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Cashflow Diary™

Cashflow Diary™

Author: J. Massey

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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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607 Episodes
Cashflow Diary Roadmap Q&A

Cashflow Diary Roadmap Q&A


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: Thank you for listening! If you enjoyed this podcast, please subscribe to the show on iTunes and Stitcher Radio!
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: Thank you for listening! If you enjoyed this podcast, please subscribe to the show on iTunes and Stitcher Radio!
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!
Why Short Term Rentals?

Why Short Term Rentals?


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!
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 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 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 the program. We are currently in the beginning stages of the short term rental industry and profit margins are good, which means the professionals are coming, and standards and expectations are rising. You absolutely need to have standard operating procedures in place if you’re going to compete in this business in the future. Links: Thank you for listening! If you enjoyed this podcast, please subscribe to the show on iTunes and Stitcher Radio!
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 way and understanding that will allow you to get out there and start making things happen. Most of us haven’t given ourselves enough opportunity to fail in order to get it right! Other than that, realize that it’s never going to be perfect. Make the decision to get to your destination and do what it takes to get there, detours, full stops, and all. Give yourself the grace to work at it until you get it done. When the ‘why’ gets big, the ‘how’ gets easy. How do you stay centered in your values? Praying and reading the Bible is central to J’s ability to stay focused on his mission. The world comes at all of us and sometimes the people we look up to are not going to be the ones that enable our transformation. Don’t let the world tell you what you should be.  Seeing his students develop and grow is something that keeps J going as well. It inspires him to keep looking for the next thing he can learn and add to his student’s lives.  Links: Thank you for listening! If you enjoyed this podcast, please subscribe to the show on iTunes and Stitcher Radio!
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!
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 Thank you for listening! If you enjoyed this podcast, please subscribe to the show on iTunes and Stitcher Radio!
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: Thank you for listening! If you enjoyed this podcast, please subscribe to the show on iTunes and Stitcher Radio!
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 rentals can definitely be done in gated communities, there is just a few extra steps you need to take to make sure everything is communicated properly.     I’m negotiating my first unit and the owner wants me to put the first six months of the lease under my name instead of my LLC, what should I do?   Don’t do the deal that way. Put the entity on the lease and be the personal guarantor. You don’t want to be open to the potential liability and being a personal guarantor will probably satisfy what the owner is really looking for.   If you’re new to short term rentals, when should you fund and grow?   Many of J’s students have been able to access over a million dollars in capital to grow their business and they’ve found that once they get started, it’s fairly easy to pay back their obligations. The thing you have to consider is the opportunity cost of inaction and not taking advantage of the money that is available.   What are the benefits of running Airbnb under a business name?   We don’t do Airbnb, we run a short term rental business. To answer the question, it only takes one time with something defective in your unit to cause you major liability problems. The longer you’re in the business the more likely something like that will come up so you’re going to want to have protection in place. Run your business through an entity of some kind.   Do you need to get financing when you get started or do you wait until your first unit?   One of the best things about the short term rental business is that you don’t need an exorbitant amount of financing to make it work. Once you get one unit, it’s a game of patience until you get your next unit and so on. Self funding is a real thing, and another major advantage of the short term rental business model is that it prepares you for owning real estate long term. You can get financing or not, it’s up to you. One thing to keep in mind is that the less other people’s money you use, the faster you will put yourself into a strong position in a very short period of time.    One of our rules of thumb is that we have to double market rent to reach our goals. Does this sound right to you?   You’re on the right track but one of the things to keep in mind is to measure on a month to month basis, but not necessarily the 12 month basis. There is seasonality to how travel happens and you’ll start to see the deviations in each month and begin to better prepare for them. That will also help you smooth out the low periods by organizing your business properly. Links: Think and Grow Rich Thank you for listening! If you enjoyed this podcast, please subscribe to the show on iTunes and Stitcher Radio!
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   Getting guests on 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 may be more seasonal as well. Mirror the same types of policies on that you have on other channels to keep everything consistently.   How do you guys do your messaging for   No one is currently satisfied with the messaging situation of 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 accept less than their target profit numbers for that unit.   Are there any resources I can use to explain the short term rental business to financial institutions?   The risk of real estate and the risk of hospitality are different but all the literature and strategies that J uses are meant for landlords, not financial institutions. The majority of lending institutions are still putting together the underwriting model for the short term rental business and they’re not quite ready yet. You can find some resources that will help you tell the story of your business to prospective partners within the Mastermind product.    I have a potential situation where I may have to get out of a lease. How do I get out?   If you want to get out of your lease, and keep in mind this is not legal advice, you need to be able to document the incidents that come up. One of the promises that the landlord makes with you is called Quiet Enjoyment of the unit, and if they are failing to follow up on that promise you may have something to work with.  Talk to a landlord attorney to learn what you need to prove that the landlord has broken the contract that will let you out of the lease. In this case, the landlord has a problem and it shouldn’t be the caller’s problem. Whichever path the caller takes, he needs to document everything.   How much do we pay for a manager? What basic rules does a manager follow? What calendar platforms does Lodgify sync with?   Check out module 4 and 5 of the Mastermind product.    What would be the best way to approach an owner about Airbnb?   Rule #1 to keep in mind is that this is not an Airbnb business, this is a short term rental hospitality business. Airbnb is just one channel where you get your customers. If you use the terminology “Airbnb business” you won’t even get your foot in the door with most landlords. Go to to learn how to present the business to property owners and to get a deeper understanding of the methodology of the business. Setting up the business the right way at the front end is what will allow you to scale.   Hawaii is a 30 day market and I’ve got a 25 day vacancy in between reservations. What can I do about it?   What can you sell either the previous guest or future guest to cover the revenue you would need for that vacancy period? Being creative is what is going to bridge that gap and once you create these offers you can use them for any number of guests in the future as well. Links:
