What’s the best way to grow as an investor? Today’s guest says it’s all about how you elevate your mindset and invest in yourself. Tyler Chesser, CCIM, is the co-founder and Managing Partner of CF Capital and host of the Elevate podcast. Not only is he a successful investor himself, but he also helps other real estate investors, leaders and entrepreneurs transform their businesses and lives. Tyler joins host Sam Wilson to share that mindset is key to continuous business and personal development. Tune in for valuable life and business advice to help you elevate and unlock the keys to success!

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Elevate Your Investor Mindset With Tyler Chesser, CCIM

Tyler Chesser, CCIM, is a high-performance real estate entrepreneur who helps real estate investors, leaders and entrepreneurs transform their business and lives. As a successful real estate investor with a background as a former perennial top-performing commercial real estate broker, Tyler started investing in multifamily real estate in 2015 as a way to build wealth and great diverse income streams for his family.

Prior to launching his real estate investing firm, CF Capital, Tyler spent over seven years in the business as a founding principal with a successful commercial brokerage company, real estate investor, professional speaker and award-winning sales professional. Tyler offers a range of services and programs for syndication of private passive investment opportunities, individual to group business coaching, real estate consulting, keynote speaking and hosts a top 200 business podcast internationally called Elevate. Tyler, welcome to the show.

Sam, thank you so much for having me. How are you?

I’m great. Thanks for coming. This will be a blast. I’m looking forward to it. The same questions I ask everybody who comes on the show. I know we got a lot out of your bio there but give us a little color on this. Where did you start? Where are you? How did you get there?

I started my career as a corporate individual in the corporate world. I never knew I was going to be an entrepreneur and get into real estate. I was always taught to go to school, get good grades and get a good job. By the time you’re 65, perhaps you’ll have a little nest egg there that you can ride off into the sunset with. It’s interesting because as I became a corporate employee, I started to feel maybe this wasn’t the right fit for me because I started to feel like I expected to be in this seat from this time to this time.

I got to take my work home with me as well. If you want me to be available on a Saturday morning or maybe even a Thursday evening for a conference call across the world, I got to do that. It doesn’t matter necessarily my effectiveness but it matters how long I have been in that seat. Who likes me in the organization? What type of politics have I played, whether or not I’m going to earn more money?

For me, that was an early part of my career that defined a lot of the decisions that I made thereafter. Long story short, that internal turmoil that was also external in many ways led me to reinvent myself. I reinvented myself by getting into real estate. I started in real estate as an agent then I founded a brokerage company. I learned quickly when I was doing that it was a great way to generate fees and income but it wasn’t a great way for me to generate wealth. While I was investing in real estate along the way, if I wanted to create real wealth, it came through focusing on investing.

Every single day is a constant evolution. I’ve become super passionate about personal development, personal growth, mindset, surrounding myself with people like you. That’s where Elevate Podcast came from. It’s all about mindset, mind expansion and personal development for high-performing real estate investors because that’s what I’m all about. The thing that I love about being an entrepreneur and investor is that it’s a challenge. It’s almost the greatest personal development process that you’ll ever go on. For me, I’ve transformed as an individual through this entire, in many ways, uncomfortable process. That’s a little bit about my background, where I was and where I am.

Maybe we can spend a few minutes digging into that transformation process. You’re sitting in that seat and figuring this out going, “I could do this for 40 years. It’s all about tenure and time in the seat.” What were your next steps? You said, “I’m going to get out of this.” I know you said you went and became an agent which was interesting. Was that on the residential or the commercial side? How did you work that out? What were some of the things you took early on to help you drive and guide your mindset?

You’re either going to win or going to learn. If you fail, that’s only feedback. It’s not fatal.

You’ll find this funny. The first thing that I did when I started to feel that discomfort was revamped my resume. I’m like, “I’m going to go to a different organization.” This organization is my problem. What I didn’t realize is that it’s the culture of Corporate America and being an employee in that type of environment. It has nothing to do with the organization. It’s the way that the entire system is set up. That was my first thing. I bumped my head a few times and then I realized that was not my problem. My problem is taking my future in my control. Bring it back into my control rather than hoping and wishing that I get a promotion, a raise and get more than the cost of living.

