WS198: Designing A Life Without Limits with Tyler Chesser

RES 198 | Designing A Life

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A lot of times, real estate investors get caught up in the numbers, deals, and all the different challenges that they face and things that they have to overcome to be successful in real estate. However, have you ever stepped back and ask yourself the purpose why are you doing this? Tyler Chesser, the Founder and President of The Chesser Companies, looks at real estate as a vehicle for designing a life. For him, one needs to have a deep sense of purpose and know their why as well as put systems in place to be successful in this business. Tyler dives into developing our why, applying CRM systems to our lives and businesses, and developing our greatest capacities. He also reveals the number one thing that has contributed to his success.

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Designing A Life Without Limits with Tyler Chesser

Our guest is Tyler Chesser. Thanks for being on the show, Tyler.

Thank you so much for having me, Whitney. I’m excited to be here.

I met Tyler in Denver at an event and he is an all-star. He is highly motivated and helping lots of people in this industry and doing some very big things. I knew he’d be a great guest and could provide lots of value. He is the Founder and President of The Chesser Companies, a leading commercial real estate broker, personal development thought leader and a multifamily investor transacting over $50 million in deals since 2013. He’s an award-winning pro, named the KCREA, the Kentucky Commercial Real Estate Alliance Multifamily Broker of the Year and the Kentucky Real Estate Exchangors of the Year. He is a rising star at 30 and Under globally in commercial real estate by CCIM and CIRE Magazine, and 20 People to Know in Real Estate by Business First. He’s killing it. He’s doing some big stuff. His passion is designing lives of fulfillment through personal growth and real estate investing for his clients, his partners and people he influences. Tyler, thank you for the time and being on the show. Give the audience a little more about who you are and what you’re doing in real estate?

I look at real estate as a vehicle for designing a life. A lot of times, we get caught up in the numbers, deals, team and all the different challenges that we face and things that we have to overcome to be successful in real estate. What I challenge my clients and people that are in my network to do is to take a step back and say, “Why are we doing this?” It’s a question that’s not asked enough in our industry. Having that purpose and realizing what is it that’s going to create fulfillment within your own life? What’s going to create fulfillment in my life is going to be different than what’s going to create fulfillment in your life. We’ve all got to introspectively dig there.

Obviously, we’ve got to put the systems in place to be successful in this business. Whether you’re investing in syndication as a passive investor or whether you’re a sponsor, whether you’re a broker, whether you’re a property manager or service provider or whatever it is. I want you to step back and say, “What is it that we’re doing? Is my day-to-day operation creating what I want in my life?” If we truly do ask that question, we will design a portfolio that will provide that life that we’re looking for. If we all take a step back, we originally started on this path for a reason and we get so caught up in the minutia of the day-to-day that obviously, we’ve got to do what we’ve got to do to succeed. For me, it’s all about designing that life without limits. Real estate is so beautiful because it allows us to do that. Not only that, but it also allows us the ability to seeking and developing within ourselves our greatest capacities.

This is a very challenging business. I know for sure for me, when I got started, I didn’t know much. I didn’t have any family in the business. I didn’t have any close friends. I had to seek and find my mentors. I had to dig deep within myself to be able to figure out, “What are my true skills and what can I do to maximize those? What are my weaknesses and how can I outsource those? How can I surround myself with people that are going to make me better?” That’s been my journey and it’s been a beautiful journey because it caused me to dig so deep within myself to be able to develop some of those talents that maybe I didn’t even know I had. I’ve become so passionate about personal development and seeking knowledge and learning and applying those things in my life. Not only my life but in my business. Business is a vehicle towards designing that life. It’s been such a great journey and I’m looking forward to hopefully many more years of what’s to come.

I could tell by our first conversation when we met that you’re a top performer. The way people carry their selves is important. It’s great to meet you. It helps build other people up too when you can operate at that level and teach and you’re leading people. I appreciate that. You talked about your why, “Why are you doing this?” That’s not asking enough. When I first got started thinking bigger in an entrepreneurial type mindset, you hear that so often, “What’s your why? Have you developed your why?” Initially I was like, “Let’s get to the meat and potatoes here.” If I hear that again, I’m going to cut that off and go look for something else. A little bit further into the business, it’s like, “No, this is so important and helping me. That’s why I’m getting up in the morning or why I’m pushing so many hours or working so hard to make this happen.” How did you develop your why and when did you determine that, “This is very important in my business?”

