Cashflow Diary™
by J. Massey
Latest episode
Airbnb Self Check-In: How to Take Yourself Off the Front Door
Airbnb Self Check-In: How to Take Yourself Off the Front Door
About this podcast
Cashflow Diary™ is the podcast for short-term rental owners who want their properties to actually pay them.
Host J. Massey is a real estate investor, sales coach, and master facilitator of Robert Kiyosaki's CASHFLOW™ 101 game. He breaks down real numbers from real client conversations: pricing, platform fees, direct bookings, systems, and the habits that quietly cap experienced hosts.
New episodes every Tuesday.
Want a second set of eyes on your numbers? Book your complimentary one-on-one diagnostic call at cashflowdiary.com/diagnostic
Many episodes are narrated with J. Massey's own licensed AI voice clone, built from his own recordings and real client conversations.
Episodes
The newest 50 of 707 episodes
- Airbnb Self Check-In: How to Take Yourself Off the Front Door · 11 min · Season 4 Episode 10Take yourself off the front door: lockbox, keypad or smart lock, unique codes, a backup plan, what to ask first, and the arrival message.
- Airbnb LLC: What to Check and Who to Ask Before You File · 10 min · Season 4 Episode 9Should your Airbnb be in an LLC? What one does and doesn't do, the tax default, insurance, your loan or lease, yearly cost, and who to ask first.
- Airbnb Cleaner: Your Most Important Hire and How to Keep a Good One · 10 min · Season 4 Episode 8Why your Airbnb cleaner is the most important hire you make, what to look for, and how to keep a good one: pay, supplies, photos and a backup.
- Direct Booking Site for Airbnb Hosts: When It Pays and How to Start · 10 min · Season 4 Episode 7When does a direct booking site pay for an Airbnb host? The fee math, the break-even, Airbnb's off-platform rules, and 6 steps to start.
- Is Airbnb Legal in My City? 4 Places to Check Before You Sign a Lease · 9 min · Season 4 Episode 6Is Airbnb legal in your city? Before you sign a lease, check 4 places: the city code, the permit office, the HOA, and the lease.
- Not a Money Person? You Can't Learn and Look Good at the Same Time · 9 min · Season 4 Episode 5Think you're not a money person? You might be on level two of four. The four levels of learning, and one question to ask this week.
- 69 Days Left: Decide, or Let Time Decide for You · 8 min · Season 4 Episode 469 days are left in the year. If you don't decide what changes, time decides for you. Why we wait, and one daily result to start with tonight.
- Job Security: Why One Paycheck Is a Single Point of Failure · 8 min · Season 4 Episode 3If your job ended tomorrow, what stops? One paycheck is a single point of failure. Build a fail-safe at home and in your rentals before you need it.
- Airbnb Minimum Stay: The Setting That Turns Guests Away While You Sleep · 7 min · Season 4 Episode 2Your Airbnb minimum stay can turn guests away while you sleep. 16 lost inquiries at one of our properties came down to 2 reasons. One was free to fix.
- Is Airbnb Profitable? The $800-Per-Bedroom Test · 11 min · Season 4 Episode 1Two experienced Airbnb owners, one problem: everyone got paid except them. Where the money leaks, and two tests to find yours.
- Rental Property Cash Flow Calculator: How to Calculate It Before You Buy · 6 min · Season 1Most investors calculate rental property cash flow wrong — leaving out entire expense categories. In this episode, J. Massey walks through the complete formula line by line…
- FIFA Just Canceled 70% of Its World Cup Hotel Blocks — Here's What That Actually Means · 9 min · Season 1FIFA released tens of thousands of hotel rooms across World Cup host cities. Everyone thinks it's bad news — it's actually one of the best STR signals of the year. J. breaks down…
- The Real STR Playbook for 2026 · 12 min · Season 1 Episode 697J. Massey breaks down the three biggest shifts in the STR landscape for 2026 — platform dependency, the experience-first framework, and the regulation opportunity.
