In this episode Tim and Greg interview Tyler Chesser, a successful real estate investor and host of the Elevate podcast. Tyler shares his journey from working in corporate America to becoming a real estate entrepreneur, emphasizing the importance of personal development and mindset in achieving success.

He discusses the value of investing in oneself, surrounding oneself with successful people, and the role of coaching in personal and professional growth. Tyler also shares his perspective on the current economic climate and the importance of playing the long game in real estate investing.

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4:17 Tyler’s Transition from Employee to Entrepreneur
8:04 Learning From Challenges and Developing Mindsets
10:01 When You Realize the Potential of Real Estate

Tyler worked in marketing for a global restaurant company climbing the corporate ladder (slowly). One day he realized he was “waiting” to be promoted to the next level and needed to take more control. Success and growth depended on how well he updated his resume. He became a licensed salesperson, immersed himself in real estate, and took control of his future. These were the first steps…


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Full Transcript

Tim Lyons (00:00):

Yeah, I was working with Coach T at the time. I had to slap Coach T to have him stop talking about Tyler Chessler. You were his main guy, so No, it was all good. Alright, you fellas ready? Let’s do it.

Greg Lyons (00:15):

Welcome to the Passive Income Brothers podcast.

Tim Lyons (00:29):

Here we take the fear out of real estate investing using real life stories of everyday successful investors. Let’s go. Welcome to another episode of the Passive Income Brothers podcast. My name is Tim Lyons, and today I’m joined by two absolute rock stars, one of which being my brother Greg. Hey, doing today, buddy?

Greg Lyons (00:45):

Tim, as always. Doing great. That is for sure, and coming to you from lovely Charleston, South Carolina today. So the drab wall behind me, and if we pan out a little bit, some amazing tapestry work here. It’s all good, baby.

Tim Lyons (01:02):

So I wish I could tell the listeners that Greg’s on assignments looking at properties and walking them and stuff. No, no, no, no. Greg is now with my dad down in Charleston, South Carolina for a basketball tournament to go see one of our favorite teams growing up, the St. John’s Red Storm. So anyway,

Greg Lyons (01:21):

Yeah, when you’re a recovering college basketball coach, it just happens, right? And you need to watch games. But you know what, at the end of the day, to be able to spend time with my dad, our dad, and just kind of get out of the norm and do some fun stuff like this, this is fantastic.

Tim Lyons (01:40):

Love that. So today we have a fantastic guest and Tyler Chesser from CF Capital, and he’s also the host of a very popular show that Greg and I started listening to very early on in our journey called Elevate with Tyler Chesser. I highly recommend you folks really tune in, follow that show, give it a listen because especially Tyler, episode 173 with a guy named Tim Lyons. I mean, it was probably still in your top 10, but I want to introduce you guys to Tyler Chesser Tyler, welcome to the show,

Tyler Chesser (02:14):

Tim. Greg, thank you so much for having me. Before we go too far, I got to ask, is Rick Pitino going to bring the St. John’s? Are you guys coming back or what’s the deal?

Greg Lyons (02:26):

You guys is a relative term because I’m of course a Virginia fan. I’m tolerating St. John’s for the weekend, but I know Rick Pitino runs deep in your Kentucky roots.

Tyler Chesser (02:41):

I was just, look, it is good to see him back and it feels like, man, is this guy ever going to leave college basketball? But what? He’s passionate. So I applaud him.

Tim Lyons (02:51):

And just so Tyler, just so you know, and now the listeners know our father, rich, big, rich, as he’s affectionately known, he played basketball for St. John’s under Louis cca, 68 through 72, I believe. So growing up we had season tickets to the Red Storm. They were called the Redmond back then. So I have very fond memories for my entire childhood of going to Madison Square Garden Tuesday night, Friday night, Saturday, noon games, big East tournaments. So it was awesome. But yeah, so Tyler basketball side, you have a fantastic story. You’ve done a lot, whether it’s commercial real estate, being a broker, being an owner and operator, a capital raiser, a podcast host, a meetup coordinator, you’ve done a lot right On top of that, you’re a father, you’re passionate about personal growth and development. I mean, I really want to unpack that. So what I really love about your podcast is in the beginning, the intro to your podcast, you decode the stories, the habits, the multifaceted expertise of world-class investors and other experts in an effort to support the audience in elevating their performance and lifestyle. Now that was a lot. Now that was a lot, but you say it so passionately every single time when I hear it, I get motivated just listening to it. So what made you really dive into that personal growth and development space in your journey?

Tyler Chesser (04:17):

Well, thank you so much again for having me. And by the way, that episode two and a half years ago with you, of course, I think about it every morning the minute I wake up. And so I just want to thank you again for gracing me with your presence. But no, it’s a great question. I’ve become extremely passionate about personal development and mindset and mind expansion. The reason why is because 10 years ago I made a transition from being a corporate employee to a real estate entrepreneur and being a corporate employee, I was climbing the ladder and I was looking at the corner office and I was thinking one day I’m going to be there and I’m just going to continue to follow that long ladder and I’m going to do the things I need to do to get there. But over a few years, I started to recognize that corporate America is riddled with politicism.


