From Rock Bottom to Riches

The Better Relationship Podcast Episode #008

From Rock Bottom to Riches w/ J. Massey

Show Notes

Have you ever wondered what it would take to succeed after you feel you’ve hit rock-bottom?   Do you worry about how climbing out of that situation will affect your relationships and your family?   Are you worried about failing?   If the answer to these questions is “Yes”, join J. Massey as he tells how he went from Rock Bottom to Riches!

About J. Massey’s

Wasn’t always the real estate investor he is today but he has always been a family man. In fact, the reason he went into real estate investing in the first place was for the single purpose of being able to feed his family.

His road was paved with challenges that he had to overcome.  He literally went from squatting in bank-owned properties with no ability to feed his family to owning more than 300 units of property across several states.

Today, he’s an investor, a published author, speaker and educator, a podcast host, an entrepreneur and a business owner.

His brand, Cash Flow Diary, is gaining global recognition. He remains steadfast in his devotion to his family and his spirituality.

“At the end of the day, we are the stories that we leave behind.”

Yes, he and his family have now experienced success and can also provide safe, affordable, clean housing for others but there are going to be other people that want to do the same thing.

There are other people who feel the same way he does and he wants them to know that it IS possible.


  • He began his career as a financial planner.
  • He tried the standard, corporate thing and that did NOT work for him.   It took him 27 years to figure out that he never should have been an employee in the first place.
  • Within 6 months of starting the real estate investment business, he ended up creating a 6- figure income.
  • He was the first individual in his family able to do that. It changed his mindset about EVERYTHING

His Journey

“If there’s anything I say today that I want you to get, it’s this: Your story is not over.” ~J. Massey

  • While he was employed as a financial planner, both he and his wife confronted some serious     medical issues.  In short, he and his wife were both bedridden and unable to work at the exact same time.
  • By late 2007-early 2008, they had been through selling their possessions on EBay and after those resources ran out, they started squatting in bank-owned properties. They were making decisions re electric or food.
  • A friend of his suggested to him that they should become a real estate investor. He was astounded. They didn’t even own their own house anymore!
  • But, that was one of the first times in his life that he didn’t let what he didn’t’ have stop him. He feels this is a lesson so many people should learn.

Many times we stop ourselves from exploring what could become the solution to our issue because we don’t see how or we don’t know the path. We need to be willing to explore and freefall a little bit, to take the opportunity to discover there may be something inside of you that’s dying to come out.

His Marriage and His Motivation

  • When they lost everything, by that point there had already been several serious conversations.
  • To his wife’s credit, money and success were not the reason she was with him.
  • That made him want to figure it out that much more.
  • When you take your vows ‘for better or for worse’, he felt he had so far introduced nothing but ‘the worse’. That feeling was his impetus.

We can only blame external factors so much. There’s only one real person to blame.

Your life is the result of your absolute best decisions.

  • What that means is that no one ever wakes up and says “Today, I am going to aim straight for the bottom”.
  • In other words, your best decision, even if it was bad, it seemed like the best one for you to make at the time.
  • So, he had to take inventory.  His absolute best had put his family into a situation where they were squatting and making decisions between food or electric.

The strongest thing you can do is tell your wife the truth about the situation. She has ideas you haven’t even considered. She’s got resolve and strength that you don’t even know how to rely on and by not telling her, you’re not giving her an opportunity to contribute.

The Freedom to Fail

  • His wife wasn’t necessarily ‘supportive’ at the beginning. But, she just wanted him to do “something”, to take an action.
  • She gave him the freedom to fail.
  • That is a really necessary process but we are taught from day one NOT to fail. We are taught that we need to get it right, we need to get it right the first time and we need to get it right with no help.
  • As an entrepreneur, you never get it right the first time. And, you’re never going to get it right without help.
  • Giving someone the freedom to fail is not about having to say or do something specific.

It’s that you DON’T do what instinctively happens, like “exploding” or criticizing or thinking that you might be helping by giving suggestions and unsolicited advice.

Fail As Fast As You Can

Go out and fail as fast as you can.

The reason why you haven’t seen the success in what you want, and it applies to anything, business, relationships, etc. is because you have an addiction. The addiction is to “looking good”.

You can’t learn AND look good at the same time.

