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.
31episodes
Episodes
Newest firstAll episodes
From $180K Tax Bill to $110K Refund: What 9 Months in the Program Actually Looks Like
1w ago00:47:44Tap to summarizeFrom $180K Tax Bill to $110K Refund: What 9 Months in the Program Actually Looks LikeMost high-income couples know they're overpaying on taxes. Very few actually do something about it.In this episode, Michael sits down with Ashish and Smita, a Bay Area dentist and finance professional, to walk through their first 9 months in the STR Like The Best program, from their first property in Colorado to filing the most satisfying tax return of their lives.This isn't a highlight reel. It's the real story, including the self-doubt, the market search, the launch, the guests who left the hot tub uncovered, and the moment their CPA told them to expect a very large refund.We break down:How a $180K tax bill during Ashish's nose surgery recovery sent them down a rabbit hole that changed everythingWhy they chose Colorado over Hawaii, and how the mentorship helped them stop overthinking market selection and just moveWhat their first season actually looked like, covering the mortgage in off-peak months and heading into their best month everHow they got $94K back in federal taxes and $16K from California in their very first year with one propertyWhy "done for you" STR programs legally cannot qualify you for the tax benefits, and what the IRS actually requiresThe 4 things Ashish and Smita would tell their pre-July 2024 selves if they were still on the fenceThe bottom line: the STR tax loophole is real, it works, and it works best when you stop waiting for the perfect moment and just do the work.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 Fear of Out-of-State Investing Is Costing You Six Figures in Tax Savings Every Year
2w ago00:25:35Tap to summarizeYou live in California. Or New York. Or any other high-cost, high-tax state where buying a short-term rental locally makes zero financial sense. So you do nothing. And every year you wait, you leave six figures in tax savings on the table.In this episode, Michael and Liz break down exactly how they built a 30+ property STR portfolio worth $2.3M in annual revenue while managing everything remotely from New York City, and why out-of-state investing is not only possible, it's the smartest move high-income W2 earners can make right now.This is not a guest episode. This is 25 minutes of hard-won experience from two people who have done it, coached 30-40 California-based clients through it, and figured out every obstacle along the way.We break down:The mindset shift that unlocks everything, because if you believe you can't manage a property 2,000 miles away, you never will, and why that belief is costing you more than you thinkThe exact tech stack for remote management including smart locks, automated guest codes, $30 cameras from Amazon, noise monitors, and smart thermostats that let you run a property entirely from your phoneHow to hit your 100-hour material participation requirement while investing out of state, including the desktop work, vendor calls, guest communication, and setup coordination that count toward your hoursThe stay-at-home spouse advantage and why a married couple where one partner stays home is one of the most powerful setups for the STR tax loopholeHow to document your hours the right way, using smart lock entry codes per cleaner, camera logs, and access records that hold up if the IRS ever comes knockingWhy "we'll do everything for you" STR programs are a tax trap, and what actually happens three to four years later when the audit letter arrives and those people are long goneThe bottom line: The technology exists, the communities exist, and the strategy works. The only thing standing between you and six figures in annual tax savings is the belief that you have to live near your property to own 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 →From Screwdrivers to Systems: Launching Property #8 (Lessons From Property #1)
3w ago00:22:42Tap to summarizeWe closed on property #8 last week. And the difference between then and now is not even close.In this episode, I sit down with Liz to walk through what the first week post-closing actually looks like on our eighth Tennessee cabin, and contrast it against the chaos of doing it all ourselves for the very first time back in 2020.This is not theory. This is what we are doing right now, in real time, to hit the 100-hour material participation requirement and get this property launched before July 4th.We break down:Why Liz is logging 4 hours a day remotely and what that work actually looks like, from coordinating electricians for the hot tub and sauna to vetting pest control, bear-proof trash cans, and fire safety vendorsHow we accumulated 40+ hours in the first week alone, and why that number matters for unlocking the STR tax loophole on our active W-2 incomeThe vendor vetting mistake first-time investors make on Facebook, and why a comment section full of five-star reviews does not mean what you think it doesWhat our Day One plan looks like now versus property #1, when we drove down from New York with a car packed to the gills and a screwdriver we did not know how to useHow the material participation hours stack as you scale, and why hitting 100 hours gets easier with every property you add to your portfolioWhy we use the STR Tax Loophole app to log and document every hour, so our records are organized, defensible, and ready if the IRS ever comes askingThe bottom line: the work does not get smaller as you scale. It gets smarter. And knowing exactly what to do, who to call, and how to log it is what separates investors who get the tax benefit from those who leave it on the table.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 →From Shoe Reseller to Real Estate Developer: How Rajan Chida Built Royal Oak Retreats at 23
4w ago00:42:38Tap 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/
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