The Blueprint to Building Your Short-Term Rental Portfolio with Cashflow Diary Founder J. Massey

Dated: January 26 2023

Views: 63

We're thrilled to welcome J. Massey - real estate entrepreneur, father, coach, instructor, author, podcast host, short-term rental expert, and founder of Cashflow Diary, an STR hospitality training company that shows investors how to build their own short-term rental businesses.

J. has built a real estate portfolio with short term rentals at the center, and now operates a 37-unit short-term rental business, which has created more profit faster than any other strategy he has seen before.

In fact - J. and his team have identified 65 different use cases for short-term rentals.

65? Really?

If you thought that short-term rentals were just beach condos and cabins in the woods, you will want to hear what J. has to say! 

Cashflow Diary exists to create short-term rental entrepreneurs. With Cashflow Diary, J. has trained thousands of students, helping them invest profits into whatever is most important to them - family, business, community, and the future.

In this episode, we discussed:
- Balancing the tax challenges of active income with buy-and-hold strategies
- How J. discovered short-term rentals as the perfect entry point for many
- Why your labor should build assets rather than simply building income
- What's the difference between being in your career and being retired?
- Why short-term rentals solve single points of failure for investors
- Benefits to short-term rental arbitrage, both from the standpoints of operators and property owners
- The 65 different use cases for short-term rentals
- J.'s thoughts on oversupply in the short-term rental market
- What opportunities are a little less apparent in the short-term rental space?
- Themed short-term rentals and why they work well
- Scaling your business and the need for learning leadership 

Where you can find J. Massey:
Website -
Facebook -
Instagram -
LinkedIn -
YouTube -
The Ultimate Short Term Rental Guide -
How To Start An Airbnb Business:

Text "Blueprint" to 949-881-6939 for J.'s free eight-hour course to learn how to get your first short-term rental

Join Jason Muth and Attorney / Broker Rory Gill of NextHome Titletown and UrbanVillage Legal in Boston, Massachusetts for another episode of The Real Estate Law Podcast!

#realestatepodcast #nexthome #humansoverhouses #realestate #realestatelaw #realestateinvesting #realestateinvestor #realestateagent #airbnb #str #shorttermrentals #vacationrentals #airbnbtips #airbnbinvestor #mediumtermrental #airbnbarbitrage #cashflow

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Rory Gill

Rory, our Broker/Owner, brings a wide range of real estate experience and expertise.  A licensed attorney, Rory has worked creatively with investors and homebuyers to find opportunities and solve pro....

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