About Cashflow Diary

a short-term rental hospitality training company

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…

Cashflow Diary is here to share all of it with you.

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 – the answer at the time was, “not very much.” He started looking into the model and was astounded at the opportunities it presented.J. now runs a 27 unit short-term rental business, and they create more profit faster than any other strategy he has seen before.

That means that you too will now have a business that creates more profits to invest into whatever is most important to you—your family, your business, your future, and your community.

The bottom line is that because short-term rental businesses provides a financial safety net, you can take more risks, develop advanced business skills, and do more of what you’re passionate about.

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.

Cashflow Diary Staff

J. Massey, CEO

Dave Sentenn, CMO

Robert Voccola, Instructor

Della Bercovitch, Customer Service Manager

Megan Wilson, Executive Assistant

Julie Hoflin, Video Editor

“Once you’ve made it, it’s your responsibility to help others make it, too.”

- J. Massey

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