As part of my series about the “How Business Leaders Plan To Rebuild In The Post COVID Economy,” I had the pleasure of interviewing J. Massey.
J. Massey is an entrepreneur, investor, 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.
J. eventually grew bored, and started learning about short-term rental strategies. Since this was the one type of real estate investing he had not ventured into, he gave it a go. Today he owns and operates 34 short term rental units, and has shifted his educational company to focus on training real estate newbies and seasoned pros, how to operate a short term rental portfolio. J.’s built a community of thousands of like-minded people from 16 countries and is the host of a top rated podcast. He’s spoken on countless stages, and has helped thousands of men and women across the world, find financial freedom and lifestyle freedom through real estate investing.
Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?
Sure! I won’t go WAY back, but I will go back to the point where things got interesting. Twelve years ago, when my wife was pregnant, we found out she had a medical condition that made it impossible for her to eat or drink during pregnancy. Shortly after that, I ended up puncturing a lung. Because I have asthma, this made breathing even harder. We were both unable to work, and struggled to make ends meet. We were squatting in bank owned property, and things were NOT going well. I was flipping items I would find at garage sales on eBay in order to eat, when a friend told me that investing in real estate was just like that, only with houses. At the time, I had ZERO money…like we owed people money. I also had a credit score of 400, which made real estate investing seem like a far fetched idea. But, my friend told me to trust him, and I did. I started learning about real estate and made my first few deals within a few months. This was in 2008, when the housing market was crashing and getting INTO real estate was not the best idea. Interestingly enough it became the year that radically changed my future. As I began making deals, I was hooked. I knew I no longer wanted to have my income tied to the number of hours I worked, and real estate enabled me to disconnect the two. Over the years, I did every type of real estate investing out there. By age 38, I was all but retired, bored, and teaching others about real estate investing when a student asked me to look at his short term rental strategy. Short term rentals were the one type of real estate I had never invested in, but the numbers he had were compelling. So, I started my own short term rentals. Today I have 34 units in operation, that generate over 7-figures a year, and an education company that teaches others how to create both income and wealth, using short term rentals as their real estate investment strategy.
Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?
I’ve made so many mistakes in the realm of “you don’t know what you don’t know.” The funniest one that comes to mind is when I had no idea what the word “escrow” even meant. When I was just starting, I hadn’t bothered to learn details. I would go to a networking event and use my script and wait for someone to say “yes.” At one point, I found someone willing to sell their house, and I needed to become the buyer. At each step of the process, I’d go and ask my friends, “What does this mean? What do I do now?” And they’d help me out. I made it all the way to the part where I learn that now I “open escrow.” My friends told me to call a person and give them documents. I did. Time went by. I did nothing. The escrow company called: “Are you going to come by and close escrow?” Sure! I had no idea what that meant. I thought it was something physical I was closing on. I had gotten pretty far without ever learning the word “escrow.”
I’ve learned over the years to give myself the freedom to look stupid. We humans have an addiction to looking good. We won’t tell people we don’t know. When I was first starting out, I needed to eat. I didn’t have the luxury of not looking stupid.
Is there a particular book that you read, or podcast you listened to, that really helped you in your career? Can you explain?
Naturally, the Bible comes to mind. It’s the best business book on the planet. If for no other reason, it gives you perspective. Jesus, of all people, didn’t even have a close ratio of 100%. If that doesn’t give you freedom to go and try and fail, I don’t know what does.
Another book is The Science of Getting Rich by Wallace D. Wattles. It’s so old you can download it for free. There are a number of lessons in that book that are germane for any era, especially when you’re trying something new and wanting to become a different person.
Awaken the Giant Within by Tony Robbins is another one. We don’t encourage one another enough. When we have an opportunity presented to us, we don’t think we’re the person for the job. We’re afraid. This book gives you permission to believe in yourself and what’s inside of you.
My favorite podcast is The Real Estate Guys. They’re a great mixture of action and higher level concepts. They’ll tell you that you have to be an entire business person. Real estate isn’t just about the property. It’s tied to politics and the economy and consumer habits and other important things you need to know.
Extensive research suggests that “purpose driven business” are more successful in many areas. When you started your company what was your vision, your purpose?
I won’t say that my company started with a vision to serve people. When I was getting started, it was about eating. My family was squatting in a bank-owned property; our credit score was abysmal; we were choosing between electricity and food; my wife was pregnant and suffering from hyperemesis; I had punctured a lung and developed pleurisy; we were selling our personal possessions on eBay. We were a wreck. The need to eat was my drive.
