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by Michael Chang
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- 3 days ago22 min
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 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 Jul...
- 1 weeks ago42 min
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 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...
- 2 weeks ago18 min
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 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 Mi...
- 3 weeks ago21 min
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, 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...
- Apr 10, 202627 min
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 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 Micha...
- Apr 3, 202621 min
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 no...
- Apr 3, 202626 min
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 do...
- Mar 20, 202621 min
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-...
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About STR Like The Best
Conversations with the best short term rental investors and business leaders in the world. We explore their ideas, methods, and stories to help you better invest your time and money.
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