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.
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 investment banker at Citi and Merrill Lynch. He knows...
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. Today that property is worth over $2M and generating $8,750 to $11K per week. Her second, a gutted co...
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 over 10 years of STR investing.
They also share the full origin story...
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 highlight reel. It's the real story of...
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 law means for high-income investors right now.
Amanda and Matt are CPAs by day and real estate...
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-scenes conversation we've been meaning to have, covering 9 years of...
Finding the Right Property Is Just the First 10% (The Full Blueprint for a 90th Percentile STR)
Most STR investors spend months finding the perfect market and the perfect property. Then they buy something "turnkey," take their own photos, skip the specialist designer, and wonder why their numbers fall flat.
In this episode, Michael and Liz break down the complete framework for turning a good property into a 90th percentile short-term rental, from design and staging to photography and dynamic pricing.
This is not about buying better. It is about executing better once you own it. Michael and Liz share the exact mistakes they made early in their own portfolio, what they...
Stop Using AI as a Better Google (3 Ways It Actually Makes You Money in STR)
Most people using AI like a search engine are leaving serious money on the table. If you're typing one-off questions on a free plan and calling it a day, you're running one of the most powerful tools available at about 5% of its actual capacity.
In this episode, I sit down with Liz to break down exactly how we use AI across our 30+ property portfolio, from analyzing inspection reports before we close to solving guest issues without sending a repair person out at 11pm.
These are not theories. These are the exact systems we use every...
We Wasted Time on a Real Estate License (The 100-Hour Strategy for W-2 Couples)
Most high-income couples assume getting a real estate license is the shortcut to real estate tax benefits. We made that exact mistake in 2018, and it cost us years of going down the wrong path.
In this episode, I sit down with Liz to break down the real difference between Real Estate Professional Status and the STR tax loophole, and why one works for almost every W-2 couple and the other almost never does.
We recorded this one just the two of us because this question comes up constantly with our clients and we wanted to...
The Empty Nester Problem Nobody Talks About (Identity, Marriage, and $1.5M in Tax Savings)
Most couples don't realize the empty nester transition is three separate problems, not one. And most of them hit all three at the same time, completely unprepared.
In this episode, Liz and I sit down to break down what actually happens when the kids leave, why stay-at-home parents lose more than just a routine, and how short-term rental investing solves all three problems at once.
This isn't just a real estate episode. It's a life design episode. We share what we've learned from building an STR portfolio together, the hard conversations we had along the...
How Our 8 STRs Let Us Live in Taiwan for 7 Weeks (And Why the Money Was Never the Point)
Most people building passive income are chasing a number. We were chasing something else entirely.
In this episode, Michael and Liz sit down together from Taipei, Taiwan, where they're spending their third consecutive summer with their kids, to share the real reason they built their STR portfolio and what time freedom actually looks like in practice.
This isn't a theory episode. It's a behind-the-scenes look at how two former investment banking and fashion professionals designed a life where the portfolio works while they're sleeping, the kids are in $45 swim lessons four days a week, and...
How One STR Property Can Save $370K in Taxes (And Why We're Never Selling It)
Most investors think the endgame is to buy, hold, and eventually sell. But selling might be the most expensive decision you ever make.
In this episode, Michael and Liz share a real-time breakdown of their newest short-term rental, a $2.4M Tennessee property launched July 1st, covering the actual cash flow numbers, the tax strategy behind it, and why they plan to hold it for generations.
This is one of the most transparent, numbers-first episodes we've done. No hypotheticals. Just the real performance data, the cost segregation results, and the Section 1014 strategy that changes how you...
The Skill Corporate America Punishes That Real Estate Rewards
Corporate America trained you to be guarded, competitive, and quiet. That mindset will keep you stuck in real estate.
In this episode, I sit down with my co-founder and wife, Liz, to talk about the single biggest unlock in our investing journey and why we built everything we have around it.
This is not a guest episode. It is one of the most honest conversations we have had on the podcast. We break down exactly how community has shaped every deal, every breakthrough, and every key hire in our business, from our first property to...
Productivity Isn't About Doing More (It's About What You Stop Doing)
Most people think being productive means doing more, working faster, or squeezing in one more task. That's not how we do it.
In this episode, I sit down with Liz to break down the exact system behind running two businesses, growing to 113,000 social media followers, and raising two kids under 5 at the same time.
This isn't theory. These are the exact hires we made, the things we stopped doing, and the mindset shifts that made all of it possible.
We break down:
Why productivity is a subtraction game, not an...
$220K in Taxes Saved From One Purchase (The STR Formula Even Real Estate Attorneys Miss)
Most people think owning Hamptons real estate means success. Ann Marie Folan had two properties there and was still throwing cash at them every month just to keep the lights on.
In this episode, I sit down with Ann Marie Folan, former Wall Street real estate attorney and one of Manhattan's most prominent brokers, to break down how she went from bleeding cash on two Hamptons properties to running a 5-property portfolio on track for over $800K this year.
Ann Marie came in with more real estate knowledge than most. Wall Street attorney. Top Manhattan...
