629 episodes

J. Massey, real estate investor, entrepreneur, sales coach, instructor, master facilitator of Robert Kiyosaki’s CASHFLOW™ 101 games and creator of Cashflow™ Diary, offers free training courses for new and experienced investors.

Break through the clutter of learning real estate and business investing and become a successful entrepreneur. Listen to beneficial strategies to improve your skills in prospecting, placing offers, closing deals, buying, selling, wholesaling, fix & Flips, rehabs and much more. By way of Cashflow™ Diary, J. Massey basically gives away current industry strategies by simply teaching what he does daily as a real estate practitioner.

Start Learning For Free Today.

Cashflow Diary‪™‬ J. Massey

    • Business
    • 4.8 • 199 Ratings

J. Massey, real estate investor, entrepreneur, sales coach, instructor, master facilitator of Robert Kiyosaki’s CASHFLOW™ 101 games and creator of Cashflow™ Diary, offers free training courses for new and experienced investors.

Break through the clutter of learning real estate and business investing and become a successful entrepreneur. Listen to beneficial strategies to improve your skills in prospecting, placing offers, closing deals, buying, selling, wholesaling, fix & Flips, rehabs and much more. By way of Cashflow™ Diary, J. Massey basically gives away current industry strategies by simply teaching what he does daily as a real estate practitioner.

Start Learning For Free Today.

    How To Perfect Your Morning Routine To Maximize Your Daily Business Success 

    How To Perfect Your Morning Routine To Maximize Your Daily Business Success 

    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 self-care routines look like in this Clubhouse chat!


    In this episode, we will discuss:


    The 5 main categories of my morning routine  How you can train for your business like an athlete trains for their sport  Why listening to what your body needs is important to overall success 




    Subscribe To The Show

    Apple Podcasts | Spotify | Youtube



    Connect with J. Massey and the Cashflow Diary™

    Facebook | Instagram | LinkedIn | Clubhouse | TikTok



    Read the latest Cashflow Diary article: www.cashflowdiary.com/how-owner-financing-can-help-keep-your-real-estate-investing-dreams-alive



    About Cashflow Diary™

    J. 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.


    How To Perfect Your Morning Routine To Maximize Your Daily Business Success 

    • 1 hr 1 min
    Understanding Discretionary Income, Managing Financial Expectations & Tips For Hard Times (Explicit)

    Understanding Discretionary Income, Managing Financial Expectations & Tips For Hard Times (Explicit)

    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 an explicit conversation among friends - so it's best to listen to this episode with headphones on because this is not family or work-friendly.

    In this episode, we will discuss:

    What discretionary income is How to decipher what is discretionary and what is a necessity J’s personal stories of how he navigated homelessness and living without a car

    Subscribe to the Cashflow Diary™ podcast on Apple Podcasts: https://podcasts.apple.com/us/podcast/cashflow-diary/id623140540 

    Subscribe to the Cashflow Diary™ podcast on Spotify: https://open.spotify.com/show/3iJetWgP5D7lGQ03gsX6yt?si=XjUp-iA6QoObPESLAAWxOA 

    Subscribe to the Cashflow Diary™ YouTube channel: https://www.youtube.com/user/CashFlowDiary 


    Connect with J. Massey and the Cashflow Diary™ team via:

    Facebook: https://www.facebook.com/CashflowDiary 

    Instagram: https://www.instagram.com/cashflowdiary/ 

    LinkedIn: https://www.linkedin.com/company/cashflow-diary-with-j.-massey/ 

    TikTok: https://www.tiktok.com/@cashflowdiary 


    Join the Cashflow Cartel group on Clubhouse! https://www.clubhouse.com/club/the-cashflowdiary-cartel


    Read our latest blog – How To Analyze A Multifamily Home Real Estate Deal & Present It To An Investor

    Take a shortcut to short-term rental mastery and build the lifestyle and income of your dreams. Get the Short Term Rental Blueprint Video Course for absolutely FREE: https://cashflowdiary.com/blueprint/


    About Cashflow Diary

    J. 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.

    • 1 hr 7 min
    Tips On Investing Your Retirement Accounts | feat. Mat Sorenson

    Tips On Investing Your Retirement Accounts | feat. Mat Sorenson

    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 questions today through our Clubhouse interview with Mat Sorenson. 


    In this episode, we will discuss:


    What a self-directed IRA is and why people don’t want you to do it How you can further invest your retirement accounts  How you can self-direct a HSA for tax deductions 

    Mat Sorenson is an attorney, partner at KKOS Lawyers, and the CEO of Directed IRA. He’s the celebrated author of the best-selling book Self-Directed IRA, a top podcast host, and a self-directed retirement investor. 



