TGCI 52: How you can ELEVATE your life?


Episode 52: How you can ELEVATE your life?

EP #52 - Tyler Chesser v2


In today’s show, Pancham interviews Tyler Chesser. Tyler is a successful real estate entrepreneur and a personal growth leader. He is a co-founder of CF Capital and the creator and host of Elevate Podcast.

A seeker of wisdom and knowledge, Tyler discusses on today’s show on how there are no borders to success when you combine effective real-estate investing and continuous personal improvement.

Additionally, he shared his personal stories that could help the audience be inspired to take a leap in business. If you felt the need to take the next big step but not sure how, this show is definitely for you!

Pancham Gupta
TGCI-52-Tyler Chesser
Tyler Chesser

Tune in to this show and enjoy!

Tyler Chesser Quote

Timestamped Shownotes:

  • 3:43 – Pancham welcomes Tyler to the show
  • 4:20 – Tyler’s background information
  • 4:55 – How did Tyler took the leap into real estate?
  • 8:15 – When did Tyler feel the need to switch gears to real estate and do something different
  • 11:39 – How did Tyler seek guidance on real estate?
  • 13:29 – As his businesses are rising, where does Tyler focus his businesses now?
  • 15:48 – How did the pandemic changed Tyler’s strategy? What did he change?
  • 21:07 – Why did Tyler started the Elevate Podcast? What was the thought process behind it?
  • 23:42 – What is the Elevate Podcast all about?
  • 25:00 – What is Tyler’s routine and how has it attributed to his success?
  • 30:48 – Taking the Leap Round
  • 30:48 – When was the first time Tyler invested outside the Wall Street?
  • 31:32 – What fears did Tyler have to overcome when he first invested outside the Wall Street?
  • 32:16 – Can you share one investment that did not go as expected?
  • 34:30 – What is one piece of advice you would give to someone who is investing in the Main Street?
  • 36:45 – Tyler shares his contact information

3 Key Points:

  1. Why you should surround yourself with the right people
  2. Why you should surround yourself with the right people
  3. Importance on the balance between personal growth and real-estate investing

Get in Touch:




Welcome to The Gold Collar Investor Podcast with your host, Pancham Gupta. This podcast is dedicated to helping high-paid professionals to break out of Wall Street investments and create multiple income streams. Here is your host, Pancham Gupta.


Hi, this is Joe Fairless. If you wanna diversify out of Wall Street investments, then listen to The Gold Collar Investor Podcast.


Pancham: Welcome to The Gold Collar Investor Podcast. This is your host, Pancham. Really appreciate you for tuning in today. Let’s get into today’s show. Tony Robbins says that success in anything is 80 percent psychology and 20 percent actual mechanics. This part is so true. It does not matter in what field or sector you are working in. This principle is true across the board. Whether you are in the tech industry, retail industry, fishing, tourism, real estate, it does not really matter. It also does not matter what kind of role you are in in that particular sector. You can be a salesperson, analyst, banker, engineer, it does not really matter. What matters is your mindset and how you are making the best out of each situation. There is a quick little story about two door-to-door salesmen. One day, it was raining heavily and one salesman woke up and said, “Oh, man, such a heavy rain. There are not going to be many sales today so I’m going to skip.” The second one wakes up and looks at the same heavy rain and says, “Oh, man, such a heavy rain. There are not going to be many salesmen selling today.” So, the circumstances are the same for both of them, it’s how they really reacted to them that mattered the most. So, realizing this, I have decided to do shows that are related to mindset as well. I will be bringing guests on the show to help you get all the tools that are necessary to get better in investing in your area of expertise. My guest on this episode is one such person. We met at a conference once and we felt a connection right away. Tyler has this infectious, positive energy and mindset that helps elevate people around him. A bit about Tyler. Tyler Chesser is a successful real estate entrepreneur and personal growth thought leader who believes anything is possible by combining effective real estate investment with constant and never-ending personal improvement. Tyler is the co-founder of CF Capital, a private equity real estate firm which focuses on acquiring and repositioning multifamily assets in the Southeast, provides institutional quality services to its residents, and outsized returns to its investment partners. Additionally, Tyler is the creator and host of Elevate podcast. Elevate is the masterclass where Tyler dissects the elements of exceptional achievement and lifestyle design with the focus on personal growth and real estate investing. More than anything, Tyler is curious and a relentless seeker of wisdom and knowledge and regularly devours books, consumes intuitive data, and is a generous teacher and leader to many around him. Tyler, welcome to the show.


