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Why 99% of STR Hosts Are Bleeding Money (And Don't Even Know It)
The $6,416 mistake that proves most rental hosts can't do 6th grade math
Jul 1
•
J. Massey
6
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Why 99% of STR Hosts Are Bleeding Money (And Don't Even Know It)
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June 2025
How to Win When Everyone Has the Same Tools
Building competitive moats in the age of automation equality
Jun 29
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J. Massey
4
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How to Win When Everyone Has the Same Tools
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🔥 AUTOMATION IS MURDERING YOUR STR PROFITS WHILE YOU SLEEP
here's the market data proving this bloodbath is accelerating...
Jun 28
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J. Massey
3
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🔥 AUTOMATION IS MURDERING YOUR STR PROFITS WHILE YOU SLEEP
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The AI Apocalypse: Why "Democratized" Tools Are Your Business's Death Sentence
How Silicon Valley's biggest lie is about to bankrupt millions of entrepreneurs - and why the "experts" pushing AI tools are your real competitors
Jun 27
•
J. Massey
6
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The AI Apocalypse: Why "Democratized" Tools Are Your Business's Death Sentence
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Your 'Systems' Are Why You Can't Take a Vacation: The $50K Opportunity Cost of Playing Business Owner
Most STR operators think checking messages poolside counts as 'automated business management.' Here's why that mentality is costing you six figures…
Jun 26
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J. Massey
2
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Your 'Systems' Are Why You Can't Take a Vacation: The $50K Opportunity Cost of Playing Business Owner
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Government PAYS You to Get Rich (But Only If You Know This Secret)
Why STR operators have the ultimate tax advantage—and how understanding this one framework changes everything
Jun 25
•
J. Massey
2
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Government PAYS You to Get Rich (But Only If You Know This Secret)
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The Supply/Demand Math That Makes 2025 Perfect for STR Expansion (Despite Economic Headlines)
Why Market Uncertainty Creates Optimal Conditions for Strategic STR Investment
Jun 24
•
J. Massey
7
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The Supply/Demand Math That Makes 2025 Perfect for STR Expansion (Despite Economic Headlines)
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Why 90% of STR Operators Never Hit $800+ Per Bedroom (The Decision Problem No One Talks About)
The uncomfortable truth about why 'doing your research' is actually destroying your rental business.
Jun 23
•
J. Massey
9
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Why 90% of STR Operators Never Hit $800+ Per Bedroom (The Decision Problem No One Talks About)
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Why 97% of People Will Never Escape Path A
And Why You Might Be One of Them
Jun 22
•
J. Massey
7
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Why 97% of People Will Never Escape Path A
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I Outsold the Entire Sales Team. Then I Quit.
The insurance underwriter who humiliated his sales team, then walked out to build a rental empire (and why your "safe" job is the riskiest bet you'll…
Jun 21
•
J. Massey
6
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I Outsold the Entire Sales Team. Then I Quit.
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Why I Almost Gave Up on AI
(And How Manufacturing Principles Saved My $75K Consulting Project)
Jun 20
•
J. Massey
3
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Why I Almost Gave Up on AI
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🔥 Why 87% of Hosts Run Real Estate Charities
(Not Businesses)
Jun 19
•
J. Massey
4
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🔥 Why 87% of Hosts Run Real Estate Charities
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