300 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.

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Cashflow Diary™ J. Massey

    • Investing

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.

    Thomas W. Jones: From Campus Revolutionary to Powerful Financial Services Leader

    Thomas W. Jones: From Campus Revolutionary to Powerful Financial Services Leader

    Thomas W. Jones is the Former Vice Chairman, President & COO at TIAA-CREF, the largest pension system in the country. He was the former Vice Chairman of Travelers, the Federal Reserve Bank of New York, and Freddie Mac, and the Former Chairman & CEO of Smith Barney Asset Management. He was the former CEO of Global Investment Management at Citigroup and Former Treasurer at John Hancock Insurance Company. Thomas W. Jones is currently the Founder and senior partner of venture capital investment firm TWJ Capital and author of the new book From Willard Straight to Wall Street: A Memoir. 
    Podcast Highlights
     
    Who is Thomas W. Jones?   
    Thomas W. Jones was on the cover of Newsweek in 1969 as an iconic revolutionary while studying at Cornell. As a student, Thomas felt that America was at a crossroads and that his generation was tasked with the job of raising the price of oppression. Due to his effort and the effort of countless others, America chose to embrace the spirit of the Constitution and the Bill of Rights and has made significant progress over the last 50 years towards equality.
    In a certain way, Thomas’s life story and career in business is like a microcosm of the story of the growth and development of America as a whole.
     
    Did the fight look like what you thought it would?  
    Thomas was pleasantly surprised when America took the path of opening up opportunity instead of the path of oppression. He believed the toughest fight would be in the business world and he figured that he would have almost no chance at success, but he needed to try. He had to approach business in a way that he provided his own psychological support, because he knew he wasn’t going to receive any from the outside.
    He discovered that if you actually deliver a true 100% commitment, there is a large gap over time between the people who are delivering only 95%. The 5% gap seems small but it compounds over the years and people start to notice. For Thomas, this meant people in the upper echelons of business recognizing that he was getting the job done and eventually taking him on in a mentorship type of relationship.
     
    Where does your motivation and fortitude come from?  
    It takes a certain level of self belief and self confidence to take on tough challenges. For Thomas, his confidence came from his experience in school. At that time, the philosophy of school in dealing with a gifted child was to accelerate them, and that meant that Thomas had skipped two grades. This meant that he was much younger than his peers and once he had entered high school he encountered a number of bullies. It was then that he decided that he wouldn’t let others define who he was. That self possession developed into the mentality that even if he was facing insurmountable odds, Thomas might as well try to get it done.
    Most people never figure out what they are capable of because they never actually put 100% into trying to be their best. You can never know what you can do until you give 100% effort. It’s a wonderful gift that you can give to yourself to learn what your highest potential is. When you learn what your capacity is, you will be able to channel and master it, and you will find arenas where you can give 100% and be successful.
    Thomas’s faith discipline has been another crucial element. Even in the midst of a crisis, praying and trying to see the good in the situation allowed Thomas to continue to fight. Life is going to have times of trial, and having spiritual faith that can sustain you is very important.
    Striving is one way to make life meaningful. A story like Thomas Jones could not have happened anywhere but America. 
    Every single year Thomas would set three goals for himself and having the discipline to achieve those goals each year had a major impact on his life.
    Early on in Thomas’s marriage, he and his wife made some very imp

    • 1 hr 5 min
    TaxDome and How Technology Allows Small Businesses To Compete For a Fraction of the Price

    TaxDome and How Technology Allows Small Businesses To Compete For a Fraction of the Price

    Co-founder of TaxDome - a cloud based practice management solution targeted to small/medium sized firms (1-25), helping entrepreneurs scale quickly & easily. TaxDome is an all-in-one solution for tax and accounting professionals to manage their business. 
    Podcast Highlights
     
    Who is Ilya Radzinsky?   
    Looking back Ilya always had an entrepreneurial spirit and when he was younger he wanted to own a restaurant. He managed to get a job as a busboy but found it was much harder than he thought it would be and didn’t last more than a week. He pivoted his focus and got creative with his first business of selling digital items on eBay. With some encouragement from his parents, Ilya followed the footsteps of his brother and went into finance as a banker and financial analyst. 
    Several years into his career, Ilya’s boss shut down the hedge fund he was working at and took a three month sabbatical. During that time, his brother was getting into product development and found a big opportunity. Ilya decided to team up with him and that’s how we get to present day with TaxDome. Generally, Ilya tries to adapt to the times and look for new opportunities.
     