Tyler: Thank you, Pancham. It’s great to be here with you. How are you?


Pancham: I’m doing awesome. It’s always great to be with you, connected to you, it’s always a positive conversation and I’m looking forward to this show today.


Tyler: Yeah, thank you, and I couldn’t say, you know, more, you know, really for you. I know that every time you and I sit down together, we learn something and we’re better off for it, so let’s serve the listeners today. I’m excited.


Pancham: Yeah, I’m excited for the listeners and, you know, are you ready to fire up my listeners, break out of Wall Street investments?


Tyler: Absolutely, let’s do this.


Pancham: Let’s do this. So, Tyler, tell our listeners about your background and the person behind that background.


Tyler: Absolutely. I’m always excited for that because, you know, we’re all people at the end of the day. We get so focused on our businesses, we get so focused on our goals that sometimes we forget, you know, the most basic piece is that we’re human beings, right? We’re here to, you know, live a life of fulfillment, to contribute to others, to grow, to become more, to live, you know, maybe a destiny that was preordained for us, maybe one that we can create for ourselves. So, anyway, I’ll get off my soapbox here and let you know sort of a little bit about myself. When I got into the professional world, I started in the corporate world and it was interesting because I never considered another path. You know, there was never really consideration for anything other than riding the corporate ladder and my sort of approach was in international marketing and I was actually always fascinated with, you know, sort of the psychological aspects of business and consumer behavior and why certain decisions are made by people and why people behave in certain ways and so I was always fascinated by that. I was always fascinated by, you know, why certain brands carried more value than others or perhaps a different type of value than others. So, that was always fascinating to me and it continues to be fascinating to me to this day and I say that because I got started really kind of as a professional in that capacity and I learned fairly quickly that, you know, I began to tolerate my life. I began to say, you know what, I’m riding this corporate ladder and, you know, it’s gonna be 20, 30 years before I get to where I wanna be here just based on sort of getting, you know, pushed back in the workplace when I was asking for promotions or asking for raises. It was more so, “Hey, you know, you gotta stick around, you gotta be in the saddle for a certain amount of time before you get to that next place,” and I found that to be interesting because it was really more so, you know, to a large degree about that time in the saddle, about the politics of how you kind of rode, you know, that ladder that kind of started to be opposite of resonate with me. I don’t know what the word is there but it started to really kind of eat at me and so I got really kind of dissatisfied with that and I sort of looked around and said, hey, you know, what else is out there for me? And really it took me years from that point to where I really made the leap into real estate and I actually got started in the real estate business as a real estate agent and started to sell properties and started to sell income-producing properties from there and that’s when I learned about the power of assets, the power of cash flow, the power of real estate investing, and so then I started investing in real estate, so it was kind of like a leap. I kept making these leaps. It was like from one sort of, you know, rock to the next across the river, right? And I started to learn, you know, about real estate investing of course through, you know, our friend and through, you know, our mentor, Robert Kiyosaki, when he talks about Rich Dad, Poor Dad, of course, right? I mean, how many people got started in the way that they changed their thinking through that book and of course it totally changed the way that I thought about life and thought about business and wealth creation and so I started investing in multifamily real estate from an active and from a personal level and started to buy properties that I was selling and it was so interesting because when I read that book, he didn’t tell me how challenging it would be. He didn’t tell me how many things that I really needed to be prepared for to effectively build an asset base, and so I learned that the hard way in many ways but I continued, you know, over the years to build my own portfolio and now I’ve kind of gotten to a point now where we’re raising capital for larger deals and I’ve learned that the name of the game is scale in many capacities and so, you know, that’s been kind of a 50,000-foot view of my journey but I feel like I’m only getting started.