  • When you’re an adult, you’re not really allowed to be gentle with yourself.
  • But, you have to acknowledge that you’re learning a brand new skill set, so there is a learning curve.
  • If you’re married, your spouse has to learn to relate to a new version of you and YOU have to learn how to relate to a new version of you.
  • You have no idea what the greatness that’s inside of you that’s dying to get out.   That’s what that entrepreneurial yearning is.

The prescription is fail fast, fail forward and fail frequently.

Make your mistakes as quickly as possible so you start learning from them. Make mistakes that will get you farther down the road to the right path. Don’t be afraid to make mistakes. They are GOING to happen. Learn from them and keep going.

On Business Relationships

  • When we refer to business relationships, all that really is a relationship that is more defined.
  • It is still one more relationship. But, in this case it can be even more imperative because the business relationship needs more clear and defined boundaries in order to be successful because otherwise they can encroach upon the things that are truly important.
  • It can be difficult when you have that entrepreneurial longing and that drive to provide for your family.   It’s tempting to just “go for it” 24/7.
  • At the beginning, J. looked at like he was investing the time 24/7 then so he could take his family to Disneyland later. It took some church discipleship friends to call attention to it and make him realize he needed to dial it back a bit.

You bump left, you bump right, until you eventually learn to go straight.

On Comfort and ‘Security’

  • Without the right safety net and boundaries in your personal and professional life, it could go very badly.
  • At the same time, you can’t shrink back from the problem.   You have to just accept your situation for what it is and figure it out somehow.
  • In J.’s situation, he just had to confront the reality that the corporate world could not accept the talents that he has and those talents are not valued, so he had to figure out a solution somewhere else and make it work.
  • But, he doesn’t look at “Corporate America” as being that safety net like so many do. He looks at those who have a “job” as those who have the greater danger.

Because comfort kills dreams.

  • You will stay comfortable. That’s a human psychological need.
  • If you look at Maslow’s Hierarchy of Needs, if some of those are being met, especially the base ones, people are going to do everything they can to cling to them.
  • We have this misconception that being afraid is bad. But, it’s how we evolved from being cavemen   If you weren’t afraid, you died, so you learned to adapt to the environment. Humans are essentially tool creators and problem solvers.
  • We shortcut that by putting ourselves into a situation where we don’t have to solve the problem. We take the path of least resistance.

Moving At The Speed of Instruction

  1. In his programs J. teaches this principle.
  2. It simply means if I say turn left, just turn left. Don’t ask me why. Don’t wonder what’s going to happen after I turn left. Just turn left because after you get there, you’ll see further.
  3. We make success way too complicated.
  4. We want to know all 12 steps and what’s most important is just to know the NEXT step.
  5. The secret is, you don’t necessarily need to know all the steps because by the time you get to the right turn, you may have to make adjustments to your path.

Value Propositions

When they closed their first deal, it was just so crazy in that they were squatting ourselves and the first offer they made was to an owner who was in foreclosure themselves. They offered to take over the payments and then had to find a contractor to rehab the house and then find a person to pay for it all.

  • He had to make each person a different value proposition in that equation in order to make it work.
  • No one he knew had the $12K that they needed to close. The solution? Find someone with a credit card that had $12K available.   That was the most creative solution he had to come up with initially.
  • The rest was pretty straightforward because there are a lot of people out there who know how to do contracting work.
  • Then, there’s a property manager, who WANTS more properties to manage and is going to find the tenants for you.

J.’s role was to orchestrate and coordinate all of this. He didn’t have the ‘funds’ so coordinating the entire process was HIS value proposition to bring to the table.

At the end of the day, you look at the end benefit instead of the hassle and the struggle.

Today’s Take-Away’s

  • Be willing to ask for what you need emotionally.
  • Be willing to fail fast, fail forward and fail often.
  • Don’t be afraid to look at changing your value propositions.

All of this information is applicable to relationships with your teens, hassles with your significant other, and all business relationships.

You have no clue how great you are until you are forced to display it. When that greatness does emerge, let it flourish. Share it as fast as you possibly can with as many people as you can.

Where Can You Find J.?

A lot of free resources can be found at his site:                                                                                            

For those that want to do an advanced program that is specific to real estate investing, you can go to:

For additional information on Maslow’s Hierarchy of Needs, see

Susie’s Book: