Humans don’t transform overnight. Most people can’t just read a book or watch a video and completely change their life immediately. You’re not going to be able to pick up a bunch of short term rental units right away. That’s the reason that J developed the Cashflow Diary Roadmap, the Roadmap is a program that combines an immense library of content and training and accountability coaching to make sure you achieve your short term rental goals.

Questions and Answers

  • Moving at the Speed of Instruction 

When you’re moving at the speed of instruction, you don’t have the time to question your capacity to do something. With a little bit of trust and follow through, you can accomplish more than you would believe is currently possible.

Humans tend not to value as much as they should. If you want to achieve anything worthwhile, you need to be willing to fail. Fail frequently, and fail forward. 

One of the things about schooling that prevents you from getting ahead is the belief that you must learn everything in the program or book before you are qualified to act. It’s much more effective to read a chapter, then put the book down and put what you learned into action. You will get much more out of what you learn by combining it with actual experience.

  • How do we secure POE cameras to prevent them from unplugging?  

The cameras that J recommends are hard wired directly into the electricity of the house so they can’t be unplugged. In the case of the caller, the installer didn’t run the wire through the walls so the simple solution is to bring them back in and redo the installation.

  • I currently have a couple short term rental units and trying to figure out where to be next, where should I be looking?

New Jersey is a good place to look since it’s one of the most short term rental friendly states in the country. 

  • I’ve been talking to a couple of landlords but have been having trouble conveying what we do, how do we approach this conversation?

If a landlord has concerns about the number of people that are going to be staying in their unit, the key is to assure them that you screen guests just as thoroughly as they do and care just as much what kind of guests stay in the unit. Talk about the fact that you are always available because of your systems that you have in place and that it’s more common for you as a short term rental operator to have issues with long term tenants than they will have with your guests.

Avoid telling the landlord the range of the number of people who could potentially stay at the unit, it’s better to describe a specific use situation so they can easily imagine the kind of guest you are describing.

They don’t know that you have the capacity to screen people just as well as they do, so you have to be able to communicate that in a way that makes them feel more secure about doing business with you. If something does happen, you can also tell them the systems you have in place allow you to remove a guest from the property and involve the authorities if necessary much faster than they could due to the restrictions around their business model.

Being detached from the outcome is also very important. If that particular landlord doesn’t take you up on your offer, that’s okay. You can move on to the next landlord who is interested in the solution you’re offering. 

  • In Ottawa, the city ordinance proposed an ordinance restricting short term rentals to residents only. Would it be easier to operate in other cities with fewer restrictions?

Operating at a distance may prevent you from growing your business as fast, but it’s definitely possible. If your local area is not conducive to the short term rental business model, it’s totally possible to build it out in a separate city.

  • Where does one learn these conversation techniques?

All these techniques were originally taught during a live event but now they are all available within the Roadmap program.

Putting a little bit of effort into the research before speaking to a landlord will put you miles ahead of the average short term rental operator and make the conversation you have much smoother.

  • The Cashflow Diary Roadmap

J and the Cashflow Diary are dedicated to providing hands on and direct training to students that want to create their own six and seven figure short term rental businesses. 

Roadmap members get access to hundreds of hours of content covering every aspect of building a short term rental business including cash flow, negotiations, operations, lead generation, seller financing, and more. Everything you need to develop the skills you must have to become the bravest entrepreneur you can be.


The Slight Edge by Jeff Olson

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

Grab a copy of our short term rental playbook.

Claim your copy now

Join the most advanced active group of short term rental professionals.  Free trainings weekly.

Join The Community

Apply now for a free consultation.

Apply Now