Invest In Yourself: Building Up Your Fundamentals So You Can Find Success In Your Industry With Jason Matthews

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If you really want to succeed in your industry, you need to have a knack for learning. The ability to just constantly educate yourself. Read every book, do research, get mentors, or listen to podcasts. Do what you have to do so that you can succeed and don’t make mistakes. Strengthen your fundamentals and move up from there. Join Tim Herriage as he talks to real estate executive Jason Matthews about his journey into real estate development and construction. Discover how he did it by investing in himself. Learn how he put some of his sports philosophies into creating a successful business. And find out how Jason is helping ethnical minorities break into the real estate industry. Start educating yourself today!

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Invest In Yourself: Building Up Your Fundamentals So You Can Find Success In Your Industry With Jason Matthews

I’m here with my good friend, Jason Matthews. Jason, thank you for coming to town.

Thanks for having me. I’m looking forward to it. One of my favorite guys.

I don’t know about all that, but let’s start off. Why don’t you tell the audience a little bit about yourself.

Jason Matthews, born and raised in Los Angeles, California, and played high school and college basketball. I used that life of basketball, that vehicle, to guide me through my business career. I’m now living in Tampa. Many years as a real estate investor. I’m married. I’m a dad of three, great kids. I’m happy to be here in Dallas, Texas with you.

I’m glad you’re here. I like to start with what I call the Bottom-Line Up Front. Imagine someone’s reading, they’re excited, they have to stop to do something for 5 or 10 minutes, and they forget to go back to reading. Let’s try to find a way to tell them the most important things happening in the market now, your opinion about that, things you think they should be focused on, things they should be doing, and maybe some things they should be avoiding.

The most solid advice I can give people at this point in time is to focus on their education. You have to dig deep into the fundamentals because the fundamentals will teach you how to make adjustments. In the real estate market that we’re dealing with right now, things, underwriting guidelines, and values are changing so rapidly. You got to drill down into the fundamentals and know how to make adjustments.

Our approach has been to study what’s going on, relying on the knowledge that we’ve gained over the last 25-plus years, and make the right adjustments. We’ve done a great job so far of doing that. We also have an action plan with more rate hikes to come. We also have an action plan with looking at some different uses for our short-term rental portfolio that we have. That’s what it’s going to take to be successful and get through the next few years.

I’ve invested in my education on a continuous basis. I’ve invested in a couple of courses that have helped me. I’m investing in some more excellent coaching. I’m in a phenomenal real estate mastermind group that has a lot of talent, knowledge, and experience. I came into the year 2020 expecting to have to make these adjustments, expecting to build our infrastructure a lot stronger with the growth of our portfolio. That’s what we’ve been able to do. It’s worked well for us.

I got to meet you in the Boardroom Mastermind in Denver in June 2022. You were immediately one of those impressive human beings, not because you’re a short man because you’re rather tall, but because you were soft-spoken but intelligent. I like to have intellectual conversations at times. I want to go back to something you said in the bluff. You talked about education and a team. It seemed like you were leveraging other people’s knowledge. Going back to your time in sports, because we talked a lot about that when we first met, what is it about having a team specifically in times like this that helps you?

To be a part of a team, to have a team, I was fortunate. My dad put me in team sports at four years old at tee-ball. My dad was my Little League coach for ten years. It’s a phenomenal experience. You have to be on time and prepared. It’s not all about you. You can’t win the game by yourself. My dad was big on sportsmanship. Knowing how to get along with your teammates and realizing that even if you’re right, it’s okay not to have to tell everybody that you’re right. That transferred into being a businessman.

I’ve never liked the vertical management of our businesses and being an entrepreneur. I’ve always preferred to work in a team. Whether I agree with it or not, I value the input from others on our team because they have different perspectives. They live in different neighborhoods and cities. They’ve had different experiences, personal experiences, family experiences, and business experiences. I want to look at the whole global view of what’s going on out here. I believe that a major reason why I’ve been able to stay in this industry for many years through all the real estate cycles and ups and downs and things of that nature is that I am willing to listen and learn from a variety of different people.

