Cashflow Diary™

J. Massey
  • 4.8 (200)
  • Investing
  • Weekly

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.

  1. 21h ago

    Is Airbnb Legal in My City? 4 Places to Check Before You Sign a Lease

    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 headline. J. doesn't tell you whether short-term rentals are allowed in your city, because the answer depends on your city's own code. He shows you how to find out for yourself, in four places, before you sign a lease. What you'll learn: Why the newspaper article, your realtor friend and the guy at the barbecue are not the ordinance The search J. uses to find the actual code (and why he looks for the .gov address) What to do when the city comes up empty (check the county) How to read an ordinance by going straight to the definitions, and the four things to look for after that: where, when, how and who How to call the planning or permit office with the section number in front of you, and why you ask for the answer in an email Where HOA rules live (the CC&Rs, bylaws, rules and amendments) and the words to look for Why the landlord's written permission comes before the lease signature A 10-minute homework: one city, one search, one definition, one number Timestamps: 00:00 'Is Airbnb legal in my city?' 00:54 The headline is not the ordinance 02:05 Place 1: the city or county code 03:12 Read the definitions first 04:29 Place 2: the planning or permit office 05:24 Place 3: the HOA 06:30 Place 4: the lease, and your homework 07:56 Diagnostic call and sign-off 08:40 AI voice note Want a second set of eyes on your situation and your numbers? Book your complimentary one-on-one diagnostic call: go.cashflowdiary.com/ep703-call Not ready for a call? Get the free Cashflow Diary newsletter: go.cashflowdiary.com/ep703-subscribe Sources: City of Austin Development Services, Short-Term Rentals page (austintexas.gov), for the "less than 30 consecutive days" definition. City of Newport Beach, Short-Term Rentals FAQ (newportbeachca.gov), on reviewing CC&Rs and following up with the HOA. Airbnb Help Center, "General info about hosting places to stay" (airbnb.com/help/article/1397), on leases, landlords, HOA rules and contract riders. J. Massey's own teaching from his courses and live trainings ("Did you read the ordinance?", the .gov search, the county-level example, going straight to the definitions, the order of landlord, disclosure, ordinance and lease). If this helped, rate the show on Apple Podcasts or Spotify. Narrated with J. Massey's licensed AI voice, built from his own recordings. Educational content, not financial, legal or tax advice. Rules differ by city, county and property; confirm with your local government and a local attorney. (00:00) - 'Is Airbnb legal in my city?' (00:53) - The headline is not the ordinance (02:05) - Place 1: the city or county code (03:11) - Read the definitions first (04:29) - Place 2: the planning or permit office (05:23) - Place 3: the HOA (06:30) - Place 4: the lease, and your homework (07:55) - Diagnostic call and sign-off (08:40) - AI voice note