And it’s really a game that in many aspects, most people who play that game end up tolerating their life. And I looked around and I said, you know what? I’m not interested in tolerating my life. I want to live an extraordinary life. And maybe it was because I was a little bit of a rebellious individual growing up, and I just wasn’t willing to accept the norm. And maybe that was just a little bit of my wiring. And as I made a transition into being a real estate entrepreneur, I realized that, man, you’re on the front lines of the emotional rollercoaster because I was eating what I killed and my results were a direct reflection of my effectiveness and my approach. And I was not used to that because as an employee, you’re really sheltered from that. And while yes, you look around and it perhaps may be a long ladder to climb to get to where you want to go, if you’re an ambitious individual, you are sheltered from the volatility, the emotional volatility of what it is like to be an entrepreneur.


And so as I kind of got more and more immersed into this world, I started to recognize the patterns of the people who are most successful, or those that invest in themselves, and they also listen and they look within and they say, what could be holding me back? What type of dialogue could be holding me back and what could propel me forward? And what I recognize is that it’s not necessarily the smartest people, it’s not necessarily the most connected people, but it’s the people who are willing to invest in themselves. It’s the people who are willing to, when they get knocked down, get back up and continue to persist forward. To me, that was exciting, invigorating, and I recognized not only from just asking other people and surrounding myself with other people who had found a certain level of success, but I started to recognize that my success was a lagging indicator of the investments that I was making in myself.


And so I’ve become so passionate about not only expanding my horizons, expanding the way that I think, and that’s why I say about mind expansion, it’s about learning, it’s about growing, it’s about, it’s about course correcting, it’s about expanding rather than contracting because there is this innate decision that we’re always making, and it’s a decision between contraction or expansion. Are we going to go backwards or are we going to expand through our challenges, through our adversity and evolve into that next version of ourselves? So I just became so passionate about that. And when I say decode, the stories and the habits, the stories are, well, what was it that allowed you to propel yourself forward? What were your own sets of challenges and adversities that you overcame? Because anybody who’s achieved any level of success has gone through challenge, has gone through failure, and they’ve received feedback through that failure, but they’ve also developed a set of habits and rituals and routines that have allowed them to persist and be consistent in a set of circumstances that have allowed them to step into exponential growth.


Because I believe that it is about the compounding nature of investing in yourself on a daily basis. And it’s not about being perfect. It’s not, hey, 365 days out of the year, I’m firing in all cylinders. It’s I’m willing to just continue to take one step in front of the next, even if I’m taking three steps backwards one day, it is about that long-term approach. So I’ve just become endlessly fascinated by it. And you know what? There’s no one exact path. If anybody, and actually I was on a podcast yesterday, somebody asked me, Hey, what are the three or five steps to, I don’t even remember what it was, but I think if anybody tells you, Hey, what are the three or five steps? They’re selling you a bill of goods, and there are no three or five steps, there are so many different pathways towards success, but there are patterns. And there, if you look back in history, there are things that rhyme and you can anticipate forward what may happen on the horizon. And I think that’s the same case when it comes to success or living an extraordinary life. So that’s why I’m so passionate about it.

Greg Lyons (09:05):

Tyler, I’m pretty sure Tim’s head is about to explode. I mean, he is riding furiously. I mean, he’s got three to five steps going right now. His head’s, he is absolutely going to explode, but that’s why we wanted to have you on because you’re so eloquently lay out. It’s an everyday thing. It’s not like three to five steps or I got to wake up early, I got to do an ice bath. It’s every day you got to keep kind of handling your business and propelling yourself forward. I’ll let Tim dive into the mindset in just a second. But when there was obviously a turning point in your corporate career, and if you kind of talk about that turning point that said, Hey, no more for me, what did that feel like? And then what have you done in the ensuing kind of decade since you made that decision to just give the listeners a little bit of background in your real estate entrepreneurship journey?

Tyler Chesser (10:01):

Yeah, so the turning point, it actually was about, it was probably two or three years of a turning point, and it was one that I almost wrestled with for a while and I was feeling a sense of dissatisfaction. And what that first manifested in was go get the resume ready and go apply for other similar jobs at other similar organizations. What my naive mind didn’t realize at the time was that I was within a larger system of other similar organizations that I was going to be running into the same type of problems being in a political type of organization and really more of a, it’s not necessarily what, but how long have you been in that seed and how long have you sort of earned that next promotion and so forth, which ultimately, in my opinion, looking back, didn’t have a lot to do with effectiveness, but more so some sort of merit that was measured in a different way.


And so it took a few years for that to really manifest into taking appropriate action. But when I finally, long story short, got into real estate, I got into real estate as an agent and I started selling houses immediately. And so I was actually, believe it or not, I started selling houses on the side. And over the course of the next six months, I doubled my income. And I said, well, that’s great. But what I also recognized was like, wow, this is an emotional game and people are making decisions on purchasing a house or selling a house based on the pink color and things like that, which didn’t really make a lot of sense to me. But when I got my foot in the door in real estate, I started to recognize, wow, this is quite a dynamic paradigm when you think about real estate.