I’ll give you a good example. When I was younger in the business, if I had a major business decision to make, I would intentionally ask one of my mentors’ opinions. I would ask one of my colleagues’ opinions. The third person I would ask would be someone that’s not even in the real estate industry. That was my process. They gave me three different perspectives. I added my perspective and then I move forward with the decision. That was a practice that I used that helped me out a lot. I still use that practice now.

How much of your financial background has guided that decision process?

My financial background has been tremendous. As a kid, I love math. My mother was an accountant for 40 years. I grew up in an accounting household.

That’s why you love math. You weren’t bringing home bad grades in math.

No, not in math. Other subjects, but not math. My mom worked at the CPA firms in Century City. I would go in and volunteer during tax season. I knew I did not want to be a CPA or an accountant, but I love numbers and math. The way that I learned math was pretty interesting. Having a dad involved in sports, I would always watch baseball, basketball, football, and anything on sports tv.

My mom would always be like, “You need to be more rounded. You need to read more books. You need this, that, and the other.” What my mom didn’t understand at the time was that baseball, basketball, and football helped me learn fractions and averages. Someone is 1 for 3, 33%. That’s how I learned. Someone was 8 for 10 from the free throw line, 80%. I literally am enjoying watching sports but learning math at the same time.

I have to stop you there. Aaron Judge hit his 62nd home run and broke the American League home run record against Texas down here in Arlington. It was interesting, I was doing an episode and I brought that up because now he’s the American League home run winner. He’s hit 62. Can you guess how many strikeouts he’s had?

Probably 250.

It’s like 120. He’s batting 300, 1 out of 3. The best home run hitter ever in the American League, 1 out of 3 times, he sits down. Too many entrepreneurs see the home run ball. They see Michael Jordan making the game-winning shot because that gets replayed over and over. They run their daily lives looking for that game-winning shot when they don’t want to go through all the arduous practice it takes to be ready for that big moment.

It takes a lot of practice. When I was younger in the business, I was a voracious reader. I was reading magazines. I read the Wall Street Journal every day. I read every real estate and business book I can get my hands on. I was doing research. I wanted the knowledge. I wanted to know what I was doing. I wanted to cut back on my mistakes. I was recruiting mentors right and left.

That’s what has helped me stay in the industry for so long. I’ve worked on single-family homes. I’ve worked on football stadiums, baseball parks, convention centers, hotels, hospitals, dorms, multifamily, and pretty much anything except for industrial. I did all that in my mid-twenties when the city of Pittsburgh went through a tremendous building boom. I was a cofounder of a construction supply company. We supplied a lot of different construction materials to various projects.

We’re going to talk about hero ball and construction projects. I want to help people differentiate between short-term rental, vacation rental, temporary housing, long-term rental, and all that. I also want to talk about leadership and community impact. When we were in Denver sharing dinner together, you talked about hero ball.

You said it was the biggest struggle in your business not being a ball hog, but when there was a problem in the business, grabbing the ball, dribbling down, it’s the guy that feels like he has to score 50 points for the team to get to 100. Talk about your struggles with hero ball in your real estate business and what you do to overcome them. A lot of entrepreneurs have the, “If you want it done right, you got to do it yourself.” To me, that’s a surefire way to keep having to do it by yourself.

It’s true. There have been several instances in my real estate career where you have true deadlines and stuff to get done. I was always taught that it’s never more important to anyone than it is to you. When I see something lagging in a process and something not moving the way that I felt it should be going, I would jump in and “play hero ball” to do what I know how to do to move forward and get it done. That is not a lasting business practice you can continue to do as your business expands.

In the last few years, our business has expanded tremendously. The hero ball approach is not necessarily going to work. I’ve been in a positive transition away from hero ball and being in Kent’s boardroom group with you yourself and Zalo and other great entrepreneurs I’ve met has motivated me to get away from hero ball and remain disciplined.

You own millions of dollars in houses. Aren’t you worried you’ll lose it all?