    Subscribe to the Cashflow Diary™ podcast on Apple Podcasts: https://podcasts.apple.com/us/podcast/cashflow-diary/id623140540 


    Subscribe to the Cashflow Diary™ podcast on Spotify: https://open.spotify.com/show/3iJetWgP5D7lGQ03gsX6yt?si=XjUp-iA6QoObPESLAAWxOA 


    Subscribe to the Cashflow Diary™ YouTube channel: https://www.youtube.com/user/CashFlowDiary 



    Connect with J. Massey and the Cashflow Diary™ team via:


    Facebook: https://www.facebook.com/CashflowDiary 


    Instagram: https://www.instagram.com/cashflowdiary/ 


    LinkedIn: https://www.linkedin.com/company/cashflow-diary-with-j.-massey/ 


    TikTok: https://www.tiktok.com/@cashflowdiary 



    Join the Cashflow Cartel group on Clubhouse! https://www.clubhouse.com/club/the-cashflowdiary-cartel



    About Cashflow Diary™


    J. 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.


    Tips On Investing Your Retirement Accounts | feat. Mat Sorenson

    • 1 hr 15 min
    Financial Freedom and Creating Generational Wealth | feat. Shawn Ackerman

    Financial Freedom and Creating Generational Wealth | feat. Shawn Ackerman

    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 will discuss:


    How Shawn Ackerman went from the inner city of Brooklyn, NY to creating a multi-million dollar business through real estate investing The pros and cons of owning almost 100 short term rental properties  How to create generational wealth for your family


    Shawn Ackerman's Bio:


    Over the years I have learned some key life principles.  Some of which are; trading time for money is not a long term nor sustainable path to building wealth.  Passive income versus active income is  important for maintaining wealth with the possibility of minimal time sacrifice.


    I believe my purpose in life is to impart these key principles along with the wealth of knowledge I've obtained of buy and hold real estate investing.  I am very excited to share my knowledge to all of those eager to learn, grow and invest in their future.


    Ikeptit Real Estate, LLC is a Real Estate holding and Real Estate consulting company. We specialize in residential investment property acquisition and performance. We operate a "Learn Key" business in the Mid-Western part of the United States.  Our company is dedicated to working with out of state investors looking for cash flow with low cost and hassle free entry into Milwaukee WI real estate market. We are not a "Turn-Key" company, we are not rehabbers we are the investor investor!!!


    ​We provide REI consultation/Mentorship to new real estate investors looking to earn passive income through multiple real estate investing strategies.  ​​


    "Our mission is to provide  the best quality, low-cost, Clean and safe rental properties and real estate consultation/mentorship in the United States Of America. We strive to bring the best value to real estate investors."  


    Connect with Shawn Ackerman:


    Website: https://www.ikeptitrealestatellc.com/


    Facebook: https://www.facebook.com/stackermen/


    Instagram: http://instagram.com/ikeptit_real_estate


    Subscribe to the Cashflow Diary™ podcast on Apple Podcasts: https://podcasts.apple.com/us/podcast/cashflow-diary/id623140540 


    Subscribe to the Cashflow Diary™ podcast on Spotify: https://open.spotify.com/show/3iJetWgP5D7lGQ03gsX6yt?si=XjUp-iA6QoObPESLAAWxOA 


    Subscribe to the Cashflow Diary™ YouTube channel: https://www.youtube.com/user/CashFlowDiary 



    Connect with J. Massey and the Cashflow Diary™ team via:


    Facebook: https://www.facebook.com/CashflowDiary 


    Instagram: https://www.instagram.com/cashflowdiary/ 


    LinkedIn: https://www.linkedin.com/company/cashflow-diary-with-j.-massey/ 


    TikTok: https://www.tiktok.com/@cashflowdiary 



    Join the Cashflow Cartel group on Clubhouse! https://www.clubhouse.com/club/the-cashflowdiary-cartel



    Read our latest blog - How To Get Your Landlord To Say “Yes” To The Airbnb Business You’re Considering: https://cashflowdiary.com/blog/how-to-get-your-landlord-to-say-yes-to-the-airbnb-business-youre-considering/


    Take a shortcut to short term rental mastery and build the lifestyle and income of your dreams. Get the Short Term Rental Blueprint Video Course for absolutely FREE: https://cas

    • 1 hr 10 min
    Introducing Season Re-Deux Of The Cashflow Diary Podcast

    Introducing Season Re-Deux Of The Cashflow Diary Podcast

    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 and connect with you all on a deeper level than ever before.  Let's get started on the Season Re-Deux of the Cashflow Diary Podcast


    In this episode, we will discuss:


    Why I took a break from producing podcast episodes The changes in both my personal and professional life that have occurred since we last spoke  The various investments that I’ve made over the last couple of years  How connecting on the app Clubhouse will allow me to consistently serve you better


    Subscribe to the Cashflow Diary™ podcast on Apple Podcasts: https://podcasts.apple.com/us/podcast/cashflow-diary/id623140540 