Along the way, I discovered that other people thought what we had done was special. We completed our 15th transaction so quickly. Someone pulled me aside and explained the statistics and how not normal this was.
A year or so later, I realized we could make a difference in the neighborhoods around us where I used to live, where people looked like me. I could make it possible for kids in that area to go to a better school, have a better life. Even though I would never meet most of them, I could have an influence in their lives. Now, that’s what drives me.
Eventually, I started training other people, transferring my skills and talents to others. That mission has taken hold of me, but it was a process, an evolution. It wasn’t a clear vision at the beginning because all I could see was my own poverty. Only after I got past that, could I elevate my vision.
Do you have a “number one principle” that guides you through the ups and downs of running a business?
I wish there was one principle that summed them all up. I have several at the forefront. One is to understand and believe at your core that suffering leads to perseverance; perseverance leads to character; character leads to hope; and hope doesn’t disappoint.
We all want to have hope, but the way to hope is through suffering. On the way to hope, you develop the perseverance and character you need in life. They aren’t things you have naturally. And you can’t bypass the suffering and hope to have a meaningful life.
Thank you for all that. The Covid-19 pandemic has affected nearly every aspect of our lives today. For the benefit of empowering our readers, can you share with our readers a few of the personal and family related challenges you faced during this crisis? Can you share what you’ve done to address those challenges?
I have ADHD as well as autism. The combination of the two can be challenging to deal with when something new comes along that’s fascinating — not just a distraction, but an obsession. Learning to control that impulse, that desire, and discipline myself to do activities required for my business first, is my biggest challenge.
As entrepreneurs, we have to protect our mindset. Our capacity to think rightly will get us through this or will be the reason we quit. I tell people two things that will keep you in the right frame of mind: 1.) Get enough sleep and 2.) drink enough water. I got a water bottle that flashes and helps me remember to drink regularly. It sounds so basic, but I needed that kind of accountability.
And I love the wellness devices that allow us to track everything we do inconspicuously. Telling me how hard to push today. Empirical data helps me a ton, so I don’t end up putting myself in the hospital by trying to do too much.
Increased use of technology is everywhere. I’ve added new skills, because the marketplace has changed. I’m putting my brain to work, constantly learning. Adding new skills is a requirement, not an option. I challenged myself recently to go live on YouTube and Facebook for 30 days straight. I’m producing YouTube content in response to the demand, even if I don’t know what I’m doing yet. It’s important to get comfortable in the space of moving forward without all the answers.
Can you share a few of the biggest work related challenges you are facing during this pandemic? Can you share what you’ve done to address those challenges?
My biggest challenge as a short term rental house provider is easy to identify. During the week of March 12 to March 15, we saw $80,000 of monthly revenue disappear. Fortunately, on the good side, it wasn’t all of our revenue. On the bad side, it still hurt. It got our attention and made us focus like never before. The reality is that we built that revenue over time. Over a span of four days, it was gone — and with no perceived way to rebuild. Now we have to rebuild it with none of the original tools.
We refunded 100% of people’s money, in spite of previous agreements. The travel restrictions meant we lost all our income from business travelers from other countries. What became evident was that we had to find a way to reach the customers who still had a need. We reached out to nurses and other medical personnel and let them know we have places to stay.We contacted Universities with international students stuck in here with no place to stay. Our network through our training programs covers every state and could probably help every hospital.
We have what it takes but don’t have the connections. It was harder to get in contact with universities to tell them to send their students to us. How could we reach the firemen and policemen who don’t want to go back home? Or Grandma and Grandpa who don’t want to be in their assisted living home where there’s an outbreak? Or parents working from home with kids in a house they never intended working from?
The people are there, and they have a need, but we hadn’t built a marketing channel to contact them in this kind of a situation, and now it’s upon us and we can’t easily connect. We’re still in the process of working through that today, digging for referrals and diversifying customer acquisition methods. It’s been tough.
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, fear, and loneliness. What are a few ideas that you have used to offer support to your family and loved ones who were feeling anxious? Can you explain?
At the beginning of all this, there were so many social media posts and commercials saying “in these uncertain times.” It really started to get on my nerves. I have ADHD and autism. When were times ever certain? It doesn’t sound like much of a comfort, but times have never been certain, especially not for me. That realization helps me not freak out. Part of the freak-out is due to the desire for things to go back to where they were — and to escape pain and discomfort. I tell people: Look, we’ve been here before. Change is not new. This change is definitely more sudden and shocking. You were caught unaware. But catch your breath. Since this is going to be the way it is, what are you going to do? This has allowed us to start offering a path — an unforged one — but we just got out the machete and started moving forward and making that path ourselves.
