TopPodcast.com
Menu
  • Home
  • Top Charts
  • Top Networks
  • Top Apps
  • Top Independents
  • Top Podfluencers
  • Top Picks
    • Top Business Podcasts
    • Top True Crime Podcasts
    • Top Finance Podcasts
    • Top Comedy Podcasts
    • Top Music Podcasts
    • Top Womens Podcasts
    • Top Kids Podcasts
    • Top Sports Podcasts
    • Top News Podcasts
    • Top Tech Podcasts
    • Top Crypto Podcasts
    • Top Entrepreneurial Podcasts
    • Top Fantasy Sports Podcasts
    • Top Political Podcasts
    • Top Science Podcasts
    • Top Self Help Podcasts
    • Top Sports Betting Podcasts
    • Top Stocks Podcasts
  • Podcast News
  • About Us
  • Podcast Advertising
  • Contact
Not in our directory?
Add Show Here
Podcast Equipment
Center

toppodcastlogoOur TOPPODCAST Picks

  • Comedy
  • Crypto
  • Sports
  • News
  • Politics
  • True Crime
  • Business
  • Finance

Follow Us

toppodcastlogoStay Connected

    View Top 200 Chart
    Back to Rankings Page
    Business

    Cashflow Diary™

    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.

    Advertise
    • Apple Podcasts
    • Google Play
    • Spotify

    Latest Episodes:
    The Key Short Term Rental Systems That Allow You To Scale Your Business To Six Figures Feb 20, 2020
    Show notes

    🔍 GET THE STR INSIGHTS THAT CREATED 7-FIGURE HOSTS
    After managing 400+ units and helping STR hosts in 17 countries achieve $800+ monthly net income per bedroom, I'm sharing my best strategies - free.

    Every Monday and Thursday, you'll get:
    ✓ One actionable STR automation strategy
    ✓ Data-driven market insights that matter
    ✓ Implementation frameworks that work
    ✓ Real case studies from our 20,000+ community

    No fluff. No theory. Just proven systems from my living room "office" (fueled by Celsius and Chick-fil-A).

    These are the exact insights that help our community achieve:
    • 30%+ profit margins
    • 80% automated guest communication
    • 5+ hours saved weekly

    👉 Join 20,000+ successful STR hosts at https://newsletter.cashflowdiary.com/welcome

    Now, let's dive into today's episode...


    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 to go through the first year with only one unit. Putting the right short term rental systems in place that allow you to grow past that point and start running more units is the secret to long term success. Learn what systems you must implement in your short term rental business.

    • Have you ever asked a traditional real estate investor or landlord about short term rentals?

    A good analogy is imagining what a person who owns a Costco franchise or someone who owns a vending machine business. Each person will have firmly believe that what they are doing is the best option, but the Costco person probably thinks the vending business is too much work, and the vending machine owner thinks the Costco is too much money upfront.

    The traditional landlord is like Costco, they are wholesaling their property in 12 month terms. Short term rentals are like the vending machine business, you’re both selling the same product, just with a different package and sales channel. The differences are the customers being served and the level of services you are providing.

    Short term rental operators are the retail version of real estate, we sell the property one day at a time, and the power is in our ability to be efficient. It’s the system that delivers the service, and that’s the difference between the two.

    As a resource becomes more available and efficient, demand for that resource starts to go up. Cell phones are a good example, they started off big and clunky and difficult to manufacture, but now they are small, powerful, and ubiquitous. Short term rental operators make real estate more efficient.

    The more efficiency we bring to the table, the more revenue we can drive in our businesses and other people’s organizations as well. The key to your future is putting this principle into effect for your life.

    • Putting Short Term Rental Systems In Place

    There are a few key short term rental systems that have to be in place if you’re going to capture this efficiency. This includes a system for cleaning the unit on a regular basis, a maintenance and repair system for fixtures like doorknobs, a communication system for communicating with your guests, and a system for managing the availability of multiple calendars per property.

    Most of the time, we recommend people start out with AirBnB because they have the absolute best system for customer acquisition. But there are other platforms as well, and if you can operate efficiently on those platforms, you can make much more money per booking.

    If you’re going to make the maximum amount of profit in this business you need to have a system in place for availability 24 hours a day, 7 days a week. This is probably the easiest area for us to outperform the market because the average short term rental operator has no system in place to handle inquiries and can sometimes take days to respond.

    You have to provide more value to the marketplace than just you are able to provide. It has to be bigger than you. That kind of thinking is how you unlock five figure paydays, six figure success, and seven figure freedom. Learning how to provide value to the marketplace efficiently allows you to scale and reach levels of income that most people have no idea how to achieve, in less time than you would think possible.

    Taking your customers direct will make your business more efficient, it will allow you to deliver your service more efficiently with a lower cost, while also increasing your profit. Once you get your customer from a marketplace like AirBnB, it’s your job to keep them happy so that they only want to do business with you, that way you pay the customer acquisition just once instead of every time.

    If your business feels like work, that’s a sign that your short term rental systems are broken. You can’t just add tools and technologies to your business, you need the knowledge and training on how to use them well.

    • How much value are you providing to the marketplace?

    When you have one unit, you are providing 30 days of value each month. What happens when you have 12 units? That means that every single month you are delivering a year’s worth of economic value. This is why short term rental systems are so important, without them there would be no way to seperate your time from your income, and no way to grow a business to a level that makes an impact on the world.

    Links:

    cashflowdiary.com/roadmap

    Thank you for listening! If you enjoyed this podcast, please subscribe to the show on iTunes and Stitcher Radio!


    🏠 Want to Join the Elite 10% of Short-Term Rental Hosts?

    Dear Future Top Performer,

    Are you tired of working harder instead of smarter in your STR business? Here's a wake-up call: The most successful hosts aren't grinding 24/7 – they're leveraging a proven formula that transforms average properties into profit powerhouses.

    Let me share something game-changing with you...

    There's a simple yet powerful equation that's revolutionizing the STR industry:
    L × C × F × M = GP

    This isn't just another fancy acronym – it's the exact blueprint top performers use to:
    • Generate consistent leads without burning out
    • Convert browsers into eager bookers
    • Maximize guest frequency (hello, repeat customers!)
    • Amplify their margins while others race to the bottom

    Right now, you're probably leaving thousands on the table. The truth? 80% of your potential profits are locked behind just 20% of the right actions.

