Podcast
STR Like The Best
Hosted by Michael Chang · EN
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.
38episodes
Episodes
Newest firstAll episodes
From Shoe Reseller to Real Estate Developer: How Rajan Chida Built Royal Oak Retreats at 23
May 800:42:38Tap to summarizeMost 23-year-olds are figuring out their first job. Rajan Chida was turning down JP Morgan to build luxury cabins in Virginia.In this episode, I sit down with Rajan Chida, co-founder of Royal Oak Retreats, to talk about how he went from reselling shoes on eBay in college to developing ground-up luxury STR cabins and building a 550K social media following in under a year.Rajan's story is not your typical real estate success story. It's about stacking capital early, betting on yourself at the right moment, and using social media as leverage in a way that most developers with 10 years of experience still don't understand.We break down:How Rajan funded his first real estate project with shoe reselling money he saved from age 17, and why starting a "job" at 17 gave him a head start most investors don't get until their mid-twentiesWhy his 550K following didn't convert to bookings the way he expected, and the pivot to female travel influencers that finally got Royal Oak Retreats fully bookedThe permitting nightmare in Warren County, Virginia that nearly derailed the entire project, including a disgruntled neighbor, a six-page complaint full of false claims, and a road he had to build just to get the permit approvedHow tariffs forced him to resource his signature window walls from Poland, adding three months of delays and zero construction progressWhy he turned down his JP Morgan offer two weeks before his start date, and the conversation with his dad that gave him the confidence to make that callThe pre-deposit playbook he's using for cabins two and three, including $50 deposits, VIP early access, and how Travis at Outpost X raised $1M before breaking groundThe bottom line: social media is not just a marketing tool. In the hands of the right person, it replaces the track record, the connections, and the credibility that used to take a decade to build.LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack 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/
Transcribe →The Real Foundation of Our STR Business (It Has Nothing to Do With Real Estate)
May 100:18:56Tap to summarizeMost people think building a successful STR portfolio comes down to markets, numbers, and design. They're missing the one thing that actually makes or breaks everything.In this episode, I sit down with Liz to talk about what has quietly powered every risk we've ever taken, every property we've bought, and every hard moment we've fought through together over the last 10 years.This isn't a real estate tactics episode. It's the one we probably should have recorded sooner.We break down:How Michael's belief in Liz on a subway ride in 2017 led her to quitting her job and going all in on STRWhy mutual belief between spouses is a superpower most people completely overlookThe moment I lost confidence in myself and what Liz said that brought it backWhat our "Corona Battle Plan V2" spreadsheet reminded us about working through the hardest seasons togetherWhy cutting your spouse down to keep them close is one of the most poisonous things you can do in a relationshipHow we divided responsibilities across a 30+ property portfolio so we each lead where we're strongestThe bottom line: If you know your spouse has your back no matter what, you will take bigger risks, make better decisions, and build something neither of you could have built alone.LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack 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/
Transcribe →The Market Is Uncertain. Your Tax Bill Isn't. Why We're Buying Property Number Eight Now.
Apr 2400:21:28Tap to summarizeThere's always a reason not to buy. In 2020 it was COVID. In 2022 it was rising rates. Today it's tariffs, gas prices, and AI uncertainty. The investors who waited are still waiting.In this episode, I sit down with Liz to walk through exactly why we're closing on our eighth short-term rental, a $2.1M property, despite everything happening in the headlines right now.We're not ignoring the noise. We're explaining how we filter it, why the STR tax loophole makes buying now more compelling than ever, and how being a married couple investing together is one of the most underrated advantages in real estate.We break down:Why there's always a reason not to buy, and why waiting has cost investors more than any recessionThe exact data process Liz uses to find underserved markets and identify the right propertyHow the 100-hour rule works as a married couple and why your combined hours are more powerful than you thinkWhy we pushed closing back 10 days on this deal and what the due diligence process actually looks likeThe basis step-up strategy we're using to pass this portfolio to our kids tax-freeWhy the One Big Beautiful Bill has made STR assets more valuable than they were a year agoThe bottom line: uncertainty is permanent. Your tax bill is optional.LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack 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/
Transcribe →Why Married Couples Have an Unfair Tax Advantage (And Exactly How We Use It)
Apr 1000:27:04Tap to summarizeMost married couples filing jointly have no idea they are sitting on one of the most powerful tax advantages in the entire tax code.In this episode, Michael sits down with co-host Liz to break down exactly how married couples can use the 100-hour material participation rule to qualify for the short-term rental tax loophole, and how they are using it right now across 7 properties with a $2.1 million deal currently in contract.This is not a theoretical conversation. This is exactly what Michael and Liz are doing in real time, with two young kids, multiple properties, and a six-figure tax liability on the line.We break down:What the short-term rental tax loophole actually is and how it allows you to offset W2 income, 1099 income, and capital gains with paper losses from depreciationWhy married couples can combine their hours and how that means one spouse doing 10 hours and the other doing 10 hours counts as 20 hours from a material participation perspectiveThe exact hours Liz has logged in the last 16 days since going under contract on their $2.1 million Tennessee property, including design work, vendor coordination, and mood board creationWhat Michael's day one plan looks like and how he is managing insurance, loans, cleaners, and an operational team before they even close on April 16thHow the post-close launch phase is the easiest way to knock out your hours and why a week on the ground at your property can get you to 100 hours faster than you thinkWhy 100% bonus depreciation is back as of July 2025 and what that means for high-income couples who are ready to stop paying six figures in taxes every single yearThe bottom line: being married is not just a life decision. With the right strategy, it is one of the most powerful tax advantages available to working professionals in America today.LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack 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/
