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STR Like The Best: Daily Summaries Delivered
by Michael Chang
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.
Latest Episodes
The most recent episodes — sign up to get AI-powered summaries of each one.
- 4 days ago19 min
It’s Not Too Late for the STR Tax Loophole (Qualify Before Year End and Avoid the Revenue Trap)
It’s late in the year and you’re wondering if you missed your window. You didn’t. But there are three things you have to get right before December 31, and most investors don’t even know what they are. In this episode, Michael and Liz break down exactly what it takes to qualify for the STR tax loophole before year end, what to do if you can’t close in time, and the revenue mistake that sends most investors into analysis paralysis. Whether you’re rushing to get a property in service this year o...
- 1 weeks ago44 min
From Zero to $60K in Tax Savings at 26 (The Year-One STR Q&A With Mei and Ray)
Most people spend years thinking about buying their first investment property. Mei and Ray did it in 6 weeks, got married in the middle of it, and saved $60K in taxes in their first year. In this episode, I sit down with Mei and Ray, 26-year-old tech workers from New York City, to break down their entire first year as STR investors, from signing the paperwork to cash flowing $60-70K in just 5 months of operation. This is one of the most honest year-one breakdowns we have done on this show. No...
- 2 weeks ago21 min
Why I’m Still Buying STRs at 7.5% (And the Done-For-You Shortcut That Will Get You Audited)
Interest rates are climbing again. Most investors are frozen. And a wave of done-for-you services is promising to handle everything for you while you collect the tax benefit. Two problems with that picture. In this episode, Michael and Liz break down the real impact of rising interest rates on the STR market, why the asset class is more protected than most people think, and why the shortcut everyone is being sold right now is a direct path to an IRS audit. Michael spent 10 years as an investm...
- Oct 9, 202633 min
How She’s Getting Her Third Hamptons STR for Free (The Equity Strategy Nobody Talks About)
Most STR investors obsess over cash flow. Ann-Marie Folan is playing a completely different game, and it’s working. In this episode, Michael sits down with Ann-Marie Folan, Manhattan real estate broker at Douglas Elliman, to break down how she built a 3-property Hamptons STR portfolio by optimizing for equity instead of cash flow. Ann-Marie bought her first East Hampton property in 2015 for $944K through a 1031 exchange from a 15-unit Queens apartment building she was desperate to offload. To...
- Oct 2, 202630 min
Making More But Keeping Less (The 3-Part Wealth Framework High Earners Miss)
Most high earners are winning the income game and losing the wealth game. They make great money, hand half to the government, park the rest in a savings account that doesn't beat inflation, and wonder 10 years later why they don't have more to show for it. In this episode, Michael and Liz debrief their first-ever client conference, Architect Your Wealth, held in New York City with almost 100 clients flying in from across the country, and break down the exact wealth framework they've built ove...
- Sep 25, 202638 min
What 10 Years of STR Mistakes Bought Us (And Why We're Now Teaching You to Skip Them)
If you're earning good money and still handing a massive chunk of it to the IRS every April, there's a better way. We built it the hard way so you don't have to. In this episode, Michael sits down with his partner Liz to pull back the curtain on how they built STR Like The Best from zero followers in May 2023, why they finally launched their education programs, and what 10 years of trial and error actually taught them about building real wealth through short-term rentals. This isn't a highlig...
- Sep 18, 202641 min
What Your CPA Gets Wrong About the STR Tax Loophole (100% Bonus Depreciation Is Back)
Most high-income W-2 professionals are leaving six figures on the table every year because their accountant doesn't fully understand the short-term rental tax loophole. And with 100% bonus depreciation now back permanently, the stakes have never been higher. In this episode, I sit down with Amanda Han and Matt from Keystone CPA to give the most comprehensive breakdown of the STR tax loophole we've done on this show, covering material participation tests, audit defense, and what the new tax la...
- Sep 11, 202620 min
Why We Launched the Mentorship Program (And Why We're Sharing the Whole Playbook)
Most high earners are stuck paying 40% in taxes year after year, trading time for money, and wondering if there's actually another way. There is. We know because we lived the exact same story. In this episode, I sit down with my co-founder Liz to share the real origin story behind STR Like The Best, why we left investment banking and a fashion career to build a 30+ property portfolio, and what finally convinced us to start teaching everything we know. This isn't a pitch. It's the behind-the-s...
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About STR Like The Best
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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Frequently Asked Questions
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It's a free AI-powered email that summarizes new episodes of STR Like The Best as soon as they're published. You get the key takeaways, notable quotes, and links & mentions — all in a quick read.
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When a new episode drops, our AI transcribes and analyzes it, then generates a personalized summary tailored to your interests and profession. It's delivered to your inbox every morning.
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How often does STR Like The Best release new episodes?
STR Like The Best publishes weekly. Our AI generates a summary within hours of each new episode.
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STR Like The Best covers topics including Education, Business, Entrepreneurship, Investing, Courses. Our AI identifies the specific themes in each episode and highlights what matters most to you.
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