Meet the Team: Q&A with Tyler Chesser

To continue our “Meet the Team'' series, we would like to share with you a Q&A session conducted by Bryan Flaherty with Co-Founder and Managing Partner of CF Capital, Tyler Chesser (see bio).   Before we begin, we would like to recommend and guide you to a “pride and joy” of Tyler’s, The Elevate Podcast.  We highly recommend you take a look (and listen) if you are looking for perspectives on personal growth and real estate investing.

Interviewer (Bryan Flaherty - “Bryan”):  For some consistency, how about we follow the same format as my interview?  To break the ice, would you be able tell us a little about your background, before entering the real estate world? 

Tyler Chesser (“Tyler”): It would be my pleasure! After all, who doesn’t love talking about themselves? In all seriousness, out of college I began my professional career as a corporate employee for a multinational restaurant company as a marketing coordinator, after taking a brief stint in sales for a global manufacturer. I worked in several different functions as I “climbed” the ladder from digital marketing, to market research, to international marketing. While I truly loved the work I was doing and was enthralled with positioning a brand entering new markets all over the world, I found that I was beginning to “tolerate” my lifestyle, which seemed to encompass working from 9 to 5 and living a fairly average life outside of work. Somehow I knew deep down that I was destined for more and had a subconscious desire to live a massive life. I began asking myself powerful questions on what else might be possible for me, which ultimately led me to get my real estate license and start selling real estate. I ultimately found a phenomenal fit in real estate sales and built a commercial real estate boutique brokerage company. We carved a significant niche in the middle market multifamily space, and I enjoyed a substantial level of success. I ultimately pivoted, as I had been investing in multifamily along with selling for several years, into investing focused rather than sales focused. I made this shift because of how much I believe in the asset class and all the benefits it provides to people who use it as the vehicle it was designed to be. It’s become a lifestyle vehicle and a passion for me to continue to raise my own performance to meet the demands of the market and our team.

Bryan:  May I ask, what did you want to be when you were growing up?

Tyler:  As a kid growing up, my heroes were Michael Jordan, Scottie Pippen, and later Kobe Bryant. It was a no brainer that I always dreamed of being an NBA player as I shot hoops every day in my back yard, rain, snow or shine. As I got older, I became obsessed with human behavior and the psychological aspects of branding, marketing, and communications. I set myself on a path to learn and become an expert in marketing and branding. My first dream job was to be the CMO of Nike, a brand that had a lot of influence on my childhood growing up, and I’ve continued to chase my curiosities to this day which leads me to what we’re now doing with CF Capital and how we’re positioning the firm, our assets, and how we’re paying attention to the behavior of our staff, residents, investors, and team members. I deeply love the influence we can have as a result of truly understanding what moves people. I still love basketball, and maybe one day I will be involved with the NBA in a different capacity as my aspirations outpaced my on the court talent! However, I firmly believe there’s a reason for every inspiration we have, and that desire has proven to be a calling card in my life.

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Bryan: How did you originally get involved in real estate and the multifamily market?

Tyler: Originally, I got my real estate license in 2013 and transitioned from a W2 corporate employee to real estate agent. When I entered the real estate business, I had no idea all the different twists and turns my career would take me - all I knew is that there was something more available to me and my intuition led me down this evolution. I originally thought I would sell properties for commissions and would pivot from being a marketing specialist for a large organization to a sales professional within real estate, as simple as that. As I grew my business by referral and by surrounding myself with some of the best in the business, and once I learned about the power of cash flow, asset appreciation, tax strategy, compound interest, leverage and all the great things about real estate, I became fully immersed as a real estate investor. I ultimately grew a boutique commercial real estate brokerage company as well as a multifamily real estate portfolio on the side, from the ground up prior to transitioning into being a full time real estate investor. 

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Bryan: What motivates you every day to get up out of bed everyday?

Tyler: I am driven by the notion that “there’s always another level,” and that challenges are what bring out our full potential. 

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Bryan: Since beginning your journey with CF Capital, what do you think has been your greatest achievement? 

Tyler: We navigated a very tumultuous 2020 and have established a substantial market presence while remaining true to our objectives. It is centering to know that in a noisy world we can remain committed to our goals no matter what.

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Bryan:  Off the top of your head, were there any mentors or even books that have influenced you the most to get to where you are today with CF Capital?

Tyler: I am a firm believer that “success leaves clues” and mentors have been highly impactful in my life. I’ve been investing in executive coaching for years and those experiences have been substantially transformative. Aside from that, I look to Tony Robbins, Kobe Bryant, Napoleon Hill, Tim Ferriss, Sam Zell, Robert Kiyosaki and so many others as mentors. Many of the guest’s I’ve interviewed on Elevate Podcast have become mentors of mine. I invest in masterminds to surround myself with people who are much smarter than I am in many different capacities. I am always willing to soak up the wisdom of others. With regard to books, I read roughly a book per week and there have been countless books that have been references for me along this path. I’ve recently enjoyed “The Art of Impossible” by Steven Kotler, “The Big Leap” by Gay Hendricks, “Influence” by Robert Cialdini, “What it Takes” by Steven Schwartzman and so many more. Books and wise people are what have truly built me and continue to build me to be a leader and visionary for our company.

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Bryan: So you and I read books together… Out of all the books that we have read during the pandemic, do you have a favorite? 

Tyler: We’ve loved many books together and constantly challenge each other’s level of thinking. A couple that stick out for us are “Traction” by Gino Wickman and “Thinking in Bets” by Annie Duke. Both books influence our activity and thinking on a daily basis.

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Bryan: What are your plans and goals for the future of CF Capital? What are you most excited about?

Tyler: Well, I was recently told by an expert in neuroscience that we should actually keep our goals to ourselves, for reasons I won’t get into in this interview, but ultimately to protect the likelihood of our reaching those goals. With that said, we ultimately want to build CF Capital into the vehicle it has the potential to become and beyond to help others realize and capture the reality that they can live a life of fulfillment and a life of “toleration” doesn’t have to be their destiny. I observed myself early in my professional career tolerating my life, and when I started experiencing success in real estate learned that we can live a life of fulfillment, freedom, and impact if we let this vehicle serve us to our highest capacity. I also learned that the more you demand of yourself and the more you believe in yourself, the more satisfaction you will have in your life. I have a strong desire to share the beautiful benefits of this business with many others at scale so that more people can bring their zone of genius to the world, to their families and their communities.

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Bryan: To finish things up, I wanted to ask, ‘what advice would you have for an up-and-comer in the multifamily world?’  

Tyler: Be willing to fall in love with the mundane fundamentals. Never stop learning. Focus until you’ve proven one concept successful before moving to your next endeavor. Learn about mindfulness. Ask yourself and others powerful questions. Learn about your own psychology and the psychology of others. Learn about macroeconomics, marketing, leadership, and communication. Surround yourself with great people who have pure intentions. Model success, because you don’t have to recreate the wheel. Seek inspiration daily, like you would take a shower and brush your teeth. Listen to Elevate Podcast!

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