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    Business

    Cashflow Diary™

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

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

    Start Learning For Free Today.

    Advertise
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    Latest Episodes:
    How To Take Good Photos Of Your Short Term Rental Listing Q&A Nov 20, 2019
    Show notes

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

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

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

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

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

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


    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 Booking.com and Airbnb. In order to change their prices between Booking.com 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:

    cashflowdiarypodcast.com

    cashflowdiary.com/star

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


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

    Dear Future Top Performer,

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

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

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

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

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

    Ready to stop bleeding money and start leading the pack?

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

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

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


    Al Williamson on the Secret Behind the Extended Stay Model Nov 06, 2019
    Show notes

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

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

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

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

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

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


    Al Williamson is a professional engineer, full-time real estate investor and the author of several real estate books. He began investing in 1996. Al is best known for publicly documenting his quest to create enough secondary income streams to cover the 1st mortgage of his eight-unit apartment building (which he accomplished in September 2015). He is now trying to figure out how to maximize the cash flow of a small portfolio so it can generate enough income to replace a middle-class job. Al is a proud family man who now spends his day managing and expanding his corporate housing business in Sacramento, California.

    Podcast Highlights

    • Who is Al Williamson?

    Before everything that people know Al Williamson for today, he was training to become a professional gymnast. That was until he broke his arm on the high bar and realized that he was going down a risky path. He switched course and learned to be an engineer and started creating things.

    It wasn’t until meeting his wife did he consider getting into real estate. He met a guy at a church picnic that turned him on to real estate investing and after reading everything he could about the subject at his local library Al realized that it was exactly what he was looking for.

    Al Williamson and his new wife purchased a triplex and it eventually quadrupled in price. That early experience brought his wife on board with the whole idea and taught them plenty of valuable lessons. He leveraged that into his next purchase where he had a major focus on cleaning up the local neighborhood. It was a relationship with a local health center that later got Al into the short term rental space.

    One of the easiest ways to get into the real estate game and put yourself into a profitable position quickly is by leveraging short term rentals.

    • Was it a challenge in making the short term rental model work in California?

    Initially the numbers didn’t work out for Al because of maintenance costs. Owning property is a great way to build wealth but a bad way to generate income because something is always broken that needs to be replaced. You don’t get to keep the money because it has to go back into the property until that debt service is finished. In a lot of ways, short term rentals were the answer to Al’s problems.

    There are a number of different ways that short term rentals solve the issue and there are tons of opportunities to increase your cash flow. By experimenting with one unit for short term rentals Al was able to generate the same net income as his three other units. The extended stay model is changing the way Al is structuring his business because the trend of people wanting to live in one place and work in another is taking off.

    • How do you market for long term guests?

    Al has 14 different marketing strategies that he uses to bring in extended stay short term rental guests. A good indicator that your market can support the model is if there is an extended stay hotel in your area already. From there you need to get out from behind your computer and have a conversation with real people. Talking to the bartender at the hotel can yield some valuable info.

    Extended Stay America is doubling down on the one month and two month guests. It’s a big business and major hospitality companies are beginning to recognize that.

    If you’re working with Airbnb you’re going to have to put your listing together. The headline of that listing is very important and you can use that to call out the exact type of customer you are looking for. Write your headline to resonate with that person. You can also set your minimum stay requirement so Airbnb only shows your listing to people looking for an extended stay unit. Do things to separate yourself from the rest of the competition.

    There is a growing need for extended stay units in America, it’s up to the housing entrepreneur to step up and answer the demand. The type of the property is less relevant than the type of customer you want to serve. Stay in your lane and serve people like you because you will have a better understanding of what they need and want. You will make the same net income.

    You can make your decisions based on gross income, which many people do, but only the net income really matters. You can make different decisions and save yourself a lot of time and energy and still make the same net income.

    Most ordinances were written to slow down transient rentals and prevent them from competing with the existing hotel businesses, but they are not intended to affect month to month rentals. Month to month rentals are the cornerstone of affordable housing and they know it.

    • What are some differences you’ve seen between people running a less than 30 day stay business and a greater than 30 day stay?

    The less than 30 days operators are looking at serving tourists and convention goers. For the people focusing on more than 30 days, they are thinking about other features that are important to a different crowd. Things like parking and laundry facilities. They also get the advantage of business travelers being more forgiving and easy going in general because they aren’t paying for the stay out of their own pockets.

    • What are some alternative ways to attract your target market?

    Facebook has been very effective, having your own group is a good way to let people know what you’re offering. Al also has his own website which has been a good tool in attracting extended stay guests. When you’ve been in business for over a year, your reputation starts to do some good work as well.

    Al has eight different categories of customers that he caters to: vacation renters, military housing, student housing, insurance housing, corporate rentals, people in between selling their homes, and international housing. There is also medical housing that’s broken down into three different types as well. You can take those categories and figure out which one you want to dominate and then start growing your funnel for that category.

    • How do you avoid having to evict or grant tenancy to someone?

    Al hasn’t had to evict anyone because he mainly serves business travelers and they are just not going to stay. Even if they did, if they’re happy paying an elevated rent than what’s the problem?

