All Episodes

March 21, 2023 12 mins

🔍 GET THE STR INSIGHTS THAT CREATED 7-FIGURE HOSTS
After managing 400+ units and helping STR hosts in 17 countries achieve $800+ monthly net income per bedroom, I'm sharing my best strategies - free.

Every Monday and Thursday, you'll get:
✓ One actionable STR automation strategy
✓ Data-driven market insights that matter
✓ Implementation frameworks that work
✓ Real case studies from our 20,000+ community

No fluff. No theory. Just proven systems from my living room "office" (fueled by Celsius and Chick-fil-A).

These are the exact insights that help our community achieve:
• 30%+ profit margins
• 80% automated guest communication
• 5+ hours saved weekly

👉 Join 20,000+ successful STR hosts at https://newsletter.cashflowdiary.com/welcome

Now, let's dive into today's episode...


In this episode of Cash Flow Diary, host J Massey was left speechless by an unbelievable tale about  property damage that occurred from a coaching client working in the short term rental industry.

During a Q+A session with coaching clients, J Massey guides coaching clients as they build their short term rental empire. J thought he had heard everything while working in the short term rental industry. J would never have thought that a customer would remove a piece of the property from a short term rental property, but he was wrong. J advises his clients on how to proceed when the unthinkable happens.

Also in this episode:

  • Where there is chaos, there is cash flow
  • How the pandemic changed customers' needs have changed with the rise of remote working
  • The importance of listening to your landlord
  • How do you calculate fines for property damage
About Cashflow Diary™ 

Jay Massey is a full-time Real Estate Investor, Entrepreneur, Popular Podcast Host, Author, Speaker, Coach & All-Around Problem Solver.

Cashflow Diary is a short-term rental hospitality training company. We show people how to build their own short-term rental business (without needing to buy or own any property) so they can thrive financially.

Heralded as the most advanced short-term rental training in the industry, Cashflow Diary enjoys creating content and communities that are solely focused on developing individuals into powerful business owners. Founded by J. Massey, Cashflow Diary exists to create short-term rental entrepreneurs. No matter your passion, he believes that running a hospitality business will change people’s lives…

 Cashflow Diary is here to share all of it with you.

 


🏠 Want to Join the Elite 10% of Short-Term Rental Hosts?

Dear Future Top Performer,

Are you tired of working harder instead of smarter in your STR business? Here's a wake-up call: The most successful hosts aren't grinding 24/7 – they're leveraging a proven formula that transforms average properties into profit powerhouses.

Let me share something game-changing with you...

There's a simple yet powerful equation that's revolutionizing the STR industry:
L × C × F × M = GP

This isn't just another fancy acronym – it's the exact blueprint top performers use to:
• Generate consistent leads without burning out
• Convert browsers into eager bookers
• Maximize guest frequency (hello, repeat customers!)
• Amplify their margins while others race to the bottom

Right now, you're probably leaving thousands on the table. The truth? 80% of your potential profits are locked behind just 20% of the right actions.

Ready to stop bleeding money and start leading the pack?

Join our newsletter today and get weekly insights that will help you:
✓ Master the Growth Formula
✓ Optimize your listing for maximum visibility
✓ Create an irresistible guest experience
✓ Scale your business the smart way

Don't let another day pass watching others succeed while you're stuck in the grind.

👉 Click here to join the newsletter and start your journey to the top 10%!

Mark as Played

Advertise With Us

Popular Podcasts

On Purpose with Jay Shetty

On Purpose with Jay Shetty

I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

Stuff You Should Know

Stuff You Should Know

If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2026 iHeartMedia, Inc.