Jonathan Slain is the Founder and CEO of, 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 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 major scandal with Airbnb? What is a hedge that you can build into your portfolio now that has an inverse relationship with a recession so that when part of it goes down, other assets go up. You need to have an emergency break so you know when to stop borrowing. Set your limits before the crisis so not all your decisions will be emotionally based. Check your vendors and start building up additional channels for customer acquisition. Don’t just rely on Airbnb. Short term rentals are not likely to go away in a recession but you do need to add a little insurance to your business by removing a single point of failure.   Is there something that smaller companies are more vulnerable to?   The number one vulnerability for small businesses and entrepreneurs is the balance sheet. How many months of operating expenses do you have available in the event that business dries up and you need to survive? Plan for the event that your monthly revenue starts to decline and think of expenses that you can cut at certain thresholds. Have those difficult conversations now before they become absolutely necessary. Another tip is to think of the niches that bigger businesses can’t take advantage of. What things will people still spend their money on during a recession that you can look to and benefit from? Reference: Rock The Recession, Jonathan Slain   Jonathan’s Takeaway   The first thing and the most technical starting points you can begin with is bench marking. Take the assessment and find out where you are right now and what you can do to get prepared today. Links: Thank you for listening! If you enjoyed this podcast, please subscribe to the show on iTunes and Stitcher Radio!
This is a review based business, and that means you will probably get some bad reviews at some point. The question is what do you do about them? More than bad reviews, we’re talking about preparing for the holidays, click bait photos, and more. Questions and Answers   For the inventory checklist, how detailed do you get?    You can be as detailed as counting the silverware, the question is “at what point will you file a claim?” It probably doesn’t make sense due to the manpower and hours it would take to follow up on that. A better way to think about it is “is there enough silverware in the unit?” The benchmark for detail should be somewhere around where you would file a claim for.   Preparing for the upcoming holidays   Now is the time to get ready for the holidays. Change the batteries for any automatic door locks, replace the pilot lights for any gas furnaces, get blankets into the units where the climate gets chilly. Have a chat with your crew now to find out if they are going to be working during the holiday.   We had a guest break the do not obstruct the camera rule. How long should we wait to leave a bad review without the guest retaliating? How is the guest punished for not paying the fee?   Many of the platforms have a content policy and if the guest leaves a review that violates the policy it will be hidden. The review is basically the guest’s experience with your service so that means it can be very subjective. When leaving a review, neither party will be able to see the review until both have posted it. Ideally you should wait until the last minute of the fourteen day period to avoid a retaliatory bad review. If the guest has already left the review, then you have to rely on the content policy to help you out. In terms of fees and guests not being willing to pay, just state the facts of what happened. Remove the emotion and Airbnb may be able to take care of the fee for you.   I have a new short term rental unit, how long should I need to wait to get my first booking?   The first issue with the caller’s unit is that since they are targeting business travelers their unit may be too large. Two bedroom units that are pet friendly don’t usually have vacancy issues. They tend to be perfect for small families going through an insurance claim so linking up with a local insurance company may be a good move. For J, if he’s going to be working with a two bedroom unit, he’s going to gear it towards a market that he knows works well with that much room. Take a look at the events that are happening locally and focus on the kind of customer you want to serve. Another thing to note is that the winter season is slow for the area where this caller is from. There is a stream of revenue that’s right in front of you, you just need to get clear on who they are and get in front of them. What are they searching for and how can you appeal to them?   Being insurance friendly   Note in your titles for your listings that you are insurance friendly. This has made a big difference in the occupancy rates of J’s units.   Regarding an arbitrage unit, are you protected by your lease if there is a change in ownership?   If you’ve done your lease correctly, they can’t end your lease early as long as you pay your rent and follow the terms. That doesn’t guarantee that they will renew but they can’t terminate it.   What size of unit should I target to get past the ordinances in place and actually reach the owners?   Part of the reason we focus on short term rentals is because we ultimately want to own real estate in the long term. Phase 1 is getting one unit, phase 2 is picking up a few more units, and phase 3 is being able to pick up units at your leisure. Start with the size of buildings that you intend to own and the numbers make sense.  Don’t go larger than owner direct, you should be able to get the owner on the phone when you need to in the event of a problem.    What’s in it for a real estate agent to help me?   The short answer is commission. In general, real estate agents will be able to assist you, even if they don’t have all the knowledge of the short term rental model. In many ways, you will have to train them in what you need.    How do you feel about click bait photos?   This is a horrible idea. When it comes to photos, you are competing for the click and people will not click on click bait style photos. Professional photos are far superior for communicating your brand and business than pictures of Eminem.   Do you secure your wifi router?   On most routers, there is a way to access the control panel of the router that connects all your various locks and devices. The way J protects this is by taking a photo of the physical information on the back of the router, than blacking it out with a marker and electrical tape to prevent a guest from accessing the info.    Is there anything operationally different for the insurance guest?   No matter who contacts you first, the person will always have to go back to the insurance company. Because of this the insurance guest takes longer to close and there are more questions involved. Also note that insurance guests tend to use a lot of data so keep your internet plan in mind.  Insurance guests don’t care about recommendations for restaurants and have a number of different concerns that you need to communicate that don’t apply to regular guests.   