I quit. You win. Here's everything I know about STR...

surrounded by chick fil a and celsius cans

Hello Reader,

→ Note: Only 10 spots are available at $84/year before price increases. Lock in your rate here → (You must choose annually during checkout.)

Cashflow Diary | Direct - Founders Member

Get complete access to Cashflow Diary Direct, the premium newsletter for building cash flow, at our lowest-ever rate.... Read more

Look, I finally broke.

It's 1 AM, I'm surrounded by empty Celsius cans and Chick-fil-A wrappers in my makeshift "office" (aka my living room), and I just had an expensive realization:

I've been doing this all wrong.

For over a decade, I've helped families in 17 countries build successful STR businesses. Owned + Managed 400+ units. Created multiple 7-figure earners. Been paid thousands just for one hour of my time.

But here's what's keeping me up at night (besides the Celsius):

Every day, I get messages:

"Can I pick your brain over coffee?"

"Any chance for a quick call?"

"What would you do in my situation?"

And it kills me that I can't help everyone personally.

So at 2 AM last night, between my seventh piece of Chick-fil-A and what might have been my fifth Celsius, I made a decision:

I'm giving away everything.

Every system. Every template. Every AI tool. Every automation. Everything I'd tell you if we were working together in person - broken down into bite-sized pieces you can actually use.

Because here's the brutal truth: If your STR portfolio isn't earning at least $800 per month per bedroom in net income or maintaining a 30% net profit margin, you're leaving money on the table.

And I can't watch that happen anymore.

Here's what this means for you:

Starting now, EVERYONE gets my free newsletter every Monday and Thursday. This isn't some watered-down content - you'll get:

  • One actionable STR insight you can implement immediately
  • Basic implementation guides that actually work
  • Selected case studies showing what's possible
  • General market updates to keep you informed

But here's where it gets interesting...

For a small group of action-takers, I'm offering something I've never done before:

Introducing CASHFLOW DIARY DIRECT (Premium)

This is different. This is where you get EVERYTHING:

  • Not just insights - but complete, proven system
  • Not just guides - but my entire template library
  • Not just updates - but early access to what's working
  • Not just case studies - but live Q&A sessions with me
  • Not just market news - but behind-the-scenes access as we build

Plus, my complete AI implementation system that's changing everything:

  • Guest communication automation
  • Airbnb Listing optimization prompts
  • Price optimization strategies
  • Investor attraction sequences
  • Property analysis automation
  • Market research shortcuts
  • Content creation systems

FOUNDING MEMBER TIERS (Lock in your rate forever):

→ First 10 Members: $84/year (Save $386)

→ Next 15 Members: $120/year (Save $350)

→ Following 25 Members: $167/year (Save $303)

→ Regular Price: $470/year

Look, you have three choices:

  1. Keep struggling with outdated STR methods
  2. Pay thousands for private coaching
  3. Get everything I know for less than a night's STR booking

Choose wisely. (Make sure you choose the annual payment option during checkout).

Cashflow Diary | Direct - Founders Member

We're building this together, in public. Every test, every tool, every breakthrough - you'll see it all. Because that's how we all learn faster.

The STR landscape is changing rapidly. AI is transforming everything from guest communication to market analysis. Those who adapt will thrive. Those who don't will struggle to keep up.

To your success (and my next Celsius),

J. Massey, Cashflow Diary Founder, and riding a "Celsius high"

P.S. If you think this is crazy, you're right. It probably is. But I'm done watching people struggle when I know I can help. Get in now before I come to my senses →

Cashflow Diary | Direct - Founders Member

P.P.S. This Thursday's newsletter includes an AI prompt sequence that helped one host automate 80% of their guest communication. Early openers get first access.

J. Massey, Founder of Cashflow Diary & Financial Strategist

I've created frameworks making STR success accessible to everyone through step-by-step systems for raising capital, implementing AI-powered automation, and scaling portfolios. My approach combines innovative tools with practical, no-fluff strategies that help professionals leverage private capital for passive income.