    Ready to stop bleeding money and start leading the pack?

    Join our newsletter today and get weekly insights that will help you:
    ✓ Master the Growth Formula
    ✓ Optimize your listing for maximum visibility
    ✓ Create an irresistible guest experience
    ✓ Scale your business the smart way

    Don't let another day pass watching others succeed while you're stuck in the grind.

    👉 Click here to join the newsletter and start your journey to the top 10%!


    Cashflow Diary Roadmap Q&A Feb 17, 2020
    Show notes

    🔍 GET THE STR INSIGHTS THAT CREATED 7-FIGURE HOSTS
    After managing 400+ units and helping STR hosts in 17 countries achieve $800+ monthly net income per bedroom, I'm sharing my best strategies - free.

    Every Monday and Thursday, you'll get:
    ✓ One actionable STR automation strategy
    ✓ Data-driven market insights that matter
    ✓ Implementation frameworks that work
    ✓ Real case studies from our 20,000+ community

    No fluff. No theory. Just proven systems from my living room "office" (fueled by Celsius and Chick-fil-A).

    These are the exact insights that help our community achieve:
    • 30%+ profit margins
    • 80% automated guest communication
    • 5+ hours saved weekly

    👉 Join 20,000+ successful STR hosts at https://newsletter.cashflowdiary.com/welcome

    Now, let's dive into today's episode...


    Get the lowdown on the Cashflow Diary Roadmap program and how the program has been designed to get students to six and seven figure businesses as quickly as possible. Find out what makes the Cashflow Diary Roadmap different and how becoming a student in the next enrolment period could completely transform your life.

    • What is the difference between what’s offered to Cashflow Diary Roadmap students versus traditional students?

    Cashflow Diary Roadmap students are the first to take advantage of the new Cashflow Diary app, a one stop location for training materials, networking opportunities, and additional features like a vendor marketplace. The app also allows us to bring on subject matter experts to provide help with specific areas. The app also connects Roadmap students to their accountability coach in a real time format.

    There are also a number of assessments that your accountability coach will help you get through, all of them designed to help you become a bigger, better, badder entrepreneur and keep you on track. You will have access to a monthly 45 minute coaching call and additional tracking tools to keep you on target.

    Cashflow Diary Roadmap students also get access to 3 weekly training calls that cover topics and tactics that we wouldn’t otherwise be able to do. Everything in the Roadmap is centered around facilitating the transformation necessary to create six and seven figure businesses.

    • Who are the accountability coaches?

    Each accountability coach is someone who has accomplished the things we are helping Roadmap students achieve. They have proven they have mastered the same material you will be studying as a Cashflow Diary Roadmap student. The whole point of the accountability coaches is to provide real time help for the students and eliminate what they perceive as roadblocks that are preventing them from moving forward.

    • Does the Roadmap focus on a particular market?

    There is no one market that the Cashflow Diary Roadmap focuses on, but for the more exotic use cases of short term rentals there will be either additional training or resources made available for them.

    • Will you be discontinuing the Q&A’s?

    The short answer is no, but where they are done and how they are done is changing. They are only going to be made available to members only. The previous format came with a lot of restrictions that prevented it from really solving the problems we are looking to solve. By changing the format we will be able to better serve the members and help them advance in towards their goals.

    • Will there be a Facebook presence after this transfer?

    There will be a presence on Facebook, it will be focused on the other group. We will be doing more free training for members of that group but our primary focus will be on working with existing Roadmap students. The challenging thing with Facebook is disseminating information because Facebook gets to determine who sees what, which can make things difficult. The Roadmap is our effort in providing a solution to that problem.

    All the recommendations we have made in the program are tailored to help you get results as fast as possible without getting distracted by the next shiny new object.

    • What is the opportunity cost of not joining?

    What happens if you never get there on your own. Only you know the answer to that question.

    Links:

    cashflowdiary.com/roadmap

    Thank you for listening! If you enjoyed this podcast, please subscribe to the show on iTunes and Stitcher Radio!


    🏠 Want to Join the Elite 10% of Short-Term Rental Hosts?

    Dear Future Top Performer,

    Are you tired of working harder instead of smarter in your STR business? Here's a wake-up call: The most successful hosts aren't grinding 24/7 – they're leveraging a proven formula that transforms average properties into profit powerhouses.

    Let me share something game-changing with you...

    There's a simple yet powerful equation that's revolutionizing the STR industry:
    L × C × F × M = GP

    This isn't just another fancy acronym – it's the exact blueprint top performers use to:
    • Generate consistent leads without burning out
    • Convert browsers into eager bookers
    • Maximize guest frequency (hello, repeat customers!)
    • Amplify their margins while others race to the bottom

    Right now, you're probably leaving thousands on the table. The truth? 80% of your potential profits are locked behind just 20% of the right actions.

    Ready to stop bleeding money and start leading the pack?

    Join our newsletter today and get weekly insights that will help you:
    ✓ Master the Growth Formula
    ✓ Optimize your listing for maximum visibility
    ✓ Create an irresistible guest experience
    ✓ Scale your business the smart way

    Don't let another day pass watching others succeed while you're stuck in the grind.

    👉 Click here to join the newsletter and start your journey to the top 10%!


    Getting Landlords To Say Yes Feb 13, 2020
    Show notes

    🔍 GET THE STR INSIGHTS THAT CREATED 7-FIGURE HOSTS
    After managing 400+ units and helping STR hosts in 17 countries achieve $800+ monthly net income per bedroom, I'm sharing my best strategies - free.

    Every Monday and Thursday, you'll get:
    ✓ One actionable STR automation strategy
    ✓ Data-driven market insights that matter
    ✓ Implementation frameworks that work
    ✓ Real case studies from our 20,000+ community

    No fluff. No theory. Just proven systems from my living room "office" (fueled by Celsius and Chick-fil-A).

    These are the exact insights that help our community achieve:
    • 30%+ profit margins
    • 80% automated guest communication
    • 5+ hours saved weekly

    👉 Join 20,000+ successful STR hosts at https://newsletter.cashflowdiary.com/welcome

    Now, let's dive into today's episode...


