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Artwork for STR Like The Best

STR Like The Best

Michael Chang
Short-Term Rentals
Airbnb
Short-Term Rental
Real Estate
Property Management
Real Estate Investing
Revenue Management
Real Estate Investment
Covid-19
Short-Term Rental Tax Loophole
Networking
Entrepreneurship
Artificial Intelligence
Taxes
Real Estate Flipping
Mentorship
Property Management Software
Tax Code
Experiential Hospitality
Guest Experience

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.

PublishesWeeklyEpisodes91Founded3 years ago
Number of ListenersCategories
InvestingBusinessEntrepreneurship

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Artwork for STR Like The Best

Latest Episodes

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... more

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 Ba... more

YouTube

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 e... more

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 a... more

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Recent Guests

Rajan Chida
Founder of Royal Oak Retreats, Virginia cabin developer
Royal Oak Retreats
Episode: From Shoe Reseller to Real Estate Developer: How Rajan Chida Built Royal Oak Retreats at 23
Robin Simon
DSCR lending expert, author of The Book on DSCR Loans
Author of The Book on DSCR Loans
Episode: The STR Financing Blueprint: When to Use DSCR Loans, Second Home Loans, and Everything in Between
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

Hosts

Michael Chang
Host of STR Like The Best, primary interviewer and strategist
Elizabeth
Co-host, focuses on collaboration and strategy

Reviews

5.0 out of 5 stars from 153 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 States6 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 States8 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.

Listeners praise practical, actionable STR insights and guest variety.
Audience notes high-quality, data-driven discussions and mentorship value.
Many comment on the host's ability to extract useful takeaways and real-world examples.

Chart Rankings

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

Talking Points

Recent interactions between the hosts and their guests.

From $180K Tax Bill to $110K Refund: What 9 Months in the Program Actually Looks Like
Q: How long did it take to go from intake to contract, and what was the bottleneck you faced?
We averaged about 45 days from intake to getting into contract. The biggest initial bottleneck was narrowing down where to invest and aligning on the right market and property with the guidance of the intake process and market discussions.
From $180K Tax Bill to $110K Refund: What 9 Months in the Program Actually Looks Like
Q: What would you say to someone who hasn't joined yet but is on the fence about real estate and tax-efficient STR investments?
Don't get stuck in analysis paralysis. Do the work, use available resources, and understand that it's a substantial commitment, but with mentorship and a clear process you'll be able to move quickly, make decisions, and build long-term wealth.
The STR Financing Blueprint: When to Use DSCR Loans, Second Home Loans, and Everything in Between
Q: When is DSCR financing most advantageous for a new investor?
DSCR financing is advantageous for investors who are growing a portfolio and want flexibility with ownership structure; it works well for both first-time investors and those building a larger national portfolio, especially once they reach a point where conventional loans become less efficient.
The STR Financing Blueprint: When to Use DSCR Loans, Second Home Loans, and Everything in Between
Q: What does DSCR stand for and why is it a big deal for STR financing?
DSCR stands for Debt Service Coverage Ratio, and it qualifies loans based on the property's ability to cover debt payments rather than the borrower's personal income, making it more flexible for investors with multiple STRs.
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.

Audience Metrics

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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 practical, entrepreneur-minded show focused on scaling short-term rentals through real-world strategies, data-driven underwriting, and smart financing. Across episodes, listeners hear candid journeys from couples and individuals building multi-property portfolios, leveraging mentorship, market intelligence, and practical workflows to accelerate growth. Rich threads run through tax optimization (including 100-hour participation rules and married-couple strategies), financing (DSCR and other loan types), design and branding as revenue drivers, and technology-enabled ops. Noteworthy is the recurring emphasis on actionable, repeatable methods, community support, and a holistic view of wealth-building that blends operations, finance, and perso... more

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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. Thanks For Visiting
3. Tax Smart Real Estate Investors Podcast
4. BiggerPockets Real Estate Podcast
5. Real Estate Rookie

How many episodes of STR Like The Best are there?

STR Like The Best launched 3 years ago and published 91 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. Rajan Chida
2. Robin Simon
3. Jordan McDonough
4. Hailee Marie
5. Jeremy Werden
6. Julie Brinkman
7. Eli Cohen
8. Shaun Shirazian

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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