    The main purpose of a lease agreement is to turn a transient into a tenant, which means the relationship is governed by a different set of laws. If you do that, then all the ordinances and laws around the typical short term rental transients no longer apply.

    • What are the special services you’re offering to increase your net income?

    Al started off by offering a menu of cleaning services to guests b...


    The AirBnB Way with Joseph Michelli Nov 04, 2019
    Show notes

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

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

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

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

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

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


    Dr. Joseph Michelli, Ph.D., C.S.P., is an internationally sought-after speaker, author, and organizational consultant. Dr. Joseph Michelli is the author of numerous national bestsellers, including The Starbucks Experience: 5 Principles for Turning Ordinary Into Extraordinary, The New Gold Standard: 5 Leadership Principles for Creating a

    Legendary Customer Experience Courtesy of the Ritz-Carlton Hotel Company, and the New York Times #1 bestseller Prescription for Excellence: Leadership Lessons for Creating a World Class Customer Experience from UCLA Health System.

    He was named as one of the Top 10 thought leaders in Customer Service by Global Gurus. His new book is The Airbnb Way: 5 Leadership Lessons for Igniting Growth through Loyalty, Community, and Belonging. Dr. Michelli is an opinion columnist for the CEOWORLD magazine.

    Podcast Highlights

    • Who is Joseph Michelli?

    Joseph was a kid raised in a small town in Colorado and his parents imparted a key lesson to him when he was young. Namely, the responsibility of being raised in that family was that he would give more to the world than he took, and if he did the world would give more to him than he could ask for.

    Being accepted into graduate school was quite an achievement for Joseph, no one else in his family had graduated from college at the time. He was pretty focused on his own success in his career for a while until he realized that it wasn’t really about him at all, it’s about telling the stories of the clients he worked with as a consultant. Ultimately, those experiences helped Joseph write books about other people to tell their stories.

    All of the art of success is taking great principles and celebrating the victories of people you work with and people who are doing inspiring things in the world. The world is hungry for uplifting positive leadership and tools that enable them to experience their own greatness.

    • Inspiring Greatness

    We are in a world where short term rentals have blown up and AirBnB is a point in that journey. They created a marketplace that unlocked incredible potential for millions of people and now they are on the same playing field as historical giants like Marriott.

    • What is hospitality?

    Hospitality is taking the basics of service like being responsive, acting with urgency, get it right and make it right, and consistency, and then adding on the understanding of human needs that go beyond a transaction. It’s about an emotional experience where someone cared for and about me in a world that is often very lonely and strange.

    The real estate itself is the table stakes of getting into the game. The experience is far more important and that’s the element that’s missing in the corporate way of doing things. In many ways the big hospitality companies are trying to emulate the more successful short term rental operations.

    Solopreneurs will always have an edge over massive businesses because they’re more nimble and can provide a more personal touch. A smaller player can always be a more personal player than any large service provider.

    • AirBnB vs The Old Model

    AirBnB looked for people with the expertise and sought them out as mentors. A lot of AirBnB’s success is in the practice of looking for mentors and seeking out information from people that know more.

    Part of the notion of seeking insights from someone else is in seeking community. Hosts in AirBnB do more than offer a place to stay, they create jobs and opportunities in the community they operate in. One of the things that AirBnB has done really well is in advocating for short term rental rights.

    Loyalty comes from helping guests feel something. AirBnB is selling belonging as part of the experience. If operators drive loyalty back to the platform that will keep driving revenue back to them.

    The host community is on the whole very welcoming but there is always a subset of the population that wants to live out their prejudices. AirBnB has taken steps to correct that tendency and police the one off incidents. It’s a work in progress but the situation is getting better.

    There is a need to be a responsible host so some level of regulation seems to be necessary. The issue is when regulations become overreaching and start dictating what people can do with their own property. There is an incredible amount of industry that is being created by the short term rental space.

    • What are some potential pitfalls of the growth of the short term rental space?

    Regulations are certainly a concern, a lot will depend on what happens when AirBnB goes public next year. Market share will be an issue they need to deal with in the near future as well. Scandal is another, some brands become big targets for entire industries.

    Reference: The Airbnb Way: 5 Leadership Lessons for Igniting Growth through Loyalty, Community, and Belonging, Joseph Michelli

    • Joseph’s Takeaway

    First and foremost, you have to say you have something of value to create in the world and you are going to define that value clearly. It’s always a matter of understanding the market and then articulating the value that you bring to it. Business is not as complicated as we make it out to be. Just go and start and keep in mind the five dimensions of a successful business.

    Links:

    airbnbway.com

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


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

    Dear Future Top Performer,

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

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

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

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

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

    Ready to stop bleeding money and...


    Innovation in Healthcare, Boon Is Changing The Game Nov 01, 2019
    Show notes

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

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

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

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

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

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


    Ryan Vet is an innovative leader, entrepreneur and author. He has presented to audiences around the globe on four different continents on leadership, marketing and reaching your maximum potential.