I bought a house a few years before this. I was in international marketing at the time. I loved what I did but I didn’t love the environment that I found myself in. I was asking everyone that I knew, “What else could I do? What else would I be good at?” My realtor told me, “You need to come to the seminar. Come check us out and see what’s up.” I’m like, “I’ll check it out.” At this point, I’m like, “Anything, whatever it takes, I want to make a change.”

I went to the seminar. They gave me a personality test and it says, “You’d make six figures if you were a real estate agent.” To me, six figures were every bit of money in the world at that point in time. I said, “I can get my license. I can do that on the side.” I did get my license. I started selling residential real estate on the side. Within six months, I doubled my income. I also said, “This is great but also, I don’t love residential real estate because there’s a lot of emotions involved and all these things. What else is there?”

It started me on this constant evolution path because then I said, “I got my license. I created more income, which was one of my issues, but this isn’t what I love.” I stumbled into commercial real estate. Then I started selling commercial real estate, multifamily office, retail land and industrial. I was getting all the food groups from a small local investor perspective. As I leaped into that full time, I found a niche in multifamily and became known as the apartment guy. That was the early part of my trajectory into real estate.

 

What did you do mindset-wise? Your Elevate Podcast focuses a lot on mindset, personal growth and development. Those were the tangible steps you had taken but what were some things you did along the way to change the way you thought?

I was grateful early on. My first broker that I worked for, with who I hung my license, encouraged me to hire a coach. My coach was teaching me all about how to build a business by referral, developing systems and developing not only ways of communication but developing marketing techniques so I could establish a presence in the marketplace. That framed well with my background as a marketer but my coach was always telling me things about books that he read and things that he learned from books that he was sharing with me based on certain learnings that he had read and all these different books. I remember there was one book that he kept referring to and it was called Think and Grow Rich by Napoleon Hill.

Most of the readers, I’m sure you’ve heard of Think and Grow Rich if not have read once, twice or maybe even more times than that. The title of that book was intriguing to me. It was so interesting because at this point in time, I was several years out of college but I remember when I had graduated college, I told myself, “I’m retired.” I was busy doing things in college. I was active. I was the president of my fraternity and all these things.

I was like, “All I have to do is work. I’m retired.” That was my mindset but until this moment that I heard it, I was like, “If he’s telling me there’s a book called Think and Grow Rich, then I’ll check that out.” I started reading that book and my eyes were crossed. I was like, “What is this guy talking about?” This is written in 1920s pros. What do you mean you can think and grow rich?

This was a whole new paradigm and world. It was almost like a labyrinth. When I opened this door, I continued to dig into this. My life changed when I learned the power of my mind and the power of what I feed my mind. What seeds do I plant in my mind? Where’s my intention? Where’s my focus? Am I thinking bigger? Am I leveraging my subconscious mind or am I just using my conscious mind? I grew up in a middle-class background.

Nobody’s talking about the subconscious mind, autosuggestion and these kinds of things. No one’s thinking about how we can create substantial, massive wealth, not from a selfish perspective or anything. It was this whole new world and I became ultra fascinated in it. I must become more fascinated than that than real estate. That led into more passion for me to grow my effectiveness in real estate because I learned about what the power of my mind was. That was my first entrance into mindset.

I bet that it’s a continual growth cycle. At this point, you’re probably still going, “There’s so much more out there to know and learn.”

I know you would agree with me on this, Sam. The more you learn, the more you realize you don’t know. It’s crazy because there is a certain level of ignorance is bliss. When you don’t know much, you almost feel like, “I got it all down.” The thing about it that’s cool is that in real estate, being an entrepreneur, being an investor and evaluating whether it’s economic circumstances, psychological behavior, migration patterns, statistics, the way that we feel and think from our emotional perspective, the way that we behave, the way that habits impacts our life, when you learn all of these things and how they’re all interconnected, you start to realize, “There’s so much more growth for me to step into.” It’s exciting.