I’m not worried that I’ll lose it all because, at this point, I have enough confidence to know that I have a team that’ll help us figure it out. It’s not just me figuring it out. I do manage our property management companies. I do look at our calendars frequently. I do pay attention to what’s going on in the market. I’m comfortable with those things.

I’m a pretty good risk manager so I can see some things before they happen and mitigate them early on and not let them get full throttle where it becomes a major issue. If I need to go out and raise more capital, I’ll go out and raise more capital. If I need to go and pull in a new technology provider, I’ll go and I’ll pull the technology provider in and let them do what they need to do and manage the work that they’re doing and work with them as a team member.

How important is it to have another voice in the locker room as you’re growing your business and your team?

Our portfolio has increased to the point that it is now. You have to have those other voices because I cannot see everything. My wife, my business partner, can’t see everything. Years ago, when our portfolio was smaller, we could see everything. Now, we cannot see everything. You do need those qualified team members to say, “Take a look at this. Don’t do that. You may want to reconsider this. This is a piece of the puzzle. We need to make this happen.”

I am much more open to hearing from those qualified team members. I’m saying qualified. As a sports analogy, my teammates that put in the work in the offseason, I trusted them in the last two minutes of the game to pass them the ball or to rotate on defense because I saw them put in the work in the offseason. If they did not put in that work, then no, I’m not going to trust them as much in the last two minutes of a game.

I was talking to someone. They’re part of another mastermind here in Dallas. This gentleman, Dan, had been telling his wife the stuff he had been hearing at the mastermind for a year. For some reason, she was opposed to it probably because he was hanging out at the bar a little too much when he was at the mastermind. It was a big party.

It was funny, he said he got her to go to the event last October 2022. She starts saying, “We needed this.” He’s like, “I’ve been saying it for a year.” You heard the guys say it, and I told you the guys that, but it’s that other voice in the locker room. Let’s shift to your investment thesis. You went from being a financial planner to owning multi-unit Airbnb projects in Tampa. Was that a direct transition or was there anything between?

A lot in between.

I cut you off when you were talking about your construction business in Pittsburgh.

One of the biggest gifts I’ve ever received in business is when the Mayor of Pittsburgh, Tom Murphy, a great guy, and his development guy, invited me to be a volunteer member of the Downtown Pittsburgh revitalization plan. They were redeveloping downtown and the riverfronts. I was 26 years old. Talk about education on commercial development. They built $6 billion worth of development in a five-year period of time. My good friend, Curtis Aiken, and I had a commercial construction supply company. We met with architects, engineers, international general contractors, and architectural firms that design 20 football stadiums and 15 baseball parks.

I’m in my mid-twenties and I’m in all those meetings. I’m talking to precast concrete manufacturers. I met steel plants in the middle heartland of America, in the middle of the State of Kansas where the beautiful green grass is taller than me at a steel beam manufacturing plant. I realized what was going on. I said, “You will never ever get this opportunity ever again in your life.” I was in the moment. I seized the opportunity. That’s how I truly learned real estate development and real estate construction.

Was the opportunity the supply company or being involved in the redevelopment?

Being involved in the redevelopment and education. Don’t get me wrong, the money was great, but I knew the knowledge was worth much more than the money we were making. To be that young and be exposed to that, I was truly in the moment. I would come home after working eighteen hours, play with my son, and fall asleep in my suit and tie on the floor of my living room. I was that exhausted. I would get up the next day, go out, and do the same thing.

That experience is what has carried me throughout my entire career because I can look at a project, I can look at a relationship, and I can look for a solution. The contacts I developed were where I can call and get the answer. That experience in my career was unbelievable. I was able to parlay that experience into project management work, owner’s rep work, and oil and gas work. My wife and I worked on a billion-dollar oil and gas project strictly because of the experience that we got from working on this massive $6 billion development in Downtown Pittsburgh and the riverfront. We did a phenomenal job. From the reputation I built from that, we were afforded several opportunities in the oil and gas industry.