    Is Airbnb Legal in My City? 4 Places to Check Before You Sign a Lease

  2. 3d ago

    Not a Money Person? You Can't Learn and Look Good at the Same Time

    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 through four levels to learn anything, whether it is a stick shift or the numbers on a rental, and the second level is supposed to feel uncomfortable. J. taught it this way in his Cashflow Foundation course. You can't learn and look good at the same time. What you'll learn: Why the person you are today isn't ready for the future you want yet, and why that's good news The four levels of learning, in plain English: you don't know what you don't know, you know you don't know, you know but have to concentrate, and the zone The three words that stop learning: "I know that" Why we stop asking questions somewhere between kindergarten and twelfth grade, and what a toddler learning to talk can teach you about money How the four levels show up when you start a rental business A 10-minute homework: one money topic you've avoided, your level, and one question to ask this week Timestamps: 00:00 'I'm not a money person' 00:55 Who you are today vs. what you want 01:45 Level 1: you don't know what you don't know 02:41 Level 2: you can't learn and look good 04:02 Levels 3 and 4: from concentration to the zone 05:02 The four levels in a rental business 06:35 Your 10-minute homework: one question 07:24 Diagnostic call and sign-off 08:09 AI voice note Want a second set of eyes on your situation and your numbers? Book your complimentary one-on-one diagnostic call: go.cashflowdiary.com/ep702-call Not ready for a call? Get the free Cashflow Diary newsletter: go.cashflowdiary.com/ep702-subscribe Sources: J. Massey's own teaching. Cashflow Foundation course ("the four levels of learning," the photography and stick-shift examples, "I know that," the bedtime-story questions, decide means to cut off), a 2020 live training (the toddler learning to talk), a 2023 mastermind session ("an addiction to looking good"), and a 2023 member webinar ("you and I cannot out-earn our personal growth"). If this helped, rate the show on Apple Podcasts or Spotify. Narrated with J. Massey's licensed AI voice, built from his own recordings. Educational content, not financial advice. Results not typical; client details changed. (00:00) - 'I'm not a money person' (00:55) - Who you are today vs. what you want (01:45) - Level 1: you don't know what you don't know (02:40) - Level 2: you can't learn and look good (04:02) - Levels 3 and 4: from concentration to the zone (05:02) - The four levels in a rental business (06:34) - Your 10-minute homework: one question (07:24) - Diagnostic call and sign-off (08:09) - AI voice note

    Not a Money Person? You Can't Learn and Look Good at the Same Time

  3. Oct 23

    69 Days Left: Decide, or Let Time Decide for You

    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 got ahead of the bills or started something of your own. J. taught it this way in his Cashflow Foundation course back in 2013. We don't like making decisions, so we let time make them for us, and time will make decisions for you when you fail to take control of it. This episode covers why we wait (the pain gap between where you are and what you want), why staying started is harder than getting started, and what deciding looks like inside a rental business. What you'll learn: How a default becomes a decision, and why next October looks like this one if you never touch the settings The pain gap: wait for your reality to decline, or purposely increase your dream Three questions to write in the first person before you start A result-based work day, and how it applies to numbers and conversations in a rental business A 10-minute homework: one thing by December 31, the next step, and your daily result Timestamps: 00:00 69 days left in the year 00:55 Let time decide, or decide yourself 01:56 The pain gap: why we wait 03:04 Three questions to write down 03:55 Getting started vs. staying started 04:56 Defaults in a rental business 06:15 Your 10-minute homework: the next step 07:13 Diagnostic call and sign-off 08:04 AI voice note Want a second set of eyes on your situation and your numbers? Book your complimentary one-on-one diagnostic call: go.cashflowdiary.com/ep701-call Not ready for a call? Get the free Cashflow Diary newsletter: go.cashflowdiary.com/ep701-subscribe Sources: J. Massey's own teaching, Cashflow Foundation course (2013: "now o'clock," letting time make decisions, the pain gap, the three questions, the result-based work day), STR challenge and procrastination trainings (2022). Jim Rohn quote: "Don't wish it were easier. Wish you were better." If this helped, rate the show on Apple Podcasts or Spotify. Narrated with J. Massey's licensed AI voice, built from his own recordings. Educational content, not financial advice. Results not typical; client details changed. (00:00) - 69 days left in the year (00:54) - Let time decide, or decide yourself (01:55) - The pain gap: why we wait (03:04) - Three questions to write down (03:54) - Getting started vs. staying started (04:55) - Defaults in a rental business (06:15) - Your 10-minute homework: the next step (07:12) - Diagnostic call and sign-off (08:04) - AI voice note

