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5 Real Estate Freedoms with Tyler Chesser

5 Real Estate Freedoms with Tyler Chesser
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Dave Debeau [00:00:09] Well, here again, everyone, this is Dave Debeau here with another episode of the Property Profits Real Estate podcast today. Zoom in here with us and a good looking guy, Tyler Chesser. How are you doing today, Tyler?

Tyler Chesser [00:00:20] Dave, so I will send you the ten dollars. You said I was good looking. We'll send it to you right immediately. But, my friend, it is great to be with you. Thank you so much for having me.

Dave Debeau [00:00:28] It's my pleasure. Tyler, tell us where you're zooming in from this fine day.

Tyler Chesser [00:00:32] I am zooming in from Louisville, Kentucky, in the United States. And I mean, it's it's summertime. It's it's great here. But how about you? How's your day going so far?

Dave Debeau [00:00:42] Life is lovely in the loops. It always is. Summer is here. It's bright. Sunny, I'm take a look out at Mount Rabson as we speak, and it's always a nice day. So, yeah. So, Tyler, tell us a little bit for that. For the listeners that aren't familiar with you yet, a little bit about your real estate investing claim to fame. What is it that you focus on primarily? What do you do these days when it comes to real estate investing?

Tyler Chesser [00:01:06] Yeah, I focus on multifamily investing and we'll talk a little bit about my background, I would imagine. But as I kind of ramped up through the commercial real estate ranks, I found multifamily to be the perfect asset class, not only for where I wanted to grow through and the risk reward balance and all of the different sort of occupying risks and all the different things that we love about multifamily. I found it to be the perfect asset class. So we focus on not only syndications, but I also focus on investing actively and passively as a multifamily investor. So that's what I focus on in real estate these days.

Dave Debeau [00:01:43] Very cool. And how long have you been doing that for?

Tyler Chesser [00:01:46] I got into real estate in twenty thirteen and I got into the business as an agent and grew through the ranks, became a broker and built a brokerage company along that time frame, I actually was investing actively in smaller and mid-sized multifamily deals. And so I've been investing in multifamily since twenty fifteen.

Dave Debeau [00:02:06] All right, very, very cool. So, Tyler, you didn't start off your young looking guy, but you didn't start off doing real estate investing, what was what did life look like before you got into real estate? What were you up to?

Tyler Chesser [00:02:18] Yeah, I was in the corporate world. I was in corporate America. And maybe many of the listeners have had that sort of background. It was interesting because I never had any sort of understanding that I would do anything other than climb the corporate ladder, because that's what I was always taught to do, is to go to school, get good grades and get a good job. And that's the path that I took myself on. And I kind of grew up in a middle class lifestyle. And it wasn't that we weren't able to pay our bills, but we weren't overwhelmingly abundant from a financial resource capacity, at least from my own background growing up. But I got into corporate America as an international marketing specialist, and I was actually growing in a corporate career for a global restaurant brand. And we were actually launching restaurants across the world in new locations. And I found it to be very intriguing and very stimulating intellectually. But what I but I did not find intellectually stimulating was the politics of the corporate grind. Right.

Dave Debeau [00:03:13] There was going to ask you it sounds like it was pretty good. So why why did you decide to get out of it? But yeah,