I shared this with you before, but I’m always telling my boys, “You don’t have to know where you’re going. You just have to be going somewhere.” I know that from Pittsburgh, you went to LA.

I’m born and raised in LA.

You played ball for Pit.

Coach Calipari sold me the dream. He got me to go 3,000 miles away from home.

You know I don’t know who that is.

Head Coach of Kentucky. One of the best that has ever done it. He got me to go to Pit. I got an Economics degree and stayed for about 30 years and then moved to Tampa a few years ago.

Why Tampa?

My oldest child, my son Brandon, has a mild form of autism. One of my good friends, Coach Orlando Antigua, got the head coaching job at the University of South Florida. He called me up, “We have phenomenal programs for my nephew on our campus for adults with autism. You need to bring him down to campus and have him check it out.” Brandon was in the ninth grade at the time. As soon as school got out in June, I flew down to Tampa. I took him to the basketball facility. I took him all over campus. He loved it. We had a plan that once he finished high school, the whole family was moving to Tampa for his next step in life. He’s been thriving ever since.

You are now the second person in a month whose son was autistic or had a form of autism. How does that impact your business life?

It has a tremendous impact. I talked about this by saying that I’ve always put my kids first. My wife and I don’t miss practice, games, parent-teacher nights, and things of that nature. We’re entrepreneurs. We don’t miss anything. My son, Brandon, has a love of basketball. He’s a math and computer geek, but he has a love of basketball. He played at the YMCA when he was little. He played four years of high school basketball. He’s now starting his sixth season as a University of South Florida Men’s Basketball Team Manager. We will never take it away from him because he loves it so much. He’s loved all over campus, not just by the team and the coaching staff.

He even works the away games as long as I go with him. Real estate affords me the ability to make sure that he’s able to seize every single opportunity that has afforded him. Now, also having a daughter who’s a Division 1 Lacrosse Player at Howard University, real estate allows me to not miss her games. My little child, which is why I’m here, hanging out with her best friend. Real estate allows me to be involved in our kids’ lives.

Let’s talk about perspective. There are a lot of days that there are going to be a lot of problems. This was one of those days for me. I traveled for 3 or 4 days in a week, phone calls, a stock market crash, rehab problems, a million-dollar house that won’t get finished, a wood floor guy wants to draw, and an electrician wants to draw. How do the important things you discussed help you keep a level head and an element of perspective?

Watching my son as the happiest person I’ve ever encountered in my entire life. He gives off this positive energy that other students see. Coaches, players, and anyone that’s in his world speak about the positive energy that he gives off. The perspective of I have a son who’s high functioning but with autism, he’s happy every minute of every day. This dude is happy. He never has a bad hour. I’m like, “How does he do this?” There have been several interviews that have been done at the local news in Tampa where they do an autism special. Every year, there’s an autism basketball game that USF does.

It’s phenomenal to create awareness. They interview the players and the coaches and they’re like, “I come in. I see Brandon. He’s full of energy. He’s happy. No matter what’s going on in my day, I look at him, all that goes away.” That’s what happens in our household. No matter what kind of day I may be having or my wife may be having or his sisters may be having or anything of that nature, being around him puts it all in perspective.

Thank you for sharing that. It’s time for the Money Minute. Imagine it can be anyone you talk to, young Jason getting out of high school, old Jason playing hero ball, or a young entrepreneur like Kevin Dixon, who will talk about your mindset regarding that. You’ve got up to 60 seconds to impart the absolute best of Jason Matthews to the audience.

I would want to focus on education. Education in the real estate business has carried me. It prevents panic, bad decisions, and making short-term decisions that aren’t good for your business. I’ve always tried to focus on the educational side of things, talking to people that are much smarter than me, reading magazines, reading books, reading any article online, and watching YouTube videos. That’s what’s carried me throughout my entire career. That’s probably the best advice I can share with any entrepreneur or real estate investor. Education prevents panic. It allows you to make adjustments and pivots when you need to. That’s what you want to focus on in order to stay in this business long-term.

