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 clie...
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Nov 13, 2026 · 10:47
AI disclosure: This episode is narrated by an AI-generated voice. You've got a day job, and a guest is in the driveway early. So you leave work, drive across town and hand over a…
Nov 10, 2026 · 9:58
AI disclosure: This episode is narrated by an AI-generated voice. "Put it in an LLC." You'll hear it from a cousin, a podcast and a Facebook group in the same week, and none of…
Nov 6, 2026 · 9:51
AI disclosure: This episode is narrated by an AI-generated voice. Checkout at eleven, check-in at four. That five hour window shapes your reviews, and on most turnover days the…
Nov 3, 2026 · 9:46
AI disclosure: This episode is narrated by an AI-generated voice. Airbnb says most hosts on its single fee structure pay 15.5% of every booking. The common advice is to build…
Oct 30, 2026 · 9:01
AI disclosure: This episode is narrated by an AI-generated voice. Somebody tells you, "You can't do that here. They banned it." Maybe they're right, and maybe they read a…
Oct 27, 2026 · 8:30
AI disclosure: This episode is narrated by an AI-generated voice. Maybe you've said it out loud. "I'm just not a money person." J. has a different explanation. Every person goes…
Oct 23, 2026 · 8:25
AI disclosure: This episode is narrated by an AI-generated voice. Counting from Friday, October 23, there are 69 days left in the year. Maybe you said this would be the year you…
Oct 20, 2026 · 8:21
AI disclosure: This episode is narrated by an AI-generated voice. In August, 1.6 million people in the U.S. were laid off or let go, by the Bureau of Labor Statistics' count.…
Oct 15, 2026 · 6:51
AI disclosure: This episode is narrated by an AI-generated voice. Your Airbnb minimum stay can turn guests away while you sleep. Sixteen people asked about one of our own…
Oct 14, 2026 · 10:33
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.…
Apr 20, 2026 · 5:43
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.…
Apr 12, 2026 · 9:00
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…
Apr 11, 2026 · 12:03
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…
May 2, 2025 · 5:42
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…
Apr 9, 2025 · 17:04
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…
Mar 21, 2025 · 9:03
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…
Mar 14, 2025 · 14:12
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…
Apr 7, 2023 · 22:43
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…
Apr 4, 2023 · 23:59
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…
Mar 31, 2023 · 10:33
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…
Mar 28, 2023 · 15:09
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…
Mar 24, 2023 · 9:38
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.…
Mar 21, 2023 · 10:59
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…
Mar 17, 2023 · 15:32
In 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…
Mar 14, 2023 · 7:09
In 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…
Mar 10, 2023 · 8:15
In 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,…
Mar 7, 2023 · 13:58
In 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…
Mar 3, 2023 · 7:18
In 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…
Feb 28, 2023 · 8:16
In 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…
Feb 24, 2023 · 10:07
On 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."…
Feb 21, 2023 · 7:46
In 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…
Feb 17, 2023 · 7:44
In 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…
Feb 14, 2023 · 6:35
In 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…
Feb 10, 2023 · 10:39
On 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.…
Feb 7, 2023 · 15:29
As 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…
Feb 3, 2023 · 10:39
When 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…
Jan 31, 2023 · 16:56
When 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.…
Jan 27, 2023 · 11:44
When 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…
Jan 24, 2023 · 12:19
The 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…
Jan 20, 2023 · 7:27
During 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…
Jan 17, 2023 · 14:08
Every 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…
Jan 13, 2023 · 13:34
When 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…
Jan 10, 2023 · 14:43
Nightmare tenants. Unexpected maintenance requests. Confrontations with other hosts, or sometimes your landlords. Dealing with these conflicts is unavoidable, and to survive in…
Jan 6, 2023 · 13:13
When 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…
Jan 3, 2023 · 11:13
On 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…
Dec 30, 2022 · 11:38
Knowing 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…
Dec 27, 2022 · 15:13
Securing 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…
Dec 23, 2022 · 7:47
As 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…