Tyler Chesser [00:03:19] yeah, yeah. I've always been fascinated with consumer behavior and, you know, really just behavior in general around branding. And so I found it to be really exciting and interesting to launch a brand in new cultures and different cultures across the world and how that was received. But the politics of the corporate life were really tough. I wanted to grow and I kind of visualize myself in that corner office or in the C suite. And as I spent more and more time in corporate America, what I learned was it wasn't necessarily about effectiveness, but it was more so about time in the saddle. And perhaps, you know, who do you know who likes you and who really wants you to get to that to that corner office. And so I found that to be a little bit causing a little bit of dissonance, so to speak, in my life. And after I looked around and I said, well, wait a minute, do I want to wait 20 years or 30 years just to wait 20 or 30 years? You know, I kind of answer that question. No, but it was interesting. The first inclination that I had was let's get this resume ready and maybe another organization will allow me to climb that ladder quickly. What I realized was that I was climbing the wrong ladder. Right. That ladder was the same, you know, same climb in different organizations and perhaps it would look a little bit different. And so I was asking myself, well, what else could there be? Right. Because I went to school, I went to college and I got a degree for this particular profession. And when I started climbing that letter, I said, well, wait a minute, let's go somewhere else. And so I started asking questions. Right. I started asking myself and I had to go through pain for a few years before I actually made any progress. But then I started asking questions and I came across real estate because I had bought a home several years prior to this in my realtor said, hey, you should come to this seminar that our company is putting on to learn if real estate might be a fit for you. And at that time, you know, I'm a marketing guy, right? When I think of real estate, the first thing that comes to mind is a single family home. And that's all I knew about real estate. And so that was my entrance into the door. I took a personality assessment and it said, hey, you might make six figures if you become a real estate agent. And so I said, wow, that's amazing, let's do it. And so I get into real estate and the rest is history. But there's many other steps that I took from there, but that's how I entered into this world.

Dave Debeau [00:05:30] OK, so you were you jumped in as a realtor first and then started investing, is that correct?

Tyler Chesser [00:05:37] That's correct, yeah, yeah, I got my license and started building a business based on referrals and based on one deal at a time, over the course of six months, I was being I was an agent and I was actually selling homes on the side. I was actually still working in my corporate job and I doubled my income in six months. And I'm like, wow, this is really, really interesting. But what I learned was that, wow, I don't really love the residential real estate game because it was very emotional and there was a lot involved with, hey, I don't know about this pink color. And it took me a little while to kind of get my my footing underneath me. And once I realized, well, wait a minute, it's not about emotions. And there's so many other things out here in real estate. And by the way, this guy named Robert Kiyosaki, he taught me how the rich really think about money. And it wasn't about trading more time for more money or more expertize, but also using assets to create more income and to create more opportunities and more options. So that was a new paradigm for me. But I continued to step over more and more paradigms as I got more familiar. But then I became involved as a commercial real estate broker, a full time commercial real estate broker, and never look back.

Dave Debeau [00:06:43] All right, so there are a ton of realtors out there that know not to bash your profession, but I will anyhow. There are realtors out there who don't even own a home they live in, much less investment properties. So there's a big, big, big difference between being a real estate agent and a real estate investor and active real estate investor yourself. How did you make that leap? He gave me a hint there that he is acting as part of that. But, you know, there's a big difference between reading the book and then buying your first property. So how did that happen for you? When the things that you had to kind of overcome to make that happen?

