STR Like The Best
Michael Chang
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About This Podcast
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.
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Recent Episodes
The Real Cost of Doing Your STR Journey Alone (And the 4 Phases Where Most Investors Get It Wrong)
Most high-income professionals think they can figure out short-term rental investing on their own. The cost of that assumption is higher than you think.In this episode, I sit down with Liz to break…
From $180K Tax Bill to $110K Refund: What 9 Months in the Program Actually Looks Like
From $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…
The Fear of Out-of-State Investing Is Costing You Six Figures in Tax Savings Every Year
You 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…
From Screwdrivers to Systems: Launching Property #8 (Lessons From Property #1)
We 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…
From Shoe Reseller to Real Estate Developer: How Rajan Chida Built Royal Oak Retreats at 23
Most 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…
The Real Foundation of Our STR Business (It Has Nothing to Do With Real Estate)
Most 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…
The Market Is Uncertain. Your Tax Bill Isn't. Why We're Buying Property Number Eight Now.
There'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,…
Why Married Couples Have an Unfair Tax Advantage (And Exactly How We Use It)
Most 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…
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 CouplesMost high-income couples think staying home means giving up financial contribution. They're wrong.In this…
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…
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…
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,…
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…
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 SeeMost STR investors buy based on what their realtor tells them, what a random listing looks like, or what their gut says. And…
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,…
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…
When to Walk Away From Your Best Asset (A $600M Real Estate Lesson)
Usually we focus on short-term rental investing, tax strategy, and how high-income professionals can offset W2 income through STRs. Today's different. Michael sits down with his college friend Eli…
Why We Started STR Like The Best (And Why We're Teaching You Everything We Know)
Most people ask us: "Why would you teach this? Why not just keep it to yourself and do more deals?"Fair question.In this episode, Michael and Liz sit down to answer that question and share the real…
How AI Automates 90% of My Guest Messages (And Why Hosts Who Don't Adapt Will Get Left Behind)
If you're manually responding to guest messages at 11pm, you're competing with one hand tied behind your back.In this episode, Michael sits down with Annie, co-founder of HelloHost (the AI platform…
How We Manage 30+ Short-Term Rentals, 2 Kids Under 5, and Actually Like Each Other
Most couples can't work together without wanting to kill each other. Add two kids under five, 30+ properties across multiple states, and a seven-figure business to the mix, and you've got a recipe…
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STR Like The Best has published 91 episodes since March 2023, covering topics in Business, Courses.
STR Like The Best is currently highly active with new episodes weekly. Average episode length is 37m.
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