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It continues to evolve. That’s also one of the most beautiful things about this business is that it moves very quickly and you have to evolve. Everyday is different. My why a few years ago is certainly different from the why now. I do think a lot of people here that Start With Why, which is a great book, if you haven’t read it, I highly recommend it. It sounds very simple and it’s like, “I don’t need to read the book. I get it. You’ve got to have a purpose.” Truly, you do have to have a deep, a real sense of purpose. For me, I’m super passionate about growth and learning, growing and becoming better and offering that to other people. It’s such a beautiful thing that we all take for granted. A lot of people go to school growing up, and a lot of people would go to college. Once they leave college, they never pick a book up for the rest of their life and the thought process behind that is, “I’ve learned everything I need to learn.” For me, I’m always seeking new wisdom and new profound knowledge to impact my life and impact the people around me whose life that I care about and people that I care about. With that, a contribution is another huge piece of my why.

I want to be able to help other people design their life, and I’m doing that through brokerage, through real estate investments, through coaching in different ways. Those are my two core beliefs as far as why I get up out of bed every single day. I try to put that focus on others. I noticed that when I focused on myself, I started to realize how many issues are going on in my life when there’s a lot to be grateful for. The third piece there would be love and connection. These are basic human needs that if anyone studies the things that Tony Robbins talks about are very familiar with. These have become deeply ingrained within the core of who I am. It’s a beautiful thing to be able to say, “I’m going to get over whatever challenge this is because I know for sure my growth, my contribution, my love and connection, they’re offering me the ability of going after them and doing whatever it takes.”

Tyler, being a top performing broker and you’re performing at this level and you talked about having the systems in place to be successful. Can you elaborate a little bit on some systems that have helped you be successful that we can all apply to our lives and businesses?

This is certainly one of the pieces that I have still much more room to grow. I read a book called Traction. If anybody hasn’t picked up this book, you have got to read this book, it is amazing. I’m working on implementing a lot of different systems. That book is a Bible for building a business. For me, a lot of what’s in there is what I’m building. I certainly use CRM and project management software and also different databases that allow me to communicate with my team and others. At the end of the day, we’ve got to keep it simple. “Complexity is the enemy of all execution” as they say. You want to try to keep it as simple as possible but I’m always testing systems. I’m always testing procedures that we can implement in our business. Policies and procedures and at least checklists to say, “If we’re doing a new deal, we’ve got a comprehensive due diligence system that we don’t have to recreate the wheel a lot. Or we’re negotiating a deal and here are the main points we want to go over. Here’s a way that we can tap into psychology as well as facts and principles of the deal.” We have a system for everything that we do and certainly, we’re always refining that. I’ll be glad to dig down to any of those in specifics but that’s a general overview.

What CRM do you use?

I use Podio. Podio is nice because it also allows you to do project management as well in communication with your team. I’m still in the early stages of testing that out. I was using a different CRM before. I haven’t had a huge, “This has been the silver bullet.” The key is you’ve got to use it and you’ve got to be consistent on it, so continuing to improve in that regard.

I talked to a guy about a CRM and there are so many I’ve looked at and I’ve tried to do research and trying to find the right one. I’ve been using one for a long time. This guy said, “The best one is the one that you use.” You’ve got to keep putting that information in there and stay on top of it. What is something that you took from the book, Traction, or something that you found was like, “This isn’t something I hadn’t thought of before that’s helped my business?”

RES 198 | Designing A Life
Traction: Get a Grip on Your Business

I love the concept of rocks. If you think of a glass and you have a bunch of materials sitting outside of that glass. The only way that you’re going to get everything to fit in there is if you put the rocks in first. If you put the sand in first, you’re not going to be able to fit those rocks in. If you think about it and how that applies to business, it’s so key. “Let’s set our main objective goals for the next quarter, the next month or even the next week. What are our rocks?” I love that because this boils down for me to be able to communicate with my team. It’s like, “Here’s what I believe should be your rocks. Do you agree with this? Do you agree that these are some of the most important things to accomplish here? If they are, let’s set that and let’s go ahead and go after them for the next three months.”

If you do that, it’s such a simple mindset shift that allows you to say, “We’re going to have unexpected things happen in our business. We’re going to have the day-to-day tasks that come up. We have these rocks, so we’ve got to figure out how do we proactively go after these and accomplish them no matter what? If not, the sand is going to go in there. We’re not going to have enough room. We’re not going to have enough time. We’re not going to have enough energy to accomplish the things that are most important in moving our business forward.” That concept itself is extremely important. I can’t say enough about the book, but that’s a great metaphor for looking at how to run your business.

I haven’t heard that before. I’ve seen that analogy before with putting the rocks and the sand. You’ve put numerous things in then put water in. I haven’t heard that related to business and developing those goals that way. As far as you said about day-to-day operations and being able to create the life that you want. Tell us some ways that you’re creating the life that you want through your day-to-day operations. What are some daily things that you find are the key to performing whether it’s on a personal level or whether that’s with your team?