Tyler Chesser [00:07:23] Yeah. So when I got into the business, you know, it was really I mentioned it was almost like a paradigm shift after paradigm shift. The first thing that I did was my original broker who I worked under recommended that I hire a coach and I hire this coach and he teaches me all about building a business based on referrals. And the interesting thing about it was I learned so much more about communication. I learned so much more about mindset. I learned so much more about working on the business versus in the business and all these different things. And it was a transformation from being an employee to being an entrepreneur and really an investor and investing in myself and investing in the business. So that was one of the first leaps that I had to make. And he kept talking about books. He kept talking about thinking grow rich. You kept talking about how to win friends and influence people. And some of these things, they sounded silly. They almost sounded foreign to me. And I remember he was talking about thinking, grow rich. I'm like, all right, let me check that book out. And I read that book. And man, I was cross-eyed. I almost couldn't figure out half of the things he was talking about, but it caused me to start thinking, like, you know, is what he's talking about. Is this really possible or is it really possible for me to think and create a larger future? And so that was a huge paradigm shift. But for me, as long as I grew my business and as long as I learned more about what it really takes to be successful in this business, I started to open my mind to new possibilities. And I was selling multifamily real estate as well as retail, real estate office, real estate. And I learned that investors look at real estate much different than consumers do. Right. And so that was almost my first eye opening situation, was I realized the way that people view the world obviously transforms the way you interact with your world. And so that was the first thing was learning. Well, what's the how do people look at these deals and how do they capitalize on opportunities and how do they say yes or no to a certain opportunity? How do they negotiate that deal? How do they manage the due diligence? How do they maximize that profitability of that property? And how do they look at it from a creative lens? And so I learned so much through this process. But what I did was when Robert Kissack taught me how the rich look at money and wealth and really their their paradigm on the world, I started to say, well, wait a minute, why can't that be me? Right. Why can't I take action in this capacity? So the first deal I ever bought was an eight unit property. And I remember I'm like, man, I am I'm an expert. I sell these things all the time. I was selling fifty unit properties, sell selling seventy five unit properties and so forth. And I'm like, you know what, I can buy an eight unit. Right. I can do that. That's no problem. And I'll tell you what, it's so interesting as an agent or as a broker at the closing table, you shake hands and you walk away and you say congratulations, you know, let's keep in touch and I'd love to serve you in the future. But as an investor at the closing table, that's Daisy, right? The real work begins then. So I learned really so much during that first deal, in those first few deals, as I continue to grow and as I continue to really put my commissions to work and put those into opportunities to, you know, help that grow and help my own resourcefulness grow in terms of my cash flow, because all of my income was determined by my efforts up until that point in time. And so I was developing then a system through real estate, which could serve me to a greater capacity. But it really all started with my belief that it would be possible. And the understanding that, hey, you know what? You don't have to just think in this middle class capacity because there's so many people out there that you have never really realized that real estate can give you so many more options. So that was really my first step. But then it was taking action and letting the process unfold as I went through.

Dave Debeau [00:10:57] Very cool. Very cool. So a few days ago, I had a nice chat with our mutual friend, Mr. Trevor McGregor, who I think you know very, very well. So at what point did you start working with Trevor? Did you bring on board as as your coach as well? Why did you decide to take that step? And then more importantly, what did that help you to accomplish?

Tyler Chesser [00:11:20] Yeah, no, it's so good. And I'm so fond of this because Trevor and I have become great friends. We've become business associates and and partners on deals and so forth. But I hired Trevor in twenty eighteen. I had been growing my commercial real estate brokerage business. I had invested in millions of dollars worth of real estate, but I was ready to take it to the next level because I had. Systematized some things in my business, but I was almost feeling like I was drowning in success is kind of ridiculous as that sounds. I was making a lot of money being a commercial real estate broker, but I was always in demand and I didn't feel like I could break free from that. I almost felt like it was pulling me down and it was limiting me from going to the next step. And, you know, it's so interesting because I had multiple clients in different markets across the United States that had hired this guy named Trevor McGregor. And they were killing it. They were crushing it. They were buying properties all over the place. They were scaling. And it seemed like they were living the life that I wanted to live as well. So I really admired these people. And it's so interesting because one was in New York and the other was in Minneapolis. And I noticed there were similarities. Right. So what's the common element here? And it was this high profile, high performance coach in Trevor McGregor. And so I reached out to Trevor and identified an opportunity to hire him and to bring him into my corner so that I could really expand and scale in this business. Because what I learned was that the more and more that I invested in real estate, it was about scaling. Right. Because you can learn and you can make mistakes on a smaller scale. But as you buy larger properties, you have the economies of scale where you can put a great team in place. And there's so many different benefits to scaling. But you have to do it right. You have to do it in a smart way. And so the way when I started working with Trevor, what we were able to do is we were able to really identify where my blind spots and where my limiting beliefs, because really going back to some of these early clues, it all starts within your mind. It all starts within your beliefs. And what was my perspective was really what would be possible. So that was really kind of the beginning parts. But happy to go in on any details.

Dave Debeau [00:13:28] Well, yeah. So what were some of the roadblocks? Let's say just pick one, because we take the time here. But what would be the biggest roadblock that that helped you move over, move through?