Pancham: Absolutely. Thank you for sharing that. There are so many things that I wanna dive into. Let me try to dive into a few of them. So, you said from international marketing to, you know, you got into this mindset of like where you were not happy and you were starting searching for new thing and you became an agent. How long was the time from the time you actually initially thought of it that there is something that’s missing, from that point on to actually becoming and switching gears and doing something totally different?


Tyler: I mean, honestly, it was probably 2 or 3 years at least, because I didn’t have any other reference points for doing something different. You know, I kind of grew up in a middle-class, you know, middle America type of life and my references were, you know, that a high level of success was reaching a high level of success within a corporation and growing there and, you know, being promoted and maybe even being headhunted by another organization, so the first thought that I had was, alright, I need to get my resume really built up, really bulletproof and very impressive and start to send that out and start to look and see, well, what other options could I take a lateral leap or maybe even a slightly above lateral leap to another organization so that was my first thought and it was interesting because as I went through that, I started to think, well, wait a minute, what would be different about that organization than this organization? And I started to recognize that maybe, you know, the solution to the problem that I was, you know, proposing was not really the real solution, it was actually not really solving the problem so I wasn’t fully aware of what my discontent was and so then I started to recognize, well, wait a minute, maybe if I’m willing to take a little bit of a leap, I can actually solve the real root cause of the issue which is, you know, that I wasn’t satisfied, that I was tolerating my life, and ultimately, you know, one of the words that I think is, it’s maybe overused to a certain degree and it’s also elusive to a certain degree is “fulfillment” and so what I learned through a long sort of trek there is that to reach fulfillment, I needed to really know myself. I really needed to know, you know, what is it that I want out of life and I learned that I’m so driven by growth. I’m so driven by becoming more and by leading others to become more and leading others to grow as human beings because I firmly believe that, you know, if you don’t grow, you’re dying. If you’re not growing, you’re dying. There’s no in between. You can’t just be stagnant. It’s just like anything else in, you know, life and reality and nature, you grow or die, and so that’s one of the core tenets of who I really realized that I was as a human being and the other thing was contribution, giving back to others and obviously I mentioned that in helping other people grow, but I learned that being an entrepreneur sort of scratched both of those itches and I also learned that real estate is one of the greatest wealth-creation vehicles in our world and in our history as human beings sort of species and so combining those things and creating, you know, amazing practical means to the ends of wealth creation, cash flow, and all these things, in addition to giving back to other people really was who I was meant to be as a person so that’s kind of why I made that leap and the rest is history but it continues to make history each day.


Pancham: It’s actually funny that you say that where you actually beefed up your resume to look for some new opportunity and soon you realized that it’s a figure 8. That’s what they say. You know, like you keep running but you’re going back to the same thing where you were and it might be a different place, different kind of role, different people, but at the end of the day, it’s exactly the same thing and I actually felt exactly the same way in the corporate world. And let me ask you this, right? So, did you seek any help to actually come to that conclusion or you did all that by yourself?


Tyler: I did. I sought out a lot of help and really it was a seeking process for me because it took me, you know, like I mentioned, a few years. Probably the first year was I was totally in my head about it. I was just irritated and, you know, a little bit irritable. I wouldn’t talk to other people about it. I don’t think I was fully consciously aware of my discontent because everybody told me, it was like, “Look, college days were the best days of your life, you know, this is adulthood, this is what it is,” and so I thought that this was just how it was and then after about a year or so of feeling like that, perhaps under the surface, I started to recognize, wait a minute, it does not have to be this way. So I started to ask around. I started to network and started to dig in and say, you know, who else may know a different path for me? What other skills do I have? I was looking very practically. It’s like, alright, if I’m not going to apply at a different organization, you know, and share my resume with them, what other direction could I go? So I started to ask around and I came across, you know, a few individuals who were in the real estate business and, you know, the only thing I ever thought of when I heard about real estate was houses, you know, buying and selling single-family houses. To me, when you said the word “real estate” going back to branding earlier, to me branding of real estate was about single-family homes. And so that’s all I knew about it but as I dug in, I learned that there is so much more. There’s such more of a breadth and, you know, a wide variety of different specialties that you can take within real estate, whether it’s just, you know, the way that you operate or the asset class in general and so my thirst for knowledge and growth started to be quenched with this huge myriad of different options through real estate so I started to learn and dig in and, you know, that’s when I started to take the path of selling real estate and that’s where, you know, my entry was to this business.


