Kyle Matthews shares how getting “cut” from a dream career in professional sports ultimately led him to founding the largest privately held commercial real estate brokerage firm in the U.S. With over 1,000 employees, 25 offices, and $66B in sales volume since 2015, his journey is a masterclass in grit, sacrifice, and long-game leadership.💡 Topics Covered:The moment football ended—and real estate beganFrom solo agent to building a $66B empireMental vs. financial freedom as a founderWhy “ignorance is bliss” was his best advantageHiring, scaling, and leading 1,000+ peopleHis obsession with mental toughness (and Kobe Bryant)Balancing CEO life with being a father of fourThe real cost of freedom no one talks aboutWhy his last name on the company raised the stakes🔥 Notable Quotes:"When I started, I thought I was just building a small boutique. It became a monster.""If I can do it, you can do it. It’s not brilliance—it’s mental toughness.""Freedom comes at a price. You might get financial freedom, but you’ll lose mental freedom first."📲 Follow Kyle Matthews:Instagram & X: @kylematthewsceoWebsite: Matthews.comOur Sponsors:* Check out Avocado Green Mattress: https://www.avocadogreenmattress.com* Check out Indeed: https://indeed.com/FOUNDERSSTORY* Check out Kinsta: https://kinsta.com* Check out Northwest Registered Agent and use my code FOUNDERS for a great deal: https://northwestregisteredagent.com* Check out Plus500: https://plus500.com* Check out Rosetta Stone and use my code TODAY for a great deal: https://www.rosettastone.comAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
Chapter 1: Who is Kyle Matthews and what is his story?
Hey, everyone. Welcome back to Founders Story. Today, we have Kyle Matthews. And Kyle, you are the founder and CEO of Matthews Real Estate Investment Services, the largest privately held commercial real estate brokerage in the US, 25 offices, 1,000 plus agents and employees, and over 7,000 66 billion in sales volume since 2015.
I know you're going to give us some incredible tips and strategies of the success you've had, the learnings, but we got to go back in time because you have a very interesting past around a family of professional athletes. But yeah, you took a different approach. You took a different path.
So let's go back to the time when you were in college, you were playing, the possibility of you maybe being a professional before you even thought about real estate. How did this transition happen?
Yeah, no, first of all, I appreciate you having me on, Daniel. And I love how you say I took a different path. It almost makes it sound like it was a strategic choice of mine. Unfortunately, that wasn't how it all played out. I was playing football at USC about 20 years ago when We were winning a lot of games. We won national championships when I was there.
Chapter 2: How did Kyle Matthews transition from sports to real estate?
We had a great coach in Pete Carroll and some amazing teammates and players that went on to the NFL. Unfortunately, I wasn't one of those players. I didn't have that. There's levels to every game, and there's certainly levels to football, and I didn't have that last level. But it's not something you really realize early on. It was at the very end of my four years at school.
When coach sat me down heading my senior year and said, hey, we're going to go with someone younger, it kind of hits you just like a punch to the gut. And so there's somewhat a mourning of the athletic side, but really like, well, what am I going to do now? Because pretty much everyone in my family before me and subsequently after me had played in the NFL. And so I just...
erroneously made the assumption that that would happen for me. And it just, it just didn't. And so I, for a longer story for a different day, I knew I wanted to be in real estate. I liked the idea of tangible assets. I liked the idea of kind of a finance-based industry.
But I, because of the football focus, I didn't really have the technical real estate skills that most people who want to go into real estate have coming out of college. I Um, I, I didn't necessarily know how to, how to model or underwrite properties, but I wanted to be in the business.
And so, uh, very quickly, I only had a couple months to kind of, you know, accept the loss and take the L on the, on the football side before I said, look, I gotta get a job. Right. And, and I want to be in real estate, but I wasn't going to get hired for an analyst position or development associate position, a typical entry level position. opportunity.
And so really the only thing available to me, and it ended up being the biggest blessing professionally of my life, was brokerage, real estate brokerage, a service-based industry where you eventually, if you're good enough and you can communicate your value proposition to an owner, you're hired to provide services for owners when different services in the business, whether they're
buying or selling properties, leasing properties, they need debt for properties, and there's a whole host of other services. But ultimately, that's what led me into real estate was me not achieving the success I was hoping for from a football perspective.
You've scaled exponentially. I mean, these numbers are incredible. And we were talking earlier, we've had people like Ryan Serhant on here before, but the numbers that you have are just exponential in this timeframe. And- I think a lot of people look at it and say, wow, I want to achieve that one day.
And you've been doing this, or at least you started this company since 2015, which I'm sure you also had prior experiences. But what were some of the things that when you scaled from, let's say, zero to 10 million in sales, 10 to 100 million, 100 million to a billion, what were some of these transitions or some lessons that you learned?
