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Artwork for STR Like The Best

STR Like The Best

Michael Chang
Short-Term Rentals
Airbnb
Property Management
Real Estate
Revenue Management
Real Estate Investing
Real Estate Flipping
Real Estate Investment
Covid-19
Artificial Intelligence
Manhattan Real Estate
Entrepreneurship
Guest Experience
Experiential Hospitality
Property Management Software
Tax Code
Mint House
Virtual Assistants
Hostgpo
Besty Ai

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.

PublishesWeeklyEpisodes81Founded3 years ago
Number of ListenersCategories
BusinessEntrepreneurshipInvesting

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Artwork for STR Like The Best

Latest Episodes

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... more

YouTube

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 sho... more

YouTube

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 invest... more

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 proj... more

YouTube

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Recent Guests

Jordan McDonough
Co-founder and design lead at Summerlit Designs
Summerlit Designs
Episode: I Used to Think STR Design Was an Expense. Now Every Property We Own Is Professionally Designed
Hailee Marie
22-year-old short-term rental investor with 70 units
Episode: How a 22-Year-Old Built 70 Units From Scratch (And Why Arbitrage Is Just the Beginning)
Jeremy Werden
Co-founder of BNBCalc; short-term rental investor
BNBCalc
Episode: What 19 STR Properties Taught Me About Finding Deals Nobody Else Can See
Julie Brinkman
Guest, Beyond Pricing
Beyond Pricing
Episode: Your $600K Investment Deserves Better Than a Spreadsheet and a Gut Feeling
Eli Cohen
Investor and operator blending real estate with fast-food franchise ownership
C5 restaurants, Lane's Chicken Fingers, Fazoli's, Common Rojas
Episode: When to Walk Away From Your Best Asset (A $600M Real Estate Lesson)
Shaun Shirazian
CEO of Lodgify
Lodgify
Episode: Why Most Hosts Are Slaves to Their Airbnb (And How to Break Free) w/ Shaun Shirazian from Lodgify
Amanda Han
CPA, Keystone CPA, real estate investor
Keystone CPA
Episode: What Your CPA Gets Wrong About The STR Tax Loophole w/ Amanda Han & Matt MacFarland from Keystone CPA
Matt MacFarland
CPA, Keystone CPA, real estate investor
Keystone CPA
Episode: What Your CPA Gets Wrong About The STR Tax Loophole w/ Amanda Han & Matt MacFarland from Keystone CPA
Jae Seok An
Founder of AirBtics
AirBtics
Episode: Can You Really Trust That Revenue Projection? Inside How STR Data Actually Gets Made

Hosts

Michael Chang
Host of the show; STR Like The Best
Elizabeth Chang
Co-host and founder; STR Like The Best (Education/STR Concierge)

Reviews

5.0 out of 5 stars from 152 ratings
  • Like the best STR pod out there

    I love listening to Michael and Liz as they share about their learnings in the STR world and beyond. They set a high bar and are some of the savviest STR investors in the game with sound advice. They make an effort to hit on all aspects of STR investments and have a good breadth of guests. Highly recommend this pod!

    Apple Podcasts
    5
    MichaelKlein03
    United States3 months ago
  • Great, Helpful podcast for starting STR investing

    This podcast has been so helpful in my introduction to STRs. Michael does an awesome job with interviewing guests from all aspects of the STR business world. It’s really helped me in my first STR investment. I love all the pods …keep them coming.

    Apple Podcasts
    5
    AV1675
    United States5 months ago
  • Extremely informative

    Michael is clearly very experienced in this field based on his commentary throughout the podcasts. His guests are knowledgeable, relevant, and interesting to listen to. Michael knows the right questions to ask, knows when to probe, and went to just sit back and listen. Highly recommended show for anyone interested in STR’s as well as real estate in general.

    Apple Podcasts
    5
    Genny Orzolek
    United States2 years ago
  • A Must-Listen for Aspiring Airbnb Investors

    If you’re looking to dive into the world of short-term rental investing, look no further than this exceptional podcast. Featuring in-depth conversations with some of the most successful investors globally, this show is a goldmine of information for both newcomers and seasoned investors alike!