How will bad reviews influence a new listing? Should I start a new account?   The simple answer is to start a new account. The only factor the caller may want to preserve is the age of the account, but that is more than made up for by the benefits of having a fresh account. By having additional units you would also generate a number of reviews that will minimize the impact of bad reviews if you go the route of not creating a new account. Sometimes things go wrong and a listing will just need a fresh start.   If you have multiple listings, what website or platform do you recommend using?   The platforms you use should be relative to the types of customers you are trying to attract. Most people should start on Airbnb because of the built in training wheels that help you get started. As you get more experience, it’s easy to graduate to other platforms.   I’m operating in a market with a lot of amateurs, have you ever come across this?   Every market has a significant number of amateurs because the barrier to entry is so low that almost anyone can give it a try. This is why the concepts that J teaches are so important. Do your best to start earning repeat business and you won’t be competing with the amateurs in your market.    How do you handle changing codes between guests?   J has his team change the codes at 11 am which is also the departure time. The new code is not given to the arriving guest until between 3 or 4 pm. This all fits into the process checklist that makes sure everything is done and ready for the new reservation.   How do you address an inquiry when they don’t have a complete profile?   Many of the platforms have been dealing with discrimination issues and one of the ways that Airbnb has chosen to address it is by hiding the profile pictures of users. They may actually have a profile picture, you may just not be able to see it.   I have three listings and am looking to grow, should I be on multiple platforms?   To get a true ROI from systems and processes, you should definitely look to get on multiple platforms and acquire more listings as soon as possible.   How do you feel about owner financing for short term rentals?   There’s nothing wrong with owner financing a short term rental, you’re just going to give up speed.   Do you have pointers for managing email?   Google filters are your friend, you will get tons of messages which is why we use tools like Smartbnb to make communication easier. Communication is one of the things that can crush you if you don’t do it right.   When should you jump to another platform besides Airbnb?   When your customer is on those other platforms, but don’t concern yourself with scaling until you have systems in place to handle between 7 to 10 units. Keeping track of finances and operations becomes more challenging as you grow so build the systems first.   A question about operating units out of state   It doesn’t matter if you start during high or low season, there are pros and cons to each and they tend to even out over the course of the year either way.  There is no one system to have in place when looking at a new city, you need all of them in place to have the best chance of success. Having everything in place allows you to simply duplicate what you’re already doing so you can get rolling faster.   Links: Thank you for listening! If you enjoyed this podcast, please subscribe to the show on iTunes and Stitcher Radio!
Jonathan Levi is an experienced entrepreneur, angel investor, and lifehacker from Silicon Valley. Jonathan is known for speed learning his way to all achievements in life: from entrepreneurship to podcasting and even dating. Since 2014, Jonathan has been one of the top-performing instructors on Udemy, with his course Become a SuperLearner® (now retired) earning him over 60,000 students.  He has since snowballed this success into the launch of his own brand and platform, SuperHuman Academy, which produces such products as the award-winning SuperHuman Academy Podcast (3 million+ downloads) and numerous online courses. He is based in Tel Aviv, Israel, preparing to release his 3rd book “The Only Skill That Matters”   Podcast Highlights   Who is Jonathan Levi?    Jonathan grew up in Silicon Valley and was always meant to be an entrepreneur. In many ways he struggled in school because he couldn’t learn the same way that everyone else seemed to do. Deep down, Jonathan is a maker and a creator that is focused on solving problems and learning new things all the time. Jonathan was always a bright kid but he had problems in the classroom environment. The only way he made it through high school and got through the curriculum was by being medicated.  When he got into business school, he knew that medication wasn’t going to cut it. He needed to figure out another way to learn that made sense for him. It was around that time that he found someone who had developed a methodology for speed reading and accelerated learning that completely changed Jonathan’s life and gave him his first real world super power. After meeting multiple real world super humans, Jonathan learned that anyone can do these incredible things simply by learning the techniques and practicing. Jonathan is a big believer in the law of attraction, but he’ll be the first to tell you that it only works if you implement the law of action first. There are very few things in life that can’t be accomplished if you put in the work to learn the ropes. Whatever challenge you are facing in life, the difference between excitement and anxiety is knowledge. For Jonathan, it was a series of individual moments that culminated in his super power. He didn’t plan for online courses to be his business, it just sort of happened after moving to Israel and exploring entrepreneurial opportunities. After discovering a course on coding and seeing how successful it was, Jonathan dug into what it took to create a course and put out his first one on Udemy. Slowly but surely, it developed into a full time business.   Learning Is The Only Skill That Matters   Learning is the ultimate meta skill and the only skill that matters. There are proven techniques to improve your ability to learn. There is no genetic advantage that the world’s best learners have over everyone else. Studies have shown that with six weeks of training anyone can rewire their brain to resemble the brain of a memory champion. There are people well into old age who are learning new skills just as efficiently as their younger counterparts.  You don’t have a lousy memory, you just don’t know how to use it right yet. Our current education system hasn’t been modified for a long time. It hasn’t taken in the new ways of learning that we’ve discovered in recent years. It’s actually theorized that the ancient Greeks used similar techniques of visualization that advanced meta learners use today, but the techniques were suppressed by the early Church.    Learning vs Memorization   There is a difference between memorization and learning but we can’t learn anything without committing it to memory. You need to be able to apply your knowledge in order to make use of it, but that’s not possible without memorization first. Reference: The Only Skill That Matters, Jonathan Levi   Jonathan’s Takeaway   Make it simple, if you experience a quick win you will likely want to experience more. In the next 24 hours you are probably going to encounter five to ten new people. Introduce yourself and memorize their name by creating a unique visualization for each one. Before you go to bed, set yourself a reminder to review how many people you remember. If that intrigues you, you are ready to experience something that is exponentially more powerful. Links: Thank you for listening! If you enjoyed this podcast, please subscribe to the show on iTunes and Stitcher Radio!
The Listing Reviews Q&A