    69 Days Left: Decide, or Let Time Decide for You

  4. Oct 20

    Job Security: Why One Paycheck Is a Single Point of Failure

    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. That was an ordinary month. J. has asked one question in his trainings for years. If your job was gone tomorrow, what would happen? If the answer is "everything stops," you are running your household on a single point of failure. This episode looks at that idea in two places. First at home, where a backup plan and a fail-safe are different things. Then inside a rental business, where it's easy to escape one single point of failure and build five new ones. What you'll learn: The difference between a backup plan (you start it after the break) and a fail-safe (it's already running) Streams of income vs. piles of cash, and why savings alone is a backup plan Five single points of failure in a rental business: booking sources, cleaners, repairs, what lives in your head, and guest types A 30-minute single-point-of-failure audit you can do with one sheet of paper Timestamps: 00:00 1.6 million layoffs in one month 01:02 Backup plan vs. fail-safe 02:00 Streams of income vs. piles of cash 02:57 Why this is personal for me 03:55 Rental weak spots 1-2: booking sources and cleaners 05:10 Rental weak spots 3-5: repairs, notes, guest types 06:22 Your 30-minute single-point-of-failure audit 07:19 Diagnostic call and sign-off 08:00 AI voice note Want a second set of eyes on your setup and your numbers? Book your complimentary one-on-one diagnostic call: go.cashflowdiary.com/ep700-call Not ready for a call? Get the free Cashflow Diary newsletter: go.cashflowdiary.com/ep700-subscribe Source: U.S. Bureau of Labor Statistics, Job Openings and Labor Turnover Survey, August 2026 (released September 29, 2026): layoffs and discharges 1.6 million, rate 1.0 percent. If this helped, rate the show on Apple Podcasts or Spotify. Narrated with J. Massey's licensed AI voice, built from his own recordings. Educational content, not financial advice. Results not typical; client details changed. (00:00) - 1.6 million layoffs in one month (01:02) - Backup plan vs. fail-safe (02:00) - Streams of income vs. piles of cash (02:57) - Why this is personal for me (03:55) - Rental weak spots 1-2: booking sources and cleaners (05:10) - Rental weak spots 3-5: repairs, notes, guest types (06:21) - Your 30-minute single-point-of-failure audit (07:19) - Diagnostic call and sign-off (07:59) - AI voice note

    Job Security: Why One Paycheck Is a Single Point of Failure

  5. Oct 15

    Airbnb Minimum Stay: The Setting That Turns Guests Away While You Sleep

    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 properties and never booked. Sorted by reason, they came down to two, and one cost nothing to fix. What you'll learn: How a minimum-night rule turns guests away without telling you Why your booking rules are a sales team you never interviewed How an offer you can deliver, but never showed, costs you bookings The four things a sellable offer needs, in order: photos, a defined experience, a price, delivery confidence How to build your photographer's shot list from guest questions A two-hour lost-inquiry audit you can run this week Timestamps: 00:00 Sixteen lost inquiries, two reasons 00:51 Reason one: a rule we made up 01:34 Your booking rules are a sales team 01:59 Reason two: an offer we never showed 02:45 Your inquiry log is your product roadmap 03:47 Shot lists and good-enough photos 04:34 Your two-hour lost-inquiry audit 05:51 Diagnostic call and sign-off 06:30 AI voice note Want a second set of eyes on your listing and your numbers? Book your complimentary one-on-one diagnostic call: cashflowdiary.com/diagnostic Resources: Get the Cashflow Diary newsletter: newsletter.cashflowdiary.com Notes, transcript and video for this episode: cashflowdiary.com/podcast/how-to-get-more-airbnb-bookings-read-your-lost-inquiries All episodes: cashflowdiary.com/podcast If this helped, rate the show on Apple Podcasts or Spotify. Narrated with J. Massey's licensed AI voice, built from his own recordings. Educational content, not financial advice. Results not typical; client details changed. (00:00) - Sixteen lost inquiries, two reasons (00:51) - Reason one: a rule we made up (01:34) - Your booking rules are a sales team (01:59) - Reason two: an offer we never showed (02:45) - Your inquiry log is your product roadmap (03:47) - Shot lists and good-enough photos (04:34) - Your two-hour lost-inquiry audit (05:51) - Diagnostic call and sign-off (06:30) - AI voice note