    One of the unique things that you need to understand is that people do things for their reasons, not theirs, and their reasons make sense to them. Be careful about assuming that the way you think is the way that everyone thinks. When it comes to talking to landlords as a short term rental operator and getting them to say yes, there is a proven process that you can use to start the conversation and close the deal.

    • Why do you think that landlords want?

    If you’re the one offering a solution to a problem, you’re in business. That means you need to understand the pain of the problem in order to make a sale/present yourself as the solution to the problem. If you’re not getting the answers from the people you’re talking to, it’s not the business model that’s broken, you’re probably just approaching the situation incorrectly.

    Many of us put off our pain until the last possible moment, landlords have pain too, you just have to understand what that pain is. When someone is in pain, they don’t care about a person’s pedigree as long as they believe they can solve their problem. When it comes to talking to landlords, their biggest problem is vacancy and as long as you can speak competently by understanding that the landlord conversation becomes much easier.

    The conversation is only difficult because you don’t yet have a thorough understanding of their problems yet. As you continue to have a better handle on the problem, you will run into another set of challenges. Namely, getting the person to admit that they have a problem.

    The average short term rental guest stays at a venue for 5.6 days. That means that roughly five times a month, the unit has to be cleaned from top to bottom, which is an interesting point you can bring up in conversation with a landlord. How often does that happen with a traditional long term rental situation? The answer is almost never.

    Another benefit to the landlord is a general decrease in wear and tear on the unit. Guests typically spend their time somewhere other than the unit itself, especially compared to long term tenants. Your relationship with a landlord is a symbiotic relationship where you are both helping each other.

    • What do you think the landlord gains by working with you as a short term rental operator?

    The benefits of a consistently occupied unit not only leads to more reliable payments for the landlord, the building is valued based on its net operating income and if they can show that vacancy is going to be consistent, it can add up very fast for the landlord.

    The landlord also gets the advantage of decreased leasing fees and management fees. Working with you as a short term rental operator can save them thousands of dollars in leasing fees and every day the unit is vacant they are losing money, which is a problem you can solve directly.

    As a short term rental operator, the landlord can be confident that their property will be sufficiently covered by the right insurance, which is not something they can always rely on with traditional tenants. Short term rentals also get to take advantage of all the technology available that most landlords have no idea how to make use of, including increased security and fire protection. We can protect their property better than they or their tenant can.

    Professional operators can’t be taken advantage of in the way that the scare stories on the news are saying they can.

    • How To Start A Conversation With Any Landlord

    Here’s the perfect script for starting the conversation with any landlord.

    “Hi, my name is (your first name). My company and I are looking to lease a number of properties in the area. Are you the right person to talk to about that?”

    You want to plan the seed that when it comes to sign the lease, it’s going to be with a corporation and with someone who can potentially solve their vacancy problem.

    On the phone, there is no other goal than to get an appointment to see the property and that’s it. Once you’re on site avoid saying have an AirBnB business because that’s not factually accurate and the name has already been poisoned by news outlets all over the country.

    Once you’re on the property, when someone asks you “is this AirBnB?”, you respond with how you acquire customers. When someone asks you “what does your company do?”, you respond with who you serve. Ultimately, the conversation should move towards getting around the landlord’s existing prejudices around short term rentals.

    One principle to keep in mind when answering their questions is asymmetrical sharing, when you share your information with them they will feel obligated to answer your questions as well. Answering their questions is your opportunity to demonstrate your competency and ability to solve the landlord’s problem.

    Another thing to keep in mind is that when you are touring the property, you should be spending that time in qualifying the property.

    • Does it matter how you dress when it comes to the appointment with the landlord?

    How you dress does not matter, what matters is how confident you are when you show up. Whatever attire you have to wear to achieve that will work.

    • How do you navigate newly established business credit that does not reflect a rental history? What if the landlord does not want the entity to guarantee the lease?

    The highest level of success will come from working with owner controlled buildings, business credit will not likely come into play unless you’re dealing with REIT. Most owners won’t care if you don’t have a history, don’t make that assumption.

    If the landlord doesn’t want the entity to guarantee the lease, that’s fine. The entity is still on the lease, you just offer a personal guarantee.

    Links:

    cashflowdiary.com/howmanyunits

    Thank you for listening! If you enjoyed this podcast, please subscribe to the show on iTunes and Stitcher Radio!


    🏠 Want to Join the Elite 10% of Short-Term Rental Hosts?

    Dear Future Top Performer,

    Are you tired of working harder instead of smarter in your STR business? Here's a wake-up call: The most successful hosts aren't grinding 24/7 – they're leveraging a proven formula that transforms average properties into profit powerhouses.

    Let me share something game-changing with you...

    There's a simple yet powerful equation that's revolutionizing the STR industry:
    L × C × F × M = GP

    This isn't just another fancy acronym – it's the exact blueprint top performers use to:
    • Generate consisten...


    The Secret To Raising Capital From Investors Feb 10, 2020
    Show notes

    🔍 GET THE STR INSIGHTS THAT CREATED 7-FIGURE HOSTS
    After managing 400+ units and helping STR hosts in 17 countries achieve $800+ monthly net income per bedroom, I'm sharing my best strategies - free.

    Every Monday and Thursday, you'll get:
    ✓ One actionable STR automation strategy
    ✓ Data-driven market insights that matter
    ✓ Implementation frameworks that work
    ✓ Real case studies from our 20,000+ community

    No fluff. No theory. Just proven systems from my living room "office" (fueled by Celsius and Chick-fil-A).

    These are the exact insights that help our community achieve:
    • 30%+ profit margins
    • 80% automated guest communication
    • 5+ hours saved weekly

    👉 Join 20,000+ successful STR hosts at https://newsletter.cashflowdiary.com/welcome

    Now, let's dive into today's episode...


    Do you want a six or seven figure real estate business that will actually allow you to retire from your job? Raising capital is a key skill you need to understand. The window of opportunity is wide open and there is more opportunity than you think in the short term rental business, now is the time to take action and get started.

    • Why would a landlord allow you to lease their property and make more money than them?

    Landlords are in different places in their lives and the value different things, that’s what creates the opportunity for us. In fact, most retail businesses do exactly the same thing. The lease a location where they operate out of, in order to make more money than the cost of the lease. The principle is basically the same.

    • What do you believe investors are looking for? What does it take for investors to say yes to giving you money?