The Listing Reviews Q&A


Sometimes your technology breaks on you! Even so, we’ve got a number of listener questions tackled today including a couple brutally honest (but helpful) short term rental listing reviews. We always come from a position of honesty in hopes that you will make more money, so we’re not going to tell you comforting lies just to make you feel better. Listen in to learn why the bad photos can sink your listing and what you can do about it. Questions and Answers   A question about a 37 day booking and the importance of reviews    One of the things to know about the short term rental business is that it is definitely a review based business. Experience in this business is generated specifically by scaling up and doing the work more often. For this caller, they shouldn’t pass on the 37 day booking unless it is going to hurt their business long term. A long term booking will always make that unit’s performance suffer when compared to other more short term reservations. But if it allows them to add another unit financially, it may be a good move because it will allow the caller to achieve Super Host status by the end of the quarter.  It can also be important to run an AirDNA report on your zip code to understand the trend for your area. That will allow you to understand whether your prices are on point or if you’re leaving money on the table.   How do I get an affiliated link from Uber and Lyft?   Inside the app, you can find your share code which is the code you can use for your bookings and guests. Working with restaurants by sending them business instead of getting paid for the referral may actually be superior to an affiliate relationship. Having them on your side in political or municipal issues will probably be more important than having an additional revenue source.   J reviews a caller’s first post on Airbnb   When creating a short term rental listing, lead with photos with the inside of the unit instead of the amenities. Photos of the exterior can also lead to security issues if it’s possible to identify the address of the unit. The caller’s photos should probably be reshot due to the handheld nature of them as well as the general poor quality. They suffer from lighting and focus challenges and the caller’s bookings will probably be lower than what they could have achieved. Another good tip is to stay away from vertical photos at all times. The caller has definitely put in some work on the short term rental listing, but seems to have skimped on a few crucial elements like the photos and design. In order to tell the right story with your photos, you have to make the investment and do them right. The ideal reaction to your short term rental listing should be the reader feeling like they must stay at your unit.   I’ve got a meeting with the zoning department, do you have any pointers for me?   Since the caller only has three minutes to talk, he should be using his time to instill doubt in his listeners because right now they are certain that the caller is the bad sort of short term rental owner. He should show them that he’s a professional and has systems in place to deal with all the common issues that people complain about with other less professional short term rental owners.   Another review of a caller’s first short term rental listing   The caller already has some hesitation about the photos for her listing. The reason the photos look off to the caller is that their photographer used HDR, which is something that you should always avoid. HDR can cause many different types of issues with the lighting and focus of the photo. Nearly all the photos on the listing have to be scrapped. Preferably, the next photographer avoids HDR, uses a 15mm lens, and uses natural light instead of attempting to color correct after the fact.   How much can I depart from the blueprint you’ve laid out if it makes sense for who we want to serve?   If you’re thinking about who you want to serve and making choices based on that, you aren’t deviating from the blueprint at all. If the caller wants to serve business travelers from Mexico and knows what they need and want from a short term rental listing, then they should go for it.  One thing to keep in mind is that business travelers probably don’t need much square footage and if the caller goes with a larger unit they may run into underutilization. The bulk of business travel is done with smaller units.   Any thoughts on Properly to manage cleaners?   Properly is a great tool to manage cleaners, but the question is can the staff doing the clean effectively use the tool. If they can, then definitely take advantage of it.   Do you refresh Wheelhouse manually?   J lets the software refresh all its own and it handles everything just fine. He does check it a couple of times a week just to make sure it’s doing what it’s supposed to be doing but that’s it. Links: Thank you for listening! If you enjoyed this podcast, please subscribe to the show on iTunes and Stitcher Radio!
There is no definitive good deal in the short term rental business. If you want to know if your deal is good or not, you need to know one simple thing first. It’s something that’s going to drive your reviews and the growth of your business, and that’s meeting your customer’s expectations. Figure out who you want to serve first and that will make the answers to your questions much clearer.  Questions and Answers   Are you still hunting for apartment deals?    J still loves apartments, he’s just changed who he puts in them. With apartments, net operating income is the name of the game and most importantly, if you can manage that properly the value goes up as well. J is not getting out of the apartment game anytime in the near future.   Do you think it’s a good idea to incentivize guests to do a load of laundry before they end their stay?   Quality control becomes an issue here. How do you know the laundry was cleaned correctly? There are other ways to lower your cleaning costs if that’s the goal. J tends to shy away from asking his guests to do anything, some guests will actually become offended by getting the request to do additional work. For this particular caller, the issue may lie in the cleaner that he’s using and their method of billing for work. Ideally, with a linen service, you should only be paying for your laundry that has been weighed while dry. When it comes to a guest checking out, if you have a checklist for them to complete, be upfront with the reasoning for the tasks so they don’t have to wonder why they are putting in some extra work.   What’s the best way to avoid bed bugs before they appear?   Bed bugs tend to come in with a guest, they don’t typically just appear. A good tip is using a metal luggage rack to reduce the incidence of a guest putting their luggage on the bed directly. Protecting the mattress with a casement is also a good precaution. Bed bugs are typically pretty rare, but there are still steps you should take to minimize your risk. Insurance is one example of a way to cut the cost, the trick is making sure the coverage is actually what you need. It’s not uncommon for a bed bug infestation to cost you thousands of dollars to remediate. Be sure that your insurance actually covers bed bugs specifically. You don’t want to get into a situation where you save some money on your premiums but aren’t actually covered from the risk you’re trying to mitigate.   