A full-time real estate investor, entrepreneur, popular podcast host, author, speaker, coach and all-around problem solver, J. Massey is well known for providing best-in-class advice and strategies to help new and experienced investors the world over.

J.’s platform is simple… He invests his time looking for investment opportunities (a.k.a., problems to solve through real estate transactions), closing deals and teaching others how to find and manage similar opportunities, including getting Deals At Discounts and Raising Private Capital to Investing in Multi-Family Properties, getting leads and negotiating the deal.

By turning his real-world field work into killer training courses, new and seasoned investors alike learn win-win solutions to solve real estate “problems” for buyers, sellers and other investors. J.’s cashflow-creation strategies are embraced on a global scale by people who want to learn better ways to achieve tangible success in real estate investing, and in his words become “bigger, badder, better real estate investors.” His growing network of “Cashflow Creators” is proof that J. practices what he teaches and teaches what he practices.

Prior to real estate investing, J. held positions in insurance and financial planning as a licensed representative with the National Association of Securities Dealers (NASD), the Securities and Exchange Commission (SEC), the California Dept of Insurance (CDI), and a Registered Investment Advisor Representative (RIAR).

J. is currently a landlord, lender, consultant, educator and highly sought mentor. He currently owns hundreds of units of properties and has completed hundreds more real estate transactions across several states.

He is a member of the National Sales Network, Renatus and Toastmaster’s International (CC). J. holds more than 12 awards for public speaking including 2nd Place in the 2008 Founders District International Speech Contest, 1st place in the 2009 Founders District Table Topics, and 2nd place in the 2010 Founders District International Speech and Table Topics contests.

J.’s publishing credits include a book he co-authored titled “3 Money Raising Questions.” In 2014 he released his highly acclaimed book, Cashflow Diary: 10 Steps to Creating Wealth in ANY Economy!

He has also authored a number of educational e-books on a variety of topics in real estate investing and networking to create wealth. These are available on this site to members in good standing.

Meet The Team

J. Massey

CEO, Real Estate Investor and Developer

Since you’re here on the site, chances are you’ve been browsing and already learned that J. Massey is a master of creating cash flow and passive income through smart real estate and business transactions. J.’s talents don’t stop there. He’s also a successful business owner, energetic author, popular podcast host, insightful instructor, cash flow creation coach and more.

Andrée Caldwell

Executive Administrator

This seasoned administrative professional came to us with 17 years of experience in office administration and a strong background in business operations, corporate event planning, residential real estate and commercial lending (securities). As an entrepreneur, she offered business development consulting services to small businesses and startup companies. Andrée is a valued member of our team who is tasked to keep several balls in the air at once while maintaining J.’s schedule at the same time. That’s impressive!

Jake Bongiovanni

CTO and Marketing Director

Before coming on board Team Massey, Jake earned his stripes as a professional photographer and videographer, shooting a lot of beautiful faces and places over the past decade. Now he is in charge of shooting J. Massey in the studio and on the go for videos of all sorts, including visual training materials and online presentations. Jake’s talents can be seen everywhere J. can be seen online, and we are grateful to have him on the team, chronicling our growth and adventures in real estate investing!

David Sentenn


David Sentenn joined Cashflow Diary in February of 2017. Prior to joining the team, he served as a CMO and CMO Advisor for businesses and startups in technology and healthcare. Having worked and consulted for companies like E! Entertainment and Mattel, David left the corporate space to build his own marketing agency, which he exited by sale in 2015.

Chad Curtiss

Assistant Videographer and Web Development Professional

Where would we be without the extra helpful hands attached to this dedicated individual’s capable arms (and brain)? What can we say about Chad, other than that he is awesome and an integral part of getting things done quickly around here. A lot of the sales pages you see on this site and on special landing pages that populate the Internet are Chad’s creations. He has an eye for style, color and placement of all the elements that make a page stand out. Plus, he’s the man behind the man when it comes to our podcast! Without him, the podcast wouldn’t sound nearly as good as it does. Chad is an excellent technical whiz on that front. (Plus, he happens to be a wonderful actor. Look him up in IMDB!)

Drew Heskett

Creative Director

With an extensive background in directing documentary films and commercials, Drew is passionate about telling true stories that inspire people towards a positive change. Here at CashFlow Diary, Drew oversees the creative direction behind nearly every video we create, making sure that all of our content is as clean and crisp as can be, and that J’s message is able to resonate online as powerfully as it does when you’re with him in-person.

Della Bercovitch

Head of Customer Care

Della has been a member of the Cashflow Diary team since 2015. In her role as Customer Service, she acts as a liaison between Cashflow Diary’s customers and the rest of the Cashflow Diary team. She strives to build trust and strong long term relationships with Cashflow Diary’s customers and exceed the customer’s expectations.