    There are basically two things you need in order to get investors to say yes to you. Character and confidence. There are many different ways you can demonstrate those, producing content like a podcast or Youtube videos and they show up consistently. Demonstrating competence is also very important, because he who educates the market, dominates the market. Always answer at least one question with your content and actually helps people.

    When it comes to raising capital, there are three types of people that you want to be in front of: guests, landlords, and investors. Another thing to keep in mind is that investors are often the people right next to you, they are not always the person in the fancy suit. Every person has an investor identity and the most interchangeable piece of the process is the deal.

    Even if you don’t currently have a piece of property under contract right now, you should still be able to talk about who you serve, how you serve them, and everything the customer prefers. If you can’t talk confidently about that without having a particular address in mind, that’s where the problem in raising capital lies.

    You must become a professional information gatherer because that will put you into a position to diagnose, make a prognosis, and then prescribe. You can’t do it any other way because you will never know what the investor wants. The challenge is you can’t ask them directly because most people don’t even know they have an investor identity. If you walk into any given Starbucks, there is probably several million dollars in investable capital sitting around.

    You are the operator and the one with a solution, make sure they know that. There are many different reasons someone will choose to invest, and your job is to figure out what that is and solve their problem. Invite them into your world and show them that you are an expert by educating them.

    If you lead with a deal based on what you believe is great without uncovering what the investor is actually looking for, you both lose.

    • The Profit Analysis Quadrant Conversation

    There are four areas of profit: appreciation, amortization, depreciation, and cash flow. Each of those can be manipulated to create the outcome that the investor is looking for. You have to know how to use these tools to create a deal that solves the investor’s problems.

    Show them you’re an expert by educating them and asking the right questions, find out what they are doing and what problems they are trying to solve, then explain how your transaction can be structured to solve their problem, then ask them to enrol. The final step is to ask for the referral so you start the process over again.

    There is no magic deal structure that will make raising capital easier. There is a nearly infinite combination of variables that you can use to structure a deal, your limiting beliefs are the only thing holding you back.

    • Do I need to create a business plan when raising capital from investors?

    A business plan is usually just a guess. You may have a solution proposed in the plan but if it doesn’t solve the investor’s problem it won’t matter. If you don’t ask what their problem is, then you won’t know and raising capital will be very difficult.

    It’s better to realize that your ability to produce value for the marketplace can be used to solve their problem, you just need to ask the right questions and tailor your solution so it solves their problem.

    • How much time do you typically take to repay an investor?

    There is no set time limit. You have to diagnose their problem first because not every investor needs the money back immediately, it could be 15 years in the future. It’s more important solving their problem in the timeline that makes sense for that investor.

    • Do you ever offer a lease option to buy?

    No, we always start with a basic lease. There are other tools at our disposal and we want to keep it simple for the landlord. We just want to be in the loop in the future in case you do want to buy down the road. It’s better to use the capital you would tie up in an option to furnish the unit.

    Thank you for listening! If you enjoyed this podcast, please subscribe to the show on iTunes and Stitcher Radio!


    🏠 Want to Join the Elite 10% of Short-Term Rental Hosts?

    Dear Future Top Performer,

    Are you tired of working harder instead of smarter in your STR business? Here's a wake-up call: The most successful hosts aren't grinding 24/7 – they're leveraging a proven formula that transforms average properties into profit powerhouses.

    Let me share something game-changing with you...

    There's a simple yet powerful equation that's revolutionizing the STR industry:
    L × C × F × M = GP

    This isn't just another fancy acronym – it's the exact blueprint top performers use to:
    • Generate consistent leads without burning out
    • Convert browsers into eager bookers
    • Maximize guest frequency (hello, repeat customers!)
    • Amplify their margins while others race to the bottom

    Right now, you're probably leaving thousands on the table. The truth? 80% of your potential profits are locked behind just 20% of the right actions.

    Ready to stop bleeding money and start leading the pack?

    Join our newsletter today and get weekly insights that will help you:
    ✓ Master the Growth Formula
    ✓ Optimize your listing for maximum visibility
    ✓ Create an irresistible guest experience
    ✓ Scale your business the smart way

    Don't let another day pass watching others succeed while y...


    Why Short Term Rentals? Feb 06, 2020
    Show notes

    🔍 GET THE STR INSIGHTS THAT CREATED 7-FIGURE HOSTS
    After managing 400+ units and helping STR hosts in 17 countries achieve $800+ monthly net income per bedroom, I'm sharing my best strategies - free.

    Every Monday and Thursday, you'll get:
    ✓ One actionable STR automation strategy
    ✓ Data-driven market insights that matter
    ✓ Implementation frameworks that work
    ✓ Real case studies from our 20,000+ community

    No fluff. No theory. Just proven systems from my living room "office" (fueled by Celsius and Chick-fil-A).

    These are the exact insights that help our community achieve:
    • 30%+ profit margins
    • 80% automated guest communication
    • 5+ hours saved weekly

    👉 Join 20,000+ successful STR hosts at https://newsletter.cashflowdiary.com/welcome

    Now, let's dive into today's episode...


    When you understand the “why?” behind your business, it can often help you with the “how?” of your business. In this episode of the podcast J reveals the story of how he came to realize that short term rentals are perhaps the greatest opportunity for people getting into real estate investing in a very long time, but also why the window to take advantage of that opportunity is closing a little bit every single day.

    • The Power of Real Estate

    Prior to getting into real estate, J and his wife went through some incredibly difficult times personally. His wife was unable to eat or drink due to a condition she developed while pregnant, and J suffered an injury where he punctured his lung which prevented him from walking and talking at the same time. His back was against the wall with no money and a terrible credit score, and that was when a friend recommended he look into real estate investing.

    At that point J’s best ideas are what got him into that position, which is something you should consider as well. Wherever you are now, your best ideas got you to where you are. It wasn’t until J left his comfort zone and stopped pretending that everything was alright that things started to change.

    J started doing what he was being asked to do and after closing his first transaction in June of 2008, he realized that his beliefs around money were holding him back and preventing him from seeing the opportunity that was around him.

    You can play any game if you are taught the rules, and real estate is no different. Once J got started, everything snowballed and accumulated and in the course of the next 12 months his life was completely changed. His business eventually developed into buying apartments and multifamily units, billboards, cell towers, and other types of property all over the United States, all along the way he fine tuned the systems that allowed him to scale.