How do we get around the key fob issue?   We tend to leave the key fob inside the unit and the trick is getting the guest to the unit for the first time. Module 3 of the Mastermind product covers this in more depth. Go to to learn more.   Pricing in the Short Term Rental Business   As you enter into your slower season, pricing becomes even more important. If you aren’t doing dynamically adjusted pricing, you’re either leaving money on the table or having a lower occupancy than you should.   I have an opportunity to buy an eight unit apartment building and I want to use them for short term rentals, do you think this is a good deal?   There is no definitive good deal. What’s a good deal for J will probably not be a good deal for you. However, there is a customer that your business is best suited to serve. There are other factors that determine if the deal is right for you and it all stems from who your customer is. You won’t know it’s a good deal until you know who your customer is.  What’s most important, what’s going to drive your reviews and the growth of your business, is meeting your customer’s expectations, and you get to choose who you want to serve.   What markets do you search for apartment deals in?   Deals tend to come our way right now, so J isn’t on the search for apartments deals at the moment. If we were looking, some markets might include Long Beach, Phillidelpia, and parts of North Carolina would be on the list.   What are some ways that you can find owners that are willing to do subleasing for Airbnb?   There are a couple of things to understand. You are not subletting and you don’t have an Airbnb business, you have a short term rental business. If you start off thinking you have an Airbnb business, that will limit your capacity. That being said, finding landlords is fairly easy. Look for “For Rent” signs and call them. To get a better idea of what to say and how the system works, check out the free presentation at Owner controlled buildings are a great way to build your experience while also building your business.   I have three units and people want to rent them long term, how can I prevent that?   It’s not uncommon for a smaller square foot location to outperform a larger square footage space in certain markets. Since the clients that the caller is asking about are typically business people, there shouldn’t be a big issue with letting them rent long term. Whether the guest wants to stay one day or hundreds of days, it doesn’t mean you have to discount the price.  Offering an incentive like a free TV when a guest books long term is another good way to get the guest to work very hard to get their HR department to cover their stay.   I have a guest that has a service dog that they didn’t tell me about and I’m trying to evict them, what should I do?   This caller is creating a difficult problem for themselves by trying to evict the guest. If it’s an actual service animal, they may just want to leave it alone. If the animal ends up damaging the unit, they can deal with it then.  Since the guest has a service animal and the caller has caught them, they can now go to them and communicate that there are other rules that need to be followed. If they are going to call the animal a service animal and not follow service animals rule, then he may have something to work with.   What are ways to market your short term rental business, and how do you become a student?   You become a student by starting with the presentation at There are two products available. The Blueprint is meant for students to learn how to get their first unit, the Mastermind product is for those students who are ready to scale their business.  In terms of marketing, the most important thing is to first understand who you are serving. Once you know that, you will know where and who to market to. Don’t even consider marketing until you understand your customer.   With the TV incentive, do you send it to their home address?   We just drop it off at the unit and let the guest figure out how to get it home.   I’m looking to buy linens in bulk, any suggestions?   Go to to get a 15% bulk discount for Cashflow Diary students.   Do you allow your students to use you as a reference?   We want you to be your own person, even someone new to the business shouldn’t need a reference from J. Getting into the Mastermind product will give you the specific approach to use and have the confidence to deliver the results so you won’t need a reference.   What do you do when a guest has rental remorse?   We simply stick to our cancellation policy and enforce it.   When should we use VA’s?   Since the caller is just getting started, they can comfortably run the business themselves until they have somewhere in the ballpark of thirty units. Doing the work himself initially will allow him to develop a system and SOP’s for how he wants to get the work done. Once he’s grown enough (or has had enough with dealing with guests directly), he can consider bringing on VA’s to help. J didn’t start running 24 hour coverage until he already had twenty units. At that point, it’s possible to run the business with a minimum of 5 individuals working 40 hour weeks. Links: Thank you for listening! If you enjoyed this podcast, please subscribe to the show on iTunes and Stitcher Radio!
If you’re thinking about starting the “Airbnb process” and aren’t sure if you’ve missed the boat, listen up. Real estate is changing but it’s not too late. Airbnb is just one of many marketplaces that we use. Short term rentals are here to stay and if you want to learn how to build your real estate portfolio, now is a great time to start putting the systems in place. Questions and Answers   I’ve been able to get the landlord to agree to the short term rental business model in general but I’m not sure I can make a profit, what should I do?    Step one always comes down to understanding who it is you want to serve. When you focus on who you want to serve, one of the criteria you’re looking at is their income. That will help you understand what area of town to be in and how much they will pay for certain experiences. All your streams of income will be based on how much income your ideal guest makes.  Once you know all your potential areas of revenue, you will be able to subtract out all those things and complete the picture of profitability. It can be difficult to use aggregated data to determine what your prices should be. The spread is so wide that it’s not very useful for identifying a specific case like your listing. Once you complete the exercise of figuring out who you’re serving, it becomes much easier. Keep in mind that your revenue is much more than just your room rate.   How do I automate my messaging system?   