Transcribe →Why Being a Stay-at-Home Parent Is the Most Underrated Tax Strategy for High-Income Couples
Apr 300:21:34Tap to summarizeWhy Being a Stay-at-Home Parent Is the Most Underrated Tax Strategy for High-Income CouplesMost 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 fortuneHow one spouse staying home creates the perfect material participation setup for the short-term rental tax loophole, even if the other spouse earns seven figuresThe identity guilt that stops smart, driven people from walking away from their careers and how STRs let you keep bothWhy a tax refund is not free money and what to actually look at on your return to understand your real tax burdenHow to hire your kids into the business to compound family wealth and reduce taxes even furtherEstate planning as the next frontier for STR investors who are building a legacy, not just a portfolioThe 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.comLEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack 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/
Transcribe →The Real Reason We Know Which STR Markets Work (It's Not What You Think)
Apr 300:26:07Tap to summarizeMost 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 pictureThe 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 opportunityWhy 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 marketHow 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 guessworkThe 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 marketsWhy 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 STRThe 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.comLEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack 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/
Transcribe →The STR Financing Blueprint: When to Use DSCR Loans, Second Home Loans, and Everything in Between
Mar 2000:21:11Tap to summarizeMost 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-2The second home loan trap most new investors fall into, and why the 180-day occupancy rule makes it nearly impossible to cash flowWhy the 5 to 50 property range is the sweet spot for DSCR loans, and when conventional financing still makes more senseHow DSCR loans work with LLCs, partnerships, and trusts, and why serious investors structure it this way from the startThe connection between DSCR loans and the STR tax loophole, and how using both together lets you keep scaling without your tax returns slowing you downWhat Robin learned buying three STRs himself, including the paperwork reality that conventional lenders put high earners throughThe 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/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack 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/
Transcribe →I Used to Think STR Design Was an Expense. Now Every Property We Own Is Professionally Designed
Mar 1300:36:11Tap to summarizeYou 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 dollarThe data and comp analysis Somerled uses to forecast revenue and build the right design budget for any marketWhy generic design is a losing strategy in 2026 and what "niching down" actually looks like in practiceThe amenity stacking strategy that creates hero shots, drives bookings, and separates top 10% properties from everyone elseWhy relying on Airbnb alone to sell your property is no longer enough and what a real marketing strategy looks likeThe "astrology cabin" case study: how Bri branded a 3-bedroom cabin around a theme guests didn't know they wanted until they saw itThe 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/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack 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/
Transcribe →How a 22-Year-Old Built 70 Units From Scratch (And Why Arbitrage Is Just the Beginning)
Mar 600:36:45Tap to summarizeMost 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 nextThe exact tech stack running her remote portfolio, including HostAway, PriceLabs, TrueV, Bestie AI, Kendo AI, and Phantom AIWhy she uses 9 VAs to run 70 units remotely and how she structured 24/7 coverage without burning out her teamHow AI is training her customer service and cold calling teams in real time, and why she says it improves humans rather than replacing themThe one habit every operator should start now: recording everything, because your future AI tools will need that dataWhy her tax bill was the wake-up call that's pushing her from arbitrage into ownership, and what bonus depreciation changes everythingThe 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/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack 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/
Transcribe →What 19 STR Properties Taught Me About Finding Deals Nobody Else Can See
Feb 2700:22:55Tap to summarizeWhat 19 STR Properties Taught Me About Finding Deals Nobody Else Can SeeMost 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 secondsThe 50-comp framework BNBCalc uses to show you exactly where your property stacks up against the competitionWhy defensibility is the most overlooked factor when buying an STR and the costly Florida mistake that proved itHow to reverse engineer what top operators are doing to find markets and properties with a real edgeWhy the STR tax loophole is only powerful if you buy the right property and hold it for the long termWhat the new BNBCalc markets tool does and why it changes how investors identify opportunities before anyone elseThe 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/wealthpodApply to work with Michael: https://strlikethebest.com/applypodFollow Michael on Instagram: https://www.instagram.com/michaelchangbnbTrack 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/
Transcribe →