That’s important because I come from a family where education was not incentivized. It was not talked about. I failed high school because of attendance and ended up graduating out of summer school. I ended up joining the Marine Corps because I was going nowhere. When you look back, the way I’ve been able to achieve what I’ve achieved is a thirst for knowledge.

One of the greatest compliments someone ever paid me was from my mentor, Jeff Tenison. When I was sitting at a table and they were reviewing the corporate model at Blackstone, I had no idea what anyone at the table was talking about. No clue. I was like, “Can you explain to me what that means?” They’re like, “Yeah.” I was like, “What’s that?”

I have no problem being the dumbest guy in the room. As a matter of fact, I consider it a badge of honor. The key is not being the dumbest guy in the room for too long. Educate yourself, outpace the people in the room with you, and then get in a different room. Jason, when we had dinner in Denver, you had a business partner of yours, Kevin Dixon, with you.

You talked a lot to my wife about trying to help other young African American men be successful. You talked a lot about your obligation to that community. It seemed like a deep passion of yours. I feel like we’d be remiss without addressing that. Can you talk a little bit about what that means to you, how important it’s to you, and some of the things that you think of other entrepreneurs of any other minority races? Talk to me about your thought process on that.

I’ve extremely benefited from mentors all my life, playing sports, Magic Johnson, Marcus Allen, Darryl Strawberry, and Eric Davis. All throughout the LA community, any type of youth program, sports afterschool program, they were out there. You knew who they were. They were talking to all of us. It had a tremendous impact on me as a kid, even though my dad was in the household. Dad was there every day for my brother and me. Mom was there every day, a great family, but my high school coach and my AAU coaches were phenomenal people.

By the time I got to college, I had already benefited tremendously from this specific model of mentorship. All that mentorship I got, got me into college and got me a college basketball scholarship, and now have an opportunity to get a free Economics degree in college. I used the gift of basketball as the vehicle to guide me throughout my life.

I understood that as a seventeen-year-old freshman because at twelve years old, I was a UCLA ball boy. My best friend and I, Josh Oppenheimer, were UCLA ball boys. We would see the former UCLA players sitting in the stands with men and women in business attire. We didn’t know they were called alumni until we start getting recruited for college basketball scholarships.

I learned the mentorship scenario at a young age. I said, “If I ever get in a position where I can mentor people, I would.” For me, it’s always been a passion to work with women, people of color, and anybody. I’ve been involved in youth development for over 30 years. It’s a major passion of mine. I love working with kids. When it comes to the real estate industry, 97% of real estate professionals are White males. Less than 1% are people of color. We have a long way to go.

If I have some answers to the tests and I see someone that’s serious, I’m willing to do what I can to help push them forward. I do work with a lot of ethnic minorities. I work with a lot of women. My wife will tell you that real estate attorneys, bookkeepers, property managers, realtors, and lenders because the women I work with get it done. They don’t play around. I encourage them. I challenge them to step out of their comfort zone to reach. The ethnic minorities that I work with in real estate, I challenge them to step out of their comfort zone to reach their full potential.

Some of them have gone on as surpass what my wife and I have been able to do in real estate. I love to see it. They had that passion and fire. My wife and I were able to help them along their path. It’s something that I will always do. I have two daughters that have an interest in the business. My wife and I have pushed them along. They have their short-term rental Airbnb properties. I explain to them, “Your private school tuition isn’t coming out of my pocket. It’s coming from those properties.” They understand that.

It’s one of the things that RCN Capital‘s committed to diversity. After I did the first week of recordings for this show, I realized I had called all of my friends in Dallas, which all happened to be White guys. The pool of experts to fish from is not limited. You have to intentionally look. Since that time, I’m proud to say that less than 50% of the guests have been White men. We’ve been focused on trying to get more women and more people of color.

If you’re reading and you know of an entrepreneur, specifically in the real estate field, I don’t limit everything to the real estate field for this show, but we would like to stroke the core audience’s attention, reach out. If you’re reading and you know someone, tell them to call me. I don’t fit the traditional mold either. I come from an East Texas family. My dad’s cousin was like one of those unsolved murders where they suspected the town sheriff had done it.

