About Cashflow Diary

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.

Cashflow Diary exists to create short-term rental entrepreneurs. No matter your passion, J. believes that running a hospitality business with his blueprint plan will change people’s lives.

Some of our members have already been able to quit their full-time jobs, become their own boss, travel the world, and more. This could be YOU. It's easier than you think. Especially with the help of checklists, worksheets, samples, and even templates – ALL included inside the FREE STR Blueprint.

About - Cashflow Diary

About J. Massey


J. Massey is not an extraordinary human being; he did not have a formal education beyond high school; he entered the real estate market at one of the worst times in history for that industry; his wife was critically ill and he was injured so he could not work. What makes J. Massey different and very successful as a businessman and real estate investor is that he took action and then kept taking action steps - learning and earning, learning and earning - to get him where he is today.

Prior to entering the sharing economy, J. taught real estate strategies based on his years of experience. He owned hundreds of units, raised tens of millions of dollars, and even owned cell phone towers.

He was all but “retired” at the age of 38, when one of his students asked what he knew about short-term rentals.  While the answer at the time was, “not very much”, J. started looking into the model and was astounded at the opportunities it presented.

Since that fateful day, J. Massey became a full-time real estate investor, founded Cashflow Diary,  and now runs a 34 unit short-term rental business, which have create more profit faster than any other strategy he has seen before. J. has also reached tens of thousands of listeners as the host of The Cashflow Diary Podcast, delighted readers as the author of The Cashflow Diary book,
commanded rooms as highly sought after Speaker, and changed countless lives as a wildly successful business coach for entrepreneurs.  

The Cashflow Diary Mission

J. believes that you too can have a business that creates more profits to invest into whatever is most important to you.  
Whether that impotence rest with your family, your business, your future, or your community, J. can help you create financial safety net.
From there you can take more risks, develop advanced business skills, and do more with the projects in life about which you are most passionate.

Cashflow Diary will show you everything you need to know about running your our own business, and we’ve built a team of fellow short-term rental entrepreneurs from around the world, each with their own expertise – all to give you the blueprint to succeed in this exciting new economy.

Want to begin your journey with a short-term rental business?

The Cashflow Diary Podcast

Launched in July of 2012, J’s podcast immediately drew an astounding amount of downloads, quickly jumped to the top of the charts in Apple Podcasts Business category and topped over 2 million downloads in 100 countries.

Break through the clutter of learning real estate and business investing and become a successful entrepreneur. Listen to beneficial strategies to improve your skills in prospecting, placing offers, closing deals, buying, selling, wholesaling, fix & Flips, rehabs and much more. By way of Cashflow™ Diary, J. Massey freely  gives away current industry strategies by simply teaching what he does daily as a real estate practitioner.


J. Massey wasn't always a highly skilled investor,  but through action steps that he shares in this book, he amassed an impressive portfolio of hundreds of  properties in just six years using an intensive approach  to learning and then putting to use what he learned  immediately and at the Speed of Instruction™.

Starting from less than zero, he used other people's cash and credit to invest in properties, from single-family homes to multi-family dwellings and large apartment complexes to commercial properties. He now owns businesses and teaches others to do exactly what he does today with nothing held back. This insider's look into the world of real estate investing and building a successful business gives readers the absolute road map to their own success as  entrepreneurs and investors.

Reviews From
Cashflow Diary Students

“J is truly an inspirational and educated man! He dives deep in the life of an entrepreneur and discusses how handling finances in the business realm is a very important asset to society! Highly recommend.”


“I have been a fan of J. Massey for almost 2 years now, since I discovered his podcast. He has been my mentor from afar…thanks to J and the CFD team.”


“Learn from the MASTER. J is someone who clearly practices what he preaches. He has REAL experience and has shown how to go from zero to huge success with passion, drive, perseverance and strong will…I love how J extracts helpful tips to apply to all business - not just real estate. I highly recommend you invest your time.”


Connect With J. Massey