Dec 20, 2022 · 16:07
While 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…
Dec 16, 2022 · 9:51
During 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…
Dec 13, 2022 · 9:06
During coaching sessions with my clients, I frequently get asked questions about purchasing investment properties in a short sale. In today's episode, I answer questions and…
Dec 9, 2022 · 7:57
When running a short term rental empire, the location of your property is key. Most people think having a property near the airport is the best location, but it's more…
Dec 6, 2022 · 9:12
One of the best ways to find new customers is by advertising online. During a call with students, I was asked for advice on making direct bookings through digital marketing. I…
Dec 2, 2022 · 6:09
Short term rental industry creates a lot of taxable income, which keeping track and reporting your income to the I.R.S is crucial. During our recent coaching session, I shared…
Nov 29, 2022 · 6:29
The price of real estate increases in tandem with the inflation rate. Housing and other real estate assets generally rise when inflation increases. In today's episode, we will…
Nov 25, 2022 · 8:54
Rent is your biggest expense when it comes to building your short-term real estate empire. So it is crucial that you answer and understand certain questions, such as how you know…
Nov 22, 2022 · 8:48
Creating your network is the best way to build your real estate business and not have to be dependent on an algorithm. In today's episode, I will share tips and techniques on the…
Nov 18, 2022 · 10:42
Developing a pricing strategy for your Airbnb rentals is one of the most challenging parts of building your short term rental empire. During a question and answer session with…
Nov 15, 2022 · 11:31
While building your short term rental empire, there are three phases your business will go through. Knowing what to expect will give you time to plan and make informed decisions.…
Nov 11, 2022 · 8:42
As your short term rental empire grows, you need to hire more contractors, vendors and employees. It is important that you classify them accordingly to ensure your business runs…
Nov 8, 2022 · 15:15
When you're growing your real estate empire, there is a scenario where your business will grow too fast. During a conversation with a coaching client, I shared advice and…
Nov 4, 2022 · 10:28
One misconception I hear often is that you need to own property to start a short term rental business. In today's episode, I dispel that misconception and will teach you the…
Nov 1, 2022 · 12:56
Successfully running a short term rental business requires effective communication with your team. During a Q+A session with a student, I was asked what process I use to…
Oct 28, 2022 · 11:43
Starting an Airbnb hosting business is full of rewards and challenges, but is it right for you? I will help you make that decision by sharing everything you need to get started,…
Oct 25, 2022 · 22:13
During coaching sessions with my clients, I frequently get asked questions about purchasing multi family investment properties. In today's episode, I answer questions on…
Oct 21, 2022 · 10:40
The short-term rental industry has existed since the civil war.. Unfortunately, I frequently hear in the media the need for short term rentals has stalled and that this "new"…
Oct 18, 2022 · 13:45
During coaching sessions with my clients, I frequently get asked, "how do I analyze a real estate deal for multi family Tri-Plex homes?" In today's episode, I will teach you how…
Oct 14, 2022 · 9:59
During coaching sessions with my clients, I frequently get asked, "how do I analyze a real estate deal for multi family homes?" In today's episode, I will teach you how to use…
Oct 11, 2022 · 24:29
One question I get asked often is how do I analyze real estate deals? In today's episode, I will provide a step-by-step list of how to use “The Profit Analysis Quadrant” for…
Oct 6, 2022 · 10:10
Regarding real estate investments, one of the questions I get frequently asked is whether I should buy a single-family or multi-family home. In today's episode, I take listeners'…
Oct 4, 2022 · 10:09
Once you start your own Airbnb business, you will figure out how to find capital in order to grow. There are eight steps to find capital. By learning and utilizing these steps to…
Sep 30, 2022 · 7:28
Property ratings in Airbnb are influenced by many factors such as cleanliness and service. Among the critical features of your, Airbnb is how you set it up, furnish, and stylize…
Sep 27, 2022 · 7:58
With all the evidence it makes sense to me why you would want to start your own Airbnb business. I have had the privilege of welcoming more than 3000 guests and 100 reservations.…
Sep 23, 2022 · 9:33
How do you get a landlord to say yes to your Airbnb business? They could just do it themselves and make more money or they could even work with a property manager. But, how you…
Sep 20, 2022 · 10:48
Why is everyone talking about generating passive income? I am going to break down the different types of income, do a deep dive into passive income, and teach you how to make all…