Lodgify has a rudimentary system for messaging. What we do to shortcut that is provide our guests with a link to an electronic house guide where all the relevant data is included. Everything except the dynamically generated door code because we still want to be able to maintain control of the access to the unit.   A question about a listing review   The caller’s photographer did a good job on the photos for the listing. Since the caller has followed the system closely most of the details are on point. One area that could be improved on is the copy detailing the neighborhood. Your listing is your first line of customer service, if you answer the question before the person asks you have one less question to answer later on. This can really help save time once you have a number of different units.   Which program should I consider to learn how to manage resort properties?   In terms of execution, resort units are very different from residential. In some ways resort units are easier because the kinds of customers you are serving are more obvious. For this particular caller and his thirteen units, the Mastermind Product is his best choice. Go to to learn more. When it comes to negotiating with the owner of the property, the structure the caller is using is the same one that we use. If the owner wants a cut of the business, they have to be able to contribute more than just the space. Otherwise, renting the property from them is the right way to go.   How do you dynamically generate a door code?   It depends on the platform you’re using. Sometimes the software you’re using can integrate directly via an API to create the door code, other times a personal assistant can do it.   What’s the difference between leasing an apartment under an LLC or my own name?   The difference between the two is in who is doing the business. What it comes down to is if something goes wrong, who does the landlord have a claim against? You or your LLC? If you’re trying to accumulate assets, it’s generally best to use an entity to shield those assets.   Is it too late to start the Airbnb process?   We are not in the Airbnb business, we are in the short term rental business. Airbnb and the rest are marketplaces. It’s not too late but you also have to understand that real estate is changing. Many of the established players in the industry have begun to mimic Airbnb because of these changes.  Even how we transact real estate is changing due to the technology involved. It’s only becoming more liquid as technology makes the process of transacting faster and easier than ever. Just because you didn’t recognize the change before it started doesn’t mean it’s too late. If anything, now is the perfect time.   How are you doing Homeaway pricing?   Right now, Homeaway pricing is being done updated twice a day based on comparable pricing on a set of properties within the software.    Did the automated messaging templates come out yet?   Not yet, but existing Mastermind students will have access to the templates very soon.   A note on the upcoming holidays   Now is the time to earn some additional revenue and create really great experiences for people. Make sure your security measures are working and everything is up to date. What could happen is not something you want to have happen. Get everything lined up including your pricing, inventory, and team now so you can take advantage of this time of year.    Are there effective ways to approach companies directly about bookings?   There are a number of ways to go about this. The front door method is to look up Concur customers in your area. They are already potential customers for your business. If you’re using the system we suggest, you can also create a promotion that incentivises your guest to refer you to the person that arranged their travel. If they are corporate travelers, they know exactly who you need to talk to and that’s a great way to get your foot in the door. Links: Thank you for listening! If you enjoyed this podcast, please subscribe to the show on iTunes and Stitcher Radio!
Shawn Harper is a former American football offensive tackle in the National Football League. Harper was drafted by the Los Angeles Rams in 1992. He also played for the Houston Oilers, the Indianapolis Colts, and three years in NFL Europe with the Amsterdam Admirals and Frankfurt Galaxy. Shawn Harper appeared on the hit MTV show Made. He has helped transform thousands of corporate environments, built leadership, trained teams and impacted youth development in schools, and churches with high energy keynote speeches that activate winners.  Shawn Harper is the bestselling author of The Winning Edge: 8 Principles That Will Bring Out the Winner in You! and founder/CEO of American Services and Protection, which has provided Ohio small and medium-sized businesses, corporations, municipalities, non profits, government agencies, colleges, and universities and organizations with a wide range of security solutions that focus on providing highly-trained professionals, tailored to the specifics of each job.  Podcast Highlights   Who is Shawn Harper?    For Shawn, it’s very hard to define who he was looking back from today’s perspective. We tend to gloss over the story in the process of becoming who we are. Shawn was plagued with setbacks and adversities in his youth, he was actually voted most likely to fail in school. Adversity can make you or break you. Shawn’s school days were tough and early on he believed himself to be the loser that everyone else thought he was. It wasn’t until he changed his mindset from victim to victor that everything changed. Never allow people to create your world because they will always create it too small. When Shawn made the decision to focus on his dream of playing in the NFL instead of listening to what other people thought he was capable of, nothing was the same. Once you change your focus, you change your life.   What was the transition like from playing football to the world of business?   In the case of the NFL, there is an established system in place for growth and development. For many people, when they leave that team and system to go do something else on their own the result is usually failure. Even superheroes have friends and support to help them achieve their goals. When athletes leave the game, they must build a team and find mentors to help them in the new arena. That was the secret to Shawn’s later success.  It took years for Shawn to come to that realization. All success in life comes from people having a team around them.    Playing To Win   We are created to win. Your perspective is everything in this regard. We are attracted to winning and nearly everything we do is geared towards winning. In third or fourth grade we are introduced to a different concept called success. Success teaches you production, but winning teaches you re-production. Successful business people are productive, but winners scale their business. A lot of people get dismayed, depressed, and angry because they know they are successful but deep inside they know they are not winning. Winning has been hijacked by success. The secret is to start moving, get out there and start connecting with people in whatever domain your win happens to be in. If your win is mentoring small business owners, start connecting with small business owners! The way you motivate or encourage one person, is not how you will motivate or encourage another. You have to find your team’s pain points and motivations and learn how to speak to them as a leader, because everything comes down to people.    