And I never really realized this, which is crazy. I mean, of course every one of us are surrounded by real estate 24 7, 365, whether we realize it or not, whether you live in South Dakota or in midtown Manhattan, you are surrounded by real estate. It may be improved or it may not be improved. But what I didn’t realize was the labyrinth of real estate is extremely complex and there are many different facets of real estate. But when I started to recognize that it’s obviously residential or commercial real estate, and there are single family homes where people live in, of course, and that’s my primitive real estate mind at the time was real estate was a home. But what I recognized is that obviously you can generate passive income and you can generate multiple streams of revenue through income producing real estate. That’s when the light bulb started to go off for me.


And so the next step that I took was I migrated into commercial real estate and I was doing investment sales. And over the course of the next seven years, that’s really where I spent the majority of my time. But I also did start to invest on the side because I read this beautiful book, it’s called Rich Dad, poor Dad. I don’t know if any of you’re listeners have ever heard of it. I think maybe it’s sold a couple copies. When I read the book, it was interesting because I was selling apartments and I was really known as the apartment guy, and I was blessed and grateful to be able to, I’ve built a really rapidly growing business from that side of things. I built it through referrals and I made some key relationships throughout the early time of my career, which was in some aspects a blessing for sure.


But I took those opportunities and executed on them really through just hard work and through continuing to find the right information. But I started investing in apartments pretty early on the side because I recognized that these opportunities to generate real wealth were right underneath my nose. And as I started to do that, my brokerage career continued to grow. And the lifestyle of a broker, I don’t know if any of your listeners are brokers. I mean, it can be a grind. I mean, 365, 24 7, you’re always on. Even in commercial real estate, a lot of times people in commercial real estate think, well, on the weekends I don’t have to show houses and do all these things, which you don’t. But you’re still getting calls and you’re still, you’re always on. And as I started to think about what type of lifestyle I wanted to live, I started to make some strategic plans and I made a switch and we started to do some larger deals.


The first deal I did was an eight unit multifamily property. The next deal I did was 36 units. Then I started investing passively in other larger deals, and I started to recognize that there was quite an opportunity to scale. And also there were tremendous benefits to scale, and there was a level of sophistication that I needed to achieve to achieve that type of scale as well as the team and so forth. And so that was kind of my trajectory. And today we invest in large multifamily communities across the Midwest and sort of the northern part of the southeast. So that’s been my journey so far.

Tim Lyons (14:56):

Well, Tyler, I restrained myself from doing pushups in the aisle way while you were talking, so that’s going to be a win for the listeners and for the viewers on YouTube. But there’s so much I want to unpack about that, and I’m going to start with the mindset. A lot of the things you were talking about was the transactional nature of when we go to school and get a job and we start a family, and whether it’s in corporate America or you, your trading your time for money, that’s kind of what it is, right? It’s very transactional. You put something in, you get something out. And it’s amazing to me how we all go on this journey as real estate investors. It’s like a very unique kind of slice of the population that once they realize the power of building passive income, what it can mean for you.


But it is a journey, right? Because people want to start on chapter 20 when they have to start on chapter one. And a lot of the chapter one stuff is mindset and breaking through limiting beliefs. And if anybody knows, Greg and I, we grew up in a very scarcity mindset environment. I love my mom, I love my dad. They did the best thing for us. They raised us. It was all good, but it was transactional. It was spending time at your job, it was time away from the family. There was never any talk of real estate investing. I felt like it was out of touch, out of reach. That’s only what rich people did. And to sit here today as a New York City firefighter lieutenant, former ER nurse, Greg, former college basketball coach, that working in a corporate role for a car dealership doing their real estate stuff, but two guys who have built a company of Cityside capital and helped investors realize what’s out there.


I mean, it’s incredible. I mean that to me. But it didn’t come overnight, right? As many people might not know, Tyler and I shared the same coach in Trevor McGregor and we had Trevor on our show very early on because he was a huge force. You said you’re contracting or you’re expanding. And it sounds so elementary at this point to me because I’ve kind of gone down that road. But for so many people, it’s elementary, but we don’t take the time to look at ourselves to do that reflection, to do that hard work, that deep work, and do the hard yards of every day, compounding that, whether it’s a ritual or a habit or reading 10 pages a day, which is 300 a month and 330, 600 a year. I mean, how many books can you do in a year if you just started with 10 pages a day, right?


So I mean, that’s all the stuff that I feel the transference when you speak about all this stuff, because I lived it and I am living it, so is Greg. And for two guys from mine and New York, we didn’t see this type of success growing up really. And Greg and I will always kind of joke with each other after we have a good capital raise or we get paid from passive income, we always say to each other, guys from Mineola, don’t do this because of that limiting belief that we had to break through. So I just love that. The other thing was reading Rich Dad, poor Dad, a lot of real estate podcasts will start with a book and it’s Rich Dad, poor Dad, and it sounds cliche at this point, but it is the mindset. It is the foundation upon which you can build, right?


