The Blueprint to Building Your Short-Term Rental Portfolio with Cashflow Diary Founder J. Massey
Dated: January 26 2023
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.
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
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....
Should you require assistance in navigating our website or searching for real estate,
please contact our offices at
Each office is independently owned and operated.
Massachusetts MLS Property Info Network (MLSPIN) - The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and
may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein. Last Update: September 19, 2023 5:02 PM UTC
Copyright 2023 PrimeMLS. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on
this Site comes in part from the IDX Program of PrimeMLS. The information
being provided is for consumers' personal, non-commercial use and may
not be used for any purpose other than to identify prospective properties
consumers may be interested in purchasing. Data last updated September 21, 2023 4:43 PM UTC
By registering, you agree to our Terms & Conditions
and that real estate professionals from NextHome Titletown and lenders may call/text you about your inquiry,
which may involve use of automated means and prerecorded/artificial voices. Message frequency varies.
Text HELP for help or STOP to cancel. You don't need to consent as a condition of buying any property,
goods or services. Messages/data rates may apply. Additional information about data use is in our