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Cashflow Diary™

Cashflow Diary™

J. Massey 698 Episodes Oct 14, 2026

J. Massey, a real estate investor and entrepreneur, shares strategies for real estate and business investing. He offers free training courses covering prospecting, offers, closing deals, buying, selling, wholesaling, fix & flips, and rehabs. The podcast aims to help new and experienced investors break through the clutter and become successful entrepreneurs.

Episodes

Is Airbnb Profitable? The $800-Per-Bedroom Test
Is Airbnb Profitable? The $800-Per-Bedroom Test Oct 14, 2026 633 Six years, a three-bedroom rental, and an annual net profit of zero. The platform got paid. The manager got paid. The cleaner got paid. The owner didn't. In this episode, J. Massey walks through two recent conversations (details changed) with experienced short-term rental owners who were making money for everyone but themselves. He shows exactly where the money was leaking. What you'll le
Rental Property Cash Flow Calculator: How to Calculate It Before You Buy
Rental Property Cash Flow Calculator: How to Calculate It Before You Buy Apr 20, 2026 343 AI disclosure: This episode is narrated by an AI-generated voice. Most investors calculate rental property cash flow wrong — and they don't find out until they own the property. The mistake isn't arithmetic. It's leaving out entire expense categories. In this episode, J. Massey walks through the complete formula he actually uses to analyze deals — every line item, with real numbers, in th
FIFA Just Canceled 70% of Its World Cup Hotel Blocks — Here's What That Actually Means
FIFA Just Canceled 70% of Its World Cup Hotel Blocks — Here's What That Actually Means Apr 11, 2026 540 AI disclosure: This episode is narrated by an AI-generated voice. FIFA Just Canceled 70% of Its World Cup Hotel Blocks — Here's What That Actually Means You probably saw the headline and thought the World Cup was in trouble. "FIFA cancels thousands of hotel rooms across World Cup host cities." It sounds like a disaster. But if you're an STR operator, that headline is one of the best sig
The Real STR Playbook for 2026
The Real STR Playbook for 2026 Apr 10, 2026 723 AI disclosure: This episode is narrated by an AI-generated voice. Three states just passed pro-short-term-rental laws while everyone else cracks down. In this episode, J. Massey breaks down the three biggest shifts in the STR landscape right now — platform dependency, the experience-first framework, and the regulation opportunity — plus what you need to do about each one.In This EpisodeWh
The Master Prompt That Changed Everything: AI, STRs, and Overcoming My Communication Block
The Master Prompt That Changed Everything: AI, STRs, and Overcoming My Communication Block May 2, 2025 342 AI disclosure: This episode is narrated by an AI-generated voice. Discover the personal and professional journey behind the launch of Cashflow Diary Direct, a new newsletter designed to deliver bite-sized, actionable short-term rental (STR) strategies and AI tools directly to your inbox. Discover the "master prompt" that not only revolutionized his business operations but also enabled him
Mastering Deal Structure: Using the Profit Analysis Quadrant (PAQ) and AI to Secure Funding
Mastering Deal Structure: Using the Profit Analysis Quadrant (PAQ) and AI to Secure Funding Apr 8, 2025 1024 AI disclosure: This episode is narrated by an AI-generated voice. 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 CO
AI Revolution: Transforming Your Real Estate Business from Top to Bottom
AI Revolution: Transforming Your Real Estate Business from Top to Bottom Mar 21, 2025 543 AI disclosure: This episode is narrated by an AI-generated voice. 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 ho
AI's Role in Transforming Real Estate Investing
AI's Role in Transforming Real Estate Investing Mar 14, 2025 852 AI disclosure: This episode is narrated by an AI-generated voice. 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 lea
Breaking Through Habits And Mindsets Holding You Back
Breaking Through Habits And Mindsets Holding You Back Apr 7, 2023 1363 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 y
How Short Term Rental Industry Can Help Anyone Generate Wealth
How Short Term Rental Industry Can Help Anyone Generate Wealth Apr 4, 2023 1439 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
The First Step To Building Your Short Term Rental Empire
The First Step To Building Your Short Term Rental Empire Mar 31, 2023 633 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
The Best Storage Solutions For Your Gold And Silver Investments
The Best Storage Solutions For Your Gold And Silver Investments Mar 28, 2023 909 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

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