Founder's Story - From Rejected Athlete to $66B CEO – Kyle Matthews | Ep. 197

Episode Date: April 8, 2025

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 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

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Starts tomorrow at Macy's. Savings off already reduced prices. Exclusions apply. Hey everyone, welcome back to Founder's Story. Today we have Kyle Matthews. 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, 1000 plus agents and employees, and over $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, I 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, won national championships when I was there. 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. And so, 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's like 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, you know, erroneously made the assumption that that would happen for me

and 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 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 didn't go to real estate finance classes. I didn't necessarily know how to model or underwrite properties, but I wanted to be in the business. And so very quickly, I only had a couple months to kind of accept the loss and take the L on the football side before I said, look, I got to get a job, right? 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 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, you know,

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 Serhan 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 in the, you know, when you scaled from, let's say zero to 10 million in sales, 10 to a hundred million, a hundred million to a billion, what were some of these transitions or some lessons that you learned?

Yeah. So, you know, what happened was I got into brokerage and I was a broker doing the deals 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, 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, in, in brokerage, uh, 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, 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 well-thought out vision or goal I had since I got into the business. It just kind of happened and kind of silly me. I thought it would just stay small and then it scaled very quickly. And to answer your question. It's also worth noting it was self-funded. So I have no outside investors, 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, you know, ignorance is bliss. The amount of work that goes into, especially the first couple of years is, I can't even prepare people for it. You know, 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 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 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 this best and worst thing I ever 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 failures attached to my last name and my father gave me a great last name and I wasn't gonna mess it up And I certainly wasn't gonna 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, it's not a job, it's not something you can turn off. It is basically every second of every day until you, 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, like we work somewhere, it's pretty comfortable, but you know, we get fired, the business goes under, things change, whatever the reason is. And then we're, you know, forced out to then start something on your own, going back to the feeling of when you transition, because it's, you know, obviously you transition from college thinking something, and then you had to do

something else. You know, you, 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'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 of $10 million a year in fee. It's a very comfortable life. 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 the relationship between my business and the company, you know, changed significantly. And from me and my teammate 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, you know, oh, what if something bad happens? What if I fail? What if it flops? Like, you know, 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 everyone that's thinking about you, and then they say in your 60s, you realize they were never thinking about you. Well, my fear was driven like, well, if I start this and I fail, oh my gosh, what are people gonna think?

And getting back to the last name, I don't wanna be seen as a failure. On the other side, I think probably the biggest thing I had going for me, Daniel, just candidly is ignorance is bliss. I just, I was very naive to how hard it would be. I was very naive because I said, well, you know, I'm in brokerage. I'm doing great. I mean, clearly I figured out I'm 32 years old. I have all this money. Let's go do it. And it's just, there's so much more to operating a business versus just like providing a service.

And people always ask, knowing what you know now, would you do anything differently? 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

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 a corporate job. I like the ignorance is bliss. I wanna go back to you were 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 wanna 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 any, I almost feel like 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 in the beginning at least you know 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, you know, I, 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 that's, 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, in my humble opinion, 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 the mental freedom you lose. And I wasn't aware of that.

So it's like, hey, I wanna be be a founder to your point, social media. I want, I want freedom. I want freedom. And financial freedom is, is a blessing, but what you give up for financial freedom, certainly for a period of years, let's call it for me, you know, it's we're roughly a decade in is the mental freedom from your work. And I can't necessarily represent that I've, I've lived another life and I've been in a, what I'll call a traditional job, but you're absolutely right.

When you're an employee or in my case, when you're an agent, you kind of have mental freedom where 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. Whether it goes up or goes down, the only person it affects is you and there's 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.

When you start a company and whether you have five employees or, you know, in 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 good, it creates 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, 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, first five, six, seven years, that was not how it was. with my family and not have to be constantly tending to the business. But the first, Daniel, first five, six, seven years, that was not how it was. And it was, like I said, it was, I definitely wasn't aware I signed up for that.

And the financial freedoms, always a blessing, but the mental, 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 we know whatever that is I I it'd be great to understand your development as a person Going from those early stages or the first five to seven years To now, you know transitioning to the CEO of all of these people, and how have you personally changed along as it's progressed further to closer to now? Yeah, I would say the biggest development in me as a person and a CEO, and those are so intertwined,

it's the same thing. I'm not a different person at home than I am here in terms of the foundational values and characteristics is I would say when I was, you know, I'm 42 now. So when I was 32 and I started Matthews, I had such conviction and certainty about almost everything in life, whether it was parenting or business. And there comes so much inherent judgment in that. I was so judgmental, like this is how it's done. And this is the way, and this is so judgmental, like this is how it's done and this is the way and this is the right way and this is wrong and these people wrong and I'm right

and look at my track record and look at my results and that's why you should follow me. And there's pluses and minuses. So as I've gotten older, I've become less judgmental and because I'm less certain, I'm like, well, I feel very strongly and my experience taught me this, but maybe there is a different way. Maybe there is a, I won't say a better way, but another way that it's not

necessarily everything in life is a one size fits all, whether that's personal or professional, the value of being certain. And again, not necessarily judgmental, but the judge, the judgment part comes with the certainty that you're right. At 32 years old is that you're right at 32 years old, is that you have tremendous conviction. And if people actually buy into what you're teaching, coaching, or leading them towards, you could be very, very effective.