    Ryan’s experiences range from start-ups to well-established multi-national, Fortune 500s. From starting his first business at age 14 to launching and successfully exiting start-ups, Ryan is a serial entrepreneur. Currently, Ryan serves as the CEO of Boon—an on-demand, temporary healthcare staffing platform (imagine Uber meets eHarmony meets healthcare staffing). He has been featured in countless publications for his entrepreneurial endeavors and has been inducted as an official member into the exclusive Forbes Communication Council. In addition, Ryan hosts The Dental Experience Podcast.

    As an experiential marketing and branding consultant Ryan has worked companies from start-ups to iconic household brands. And in his spare time, he co-owns a series of craft beverage lounges called The Oak House. Ryan also sits as an advisory board member for a number of organizations including Elon University’s Doherty Center for Entrepreneurial Leadership

    Podcast Highlights

    • Who is Ryan Vet?

    Ryan has always loved creating and it’s been at the core of his career. His first real business was a lemonade stand where he learned how to diversify his products and captivate his audience with marketing. Somewhere in between his petting zoo and his lemonade stand, Ryan also developed a trading card business at the age of 11. It was a long journey from the lemonade stand to Boon.

    When Ryan was younger, some local businesses realized that he had some talent with websites and basic graphic design and this actually lead to his first real business. He built a marketing company that served 200 clients in 25 different countries, and eventually this led to his first startup software company. Every startup yielded additional skills and connections that allowed Ryan to build his next business.

    One such startup was in the medical and dental space. Ryan began building his platform and started speaking at dental conferences about patient experience. It was there that he saw a common need for staffing. About a year and a half ago he started researching how to provide temporary team members for the medical industry. During the research he found that the industry size of medical staffers was 16 times the size of Uber and Lyft combined. Boon is the system that Ryan came up with, it provides innovation in healthcare that allows hospitals and health care providers to connect directly with practitioners that are open and available.

    • Not Taking No For An Answer

    Ryan’s always had a driving passion to get things done. If Ryan wanted something, his parents rarely told him no but they also didn’t get him things very often as well. Ryan had to earn the money to get the things he wanted and his parents would help him out.

    If more people interpreted “no” as “not yet” or do it yourself, more products would come to market.

    • Why did you get into software?

    At the advent of web based software, Ryan found his passion for enabling people to solve their problems using technology. He wanted to be able to use platforms and apps to solve people’s problems.

    • Digitizing vs. Innovating

    Ryan’s first start up was straddling the line between digitization and innovation. He learned it’s relatively easy to create a process or app that streamlines something, but now Ryan is trying to stay on the side of innovation. Digitization is relatively easy and valuable but innovation is transformative. The iPhone changed the cell phone industry completely.

    Ebay is an example of digitization, it’s basically an online garage sale. Amazon is an example of innovation in that they enable everyone to be a retail owner. Boon is striving to be more like Amazon.

    One in ten healthcare providers are temporary workers, and there are plenty of issues with the traditional model. It takes a long time, it costs a lot of money, people are not getting paid fairly or access to benefits, patient care with temporary workers is not always at the forefront, and the people are not always matched well. Boon addresses all those issues.

    • Where does someone get the capital to develop software and what was different about this idea that gave you the confidence to start looking?

    Ryan has funded a business nearly every way it’s possible to do so and it’s probably the hardest part about building the business. The rejection rate is high and it’s hard to push through, but anyone is capable of raising money if they are willing to get rejected 99 times before they hear that yes.

    Practicing good is part of Boon’s cultural DNA and equity crowdfunding aligns with that goal. Prior to the Jobs Act the average person had no opportunity to invest in startups, but now there are opportunities for people to invest in startups for as little as $100. Boon went with a company called Wefunder to bring people into an equal opportunity investment.

    There is a lot of value of having potentially hundreds of investors in your company. They offer a number of different perspectives and connections that you wouldn’t otherwise have access to. In Ryan’s experience, the majority of investors aren’t interested in reaching out and it’s more passive for them.

    • Innovation in Healthcare

    Boon is constantly working on new products and services to offer, and that includes looking at different industries and verticals. It’s not limiting itself to innovation in healthcare. A new chapter of Boon is taking what they’ve already accomplished and expand that to any industry that is willing to have it.

    There have been a lot of conversations around the nature of the employment. Boon is predicated on fair pay and access to benefits, they are one of the few gig economy platforms that does.

    • Ryan’s Takeaway

    Being a leader and an entrepreneur in the business space is extremely lonely. You have to make decisions the best you can, and not everybody is going to be a fan. You need to surround yourself with three people. A forerunner, someone who has been where you want to go and can help you avoid the same mistakes. A running mate, the person you can run with that will help you make leaps at the same time by holding your hand and jumping with you. And finally, people who are a few steps behind you. When you starting mentoring and sharing what you’re doing with people who are just behind you, you synthesize your knowledge in a different way and make your advice actionable. When you mentor someone you become more insightful into your own journey.

    Links:


    Francis Greenburger on Risk, Real Estate, and Business Oct 30, 2019
    Show notes

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

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

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

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

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

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


    Francis Greenburger is the legendary real estate developer who is Chairman & CEO of Time Equities and owner of the literary agency Sanford J. Greenburger Associates, which has represented noted authors such as Dan Brown, James Patterson, Nicholas Sparks, and Nelson DeMille. He is the founder & chairman of Art Omi (previously Omi International Arts Center) and The Greenburger Center for Social and Criminal Justice, and the bestselling author of Risk Game: Self-Portrait of an Entrepreneur.