    Getting Into Finance  
    Finance has a bit of a bad reputation but in many ways it’s like Medicine. There are a number of different roles that you can play within the industry. Ilya enjoyed his career in finance and if it wasn’t for his boss getting divorced he would have probably just continued working at the hedge fund and wouldn’t have gone on to start a business. 
    Oftentimes, the experiences that feel uncomfortable lead to better things in the future. Adversity often refocuses your vision of the world in a more clear way than before and the successful person usually follows a winding path with plenty of setbacks before they get to where they are.
     
    Why TaxDome?  
    In 2010, the trends were moving in the direction of more people completing tax returns online in some way and back in the day, Ilya and his brother started working with a firm that was looking to go fully remote and scale their business. They started building that product for them and it went on to transform their business. A few years ago, Ilya and his brother saw an opportunity with the emergence of SaaS companies and that’s when the idea for Taxdome came alive. They created a similar platform to the one they created before specifically for accountants that allows them to access a plug and play solution for their business without requiring a major IT investment.
    If you’re an accountant, you need a lot of different services in order to run your business and TaxDome is an integrated solution that aims to eliminate as many of those services as possible. TaxDome is trying to reduce the software burden for accountants and allow them to better compete with other businesses as technology changes the way transactions occur. 
    In a lot of ways, small businesses are facing a large challenge of cobbling together a number of software solutions to be able to compete with larger businesses and their economies of scale. TaxDome is championing small businesses and trying to give them the tools and ability to compete and win.
    Adopting a new software solution can be daunting so in order to lower the barrier to entry and give clients an idea of what to expect, TaxDome offers a simulated account without having to sign up. The simulated account allows people to experience the software from the perspective of the owner, the contractor, and the client.
     
    Transparency  
    Transparency is a core tenet of TaxDome. Safety and security are a part of that, but a big focus is on making change more approachable. Customers can look into TaxDome and get an understanding of everything they are going to get and exactly what the value of the software to their company will be. From a business structure, TaxDome i

    • 40 min
    Making Sure Your Insurance Company Pays Up Q&A

    Making Sure Your Insurance Company Pays Up Q&A

    J is answering all your questions about business, short term rentals, personal growth, and whatever else it is you’re curious about. We’re also exploring the subjects of insurance and occupancy in particular, how much insurance do you need and what metrics should be looking at to maximize your occupancy. Insurance is one area that you don’t want to cut corners so make sure you understand how to make it work for you.
    Questions and Answers
     
    How do we handle bad guests?   
    The first step is to breathe and realize you will survive. Everyone will experience this at some point. The process of removing an unwanted guest that has broken your rules is the same no matter the infraction. One thing to note is if the person is willing to pay the fees for breaking the rules, take the money and move on.
    If you have to file a resolution with Airbnb you’re going to need to do it immediately. Your window of opportunity is very small to file a claim so don’t wait to do it. If the guest wants to write a bad review, waiting to make a claim is not going to stop them from writing the bad review. You will have to rely on the content policy to protect you from an unfair negative review.
     
    A question about improving a listing’s rankings  
    The caller has multiple listings but is wondering why a couple of them aren’t performing at all. Before a booking can happen, inquiries must happen, before that views must happen, and before that impressions have to happen. Each one is a statistic that can measured and looked at to identify where in the process the problem lies.
    For this caller there seems to be an issue with the inquiries on her listing. The words in the listing itself may be the problem since people are clicking on the listing at a high rate, but something is turning them away at that point in the conversion process. A lack of reviews may also be a barrier for converting people that are landing on the listing.
     