Pancham: Great, great. So, fast forward to today, now, like what’s your focus now? You mentioned cash flow and real estate and also scaling up your business and getting into multifamily so is that all the focus right now as far as the business goes?


Tyler: Yeah. So, we focus on multifamily investment. CF Capital is a private equity firm and we focus on multifamily communities, you know, generally 100- to 300-unit communities across the Southeast and Midwest United States and, you know, I kinda scaled up my active business, you know, investing in smaller, kind of midsized multifamily properties, 50 units and less, and I learned that the larger property I did, the better I could, you know, really operate that property just based on the economies of scale, the team that I could put on the field, and obviously the better, the bigger we go, and everybody was asking me, “Hey, you know, how are you doing this, you know? How do you have time?” And obviously I’m a real estate professional and have been for 7 years so I have the ability and the benefit of just being in the business, seeing the deals, and really operating from that capacity but so many others are not and so many others have not spent the time in the saddle that I have and, you know, the others that I’ve really invested in mentoring have as well and so, you know, I think there’s a huge benefit in me offering opportunities, myself and my business partner offering these opportunities to others who love real estate, they love what you and I talk about on a daily basis and, you know, they wanna be a part of that and so giving others the opportunity to do that and mutually benefiting everyone has been a great way for me to grow so, you know, I operate in that capacity in terms of private equity investments in multifamily communities. In addition to that, you know, I coach real estate investors really all about high performance, you know, getting to that next level so if you’ve had a ton of success but you wanna reach that next level, those are the type of people that I work with so it really fills me up and I’m excited to get up every single day. The other thing, of course, that I know you love is podcasting and reaching and meeting people like yourself and serving listeners through Elevate is the podcast that I run so there’s a ton of fun there. It’s all about personal growth in real estate investing. That’s kind of my world.


Pancham: I would wanna get into the podcasting part a little bit later on, you know, I have a few questions there. So, let’s talk about the current situation, right, like COVID-19, we’re in the middle of a pandemic, in March, the world was coming to an end, right, there were so many things that were happening. People were worried and there’s government shutdowns and all that. So, in the middle of all this, like how are you changing your strategy and, if so, what have you changed? 