Tyler Chesser [00:13:41] I think the biggest roadblock for me was trying to write. So I looked at the brokerage business and said, all right, well, I'm doing really well here. You know, I could continue to do really well here and continue to grow here. But at the same time, there was something within me that said this may not be the lifestyle that I want over the next 30, 40, 50 years because I'm a young guy, as you mentioned, I'm still early on in my career and hopefully I'll have a long time ahead of me to continue to grow. But what I learned with Trevor is that there's so much more out there, there's so much more available to me if I give myself permission to do so. And so not only through real estate, not only through real estate investing, but also through podcasting, through coaching, through mentoring, through being a keynote speaker across the country and really internationally as well. And so it opened my mind to so much more impact than just impacting one person on a one to one basis. Now, I could scale my expertize, I could scale my passion. So, you know, I have launched a top two hundred business podcast globally called Elevate, where we've had people like Seth Godin, Dave Astbury, John Assaraf. We've had some of the world's top experts in the entire planet discussed mindset, mind

Dave Debeau [00:14:50] expansion on there.

Tyler Chesser [00:14:51] Yeah, I know. Well, you're going to be on there very soon. I know we're going to talk about that. And, you know, what I've learned is that there's so much more available if we give ourselves permission to do so. And so, you know, there's so many different things that we've gone into in terms of developing systems, strategies, understanding how to maximize your time management, understanding how to be the master of not only your mindset, but helping other people break free of those limiting beliefs as well. And when you surround yourself with all these things, it's almost a compound effect. And the exponential growth that I've experienced as a result has been profound in my life has completely changed. Like you and I are sitting here right now, I'm not worried about where where's the next paycheck coming from. Right. There are systems that are supporting this continued growth so that I can be completely present with you. So there's so many different benefits. But these are just some of the high level

Dave Debeau [00:15:43] that I'd like to share with you some time. So I'm I'm very pleased to say that at the time people are are watching this podcast episode next week on June the twenty third Wednesday, June the twenty third, you and Trevor are going to be hosting a master class called Elevate Your Real Estate Game. And for people that are, you know, listening to this and saying, hey, that sounds great. But, you know, this kind of guy is a smart guy, went to university who is working in corporate America. And, you know, it just sounds like he was almost born with a silver spoon in his mouth kind of thing. Maybe not, but a smart guy, kind of. What are people going to come away from this masterclass with that average normal real estate? Investors can can feel confident and really elevating their game. What what are you guys going to be talking about in this? Master class,

Tyler Chesser [00:16:43] well, at the end of the day, real estate is a vehicle towards creating outcomes that you want in your life, right? Sometimes we get lost that that's really the case. Right. We invest in real estate for a reason, for lifestyle, for impact, for legacy. Right. Those are those are really some of the core items. But the thing that I have come to love about our approach to real estate and really elevate your real estate game is what we're talking about here, is that real estate can create freedom. Right? When you think about freedom, there's really five core freedoms. And what we like the participants who show up to our master class and participate with us in our master class to understand is that we are here to share the five foundational freedoms. So No. One, that's financial freedom. Right. That's one of the things that we all love about real estate, is that we can create financial freedom through investing effectively in real estate. Right. Because you can buy a bad deal and say, well, I bought three or four deals this year, but maybe you have negative cash flow. That's not what we're after. When we think about having true wealth. Financial freedom is the basis of that. It's about having cash flow that outpaces your burn rate, so to speak, and having the resources to do anything that you want in your life. So that's number one. Does that make sense?

Dave Debeau [00:17:58] Yeah, financial. What's what's the second of the five freedoms?

Tyler Chesser [00:18:02] Number two is time freedom. This is the ability to do what you want, when you want, with whom you want. Right. And so at the end of the day, the reason why financial freedom is important is because now, Dave, you and I can sit here and have a conversation and expand each other's thought process and expand the thought process of many others and spend time in ways that really fills us up. So this is really important for us to note is that through developing the strategies and the systems in our real estate business and also expanding our perspective to realize that more is possible time, freedom becomes a possibility as well. So that's number two. Number three is geographic freedom. This is the ability to travel internationally regularly, to see and visit new, beautiful places and to truly experience everything that this world has to offer because there's so much that this world has to offer. I can tell you one one example. I was in Italy with my beautiful wife now who is my fiancee at the time. But I can tell you that I did not have geographical freedom because when I was there, I was in demand constantly. People needed me on every single deal that was happening. They needed my input. I was negotiating a deal. I was in the Amalfi Coast and I'm having a conversation on the phone. So I wasn't I wasn't mentally there. I was physically there, but I wasn't mentally there. But what we are going to talk about is how to be physically and mentally there. Right. In living and experiencing the beauty that this world has to offer. So that's number three, geographic freedom. Does that make sense?