The thing that I’ve fallen in love with is learning. I know that some days are challenging and overwhelming but I know that no matter what, I’m going to either win or learn. If I fail, that’s only feedback. It’s not fatal. When I get that feedback, I can say, “Maybe I lost some money, made a mistake, did something wrong or someone’s mad at me but I learn. Through that experience, I can do better next time.” That’s also a fundamental mindset shift as well. No matter what, you can take action. We can be worried, scared, fearful but that doesn’t help us move forward. If we move through discomfort, take action no matter what and learn that we can learn whether we win or lose, that’s a powerful thing.

Give us some real-life examples where you’ve had to move through discomfort.

I was having a conversation with my wife. We have so many things going on. We acquired another deal. We closed 132 units. Months ago, we closed a 247-unit deal in another nearby market. That’s a heavy value add property. We’re migrating from one technology system to another in terms of our investor management. We’ve got a lot of things moving at once. We’ve got some things going on in the home front. My wife and I are expecting twins. We are moving through discomfort constantly.

It’s this conversation that I have every single day. It’s like, “Do we pull back on some things? Do we slow things down and pull the throttle back? Do we contract or do we expand through this?” Even somebody like myself, who’s so committed to mindset, learning and growing have to still face this and say, “Let’s move through this. Through the face of discomfort, we can grow.” A lot of complexity, new things happening, shifts, changes, that’s an example of some discomfort that I’ve had to go through.

Continued growth as well, we’re growing our team. We’ve got a new individual joining our team who’s got the potential to become a COO of our team. This is someone who’s got a huge amount of capacity. At the same time, for us, it’s a little bit uncomfortable because we’ve got to bring in a new leadership role within our company. There are so many different things but it’s this constant conversation that I have to have with myself.

If you want to be successful in real estate, you always have to take the long view.

How do you know when to contract or say, “Let’s circle the wagons and maybe assess where we are before we go take on more?”

We’re always having this decision whether we’re an expansion or contraction. I would err towards expansion constantly because we’re telling ourselves who we are or a little bit about our identity every time we make a decision. I would certainly err more on the side of expansion if possible. There are certainly times in real estate that can get extremely risky if we don’t know what we’re doing. At that point in time, it’s okay to contract, ask more questions, take things a little bit slower and maybe bring more people onto your team, perhaps pass on a deal if you’re not ready for it. I would certainly err on the side of expansion because we’re not going to know everything.

Sometimes we have to take the first step, let the momentum carry us through and recognize that no matter what, we will do whatever it takes. My mentality is, “Whatever it takes.” I know that I can be resourceful and creative. It’s not about having the resources but being resourceful and having resourcefulness, finding solutions and opportunities to correct errors. Typically, within the frame of this conversation, no mistake that we make in real estate is fatal within reason. What can we do to expand through failure is gain that feedback? For me, I always try to err on the side of expansion.

Let’s go back to your story a little bit. You launched your brokerage firm. Was that on the commercial side or residential side? You weren’t in love with residential.

 

That was on the commercial side. I was only doing residential for a very short period of time early in my career. It was great for me to learn this business being a commercial broker. The reason why is because I could see how investors are looking and maximizing deals. It was interesting because over several years in some cases, you would see investors go into a certain deal, reposition the deal and then exit. I’d be on both sides of those transactions, which is always exciting. That was a great way for me to dig in and immerse myself into this business. I didn’t have any friends, family or any background in this business. For me, that’s all I knew.

I knew that I could generate more income through being a broker. I founded a commercial real estate brokerage company and ran that for a few years. As I decided to fully transition into the multifamily investing side of things, I decided to back away from the brokerage business because I didn’t want to be a competitor with our broker colleagues who collaborate with us in terms of our acquisitions. That was the decision that I had to make. It was a tough decision. A lot of people in this business get in and create substantial success in the business. It’s very tough to go away from those types of fees that you generate. That was a challenge but that was the path that I took.

It goes back to moving through discomfort. It’d be a tough decision because I’m sure you had other agents, people working for you, guys building systems and processes. You had it all running. It was a machine and you go, “I’m going to shut this down.”