It’s not tactics. It’s not showing you how to do seller financing or vet an operator or go buy your first deal. But it’s the mindset and the shift that has to recur for you to step into that role of an investor, whether you want to be active or passive. So Tyler, I just want to shout out that you were an inspiration to me when I heard your story about that sense of dissatisfaction and taking action. Because how many people are sitting there in your car right now where you’re sitting at your desk or you’re out for a walk and you have that pit in your stomach, that sense of dissatisfaction? Man, I wish I could get involved in real estate. Man, I wish I had the guts and the gumption to go be an entrepreneur to start a new thing. Nah, I’m just going to go back to my old life.


It’s easy, it’s comfortable, but that sense of dissatisfaction is something that drives people to take that action. So you started with an eight unit, graduated to a 36 unit. I think everybody kind of knows if you’re a podcast listener, there’s something called the law, the First Deal. And whether you are a passive investor and you take that action for that first passive investment or a lot of people start off with a single family home, you start off with eight units. Can you talk a little bit about why you chose the multifamily route, which is defined as five units or more, right? Why did you go for the eight unit instead of the single family home? What were some of the benefits, especially when you were starting, try to take yourself back to that beginning point. Why did you choose that?

Tyler Chesser (20:02):

Well, when I was a commercial real estate broker, I was selling primarily multifamily real estate, but I was also selling retail office and some land. But what I was really sort of the hub for multifamily, small multifamily transactions, what I really mean is eight plus units up to probably 50, 60, 70 units. And there were times where I was selling larger properties for sure, but I just became the hub for these deals. I was doing deals off market, there were deals coming to me left and right. So buyers and sellers were transacting through me. And I love what you said about the transactional nature, and that was a big switch for me as well early on. So I just wanted to call that out, going from transactional, really transformational and building long-term relationships and having an abundance mindset with every interaction that I had to say, how can I ensure that this is a phenomenal experience?


How can I add value? But that’s a little bit of a digression. But the first decision to go into an eight unit property, I mean, it was really more so, hey, I was sourcing a tremendous amount of deals for my clients and there was a deal that I sourced that was compelling enough. And it was soon enough thereafter having sort of a realization that, hey, I need to be participating in this recipe that I’m offering to other people in the marketplace. And I learned so much from some of my really, really sharp and sophisticated clients who are really taking tremendous action in a very attractive marketplace. And I decided to kind of jump in on a deal that really made a lot of sense. But it took me, probably took me about nine or 12 months or so from really having this realization that, Hey, you know what?


I want to become an investor, a real estate investor. And there wasn’t a tremendous amount of thought behind, Hey, am I going to pursue a single family home? It made a lot of sense to me why my clients were investing in multifamily properties. You’re leveraging obviously a little bit of scale, but you’re also leveraging some of the benefits and the pros and the cons of your occupancy and vacancy and recognizing that this is more of a business and a single family home. Obviously you’ve got all your eggs in one basket with regard to revenue and so forth. And so really was never a consideration for me to go in a single family. And I’m frankly thankful that that was never a consideration because I can see why you can learn a lot of great lessons by building from one and two and three and four. But looking back, I know many investors who have come to me and said, look, I’ve done a great job of building a single family portfolio, but I want to go to the next lead because it’s bogging me down my systems, my processes don’t work. So I never really had that as a part of my consideration.

Greg Lyons (22:56):

And that’s interesting, just like Tim and I trying to start this podcast, it took us 13 months to buy microphones to figure out what we’re going to do to get a guest on and to just really get out of our own way and say, yes, this is going to add value to us. And I think a lot of people before they get into that, either first single family, first small multi, they have to get out of their way. And I think when people are listening to this, now we’re in the fourth quarter of 2023, is there a recession going to happen? The recession’s going to be happening for the last year or it’s coming now, interest rates are up, transaction volumes down. So a lot of people could say, you know what? I’m putting my pencil down. I’m not going to evaluate deals right now or anything like that.


And it is just easier to say, Hey, let me just get through the holidays, right? But there’s got to be that point where you say, I got to do something. And I think what you’re around, what you’re influenced by the five people you’re around the most, you spent a ton of time around real estate investors, and I think that rubbed off on you to say, Hey, I probably need to do what they’re doing. And when you have that, the people you’re around to say, okay, I’m going to do this now. Mindset plays a big role in it, but also the role of masterminds and coaching plays so much of a role in taking that leap. And that was a really wordy way to say, how has the masterminds being around the right people and coaching helped you go to the next level as a real estate investor?

Tyler Chesser (24:44):

So you are who you spend your time with. There’s no question about it. That’s it. Well, at the end of the day, it’s interesting because this is a hack. If you want to transform your life, it’s take inventory about who you’re spending your time with. And there are, if you really want to get into the science behind it and the psychology behind it, there are these things in our biology called mirror neurons. And what it really is for a layman is you self-regulate to become the people that you’re surrounded with. And in many aspects, it’s because of evolution. For hundreds of thousands of years, human beings have survived and propelled their genes forward by coalescing with a tribe and being with others who are going to protect them and help them survive and find food and procreate and all those things. And so you can recognize that there’s a lot of science behind this, but it’s actually interesting.