Is where you are today something you could have envisioned?   Shawn had no idea he would be where he is today. There is a major difference between your image and your identity, but if you’re not careful you will buy into other people’s perception of your image instead of who you really are. Most of Shawn’s life he was caught up in everyone else’s image of himself. It wasn’t until he started building skill sets to define his identity that things changed. If you can walk in and apply your concept of winning a little bit every day, then your perspective on who you are and what you manifest changes. All actions stem from thoughts, and all thoughts from belief systems. Your belief system is nestled in your self concept and you always manifest your self concept. Don’t let missed opportunities define you, stay focused on your goals.   Getting Past Failures   One of the greatest advantages athletes have is more than just experiencing failure on a common basis. It’s the team around them that keeps pushing them on and encouraging them. When we’re alone, we’re much more likely to hang up the cleats when we fail, but a team can provide the motivation we need to push through. Even leaders need encouragement from their team. To have that person in your life that believes in you is vital, because without them life will chew you up and spit you up. Reference: The Winning Edge: 8 Principles That Will Bring Out the Winner in You!, Shawn Harper   Shawn’s Takeaway   Three words haunt Shawn: Wish’a, Could’a, Should’a. You can not live life comfortably, because if you’re not careful your comfort zone will become your casket. You will get knocked down but failure is your friend. Learn from the failure and get back on the bike. The average millionaire has filed for bankruptcy three times, don’t give up. Links: How To Win Friends And Influence People Thank you for listening! If you enjoyed this podcast, please subscribe to the show on iTunes and Stitcher Radio!
Get unstuck and get one step closer to making short term rental real estate a real thing for you. Get answers to your questions so that you can keep moving forward towards your financial and business goals.  Questions and Answers   We are entering into the slower winter season, what additional things can we give to our guests so they book with us over others?    The first time experiencing a slow season can be a challenge. The caller has been leveraging his membership with his local BNI group which is a great place to start. Another potential avenue is to connect with the travel agent in the group and ask them about working together. It’s possible to start generating instant book specials that allows you to acquire a guest at your advertised rate while also creating a referral for the travel agent.   How would you pitch to a BNI group?   It takes a while to get any sort of response from a BNI group because their reputations on the line. As you build your relationships in that group you want to focus on creating a power team, where each individual has different strengths.  Think about your centers of influence, like doctor’s offices that are members of the BNI group and start building those relationships.   How do you deal with a secured building?   There is a module is the Mastermind Course that members of Cashflow Diary can access that helps with this issue. The key question to ask is “if I order food, how does the food delivery guy get to the front door?”. Whatever the process is, that’s how your guest will access the unit.   How can we have properties in a state that we are not even in?   To have a property all you need is a lease, so it doesn’t matter where you are located. If you run the system properly, it only takes around an hour a day of your personal time to manage your business. If you have to do everything yourself, you don’t really have a business, you have a job. With the short term rental model the business is completely location independent. That being said, start where you live.   How would you offer the instant book special on the platform?   You would simply change up the title and description of your listing to describe what your extra offerings are. It’s also possible to set up an automatic sequence that connects the guest to your offering once they make a reservation and then sets up the connection with the travel agent as well.   How soon should I be negotiating for first right of refusal for a property?   Since the caller is willing to purchase the remainder of the units in a multifamily property, it should be very simple to ask the landlord for the first right of refusal if at some point in the future they consider selling. Now’s as good a time as any to start negotiating.   What are your feelings about incorporating in another state?   This is not legal advice, but since the person resides in California incorporating in another state may save them some costs. They should consult an attorney.   What are some ways to identify the city and zip codes near me so I will be profitable?   Rather than focusing on the money, think about the person you are going to serve. Profits can become a function of additional services regardless of zip code. Think about what your customer is coming to do, and then think about how you can be near where and what that is. That will tell you what area you should be looking at.   Do we have a master tech guru playbook?   Most of this information can be found in Module 3 of the Mastermind Course. Once you work through the info you may not even need the tech guru.   How can I find a runner to do some physical tasks?   You will have to go through a number of vendors before you find the right one to handle your physical operations. It’s unavoidable but necessary to do the work.   A question about a short term rental opportunity   The caller is considering an opportunity to create a short term rental in his parent’s basement. The caller should look up CPTED if they go this route to make sure the unit itself is more secure. He would also have to consider the noise levels and if that would be an issue. Trash will also become a challenge. One of the caller’s concerns was the walk score of the unit, but that may not be an issue depending on who they want to serve and what those potential guests expect to do. Between the two units, the only difference is the commitment, since he will be spending roughly the same amount of money. A good resource to check out is episode 320 of the Cashflow Diary podcast.   How do companies have multiple units in Denver when they only allow one primary resident?   