Dave Debeau [00:19:28] Yeah, for sure.

Tyler Chesser [00:19:30] Number four is impact freedom, the freedom to impact other people. Right. So once you have financial freedom, time, freedom and geographical freedom, you can now go and work on things that truly matter to you and do things that make a difference. Right. What is it that you're passionate about? What is it that you love doing? One of the things that I know that I love doing is learning and growing and sharing new experiences with other people because I've seen how learning can transform my life. But what is it that you're passionate about? Are you passionate about helping others who are less fortunate? Are you passionate about sports or are you passionate about fitness or you're passionate about, you know, any other charities? I mean, what is it that you are passionate about impacting the world on? Right. What is what is the legacy that you'd love to leave instead of just wondering about when's our next paycheck coming in or or will this next deal close? It's about having the ability to use this system that we call real estate in terms of impacting other people. So that's number four. And number five is the freedom of relationships. And this is a beautiful thing, because when you have the choice and the ability to stop hanging out with people who drag you down, you can then choose to spend time with people who lift you up and inspire you and open your future to new paradigm, just like Trevor and myself do for each other. At this point, I mean, we've become such close friends and people that really respect each other and admire each other. But we also help each other connect to new friends like Dave, like you and I. You know, this is a beautiful thing. We're beginning a new relationship together. And so we have the freedom of relationships, but we're not weighed down by doubt and fear and worry and anxiety that, you know, we don't have to we don't have to step into it because of the systems that we've developed in real estate. And it comes through bulletproofing your mindset. It comes through understanding that there is a process that we can model. Success rate success leaves clues, just as Tony Robbins has said. So let's model success and let's reverse engineer the steps to get there. Right. This is the you know, we talked about the five freedoms here. This is the big direction that we're going. But it's about reverse engineering those steps and really making that possible in a very practical way. So that's a. We're going to be talking about on this masterclass, I'm really excited about it.

Dave Debeau [00:21:44] Well, that's awesome. That's awesome. So if people want to sign up for the master class, what should they do?

Tyler Chesser [00:21:52] Just go to million dollar investor dotcom again, that's million dollar investor dotcom. Super simple. And all you have to do is just enter in your name and your email and you are in. We're excited.

Dave Debeau [00:22:04] That's right. So that's going to be happening on Wednesday, June the twenty third. I'm going to be there with bells on it with my pad and paper and taking notes like a mad man, that's for sure. Tyler, this has been a lot of fun. I really, really appreciate it. And I look forward to having your big sexy brain, same web class. And we've got Trevor's big sexy brain on there. And just the amount of success you've had and the amount of success Trevor has had and the amount of collective success you've helped other people have through this process. I'm very, very excited. So thank you very much for putting it on. Thanks for being a fantastic guest on the podcast.

Tyler Chesser [00:22:43] Well, Dave, thank you for your big, sexy brain as well. I really appreciate you. And I look forward to seeing you soon. And everyone else who joins us on the webinar can't wait to see you as well.

Dave Debeau [00:22:53] All right. Thanks very much, everybody. We'll see you on the next episode. Bye bye. Well, hey there. Thanks for tuning into the Property Profits podcast. If you like this episode, that's great. Please go ahead and subscribe on iTunes. Give us a good review. That'll be awesome. I appreciate that. And if you're looking to attract investors and raise capital for your deals, that may invite you to get a complimentary copy of my newest book right back there. There is the money partner formula. You get a PDF version at investor attraction book, dot com again, investor attraction book, dot com ticker.

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