So I actually started a mastermind a few years ago, and our first retreat, we were in Costa Rica and we’ve got this beautiful villa. We were on the ocean, we had a Navy seal come and do an entire day workshop with us, and we have all these different sort of sessions. And some of these things were personal professional, but there was also a tremendous amount of hot seats where we’re talking about our business, where we’re talking about the goals that we have personally and where we’re wanting to take things. And I remember literally laying down that night thinking, man, these guys are making me, I’m like, thoughts are running through my mind that I had never thought about before. And I was the one who facilitated the mastermind, and it was like, man, these guys are really pushing me and I’m trying to level my game up so that I’m ready to be a positive influence on these guys tomorrow.


But what I sort of thought about as I was laying there is like, man, this is the self-regulation is occurring. I’m still in proximity to these individuals who are looking to live this extraordinary life and who are living an extraordinary life already. And it was just interesting to really kind of see that. But the other side is the case as well. And I know that even when I’m surrounded with people who are perhaps playing a lower game, I can recognize this and there’s a little bit of mindfulness that I have to attend to say, Hey, what type of language am I using? What type of thoughts am I having? Am I self-regulating myself back down so I don’t make these other people feel intimidated about where I’m looking to take things? And so it is interesting, but I think that we have to be conscious of it.


And there are some challenging decisions that we have to make to say, are these people that I’m spending my time with, people that I want to become more like, of course you want to inspire other people and pull their people up, but this is an important factor. And I think they say the five people that you spend the most time with, you are going to be the average of them, whether it’s with your net worth, whether it’s with your passive income, whether it’s with your health, your body mass, your muscle mass, your waist circumference, all of these things, your life, longevity, the years of your life, and all these different things. So it’s a very, very important factor that I think investors in many aspects perhaps don’t spend enough time thinking about because they’re thinking about tactics, tools, and strategies and technology and how they’re going to get that next deal, which I think are all great things. But 80% of your success in anything is your psychology, and 20% are the mechanics. And so let’s get to the root cause. Let’s surround ourselves with other people who are going to lift us up, who want to see the best for us and want to really challenge us to grow. And when you feel a little bit of discomfort when you’re around somebody who makes you feel maybe a little bit intimidated, that’s like, man, they’re playing at a higher level, that’s a pretty darn good realization and recognition that you’re spending time with the right people.

Tim Lyons (28:45):

Oh, well, Tyler, I’m going to give a shout out to coach T right there because I just heard a couple of nuggets that you just said and it brought me right back. What we do is 80% psychology, 20% mechanics. I mean, that’s part and parcel. That’s day one, right? With Coach T right there and playing at a higher level. He always talked to me about playing above the line or below the line. And just for the listeners know, coach T was, he’s a business coach, he’s a real estate coach, he’s a mindset coach. If you’re looking to break out and break through and to play at a higher level, I am so grateful that I had the opportunity to work with him for the period that I did. But listen, where are you playing? You playing above the line? Meaning are you elevating yourself to be in the room, to be maybe not the smartest guy either, to let your feelings out to be with the tribe, to try to elevate game?


And these are all things that when you’re not in this space, Tyler, it can seem intimidating, overwhelming. I don’t want to show my cars. I don’t want to tell people how much money I make. I don’t want to tell people what my dreams and my goals and my passive income number might be because I don’t even know what’s possible and how much does that guy have versus how much I have. And what I found was, and I’m pretty sure that I can speak for all of us here, is that when you surround yourself with that tribe, whether it’s a mastermind or a meetup or an accountability pod, or just maybe even listening to a podcast and jumping into it, really having that transference, you’re playing at a higher level. And if you are surrounded by five losers, well guess what? You’re going to be a loser.


If you’re surrounded by five complainers, you’re going to be a complainer. But if you’re surrounding yourself with five higher level thinking, people who want to elevate their game as being a father, as being a mother, an investor, a friend, if you’re elevating your game in the gym or having a healthy outlook on life, I mean that altogether is huge, right? And if you go to any, we’re coming towards the end of the year and everybody’s heard by now, Tyler on our podcast, but that we’re going to go to the real estate Radio Guys goals conference because I went there last year and it was phenomenal. I’m telling you, phenomenal. And I told Greg, because I don’t know if you know, but I’m cheap, but Greg is cheaper and to go to a conference or to spend money, it’s a big deal. So I already prepaid for his stuff.


I prepaid for the hotel. We just brought on a new partner at to Cityside Capital, Paul, and he’s coming too. This is all very hurtful. This is all very hurtful to me, but keep going. I love you, buddy. But to put it all together, life is like a wheel. And if you slice it up into six or eight different parts, that wheel, and you have your health and you have your fitness, and you have your money, and you have your mindset, and you have your psychology, and you have your relationships and you have your wants, goals and desires, you want that wheel to be perfectly round, filled up, filled up to the top. What section in that life is not filled up to the top for you right now? Where is that discord in your belly about? I know I should be doing this, but I’m not.


And I think this podcast and podcasts like Elevate with Tyler Chester are two tools that you can use to say, look, these are just regular guys. We all put our pants on the same in the morning. We all go, we all have these. When you’re laying in their bed in Costa Rica, you’re running the mastermind. Guys are looking to you for guidance for everything, and you’re going to bed just like everybody else saying, man, how can I serve these guys better tomorrow? I have that all the time. I have the imposter syndrome. I can’t believe that I have a podcast. I can’t believe that we have raised millions, tens of millions of dollars. I can’t believe I am where I am. But you know what? Tomorrow morning I’m back at and I got the mindset and I’m decoding all the strategies and the tools and anyway, so I just love that, Tyler, listen, can you just really quickly talk about coaching?