REPS vs. the STR Tax Loophole: The $25,000 Mistake We Made (And How to Avoid It)
Most W2 earners think REPS and the STR tax loophole are the same thing. They are not, and confusing the two could be costing you tens of thousands of dollars a year.
In this episode, Michael and Liz break down the real difference between real estate professional status and the STR tax loophole, why one is nearly impossible for full-time employees, and how the 100-hour rule opens the door for W2 couples who want to build wealth without quitting their jobs.
We break down:
The core difference between REPS and the STR...
100% Bonus Depreciation Is Back Permanently (And Most High-Income Professionals Still Don't Know It)
For years, high-income professionals watched the STR tax loophole phase out and assumed it was gone for good. It's not. And the window to act is open right now.
In this episode, I sit down with Ryan Bakke, CPA and founder of Tax Strategy 365, to break down everything you need to know about the return of 100% bonus depreciation, how to use it correctly, and how to make sure you never have to sweat an IRS audit.
Ryan left Deloitte to build one of the most successful CPA firms in the country, now approaching eight figures...
There Is No Perfect Time to Buy (And Why Waiting Is the Most Expensive Mistake STR Investors Make)
You've done the research. You've looked at the markets. You've run the numbers. So why haven't you bought yet?
In this episode, Michael and Liz break down the most common trap STR investors fall into: waiting for the perfect moment that never comes, and the real cost of staying on the sidelines.
We cover a lot of ground here, from how to train your eye to spot an outlier property, to the mindset shift that separates investors who build wealth from those who stay stuck in the research loop.
We break down:
<...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 down the real price of doing it alone across every phase of the STR investment journey, from finding the right market all the way to managing revenue once you go live.
We have been running short-term rentals since 2016, built a portfolio of 30+ properties generating $2.3M a year, and made every one of these mistakes ourselves before we figured it out. This...
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 Like
Most 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 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 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...
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 July 4th.
We break down:
<...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 right moment, and using social media as leverage in a...
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 Michael's belief in Liz on a subway ride...
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 ever, and how being a married couple investing together is one...
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 Michael and Liz are doing in real time, with two young kids, multiple...
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 not a conversation about babysitting and diapers. It is about identity, wealth building, and...
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 don't even know exists.
We break down:
<...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-page book on the subject, and used that same time to buy...
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, 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...
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 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...
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 See
Most 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...
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, CEO of Beyond Pricing, to break down why revenue management is the most overlooked lever in your STR portfolio and what the top operators are doing differently.
Julie has been leading Beyond for almost six years, and the data her team sits on is unlike anything else in the industry. This conversation will change how you think about pricing...
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 the one thing that actually accelerated their journey from a few properties to a 30+ unit portfolio: community.
They share how a corporate "zero-sum" mindset kept them isolated early on, and what changed when they started asking for help, showing up at conferences, and surrounding themselves with people a few steps ahead. This isn't a fluffy conversation about networking. It's a real...
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 Cohen, who's acquired $600 million in multifamily real estate over 15 years, to talk about something every investor needs to understand: knowing when to walk away.
In 2022, Eli stopped buying. Not because he ran out of capital. Because the returns didn't justify the risk anymore. This conversation is about market timing, discipline, and deal selection principles that apply whether you're buying your first Airbnb or your tenth apartment building.
<...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 story behind STR Like The Best, the core values that drive everything they do, and why they've helped hundreds of high-income professionals build STR portfolios from scratch.
We break down:
The $10K/month origin story. How one apartment in Queens making $5,000/month in cashflow while they were both working in...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 Michael uses in his own STR business), to break down how AI is fundamentally changing short-term rental operations and why hosts who don't adapt will get left behind by operators who are 10x more efficient.
We break down:
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 for disaster.
Except it's not.
In this episode, Michael and Liz pull back the curtain on how they actually make it work. Not the Instagram highlight reel. The real stuff. The 2:30 AM wake-ups, the fights they avoided by hiring smart, the one rule that's saved their marriage, and why making more money solved more problems than therapy ever could.
We...
Why Most Hosts Are Slaves to Their Airbnb (And How to Break Free) w/ Shaun Shirazian from Lodgify
If you're only on Airbnb, you don't have a business. You're a vendor to Airbnb. And if they change the algorithm, spike their fees, or suspend your account over a bad review, your entire income disappears overnight.
In this episode, Michael sits down with Shaun Shirazian, CEO of Lodgify, to break down why property management systems are non-negotiable for anyone serious about STR investing, how the right tech stack creates three types of independence, and why AI is about to fundamentally change how small operators compete.
We break down:
The three types...What Your CPA Gets Wrong About The STR Tax Loophole w/ Amanda Han & Matt MacFarland from Keystone CPA
Your CPA says you make too much money. They say you work too many hours at your job. They say you need to be a real estate professional. All three of those statements are wrong.
In this episode, Michael sits down with Amanda Han and Matt MacFarland from Keystone CPA, two of the leading tax experts in the short-term rental space, to break down exactly how the STR tax loophole works, why most CPAs get it wrong, and how to protect yourself if the IRS ever comes knocking.
We break down:
The...