    Apple Podcasts
    5
    NLeung1
    United States2 years ago
  • Best STR Podcast

    This is the best STR podcast around! Very knowledgeable and down to earth with top quality guests that walk through their business models.

    Apple Podcasts
    5
    R._F.
    United States2 years ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Guests are described as knowledgeable and relevant to the STR space.
Listeners praise actionable guidance from experienced hosts and guests.
The host is praised for asking thoughtful questions and delivering high-quality content.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Talking Points

Recent interactions between the hosts and their guests.

63. From Spreadsheets to Scale: How Topkey Streamlines STR Finances (Without Losing Your Rewards Points)
Q: How does Topkey help with cash flow visibility and revenue recognition as you scale?
Topkey provides bank accounts with AP and revenue recognition features, direct integration with Amazon invoices, automatic tagging and GL mapping, and AI-assisted categorization to ensure the books reflect true cash movements, which helps managers see what they actually cash in and out and reconcile more accurately.
63. From Spreadsheets to Scale: How Topkey Streamlines STR Finances (Without Losing Your Rewards Points)
Q: Tell us about Topkey and what problem you're solving for property managers.
Topkey started as an expense management tool and evolved into a full financial operating system that streamlines card purchases, reimbursable expenses, and owner/vendor payouts, while offering direct integrations to PMS like HostAway and maintenance tools like Breezeway to unify end-to-end workflows.
60. The Brutal Truth Of Real Estate Market Today, Why It Matters to YOU?
Q: Can you give us the unvarnished truth of what's going on in the broader real estate market?
The market is in a downturn with significantly fewer transactions than in the past, driven by stricter lending and higher financing costs, though equity remains in property values; the key is to analyze deals carefully and look for opportunities where you can secure big discounts and favorable terms.
What Your CPA Gets Wrong About The STR Tax Loophole w/ Amanda Han & Matt MacFarland from Keystone CPA
Q: Definitionally, what is the short-term rental tax loophole? Why does it exist?
It allows people who own or operate STR properties to use paper losses from depreciation and related costs to offset ordinary income, potentially across all income types, as long as they meet material participation requirements; this makes STRs look more like active business activity than traditional passive real estate.
How AI Automates 90% of My Guest Messages (And Why Hosts Who Don't Adapt Will Get Left Behind)
Q: How does HelloHost differentiate itself from a simple chatbot, and what makes the multi-agent setup effective?
HelloHost uses a multi-agent system where different agents handle evaluation, response construction, and QA, coordinating to generate accurate, context-aware replies that a single bot could not reliably produce.

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Frequently Asked Questions About STR Like The Best

What is STR Like The Best about and what kind of topics does it cover?

A pragmatic, data-driven show focused on short-term rentals as a wealth-building vehicle. Across episodes, listeners hear from seasoned operators, investors, and technology-forward guests who discuss branding, design, automated operations, data-driven underwriting, tax strategies, and revenue management. The conversations tend to blend practical execution tips with broader market trends, often highlighting the role of software, AI, and scalable processes in growing profitable portfolios. The show stands out for its mix of real-world case studies, hands-on workflows, and a strong emphasis on long-term wealth-building through real estate and optimization strategies that appeal to high-earning professionals seeking durable cash flow.

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Which podcasts are similar to STR Like The Best?

These podcasts share a similar audience with STR Like The Best:

1. The Short Term Show
2. Tax Smart Real Estate Investors Podcast
3. Thanks For Visiting
4. Real Wealth Show: Real Estate Investing Podcast
5. BiggerPockets Real Estate Podcast

How many episodes of STR Like The Best are there?

STR Like The Best launched 3 years ago and published 81 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

How do I contact STR Like The Best?

Our systems regularly scour the web to find email addresses and social media links for this podcast. We scanned the web and collated all of the contact information that we could find in our podcast database. But in the unlikely event that you can't find what you're looking for, our concierge service lets you request our research team to source better contacts for you.

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What guests have appeared on STR Like The Best?

Recent guests on STR Like The Best include:

1. Jordan McDonough
2. Hailee Marie
3. Jeremy Werden
4. Julie Brinkman
5. Eli Cohen
6. Shaun Shirazian
7. Amanda Han
8. Matt MacFarland

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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