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Total monthly reach
Estimated from 1 chart position in 1 market.
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- 🇺🇸US · Entrepreneurship#1525K to 30K
- Per-Episode Audience
Est. listeners per new episode within ~30 days
2.5K to 15K🎙 ~2x weekly·84 episodes·Last published 5d ago - Monthly Reach
Unique listeners across all episodes (30 days)
5K to 30K🇺🇸100% - Active Followers
Loyal subscribers who consistently listen
2K to 12K
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On the show
Recent episodes
There Is No Perfect Time to Buy (And Why Waiting Is the Most Expensive Mistake STR Investors Make)
Jun 19, 2026
16m 38s
The Real Cost of Doing Your STR Journey Alone (And the 4 Phases Where Most Investors Get It Wrong)
Jun 12, 2026
31m 56s
From $180K Tax Bill to $110K Refund: What 9 Months in the Program Actually Looks Like
May 29, 2026
47m 44s
The Fear of Out-of-State Investing Is Costing You Six Figures in Tax Savings Every Year
May 22, 2026
25m 35s
From Screwdrivers to Systems: Launching Property #8 (Lessons From Property #1)
May 15, 2026
22m 42s
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| Date | Episode | Description | Length | ||||||
|---|---|---|---|---|---|---|---|---|---|
| 6/19/26 | 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... | 16m 38s | ||||||
| 6/12/26 | 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 on... | 31m 56s | ||||||
| 5/29/26 | 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... | 47m 44s | ||||||
| 5/22/26 | 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 ... | 25m 35s | ||||||
| 5/15/26 | 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... | 22m 42s | ||||||
| 5/8/26 | 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... | 42m 38s | ||||||
| 5/1/26 | 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... | 18m 56s | ||||||
| 4/24/26 | 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... | 21m 28s | ||||||
| 4/10/26 | 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... | 27m 04s | ||||||
| 4/3/26 | 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... | 21m 34s | ||||||
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| 4/3/26 | 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... | 26m 07s | ||||||
| 3/20/26 | 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-... | 21m 11s | ||||||
| 3/13/26 | 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 th... | 36m 11s | ||||||
| 3/6/26 | 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 ... | 36m 45s | ||||||
| 2/27/26 | 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... | 22m 55s | ||||||
| 2/20/26 | 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 conversati... | 39m 21s | ||||||
| 2/13/26 | 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 p... | 30m 13s | ||||||
| 1/16/26 | 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 i... | 39m 19s | ||||||
| 1/3/26 | 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 bo... | 20m 19s | ||||||
| 12/19/25 | 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 Airbnb is reading every message you send with AI to enforce policies, ... | 30m 17s | ||||||
| 12/12/25 | 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 mone... | 18m 06s | ||||||
| 12/5/25 | 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 chan... | 38m 03s | ||||||
| 11/28/25 | 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 three... | 41m 54s | ||||||
| 11/21/25 | Can You Really Trust That Revenue Projection? Inside How STR Data Actually Gets Made | LEARN HOW I ANALYZE IF A PROPERTY WILL WORK AS A STR 🔥 https://strlikethebest.com/strlitmustest?utm_source=pod You're about to wire $150K for a down payment based on a revenue projection. But three different platforms just gave you three different numbers. Which one is real? In this episode, Michael sits down with Jae Seok An, founder of AirBtics and former Meta software developer, to pull back the curtain on how short-term rental data actually gets built and more importantly, how to know if ... | 27m 39s | ||||||
| 11/8/25 | Why Meta & Goldman Employees Are Buying $1M+ Airbnbs (It's Not What You Think) | USE MY 5-STEP LITMUS TEST TO SEE THE PROFITABILITY OF A POTENTIAL PROPERTY: https://strlikethebest.com/litmuspod Q4 2025 Market Update: What's Actually Working Right Now Most people think high-income professionals are buying Airbnbs for cash flow. They're wrong. In this episode, Michael and Liz reveal the real reason why employees at Meta, Amazon, Blackstone, and Goldman Sachs are aggressively buying $750K-$1.5M short-term rental properties and it has everything to do with the tax code. We br... | 26m 39s | ||||||
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Chart Positions
1 placement across 1 market.
Chart Positions
1 placement across 1 market.