And I say this as humbly as possible, I'd like to think for a new CEO in 2015, roughly 10 years ago, 32 years old, I was very effective as evidenced by the, you know, by the results. And, but I was certain that I was right and there was one way and it was the way I was doing it. As I've, as you, you're just, as you're on this earth longer, whether it's as a business person, as a parent, anything, a teacher, a student,

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Don't miss out. Get started for free today from a parenting. You're like, oh, OK, now I know why my parents did this or now I know why I shouldn't do that. You just you start to become exposed to more, more strategies, more paths to success, more ideas. And the biggest to answer your question, the biggest change in me is I'm much more willing to consider a different path. Now I still have very strong opinions and the guys and gals here would say, well, yeah, that's funny Kyle says that because he's still very opinion, very strong opinions. But I would say if I can be accurate in my own self-assessment, which is very hard to

do at times, is I'm much more open to hearing a different idea. Again, I'll still make the decision than I was maybe 10 years ago. I was like, nope, this is the way and I'm right and this is what we're going to do. Well, only because I was lucky enough to be born in my family, I've met so many of these athletes. And so I got to pick the one I never got to meet. And, and I was, and still I'm the biggest fan of this person. And it's, it's a shame. I'll never get a chance to meet him.

Kobe Bryant. Um, there's so many amazing lessons to be learned by watching his life and his career. Uh, but so much of what, who I am as a person, let alone how I operate this company, uh, is really operate this company, uh, is really a mindset mentality, uh, you know, foundation of mindset mentality. In fact, I have a podcast, the Matthews mentality, where I sit down with high achievers across all industries and yeah, I have them tell my, tell their story

arc and where are you from and how'd you get in the business? But really I say, what, what are your motivations? What drive you? What is your why? And how has that changed? Cause I find that fascinating about myself, how my motivation and my why has evolved over the years. And really a lot of my perspective and my curiosity

about mentalities, mindsets, and really the drive, like what drives people to be great? You know, that 1% and why does the other 99% have it to that degree? I don't know the answer to the question, but I'm certainly exploring it is because of Kobe Bryant And I spent a lot of my time growing up in Los Angeles I had the privilege of being a fan of the Lakers still am

and so he brought a lot of joy to my life in terms of winning championships like you know, but I Just I I am fascinated and I find who he was so remarkable From a mental toughness and and that is one of the most attractive qualities I find in people whether it's in my wife what I hope my kids, you know that we're working on that But with my teammates here is I love I love skills. I love intelligence I love emotional intelligence But more than anything I love mental toughness because it's anything, I love mental toughness, because it's my humble opinion that mental toughness in yourself and or your teammates

will see you through almost anything professionally life's gonna throw at you. And personally too, but I'm gonna talk professional here, whether it's a recession, whether it's a bad quarter, whether it's a bad product or something's not working. If you're mentally tough, you're gonna find a way to push through it and keep working and not give up. Most people in real estate who fail,

they don't fail because they don't have the acuity, they're not smart enough, they're not even emotionally, that's not it, it's just because they're not mentally tough enough. And when it gets hard over a long enough period of time, they give up. And the reason I'd wanna meet Kobe Bryant, to your question, and spend time with him,

is just like, I've found I'm most inspired when I'm the least motivated person in the room. And you know, that's hard to do. I'm very motivated. I'm very driven. I think my reputation within my industry, you know, kind of perceives me in terms of my work ethic. And I, you know, the culture of the company is a shadow of the CEO.