For me, it’s a person to person business and it’s all about growing those relationships. Every single day I’ve got multiple meetings with other individuals and we’re sitting across the table from each other. Maybe we’re working on a deal right now or maybe we haven’t worked on a deal for a couple of years or maybe we’ve never worked on a deal. It’s more so building that relationship because at the end of the day, not only is this business allows people to design a life, but it allows people to do what’s important to them. For me, it’s all about the person to person relationship and building experiences for my clients that they’re saying, “I can’t believe he went above and beyond in every regard.” It’s not because of anything other than the fact that I care about other people.

For me, the most important thing is to be in front of people, having discussions about what’s important to them and helping them craft their goals and their objectives and obviously, discussing the nuts and bolts of real estate. “What’s going on in the market? What’s going on in this submarket? What are you seeing with interest rates? What are you seeing with different management companies? What other job opportunities that tenants are very inclined to make certain decisions on?” That’s the biggest key for me is either having discussions or being in front of people, breaking bread or having a cup of coffee. That’s the basics for me but that’s an everyday key for my success.

You mentioned developing our greatest capacities. I like that because if you don’t get out of your comfort zone, if you don’t try it a little bit, you don’t even realize what you’re capable of. You stay back here in what you think is comfortable, but you never grow. Tell us some ways that you’ve experienced that or seen that happen in your own life.

One of my first coaches in this business, he actually impressed upon me the fact that you have to become comfortable being uncomfortable. To me, it took me a little while to understand what he means by that. As I grew in the business, I started to realize, “Every day was very uncomfortable in different ways.” A prime example for me was in the beginning when I felt I didn’t have enough knowledge or I wasn’t as much of an expert as I want it to be or I strive to be. In a negotiation, I felt very intimidated because, “What if I say something wrong? This could cost them hundreds of thousands of dollars or even more.” I got very stressed about it. What it caused me to do is to do my homework, to write out my thoughts before I had a conversation, to do the extra bit of research. I was very worried that if I didn’t do the right thing, then I would be costing my client, partners or myself a lot of money. For that, it caused me to become a great negotiator.

[bctt tweet=”At the end of the day, we’ve got to keep it simple because complexity is the enemy of all execution.” username=””]

I actually noticed this as well when it comes to public speaking. A lot of us have an innate fear of speaking in front of other people. What that’s always caused me to do is extra preparation, to practice, to realize that I’m going to forget certain things and to play off that in different ways. That’s one of the keys is to use that fear and use that worry to your advantage. Another thing is we’re never going to get rid of fear in our life, but if we can use it and we can dance with it, it will be something that actually allows us to ascend to that next level. Honestly, I would say in my business, probably the most valuable thing that I do for people or myself or partners is a negotiation. It’s because of the fact that I was so scared and worried about it in the beginning. I had so much fear around it that it caused me to dig so deep.

I liked that you mentioned that you had a coach. I find that most people that experience high levels of success, they had coaches early on and those coaches even evolved. You get different coaches for different parts of your business possibly. As you progress, you want coaches that are further along in their either coaching ability or their business as well. I like the way you said that it’s yet to become comfortable with being uncomfortable. I remember I was asked to speak at REI club at a local real estate club. Right away I’m like, “Do I want to do that?” I remember thinking, “I need to commit and then we’ll make it happen.” I said, “I’ll do it.” Then I had to do it, but that was good and me getting in the mindset of what you talked about. Even though it was out of my comfort zone, it helped progressed me to being able to wanting to do it the next time or when I’m asked again, it’s not as big a deal now. I’m confident in being able to provide some value to people that are there.

It’s so amazing too when you overcome that fear and you reach the other side of that, the satisfaction that you have within yourself. That’s how you create love in yourself is when you overcome challenges. To me, that’s one of the greatest parts of our business too is that it is very challenging. Not only having a great negotiation or speaking in front of other investors or service providers or people interested in the business. There are so many other things that can create fear in this business. If you can overcome those things, think about not only the satisfaction but obviously the accomplishments that come thereafter. It’s a beautiful thing.

I think that goes into also where you talked about developing talents that you didn’t even know you had or helping others develop those talents. If you don’t ever get uncomfortable, you can’t even find this other passion that you have or the skill that you may be good at. You being an active investor and a very experienced broker, I wanted us to be able to get into that relationship component. We’re not going to be able to do that now, but we’ll have to have you back to talk more in-depth about that. I wanted to ask you, what is the number one thing that you would say has contributed to your success?

