Why Your STR Business Is Dying (And Why “Working Harder” Won’t Save It)

The systematic automation gap is killing manual operators—and most don’t even know they’re already dead

Oct 15 • 

J. Massey

7

September 2025

🏠 The Master Key vs. The Property Inspector:

Why 70% of STR Operators Are Still Missing the Mark

Sep 26 • 

J. Massey

7

Why 97% of STR Operators Are Lost at Sea

(And The Navigation System That Changes Everything)

Sep 25 • 

J. Massey

7

7 Mistakes You're Making with STR Automation (and How to Fix Them)

Last week, I got a panicked message from Sarah, a member who owns three Airbnbs in Nashville.

Sep 11 • 

J. Massey

4

Your Mindset Isn't the Problem. This Is.

The $48.4 Billion Personal Development Industry Is Lying to You About What's Really Holding Your STR Business Back

Sep 10 • 

J. Massey

5

Why "Working Hard" Is a Lie

83.9% of STR operators are accidentally running lottery ticket businesses—and the mathematics are BRUTAL about what happens next

Sep 5 • 

J. Massey

3

2

The $1.4 Billion Lie: Why the Lottery Is Destroying Your Business Dreams

(And The Systematic Truth That Actually Works)

Sep 4 • 

J. Massey

4

Why Most Operators Are Failing Wrong

(And The Systematic Truth About Business Survival)

Sep 3 • 

J. Massey

4

August 2025

Why Most STR Operators Can't Scale Past Their Own Personal Limitations

(And The Shocking Solution That Changes Everything)

Aug 30 • 

J. Massey

8

1

July 2025

Why Your 'Irrelevant' Past Experience is More Valuable Than an MBA

(And How Any Background Can Build STR Wealth)

Jul 20 • 

J. Massey

7

Why 'Seeing is Believing' Keeps You Poor

(And How Believing Creates the Reality That Makes You Rich)

Jul 19 • 

J. Massey

7

Most STR 'Investors' Are Just Landlords with Better Marketing

(And Why Real Knowledge Creates Unfair Advantages Worth Millions)

Jul 18 • 

J. Massey

3