Like the work ethic of Matthews is, is, is hardcore. Right. And, but it, it's really, you know, a lot of it being inspired by Kobe Bryant and the way he approached his career, you know, that would be it. Kobe for sure on the athlete side. And again, part of it is I've had the opportunity to hang out with a lot of the best football players

and I love them all, but yeah, it would be Kobe for me. From a professional standpoint, it's such a cliche answer. And I have to provide a disclaimer. This is not meant in a political sense. So it's Elon Musk. I think what the guy, just from a professional standpoint, what he's been able to achieve,

obviously the PayPal thing was great and he had incredible teammates there. And you know, so many of them, Reid Hoffman or Peter Thiel or, you know, David Sacks, but how in the world does a guy build a car company from scratch? He builds a rocket, you know, SpaceX from scratch. Like it's insane. Like how does he, how does he do it? You know, how does he, how does he find the time? You know, does he sleep? But, but really is he just naturally gifted? I'd love to hear how he's evolved as a leader in the time and maybe what perspective or

what he'd do differently. But again, putting what he's working on aside right now, it's fascinating and I'd love to just spend time with the guy. I got one job here and it's a company, okay, there's a thousand people it's big and but like man It takes so much and every every night I'm crawling to bed, right that and the four kids I could exhaust you But how in the world does he do he does it? You know, he the companies are bigger certainly more public I mean he has a gas tank. He has a resolve you get back to mental toughness, that guy, at least right now, is showing he's mentally tougher than I ever could be.

I don't even know how he's dealing with what he's dealing with right now, but it would definitely be Elon. Thank you for sharing that. I really love both answers. I could totally relate to those things. We got to spend a day with Gary Vee and from an energy perspective, that guy has more energy than anyone I've ever experienced in my life. I don't even know how he does it, man. That guy goes 24-7 at 100 miles a second. And I was really, really amazed at all the things I learned that day.

I just could not believe how much energy. I was tired. Some people are just built different and those guys are built different and getting back to, you know, kind of how I've changed over the years, like when I was, you know, 10, 15 years ago, I don't wanna say a hater, but I'd be like, well, you know, I could do that or I could do this. And now I'm just like, nah, that guy,

he's just a savage or that gal, like, she's just, she's just, you know, she's smarter than me, she better me. As you get older, and I think part of it professionally, you get comfortable with what you've accomplished, it's so much easier to give people their flowers and say, no, that person is just like that. I look up to that person,

and every day I look up to more and more people because as I gain perspective in life as a CEO, as a father, as a husband, and as a friend, I just realize how much harder it is and how much more complicated everything in life is than maybe I thought, you know, when I was 22 coming out of college and had it all figured out. And so, you know, again, looking at what Kobe was able to accomplish or Elon, and there really are a lot of examples, but those two stand out as it relates to your question.

It's such a, it's incredible. And it's a privilege to have been able to learn from both of them. Even if it's from afar, from arm's length, I haven't had the opportunity to meet either of them. But yeah, just both of those people I look up to tremendously. Yeah. Thank you for sharing that, by the way. This has been really great. We could probably talk for another hour. I have tons more questions, so you got to come back and then we can dive into whatever whatever has been changing I mean the real estate industry. I am very fascinated with it. We got it We have to do a whole show that's even talking about the state of things I'm curious about that. But if people want to get in touch with you Kyle, how can they do so?

Yeah, you could look I have social media. This is something I just started a year or two ago So speaking of Sarah, I got to get on he's looking up to him and he is the best He's the best from a branding and marketing. So credit to Serhan. I got to, I have to step up my game, but on X, I always want to call it Twitter. On X, on Instagram, it's at Kyle Matthews, CEO. You could DM me and I do the best I can to respond to him in a certain amount of time. Obviously LinkedIn, just look up Kyle Matthews,

the website Matthews.com if you have anything commercial real estate from a service need. We're in pretty much every market, definitely all the larger ones. And so, yeah, have Ryan and I back to talk all things, real estate, he's on the residential side, I'm on the commercial side. And to your point, that's an hour long conversation

with what's going on with rates, supply and demand, follow the jobs. Like there's so much into real estate that I'd love to talk about, but that's a, that's a longer conversation for a different day. I would like to, we're looking at doing more round table discussions. So I'm going to make that happen. Make it happen. Jack, and we'll do it in person because I think that would be even, uh, that'll be even more interesting. But Kyle, thank you so much. This has been great.

I learned a lot. I got a lot of great sound bites that I want to share with other people. And I'm always appreciative because our mission is to impact 100 million people here at Founder's Story. So the more that we can share your story and amplify that, I know people are gonna be inspired.

So thank you so much. And we're honored to have you on today. I'm honored to be here, Daniel. I can't thank you enough. Thank the audience for listening. And my one last thing is, and I tell people here all the time, if I can do it, you can do it. I don't have a unique skill. I don't consider myself that smarter. Emotional intelligence is okay. It's just, it's hard work, mental toughness and just pushing through. So if you're thinking about starting a business, just go for it, man. You know, fear is not the reason not to do something. Are you looking for legit ways to make extra money? Our friends

at the side hustle show have put together this cool free 60 second quiz to help you do just that. All you got to do is go to hustle that show. You can do it right from your phone, answer a few short multiple choice questions questions and it'll recommend a few episodes of the hit side hustle show podcast to start with. You can add your personalized side hustle show playlist to your device, learn what works and start making more money today. Again, that's at hustle dot show or follow the

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