Cashflow Diary

🔍 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...

EPISODE OVERVIEW:
Building on previous discussions about AI in real estate, this episode focuses on the critical skill of structuring deals that secure funding. J. Massey introduces his proprietary Profit Analysis Quadrant (PAQ) system and demonstrates how to match investment opportunities with investor needs.

KEY CONCEPTS COVERED:

1. Investor Identity Analysis
- Understanding individual investor "puzzles"
- Distinguishing between "Nordstrom" and "Walmart" investors
- The importance of becoming a "professional information gatherer" (PIG)

2. The Profit Analysis Quadrant (PAQ)
- Appreciation: Long-term value growth
- Depreciation: Tax advantages
- Amortization: Equity building through debt reduction
- Cash Flow: Regular income generation

3. Essential Investor Interview Questions:
- Past investment experiences
- Financial goals and timeline
- Risk tolerance assessment
- Investment motivations
- Current investment concerns

4. Deal Structuring Principles:
- Clarity and transparency
- Alignment with investor identity
- Flexibility and customization
- Matching structure to investor needs

5. AI Implementation in Deal Presentation:
- AI-powered pitch deck creation
- Financial modeling capabilities
- Visual representation tools
- Personalization strategies

FEATURED CASE STUDY:
Detailed example of structuring a deal for a retiree seeking steady income, demonstrating how understanding investor identity led to successful funding.

ACTIONABLE TAKEAWAYS:
1. Focus on conversations, not pitches
2. Use the 70/30 listening rule
3. Implement the "Really? Why?" technique
4. Regularly reassess your own investor identity
5. Align deal structure with investor goals

READY TO TRANSFORM YOUR STR BUSINESS?
Enjoyed this episode? Here's how to get more actionable insights:

Stop struggling with outdated STR strategies. Join 20,000+ hosts who get my battle-tested systems delivered straight to their inbox - twice weekly, zero fluff.

Every newsletter shares:
✓ One proven STR automation strategy
✓ Real implementation steps you can use today
✓ Market insights from managing 400+ units
✓ Systems that create $800+ monthly net income per bedroom

Our community consistently achieves:
• 30%+ profit margins
• 80% automated guest communications
• 5+ hours saved weekly
• Predictable booking patterns

💰 FREE FOR PODCAST LISTENERS
Get immediate access to the same strategies that have created multiple 7-figure STR owners across 17 countries.

➡️ Visit newsletter.cashflowdiary.com/welcome

Every day you wait is another day of potential profit lost.

Note: This is the raw, unfiltered knowledge from my makeshift living room "office" (fueled by Celsius and Chick-fil-A) - no theory, just proven systems that work.

🔍 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...

J. Massey dives deep into how artificial intelligence is transforming real estate operations, particularly for short-term rental businesses. Building on last episode's strategies for finding investors, J. reveals how AI can optimize everything from property management to guest communications and investor relations. Learn how these powerful tools can help you execute with greater precision and scale your business more effectively than ever before.

Topics Covered

• Choosing the right AI tools for different business functions
• Using AI for market research and property management
• Implementing agile methodology with AI assistance
• Creating personalized guest communications at scale
• Streamlining corporate bookings with predictive analysis
• Maintaining investor relationships with targeted follow-up sequences
• Optimizing all business communications for maximum impact

Resources Mentioned

AI Tools

• Perplexity AI: Research tool for market trends, guest preferences, and competitor analysis
• Claude AI: Strategic planning, coding assistance, and data visualization

Free Downloads

• 5-Minute Investor Finder Guide: Download at begininvestingnow.com

Stay Connected

• Cashflow Diary Newsletter: Sign up at podcast.cashflowdiary.com
• Next Episode: AI-Powered Deal Structuring and Presentation

Connect With J. Massey

• Website: cashflowdiary.com
• Instagram: @cashflowdiary
• Facebook: Cashflow Diary
• YouTube: Cashflow Diary

Support The Show

If you enjoyed this episode, please subscribe, share with a friend, and leave a rating and review on your favorite podcast platform.