Tyler: Well, I think first of all it’s very important to be nimble. I mean, that’s one of the benefits of being a, you know, a small, private equity firm is that we’ve got a lean team. Actually, you know, all of our team is really working remotely so that was one of the things that we had to pivot immediately to was working remotely so just from, you know, our approach, that was, you know, it was a shift that was slightly painful for a few weeks but now we’re more productive which is amazing and it’s exciting, so I think given the opportunity to be flexible from those standpoints is super important but as far as from strategy, you know, looking at the global environment, looking at the national environment, even hyperlocal, per markets, you know, being aware is super important. Being aware of, you know, where we are right now, what’s the possibilities for the future. So, you know, you look at multifamily, obviously, it has fared pretty well over the past few months in the pandemic, but obviously anything is possible from here, you know? Where the stimulus goes from here. I think it’s really important for us to keep our, you know, our finger on the pulse from that perspective because obviously, you know, rent collections have been extremely strong and we’re blessed and thankful for that and we wanna continue to support our tenants in making sure that they get on their feet, making sure that they have access to every resource that is available to them because our level of success, you know, is directly correlated to the level of success that our tenants experience, so I think that, you know, you really kinda start from there in terms of what are we looking at in terms of employment. Obviously, we’ve had a major disruption from an employment perspective which, traditionally, has a direct correlation to the level of success for your properties but obviously we’ve had a huge help from the federal government in many capacities as it relates to stimulus. So, you know, looking at that and saying, alright, well, if this continues, then what? If this does not continue, then what? And so, you know, we’re underwriting new deals, we’re looking at what is our vacancy, what’s our historical vacancy been over the past 12 months, over the past 3 years, what does that submarket look like from a historical vacancy or bad debt perspective overall, and what is possible moving forward because we’re certainly, I know one of the most overused terms in the past several months has been “unprecedented” but it certainly is unprecedented in many ways, so what has happened in the history, in the historical figures that show you, obviously, you need to be aware of but also recognizing that they may not be relevant moving forward, so what can you do to fully stress test your deals and look at what’s the worst-case scenario and making decisions based on that and can you protect capital, because one of the things we love most about multifamily real estate is that it is a capital preservation vehicle. Not only from an inflation perspective but, you know, from so many different capacities. You look out there. I mean, there are so many unsafe financial vehicles right now in my opinion and I feel like multifamily is one of the few safe harbors so we look at it and say, what can we do to make sure that this continues to be a safe harbor? How can we overfund our reserves? How can we really stress test all of the different capacities of our pro forma and, as you know, I know this for sure, pro forma is a guess. I mean, we’re putting our finger in the air and saying, we think the wind may blow in this direction, but, you know, it’s always an educated guess and remaining educated based on the global macroeconomic environment in addition to what’s happening on the ground I think is super important and making decisions with that. So, you know, one of the things that we do is we consume data constantly, whether it’s, you know, reading articles or reading reports or, you know, really diving in specifically into deals and models and, you know, market reports and all these different things and so synthesizing that data, it’s so interesting how it really kind of goes into the cells of your body. At some point, you are able to make these gut decisions and you’re able to say, you know what, based on all of this, I’m not entirely sure why I’m making this decision. Obviously, I understand I can explain to you intellectually, but at the end of the day, we have to make the decision that feels most appropriate based on all of the information that we’ve gathered. So, happy to dive into any of that.


Pancham: No, that’s great. You mentioned so many points that we have been looking at and based on all this data. Like you said, you know, that’s called experience, right? Getting that intuition is only something that you get after looking at so many things, dealing with so many things over the years and then you get that intuition and with this unprecedented situation, like you said, you know, we have the data, we know we are serving one basic human need which is shelter and as with Maslow’s hierarchy of needs, it’s one of the basic needs and I don’t think it’s going anywhere but, again, at the same time, if stimulus packages go away, like you said, what would happen? It’s yet to remain, you know, we have to see that and just see how it would go. So thank you for sharing that and now I want to talk about, you alluded to this earlier, that you started this amazing podcast, right, Elevate, you call it, and, you know, you just wanna elevate people around you. What was the thought process behind that and why you actually started it?