I grew up in a family with no parents, no dad around. My older brother, I’ve said on The Underdog Podcast, I’ve seen him dead multiple times, heroin and drugs. I know how hard it is for someone to punch through. I was at Blackstone. We were doing introductions one day at the table. I never forget that it was like Cornell, Harvard, Stanford, Princeton, U Penn, and Yale. They get around to me and I’m like, “Marine Corps.”

I completely agree with you. I’m going to put a pin in this issue for now. Number one, I want to be clear, I did not invite you here because you’re a Black man. I invited you here because I respect you and I wanted to share your story of short-term rentals. You called me one time, and one of my loan officers upset you. You were so calm. I was like, “He may have been the calmest, mad person I’ve dealt with all week.” It was all about working towards a solution, working towards overcoming, working towards like, “Let’s get to a yes. Let’s figure it out.” I appreciated that about you. I love staying in touch with you. I’m grateful that you came to Dallas and spent your time with me.

I had to come to the show. You invited me to the show. How am I going to say no?

I am not going to do Rapid Fire because I wanted to go ahead and address that other issue. You made an impact on me when we sat down in Denver and I appreciate it.

You made an impact on me. Your wife is in my real estate investor hall of fame.

We are going to cut this and frame it. It’s going to be one of those repeating picture frames in the house. We’re out of time. Thank you for coming. Please, do stay in touch.

Thank you for having me. I appreciate it.

Thank you for stopping by. Thank you for coming back. We’ll see you next episode. Remember, your network is your net worth. You’ve been growing both.

Important Links

• Jason Matthews
• https://www.JasonMatthews22.com
• RCN Capital
• Tim Herriage’s previous episode on The Underdog Podcast

About Jason Matthews

Jason is a seasoned real estate executive with over 27 years of real estate experience. Most notably in leadership/project management, repositioning projects, development, real estate finance, asset management, and build-out of a short-term rental portfolio in Florida. Jason has a proven track record of achieving revenue, profit, and business growth. He has been successful in driving results in both operational and financial spectrums of real estate.

As the owner of a Real Estate Project Management firm, Jason has serviced clients from small non-profits to Fortune 500 corporations in Washington D.C., Pennsylvania, Texas, and Florida markets. The firm focuses on real estate consulting, project discovery, and investment analysis.

Since 1995 he has worked on major projects that include: sports stadiums/pro sports practice facilities, convention centers, hotels, theatres, hospitals, airport cargo facilities, office buildings, student housing, grocery-anchored strip malls, grocery cold storage facilities, residential development, multifamily housing, land development, condo conversions, Billion Dollar Oil & Gas projects, landman and engineering services. Add in 12 years of corporate procurement experience that includes writing and managing Corporate Supplier Inclusion Plans. This spectrum of experience culminates in Jason’s savvy vision of recognizing opportunities, commitment to risk mitigation, and adaptability to changing markets and economies.

His dedication to mentoring is evident, and close to his heart. Jason provides financial fitness education and real estate investment coaching to people from all walks of life. Aside from mentoring individuals, he volunteered on behalf of the Pittsburgh community; driving impactful change as a member of the City’s Equal Opportunity Commission. He significantly contributed to the creation of the urban Master Plan and Community Collaboration & Inclusion Plan (CCIP) for the redevelopment of the Lower Hill District in Pittsburgh, PA.

The following podcast program is furnished by RCN Capital LLC.  The information provided is for general educational purposes only and does not constitute any legal, tax, financial, investment or other professional advice. The views, thoughts, and opinions expressed of any speaker are the speaker’s own opinion and do not represent the views, thoughts, and opinions of RCN Capital LLC.   No information contained in this episode should be construed as financial, investment or legal advice from RCN or any individual, author, host or guest. You should always consult a financial advisor before investing.

• Diversity
• Educate Yourself
• Hero Ball
• Invest In Yourself
• mentorship
• Real Estate Construction