READY TO TRANSFORM YOUR STR BUSINESS?
Enjoyed this episode? Here's how to get more actionable insights:

Stop struggling with outdated STR strategies. Join 20,000+ hosts who get my battle-tested systems delivered straight to their inbox - twice weekly, zero fluff.

Every newsletter shares:
✓ One proven STR automation strategy
✓ Real implementation steps you can use today
✓ Market insights from managing 400+ units
✓ Systems that create $800+ monthly net income per bedroom

Our community consistently achieves:
• 30%+ profit margins
• 80% automated guest communications
• 5+ hours saved weekly
• Predictable booking patterns

💰 FREE FOR PODCAST LISTENERS
Get immediate access to the same strategies that have created multiple 7-figure STR owners across 17 countries.

➡️ Visit newsletter.cashflowdiary.com/welcome

Every day you wait is another day of potential profit lost.

Note: This is the raw, unfiltered knowledge from my makeshift living room "office" (fueled by Celsius and Chick-fil-A) - no theory, just proven systems that work.

🔍 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...

Welcome to Season 3 of Cashflow Diary! 

After an enlightening break, J. Massey returns with a revolutionary approach to finding investors.

In this episode, J. shares his personal discovery of how AI can transform your ability to identify and connect with potential investors – even if they're already in your network.

You'll learn the exact "5-Minute Investor Finder" system, understand how to craft perfect approach messages, and see why the maturing short-term rental market makes these tools more valuable than ever.

Whether you think you know no investors or you're already raising capital, this episode will change how you build your real estate business.

Download the free implementation guide at begininvestingnow.com and start finding investors today.

READY TO TRANSFORM YOUR STR BUSINESS?
Enjoyed this episode? Here's how to get more actionable insights:

Stop struggling with outdated STR strategies. Join 20,000+ hosts who get my battle-tested systems delivered straight to their inbox - twice weekly, zero fluff.

Every newsletter shares:
✓ One proven STR automation strategy
✓ Real implementation steps you can use today
✓ Market insights from managing 400+ units
✓ Systems that create $800+ monthly net income per bedroom

Our community consistently achieves:
• 30%+ profit margins
• 80% automated guest communications
• 5+ hours saved weekly
• Predictable booking patterns

💰 FREE FOR PODCAST LISTENERS
Get immediate access to the same strategies that have created multiple 7-figure STR owners across 17 countries.

➡️ Visit newsletter.cashflowdiary.com/welcome

Every day you wait is another day of potential profit lost.

Note: This is the raw, unfiltered knowledge from my makeshift living room "office" (fueled by Celsius and Chick-fil-A) - no theory, just proven systems that work.

🔍 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...

On today's episode of Cash Flow Diary, J. Massey explores the habits and mindsets that are holding you back from scaling up and growing your short term rental empire.

Despite a hunger for knowledge and self-improvement, many individuals find themselves stuck in unproductive routines that hinder their progress. J offers actionable advice for breaking free from these patterns and shifting your mindset towards growth and success.

Also in this episode: 

• Suffering leads to perseverance
• The problem with qualified retirement accounts
• The importance of believing that wealth is for everyone
• A sequence of events that can destroy your liquidity

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.

READY TO TRANSFORM YOUR STR BUSINESS?
Enjoyed this episode? Here's how to get more actionable insights:

Stop struggling with outdated STR strategies. Join 20,000+ hosts who get my battle-tested systems delivered straight to their inbox - twice weekly, zero fluff.

Every newsletter shares:
✓ One proven STR automation strategy
✓ Real implementation steps you can use today
✓ Market insights from managing 400+ units
✓ Systems that create $800+ monthly net income per bedroom

Our community consistently achieves:
• 30%+ profit margins
• 80% automated guest communications
• 5+ hours saved weekly
• Predictable booking patterns

💰 FREE FOR PODCAST LISTENERS
Get immediate access to the same strategies that have created multiple 7-figure STR owners across 17 countries.