I had to take three steps back to take one step forward then another. It took two years before that transition made sense. It was very uncomfortable.

Those are things that people don’t think about. There’s a lot of readers probably that are W-2 employees and things like that. That fear and trepidation of in your case is a machine that’s making money. You said, “If I took two years, will that become full circle?” It’s like, “This is a lot to consider.”

The other thing too is that if you want to be successful in real estate, no question as an investor but as an entrepreneur and practitioner, you always have to take the long view. To me, two years fly by. Unfortunately, and sometimes, if you’re going through a challenging transition, in some ways, it’s like, “I’m glad that transition is over.” In other way, it’s like, “Two years is going to come and go.” The question is, what are you willing to commit to? What do you want your vision to be in your future? What type of lifestyle do you want to design?

The thing that I realized as a broker is while I was generating a high income, it was not the lifestyle that I wanted. While I was a commercial real estate broker, I was in high, constant demand all the time. I was like, “I’m not sure if I want to build a family with this type of lifestyle.” I’m looking at real estate and saying, “This is the vehicle. What can we do to shift the way that this vehicle serves me? That was the reason why I made that decision.”

What is the lifestyle you want?

Find comfort in being uncomfortable.

I want a lifestyle where I can learn, grow, share experiences with people like yourself, where I can inspire and be inspired. I’m driven by learning, growth, experience, challenging myself while it still is not comfortable. Even with that phrase, it’s important to find comfort in being uncomfortable. It’s still not natural. For me, it’s this challenge. I can look back on a Friday, at the end of the year, at the end of a quarter, look back and say, “I’m proud of myself.” What makes life worth living is going through a bit of challenge, expanding and evolving. I call it elevating in many ways. I love to travel, see the world, meet new people, try new food, read new books and spend time with my family. That’s the vision of my life is all about.

You grew up in a middle-class family. No one was thinking in these terms, expand your mind or how to move forward. Did you ever get any blowback from family or from people that didn’t understand what you were doing or going, “Hang on a second. What’s Tyler doing again?”

My family still has no clue what I do. They’re like, “You’re doing this little podcast thing. What’s going on with that?” I get where they come from but they’ll ask me, “How’s work? How’s your job?” I don’t think my family still understands what I do. What I try to do is I try to be who I am. The thing that’s interesting is that I’ve changed a lot from who I was growing up. Maybe a lot of people in my family still see me as. Hopefully, they see that I’m trying to grow, change and always be constantly becoming the next version of myself. I hope that rubs off on them in a positive way. That’s been my biggest thing.

I read this super simple book years ago and you may have read this too. It’s called Who Moved My Cheese?. The message of that book resonates with me. It has become a central theme of my life. It’s always about changing and growing. I think my family had slowed down on their questions because they are a little bit confused about it but it is interesting. Does your family ask you anything? How does that resonate with you?

I asked because I could sense that the answer was going to be the same as mine. I got that question from one of my brothers like, “How’s that show thing going?” I’m like, “It’s going great. Thanks for asking. You have no idea what I do. It’s all good. I get to connect with the best and brightest across the country 365 days a year.” That’s awesome. They don’t get it.

They’re like, “What’s that do for you?” I’m like, “How are you?” Tyler, I’ve thoroughly enjoyed this. We never even got into your business, into multifamily or how you’ve grown that. Maybe we’ll save that for another time. Before we jump into the final four questions, is there anything else that’s been top of mind that you’d love to share with the readers?

When you think about multifamily real estate, you think about real estate in general. It’s a vehicle towards creating an outcome that you want in your life. The question is, how can we reverse engineer that? We can get to practical terms about what type of cashflow is required to cover your expenses, burn rate, those kinds of things and beyond so that you can live a life free following your passions and doing these things. It does come down to continuing to invest in yourself. The things that are important for investors to consider is we need to continually study what’s going on in this economic environment. I had an economist on my podcast. We’re talking about the set of circumstances that we’re experiencing.