- The Master Prompt That Changed Everything: AI, STRs, and Overcoming My Communication Block · 6 min · Season 3 Episode 4AI 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…
- Mastering Deal Structure: Using the Profit Analysis Quadrant (PAQ) and AI to Secure Funding · 17 min · Season 3 Episode 3AI 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…
- AI Revolution: Transforming Your Real Estate Business from Top to Bottom · 9 min · Season 3 Episode 2AI 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…
- AI's Role in Transforming Real Estate Investing · 14 min · Season 3 Episode 1Welcome 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…
- Breaking Through Habits And Mindsets Holding You Back · 23 min · Season 1 Episode 691On 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…
- How Short Term Rental Industry Can Help Anyone Generate Wealth · 24 min · Season 1 Episode 690On 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…
- The First Step To Building Your Short Term Rental Empire · 11 min · Season 1 Episode 689On 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…
- The Best Storage Solutions For Your Gold And Silver Investments · 15 min · Season 1 Episode 688On 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…
- Teaching Families How To Achieve Financial Freedom In The Short Term Rental Industry · 10 min · Season 1 Episode 687On 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…
- Unbelievable Tales From The Short Term Rental Industry That Left J Massey Speechless · 11 min · Season 1 Episode 686In 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…
- How To Get Rich Quick In The Short Term Real Estate Industry · 16 min · Season 1 Episode 685In this episode of Cash Flow Diary, J Massey teaches you how to get rich quickly while working in the short-term real estate industry. When most people hear the term "get rich…
- How You Can Remedy The Situation If Somebody Is Smoking In Your Unit · 7 min · Season 1 Episode 684In this episode of Cash Flow Diary, J Massey hosts a Q+A with coaching clients about what to do when somebody is smoking in your unit and how you can remedy the situation. When…
- How To Negotiate A Short Term Real Estate Rental Unit Lease · 8 min · Season 1 Episode 683In this episode of Cash Flow Diary, J Massey discusses how you can negotiate your short term real estate until lease. When it comes to renting out Short Term Real Estate Units…
- Security Tools And Technology For Renting Out Your Short Term Rental Unit · 14 min · Season 1 Episode 682In this episode of Cash Flow Diary, J Massey shares security tips for renting out your short term rental unit. Have you ever wanted to start hosting guests, but have safety or…
- Make Your Short Term Rental Property Profitable With These Insider Secrets · 7 min · Season 1 Episode 681In today's episode of Cash Flow Diary, J Massey shares insider secrets on making your short-term rental property profitable. Furniture is one of the biggest expenses when getting…
- What Happens To The Short Term Real Estate Empire You’ve Built When Someone Else Takes Over · 8 min · Season 1 Episode 680In today's episode of Cash Flow Diary, host J. Massey explores what happens to your short term real estate empire when it's time for somebody else to take over. A lot goes into…
- To Have A Business Partner Or Not To Have A Business Partner, That Is The Question · 10 min · Season 1 Episode 679On today's episode of Cash Flow Diary, J. Massey explores the scenario that all entrepreneurs will come across "to have a business partner, or not to have a business partner."…
- The Customer Isn't ALWAYS Right But Sometimes They Are | Why You Need A Customer Service Manager To Scale Your Short Term Real Estate Business · 8 min · Season 1 Episode 678In this episode of Cashflow Diary, host J Massey, speaks with a group of coaching clients about the importance of having a customer service manager to scale your short term real…
- Technology Has And Will Continue To Change The Short Term Real Estate Industry · 8 min · Season 1 Episode 677In this episode of Cashflow Diary, host J. Massey, speaks with a group of coaching clients about technology and its impact on the short term real estate industry. Advancements in…
- How To Talk About Money Without Feeling Uncomfortable · 7 min · Season 1 Episode 676In this episode of Cashflow Diary, host, J.Massey, discusses how you can talk about money without feeling uncomfortable during the conversation. Talking about money makes many…
- How To Measure Your Financial Progress In The Short Term Real Estate Industry · 11 min · Season 1 Episode 675On this episode of Cashflow Diary, host, J. Massey, discusses why and how you must measure your financial progress when working in the short-term real estate industry…