➡️ Visit newsletter.cashflowdiary.com/welcome

Every day you wait is another day of potential profit lost.

Note: This is the raw, unfiltered knowledge from my makeshift living room "office" (fueled by Celsius and Chick-fil-A) - no theory, just proven systems that work.

🔍 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...

On today's episode of Cash Flow Diary, J. Massey hosts a Q+A session about how working with the short term rental industry can help anyone generate the wealth they seek. 

During this Q+A session with clients, J answers a wide range of questions from clients and provides answers and strategies they can use to help them start building their own short term rental empire.

Also in this episode:

• How do you leverage what you already have
• Using referral codes for Uber and Lyft to make your rental stand out
• The rule of adverse selection
• The difference between an Airbnb and a bed and breakfast
• 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.

READY TO TRANSFORM YOUR STR BUSINESS?
Enjoyed this episode? Here's how to get more actionable insights:

Stop struggling with outdated STR strategies. Join 20,000+ hosts who get my battle-tested systems delivered straight to their inbox - twice weekly, zero fluff.

Every newsletter shares:
✓ One proven STR automation strategy
✓ Real implementation steps you can use today
✓ Market insights from managing 400+ units
✓ Systems that create $800+ monthly net income per bedroom

Our community consistently achieves:
• 30%+ profit margins
• 80% automated guest communications
• 5+ hours saved weekly
• Predictable booking patterns

💰 FREE FOR PODCAST LISTENERS
Get immediate access to the same strategies that have created multiple 7-figure STR owners across 17 countries.

➡️ Visit newsletter.cashflowdiary.com/welcome

Every day you wait is another day of potential profit lost.

Note: This is the raw, unfiltered knowledge from my makeshift living room "office" (fueled by Celsius and Chick-fil-A) - no theory, just proven systems that work.

🔍 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...

On today's episode of Cash Flow Diary, J. Massey hosts a Q+A session with coaching clients about the first steps needed to build your short term rental empire.

There are a lot of steps involved when it comes to building your short term rental empire. During Q+A calls with coaching clients, J shares the importance of changing your mindset and how it will have an astronomical impact on your business over time.

Also in this episode:

• You don't rise to the level of your goals; you fall to the level of your systems
• How habits are the compound interest of self-improvement
• The importance of tracking your sleep and water intake
• Habits are the compound interest of self improvement, the effects of your habits multiply as you repeat them. 

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.

READY TO TRANSFORM YOUR STR BUSINESS?
Enjoyed this episode? Here's how to get more actionable insights:

Stop struggling with outdated STR strategies. Join 20,000+ hosts who get my battle-tested systems delivered straight to their inbox - twice weekly, zero fluff.

Every newsletter shares:
✓ One proven STR automation strategy
✓ Real implementation steps you can use today
✓ Market insights from managing 400+ units
✓ Systems that create $800+ monthly net income per bedroom

Our community consistently achieves:
• 30%+ profit margins
• 80% automated guest communications
• 5+ hours saved weekly
• Predictable booking patterns

💰 FREE FOR PODCAST LISTENERS
Get immediate access to the same strategies that have created multiple 7-figure STR owners across 17 countries.

➡️ Visit newsletter.cashflowdiary.com/welcome

Every day you wait is another day of potential profit lost.

Note: This is the raw, unfiltered knowledge from my makeshift living room "office" (fueled by Celsius and Chick-fil-A) - no theory, just proven systems that work.

🔍 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...

On today's episode of Cash Flow Diary, J. Massey hosts a Q+A session with coaching clients about storage solutions for their gold and Silver.

When it comes to storage for gold and silver J Massey has heard it all. J speaks with a group of coaching clients and provides advice on safely storing your gold and Silver without burying them in the backyard.

Also in this episode:

• The reason why coin shops often next to gun shops
• Why is Silver counterfeited less than gold 
• Even Benjamin Franklin kept some of his assets across seven countries.
• Gold and Silver are not always insurable 

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.

