Why on earth do we all have to work 9-5? Ok, not all, but that is still typical office hours. Nearly all offices run at some time between 8 and 6 PM, meaning everybody is on the road at the same time, to take a doctor’s appointment means time off work (costing the economy) and its tricky for some to pick up the kids from school. Mr. Massey shares his 9-5 story!

Please introduce yourself to our reading audience.

My name is J. Massey, and I am a real estate investor, entrepreneur, husband, and father. After years of investing in everything from single-family homes, to land, to apartment buildings, to cell phone towers, I began to focus on the most lucrative form of real estate investing I could find: short-term rentals.

Today I own and operate 34 of my own units and have built a multimillion-dollar company teaching others how to do the same. I’ve spoken on some pretty big stages, written a best-selling book, and walked hundreds of people through the process of building their real estate portfolio through short-term rentals.

I am passionate about teaching and encouraging entrepreneurs who want more time, freedom, and wealth so that they can be there for their families and make an impact on their communities.

Today, I do that through my year-long business incubator, which walks people through the process of starting and scaling their short-term rental business.

What made you want to go into business?

The constraints of a 9-5 didn’t work for me.

Having to ask if I could go pick up my daughter from school if she was sick didn’t work for me, especially when I was a single father. I was tired of fighting traffic and answering to someone else, and I wanted to do things on my own terms.

The world is always telling you what you can’t do and what you “should” do. We have a choice to believe or not believe what the world says.

I chose not to believe it, left the 9-5 world, and have run multiple iterations of my business over the years since.

Why are you so passionate about empowering women?

I am the father of three daughters, and I want them to know that they can provide for themselves and that a man is not a financial plan.

It’s important to me that they understand that they can secure their financial future on their own and that they have choices in how they do that.

I am passionate about empowering women today because I want my daughters to not only see me and their mom make things happen but also see other women that look like them and have the same concerns as they do make things happen.

I also believe there are many things that women are better at when it comes to business. So many of my students who are women and moms don’t see themselves as having business skills, but the truth is, mom skills transfer well into the business world.

I like to tell my students, “If you’ve ever been able to get your kid to bed on time… then you have sales skills.”

And yes, they’re kids… but adults are just big kids.

Because of that, it’s important to me that successful, smart, driven, hard-working women are elevated and empowered to share what they do with the world.

What’s something most of the subscribers don’t know about you – something fun, witty, out of the box?

I have pretty much made it my business to tell people my business, so there isn’t a ton, but one thing that comes to mind is that I used to live in Alaska, and when I was there I lost my two front teeth… not as a toddler. I lost my two front, permanent teeth.

It was my first time playing frisbee and I ended up catching the frisbee with my mouth instead of my hands. My teeth paid the price.

List 5 real estate tips that will allow you to retire from your job?

I was capable of retiring at 38 because of my real estate investing. Today, I do what I do because I want to, not because I have to. So I will share the 5 things that helped me do that and will help others do the same

  1. Understanding the value of cash flow which is the only form of truly passive income. It is more valuable than active income.
  2. Understanding what inflation is and understanding how to play with it both offensively and defensively.
  3. Understand this one thing about the tax code: it’s a really big encyclopedia of how you don’t have to pay taxes.

Most tax codes basically say if you’re willing to provide jobs, housing, energy or food… then you qualify for tax breaks. If you don’t provide those things, then we don’t give you the tax breaks.

Once you know that as a general statement, the question becomes which of those (or which combo) do you want to provide, and then learning to do that. With real estate, you are providing both housing and jobs.

  1. I don’t actually like real estate. In fact, most investors don’t like real estate — we like the benefits. A lot of people think that they have to actually like real estate to be successful at investing. Not true. It’s simply about drawing a benefit from your assets.
  2. The #1 thing to do with your time is to gain skills you can use to help you build, own, and control assets… and then sell the use of those assets.

What is your favorite quote?

Well, I personally say, “now o’clock” and “move at the speed of instruction” often, because those have been major themes for me and my students over the years.

There’s so many, so there’s not really just one quote. However, there is a poem by Marianne Williamson.

“Our deepest fear is not that we are inadequate. Our deepest fear is that we are powerful beyond measure. It is our light, not our darkness that most frightens us. We ask ourselves,

‘Who am I to be brilliant, gorgeous, talented, fabulous?’ Actually, who are you not to be?

You are a child of God. You’re playing small does not serve the world. There is nothing enlightened about shrinking so that other people won’t feel insecure around you. We are all meant to shine, as children do. We were born to make manifest the glory of God that is within us. It’s not just in some of us; it’s in everyone. And as we let our own light shine, we unconsciously give other people permission to do the same. As we are liberated from our own fear, our presence automatically liberates others.”

How can people connect with you?

Connect with me by click here.

What is next for you in 2020?

Right now, we are looking for the next 5 people to be our 7-figure earners. We have developed a few already, and we’re ready to develop more.

We’ve created a yearlong program that will allow people to work more directly with me, my team, and our guest experts so that we can develop more 7-figure business owners who leverage the power of short-term rentals.

What fires me up about this is that the level of real estate experience is irrelevant. The level of cash or capital is irrelevant.

This new program works for anyone who wants a path into the real estate game, which previously felt very exclusionary. Our goal this year is to make it far more accessible to far more people, at an even higher level of service than our already exceptional level of service.


Contributing Writer – Dr. Cozette M. White, Advisory Accountant and Tax Expert.  Learn more about Dr. Cozette M. White at

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Featured Image courtesy of J. Massey