We’re in uncharted territory. Investors need to be fully aware of what’s going on with currency, migration, geopolitically, materials, labor, all these different things. That’s critically important. I would encourage the readers also to study their own psychology, psychology of others, understand how you can influence and impact other people in a stronger way because, at the end of the day, real estate is a people business.

It’s bricks and sticks, cashflow, NOI, IRR and all these things but ultimately, it’s all about people making decisions. Those are critically important. Also, mastering our own emotions because we think, feel and behave in certain ways based on how we feel and affect. Did we get enough sleep? What did we eat? How much water have we drunk? How much exercise have we gotten?

 

These are all very different things but if you want to be a high performer, it’s about studying widely, understanding deeply and surrounding yourself with an amazing team of people who can be experts for you in certain ways. They can serve you. You can serve them because a big philosophy that I’m fond of is who not how. You need to learn, grow, expand but also you don’t need to know everything. You don’t need to be the expert in every way. If you want to be a high performer in real estate, it’s about surrounding yourself around great people. Continuing to learn, adapt and grow. That’s what I’m passionate about and what I would share with your readers.

Tyler, I certainly enjoyed this. Thanks for sharing everything you’ve shared. This has been great. The final four questions are this, if I gave you $20,000 to invest in real estate with no previous real estate investing experience, what would you do with it and why?

If I was going to put $20,000 into real estate, I would start with a duplex and houses, little to no money down, probably 3.5% FHA mortgage. I’d never done that but it’s a great way for people to get started, start developing systems and get in the game but otherwise, I would consider investing in your own learning. The best way you’re going to get a return on your investment is to invest in yourself. Maybe if you could do 3.5% down and you got some more money leftover, buy a bunch of books, invest in a conference and meet people. That’s what I would suggest.

If you could help our readers avoid one mistake in real estate, what would it be and how would you avoid it?

Ask more questions. This is one of the biggest mistakes I made early on. I’ve got to ask more questions and show more humility because my default is, “I’m the expert.” It’s something that I have to be aware of myself. My own identity is that I want people to think that I’m the expert. Don’t be shy. Ask more questions. Don’t be like me because it can cost you a lot of money. Costing you money can be valuable in the long run because the lessons are valuable but ask more questions is what I would suggest.

When it comes to investing in the world, what’s one thing you’re doing to make the world a better place?

Our tagline, philosophy and mission with CF Capital is elevating communities together. The way that we do that is we invest in high-value multifamily communities. Instead of being a slumlord, we go in and do the right thing. We don’t cut corners. We treat our residents, staff and community right. Through this process, not only our investing partners, our lives and our families elevate and improve but also communities do and our staff does.

We talk to people about things that you and I are talking about, expanding our mind, our leadership capacity, our circle and through discomfort. Through this process, we get to create amazing returns on investment but we also get to create communities that thrive as a result. Elevating communities together is the way that we create impact and income at the same time.

Last question, if our readers want to get in touch with you, what is the best way to do that?

Check us out at CFCapLLC.com. That’s where you can learn more about our company CF Capital and then also for your readers, I would encourage them to come check out Elevate Podcast. We’re everywhere. You can listen or watch the podcast. You can check that out at ElevatePod.com.

Tyler, thanks so much for your time. I do appreciate it.

Thank you so much, Sam.

 

Important Links:

• CF Capital
• Elevate
• Think and Grow Rich
• Who Moved My Cheese?
• TylerChesser.com

 

About Tyler Chesser

Tyler Chesser, CCIM is a high-performance real estate entrepreneur who helps real estate investors, leaders and entrepreneurs transform their businesses and lives. A successful real estate investor with a background as a former perennial top-performing commercial real estate broker, Tyler started investing in multifamily real estate in 2015 as a way to build wealth and create diverse income streams for his family.

Prior to launching his real estate investment firm, CF Capital, Tyler spent over seven years in the business as a founding principal of a successful commercial brokerage company, real estate investor, professional speaker, and award-winning sales professional. Today Tyler offers a range of services and programs – from syndication of private passive investment opportunities, individual to group business coaching, real estate consulting, keynote speaking and hosts a top 200 business podcast internationally called Elevate.