Tyler: Yeah. So, for me, the key to success, at least thus far for me in my life, has been a combination of personal growth and real estate investing and personal growth has really been actually the secret to everything for me because, you know, I didn’t know anything about real estate getting into this business and it was so challenging and it was such an uphill battle and as you mentioned, you just mentioned experience, and so certainly you get to a point where all of this information comes to a point where you can make effective decisions but I was so overwhelmed in the beginning. So overwhelmed with learning the business, learning the vernacular, learning how to navigate the environment. Learning to, you know, build my network and build relationships and then also learning how to deal with stress and learning how to deal with overwhelm, so I started to look for answers and, you know, the first place I started was hiring a coach and I hired a coach and he was always teaching me things that, you know, and he would always reference books that he read and so I started to pick up these books and it was so interesting because I would read one book and I would say wow, this is a life changer, as we talked about, you know, Rich Dad, Poor Dad, it was like total mind shift and there are so many others where that came from and when I read a new book, it was like I can’t imagine what I would have done if I didn’t know this information so, you know, personal growth became really what I became obsessed with and, you know, I started to learn about mindfulness and meditation and how to manage your own emotions, how to invest in your own health because health is wealth, right? If you have all the money in the world, just ask Steve Jobs and God rest his soul, of course, you know, but when he was on his death bed, he said, “If I can give every single penny that I have, you know, access to back to get my health back, I would,” and so learning about how can we show up with great energy, how can we live a long and vital life from that perspective. You know, learning about your own financial health. You know, how to set up your own sort of, you know, your legacy, right, for your family and for the people that you care about and so what can you do to give to other people? What can you do to understand the psychology of other people? You know, so it is about a multidisciplinary approach. The more that I’ve learned, the more that I’ve wanted to know and the more effective that I’ve become, not only in leading myself but leading others and building a business and creating new opportunities, so it has been a very multifaceted and dynamic approach but, you know, it’s really the most exciting, you know, journey that I’ve gone on in my entire life so that’s what Elevate is all about. It’s about bringing those people on and sharing that message with the listeners to recognize that anything is possible. You can actually elevate your life without limits if you continuously, constantly, and never end your improvement, and you invest successfully in real estate. Or, you know, what other vehicles are out there? Obviously, Pancham, you and I love real estate. We believe so deeply in real estate. But guess what, it’s not the only vehicle. There are other businesses. There are other assets that you can invest in in addition to real estate. It just happens to be what you and I are experts in. And so, obviously, there are many better benefits in real estate than in any other asset vehicle out there that I think we can probably go down a huge rabbit hole and talk about but really that’s what Elevate is all about. It’s about the combination of those two forces towards creating a life that has no limits. So, it’s super exciting.


Pancham: It’s a great brand that you’ve created. I absolutely love it and, listeners, if you haven’t checked it out, do check it out. It’s awesome. So, that’s great, Tyler, and I want to move on to the next section of the show but before I do that, I have a question for you that I recently started asking every single successful person that I, you know, interview and there are common themes that I’m learning. So, one theme is around the routine, your daily routine, okay? And, you know, whether it’s your morning routine, whether it’s your evening routine, and do you have one? If so, what is it and do you think that has attributed to your success?


Tyler: One hundred percent. You know, it’s so interesting. I’ll take a bit of a step back and tell you that recently, you and I were talking about this before the show, I had Seth Godin on my podcast recently which was such an honor, such an amazing individual, and I was talking to him about getting 1 percent better and he says, “Look, I don’t buy into the 1 percent thing.” He says, “Do you think that we got to the moon by getting 1 percent better?” and I said, wow, that was quite an interesting response there and obviously he went on and on with that, but I would say that I believe deeply in the compound effect and I believe deeply in habits, in routines, and so, for me, routines are extremely important and every single day, I get up, you know, I get up between 5 and 5:15, I’m an early riser, and it’s not always easy for me to do that, but, you know, I have to get in bed, you know, at 9:30 or 10 o’clock to be able to be rested enough to do that, but the first thing I do is I drink water, you know, because I’m always very thirsty and, you know, there’s been 7, 8 hours of life without water and so I’ve always started with that and from there, you know, make a cup of coffee, I do a 10-minute meditation, and I read for 45 minutes to an hour and so, for me, at that point, I can fill my mind with new information and I can give myself, you know, time to think of new ideas or glean new insights and so if I give myself in the morning to invest in myself, whether it’s my own, you know, observance of my own thoughts or sitting with, you know, my breath and giving myself some space to feel calm and to recognize that I can actually bring that with me at any moment in my day or, you know, the rest of my life, that gives me so much time through the meditation and then from there, reading is super important because as I mentioned, any new book, it’s like, wow, I can’t imagine what I would have done without this information. From there, I read a daily sort of affirmation of things that I’m looking to become. You know, things that I’m looking to create in my life and I actually have an identity statement as well that I read aloud to myself and, you know, that is one that I’ve been conscious in creating, you know, who am I becoming and what is it that I’m looking to serve and what am I looking to grow, and so it’s so interesting is that doing that in the morning really kind of plants the seeds within my subconscious mind in that I know that I show up more so like the individual that I want to become so that’s really important to me. I also look at my goals. It’s really interesting. I actually have a Microsoft OneNote app on my phone and I have all of these in different tabs so I can do to my identity statement, I can go to my affirmations, I can go to my goals and look at them very quickly there on my phone, and I try to not look at my phone otherwise in the morning because I don’t wanna be reactive. From there, I do go and get a little exercise in. I’ll typically either go to the gym or do a home work-out and get the blood flowing, and from there, it’s time for me to get started on my day and I’ll have a breakfast of course before I get started on my day. That’s my morning routine and from there, I’ve invested in myself and I know that anything else that happens, I’ve had that time and then I can go serve and be the greatest version of myself to other people.