    As great as that success is, J wasn’t satisfied. J started thinking about how he could make more of a difference in the world which lead him to create the Cashflow Diary and started helping other people with their own entrepreneurial journey. It was actually one of those people that introduced him to short term rentals.

    One of the interesting things about real estate is that it’s a great way to build wealth, but a horrible way to build income. A lot of landlords lose money on long term rentals for quite a while. Short term rentals are a response to the change in consumer habits and change the way we look at real estate.

    Short term rentals have been around for a long time, but what is new about the industry is the impact that technology is having on it. Technology is transforming everything about real estate and the short term rental industry is leading the way.

    • Planning For The Future

    The rules of money have changed and most of us were never taught them in the first place. People are finding out the hard way that social security is more like social insecurity and their 401(k) isn’t going to last as long as they thought it was going to. We all must have a way to produce income not only when we are awake, but passively as well. Inflation and tax increases are coming in the future, and we need a way to protect ourselves from that.

    For most people, their first transaction is real estate is about taking on a massive obligation with almost no experience, but one of the game changing realizations with short term rentals is you don’t need to own a property to start the business. You only need to control the property, and that means a lease.

    J crunched the numbers and found that a lease came with less risk, less money up front, and can be turned around quicker. He also found that he had a good chance of getting all his cash back in 10 to 18 months, as well as having a source of cash flow. When compared to a traditional approach where he wouldn’t be able to expect that money back for at least 15 years, short term rentals win hands down.

    If J were to start all over today, short term rentals are the strategy he would start with. You will gain the experience of owning a property without the risks associated with actually owning it, but you also get experience in working with customers and creating the systems that allow to scale rapidly. You can get the on the job training with the 30 year commitment.

    • The Short Term Rental Opportunity That’s Right Infront of You

    It doesn’t take any special skills to be successful with short term rentals other than the willingness to learn and be persistent. The industry is wide open but it’s not going to stay that way forever. The trouble is we have a tendency to wait until an opportunity is blatantly obvious before acting on it, but now is the time to act.

    It’s been a long time since real estate has seen anything new, but the window is closing slowly on the short term rental industry. As major players like Marriott start to enter the market, it’s only going to get harder each year, just like every other technique in real estate.

    Short term rentals produce twice the gross revenue of traditional long term rentals while often only increasing the expenses by 10%. When you do the math, you end up with higher net operating income and that’s why finance is going to change.

    Thank you for listening! If you enjoyed this podcast, please subscribe to the show on iTunes and Stitcher Radio!


    🏠 Want to Join the Elite 10% of Short-Term Rental Hosts?

    Dear Future Top Performer,

    Are you tired of working harder instead of smarter in your STR business? Here's a wake-up call: The most successful hosts aren't grinding 24/7 – they're leveraging a proven formula that transforms average properties into profit powerhouses.

    Let me share something game-changing with you...

    There's a simple yet powerful equation that's revolutionizing the STR industry:
    L × C × F × M = GP

    This isn't just another fancy acronym – it's the exact blueprint top performers use to:
    • Generate consistent leads without burning out
    • Convert browsers into eager bookers
    • Maximize guest frequency (hello, repeat customers!)
    • Amplify their margins while others race to the bottom

    Right now, you're probably leaving thousands on the table. The truth? 80% of your potential profits are locked behind just 20% of the right actions.

    Ready to stop bleeding money and start leading the pack?

    Join our newsletter today and get weekly insights that will help you:
    ✓ Master the Growth Formula
    ✓ Optimize...


    The 10 Things I Wish I Knew Before I Got Started In Real Estate Feb 03, 2020
    Show notes

    🔍 GET THE STR INSIGHTS THAT CREATED 7-FIGURE HOSTS
    After managing 400+ units and helping STR hosts in 17 countries achieve $800+ monthly net income per bedroom, I'm sharing my best strategies - free.

    Every Monday and Thursday, you'll get:
    ✓ One actionable STR automation strategy
    ✓ Data-driven market insights that matter
    ✓ Implementation frameworks that work
    ✓ Real case studies from our 20,000+ community

    No fluff. No theory. Just proven systems from my living room "office" (fueled by Celsius and Chick-fil-A).

    These are the exact insights that help our community achieve:
    • 30%+ profit margins
    • 80% automated guest communication
    • 5+ hours saved weekly

    👉 Join 20,000+ successful STR hosts at https://newsletter.cashflowdiary.com/welcome

    Now, let's dive into today's episode...


    We are talking about making short term rentals happen for you, making them easier and faster, bigger, better, and badder. If you feel the need to get started and need that extra push to make things happen, you can go to cashflowdiary.com/roadmap to finally build your business. J reveals the 10 things he wishes he knew before he got started in the short term rental business as well as answers a number of questions from the viewers.

    • How many units does it take to retire?

    When you’re in pursuit of an outcome, you may not know what the goal is. When people are getting started in real estate, they often have a dream of retiring but have no idea how many units they need to achieve that goal. If you want to know exactly how many short term rental units you need to retire you can go to cashflowdiary.com/howmanyunits to calculate your magic number.

    • Is it possible to get my first unit in the first month?

    The most reliable answer is it depends. If you follow the program and do exactly what it says, you shouldn’t have any problems landing your first unit, it all depends on whether you are willing to put in the work and how comfortable you are with failing. You may have to hear a large number of ‘no’s’ before you get a yes, but if you can push through and put in the work, it’s definitely doable. You just have to move at the speed of instruction.

    This program is best suited to people who are okay with leaving the ‘why’ for later so that you can provide value now. Even people who have been in the short term rental real estate world can get stuck if they don’t have a system for scaling and the tools and team to support their growth. It takes time to learn systems, but they can’t be implemented just by reading a book or watching a video. It requires hands on experience to make them work.

    • Will we be able to plagiarize all the systems and everything you do in your short term rental business?

    You not only get to plagiarize everything, the program literally contains the exact messages that J sends his guests. It’s easy to replicate the ingredients, but we also give you the recipe.

    You need to learn more than just tactics. As the marketplace matures, you’re going to need to have the skills to build a real brand that will allow your business to continue growing.

    • Do short term rentals work in Chicago?

    The short term rental business works everywhere there is a need for housing.

    • Is the app available to current students or only people in the Roadmap?