    Podcast Highlights

    • Who is Francis Greenburger?

    Francis Greenburger grew up in New York City where his parents were upper class but his father as a solopreneur never really made a significant amount of money. The first thing that Francis was blessed with was the confidence of his parents in his ability to achieve his goals. That went together with his natural knack for business. He started working for his father after school when he was 12 years old. His innate qualities gave him the early characteristics and motivations to be an entrepreneur.

    One of the things that Francis has said is that if you don’t like risk, you shouldn’t be an entrepreneur. For Francis, risk is just part of the gig.

    • Do you see any parallels between cell phones and digital communication and the advent of television?

    The evolution of digital communication has changed the nature of communication. It’s also made it more personal with social media and email, there is a lot of interpersonal communication happening now. Humans have a basic need to communicate and now there are more ways than ever.

    • Parental Confidence

    There are certainly people who have parents who are not encouraging or present. Francis recalls a comment made during a tennis match, where two different players of equal skill are compared, and the observation was that the deciding factor will be self confidence. Having parents that believe in you alongside his mentors empowered Francis and gave him the confidence to face the challenges that all entrepreneurs have to face.

    The buy in that someone gets from mentors they respect can be very empowering and confidence building, even when parents haven’t provided that.

    • What do you consider risky?

    Francis uses the term “intelligent risk” to describe the process of evaluating risks. Intelligent risk is not a gamble, it’s a calculated and measured action with research and analysis behind it. Francis has a theory that if you’re going into a generic marketplace where you are just offering more of the same, it’s very hard as an entrepreneur to compete on price and that’s all you’re really left with. Look for markets that aren’t being addressed and try to find solutions to meet those unmet needs.

    Imagine what you could accomplish if you weren’t afraid to fail.

    • What would you say are unaddressed needs in the real estate space?

    Under occupied office buildings are one such issue. Sometimes an office maybe be under occupied because of a reputation problem from the past but it may have the features that allow you to lower your cost basis, which means you can also rent out the space for less. These can be the ingredients that allow you to be competitive in the market.

    • Why did you go into real estate?

    Francis has a memory of walking down 5th Avenue in New York City and realized that he had an innate sense of architecture. He got into the real estate as a byproduct of his book business. Francis had rented an office that was too big for him and managed to sublet half of it at double the rent he was paying.

    Francis was involved in his father’s literary business at the same time as he was building his real estate business. For about 10 years Francis split his time between the two ventures. Francis typically works 12 to 13 hours a day which is his natural mode so that probably gave him an edge in business. For Francis, hard work is part of the formula for success.

    • Do individuals starting out in real estate have it easier today or harder?

    Francis’s sense is that the business has become more complicated over time. You need to have a lot more expertise to make real estate work which is why it’s really a team sport. To do you it professionally you need to be part of a group that has that expertise.

    If you’re young and you go to work for a real estate company that can help you out because in a way you inherit some of their credibility.

    • Is there something people should do differently if they are just starting out in their career?

    If you really want to advance your career you have to spend time in a sophisticated real estate environment in order to learn the expertise that gets deployed on the complex problems in the business. Once you have that knowledge you’re much better equipped to go out on your own.

    Francis’s company tries to be a platform for talented entrepreneurs to set up their own business.

    • How difficult was it to put all of your knowledge into Risk Game?

    Initially Francis believed that he would have to write four different books. Lucky for him he met a talented writer that put everything together into a cohesive narrative and a solid book.

    Enlisting talented help is a common thread in Francis’s businesses. Bringing in people with expertise and experience enrich the business because in combination we are stronger than on our own.

    • Have you ever had a partnership that failed and how did you deal with it?

    When undertaking business ventures you’re always going to encounter a certain amount of failure but you can’t be discouraged by it. There are people and business partners who will disappoint you. In Francis’s case, he has benefited much more than he has been upset by such failures.

    If you’re not failing in 10% to 20% of your ventures, you’re not taking enough risk. You have to be able to tolerate risk and accept failure, learn from it, and move on.

    Reference: Risk Game: Self-Portrait of an Entrepreneur, Francis Greenburger

    • Francis’s Takeaway

    Most people who are entrepreneurs have dreams of one sort or another. Think about your best idea and try to put it into action. When obstacles have to be overcome, devise strategies to overcome them. In real estate, look at a number of properties not just one. Buy it right, it’s the only chance you’ll get. There are always challenges but for every roadblock there is a strategy for success to get past it.

    Links:

    Risk Game: Self-Portrait of an Entrepreneur ...


    Self Directed Retirement Accounts with Rocket Dollar Oct 28, 2019
    Show notes

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

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

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

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

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

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


    Dan Kryzanowski is an active real estate investor and fundraiser, leveraging Self-Directed accounts - SDIRA and Solo 401(k) - to create a diversified real estate portfolio yielding double-digit returns. He specializes in self-storage investments, multi-family and hard money residential property loans. Dan has personally raised millions of dollars from family offices and individuals, and empowered his partners to raise seven-figures on multiple occasions.