Pancham: That’s amazing. Amazing. So, thank you for sharing that. How long have you been doing this routine now, like religiously?


Tyler: I’ve probably been doing this routine for the past 4 years —


Pancham: Four years, wow.


Tyler: Yeah. Absolutely is a compound effect because it’s so interesting. I mean, like even just something as simple as — like yesterday I had to update my financial statement because we were making a run at a new deal and I need to make sure that I’m communicating with banks and, you know, all of these things. I was updating that and I actually had a financial statement from 4 years ago and it’s amazing how vastly different it is and it’s not that — of course there’s a lot of luck involved, there’s a lot of that, but I think you do create your own luck to a certain degree and starting with those routines and creating these conscious habits have been transformative from my financial picture but also just me as a human being and as a person and my quality of life has risen drastically so I think that that is a central role as to why that, you know, I’ve really transformed my life and I continue to do so. I want to continue to evolve as a person. You know, every 30 days, I wanna look back and say, wow, I can’t believe I was making those mistakes 30 days ago. I can’t believe I was thinking in that way. I can’t believe I didn’t think this big. So, I wanna encourage everybody to challenge yourself to think bigger and to be willing to change, be willing to evolve on a constant basis. That’s really served me well.


Pancham: Great. Well, thank you for sharing that. Now, we will be back after this message.


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Pancham: So let’s move on to the next section of the show which I call “Taking the Leap” round. Tyler, I ask these four questions to every guest on my show. My first question for you is when was the first time you invested outside of Wall Street?


Tyler: It was in the fall of 2016, that was the first time I invested in a multifamily property.


Pancham: Wow, and that was your first time outside of Wall Street? Before that, you had never invested in any property?


Tyler: That’s correct. Everything else was — you know, I had invested in my business so perhaps you could look at it, you know, and say 2013 was really when I started my business and I was selling properties so perhaps from that perspective, but as far as, you know, a specific hard asset, it was not until 2016 and obviously, you know, I learned so much from now since then but I’m sure we’ll talk about that.


Pancham: Great, thank you. Thank you for sharing that. So what fears did you have to overcome when you bought that property in 2016?


Tyler: You know, I had to overcome a lot of fears. I mean, mainly just the unknown, the uncertain, and really, I didn’t have many reference points to other people who were doing what I was doing, so, you know, other than the people that I had sold properties to or I had worked with from that perspective so, you know, I didn’t have a ton of family in the business so it was a lot of uncertainty but I knew that if I just took action that I would figure it out and we’ll talk probably about some of the mistakes but, you know, even from that perspective, I was not prepared for what I was about to endure, that’s for sure.


Pancham: Okay. Now, fear of unknown is probably the biggest fear people have. So, okay, can you share with us one investment that did not go as expected?


Tyler: Yeah, it was that one. I mean, it was absolutely that one because, as I mentioned earlier in the show, we talked about Robert Kiyosaki, Rich Dad, Poor Dad, you know, he didn’t tell me that I need a team. He didn’t tell me that, you know, I need to understand the difference in distressed and value-add. He didn’t tell me, you know, that a submarket is so hyperlocal and that one block is vastly different than another block so, you know, the first deal that I invested in was a — it was a distressed multifamily deal. It had been mismanaged for decades. It had been, you know, there’s tons of deferred maintenance, all these different things. So, I knew that it was a good opportunity and ultimately time healed all the wounds and it ended up being very successful, but in the beginning, man, it was like sleepless nights because I had tenants who weren’t paying, I had, you know, many physical problems with the assets and, you know, it was multiple buildings and, you know, I just learned so much. I learned about what was a loaded rent roll. I learned the difference of course in a distressed asset and a value-add asset. I learned what makes a good tenant, what makes a bad tenant. I learned so much. I actually managed the property myself for the first 6 months and it was like, you know, the school of hard knocks — 


Pancham: Yeah.