- Should You Invest In A Cash Flow Business Or Focus More On Your Short-Term Real Estate Empire · 15 min · Season 1 Episode 674As you grow your short-term real estate empire, you will come to a crossroads. Should you invest in a cash-flow business, or should you focus on growing your business? This…
- You Need To Offer Storage In Your Short Term Rental Unit · 11 min · Season 1 Episode 673When renting out a short term, you need to acknowledge that your tenants are there for different reasons and lengths of stay. No two tenants are alike and neither is how much…
- Keeping Your Cool | What To Do With Unruly Tenant's And Landlords · 17 min · Season 1 Episode 672When you are building your short-term rental empire, you will work alongside many tenants. As a result, various scenarios will arise that will need creative problem solving…
- How To Turn Your Short-Term Renter Into A Repeat Customer · 12 min · Season 1 Episode 671When customers rent one of your short-term rentals, you want to do everything you can to keep them coming back as repeat customers. In this Q+A with coaching clients, I answer…
- How To Set Your Short Term Rental Apart From A Hotel · 12 min · Season 1 Episode 670The ability to stand out, and offer your business something different can help you run a successful short-term rental business. During a coaching call with clients, we discuss…
- The Reddit GameStop Short Sell Saga Explained · 7 min · Season 1 Episode 669During a recent coaching session with my clients, they had questions about the Reddit GameStop Saga that was so heavily covered in the media. I explain how short sells and the…
- What To Do When The Customer Leaves A Bad Review · 14 min · Season 1 Episode 668Every short-term rental owner is familiar with the feeling of being scratched if a guest writes bad reviews about their property. It's disheartening, but it's also normal. No…
- The Lay Out Of Your Unit Is More Important Than The Size Of The Unit · 14 min · Season 1 Episode 667When renting out a part of your property, the layout is everything. Setting up your unit can make the difference between having it booked for the whole season or being empty for…
- Nightmare Tenants And How To Deal With Them With Out Losing Your Cool · 15 min · Season 1 Episode 666Nightmare tenants. Unexpected maintenance requests. Confrontations with other hosts, or sometimes your landlords. Dealing with these conflicts is unavoidable, and to survive in…
- Working With Property Managers To Help You Build Your Real Estate Empire · 13 min · Season 1 Episode 665When you scale up your real estate empire and acquire multiple properties, hiring a property manager is essential to oversee the day-to-day operations of your investment…
- All The Pieces Matter | How The Interconnectivity Of The Global Market Can Affect How You Build Your Short Term Rental Empire | feat. Earl Powell · 11 min · Season 1 Episode 664On today’s episode, I am joined by Earl Powell and we are talking about the interconnectivity of everything that goes into building your short term rental empire. We also chat…
- Insurance: Can't Live With It And Can't Run Your Own Short Term Rental Empire Without It · 12 min · Season 1 Episode 663Knowing and understanding the nuances of insurance is essential to building your short-term real estate empire. Not surprisingly, questions about insurance are some of the most…
- How To Secure Capital To Grow Your Short Term Real Estate Empire · 15 min · Season 1 Episode 662Securing capital for your short-term real estate industry is one of the most frequently asked questions I receive when speaking with students and coaching clients. In today’s…
- How Inflation Has An Affect On The Short Term Real Esate Industry · 8 min · Season 1 Episode 661As inflation has been a topic of discussion lately, we will examine the impact of inflation on your growing real estate empire in today's episode. In this episode, we will…
- How The Short Term Rental Could Be Your Golden Ticket To Financial Freedom · 16 min · Season 1 Episode 660While there are no shortcuts to wealth - hard work, and determination in renting out your Short Term Real Estate could be your golden ticket to financial freedom. When building…
- You Don't Have To Go Home, But You Can't Stay Here | How To Decline Your Short Term Rental Services · 10 min · Season 1 Episode 659During coaching sessions with my clients, I frequently get asked questions about the day-to-day operations of running a short term rental business. For example, how to decline…