    Dan serves as Executive Vice President at Rocket Dollar, unlocking the $10T pool of untapped retirement assets for the real estate community. He is also a Capital Partner for Pinnacle Storage Properties and Corporate Board President for Hugh O'Brian Youth Central Texas. Dan, a Wharton graduate, previously led commercial real estate initiatives for GE Capital in Mexico and South America.

    Podcast Highlights

    • Who is Dan Kryzanowski?

    Dan attributes his business success to his magic afro and his early basketball success. Dan had a very blessed life for his first 30 years, he followed what would be considered a pretty normal path that most people in his generation would follow, right up until the crash of 2008. That made him rethink things a bit and Dan found that he wasn’t particularly interested in working for General Electric for the next 30 years of his life. He and his wife moved back to Texas and started looking at alternative investment.

    There were a few signs that GE wasn’t going to be a great place to spend the rest of his career at. Ultimately it was a personal decision to change the path from following everyone else and being led by fear or having the confidence to do things on his own.

    • Why Real Estate and self directed retirement accounts?

    While working his traditional career Dan had always been interested in things he could do with his 401(k). When he had a fateful conversation with a guy that flipped houses at a wedding, Dan was exposed to the world of self directed retirement accounts.

    Once he realized that there were a number of benefits using your retirement funds to invest in real estate, it all just made sense. Instead of making 2%-3% with a traditional bond or fund, he can earn double digit returns working with someone he trusts and can look at the real estate and see the asset. Using self directed retirement account was the key that unlocked everything.

    The idea has been around since the 70’s. Self directed retirement accounts are where you take full control of where your retirement dollars go. There are an infinite number of investments you can access and there are no fees or early withdrawal penalties.

    Rocket Dollar has completely eliminated the friction involved in using self directed retirement accounts to invest. Dan’s company is very focused on education and informing people the options that are available to them. You have full control of your money at all times for a low monthly fee.

    If you’re self employed, you are eligible for the Solo 401(k). Not only can you contribute ten times as much as an IRA, you also get full checkbook control by default.

    • What if my HR department said my 401(k) is already self directed?

    By one definition your 401(k) at work is self directed, but it wouldn’t count as Self Directed. You get a handful of choices in what you invest in but you don’t have true freedom in where your money goes. You won’t be able to invest in a private real estate deal or something exotic like cryptocurrency.

    People want to be on the same footing from an education standpoint. They want to know what the rules and opportunities are, which is what Rocket Dollar is aiming to provide.

    It’s been a rule of thumb that you can’t touch your company’s 401(k) until you are 59 and a half and sadly there isn’t a real responsibility on the company to offer all the options. Most middle age high earners have a few IRA’s or 401(k)’s from past employers hanging around, and once they are made aware of this they can roll that money into a self directed retirement account and put that money into real estate.

    • What are some of the creative places that people want to put their money?

    Bars and restaurants are common passion projects for people to invest in. Dan has had some good experiences with female entrepreneurs doing some very interesting things in the market. Diversifying into different kinds of investments like cryptocurrency and self storage are becoming more common as well.

    Rocket Dollar is not a match maker, they are a facilitator. They are focused on giving people the opportunity and knowledge to invest in a variety of things. Simplifying the transactions is in a lot of ways exactly what the marketplace needs.

    • Is there a specific focus at Rocket Dollar to help syndicators raise money?

    Yes, Rocket Dollar will draw attention to possible investments like syndications in order to make it easier for people to raise the funds they need. They are very close to making it as easy as transferring funds quickly and easily using your mobile phone.

    • Dan’s Takeaway

    Go to Rocketdollar.com/learn and start learning. Most people will be able to self educate and get 90% of the way there even if they are completely unfamiliar. Once you do that, reach out to the sales team and talk with us about how we can help. Self directed retirement accounts aren’t going anywhere and there are a lot of opportunities available for people who take action.

    Links:

    rocketdollar.com/cashflowdiary

    dan@rocketdollar.com

    Get a $100 off your Rocket Dollar account with the code Cashflowdiary19

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


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

    Dear Future Top Performer,

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

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

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

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


    October 2019 Q & A 8: Negotiations, Slow Seasons, and Protecting Yourself Oct 25, 2019
    Show notes

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

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

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

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

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

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


    Questions and Answers

    • I have a person that wants to book through February to November but I’ve already got someone with a reservation in the middle of that time. Do I offer the other guest to switch to another short term rental unit to accommodate the person who wants to stay longer?

    This can be pretty common with new short term rental units or you are new to operating. When you put up a new listing it often gets promoted and for people looking for longer stays there often aren’t a lot of options. You should offer the current reservation the option to move to another short term rental unit, even if you don’t have another unit in that particular area.

    The ideal situation would be to get all the days booked with both individuals while also getting the money upfront. The revenue from the long term reservation can actually be used to acquire another unit for the shorter reservation if necessary. There are also a number of incentives you can offer to close the deal.