Tyler: — but, yeah, that’s — it was very challenging.


Pancham: How many units were there —


Tyler: Eight units and a storage garage. Nine rentals total.


Pancham: Got it, got it. You know, actually, when you just said that, you know, Robert Kiyosaki did not teach you about all this, right? You know when — back, way, way back when I read this book for the very first time and I was reading the reviews online about the book and all that, you would see about 10, or maybe 5 to 10 percent of the reviews were really, really negative on the book and those reviews were exactly that, “He didn’t really teach me about any of that,” or, you know, “He talks about fluff, there’s no meat in this,” and like you said, it’s not about — he’s just showing you the path and you have to be the one, like in Matrix, you have to walk on that path and actually make it happen.


Tyler: I agree.


Pancham: Thank you for sharing that. So my last question for you is what is one piece of advice you have for the people who are thinking of investing in main street, that is, outside of Wall Street, like when you were looking back into 2015, let’s say.


Tyler: Yeah. Well, you know, it’s so interesting because you asked me, you know, when was the first time I invested out of Wall Street and everything up until then was about 401(k)s, it was about the 2050 plan, the 2060 plan, whatever, you know, those kind of things, and it’s so interesting because you don’t really stand up to have like a team when you’re taking that type of investing strategy but when you shift and you’re investing more in main street, you’ve gotta surround yourself with the right people and I think also you’ve gotta be humble. One of the things that I was not humble enough, I didn’t want people to know how little I knew so I wasn’t willing to ask the questions that I vitally needed to ask, so I would say when you’re starting, show your humility and be willing to ask questions. Be willing to show that you don’t know everything because it’s interesting. The more that I’ve learned and the more that I’ve surrounded myself with folks like yourself, Pancham, or others who, you know, know more than I do, they ask more questions and so I would say be humble and be willing to ask more questions and be willing to challenge yourself to ask better questions as well because those who ask better questions get better answers.


Pancham: It’s so great that you mentioned that. I actually have a book right here and recently just got delivered, literally 2 days ago. It’s called — the book’s title is Ask! and it’s by Mark Victor Hansen who wrote the Chicken Soup for the Soul book and he says that there are three things that you need to ask every day, like you need to ask others, you need to ask yourself, and then third is you need to ask God. So — and basically, his title of the book is like anything from your dreams to the destiny, only thing that’s in the middle is ask and these are the things that you need to do and so thank you for sharing that. I have not read the book, it just literally got here, and it’s one of my to-do list. That’s great. So, Tyler, you have added a ton of value. Tell the listeners how they can reach you, connect with you, and anything that you wanna share.


Tyler: Absolutely. So I think the best first step for everybody is to go check out Elevate Podcast. We’re on every single podcast app, you know, or YouTube so go check us out there, and obviously there’s a ton of content for you to dive into and really to get to know me better. You can also find out more about our company, CF Capital. The website there is or, of course, my personal website where you can learn more about coaching or you can learn more about what I’m doing to add value to others through consulting is or, of course, anywhere on social media but, yeah, those are some easy places to get started.


Pancham: Great. Thank you for sharing that and thank you for your time today.


Tyler: My pleasure. Thank you for having me, Pancham. I really appreciate it.


Pancham: Thank you. Thank you.


I hope that inspired you today. Tyler has wealth of knowledge. Thank you for listening. I appreciate you. If you have questions, e-mail me at Until next time. Take care.


Thank you for listening to The Gold Collar Investor Podcast. If you love what you’ve heard and you want more of Pancham Gupta, visit us at and follow us on Facebook at The Gold Collar Investor. The information on this podcast are opinions. As always, please consult your own financial team before investing.

EP #52 - Tyler Chesser v2

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