READY TO TRANSFORM YOUR STR BUSINESS?
Enjoyed this episode? Here's how to get more actionable insights:

Stop struggling with outdated STR strategies. Join 20,000+ hosts who get my battle-tested systems delivered straight to their inbox - twice weekly, zero fluff.

Every newsletter shares:
✓ One proven STR automation strategy
✓ Real implementation steps you can use today
✓ Market insights from managing 400+ units
✓ Systems that create $800+ monthly net income per bedroom

Our community consistently achieves:
• 30%+ profit margins
• 80% automated guest communications
• 5+ hours saved weekly
• Predictable booking patterns

💰 FREE FOR PODCAST LISTENERS
Get immediate access to the same strategies that have created multiple 7-figure STR owners across 17 countries.

➡️ Visit newsletter.cashflowdiary.com/welcome

Every day you wait is another day of potential profit lost.

Note: This is the raw, unfiltered knowledge from my makeshift living room "office" (fueled by Celsius and Chick-fil-A) - no theory, just proven systems that work.

🔍 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...

On today's episode of Cash Flow Diary, J. Massey shares why he enjoys teaching families how to generate wealth to achieve finical freedom within the short term rental industry.

In this episode of Cash Flow Diary, J. Massey shares why he enjoys teaching families how to generate wealth to achieve financial freedom within the short term rental industry.

Anytime J is being interviewed; he is always asked the same question "why do you do what you do?" Something J tells his team all the time "the reason Cash Flow Diary exists is that I know their families want to generate wealth but don't know how to harness their unique skill set. Building a short term rental empire provides operatives for working families to achieve their goal of financial freedom. 

Also in this episode:

• The power of disconnecting your income from the clock
• Financial freedom means having a choice of how you spend your time
• The biggest lessons J took away from 2020
• Stop assuming that we all have the same real estate knowledge 

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.

READY TO TRANSFORM YOUR STR BUSINESS?
Enjoyed this episode? Here's how to get more actionable insights:

Stop struggling with outdated STR strategies. Join 20,000+ hosts who get my battle-tested systems delivered straight to their inbox - twice weekly, zero fluff.

Every newsletter shares:
✓ One proven STR automation strategy
✓ Real implementation steps you can use today
✓ Market insights from managing 400+ units
✓ Systems that create $800+ monthly net income per bedroom

Our community consistently achieves:
• 30%+ profit margins
• 80% automated guest communications
• 5+ hours saved weekly
• Predictable booking patterns

💰 FREE FOR PODCAST LISTENERS
Get immediate access to the same strategies that have created multiple 7-figure STR owners across 17 countries.

➡️ Visit newsletter.cashflowdiary.com/welcome

Every day you wait is another day of potential profit lost.

Note: This is the raw, unfiltered knowledge from my makeshift living room "office" (fueled by Celsius and Chick-fil-A) - no theory, just proven systems that work.

🔍 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

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.

READY TO TRANSFORM YOUR STR BUSINESS?
Enjoyed this episode? Here's how to get more actionable insights:

Stop struggling with outdated STR strategies. Join 20,000+ hosts who get my battle-tested systems delivered straight to their inbox - twice weekly, zero fluff.

Every newsletter shares:
✓ One proven STR automation strategy
✓ Real implementation steps you can use today
✓ Market insights from managing 400+ units
✓ Systems that create $800+ monthly net income per bedroom

Our community consistently achieves:
• 30%+ profit margins
• 80% automated guest communications
• 5+ hours saved weekly
• Predictable booking patterns

💰 FREE FOR PODCAST LISTENERS
Get immediate access to the same strategies that have created multiple 7-figure STR owners across 17 countries.

➡️ Visit newsletter.cashflowdiary.com/welcome

Every day you wait is another day of potential profit lost.

Note: This is the raw, unfiltered knowledge from my makeshift living room "office" (fueled by Celsius and Chick-fil-A) - no theory, just proven systems that work.