loader from loading.io

Scaling A Short Term Rental Business Q&A

Cashflow Diary™

Release Date: 12/30/2019

How to Launch Your Side Hustle with Troy Underwood show art How to Launch Your Side Hustle with Troy Underwood

Cashflow Diary™

Troy R. Underwood is an industry disruptor. Part technologist, part economist, and all innovator, he revolutionized the motor vehicle industry with the nation’s first electronic title system for financial institutions, which was later sold for $106 million. His healthcare venture, benefitsCONNECT, innovated healthcare benefits administration and resulted in a highly successful acquisition. His new book is How to Launch Your Side Hustle: Start and Scale a Business with Minimal Capital. Learn more at .  Podcast Highlights Who is Troy Underwood?  Troy considers himself a necessity...

Be Your Own Banker and Grow More Wealth with Mark Willis show art Be Your Own Banker and Grow More Wealth with Mark Willis

Cashflow Diary™

Mark Willis, is a CERTIFIED FINANCIAL PLANNER™, a #1 Best Selling Author and the owner of Lake Growth Financial Services, a financial firm in Chicago, Illinois.  Over the years, he has helped hundreds of his clients take back control of their financial future and build their businesses with sophisticated, tax-efficient financial solutions.  Mark Willis specializes in building custom-tailored financial strategies that are unknown to typical stock-jockeys, attorneys, or other financial gurus.  As co-host of the Not Your Average Financial Podcast, he shares some of his strategies...

Contact Marketing Secrets: How to Get a Meeting With Anyone show art Contact Marketing Secrets: How to Get a Meeting With Anyone

Cashflow Diary™

Stu Heinecke is the Hall of Fame “Father of Contact Marketing" and Founder/President of the Contact Marketing Agency and Cartoonlink, which helps sales teams break through using contact marketing solutions to produce critical contact with accounts and prospects. He is a longstanding senior cartoonist for the Wall Street Journal and the bestselling author of How to Get a Meeting with Anyone: The Untapped Selling Power of Contact Marketing and the new book Get the Meeting!: An Illustrative Contact Marketing Playbook.  He hosts Contact Marketing Radio and the How to Get a Meeting With...

Creating Passive Income with Chris Miles show art Creating Passive Income with Chris Miles

Cashflow Diary™

As founder of Money Ripples, host of The Chris Miles Money Show, and co-author of the book Entrepreneur on Fire, Chris Miles is a leading authority on quickly creating wealth by increasing monthly cash flow and creating passive income. He has shown hundreds of thousands internationally how to free up or generate tens of thousands of dollars each year! Chris has been featured in US News, CNNMoney, and Bankrate.com and has a reputation for getting his clients fast, proven results.  Many of his clients have the option to retire in less than 5-10 years, and Chris himself was able to retire...

Conquering Corona With Kyle Stanley show art Conquering Corona With Kyle Stanley

Cashflow Diary™

Kyle Stanley is the host of the Fearless Flipping podcast where he educates new hungry real estate investors about best practices for getting started. We flip the roles into today’s episode with J being interviewed for Kyle’s podcast. Find out how J is conquering the coronavirus and adjusting his short term rental business to be even more successful than before.  Podcast Highlights How did you get to this point and what brought you into the short term rental business?  The keyword for J is cash flow, everything he’s done in terms of business is around generating an income...

Protecting Your Assets In A Changing Marketplace show art Protecting Your Assets In A Changing Marketplace

Cashflow Diary™

Let me introduce you to Scott Smith, a new breed of real estate attorney with a great sense of humor and a gift for simplifying the complex. His Austin startup, Royal Legal Solutions, has a different take on protecting your assets including real estate investments and already serves thousands of clients across all 50 states. As a former litigation attorney, Scott has a deep understanding of how lawsuits really work. More importantly, he is a real estate investor himself, with property in 10 states. Now he’s sharing his information with the world and is committed to helping other real estate...

Public Speaking Tips and Strategies with Jacqueline Nagle show art Public Speaking Tips and Strategies with Jacqueline Nagle

Cashflow Diary™

With a diverse career crossing professional services, mining services, civil construction, manufacturing, industrial relations Jacqueline has used  public speaking-centric strategies extensively to launch, pivot and manage both growth and crisis across all of those organizations.

What To Do When The AirBnB Business Changes show art What To Do When The AirBnB Business Changes

Cashflow Diary™

Kyle Stanley is the host of the Fearless Flipping podcast where he educates new hungry real estate investors about best practices for getting started. Kyle is also a master with AirBnB and believes it's the best form of almost-completely-passive income in today's economy.  Podcast Highlights   Who is Kyle Stanley?    Kyle doesn’t like the term “serial entrepreneur”, he prefers the idea of FOCUS (focus on one course until success). Kyle had to make a lot of adjustments over his career based on his skills and what he enjoyed. Kyle started out as a sports anchor in...

This Is Your Defining Moment with Chad Peterson show art This Is Your Defining Moment with Chad Peterson

Cashflow Diary™

Chad Peterson is an expert business broker and the founder of Peterson Acquisitions, an award-winning M&A firm. Chad’s firm handles transactions in the $1 million to $25 million range, with some deals exceeding $25 million.  He works with companies all over the United States and has completed international deals as well. Peterson Acquisitions was recently named by one publication as the #1 ranked business broker in the United States. What sets Chad Peterson apart from all other business brokers is his aggressive style, work ethic and tenacity that are rooted in his humble...

GoodEgg Investments Founders Talk Real Estate Syndications show art GoodEgg Investments Founders Talk Real Estate Syndications

Cashflow Diary™

Annie Dickerson and Julie Lam are the co-founders and managing partners of Goodegg Investments, a premier real estate investing company that helps people learn about and invest in    They are both moms (Annie has 2 kids and Julie has 3) and are passionate about helping other families build passive income so they can spend more time with the people they love, doing the things they love, and living a life by design.  Podcast Highlights   Who is Annie Dickerson and Julie Lam?    Annie started as an elementary school teacher and after setting out to buy her first...

More Episodes

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.


Think and Grow Rich



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