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“Fail fast, fail forward, fail frequently.” With Jason Hartman & J. Massey

Fail fast, fail forward, fail frequently. When we can shed our addiction to looking good, we can now learn. When I got started in real estate, I didn’t have the luxury of looking perfect before I could write an offer. I just had to do it. An offer is just an invitation to a conversation. […]

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Fail fast, fail forward, fail frequently. When we can shed our addiction to looking good, we can now learn. When I got started in real estate, I didn’t have the luxury of looking perfect before I could write an offer. I just had to do it. An offer is just an invitation to a conversation. If they say no, great. What did you learn? Don’t be afraid of frequent failure events. They just help you grow faster.

As a part of my series about “Investing During The Pandemic”, I had the pleasure of interviewing J. Massey.

J. Massey is an entrepreneur, investor, former financial planner, and the CEO and Founder of Cashflow Diary, a training and development company created to educate short-term rental entrepreneurs. Before Cashflow Diary, J. spent years raising capital and investing in all kinds of real estate, including single family homes, multi-family units, commercial real estate, note brokering, cell phone towers, and land eventually earning enough through his investments to retire at 38. While growing his investment portfolio, J. started Cashflow Diary, as a way to pass on all that he was learning.

Thank you for doing this with us! Before we dig in, our readers would like to learn a bit more about you. Can you tell us the “backstory” about what brought you to the finance industry?

What brought me to the finance industry, quite simply, was the need to learn how to produce an income without a job. My wife, when she was pregnant, had a condition called hyperemesis where she couldn’t eat or drink. At the same time, I had a punctured lung and couldn’t walk or talk. That’s called a problem. And yet, we still needed to eat. I needed a way to create passive income. I had a friend share real estate with me, and started learning as I did in terms of finance, investing, and the real estate world. I needed my money to work for me when I couldn’t work, so set out to learn an entirely new set of skills, There was no real long-term goal in mind. My family needed to eat!

As I learned more and earned more with my investments, I fell into financial planning for others. It was there that I noticed a trend. Out of all my clients, there were only three that had a real chance at retirement. They all had one thing in common: short term rentals. That was my clue and set me on the path to find out more. It’s what led me to where I am today.

Can you share with our readers the most interesting or amusing story that occurred to you in your career so far? Can you share the lesson or take away you took out of that story?

The stories at the beginning are all transformative. When you’re squatting in a bank-owned property and your credit score is 398, you don’t even know what you don’t know. What’s funny is that I didn’t know about escrow, what it was, what it meant.

The escrow company called looking for me, because I hadn’t closed escrow. I didn’t know you had to, didn’t even know what that was. Some people find that funny. I find it hilarious looking back.

The lesson: you don’t need to know all the steps. Don’t wait to get started before you take a chance.

Are you working on any exciting new projects now? How do you think that will help people?

One of the things I’ve been consistently doing is helping people figure out how to increase cashflow, no matter where they are in life. A lot of investment strategies are based on long-term wealth building, which is fine…but that’s not going to cut it for people who need more cashflow in their lives NOW. So, I have a year-long program that teaches people how to start, grow, and scale their short term rentals so they can build both cashflow and wealth!

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Jesus is the main one. He’s my strength in all of this.

Steven Gregg is another. He was one of the first individuals to express that I could do more than inside sales. He’s how I ended up doing the Yellow Pages door to door.

There are a lot of things I tried and failed at, and I’ve developed resilience through it all. But it often takes someone else who has faith in you to encourage you along your way. Steven did that for me!

Let’s shift a bit to what is happening today in the broader world. Many people have become anxious from the dramatic jolts of the news cycle. The fears related to the coronavirus pandemic have understandably heightened a sense of uncertainty and loneliness. From your experience, what are a few ideas that we can use to effectively offer support to our families and loved ones who are feeling anxious? Can you explain?

I think a lot of people have learned to use various technologies like Zoom, in order to stay connected. Staying active is important for reducing anxiety, so taking a daily walk is kind of like a little dose of stress-relief.. Drinking tons of water has been a go-to for me since the pandemic started, and just doing my best to get some sleep. Our bodies are kind of in fight mode right now all the time, so anything we can do to relieve stress is important. A weighted blanked has been a game-changer for me.

Ok. Thanks for all that. Let’s now jump to the main core of our interview. As you know the stock market and the economy in general have become extremely volatile and uncertain. Many people “dollar cost average” and put aside a monthly sum into a long term savings plan for retirement, college, or a home purchase. If a loved one or a client came to you and said, “I have been saving and investing $500 every month in an S&P 500 index fund. Over the next few months until the dust settles, should I be doing something else with my money?”, what would you say to them?

Yes, I’d recommend they reconsider.

Right now, the most important thing, in my opinion, is to increase your skill set. If you’re going to invest in something, add more skill sets to your repertoire. You have to learn how to strategically grow your knowledge base in order to create more cashflow and build wealth. The marketplace rewards value creation.

There’s nothing wrong with investing money in equities or whatever else you choose, but in doing so you’re paying for someone else’s education. You’re hoping that the company you’re investing in is going to create more value for you.