    Airbnb Minimum Stay: The Setting That Turns Guests Away While You Sleep

  6. Oct 14

    Is Airbnb Profitable? The $800-Per-Bedroom Test

    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 learn: Following one $115 booking through the fee chain Why property management is not hospitality management The four levers: leads × conversion × frequency × margin The $800-per-bedroom-per-month benchmark Three habits that cap experienced hosts: pricing below your own pricing tool, one-platform dependence, and giving away what guests would pay for Two tests to run on your numbers tonight Timestamps: 00:04 Making money for everyone but yourself 00:58 Case one: six years, zero profit 02:23 Property management is not hospitality management 03:26 The four levers: leads, conversion, frequency, margin 05:12 Case two: nine bedrooms, same pattern 05:36 The $800-per-bedroom benchmark 06:14 Three habits that cap experienced hosts 08:12 Every habit is a margin problem 08:46 Your two tests for tonight 09:48 Complimentary diagnostic call Want a second set of eyes on your numbers? Book your complimentary one-on-one diagnostic call: cashflowdiary.com/diagnostic Resources: Get the Cashflow Diary newsletter: newsletter.cashflowdiary.com All episodes: cashflowdiary.com/podcast Narrated with J. Massey's own licensed AI voice clone, from J.'s real client conversations and notes. Educational content, not financial advice. Results not typical; client details changed. (00:00) - Intro (00:04) - Making money for everyone but yourself (00:58) - Case one: six years, zero profit (02:23) - Property management is not hospitality management (03:26) - The four levers: leads, conversion, frequency, margin (05:12) - Case two: nine bedrooms, same pattern (05:36) - The $800-per-bedroom benchmark (06:14) - Three habits that cap experienced hosts (08:12) - Every habit is a margin problem (08:46) - Your two tests for tonight (09:48) - Complimentary diagnostic call (10:13) - About this episode's voice

  7. Apr 20

    Rental Property Cash Flow Calculator: How to Calculate It Before You Buy

    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 the order they matter. In This Episode: Why the "$2,000 rent minus $1,200 mortgage = $800 cash flow" math is almost always wrong The 8-line formula every rental property analysis needs How to calculate vacancy allowance, property management, taxes, insurance, repairs, and CapEx reserve What honest net cash flow looks like on a mid-market deal Why knowing the real numbers before you buy protects you through market corrections Key Takeaway: Cash flow is what keeps you solvent short-term. Run all 8 line items every time — even when it makes the deal look worse on paper. Get the full calculator walkthrough at cashflowdiary.com. Full Transcript: What's up, what's up, what's up — welcome back to the CashFlow Diary podcast. I'm J. Massey, and today we're talking about something that trips up almost every new investor I meet. Cash flow. More specifically — how to actually calculate it. Because here's what I see all the time: an investor brings me a deal, they're excited, the property cash flows five hundred dollars a month. And I sit down, I start asking questions, and five minutes later — we're at eighty dollars. Sometimes we're negative. And the investors are always surprised. They're not making arithmetic mistakes. They're leaving out entire expense categories. Categories that are absolutely going to show up once they own the property. The math doesn't lie. But incomplete math will. So today I'm walking you through the rental property cash flow calculator formula I actually use. Every line item. Real numbers. In the order they matter. Stay with me. Let's start with the basics. What is cash flow, really? Cash flow is what's left after every legitimate expense — and your mortgage payment — come out of your rent. Not appreciation. Not loan paydown. Not paper gains. Cash — the money that hits your bank account every month. This distinction matters more than people realize. A property can make money over ten years through appreciation while bleeding you three hundred dollars a month the entire time. Cash flow is what keeps you solvent in the short term. It's the difference between an investment that funds your life and one that slowly drains it. Now — the formula. Let's go line by line. Step one. Gross Rental Income. This is the full rent at one hundred percent occupancy. For a long-term rental, it's your monthly lease rate. Simple. Step two. Vacancy Allowance. Eight to ten percent, every time. No property stays fully occupied every month of every year. Tenant turnover happens. Lease-up periods happen. Slower months happen. Remove vacancy from your analysis to make the numbers look better, and you're just setting yourself up for a number that was always going to happen. Your Gross Effective Income equals your Gross Rental Income multiplied by ninety to ninety-two percent. That's your starting point for all expenses. Step three. Operating Expenses. This is where most deals collapse on paper — and this is where you have to be honest with yourself. Here's what goes in operating expenses: Property management — eight to twelve percent of gross rents. Even if you self-manage today, you need to model this. Property taxes — pull the actual number from the county assessor's office. Don't estimate. Insurance — landlord insurance for a single-family home typically runs twelve hundred to twenty-four hundred dollars per year. Repairs and maintenance — budget one percent of property value per year. Capital expenditures. CapEx. This is the one most investors skip. Roof. HVAC. Water heater. Appliances. Everything in that house is going to break eventually. Budget five to ten percent of gross rent per month into a reserve account. Not spending it — reserving it. Because the day your HVAC goes, you will be glad you did. Add all of that up and on a typical mid-market property you're looking at thirty-five to fifty percent of your gross rental income. Before you touch the mortgage. Step four. Debt Service. Principal and interest on your mortgage. This is not optional. Net cash flow equals Gross Effective Income minus total operating expenses minus debt service. On a property renting for two thousand dollars a month with a twelve hundred dollar mortgage payment — after you run the real numbers — honest net cash flow is somewhere between one hundred and three hundred fifty dollars per month on a well-analyzed deal. If you overpaid, it's negative. That's the deal. Here's why I'm sharing this with you today. Not to discourage you. Not to make real estate look hard. But because the investors who survive and scale are the ones who see deals clearly. When you know the real numbers before you buy, you can negotiate better. You can walk away from bad deals without regret. You can hold your properties through market corrections because you're not bleeding cash every month. The formula isn't complicated. What's hard is being disciplined enough to fill in every line, every time, even when it makes a deal look worse. I put together a full walkthrough of this formula — with real numbers and a real deal scenario — at cashflowdiary.com. The link is in the show notes. If this episode helped you think differently about how you analyze deals, I'd really appreciate a five-star review. It takes thirty seconds and it helps more investors find this show. Subscribe if you're not already — we drop new episodes every week. I'm J. Massey. Let's go build cash flow.

  8. Apr 12

    FIFA Just Canceled 70% of Its World Cup Hotel Blocks — Here's What That Actually Means

    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 signals you'll see all year. In this episode, J. breaks down exactly what happened, introduces you to a hotel industry concept called "The Wash," and shows you how to position your short-term rental business to capture the massive demand coming this summer. What You'll Learn What FIFA actually did — and why it's not bad news The hotel industry concept of "The Wash" and why it happens at every mega-event Why this wash is bigger than normal (first 48-team World Cup, 16 cities, 3 countries) The STR earnings opportunity: $156M projected host earnings, $1.21B in direct spending "Last man standing" pricing strategy — why patience beats early discounting 4 specific action steps to position your STR business for World Cup demand Key Numbers Vancouver: ~15,000 nightly bookings released (70-80% of original block) NYC hotel average: $583/night for World Cup dates Airbnb projecting 2.7 million guest nights Average host earnings: $3,000-$5,200 over tournament period Dallas leads: 9 matches, 307,000 projected Airbnb guest nights Sources Full article on CashFlowDiary.com 6ABC Philadelphia — FIFA Releases 2,000 Hotel Rooms WSB-TV Atlanta — FIFA Cancels Hotel Room Blocks Travel Weekly — World Cup Room Cancellations AirROI — World Cup Host Earnings Projections Subscribe to the CashFlowDiary newsletter: newsletter.cashflowdiary.com/welcome

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4.8
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About

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.

Information

  • Creator
    J. Massey
  • Years Active
    2013 - 2026
  • Episodes
    703
  • Rating
    Clean
  • Copyright
    © CashFlow Diary and West Egg Enterprises Inc 2013-2026
  • Show Website
    Cashflow Diary™

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