The number one thing that’s contributed to my success is recreating myself daily. It’s not resting on my past laurels. It’s not saying, “I won this award, you should hire me.” It’s becoming better and better every single day. Everyone talks about their morning routine. My morning routine is all about getting better. I get up early and I seek information. I learn new information. I’ve become aware of my mind through meditation. I work out. That’s the foundation of growing every day and then building on that and allowing the things that I’ve put the work in for to manifest themselves during each day. For me, it’s all about seeking new information, applying it to my life and to my business immediately. That’s been the key for me.

How do you like to give back?

I’m very passionate about my contribution. I am involved with the Louisville Apartment Association called the Outreach Committee. We volunteer every month and we work with a group called the Gilda’s Club here in Louisville. That is a group for individuals with cancer. We serve meals to them. We also work with the Ronald McDonald House as well as others. For me, that’s been great. Honestly, you forget about any challenge that you have in your life when you’re giving. That’s one of the reasons why I respect you, is what you’ve done with your contribution in the way that you continue to grow that. I think that’s such an amazing way for you to stand out. I’m extremely passionate about growing that. I’d love to start a foundation one day. It’s one of my goals. I appreciate that question. It’s a question that’s rarely asked.

RES 198 | Designing A Life
Designing A Life: There are so many things that can create fear in this business, but if you can overcome those things, the accomplishments that come thereafter is a beautiful thing.

I appreciate how you give back and pursuing that. Thank you again, Tyler, for being on the show and going through this mindset change. Helping people to get out of their comfort zone and why that’s so important. Talking about mindset initially was like talking about my wife, “Let’s get to meet and tell you this. How do I find a property? How do I underwrite it?” The longer I’m in this, the more successful people I meet. That’s one of the biggest things they mentioned is their why and their mindset. It’s good for us to focus on that. I appreciate how you’ve elaborated on the importance of that and what it’s done in your business. Tell the audience how they can learn more about you and get in touch with you.

You can visit my website at or you can connect with me on Twitter and Instagram, @TheTylerChesser. I’d love to connect with your audience. If they visit my website, they can also subscribe and we connect on a weekly or monthly basis. I do write blogs and such. I love to connect with people and meet people and try to figure out how I can help others overcome their challenges.

Thank you so much for offering that, Tyler. I hope the audience will connect and reach out. That’s how so many I find to get started also is by reaching out to guests on podcasts or hosts like myself, either way, I’m happy to help. I hope the audience will take advantage of that. I hope you’ll all go to Life Bridge Capital and connect with me. Go to the Facebook group, The Real Estate Syndication Show so we can all learn from experts like Tyler and grow our business together and from the mindset to the why to actually doing a deal. We want to help you through the process. We will talk to you soon.

Thank you very much.

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About Tyler Chesser

RES 198 | Designing A LifeTyler Chesser, Founder and President of The Chesser Companies, works with individuals, partnerships and other entities on the marketing, sale, and acquisition of income-producing real estate including multifamily, retail, office, raw land and light industrial. Mr. Chesser is also an investment real estate professional, building successful partnerships in the multifamily real estate space.

Real estate acquisition and disposition can be a complicated endeavor. We focus specifically on our clients’ unique needs and goals through consultation, negotiation, and detailed transactional management. Additionally, we believe in the power of personal development and are passionate about helping our clients and partners succeed through a consistent life-changing regimen. Our goal is to create thriving clients and partners for life through outstanding results.

Tyler is an innovative & dynamic commercial real estate sales professional, a personal development thought leader, and a multifamily real estate investor with experience in international marketing, market research, & direct sales for global fortune 500 corporations. Recently recognized as a “Rising Star” 30 & under internationally in commercial real estate by CCIM Commercial Investment Real Estate (CIRE) magazine & one of the “20 people to know in real estate” by Louisville Business First, Tyler Chesser has become a nationwide leader in the income-producing real estate investment world.

His uncanny grasp of market complexities, a deep passion & skill as a leader, & a mastery of investment analysis formed a perfect match in investment real estate. His unique approach of pragmatism along with a systematic personal development regimen set him apart from the crowd. Known to be an avid continuous learner, Tyler consistently reads a book a week and applies intelligent knowledge immediately in his business and his life.

A strong & principled negotiator, Mr. Chesser has a reputation of delivering expansive results for his clients & partners in each & every transaction. As a CCIM designee, his expertise equips his clients & partners to ensure their long-term success. Being a real estate professional with a background in marketing, property owners feel comfortable that Tyler will effectively garner substantial demand for their property through innovative marketing strategies. His commercial real estate brokerage expertise includes various asset classes such as multi-family, office, industrial, retail & raw land. Tyler is an award-winning pro, recently named the KCREA 2017 Multi-Family Broker of the year, and the KREE 2018 Exchangor of the Year.

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