For me at least, I remember, I specifically remember I was on I 95 in the Bronx driving to a firehouse, and I’m listening to a podcast that Brandon Turner from BiggerPockets was on, and he was talking about how he spends upwards of a hundred thousand dollars a year on coaching and masterminds. I nearly drove off the road and just lost my stuff because I’m thinking to myself, man, why would you spend a hundred grand on coaching? That’s crazy. I would take that and I would invest it, or I would do so many other things with it. I wasn’t ready to hear it. Meanwhile, now I’ve done, well, I don’t even want to say how much I’ve done, but I’ve done that. I, I’ve done the coaching, I’ve done the masterminds, I’ve done the conferences, I’ve done those things. What value, Tyler, could you impart on someone that feels that discord in their belly and they’re thinking about man coaching, I might benefit from that. Talk to them a little bit about why the how, and maybe just give ’em some knowledge.

Tyler Chesser (33:55):

Well, look, we’re all real estate investors here. So you think about you buy an asset and you make improvements to that asset, and maybe it’s a value add, maybe it’s a reposition, and we all think about capital expenditures, right? We’re going to make a capital expenditure within our asset, which is going to change the level of income that it produces, right? It’s going to improve the level of income that it produces. And so there over time, that sort of capital expenditure has paid off over time, and there’s really no better investment that you can make than one in yourself. And that’s something that I have found to be incredibly true and impactful throughout my journey. And one that I recognize that this is a never ending journey, by the way. There are no finish lines and there’s always another level. There’s always another level to your growth and expansion.


There’s always another level to your sophistication. There’s always another level to digging a little bit deeper and peeling back the layers of the onion to understand what may be holding you back towards getting to where you want to go or what may be blocking you from thinking a little bit bigger or from getting more resourceful or digging deeper within yourself to find that extra reservoir of creativity or resourcefulness. And so coaching for me has been a huge game changer in that I’ve unlocked this individual that I didn’t really realize existed. And what I recognize is that there’s another many different layers of this individual that I don’t yet know exists. And so I want to encourage anybody who feels like they’ve made a tremendous amount of investments in themselves, whether it is through coaching or going to conferences or masterminds or surrounding themselves with great people.


And even reading books in many aspects can be a way to really invest in yourself. But coaching has been huge for me because sometimes it’s, Hey, you just need to have someone to be a little bit of a fence post for you to listen to your challenges, listen to your problems, and listen to what you believe are your impediments, but helping you think a little bit differently and see your challenges differently. When you start to see things differently, the things you look at change, and as they change and the way that you interact with them, you can start to take big leaps. And one of the things that if you find the right coach, they can help you turn decades into days. And there are many mistakes that we make along the way that can be extremely costly, especially in real estate. And of course, there’s no better teacher than failure, but there’s no better encouragement than to avoid a set of failures and to really model success and integrate other character traits of other people that you admire and take those and propel yourself forward.


So coaching is a huge thing. One of the things that I’ve become really fond of over the past few years is instead of if it is to be, it’s up to me. It is who not how. When I think about goals, you were talking about goals earlier. I think it’s 98% of Americans never set goals. They don’t set goals. And so if you want to think about, well, if you don’t have a goal, well then you’re going to end up somewhere. It’s just may not be where you think you want to end up. And so when you think about setting goals, when you look at those goals, the first question that I would ask to myself, and maybe this is years ago, is how am I going to achieve those goals? What am I going to do to get to these goals? But really the better question is, who can help me get to my goals?


And sometimes a coach can help you think about things differently. A coach can connect you to relationships who can really help you get to the outcome that you want to get to. So coaching is, it’s an extremely high passion that I have for others. I actually do a little bit of coaching on the side, and my primary business is obviously extremely busy and continues to propel itself forward, but I’m super passionate about what people can unlock through a coaching relationship, and I’m a huge proponent of it. So I’m glad you brought it up. And I think that anybody would benefit from exploring the benefits of engaging in coaching.

Greg Lyons (38:08):

So to the listeners that have been listening with us now for 30 plus minutes, they can tell that you have your stuff together. But something like that doesn’t happen overnight. It’s a journey. And in everything we do, whether it’s mindset, real estate investing or anything. And before we get to our short answers, one quick question for you, and it could be a short answer as well, but who influenced you the, because there’s so much to you, right? There’s the coaching side of things, there’s the mindset, there’s the giving of yourself to people through podcasts and masterminds, and you give a lot. Your great real estate portfolio, you give so much. So who influenced you the most in your life?

Tyler Chesser (38:55):

Well, I think Tim Ferris wrote a book called Tribe of Mentors years ago. And I think it’s really a collective tribe of people that have mentored me throughout the years and continue to, and people that I look up to even today. But as you asked that question, I was thinking of a few individuals, and one of which doesn’t even exist in today’s world. It’s a man named Ben Franklin. I read his biography many years ago, and when I read his biography, it just opened a whole new world to say, man, we don’t have to live a one dimensional life. You can actually live an extremely dynamic life. I mean, if you think about Ben Franklin, he was a scientist, he was a founding father, he was a writer, he was an entrepreneur, he was an inventor, he was a public figure, and he lived an amazing and dynamic life, but he also lived a life filled with humor.