    • A major cancellation issue with AirBnB

    J has had a similar situation occur with a guest that said they were going to cancel but didn’t. We continually sent the person messages as well as keeping in communication with AirBnB. In both cases we were paid in full for the days that were stuck in limbo but only because we were being hyper diligent about following up and making sure the reservation was actually cancelled.

    If you’re at the 70 bedroom stage like this caller is in, you really shouldn’t be involved in this sort of issue. Your staff should be able to handle everything. Your business should also have an established system for making sure your guests actually arrive for their reservations.

    For the caller, they need to have a customer experience manager that should be able to handle all aspects of this sort of issue. When you encounter something new, create an SOP (standard operating procedure).

    • My fear of not being sure of where to begin is holding me back. What should I start with first?

    All of our short term rental mastermind students get a six hour kickstart session with J specifically to address this problem. Outside of that, the very first question you have to answer is “Who do I want to serve?”. Once you answer that, you can figure everything else out.

    • What if I can’t find a management company for one condo that’s out of town?

    Remote management is challenging. If you are going to do it remotely you must have a cash management system in place to make sure that no money gets released without a verification that the work has actually been done. Find someone who can be your eyes and ears on a job site.

    If you can find an actual landlord in the area to assist you that has experience with rehabs that would be ideal. You can find them through the local real estate investors association or meetup.com.

    • If a guest leaves a review but you haven’t you reviewed them yet, can people still see it?

    Nope, not until either you review them or 14 days pass.

    • Are the metrics you used in the SmartBnB training available to the public?

    SmartBnB is great for their ability to see data and metrics and then use that to drive higher revenue. It’s not currently available to the public.

    • The slow season is coming, any updates on refreshing our short term rental listing to keep a higher viewing rate?

    Depending on where you are geographically, the travel season is changing which means you need to adjust to the market. That may mean adjusting your discount curve. That doesn’t mean that you have to sacrifice profit, just that you need to think about new lines of revenue. Those are things that everyone should have in place in case of an occupancy challenge.

    • How do we suggest we deal with when a guest needs an insurance payment in order to make a booking?

    Never let a guest into a unit prior to getting paid. The answer is to get paid upfront, the guest will figure out what they need to do to make that happen.

    • How often should I be checking pricing and how often should I be manually adjusting it?

    In a 30 day market checking daily isn’t really necessary. It’s more about making sure you are priced appropriately from the beginning and understanding the platform you are on.

    • Where can I find info on hiring VA’s, outsourcing, managing, and fee collection?

    Even though the caller is already experienced, they should try to approach things as a beginner. You need to start with the foundation if you want to build a proper business. Even at short term rental 8 units they probably don’t need VA’s yet if they’ve set up the right systems in place.

    • What are some tips to make it through the upcoming slow season?

    Assuming you’re in a somewhat temperate client, when it comes to slow season you need to understand that your expectation of where your revenue comes from needs to be adjusted. Go to the formula Leads x Customers x Margin x Frequency = Growth Potential, which of those can be improved upon? One of them will be a clue as to what you need to build to deal with the slow season.

    • Can you take advantage of cost segregation when doing night rental arbitration? Are there tax advantages to controlling a property versus owning it?

    Much of the furnishing can become a direct write off. For some students when they are starting off, it makes more sense to lease the furniture and preserve their capital. One of the major downsides to the whole operation is it will create a large cash flow, and if you don’t offset that cashflow with some sort of investment you will just end up paying Uncle Sam.

    • What factors matter in the negotiation process for additional units?

    It’s often that landlords that you’re working with will begin to approach you about additional units because you solve their vacancy problem. You need to be aware of the problems that you are taking off their table for them. If you want to eventually own the property, this is when you should start leveraging what you’re doing for them to set that in motion.

    • Do I setup Lodgify or Wheelhouse so I can set up my own website for direct bookings?

    We use Lodgify for just that.

    • What are the boundaries for the landlord showing up to the unit unannounced?

    There should never be a situation where your landlord shows up to the unit unannounced outside of a fire or some other type of major issue.

    • Is okay to take a lease in your na...

    October 2019 Q & A #7: Bed Bugs, Insurance, and Bad Reviews Oct 23, 2019
    Show notes

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

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

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

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

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

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


    Questions and Answers

    • How do I improve my rankings so that I can be viewed more frequently and more often? Also do you have any tips on attracting last minute guests?

    The first step is to run a Market report using SmartBnB on the caller’s location. Start making incremental changes to the pricing specifically for the available dates coming up in the future. The market report will reveal the low, high, median, and average prices for any comparable listings, you should be pricing your listing relative to the market for your available weekends.

    You should also adjust for seasonality. The change from August to September can be quite drastic. Since the optimal booking window for the caller is 25 days, it may make sense to start experimenting with the discount curve beyond 14 days.

    Being on page 11 of the rankings is basically the same as not being present at all. Look at your title and thumbnail as possible places to improve alongside pricing.

    • My closing was put off because of the hurricane, can I go ahead and list the property but not go live?

    There is a window of time when your listing is considered new and it gets a boost in exposure and rankings. You should maximize the SEO bonus when it’s available. We also have a number of students that have optimized their locations as possible shelters from bad weather or natural disasters.