    People joining the Roadmap get access to the app first but it will be coming to existing students that are currently in Facebook.

    • Do I have to under price if I’m new?

    You don’t have to approach this the way you would with traditional real estate, you would be doing things in the wrong order and costing yourself some opportunity. You also have to be aware of how difficult it is to get accurate data to set your prices and they can be manipulated.

    • #10. I was not aware of the use cases for short term rentals

    The real secret to the short term rental business is specialization. Who you are trying to serve will determine so much about your business and is really the foundation for everything else. There are a huge variety of specialized use cases for short term rentals that you can serve including mobility challenges, government, insurance, pet owners, and more.

    You have to understand specialization. We are retailers, and retail is niche. You have to customize your business to suit a particular kind of customer right from the very beginning. Failure to do so will be why you average daily rate won’t be as high as it could be. There is no such thing as too niche, if you don’t niche down you make will all kinds of mistakes.

    • #9. This business is very review based

    You can do everything you were supposed to do and you can still get a negative review. It’s going to happen and you need to deal with it.

    • Is $20k enough to start an AirBnB business?

    We don’t have an AirBnB business, we have a short term rental business. It all depends on who you are going to serve, people have gotten started for much less and much more. There is no set number for everybody.

    Just because you have money, that doesn’t mean you're going to succeed. Can you hear no fifteen times a day? That attitude is much more important than money.

    • #8. I didn’t realize how political the business is

    There are a lot of challenges in some jurisdictions. Some places really care, mostly because the perception of the short term rental industry is based on other people who haven't been doing the work.

    • #7. How easy it is to operate the business from a distance

    With the right systems, it can be surprisingly easy to operate a short term rental business from anywhere.

    • #6. Established property management companies typically didn’t work

    Traditional property managers just aren’t capable of doing certain things when it comes to short term rentals. Oftentimes the scale and scope of your operation will just be too much for them, which is why J developed and refined his own system to make it work.

    • #5. How new the industry is

    You can tell how new an industry is by the lack of software available. There is a huge amount of technology that just doesn’t exist yet for our use case.

    • #4. How big the opportunity is around additional services

    Having a system in place to consistently charge and collect for things like early arrival and late checkout can make a big difference in your bottom line. Being able to offer simple services like an additional cleaning can be huge.

    • #3. The window is closing

    In a lot of places the opportunity is still wide open but the window is closing. The time to build your brand is now. Major companies are making moves into the short term rental business because they see the same opportunity in the industry as we do.

    • #2. How much energy people waste

    Your guests will waste so much electricity it’s incredible. In 2019, J spent over $32,000 on utilities, and that doesn’t include the internet. That’s why they have developed a system that has almost completely removed that as an expense, which is available in the Roadmap training section.

    • #1. How fundamental standard operating procedures are

    Standard operating procedures that are written down and easily followed are the foundation for a business that can grow and serve hundreds of customers a month, all with one hour a day of work. There is a lot of work that goes into creating those SOP’s and members of the Roadmap get them just for being part of th...


    The Cashflow Diary Story with Brett Swarts Jan 27, 2020
    Show notes

    🔍 GET THE STR INSIGHTS THAT CREATED 7-FIGURE HOSTS
    After managing 400+ units and helping STR hosts in 17 countries achieve $800+ monthly net income per bedroom, I'm sharing my best strategies - free.

    Every Monday and Thursday, you'll get:
    ✓ One actionable STR automation strategy
    ✓ Data-driven market insights that matter
    ✓ Implementation frameworks that work
    ✓ Real case studies from our 20,000+ community

    No fluff. No theory. Just proven systems from my living room "office" (fueled by Celsius and Chick-fil-A).

    These are the exact insights that help our community achieve:
    • 30%+ profit margins
    • 80% automated guest communication
    • 5+ hours saved weekly

    👉 Join 20,000+ successful STR hosts at https://newsletter.cashflowdiary.com/welcome

    Now, let's dive into today's episode...


    J Massey was the featured guest on the Capital Gains Tax Solutions podcast with Brett Swarts recently and they talked about everything from how J got started in real estate investing, to key short term rental strategies, growth mindset, the Cashflow Diary, and more.

    Questions and Answers

    • What is your background and what’s your current focus?

    J started out from a very difficult situation in life. J’s wife has a condition that when she’s pregnant she can’t eat or drink, and at the same time as her pregnancy J had a punctured lung and brutal asthma. The challenge was that neither of them could earn income by going to work so they needed to find a solution. A friend recommended that he look into real estate investing so with literally no money and terrible credit J began wholesaling properties.

    After being introduced to taxes, J started keeping the properties and that developed into a portfolio that included single family houses, mortgages, and cell phone towers. Eventually people started asking how he’d been able to achieve all of that, so J began teaching others how to do the same thing. One of J’s students introduced him to the idea of short term rentals, and three years ago J switched his focus to teaching people how to create their own short term rental business.

    • What is your super power and how does it shape how you help others today?

    J grew up as a military kid outside of the States and growing up overseas has given him the ability to adapt to new situations very quickly. J is autistic and has ADHD and he considers those his super powers as they help him connect the dots and learn new things surprisingly fast. It’s also a gift being able to share that information and help other people as well.

    • How did you transfer the idea of a weakness into a strength?

    Being able to provide for your family is great but when that’s accomplished there’s not much else to do. At the age of 38, J found himself functionally retired and with nothing to do until one person came to him and asked to learn everything he knew. In the process of teaching this person the skills of real estate investing, both J and the other person went through incredible transformations. He realized how fulfilling and valuable it is to help other people achieve their dreams and that ultimately put him on his current path.

    • Does your approach to life filter into your basketball game?

    J judges his success in a basketball game by the number of rebounds and blocks he made, the things that enable someone else to be able to be great. Setting the example of helping other people is very important to J. In many ways, entrepreneurs can be some of the most selfless individuals and since they are so connected to so many different people, they have the ability to make fundamental positive changes to their communities.

    • Walk us through the tactical parts of what you do and how you help people create more wealth.

    One of the things that people rarely tell you is that owning real estate long term is a great way to build wealth but horrible for building income. Income doesn’t materialize until the debt servicing is complete. When J had 450 units, there was always something to repair and something to do, so they started looking for ways to increase income and reduce the work. This is where short term rental units come into the picture.