And I just think that he left such an amazing legacy, and it was somebody that I really admired and really enjoyed reading about and learning about. So that was a huge inspiration for me. But even I think back to my corporate career, there was a superior that I had that was not my direct rapport, but he’s now one of the top individuals at that corporation. But he even taught me simple things like, man, you got to pay close attention to the way that you show up and the way that you appear. And even just things like, Hey, don’t have a wrinkly shirt, or Be careful about how your hygiene is. And not that he was calling me out, but it was little simple things like that because little things are big things. And he taught me how to be a great communicator, a great written communicator.


And I remember I was actually in international marketing, and he was the director of international, I guess the international business at the time. And we had partners across the Middle East and South America and Eastern Europe. And I was kind of the liaison between those franchisees. And I remember I would put together communications for them, but I would put together draft communications and send them to him prior to communicating. And he would redline these things. It was like I would have two words left in the communication. The whole thing else was redlined. But he would sit down with me and tell me why he redlined this and how that could be received from people from a totally different culture and background, and why it’s important to really be extremely thoughtful in the way that you communicate. And I still think about that every single day that I’m putting together an important communication.


I mean, business writing to me is one of the most important skills that any entrepreneur, investor, leader needs to really, really think deeply about. And so he was extremely impactful. But beyond that, I mean, when I got into real estate, I hired a coach immediately, and he was the guy, he was always talking about books, he was always talking about reading. He was always talking about ideas that he got from books. And he told me about this book called Think and Grow Rich. And when I read that book, I mean talk about a tribe of mentors that Napoleon Hill was decoding stories and multifaceted expertise of some of the wealthiest individuals in history. And so it was like it’s been a tribe. It’s been a collection of people that I’ve looked up to over the years. But those are a few examples.

Tim Lyons (42:13):

So Tyler, we’re going to jump into the last three questions that we ask every guest. And right now, we’re in the fourth quarter of 2023 and things are a little crazy. Real estate is in the news a lot. Interest rates. Are we in a recession? Who knows? But if you’re at a get together with people and you’re talking about real estate and someone says to you, Tyler isn’t investing in real estate too risky, what would you say to them?

Tyler Chesser (42:37):

I would say investing in real estate is a long game, and it is cyclical. It can be cyclical. And really in the modern sort of I guess, economy, we have business cycles. And of course, currently I think we are engaging in a tremendous set of volatility in the global macroeconomic landscape. And in many aspects, the capital markets are extremely volatile. And I think at the end of the day, it’s all about playing the long game and recognizing that you’ve got to be very diligent in the way that you are operating your assets and the way that you are considering the growth of your portfolio right now. I think it can be a great time to pick up some very attractive assets. There’s no question in my mind that currently real estate is in a level of downturn. So people ask about, are we in a recession?


Are we about to enter a recession? There’s no question in my mind. In real estate, there is a tremendous level of volatility and challenge that we’re facing right now. And so I think for any investor, as long as you’re playing the long game and you’re recognizing that you may have to weather some level of a storm that you may or may not be anticipating today, as long as you are positioned to do so for the long haul, you’re going to be successful. And the game that was played over the past couple of years is no longer the same game that we’re playing today. And it’s not about timing the market, but it is about time in the market, and it is about a long-term approach and a long-term strategy towards capturing opportunities and operating your assets. So I think these are some important things for investors to consider today or even during the next expansion.

Greg Lyons (44:20):

That’s a really good one. Time in the market. That’s a great nugget right there. Our second thought is from Jim Rohn and he said, formal education will make you a living self-education will make you a fortune. What does that mean to you?

Tyler Chesser (44:39):

I mean, it’s 100% true. I am a big believer. So actually I’ve read a book and actually maybe many of your listeners have read this book. It is called The Changing World Order by Ray Dalio. And he talks about sort of the big cycles in history and some of the big cycles that we’re perhaps within right now. And in many aspects, we’re talking about economics and in geopolitics and so forth. But I think there is a correlation between what causes nations to rise and fall, and also similarly in your personal life or in your family life. And one of the things factors that Rad Allo studied was as nations invested in education, for example, their future rose, and education is not the same thing as learning. It’s not the same thing just to go to higher education, go to get another degree, that doesn’t mean you learned anything.


So the question is, what are you learning? How are you growing? How are you expanding? So self-education, in my opinion, has been one of the, if not the most impactful things in my life. I went to college and I got a degree in all these things, and there’s certainly things that I lean on in terms of things that I learned and things that I took away, but it’s about developing a discipline and a lifestyle around continual learning, continual expansion. So for me, self-education has been a big, big game changer in the way that not only I deal with challenges and issues today, but I think bigger. And I start to think about what else could be possible. What else? It’s like the more I learn, the more I realize I don’t know. And that’s why I’ve become so obsessed with reading and listening to great podcasts like this, because there’s always something new to learn. Even if it’s someone that you perceive may not know as much about something that you do, there’s still always something to learn. So I think there’s a level of humility that you gain through self-education and continued expansion, continued growth, and continued learning. So I love that quote, and it’s something that I’ve really lived myself by or my life by.