Sep 16, 2022 · 9:31
You don’t need to have any experience in real estate to start an Airbnb business. I will give you three steps to take in order to begin your short-term rental journey. In this…
Aug 19, 2022 · 54:09
Short-term rental investment success always starts with the property that's in your backyard and close to you. But when you start spreading out too soon, too fast. It's too hard.…
Aug 16, 2022 · 1:14:07
Have you experienced some unpredicted hiccups after starting your short-term rental business? That’s totally normal. I am here to address every question and concern you have with…
Aug 5, 2022 · 1:01:18
What does a morning routine look like for someone whose main source of income comes from passive revenue streams? Well luckily for you, I’ll be sharing what my mornings and…
Aug 4, 2022 · 1:08:00
Do you find yourself wondering where to draw the line with discretionary income? Well, all of your questions will be answered in this Clubhouse group conversation. Also, this is…
Jul 30, 2022 · 1:15:16
We’ve always been told that investing your retirement account is one of the best things you can do… but what exactly is the best way to do it? We are here to answer all of your…
Jul 22, 2022 · 1:10:56
Are you ready to ditch your 9-5 and enter into financial freedom? Our interview with Shawn Ackerman will show you exactly how you can make that your reality In this episode, we…
Jul 19, 2022 · 12:50
I know… you’re probably thinking, “Where has J been? Why hasn’t he put out a podcast episode in 2 years?” Hey – I missed you too. I’m fired up to bring this podcast back to life…
May 11, 2020 · 37:19
Troy R. Underwood is an industry disruptor. Part technologist, part economist, and all innovator, he revolutionized the motor vehicle industry with the nation’s first electronic…
May 7, 2020 · 37:01
Mark Willis, is a CERTIFIED FINANCIAL PLANNER™, a #1 Best Selling Author and the owner of Lake Growth Financial Services, a financial firm in Chicago, Illinois. Over the years,…
Apr 23, 2020 · 52:22
Stu Heinecke is the Hall of Fame “Father of Contact Marketing" and Founder/President of the Contact Marketing Agency and Cartoonlink, which helps sales teams break through using…
Apr 20, 2020 · 37:14
As founder of Money Ripples, host of The Chris Miles Money Show, and co-author of the book Entrepreneur on Fire, Chris Miles is a leading authority on quickly creating wealth by…
Apr 16, 2020 · 36:46
Kyle Stanley is the host of the Fearless Flipping podcast where he educates new hungry real estate investors about best practices for getting started. We flip the roles into…
Apr 13, 2020 · 46:19
Let me introduce you to Scott Smith, a new breed of real estate attorney with a great sense of humor and a gift for simplifying the complex. His Austin startup, Royal Legal…
Apr 9, 2020 · 45:58
With a diverse career crossing professional services, mining services, civil construction, manufacturing, industrial relations Jacqueline has used public speaking-centric…
Apr 2, 2020 · 36:54
Kyle Stanley is the host of the Fearless Flipping podcast where he educates new hungry real estate investors about best practices for getting started. Kyle is also a master with…
Mar 26, 2020 · 41:19
Chad Peterson is an expert business broker and the founder of Peterson Acquisitions, an award-winning M&A firm. Chad’s firm handles transactions in the $1 million to $25 million…
Mar 16, 2020 · 51:00
Annie Dickerson and Julie Lam are the co-founders and managing partners of Goodegg Investments, a premier real estate investing company that helps people learn about and invest…
Mar 12, 2020 · 54:29
Gina Bianchini is the Founder & CEO of Mighty Networks . Her mission at Mighty Networks is to usher in a new era of creative business built on community. Mighty serves “creators…
Mar 9, 2020 · 36:56
How do you house hack your way to financial freedom with hardly any money down? How do you build a best-in-class property management company? What is the best day to do a home…
Mar 5, 2020 · 45:29
We’re exploring the question that almost everybody considering short term rentals asks, how much money can you make with a short term rental unit? The answer may surprise you.…
Mar 2, 2020 · 2:01:38
You’ve tried reading a book and watching a video, you’ve also probably tried going to a couple conferences, and the trouble is that’s not enough for you to make transformational…
Feb 27, 2020 · 1:19:45
Humans don’t transform overnight. Most people can’t just read a book or watch a video and completely change their life immediately. You’re not going to be able to pick up a bunch…
Feb 24, 2020 · 2:25:00
How would it feel to earn an entire year’s salary in only one month? When you understand the power of a short term rental business and crunch the numbers involved, the path…
Feb 20, 2020 · 1:45:42
The short term rental industry is waiting for people like you who want to be professional operators delivering a high quality experience. The hardest way to do this business is…
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