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Chapter 3: How did Matthews Real Estate Investment Services begin?
Yeah. So, you know, what happened was I got into brokerage and I was a broker doing the deals, you know, on behalf of clients for about 10 years. And in 2015, I was presented an opportunity because of the company I was at. I had achieved success there. I think I was their top producer globally. And they were about to go public.
And so they were changing some of the internal rules around prospecting and commission sharing and all that. And again, we don't need to get in the weeds there, but it didn't make sense for me to stay. And at that time in brokerage, you... Oftentimes you evolve into what's called teams, right?
They're not formally branded, but they're teams where I was the senior agent that there were a couple of people underneath me, younger agents, you know, that were, I was mentoring, but they were also involved in my deals. I was involved in theirs. And I had a couple of employees and analysts, some marketing people.
And I was like, you know, I feel like I'm basically running my own little boutique here. I might as well just start my own thing. And that was ultimately how Matthew started. It wasn't this big plan of mine. It wasn't this, you know, well thought out vision or goal I had since I got into the business. It just it just kind of happened. And, you know, kind of silly me.
I thought it would just stay small. And then it scaled very quickly. And to answer your question. Um, it's also worth noting it was self-funded, so I have no, no outside investors, no, no LPs, no debt, like just funded it myself. And, you know, and started with 10 people, it became 20, 20 became 40, 40 became 80.
And just every year we seem to be growing exponentially lessons, you know, lessons I've learned along the way, especially as a founder of a self-funded company is it is, um, you know, ignorance is bliss. The amount of work, um, that goes into, especially the first couple of years, is I can't even prepare people for it. It's basically every waking second of every day.
I would get in the office typically at 5.45 in the morning. I'd stay till about 8.30 at night, Monday through Friday. Saturdays, I'd usually work six, seven hours on Saturdays and Sundays, I'd typically go in. And it's not just a job, it's a lifestyle. And I don't mean that in terms of like, it's this incredible lifestyle. It's a grind. And that was my experience.
And because I attached my last name to the business, it was probably the best and worst thing I ever did. You know, it was... it was the best thing that it created a lot of good, you know, brand synergy with who I was as a person. But the downside is if the business fails, then that failure is attached to my last name. And my father gave me a great last name and I wasn't going to mess it up.
And I certainly wasn't going to assign failure to it. So it just kind of created this manic obsession, this crazy work ethic that, you know, just if, if, if any other lesson from starting a company is, It's not a job. It's not something you can turn off.
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Chapter 4: What challenges did Kyle Matthews face in scaling his company?
It is basically every second of every day until you have the resources to hire professional management, you have the resources to bring on great teammates to help you operate the company, which is, you know, luckily where we are today.
You bring up something that we've heard before with other incredibly successful people like yourself that they had to be forced out to start the business. I find this common. We work somewhere. It's pretty comfortable, but we get fired. The business goes under. Things change, whatever the reason is, and then we're fired. you know, forced out to then start something on your own.
Going back to the feeling of when you transitioned, because, you know, obviously you transitioned from college thinking something and then you had to do something else. You know, you get this brokerage job, you're doing well, senior agent, and then all of a sudden everything changes and now you got to go do something on your own. Were there fears, hesitations?
What were some of those emotions thinking, okay, I'm going to start something on my own? Or were you in a place where you're like, you know what? I'm going to crush it. I have no fears. I have no hesitation.
Yeah. You know, it's interesting. I I'm, I'm happy to hear that others have had a similar start to their career where they're almost forced into it. You know, I definitely am not a victim and wasn't in that moment. I could have stayed at the company I was at as a big publicly traded brokerage company. You know, you're doing North a $10 million a year in fee. It's a very comfortable life.
And, and, and, and, Most people, it's like, why would you leave it? It's like, you don't, unless something drastic changes. And that's what happened with the going public. Again, just, just the, the, the, the relationship between my business and the company, you know, changed significantly. And, and from, from me and my teammates standpoint, it changed for the worse.
And so while it wasn't like I had to leave, I meant. from an economics perspective, it just didn't make sense to stay. And so I surveyed the landscape. I looked at other companies. I was like, they're all the same. They all have this kind of structured kind of fiefdom fee sharing thing. And I said, well, then I'll just go do my own thing.
And the answer to your question from an emotion standpoint, yeah, there was fear. I mean, fear has always been probably the biggest driver for me, less so as you get older, but certainly when you're younger, it's kind of like, Oh, what if something bad happens? What if I fail? What if it flops? So much of the fear is driven by what will people think of me?