    Subscribe to the Cashflow Diary™ podcast on Spotify: https://open.spotify.com/show/3iJetWgP5D7lGQ03gsX6yt?si=XjUp-iA6QoObPESLAAWxOA 


    Subscribe to the Cashflow Diary™ YouTube channel: https://www.youtube.com/user/CashFlowDiary 



    Connect with J. Massey and the Cashflow Diary™ team via:


    Facebook: https://www.facebook.com/CashflowDiary 


    Instagram: https://www.instagram.com/cashflowdiary/ 


    LinkedIn: https://www.linkedin.com/company/cashflow-diary-with-j.-massey/ 


    TikTok: https://www.tiktok.com/@cashflowdiary 



    Join the Cashflow Cartel group on Clubhouse! https://www.clubhouse.com/club/the-cashflowdiary-cartel



    Read our latest blog - How To Get Your Landlord To Say “Yes” To The Airbnb Business You’re Considering: https://cashflowdiary.com/blog/how-to-get-your-landlord-to-say-yes-to-the-airbnb-business-youre-considering/


    Take a shortcut to short term rental mastery and build the lifestyle and income of your dreams. Get the Short Term Rental Blueprint Video Course for absolutely FREE: https://cashflowdiary.com/blueprint/

    • 12 min
    609 Troy Underwood

    609 Troy Underwood

    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 title system for financial institutions, which was later sold for $106 million. His healthcare venture, benefitsCONNECT, innovated healthcare benefits administration and resulted in a highly successful acquisition. His new book is How to Launch Your Side Hustle: Start and Scale a Business with Minimal Capital. Learn more at troyrunderwood.com. 
    Podcast Highlights Who is Troy Underwood?  Troy considers himself a necessity entrepreneur and has been doing the entrepreneurial thing since elementary school. Troy has sold all sorts of products including greeting cards, seeds, and computers. Whatever the opportunity was, Troy was willing to take advantage of it.
    For the average entrepreneurial minded person, the problem is having too many ideas. They need to take these ideas and pick one, then execute, and then when they get bored they have to keep pushing instead of flipping to the next one. Ideas are everywhere, execution, perseverance, and discipline is what’s rare. Even a mediocre idea, when executed well, can work out.
    Troy’s original plan was to become a doctor, not an entrepreneur. It wasn’t until Troy took an economics course on a dare that he realized that he loved the study of economics and completely switched tracks. He kept up his involvement in computers and software development, and found himself in the right place and the right time to offer a solution that jump-started a business. 
    Is now the right time to start something? Now may actually be a great time to start a new business, especially for those who have been laid off with nothing to go back to. If you’ve been thinking about it for a while and you have an idea, if everything else is relatively stable, now could be the right time to give it a shot.
    Being an entrepreneur isn’t an exact science, you just have to take the cards you're dealt and play them the best you can.
    If you’re someone who craves certainty and security, don’t be an entrepreneur. You are able to mitigate some of that risk by being a business owner instead of an entrepreneur, for example opening a franchise which has a higher rate of success. If you’re looking for certainty, you’re not going to find it in your own business. 
    Who should be an entrepreneur? Creative thinkers and risk takers are the people who should be entrepreneurs. There is a lot of risk and opportunity cost in building a business and you need to be okay with taking that on. 
    If you’re driven by necessity you are going to have much more motivation to push through the difficult times and figure out solutions to complicated problems that can keep a business running.
    Why a side hustle instead doing something BIG? Troy compares a side hustle to a rocket ship launch. It’s not just about keeping a side hustle, it’s about building something that you know will be big eventually, something that replaces your full time job in time and is worth investing in.
    For Troy, it’s not about having a second part time job to make some extra money. It’s about building something that can make a big impact over time.
    What is the self assessment? Being an entrepreneur is like climbing Mount Everest, it’s not something you do on a casual whim. You need to be mentally and physically prepared for both endeavors and take stock of your temperament and if being an entrepreneur is really for you. Troy spends just as much time talking people out of being an entrepreneur as he does strategizing how to launch their side hustle. 
    Even if you think you’re unprepared, there is a point where you need to stop reading and start doing.
    Reference: How to Launch Your Side Hustle: Start and Scale a Business with Minimal Capital, Troy Underwood
    Troy’s Takeaway You have to be all in and make sure you also have your partner’s buy in as well. Th

    • 37 min

Customer Reviews

4.8 out of 5
199 Ratings

199 Ratings

malfoxley ,

Great show!

J., host of theCashflow Diary podcast, highlights all aspects of investing and more in this can’t miss podcast! The host and expert guests offer insightful advice and information that is helpful to anyone that listens!

MATT@CYB ,

Amazing Content!

J is truly an inpirational and educated man! He dives deep into the life of an entreprenuer and dsicusses how handling finances in the business realm is a very important asset to society! Highly recommend 5/5!

S H Elliott ,

So insightful!

So motivational, great guests and very relatable topics especially for aspiring entrepreneurs. and investors.

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