    Short term rentals have a number of advantages to the user compared to a traditional hotel room that customers appreciate, which are some of the things he covers on the Cashflow Diary podcast.

    • What’s the process once someone gets their first deal done?

    We’ll assume two things: each bedroom in a short term rental will net you $800 per month throughout the year. The second thing is that you have $250,000 to invest in real estate. On average, that $250,000 will allow you to acquire anywhere from 10 to 17 short term rentals. When you do the math, you realize that within 18 months or less, you will have your $250,000 back.

    That means that not only do you get your money back, but you’ve turned it into a stream of income and a business that you can continue to grow.

    Saving that much money is hard, and making large financial commitments like a mortgage can be extremely successful because of the lack of experience. By building a short term rental business first, you are building a stronger, bigger, and better real estate portfolio than any other strategy while also building your experience.

    • Are short term rentals harder to own and manage than regular rentals?

    Since J came into the short term rental industry with prior experience, he had a number of different skills in place that he could bring to the space. He applied those skills and developed a system that allows his students to leverage a number of different pieces of technology and manage their business with only an hour of work a day.

    The tools are important, but you also need an expert who knows how to use it to get the best results. That’s where J’s business really shines, as they impart the expert skills the student’s need to excel. Building a team is absolutely crucial to success in the short term rental industry. You will never achieve the results you could with a team on your own because the skill sets required are so diverse. It only works if you build a system and a team.

    J’s system allows him to take a completely blank space and get it online and generating revenue in only 72 hours. Bringing in his wife was a big asset for J because of the additional skill set and perspective she brought to the table.

    Real estate is the best risk adjusted rate of return you can have. It creates positive impacts in the community and helps people in their daily lives, which can also make very rewarding.

    • What’s your take on selling real estate and what tax strategies do you implement?

    J generally avoids selling, but if he does he always tries to make sure he has enough offsetting credits and depreciation to deal with whatever the capital gains would be. He’s not a fan of a 1031 exchange, so he will take on different projects like larger rehabs to create more offsetting losses. This is also one of the reasons why J is so excited about the Deferred Sales Trust that Brett talks about.

    The time constraint of the 1031 exchange can result in very unfavorable deals and poor decisions just to avoid the tax. The Deferred Sales Trust is a very attractive alternative to the 1031 exchange.

    • What is the single best practice to implement to be successful in real estate investing and building wealth?

    The first skill is failing fast, failing forward, and failing frequently. As a child you learned how to fail while learning to walk and that’s a skill you need to cultivate. Real estate is the same wa...


    Thomas W. Jones: From Campus Revolutionary to Powerful Financial Services Leader Jan 23, 2020
    Show notes

    🔍 GET THE STR INSIGHTS THAT CREATED 7-FIGURE HOSTS
    After managing 400+ units and helping STR hosts in 17 countries achieve $800+ monthly net income per bedroom, I'm sharing my best strategies - free.

    Every Monday and Thursday, you'll get:
    ✓ One actionable STR automation strategy
    ✓ Data-driven market insights that matter
    ✓ Implementation frameworks that work
    ✓ Real case studies from our 20,000+ community

    No fluff. No theory. Just proven systems from my living room "office" (fueled by Celsius and Chick-fil-A).

    These are the exact insights that help our community achieve:
    • 30%+ profit margins
    • 80% automated guest communication
    • 5+ hours saved weekly

    👉 Join 20,000+ successful STR hosts at https://newsletter.cashflowdiary.com/welcome

    Now, let's dive into today's episode...


    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 important decisions. The first was for Thomas to get his MBA at night school in order to acquire the skills he knew he was going to need for the future. And the second was the decision to live below their means and save his wife’s salary each year. That later allowed them to purchase their first property in Boston which was the first step towards accelerating their wealth.

    Reference: From Willard Straight to Wall Street: A Memoir, Thomas W. Jones

    • Tom’s Takeaway

    The first step is to believe in yourself, the second step is to make a plan in one year increments that will get you from where you are to where you want to be. You can also pull that back. What are you going to get done this week to move you down that path? What about this month? Each accomplishment adds up, and the accomplishments of several years in a row will move your life forward in ways that you can only dream about. When things don’t go right immediately, don’t be defeated. Believe in yourself and the power of putting in 100% effort.

    Links:

    From Willard Straight To Wall Street on Facebook

    Thank you for listening! If you enjoyed this podcast, please subscribe to the show on iTunes and Stitcher Radio!


    🏠 Want to Join the Elite 10% of Short-Term Rental Hosts?

    Dear Future Top Performer,

    Are you tired of working harder instead of smarter in your STR business? Here's a wake-up call: The most successful hosts aren't grinding 24/7 – they're leveraging a proven formula that transforms average properties into profit powerhouses.

    Let me share something game-changing with you...

    There's a simple yet powerful equation that's revolutionizing the STR industry:
    L × C × F × M = GP

    This isn't just another fancy acronym – it's the exact blueprint top performers use to:
    • Generate consistent leads without burning out
    • Convert browsers into eager bookers
    • Maximize guest frequency (hello, repeat customers!)
    • Amplify their margins while others race to the bottom

    Right now, you're probably leaving thousands on the table. The truth? 80% of your potential profits are locked behind just 20% of the right actions.

    Ready to stop bleeding money and start leading the pack?

    Join our newsletter today and get weekly insights that will help you:
    ✓ Master the Growth Formula
    ✓ Optimize your listing for maximum visibility
    ✓ Create an irresistible guest experience
    ✓ Scale your business the smart way

    Don't let another day pass watching others succeed while you're stuck in the grind.

    👉


    TaxDome and How Technology Allows Small Businesses To Compete For a Fraction of the Price Jan 20, 2020
    Show notes

    🔍 GET THE STR INSIGHTS THAT CREATED 7-FIGURE HOSTS
    After managing 400+ units and helping STR hosts in 17 countries achieve $800+ monthly net income per bedroom, I'm sharing my best strategies - free.

    Every Monday and Thursday, you'll get:
    ✓ One actionable STR automation strategy
    ✓ Data-driven market insights that matter
    ✓ Implementation frameworks that work
    ✓ Real case studies from our 20,000+ community

    No fluff. No theory. Just proven systems from my living room "office" (fueled by Celsius and Chick-fil-A).