Right now, the world’s wealth is being reallocated, everything will be different in the coming months. This is your first pandemic. No one really knows what’s going to happen. Instead of investing your money in someone else’s learning, hoping someone else’s success will get you a decent ROI, invest in yourself, and your own skillset.

What can you learn to do, to build a business around, to create your own economy, so no matter what happens, what crashes, what closes…you have the skills necessary to come out on top!

The number one thing to invest in right now is in your own real world education.

Eventually the economy will recover and rebound. Certain sectors, like travel and hospitality might be hurting for a while. But other sectors, like technology and healthcare, might do very well. If someone wanted to prepare today to take advantage of the future recovery, what would you suggest they do?

I would suggest that they begin asking very fundamental questions: What did we learn is an essential service?

How did those jobs change during the pandemic?

For example, we provide short term rentals to travelers. As travel slowed, and then came to a standstill because of the pandemic, who still needed temporary housing? Healthcare workers. College students who got kicked out of their dorms. First responders who can’t or don’t want to go back home because they’ve been exposed to the virus. Employees who need to work remotely but there’s no space at home.

People thought this would bring the travel and hospitality industry to a screeching halt. It didn’t. It’s not dead. We just had to make an adjustment. There’s a different customer for us to find, to market to, and to serve.

Again it goes back to developing a skillset and mindset that allows you to come out on top in any situation. There are those inside every industry who can still thrive if they get smart.

Are there sectors that provide exciting and lucrative investment opportunities today, specifically because of the volatility and uncertainty?

There are certain things that got unfairly beat up. Each one of us needs the marketplace to break, because if it never breaks, then there’s never a crack for any of us to get in. It just keeps going up and up, out of our reach. When something goes wrong, it’s an opportunity for the little guy to take advantage and get into a market he may have never been able to break into.

Obviously various types of technology will be critical in the months and years to come. Food ordering apps will likely continue to thrive. Virtual communication platforms are set up to dominate. But just a reminder…while there are industries that took a hit, they aren’t permanently going anywhere. Oil, travel, food, cell phones…those will always be around.

In times of chaos, as yourself…what do humans need, and what will humans continue to need? Go invest in (or even better, provide) that.

Are there alternative investments that you think more people should look more deeply at?

Absolutely. We all need to protect our purchasing power. We want to do our best to diversify into something that’s physical or has the ability to adjust with inflation. You have to find something you trust enough to hold its value. Saving currency isn’t the answer. I have to find a place to put my money so it doesn’t lose its purchasing power. You want to have units of production. Obviously, I think real estate, particularly short term rentals provide that, even in times like these.

If a person in their thirties and forties came to you today and said that they have $10,000 that they want to put away today for a long term investment what would you advise them to do with it?

I’d ask them what their ultimate goal is, and then come up with a specific plan to accomplish that. I would obviously take into account, when they wanted to reach their goal, and whether or not this was their only money.

I do know that I’d tell them to Invest in short term rentals. In 12–18 months, they’ll get that $10,000 back and still have a business that provides cash flow and builds wealth. That will put them in a stronger position if things get all shaken up again.

Ok, thank you! Here is a more general finance question. You are a “finance insider”. If you had to advise your adult child about 5 non intuitive essentials for smart investing what would you say? Can you please give a story or an example for each?

#1: Take an art class or photography class. In order to create an image that can hold someone’s attention, you must make decisions. If you don’t, your indecisiveness will make a horrible image. People don’t invest because they don’t know how to confidently make decisions. By learning photography, or painting, or drawing, you’ll learn to make decisions and feel confident in them.

#2: Play a sport. You’ll get used to failure. A football player fumbles the ball, but they get back on the field and keep going. You’ll fail when it comes to investing. You can’t let that stop you.

#3: Play poker. When you play poker, you learn your tendencies when money is on the line. Get to know who you are when the stakes are financial.

#4: Keep a diary. Write down your emotions, how you’re feeling. Get to know yourself. Investing is learning to tap into your intuition. You need to know yourself well for that.

#5 Learn an instrument. This requires a significant amount of patience. If you want to really make money from your investments, you will need to study, practice, and be patient.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Fail fast, fail forward, fail frequently. When we can shed our addiction to looking good, we can now learn. When I got started in real estate, I didn’t have the luxury of looking perfect before I could write an offer. I just had to do it. An offer is just an invitation to a conversation. If they say no, great. What did you learn? Don’t be afraid of frequent failure events. They just help you grow faster.

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. 🙂

So for me, there are four steps to making an impact. 1.) Watch me do. 2.) Do with me. 3.) Do alone. 4.) Teach another.

That is the process. Depending on where you are on your journey, you might be at stage 1.

That’s fine, but don’t stay there.

Don’t just learn and watch and take. Keep going to all four steps of the journey. The giving back stage is the best. We need more people going all the way and giving back, paying it forward, passing on what they’ve learned.Be a job maker, not a job taker. For the economy to heal, and thrive, a significant amount of jobs need to be created.

Your idea has merit. Try it, test it. Let the marketplace tell you if it is worthy. Go find out. Don’t wonder, don’t hope, don’t doubt — just go. Over time, as you grow, you’ll be able to create jobs and make a difference.

Thank you for the interview. We wish you only continued success!

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