    A question about guests receiving packages at the unit  
    It’s always better to have guests route their packages to a local UPS store instead of the unit itself. You don’t need the liability of a guest receiving potentially illegal packages and the UPS store is insured against those kinds of things. That also comes a paper trail for an extra level of protection.
     
    Does insurance cover lost business income?  
    The caller had a unit that got flooded which required a rehab and resulted in 12 months of lost income. In her case, the insurance only paid out for the days that were already booked that were canceled. She had the right insurance coverage at the time.
    When it comes to down to getting insurance there is replacement cost and actual cash value and it’s very important to understand the distinction. When it comes to lost business income, J sets the limits at $120,000 and the contents limit at $40,000 because he knows the insurance company will always try to minimize the pay out.
    The caller also made the mistake of registering her insurance under her own name instead of an entity like an LLC. That means she is paying more than J is on each unit, despite having considerably less coverage than he does.
    Since the caller hasn’t deposited the insurance checks yet, she still has the opportunity to make further claims. A public adjuster is someone who can help her claim additional pay outs that she’s entitled to. The caller should look for a public adjuster with experience in hotels and put them on her case.
    It’s important to keep in mind that the typical insurance adjuster works for the insurance company and not for you. 
     
    I already have a business entity, can I use it or should I create a new one?  
    If your lawyer says it’s okay, go for it. 
     
    What happens if a landlord tries to use the landlord presentation against us?  
    The presentation is not legally binding so th

    • 1 hr 24 min
    Scaling A Short Term Rental Business Q&A

    Scaling A Short Term Rental Business Q&A

    One of the most important things to understand about the short term rental business is that it gets easier with the more units you have. If you’re ready to scale up your business and start acquiring new units, you need to take the steps necessary to set yourself up for success. 
    Questions and Answers
     
    What do we with units that have carpets in them?   
    Carpets can be challenging because they are gigantic sponges for bacteria. If your unit does have carpets you need to have a process for keeping it clean in place. Establishing a relationship with a carpet vendor that your cleaning crew can contact to get the work done without getting the approval from you will save you a lot of time.
     
    How many customer service managers do you have and how many hours do they work?  
    J has a pair of customer service managers working for him that cover a total of 16 hours a day. He chose each of them to hire as managers and he trained them directly through a screen sharing app like Zoom or Loom.
     
    I have some people interested in working with me and my short term rental business but they are wary of marketplaces like Airbnb. Is there anything I can do to help them be more comfortable with them?  
    You would think these people would be more comfortable with markets like Airbnb and HomeAway than they would with Facebook. If the caller wants to reassure these people, showing them the listing so they understand what details are being revealed is a good option.
    Starting with Airbnb as your first platform also gives you the advantage of benefitting from their existing background check process. What the landlord really wants to know is the contact information of the person in the case of an emergency, and that can be solved by simply automating parts of the reservation process.
    If you explain to the landlord that you are on the same side of the table and will be making major investments in the unit and don’t want unsavory guests as well, things will go much smoother. In many cases, you have the ability to correct the issue if it does come up than the landlord could with a traditional tenant.
     
    Should I use Guesty if I am bringing on three additional units?  
    J recommends using Smartbnb and Lodgify instead of Guesty to his students. Everybody who brings on multiple units at the same time gets overwhelmed but it gets easier the more you do it. 
    It’s also important to understand the difference between using a tool and using it expertly. If you don’t know how to use the tool well, it’s not going to be able to help you scale your business.
     
    We’ve got our first short term rental unit up and running and want to scale. Should we wait until we’re making more profit to scale or push ahead now?  
    The short term rental business is easier with more units than it is with less. Starting a new unit in a slow season can be very challenging but since the caller has managed to cover the rent of the first unit during one of the slowest periods of the year, they should get started as quickly as possible. 
     