    These are the exact insights that help our community achieve:
    • 30%+ profit margins
    • 80% automated guest communication
    • 5+ hours saved weekly

    👉 Join 20,000+ successful STR hosts at https://newsletter.cashflowdiary.com/welcome

    Now, let's dive into today's episode...


    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 is not a sales heavy company. The goal is to be so easy to use and obviously valuable that the customer can easily make an informed buying decision.

    • The Effects of Technology on Business

    Technology is reducing the barrier to entry. 20 years ago to start a business you had to spend a large amount of money on infrastructure. Today businesses can access incredible resources like cloud computing that have drastically reduced the costs of starting a business. Technology has also reduced the risk of starting a business by lowering the cost of nearly everything.

    In many ways, entrepreneurship is not for everyone. It’s not all afternoons off and coffee with friends. You have to be okay with failure and pivoting in order to be an entrepreneur and people shouldn’t feel pressured to start a business just because it’s currently the sexy thing to do.

    For Ilya, being an entrepreneur and being comfortable with failure has been a skill that he developed over time. Being able to take in negative feedback and not take it personally is crucial to the improvement and success of your business.

    • Ilya’s Takeaway

    Write down the pros and cons of your potential decisions. Instead of keeping everything in your head, put it down on paper and make it clear. Few things in life are black and white, they’re mostly grey and putting things down on paper allows you to better navigate big decisions.

    Links:

    Get into the daily demo at taxdome.com

    Thank you for listening! If you enjoyed this podcast, please subscribe to the show on iTunes and Stitcher Radio!


    🏠 Want to Join the Elite 10% of Short-Term Rental Hosts?

    Dear Future Top Performer,

    Are you tired of working harder instead of smarter in your STR business? Here's a wake-up call: The most successful hosts aren't grinding 24/7 – they're leveraging a proven formula that transforms average properties into profit powerhouses.

    Let me share something game-changing with you...

    There's a simple yet powerful equation that's revolutionizing the STR industry:
    L × C × F × M = GP

    This isn't just another fancy acronym – it's the exact blueprint top performers use to:
    • Generate consistent leads without burning out
    • Convert browsers into eager bookers
    • Maximize guest frequency (hello, repeat customers!)
    • Amplify their margins while others race to the bottom

    Right now, you're probably leaving thousands on the table. The truth? 80% of your potential profits are locked behind just 20% of the right actions.

    Ready to stop bleeding money and start leading the pack?<...


    Making Sure Your Insurance Company Pays Up Q&A Jan 02, 2020
    Show notes

    🔍 GET THE STR INSIGHTS THAT CREATED 7-FIGURE HOSTS
    After managing 400+ units and helping STR hosts in 17 countries achieve $800+ monthly net income per bedroom, I'm sharing my best strategies - free.

    Every Monday and Thursday, you'll get:
    ✓ One actionable STR automation strategy
    ✓ Data-driven market insights that matter
    ✓ Implementation frameworks that work
    ✓ Real case studies from our 20,000+ community

    No fluff. No theory. Just proven systems from my living room "office" (fueled by Celsius and Chick-fil-A).

    These are the exact insights that help our community achieve:
    • 30%+ profit margins
    • 80% automated guest communication
    • 5+ hours saved weekly

    👉 Join 20,000+ successful STR hosts at https://newsletter.cashflowdiary.com/welcome

    Now, let's dive into today's episode...


    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 there isn’t much a landlord could complain about in that regard.

    • Is there an upfront charge for a public adjuster’s services?

    Most of them are contingent on the increase of the claim. If the adjuster doesn’t think they can increase the claim, they probably won’t take the case. If they want you to pay upfront, that’s a warning sign and you should look elsewhere.

    • What insurance company do you recommend?

    Since J doesn’t want to be construed as trying to sell insurance, he can’t make a particular recommendation but you look in the student group on Facebook you will probably find some suggestions.

    Links:

    cashflowdiarypodcast.com

    cashflowdiary.com/star

    Thank you for listening! If you enjoyed this podcast, please subscribe to the show on iTunes and Stitcher Radio!


    🏠 Want to Join the Elite 10% of Short-Term Rental Hosts?

    Dear Future Top Performer,

    Are you tired of working harder instead of smarter in your STR business? Here's a wake-up call: The most successful hosts aren't grinding 24/7 – they're leveraging a proven formula that transforms average properties into profit powerhouses.

    Let me share something game-changing with you...

    There's a simple yet powerful equation that's revolutionizing the STR industry:
    L × C × F × M = GP

    This isn't just another fancy acronym – it's the exact blueprint top performers use to:
    • Generate consistent leads without burning out
    • Convert browsers into eager bookers
    • Maximize guest frequency (hello, repeat customers!)
    • Amplify their margins while others race to the bottom

    Right now, you're probably leaving thousands on the table. The truth? 80% of your potential profits are locked behind just 20% of the right actions.

    Ready to stop bleeding money and start leading the pack?

    Join our newsletter today and get weekly insights that will help you:
    ✓ Master the Growth Formula
    ✓ Optimize your listing for maximum visibility
    ✓ Create an irresistible guest experience
    ✓ Scale your business the smart way

    Don't let another day pass watching others succeed while you're stuck in the grind.

    👉 Click here to join the newsletter and start your journey to the top 10%!


    Previous 1 8 9 10 11 12 70 Next

    Related Podcasts

    How I Built This with Guy Raz

    1

    How I Built This with Guy Raz Business
    Planet Money

    2

    Planet Money Business
    Inside Strategic Coach: Connecting Entrepreneurs With What Really Matters

    3

    Inside Strategic Coach: Connecting Entrepreneurs With What Really Matters Business
    BiggerPockets Real Estate Podcast

    4

    BiggerPockets Real Estate Podcast Business
    The Smart Passive Income Online Business and Blogging Podcast

    5

    The Smart Passive Income Online Business and Blogging Podcast Business
    Bad With Money With Gabe Dunn

    6

    Bad With Money With Gabe Dunn Business
    footer-logo

    Contact Us

    Toll Free: 844-670-7747

    Links

    • Home
    • Top Charts
    • Networks
    • Apps
    • Independents Podcasts
    • Podcast Advertising
    • Podcast News
    • Contact Us
    • About Us
    • Analytics & Insights

    Stay Connected

      Privacy, Terms of Use & Our Code of Ethics Protecting Content Creators Copyrights