    If you have a property in an area that is exposed to bad weather, a good tip is to have a generator so that your property doesn’t lose electricity when everything else does.

    • Any updates regarding automation getting agreements signed?

    J had to put this project on the backburner due to some issues scaling out the customer service team. The goal is to have two way communication through as many channels as possible. Once we’ve worked through that we’ll be making more steps towards automation.

    • What do I do about bed bugs?

    Ideally when you are building a business you want to build in systems so that your amount of time working in the business instead of on the business is as minimal as possible. Hopefully you never experience bed bugs but having systems in place will definitely help.

    We have only seen one instance of bed bugs in all the history of tenants that have been our guests. It occurred in a two bedroom unit where the guest reported the bed bugs to us. We learned that you should hire the best pest control company you can right away, even if it’s delayed by a day or two. It’s better to resolve this properly, even if it costs you some revenue.

    Before a unit is sprayed, cleaners should strip the beds, vacuum and clean the unit, and while doing it they should be wearing gloves and masks. We originally thought we would have to throw out all the linens in the unit, but that wasn’t necessary. Just bag the linens up and mark them as contaminated, the cleaners will wash them in extreme heat in order to eliminate the infestation.

    Sadly there is no guaranteed fix for bed bugs. In order to get a heat treatment on the unit we had to hire a company that can drain the fire sprinkler system. The outlets should also be dusted in the adjacent units because bed bugs move quickly and get into the walls as well.

    Another major lesson is to notify your insurance company immediately, and if possible you should be insured specifically in the event of bed bugs.

    All told, this one problem took between 40 and 50 hours to resolve. There is a lot of coordination involved with a number of different people. Students now have access to the process we’ve put together to handle this situation.

    If we include lost revenue, the total cost of the whole episode was around $15,000. Now that there is a process in place to handle things, the cost would probably be around $7,000 to $8,000. Even if you have insurance, this isn’t something that you’re going to be able to wait for them to pay for things. You will need the funds in place to take care of things in the meantime.

    • Did the insurance reimburse everything?

    No, you will be reimbursed charges related to cleaning. One of the mistakes we made was not separating our linens, this meant that we had to pay for extra cleaning to make sure we didn’t contaminate other people’s linens. It’s also very possible that you would have to replace furniture as well, we got lucky in that case.

    • How do you recover from bad reviews because of an instance like bed bugs?

    When you’re trying to recover from bad reviews, and there are a number of situations that can lead to one, one of the ways is to accelerate the frequency with which you can generate a review. The best way to do that is to reduce the maximum length of stay. This will generate a number of shorter stays and more frequent reviews, which will push down bad reviews on your listing.

    • Is there a way to create a market report on a listing that I don’t currently manage so that I can start to understand the owner might be having difficulty?

    Most people in the short term rental space don’t actually have a grasp on what it takes to run the business well. Right now you don’t have to be good, you just have to be present. Over time, as this marketplace matures you’re going to have to be good and the ones that are will build the brand that they want to and get the kinds of customers they deserve.

    If you want to be able to run a report on a property that you do not control or manage AirDNA is your best bet. You should be looking for trend data for the particular market you’re looking into and compare the listing to the surrounding area. If performance is poor on the property, it may be as simple as being on the wrong platform.

    Links:

    cashflowdiarypodcast.com

    cashflowdiary.com/star

    cashflowdiary.com/affiliate

    airdna.co

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


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

    Dear Future Top Performer,

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

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

    There's a simple yet powerful equation that's revolutionizing the STR industry...


    October 2019 Q & A 6: Why Are My Short Term Rental Bookings Declining? Oct 21, 2019
    Show notes

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

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

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

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

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

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


    Questions and Answers

    • Our short term rental bookings have been plummeting recently and I’m not sure why. Am I discounting too early or too slow based on data?

    You have to decide how far out in advance you want to be comfortable with for your bookings. To really know what’s going on you need to get the right data in front of you. In the case of the caller’s short term rental unit, the average number of guests is 4.1 with a 7 day booking window. Since all the data came from the one platform, one solution may be to get on additional platforms that will increase the booking window.

    If there is a conversion rate decline, the question becomes “what changed?”. If customer preference is what has changed, that may mean you have to adjust the way you are describing the rental and modify who you are trying to attract.

    It’s important to look at last year’s data as well so you can compare. If your conversion rate is down to 56% from 70% in Q4, maybe that’s what you should expect based on historical data. If you have the same number of leads, it may be something to do with your listing, or your communication, or your response time that is affecting your conversions.

    • For a house, do you put a camera in the backyard?

    When it comes down to an expectation that a space is going to be private you can run into issues. You can put a camera in the backyard but you should make sure it’s looking at the backyard and not into the house. If you do do it, make sure you disclose it to your short term rental tenants.

    If there’s a pool in the backyard, you have to be especially careful. You are probably concerned about the number of people coming into the unit at that point and if that’s the case there are other solutions to that problem. You could use devices that detect cell signals or wifi connections that would indicate the number of people present.