These companies are much larger and usually VC funded, but they are running a very similar model. In the case of Denver, always read the ordinance because most of the ordinances will cover the where and the how. Very few of them completely restrict the model entirely. Short term real estate is often zoned differently and is not covered by the ordinances posing the issue. A minimum stay requirement can also help you deal the problem.   Do you think a short term rental with a walk score of 0 can work if it’s a 20 minute drive to most local attractions?   The short answer is yes. It’s not about the real estate, it’s about the experience on the piece of real estate. A walk score does not determine whether a property will work or not.   Can I get a cosigner to get an apartment and what percentage is good to return the favor? What happens if the landlord learns that the property is being used for a short term rental?   We always operate transparently, the landlord should already know what the intent is so there are no surprises. A cosigner is definitely an option. Check out the Mastermind Course to find out more and listen to episode 548 of the Cashflow Diary podcast.   I just started Airbnb three weeks ago and am having a challenge of not having any guests?   We don’t do Airbnb, we’re in the short term rentals business. Airbnb is one of the marketplaces that we use to market the business. In the case of not having guests, without knowing what system you’re running it’s hard to give specific advice. The first thing is to always start with who you want to serve and then building your business out from there. Check out to learn more.   How much would you pay a virtual assistant and for how many hours a day?   Instead of just hiring a virtual assistant, you should think about what role you want them to play. In J’s case he has a team of managers and customer service agents that are available 24/7 that he sourced through Links: Thank you for listening! If you enjoyed this podcast, please subscribe to the show on iTunes and Stitcher Radio!
Taking the right photos can make or break your short term rental listing. In today’s Q&A episode of the podcast, we do a full review of a caller’s listing photos and everything their designer and photographer did right, and all the things they did wrong. We also cover why it’s so important to have your spouse on board with your business, as well as the pros and cons of bringing cleaners in house. Questions and Answers   What is the best way to see if the HOA is okay to turn my home into a short term rental?    The best way to figure this out is to read their Covenants, Conditions & Restrictions (CC&Rs). They will typically let you know what they like and don’t like, be aware they may not use the words “short term rental” but they will probably mention something along those lines.   A question about setting prices across multiple platforms   The caller currently has Price Labs connected to Lodgify, which is then connected to and Airbnb. In order to change their prices between and Airbnb, the caller needs to take Price Labs and connect it directly to Airbnb. Once that’s done, she can create a child listing in Airbnb.   I have some photo violations on my listing, what should I do?   It appears that the caller’s designer and photographer need to make some changes. Photos where the angle is not level or where the property appears dirty because of poor lighting are going to be major problems. Be aware that when your photographer uses HDR, it’s going to reveal lots of imperfections so it’s probably best to avoid it.  If you’re not providing a laptop with your rental, don’t take photos with a laptop in it. People will make assumptions about that sort of thing. Same goes for sheets and towels of different colors. Avoid lights that don’t have a daylight balance for your photos.  Short term rentals are a review based business, and reviews are primarily about setting the correct expectations at the beginning. Poor photos can end up costing you money, because what you photograph is what your guests will expect. If you deviate from that, that’s when you run into bad reviews. Be careful with the wording on your post as well.   What are your thoughts on the Airbnb custom URL link for listings?   It’s a band-aid at best. You want to have control and if you’re going to take the time to promote a listing, you should drive that traffic to your domain. That’s what is going to build your business long term.    The importance of having your spouse on board   As entrepreneurs, we tend to believe that things will work out for us. It’s just how we’re wired. Having a spouse whose perspective you trust on your team will make a huge difference for you. If you’re spouse is not already on board, keep in mind that they are mainly concerned with whether or not they will be okay, especially at the beginning of a new business.  This business is a team effort, just like raising a family. Make sure they know what contribution they are making, because without them, things would not be where they are. Go find your right hand person.   What calendar rules should we set for the holidays?   When it comes to the holidays, your calendar rules have a lot to do with your staff. Are they okay with working/do they celebrate those holidays? We don’t mind arrivals on a holiday, but we do block people from departing on a holiday, but that is a conversation you need to have with your staff well beforehand. Minimum stays on the holiday will change depending on the holiday itself. Some people can get away with a seven or fourteen day minimum for holidays like Christmas.   Can we talk about a cleaning company versus having in house cleaners?   There are a number of things to consider before bringing cleaners in house. Being able to classify your cleaner as a contractor will be crucial to your cost structure. Part of your cleaning costs have nothing to do with cleaning, and everything to do with the organizational cost. Be very clear that you can keep them on as contractors. The other issue is scheduling. With a company, the process is simple. They have a number of people available at a variety of times when you need them. If you can have someone internally take care of the scheduling and the size of your business justifies it, then it may make sense to bring cleaners in house.  You are going to need a consistent pipeline of people to hire and train. Hospitality has an incredibly high turnover, so you need two systems in place if you go down this road. Specifically hiring and training.  Links: Thank you for listening! If you enjoyed this podcast, please subscribe to the show on iTunes and Stitcher Radio!
Comments (5)


Woooow... Just wooow.. This is the episode of episodes for sure!!! Study session has just begun! Thanks J. M Bernhard of Norway

Dec 9th


Great... Just GREAT INFO!

Oct 21st
Reply (1)

Michelle Walker-Wade

"Malarkey". lol. Thanks for helping him out with that one.

Oct 8th

Chad Robinson

great content but can you redo it with better Audio?

Jan 16th
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