And again, hopefully, and I've noticed this within myself, as you get older, you just care less, right? It's like the Churchill statement in your 20s, you worry about what everyone's thinking about you. In your 40s, you stop caring about what everyone's thinking about you. And then they say in your 60s, you realize they were never thinking about you. Well,
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Chapter 5: How does Kyle Matthews view the concept of freedom as a CEO?
And the cliche answer, which there's truth in it, is like, well, no, I wouldn't do anything differently because look at where I ended up. But it was certainly much harder, much more complicated. And really the word we use around here is sacrifice. There was so much more sacrifice involved. in those first couple of years than I ever could have fathomed. And I wouldn't change anything.
I wouldn't have it any other way. It's a blessing to be where I am today. Could I do it all over again, knowing what I know now? I don't know, man. I don't know. Cause like, again, ignorance is bliss. If you don't know what you're getting into, when it hits you in the face, you're just like, well, I'm already committed. Let's get to work.
That is so true. It's better to not know the future. It's really better to not know the future in the sense of that, because I'm with you. If I knew everything that was going to happen, I would have ran from entrepreneurship. I would have just kept the corporate job. I like the ignorance is bliss. I want to go back to you talking around, you know, the grind of working so many hours.
There's always this attraction to, at least on social media, there's this attraction like I want to be a business owner because I want freedom. And I always think like when I had a corporate job, I had 160 hours of vacation a year. And when I left, I was able to leave and not think about it. I almost feel like when I had a corporate job, I had more freedom. Because I wasn't stuck.
Like you're saying, like, like it's in the beginning, at least, you know, when you, when you don't have like a lot of hands, other people that are working and you can do the business, but when you're really grinding, you're like, really, you're stuck in it. You got to do it. How do you, how do you feel about this?
Where I just see a lot on social media around everyone wants to be an entrepreneur because of the word, you know, the freedom and being able to work when they want, wherever they want.
You know, you bring up such a great point, freedom. And so, uh, I'm not trying to oversimplify life, but for the sake of our 20-minute interview today, let's say that there's a mental freedom and a financial freedom. And what they're talking about is like, hey, I want financial freedom. And it's a blessing. It's a blessing to be financially independent.
It's a blessing to not have to worry about paying your bills. I think the number one cause of divorce in America, I could be wrong, is like a financial strife. And so, yeah, sure. If financial freedom is a blessing and if it's creating tremendous anxiety and stress and worry and fear in your life, You know, in my humble opinion, you should you should work towards trying to put that to bed.
But what I wasn't aware of, and this is kind of the point I think you're making, which I couldn't agree more with, is is the mental freedom you lose. And I wasn't aware of that. So it's like, hey, I want to be a founder. To your point, social media, I want I want freedom. I want freedom. And financial freedom is is a blessing.
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Chapter 6: What is the balance between financial and mental freedom in entrepreneurship?
Like when you're when you're an employee or when in my case, when you're an agent, you kind of have mental freedom where you're like, you know, you're only beholden to yourself. You're only responsible to yourself and or the clients you provide a service for. But as long as you're making more than you're spending and you feel good about your savings, that's it.
Like you kind of, you know, whether it goes up or goes down, the only person that affects is you. And there's a freedom in that. Yeah. When you start a company and whether you have five employees or, you know, my case, like let's call it a thousand people, it's not about you. It's very much not about you.
And that creates while if you know, if business is going to create financial freedom and that's great, like I touched on earlier, you don't have mental freedom and you're never disconnected from work. And when I have four young children between the ages of 14, 11, seven and three.
And so that I would say is the biggest focus I've had over the last couple of years is especially as they've grown up and they're becoming young men and women, it's to be mentally free of my work when I'm home
And respectfully, that's something I've only been able to accomplish as the revenue and the net income of the company has really scaled to hire professional management or promote within Matthews to actually help operate and run the company so that I can be present with my family and not have to be constantly tending to the business. But the first...
Daniel, the first five, six, seven years, that was not how it was. And it was, like I said, I definitely wasn't aware I signed up for that. And the financial freedom's always a blessing, but the loss of mental freedom from your work is a big, big challenge. And it's something that I wish every founder knew what they were signing up for when they start a business. I didn't know.
And I think to your point, most people don't.
A lot of the regrets that we've heard from other founders who have been doing it for many years is in the beginning, the phase of not being able to really be there for their families, spouses, like all the issues that have come along with that because they've had to put all of their energy into the business.
And I really I like I've never heard this before, but I really, really like how you said the mental freedom. Because of that, that piece of not being mentally free, you can't do everything you want to do. And you have to sometimes choose between, you know, you may be your family or you have to take a work trip or whatever that is.
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