Your Roadmap to Freedom Awaits

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100+ Hours

On-Demand Video Instruction

5x Per Week

Meetings with J. Massey & Team

Coaching

Get Your Own Personal Accountability Coach

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An incredible learning experience

World-class training in Short Term Rentals, Real Estate, and Entrepreneurship

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Experience explosive personal and professional growth

In this 12-month program on mastering the short term rental industry, you’ll learn

The foundational elements of how to find, secure, and manage your first set of short term rental units.

How to negotiate with landlords and get the agreement you're looking for.

Where to find new leads so you always have plenty to work from.

How to talk with investors and partners to always find win-win propositions and the capital you're looking for

The tools and resources that work best for running your STR business. You'll be focused on growing and scaling your business instead of getting stuck working in the business.

We're Ready To Help and Teach You Through Every Step

In this 12 month coaching intensive you're also going to get:

The full STR Mastermind Business System - a blueprint for starting and growing your short term rental busines

Access to hundreds of hours or training videos, Q&A sessions, masterminding, and live, interactive coaching calls

A personal accountability coach who will help you formulate your goals, makes plans, and track your progress

A total commitment to helping you every step of the way, through every phase of your development

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37+ Courses

Cashflow Diary has authored more than 37 real estate, business, and personal growth courses, trainings, and modules. You get access to it all. Here's a sample.

01

STR Mastermind Business System

Learn how to find, fund, build, run and scale your short term rental business, team, and brand.


02

Cashflow Foundation

Gain an understanding of exactly what you need to do to grow your business (as in, step by step guidance) in determining how to exchange cash with ease for your product or service.


03

Capital Creators

Learn how to get other people behind your vision so you can raise private capital with ease and take control of your financial future.


04

Ninja Negotiation Secrets

Get all the secrets to talking to investors and landlords so you can get what you want out of nearly every deal. Learn how to create wins for all parties.


05

Income Infusion

Learn the complete sales system and process J uses to increase sales, generate more revenue, and get more referrals for his businesses


06

Basic Business Disciplines

There’s a lot to do and remember as an entrepreneur. We break down some of the most important tasks and mindset shifts you need as a business owner.


07

Investors Roundtable

Learn J’s own approach and system to building and growing his business, complete with exercises and action steps so you can start implementing right away.

The Roadmap to Retirement

Your Roadmap to Retirement, entrepreneurship, and financial intelligence begins now!

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Endless education

More than 100 hours of training to help you start and grow your business right from the start.

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Goals Achieved

You’ve been wanting to grow that business. We make sure you reach the goals you set.

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Business Know-How

You don’t need a degree in business to be successful. You need support from others who have been there.

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Any Time, Anywhere

The Cashflow DIary mobile app allows you to access the courses, network, and live trainings from anywhere.

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Mentorship

Every student gets a personal accountability coach. We’ll help you set goals and plans, and support you every step of your specific journey.

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Community

Network with other Cashflow Diary Students. Learn from those that have been there, done that. Brainstorm and collaborate with seasoned operators

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Mindset

Entrepreneurship, financial education, and ownership requires mindset shifts. They happen subtly and incrementally. But we make sure they happen.

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Cashflow Library

Access a treasure trove of every course, book, and module on business building, financial education, and system we've ever built.

It's NowO'Clock.

Your success is predicated on your action. We've got the structure and support.

100+ Hours of on-demand video courses

Tons of downloadable resources

Access on mobile

Over 1000+ Mastermind students

Guest Speakers

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STR Student Reviews

Meet real students experiencing real results. They followed the recipe and are reaping the rewards

J and the Cashflow Diary network are amazing. These group of people represents a true mastermind of high-level entrepreneurs and short term rental rockstars that are always willing to support you. The bottom line is everyone is winning and wants you to win too!

Chinedu Akunne
Pharmacists and STR Entrepreneur

It's exciting to see how quickly you can grow this business & all the different streams of income that can be attached to it.

Shirley W
Cashflow Diary Student

If you can follow a system and stop trying to deviate - to be able to profit $700, $1000, $1500+ a month per unit is crazy... Just saying... All I'm missing is raising this capital to pop these things up like hot cakes.

Larry Simmons
STR Entrepreneur

The people that have come into my life from this group has made this worth it. The kindness, encouragement, friendship, motivation, incite, wisdom I have gained here has helped me in so many ways far beyond the business. But mainly this Opportunity, has given me back my dreams. I now see a future (not too far off) where I can tell my boss I am "retiring" from the corporate world.

Carol Smith
Tech Consultant & STR Entrepreneur

Thank you J and Cashflow Diary for helping me discover my potential in the STR Roadmap to Retirement Program. I would like to let everyone know; The only thing that is stopping you from achieving your dreams is YOU. Join this group to see what you can really achieve.”

Nevin Joseph
STR Entrepreneur
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About Cashflow Diary

J Massey is a full-time Real Estate Investor, Entrepreneur, Popular Podcast Host, Author, Speaker, and Coach

Cashflow Diary is a real estate education and training company. We show people how to build streams cashflow while focusing on real estate -- especially short-term rental businesses -- so they can thrive financially now and into the future.

Heralded as the most advanced and comprehensive short-term rental training program 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 entrepreneurs. No matter your passion, he believes that running a business will change your life, and the way you live in retirement.

You have questions. We have answers.

How do I access the educational marterials?

Once you sign up, you’ll receive an email with all your access instructions and access to our custom mobile app. Courses are available on the private Cashflow Diary mobile app hosted by MightyNetworks, an online community and educational portal, and on the app. Sign-in and navigation is a cinch!

When can I get started?

The way we have the materials structured, you have full access the moment you commit with your payment! You’ll have access to our Facebook community, the coursework and your support system right away.

When are the live calls?

Calls are currently hosted Monday, Tuesday, and Wednesday at 10 am PST. Special guests hosts may also host on a fourth day of the week.

How long is my commitment?

This is a 12-month commitment to being coached and mentored by J. and his team of short term rental operators and mentors.

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