorship community actually looks like with 150+ investors, 20 team members, and resources at every stage from search to operations The give-and-take dynamic that attracts the right people and filters out the ones who only take Why trying to do this solo is like playing on "super hard mode" and what to do instead The bottom line: The fastest path to building wealth isn't figuring it out alone. It's finding the right people who've already done it and learning from them. 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

    30 min
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5
out of 5
67 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
    83
  • Rating
    Clean
  • Copyright
    © 2026 STR Like The Best
  • Show Website
    STR Like The Best

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