    I have an investor that has reached their maximum writeoff capacity, if they invest with me outside of California can he get write off more?  
    We’re not tax experts and this isn’t tax advice, but there are a number of strategies you can employ to put you in a better tax position. Check out episode 556 of the Cashflow Diary to learn about the Deferred Sales Trust and how it may be a solution to your investor’s problem.
     
    I’m trying to get up and running with Lodgify but I’m having trouble setting up the website, what do I do?  
    J ran into the same trouble initially. The best solution to getting it done is to just find someone that knows how to do it and asking for their help. 
     
    Are you able to do short term rentals in a gated community of is it just a waste of time?  
    Short term re

    • 1 hr 8 min
    Bookings, Marketing, VA’s, and Landlords in the Short Term Rental Business Q&A

    Bookings, Marketing, VA’s, and Landlords in the Short Term Rental Business Q&A

    Robert Vocolla guest hosts the Q&A show with J today and they’re talking about some very important short term rental business questions. Find out about security processes, managing VA’s, marketing your business, getting out of problematic leases, and more.
    Questions and Answers
     
    A question about processes around security technology   
    Rob uses a simple analog process to make sure his guests don’t run into issues with the security system in his units. He uses sticky labels on each panel that warns the guest not to tamper with it and has a basic template in Smartbnb that gets sent out that lets the guest know how to interact with the security system. This has drastically reduced the number of false alarms.
     
    I’ve got three VA’s covering 18 hours a day, seven days a week and they’re great at following SOPs but not so good at doing customer service work?  
    Hiring is always a major challenge, if you want to find someone that can handle managerial level tasks it’s going to take a lot of searching. You may have to review, hire, and fire a number of people before you will find that gem of a person that checks off all the boxes. For this particular caller, they have multiple units in multiple cities and that’s adding to the stress of working with his team.
    A good rule of thumb is to be prepared to train someone for 30 hours for every hour a task would take you to do. A quick tip for your customer service manager is to look at what time of day your business is getting the most messages because that will inform what hours you should assign your team.
     
    What are the most important marketing KPIs to track?  
    There is a whole set of metrics around leads, around customer conversion, and average order and frequency. All of them should be measured and tracked and each one can have a compounding impact on the growth potential of your business.
    Another thing to keep in mind is that a lot of your marketing on Airbnb is about working with the algorithm correctly. Make sure you have the right pictures with good descriptions because your search position in the rankings will determine your success on that platform. 
    Tools like Smartbnb are crucial to understanding the most important metrics in your business. The only way to have metrics to look at and measure is to gather data.
     
    What is the difference between Basic and Pro in Lodgify and Smartbnb?  
    The biggest difference between the two is one uses and API to communicate with other apps and the other uses the older iCal method. Since the caller is using Smartbnb, they should just stick with basic because they already have a built in sync feature that makes Pro unnecessary.
     
    What are you guys doing to get more bookings from booking.com?  
    Getting guests on booking.com is similar to the other channels even if it feels like it’s more work. One of the secrets is to have every single field filled out for your listing and setting your prices correctly with Lodgify. Keep in mind that guests from booking.com may be more seasonal as well.
    Mirror the same types of policies on booking.com that you have on other channels to keep everything consistently.
     
    How do you guys do your messaging for booking.com?  
    No one is currently satisfied with the messaging situation of booking.com. It’s a very manual process but J is actively looking to create a better system. 
     
