Start Your Success Journey Today!
With over 100 completed real estate transactions and 4,000+ real estate entrepreneur students, J. Massey is the go-to expert for launching and scaling your STR business.

If you’re ready to get serious about your STR business,
apply to book a 1:1 call with J today.

Learn and master the skills to build your short-term rental business by choosing to work with us.

Build A Legacy

By investing in and scaling a  business that will create  generational wealth for you
and your family.

Create Your Dream Life

Allow your passive income to become your main source of revenue and quit your 9-5.

Find Financial Freedom

By automating your business through the implementation of solid, standard operating  procedures.

Generate Cashflow

Secure your next real estate
investment property in half the time, and make it twice as  profitable.

Here’s How We Can Help You

Angela Simon built out a portfolio of over 15 units in only 6 months! It wasn’t long before Angela was able to quit her full-time job. But the coolest thing about it…
She considers it: “The best decision I have ever made!”
Because none of this happens by accident.

And if she can do it – so can YOU.

J. Massey has been the leading authority on how to build significant cashflow using short term rentals, for years. NOW is the time to start leaning into the short term rental world, so you can build your cashflow WHILE building long-term, generational wealth…securing freedom for you today, and your family and future generations, tomorrow!

If you're looking to catapult your short term rental to the next level, but aren't sure how - get in touch. Book a call now.

Angela Simon

What our members have to say 

Sara Kingston
North Dakota, USA

I've been in the STR business for about 2.5 years. After coming across J, I realized what I really wanted in life and that I wanted to by my own boss.

I could tell just by listening to J talk on a podcast that he is not the type of person to just take my money and leave me to figure things out on my own. He is just as committed to all of his students  - seeing them grow, watching them become successful and realizing their dreams.


J and the Cashflow Diary network are amazing. These people represent a true mastermind of high-level entrepreneurs and short term rental rock stars. They're always willing to support you. And, the bottom line is everyone is winning and wants you to win too!


J. Massey

is a full-time Real Estate Investor, Entrepreneur, Popular Podcast Host, Author, Speaker, Coach & All-Around Problem Solver Cashflow Diary is a short-term rental hospitality training company. We show people how to build their own short-term rental business (without needing to buy or own any property) so they can thrive financially.

Heralded as the most advanced short-term rental training in the industry, Cashflow Diary enjoys creating content and communities that are solely focused on developing individuals into powerful business owners. Founded by J. Massey, Cashflow Diary exists to create short-term rental entrepreneurs. No matter your passion, he believes that running a hospitality business will change people’s lives…