    Links:

    cashflowdiarypodcast.com

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


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

    Dear Future Top Performer,

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

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

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

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

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

    Ready to stop bleeding money and start leading the pack?

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

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

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


    October 2019 Q & A #5: How Long Does It Take To Get Started In Short Term Rentals Oct 18, 2019
    Show notes

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

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

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

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

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

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


    Questions and Answers

    • Does AirBnB work the same globally?

    The idea is the same, but some of the functions will be different. For example, payment systems will be different depending on the country you live in. Same with cleaning services. The basic idea of offering someone a place to stay in exchange for a fee is the same.

    • I have a landlord concerned with a privacy issue regarding a camera on the door, what should I do?

    Since the unit already has cameras pointed at the hall in the building, there shouldn’t be any issues. The important legal idea is where there is an expectation of privacy you can’t place a camera, but that doesn’t apply in this case. You would just be adding what is essentially another security camera to a hall that already has them.

    From a privacy standpoint, having a doorbell camera pointed at another unit’s door can be a problem since the camera could potentially see into the other unit when the door is open. This could lead to complaints from the other tenant which is why J tries to avoid those kinds of units. If you can control both sides of the hallway, that removes the issue so that’s a good strategy if you can swing it.

    • How long does it take to get started in short term rentals?

    This is a hard question to answer because of all the variables involved. Some markets are more difficult than others, but in general for most people it won’t take too long to get started. Cashflow Diary students get a big advantage because they get the knowledge to select the best properties for their business, so they can earn the most money and continue growing.

    Having had the privilege of teaching a variety of real estate strategies, short term rentals is the one that has allowed people to learn the most the fastest and get their business up in running very quickly.

    It is possible to go from lease signing to operation in 72 hours if you have the systems in place.

    • Can you talk about your process for finding and training cleaners?

    Finding the right cleaners is a big piece of the puzzle. Ideally you don’t go looking for cleaners, you make them find you. One way to find a cleaner is to make a reservation at a short term rental you don’t own, and when the check out happens just wait until the cleaner shows up. Another method is to join your local BNI, because that organization is referral based and a cleaner is likely to already be vetted by the person referring them. Chances are you will have to work with a few different cleaning companies before you find one you can rely on.

    • How do you recommend I leverage the leads I’m getting from a real estate broker with other local businesses?

    It’s a great idea to try to leverage your existing leads with other local businesses, but it really depends on the size of your business. The simplest way is to just go into the store and tell them who you are and what you do.

    If you can show them that you can help lower their customer acquisition cost, you’re set.

    • When is a good time to start a new unit?

    It’s always a good time to start a new unit. When you start a unit into the low season you are building up a profile so that in the high season you will have enough reviews to maximize your profits in the high season. The flip side is that starting the unit in the high season your transition to the low season won’t be as low.

    It’s more important to start a unit around the 22nd to the 25th of the month than the time of year. Keep in mind that certain holidays can actually make certain items harder to find when starting a new unit as well.

    • What is the best way to sync our calendar so we don’t have to manually block them out on different websites?

    The systems you have to have on board changes as you grow. The reason you’re having trouble with Home Away is that you’re going from one unit to five. Ultimately you want to have Lodgify working to avoid manual bookings, but the big issue here is trying to get so many units going so quickly while also building the systems you need at the same time.

    • What are your thoughts about a unit I have in the mountains where there are definite slow seasons?

    Don’t listen to someone who doesn’t have any experience with short term rentals tell you what’s going to work with short term rentals. You may not have to worry about the 30 day rental restriction in that area of Colorado. J recommends for the caller to narrow down her customers to three target markets, not just the obvious ones like ski enthusiasts.

    There is a good chance she will be able to recoup her down season by expanding her target market and appealing to a broader swath of people.

    Side note: It doesn’t matter how much you put on paper or how prepared you think you are, you aren’t. You have to get comfortable being uncomfortable and roll with the learning process. You will eventually develop a different response to the fear of action that will allow you to build the business you are dreaming of.

    • How soon should you start your own corporation? What about credit cards?

    As a general rule of thumb, it’s a good idea to have your first unit in the name of some entity. Whatever that is, consult with your attorney.

    If you have a credit card where you earn points, take advantage of it. Depending on the retailer it may make more sense to act as a consumer rather than a business.

    • I used to get a number of bookings from Booking.com but now I’m not getting any, is the drop in bookings unique to my area?

    Before you blame a platform you need to compare your performance year over year. Remember the formula: Leads x Customers x Margin x Frequency = Growth Potential. You need to know that info in order to diagnose your issue.

    • How often do you use air purifiers in your units?

    We use them as frequently as our cleaning crew suggests it needs to be done.

    • What is the best way to market and position this home?

    Answer the question of who you want to serve first. Once you answer that, the rest becomes clear. Before choosing a path, do your due diligence and understand your customer.

    • I have a studio on my primary residence that I’m thinking about turning into a short term rental, should I?

    Being in Hawaii, someone is always going to want someplace to stay but when the unit is on your primary residence it is a completely different system. J always wants to avoid the situation where the tenant knows that he’s the landlord, and that’s pretty much impossible if the unit is...


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