Tim Lyons (46:50):

Love it. I couldn’t agree more. So that brings us to number three and the third one, I think in this current economic climate with interest rates where they are and inflation talk and dominating headlines, Robert Kiyosaki can rub people the wrong way sometimes. He’s a little bit in your face, I guess, but he says something that goes like this. He says, savers are losers and debtors are winners. And to the uninitiated, that can sound a little bit crass or a little bit crazy. So what does that quote mean to you?

Tyler Chesser (47:26):

Well, I think in many aspects you have to, what he’s referring to is essentially the currency devaluation over time. And if you look at the behavior of governments around the world, especially over the past few years, I think this quote is extremely relevant because when Covid hit, I think the US government printed about $4 trillion. And over the past three or three and a half years, our national debt went from 22 or 20 trillion to 33 trillion and growing by about 500 billion a month at this point in time. And when you think about numbers like that, in many aspects, it’s hard to wrap your mind around 1 billion, much less $1 trillion. And so what we’re talking about is the expansion of the money supply, which essentially means every single dollar in circulation is less and less valuable. And when you think about even interest rates today, let’s say that you buy a new deal and it’s around six point a half or 7%, that’s probably lower than the rate of inflation.


Even though this past week we saw ACPI print, which in many aspects in my opinion, but I think there’s more than an opinion here, if you really dig down to the numbers is manipulated in itself. So inflation essentially, if you were to make it simple, it’s really the value of your dollar is diminishing on a day-to-day basis. But the other side of this coin, and I think Robert Kiyosaki would agree to this, even though he is gotten a little bit curmudgeony in his later years, I think he would agree that cash is also king in times of challenge. And so if you don’t have the adequate cash reserves to be able to capture opportunities, you’re going to be in a challenging circumstance. And so if you’re in a downturn, the folks who have the capital to pick up opportunities are the ones who are really going to be very, very happy on the back end of this.


So there’s a little bit of a balance to think about, but if you utilize debt and you utilize leverage appropriately, and it can be a double-edged sword, it can be very challenging, it’d be very dangerous. And we have seen, and we are seeing in some aspects across the landscape, foreclosures and so forth. So you got to be very careful about the way that you’re capitalizing your deals. But if the cost of that capital is less than the inflation rate, then you’re playing this game in the wise way. But if you’re saving, if you’re only saving that capital, even if you’re earning, let’s call it 5% in a money market account or in a treasury, really, you’ve got obviously taxes and so forth, but your purchasing power is diminishing as a result of the behavior of central governments across the world.

Tim Lyons (50:13):

Well, I knew where I was going to get a very thoughtful response to those questions from Tyler, so I appreciate you taking the time and kind of diving into those questions with us. But yeah, I mean, Robert, it’s where a lot of people start, and if you don’t understand some of the stuff like right now about inflation and stuff like that, it’s okay, I didn’t learn this stuff overnight either, but you got to start somewhere, and as an investor, no one’s coming to save us, right? You have to kind of really lean into the process about education and then taking that action. So Tyler, this has been awesome. I feel I could talk to you for a couple hours, but we have to come to a close. If people want to find out more about your podcast or your company, CF Capital, what you guys are working on, they want to connect with you for coaching. What is the best way for people to do that?

Tyler Chesser (51:02):

Yeah, so just go check out Elevate Podcasts on anywhere you listen to podcasts. If you’re listening to this podcast, you probably can find us on the exact same platform that you’re listening to, whether it’s Apple, Spotify, you name it. So you can check us out there at Elevate Podcast, of course. Also, the website there is elevate if you want to learn more about the history there. We’ve been doing that podcast for over four and a half years, and it’s been an amazing journey so far. Also, if you want to learn more about CF Capital and what we’re doing and you want to learn more about potentially partnering with us on future acquisitions, just go to cf cap We focus on large multifamily real estate across the Midwest and the northern part of the southeast. So always are really building relationships with investors and abundantly minded investors who are looking to make a positive impact on residents, positive impact on staff, and are looking to be a part of a community and a tribe who are elevating their lifestyle, elevating sort of everything that they’re doing. So invite you to go check us out there at, and if you want to learn more about me personally or what else I offer, just go to tyler So those are a few places where you can find me, but I am also across social media. I try to be as active as possible, but I got to tell you, it is a lot to keep up on social media these days. So I do my very best. But appreciate you guys again, having me. This has been a lot of fun.

Tim Lyons (52:27):

Awesome, man. Well, I’m grateful for the opportunity to have you on. That’s going to do it for this week’s edition of The Passive Income Brothers podcast, and we look forward to serving you again next week. Thank you for listening to another episode of The Passive Income Brothers podcast. We would be grateful for your support of our podcast by giving our show a five star rating and review and subscribing to our show on your favorite podcast platform. Don’t forget to take inspired action after listening to this show so that you can start building out your passive income streams. Finally, head on over to cityside to connect with us and find out more information about how to get started passively investing in real estate.