Obviously we can’t know for certain what the Post-Covid economy will look like. But we can of course try our best to be prepared. We can reasonably assume that the Post-Covid economy will be a trying time for many people across the globe. Yet at the same time the Post-Covid growth can be a time of opportunity. Can you share a few of the opportunities that you anticipate in the Post-Covid economy?
There are a ton of opportunities, and you don’t have to wait for “Post-Covid.” You can start “During Covid.” In any crisis, there are three stages: during the crisis, after the crisis, and the new normal. Each time you switch to a new phase, there will be new opportunities. I’ve always said that, where there is chaos, there is cash flow. This will be no different.
Thirty million people have filed for unemployment. Separation from your previous employer is what gives you access to your 401K. There’s opportunity there. Each one of those people who are unemployed have the chance to design their life, to consider that there’s something else they could do right now.
Do a quick search for equipment related to podcasting or streaming online. It’s all out of stock or severely marked up. Manufacturers weren’t expecting to have to triple up on equipment like this. The opportunity is definitely online.
In the real estate market, there will be opportunities in the apartment sector. People will lose homes because they can’t pay their mortgage, and they’ll need apartments. We need to rebuild something instantly that took decades to build in the first place, but with none of the same tools and a bunch more restrictions.
Business models that depend on volume and density are in trouble — restaurants, hotels, conference centers. There will be some hotels that won’t open again. It’s going to be awhile before a number of individuals are willing to get on an airplane and travel and congregate in something as simple as a hotel lobby. I think people who provide short term housing will have an advantage because we’re smaller, because there will be less people around. We can cater to more specific needs. This will create a unique window.
The economy will reorganize itself to its highest and best use. Most of the new opportunities will have very little to do with how much currency you have. That’s encouraging.
How do you think the COVID pandemic might permanently change the way we behave, act or live?
How much time do we have? I think one of the most basic questions is: Will we ever shake hands again? Right?
Consumer habits have already changed, and we won’t be going back to the way it used to be. People are going to order more food in. Amazon will win. Schools for kids are basically germ factories. How will they pivot? Distance learning will become way more accepted. Commute times will probably get better. Will we ever go to the movies again?
How many employees have recently learned that they actually can work from home? How many CFOs are seeing increased productivity from people not at the office? And it’s cheaper. “Maybe we don’t need all these bloated office expenses,” they’ll say.
We’ll do more with less. And it will become normal. Some companies will lose, because they won’t make that shift. Their higher operating expenses will be the end of them. Everything is impacted. It’s all connected.
What about the environment? The wildlife is freaking out and coming to visit us. They’re asking, “Where are they? They still here?” I’m no climate expert, but something positive has to have come from this. It will be fascinating to see how everything is affected.
Considering the potential challenges and opportunities in the Post-Covid economy, what do you personally plan to do to rebuild and grow your business or organization in the Post-Covid Economy?
One of the most important things to do right now is to listen to the marketplace. The appetite for content consumption has increased. If you have a business, you need to educate your market to dominate your market. You’ve got to produce content — good content — and a lot of it. Whether it’s written, video, audio — we do all three. If you don’t produce more content and provide education, you’ll become irrelevant faster. We are increasing our content production schedule. We have shifted to live streaming, more frequent content production, and have become more structured. I have to learn a new skill that’s not naturally in my wheelhouse. I accept the challenge.
Similarly, what would you encourage others to do?
Two things: believe and build. Believe you can, that you’ve always been able to. And build. We will never outearn our personal growth. In a very contrarian way, because of the pandemic, you have the unique opportunity to fail and not be criticized. If you start something right now, and you tell all of your friends about it, and it fails, you can always say, “You know, Covid-19.” And they’ll accept that. They were there, too. It gives you the freedom to go fail.
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. One of the most important skill sets I continue to improve is how to fail. We have vilified failure, made it something to be avoided at all costs, yet all success is built on a mountain of failures. We’ve also made it personal. I’m a failure. No, you’re not. You had a failure event. You are not a failure. The expectation that we’ll never fail is not realistic. Success never happens because you got it right the first time without help. It comes from failing forward. We can lose touch with how important failure is. Overcoming failure is how you become someone people want to remember. Failure is the way through. It’s a more exciting way to live.
How can our readers further follow your work?
You can connect with me in a number of ways, but the simplest would be in my free Facebook group where I do weekly live trainings. You can check that out here. I also release at least two podcasts each week, so check out Cashflow Diary wherever. You listen to podcasts!