    A question about a six month reservation opportunity  
    The caller feels like the guest may be trying to pull something over on him. Since that’s the case the question is around the tactical implementation of the reservation. The caller needs to be able to collect in cash and upfront 60 days worth of reservation while also implementing a 30 minimum notification in anything changes. 
    Give the guests multiple plans and ways to pay. Under no circumstances should the caller

    • 1 hr 29 min
    Business Owners Don’t Need to Fear The Next Recession

    Business Owners Don’t Need to Fear The Next Recession

    Jonathan Slain is the Founder and CEO of Recession.com, an author, a highly respected keynote speaker, and an expert on recessions & why business owners don’t need to fear them. 
    Jonathan spent the last Great Recession huddled in the fetal position on the floor of his office. He borrowed $250,000 from his mother-in-law to survive. Jonathan paid his mother-in-law back and is now a highly sought-after consultant (and, yes, he’s still married!). 
    Jonathan understands not only how to prepare your business for the next major recession but also how to turn it into a profitable opportunity.  
    Podcast Highlights
     
    Who is Jonathan Slain?   
    Much of Jonathan’s life has been spent in the metaphorical Batcave, doing the research and preparing for whatever it was that he was working towards. Deep preparation has been the common thread in Jonathan’s life all the way back from high school. Studying people who were successful during major recessions is what drew his attention and his experience during the recent Great Recession is what put him on his current path.
    Jonathan is also a recovering investment banker, studying different companies and economic indicators for 100 hours a week over the course of two years. He learned that as entrepreneurs, we all always have a recession coming, even if it’s not an economic recession. There are a number of personal events that could put your business into a recession and Jonathan’s focus is on being prepared for the next one, whatever shape it happens to take.
     
    How does one plan for things we can’t control?  
    One major change recently in California has been the recent regulations around single use plastic. These regulations are going to have major impacts on many different kinds of businesses. In these situations, there will always be a few entrepreneurs who see the signs and put themselves in a position to take advantage of the coming changes. 
    There have been 11 recessions since World War 2 and they last an average of 11 months. When they do come around, they create a massive amount of disruption in the market that also comes with a number of opportunities. Every business can do things to prepare and position themselves for the major recessions.
     
    The Next Recession  
    We should be looking forward to the next recession, it will happen eventually so you should be prepared. All it really takes is a little forethought and some work upfront that will allow you to pounce when the recession hits, instead of spending the first few weeks or months of the recession trying to catch up.
    Every major recession shares some common elements that you can look at historically and predict what may happen in the future. Marketing dollars go extra far during a recession, can you put some money aside now that will allow you to take advantage of this? What if you had a war chest available to buy distressed businesses and assets?
     
    The #1 thing to do to prepare right now  
    The first step is to assess where you are in your recession readiness. You can go to recession.com and take the free survey to get your recession readiness score. It will also let you know which areas you need to start improving. 
    The second step is to tune up your personal and business finances. How much debt are you carrying right now? Do you have a line of credit available to you so you can take advantage of opportunities that come up? Can you eliminate your personal guarantees on any loans you have right now?
    If you’re going to be prepared for a recession, you need to start doing it now because these options don’t exist once the recession is all over the news and the economy starts to tip.
     
    What are some mistakes you’ve made?  
    For Jonathan, his biggest mistake during the last recession was not being diversified at all. What would happen to short term rental owners if there was a

    • 51 min

Customer Reviews

P Wats ,

My Favorite Show

J’s Show CashFlowDiary is the first Real Estate podcast I’ve encountered when I found out I wanted to become a real estate investor. This podcast had provided me with phenomenal advice, information, and a new mindset. This podcast has inspired me to grow as a person, an entrepreneur, and as an action taker. Thanks J for creating this podcast.

JoshCrist ,

An incredible show!!

J. Massey is an incredible host and brings on some of the most inspiring guests in the investing, real estate and business world! Each interview has an awesome blend of tactical advice (how do we translate this into immediate, cashflow action today) and the deeper mindset that allows those tactics to become an extension of who you are. The stories he shares are raw and authentic, and he invites his guests to be just as candid. Highly recommend making this podcast one of your go-tos!

Maze Decker ,

Great host, great show

J. Massey is one of the best hosts I know, plus he invites awesome guests. Their topics and conversations are always interesting and it doesn't get me bored at all. Super helpful tips too. Recommended

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